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USRE26433E - Amide and imide derivatives of metal salts of substituted succinic acids - Google Patents

Amide and imide derivatives of metal salts of substituted succinic acids Download PDF

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USRE26433E
USRE26433E US26433DE USRE26433E US RE26433 E USRE26433 E US RE26433E US 26433D E US26433D E US 26433DE US RE26433 E USRE26433 E US RE26433E
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36Oxygen or sulfur atoms
    • C07D207/402,5-Pyrrolidine-diones
    • C07D207/4042,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412Acyclic radicals containing more than six carbon atoms
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    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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    • C08F8/44Preparation of metal salts or ammonium salts
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Definitions

  • Oil-soluble metal salts of substituted succinic acid acylated aliphatic polyamines and processes for their preparation are exemplified by the alkali, alkaline earth, lead, cadmium, zinc, nickel and cobalt salts of polyisobutenyl-substituted succinic acid acylatea' alkylene polyamines.
  • the salts are additives for lubricating compositions.
  • This invention relates to new chemical compositions and to mineral oil compositions containing the same and, more particularly, it relates to a novel class of chemical compositions which act as dispersants, detergents and oxidation and corrosion inhibitors. Still more particularly this invention relates to amide and imide derivatives of metal salts of substituted succinic acids.
  • the prior art has shown a need for efficient dispersants to hold in suspension products caused by oxidation or deterioration of a motor oil during service life, as well as other insoluble particles so that they do not settle out and form varnish or sludge or interfere with the lubrication or functioning of the various mechanical parts. Also, dispersants are useful to hold in suspension additives for specific purposes which would otherwise be insoluble in the mineral oil.
  • the prior art has shown also the need for efficient oxidation and corrosion inhibitors to prevent or reduce the de osition of lacquer or varnish-like coatings on the walls of the cylinders, piston rings, etc., and to prevent or reduce the corrosion of engine parts, bearings, etc.
  • An example of a specific purpose served by a corrosion inhibitor is the prevention of copper-lead bearing corrosion.
  • compositions which are adapted for use as additives in hydrocarbon oils.
  • compositions which are useful as dispersants and oxidation inhibitors in lubricating compositions are also an object of this invention to provide compositions which are useful as dispersants and oxidation inhibitors in lubricating compositions.
  • compositions which are useful as dispersants and oxidation inhibitors in hydrocarbon oils are also an object of this invention to provide compositions which are useful as dispersants and oxidation inhibitors in hydrocarbon oils.
  • an oil-soluble nitrogen-containing metal salt composition prepared by the process which comprises reacting, at a temperature within the range of from about 20 C. to about 250 C., (A) about two equivalents of a succinic compound selected from the Re. 26,433 Reissued Aug.
  • hydrocarbon-substituted succinic compounds of the oil-soluble nitrogen-containing metal salt composi tions are readily obtainable from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon or other high molecular weight bydrocarbon containing an activating polar substituent, i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to the reaction with maleic anhydride or the acid thereof.
  • Said reaction involves heating equivalent portions of the maleic anhydride and hydrocarbon, for example, at a temperature within the range of from about 100 C. to about 200 C.
  • the resulting product is a hydrocarbon-substituted succinic anhydride.
  • the succinic anhydride may be hydrolyzed to the corresponding acid by treatment with water or steam.
  • the hydrocarbon-substituted succinic acid is preferred, for the purposes of this invention, when the basic metal reactant is reacted before the polyamine and the corresponding succinic anhydride is preferred when the polyamine is reacted before the basic metal reactant.
  • the principal sources of the hydrocarbon-substituted radical include the high molecular weight petroleum fractions and olefin polymers, particularly polymers of monoolcfins having from 2 to about 30 carbon atoms.
  • the especially useful polymers are the polymers of l-monoolefins such as ethylene, propene, l-butene, isobutene, l-hexene, l-octcne, Z-methyl-l-heptene, 3-cyclohexyl-lbutene, and 2-methyl-5-propyl-1-hcxene.
  • medial olefins i.e., olefins in which the olefinic linkage is not at the terminal position
  • medial olefin polymers contemplated are those illustrated by Z-butene, S-pentene, and 4-octene, etc.
  • interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and poly-olefins.
  • Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene, isobutene and butadienes, propene with isoprene, ethylene with piperylene, isobutene with chloroprene, isobutene with p-methyl styrene, l-hexene with 1,3-hexadiene, l-octene with l-hexene, l-heptene with l-pentane, 3-methyl-l-butene with l-octene, 3,3-dimethyl-1-pentane with l-hexene, isobutene with styrene and piperylene, etc.
  • the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about and preferably at least about on a weight basis of units derived from the aliphatic mono-olefins and no more than about 5% of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percent of olefinic linkages should be less than about 2% of the total number of carbon-to-carbon covalent linkages.
  • interpolymers useful in this invention include the following (percent by weight): copolymer of 95% of isobutene with of styrene, terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene, terpolymer of 95% of isobutene with 2% of l-butene and 3% of l-hexene, terpolymer of of iso-butene with 20% of l-pentene and 20% of l-octene, copolymer of of l-hexene and 20% of l-heptene, terpolymer of of of isobutene with 2% of cyclohexene and 8% of l-heptene, terpolymer of 90% of isobutene with 2% of cyclohexene and 8% of propene, and copolymer of 80% of ethylene and 20% of propene.
  • hydrocarbon substituent radicals include saturated aliphatic hydrocarbons derived from highly refined high molecular weight white oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymer illustrated above or high molecular weight olefinic substances.
  • the hydrocarbon substituent may contain polar substi'tuents provided, however, that the polar substituents are not present in proportions sufliiently large as to alter significantly the hydrocarbon character of the radical.
  • the polar substituents contemplated are those exemplified by chloro, bromo, keto, aldehydo, ethereal, and nitro, etc.
  • the upper limit with respect to the proportion of such polar substituents in the radical is approximately 10% based on the weight of the hydrocarbon portion of the radical.
  • hydrocarbon substituent of the hydrocarbon-substituted succinic compound should be substantially saturated, i.e., at least about percent of the total number of carbonto-carbon covalent linkages are saturated linkages.
  • An excessive proportion of unsaturated linkages renders the molecule susceptible to oxidation, deterioration, and polymerization and results in products unsuitable for use in hydrocarbon oils in many applications.
  • the size of the hydrocarbon substituent of the said succinic compound appears to determine the effectiveness of the additive of this invention as a dispersant in lubricating oils. It is critically important that said substituent be large, that is, that it have at least about 50 aliphatic carbon atoms in its structure.
  • the molecular weight of the hydrocarbon substituent should be within the range of from about 700 to about 100,000. Olefin polymers having a molecular weight of from 750 to 5,000 are preferred. However, higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 are also useful and have been found to impart viscosity index improving properties to the nitrogen-containing metal salt compositions of this invention. In many instances, the use of such higher molecular weight olefin polymers is desirable.
  • polystyrene resin such as polyethylene, polypropylene, polyisobutene, etc.
  • a particularly preferred polyolefin is polyisobutene having a molecular weight of about 1,000.
  • the hydrocarbon-substituted succinic acids and anhydrides are especially preferred for use as the acid-producing reactant in this process for reasons of the particular effectiveness of the products obtained from such compounds as additives in hydrocarbon oils.
  • Said succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin polymer or a chlorinated olefin polymer described hereinabove. The reaction involves heating equivalent portions of the two reactants at a temperature within the range of from about to about 200 C.
  • the product from such a reaction is an alkenyl succinic anhydride.
  • the alkenyl group may be hydrogenated to an alkyl group.
  • the anhydride may be hydrolyzed to the corresponding acid by treatment with Water or steam.
  • CJI high molecular weight hydrocarbons containing an activating polar substituent i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride
  • activating polar substituents are illustrated by sultide, disulfide, nitro, mercaptan, bromine, ketone, and aldehyde radicals.
  • polar-substituted hydrocarbons examples include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc.
  • Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within the range of from about 100 C. to about 200 C.
  • the metals of the metal salts useful in this invention are those metals selected from the class consisting of alkali metals, alkaline earth metals, zinc, cadmium, lead, cobalt, and nickel.
  • metal compounds contemplated are the following: sodium oxide, sodium hydroxide, sodium carbonate, sodium methylate, sodium propylate, sodium pentylate, sodium phenoxide, potassium oxide, potasium hydroxide, potassium carbonate, potassium methylate, potassium pentylate, potassium phenoxide, lithium oxide, lithium hydroxide, lithium carbonate, lithium pentylate, calcium oxide, calcium hydroxide, calcium carbonate, calcium methylate, calcium ethylate, calcium propylate, calcium chloride, calcium fluoride, calcium pentylate, calcium phenoxide, calcium nitrate, barium oxide, barium hydroxide, barium carbonate, barium chloride, barium fluoride, barium methylate, barium propylate, barium pentylate, barium nitrate
  • the amines useful in this invention include alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines.
  • a preferred source of the amine group consists of alkylene polyamines conforming for the most part to the formula wherein n is an integer preferably less than about 10, A is a hydrocarbon radical or hydrogen radical or an amino hydrocarbon radical, and the alkylene radical is preferably a lower alkylene radical having less than about 8 carbon atoms.
  • amines which are contemplated are exemplified by: ethylene diamine, triethylene tetramine, propylene diamine, decamethylene diamine, octamethylene diamine, di(hepta-methylene)triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, tetraethylene hexamine, di(trimethylene) triamine, 2-heptyl-3-(Z-aminopropyl)imidazoline, 1,3-bis (2 aminoethyl)imidazoline, pyrimidine, l (2 aminopropyl) piperazine, l,4-bis(2-aminoethyl) piperazine, and Z-mcthyl-l-(2-aminobutyl) piperazine. Higher homologues such as are obtained by condensing two or more of the above'illustrated alkylene amines are likewise useful.
  • Hydroxyalkyl-substituted alkylene polyamines i.e., alkylene polyamines having 1 or more hydroxyalkyl substituents on a nitrogen atom, are likewise contemplated for use within this invention.
  • the hydroxyalkyl-substituted alkylene polyamine-s are preferably those in which the alkyl group is a lower alkyl group, i.e., having less than about 6 carbon atoms.
  • Examples of such amines include N-(Z-hydroxyethyl)-ethylene diamine, N,N'-bis (Z-hydroxyethyl)ethylene diamine, 1-(2-hydroxyethyl)- piperazine, lower hydroxypropyl-substituted diethylene triamine, di-hydroxypropyl-substituted tetraethylene pentamine, and N-B-hydroxypropyl)tetramethylene diamine.
  • ethylene polyamines are especially useful in this invention. They are described in detail under the heading Ethylene Amines in Encyclopedia of Chemical Technology, Kirk and Othmer, volume 5, pages 898- 905, Interscience Publishers, New York (1950). Such compounds are prepared by the reaction of an alkylene chloride with ammonia which results in the production of complex mixtures of alkylene polyamines, including cyclic condensation products such as piperazines. These mixtures find use in the processes of this invention. On the other hand, quite satisfactory products may be obtained also by the use of pure alkylene polyamines.
  • alkylene polyamine for reasons of economy as well as the effectiveness of the products derived therefrom, is a mixture of ethylene polyamines prepared by the reaction of ethylene dichloride and ammonia and having a composition which, in its elemental analysis, corresponds to that of tctraethylene pentamine.
  • Another especially useful amine for reasons of economy as well as the effectiveness of the products derived therefrom is a mixture of poly(trimethylene) polyamines and the 1,3-trimethylene diamine derived from the reaction of acrolein and ammonia.
  • the process of this invention can be carried out either by (1) first preparing the acylated amine of the hydrocarbon-substituted succinic compound and then reacting said acylated amine with the basic metal compound, or
  • the succinic compound be the succinic anhydride and that trace amounts of water, i.e., up to about 2.5% by weight, be present when the basic metal compound is an oxide.
  • the succinic compound be the succinic acid. In all cases, it is preferred that nitrogen or some such inert gas be bubbled through the reaction mixtures to remove any water formed as a result of the acylation reaction.
  • the first method above involves (A) mixing a succinic compound selected from the class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, with at least about one equivalent of an amine selected from the class consisting of alkylene polyamines and bydroxyalkyl-substituted alkylene polyamines, and heating the resulting mixture to elfect acylation and to form an acylated amine, and to remove the water formed thereby, and then (B) mixing said acylated amine with about one equivalent of a basic metal compound from the class consisting of alkali metal, alkaline earth metal, zinc, cadmium and lead oxides, hydroxides, carbonates and lower alcoholates, and heating the resulting mixture at a temperature "within the range of from about 20 C. to about 250 C. It is preferred that said acylation reaction be carried out at a temperature within the
  • the second variant of the process comprises reacting, at a temperature within the range of from about 60 C. to about 250 C., (A) one equivalent of a mono-metal salt of a hydrocarbon-substituted succinic acid in which the hydrocarbon substituent has at least about 50 aliphatic carbon atoms and the metal of said metal salt is selected from the class consisting of alkali metals, alkaline earth metals, zinc, cadmium, nickel, cobalt, and lead, with (B) at least about one equivalent of an amine selected from the class consisting of alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines.
  • the mono-metal salt may be prepared by heating at a temperature within the range of from about 80 C. to about 130 C., two equivalents of a hydrocarbon-substituted succinic acid with about one equivalent of a basic metal reactant selected from the class consisting of alkali metal, alkaline earth metal, lead, cadmium, and zinc oxides, hydroxides, carbonates and lower alcoholates, for a period of time of from about 1 hour to about 5 hours.
  • the temperature can be as low as 20 C., although usually it should be within the range above.
  • the reaction of the mono-metal succinate with the amine is best carried out at a temperature within the range of from about 80 C. to about 160 C. It usually requires from about 3 to about 5 hours.
  • the mono-metal succinate may be prepared by double decomposition of an alkali metal succinate with an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel and cobalt halides and nitrates.
  • the mono-metal succinates are illustrated by the structural formula:
  • 1'COII where R is a hydrocarbon substituent having at least about 50 aliphatic carbon atoms and M is one equivalent of an alkali metal, alkaline earth metal, lead, cadmium, zinc, nickel or cobalt.
  • the lower alcoholates referred to in this invention are alcoholates containing from one to about 16 carbon atoms.
  • Examples of said alcoholates include methylates, ethylates, propylates, butylates, hexylates, etc.
  • Example 1 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene (having an average chlorine content of 4.3 weight percent and an average of carbon atoms) with maleic anhydride at about 200 C.
  • the resulting polyisobutenyl succinic anhydride has an acid number of 103.
  • To a mixture of 3,264 grams (6 equivalents) of this polyisobutenyl succinic anhydride 2,420 grams of mineral oil and grams of water, there is added at to 100 C., 122.1 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a period of 30 minutes. The mixture is maintained at a temperature of -100 C. for a period of 3 hours.
  • the mixture is heated to 150 C. and maintained at this temperature until it is essentially dry.
  • the mixture is cooled to C. and there is added 245 grams (6 equivalents) of an ethylene polyamine mixture having an average composition corresponding to that of tetraethylene pentamine and an equivalent weight of 40.8.
  • the addition is made portionwise over a period of 30 minutes whereupon the mixture is heated to a temperature of 150160 C. and maintained at this temperature for hours.
  • nitrogen is bubbed through the mixture to remove water formed as a result of acylation.
  • the residue is filtered.
  • the resulting filtrate has a zinc content of 1.63% and a nitrogen content of 1.39%.
  • Example 2 To a mixture of 3,330 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 101 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 71 carbon atoms), 2,386 grams of mineral oil and 75 grams of water, there is added, at 8090 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a 30-minute period. The mixture is maintaind at a temperature of 90-105 C. for 4 hours.
  • a polyisobutenyl succinic anhydride having an acid number of 101 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 71 carbon atoms
  • Example 2 122 grams (3 equivalents) of the amine mixture described in Example 1 is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 105110 C. The mixture is heated at 205-215 C. and maintained at this temperature for 4 hours. Throughout the 4-hour period, nitrogen is bubbled through the mixture to remove water formed as a result of acylation. The residue is filtered. The resulting filtrate has a zinc content of 1.64% and a nitrogen content of 0.72%
  • Example 3 To a mixture of 3,750 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 89.8 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms), 2,632 grams of mineral oil and 75 grams of water, there is added, at 80100 C., 60 grams (3 equivalents) of magnesium oxide. The addition is made portionwise over a 10-minute period. The mixture is maintained at a temperature of 100- 105 C. for 3 hours. Duuring the first part of this 3-hour period, 50 grams of water is added.
  • a polyisobutenyl succinic anhydride having an acid number of 89.8 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms
  • 2,632 grams of mineral oil and 75 grams of water there is added
  • the filtrate has a magnesium content of 0.55%, based on sulfate ash, and a nitrogen content of 0.64%.
  • Example 4 To a mixture of 3,360 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 101 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 67 carbon atoms), 2,285 grams of mineral oil and 81 grams of water, there is added, at 80-95 C., 110 grams (2.9 equivalents) of calcium hydroxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 90- 105 C. for 4 hours.
  • a polyisobutenyl succinic anhydride having an acid number of 101 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 67 carbon atoms
  • Example 5 To a mixture of 3,210 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 105 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 68 carbon atoms), 2,325 grams of mineral oil and 100 grams of water, there is added, at 80-95 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a period of 15 minutes. The mixture is maintained at a temperature of 100110 C. for 4 hours.
  • a polyisobutenyl succinic anhydride having an acid number of 105 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 68 carbon atoms
  • Example 6 To a mixture of 3,330 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 89.8 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms), 2,386 grams of mineral oil and grams of water, there is added, at -85 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of -100 C. for 4.5 hours.
  • a polyisobutenyl succinic anhydride having an acid number of 89.8 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms
  • 2,386 grams of mineral oil and grams of water there is added, at -85 C., 122 grams (3 equivalents
  • Example 2 122 grams (3 equivalents) of the amine mixture described in Example 1 is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at -110 C. The mixture is heated to 205-215 C. and maintained at this temperature for an additional 4.5 hours. Throughout this 4.5-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.64% and a nitrogen content of 0.72%
  • Example 7 To a mixture of 1,028 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 109 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 65 carbon atoms), 707 grams of mineral oil and 1,500 grams of benzene, there is added at 60 C., 41 grams (1 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 41). The addition is made portionwise over a 30- minute period. The mixture is maintained at a temperature of 8590 C. for 7 hours.
  • a polyisobutenyl succinic anhydride having an acid number of 109 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 65 carbon atoms
  • 707 grams of mineral oil and 1,500 grams of benzene there is added at 60
  • Example 8 To a mixture of 3,740 grams (7.2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinate polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 2,610 grams of mineral oil, there is added at 6080 C., 220 grams (5,4 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.7). The addition is made portionwise over a 1-hour period. The mixture is maintained at a temperature of 150-155 C. for 5 hours. Throughout this 5-hour period, nitrogen is bubbled through the mixture to remove water resulting fram acylation.
  • a polyisobutenyl succinic anhydride having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinate polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms
  • Example 9 To a mixture of 2,072 grams (4 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 1,425 grams of mineral oil, there is added at 60-S0 C., 81 grams (2 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.7). The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 150- 155 C. for 5 hours. Throughout this 5-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation.
  • a polyisobutenyl succinic anhydride having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atom
  • Example 10 To a mixture of 3,620 grams (7 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 2,490 grams of mineral oil, there is added at 6080 C., 143 grams (3.5 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.7). The addition is made portionwise over a 1-hour period. The mixture is maintained at a temperature of 150-155 C. for 5 hours throughout which period nitrogen is bubbled through the mixture to remove water resulting from acylation.
  • a polyisobutenyl succinic anhydride having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms
  • mineral oil 2,490
  • Example 11 To a mixture of 3,540 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 95 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 76 carbon atoms), 2,538 grams of mineral oil and grams of water, there is added at 80 C., 208 grains (3 equivalents) of potassium carbonate. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of -l05 C.
  • Example 12 To a mixture of 4,200 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 80 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 92 carbon atoms) and 2,930 grams of mineral oil, there is added at 80 C., 390 grams of 1-(2-hydroxyethyl)piperazine. The addition is made portionwise over a 30-minute period and the resulting mixture is maintained at a temperature of 180205 C. for 5 hours. Throughout the 5-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation.
  • a polyisobutenyl succinic anhydride having an acid number of 80 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 92 carbon atoms
  • Example 13 To a mixture of 524 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 Weight percent and an average of 66 carbon atoms), 365 grams of mineral oil and 20 grams of water, there is added at 80-100 C., 21 grams (0.5 equivalent) of lithium hydroxide. The addition is made portionwise over a 15-rninute period. The mixture is maintained at a temperature of 110 C.
  • a polyisobutenyl succinic anhydride having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 Weight percent and an average of 66 carbon atoms
  • Example 14 To a mixture of 523 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 370 grams of mineral oil, there is added at 70 C., 21 grams (0.5 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.5). The addition is made portionwise over a 15-minute period whereupon 10 grams of water, and then 20 grams (0.5 equivalent) of zinc oxide,
  • the mixture is maintained at 80 C.
  • the mixture is heated first at 100-110 C. for 4 hours, then at l50l60 C. for 6 hours. Nitrogen is bubbled into the mixture throughout the 6-hour period to remove water resulting from acylation. The residue is filtered.
  • the filtrate has a zinc content of 0.84 percent and a nitrogen content of 0.80 percent.
  • Example 1 To a mixture of 5.44 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 103 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 70 carbon atoms) and 380 grams of mineral oil, there is added at -25 C., 43 grams (0.5 equivalent) of magnesium methylate. The addition is made portionwise over a -minute period. The mixture is maintained at a temperature of -75 C. for 3 hours whereupon 20.4 grams (0.5 equivalent) of an amine mixture such as described in Example 1 is added portionwise over a 30-minute period while the temperature is maintained at C. The mixture is heated at 160175 C. for 4 hours. Throughout this 4-hour period, nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a magnesium content of 0.85 percent and a nitrogen content of 0.72 percent.
  • Example 16 To a mixture of 609 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 92 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 79 carbon atoms) and 426 grams of mineral oil, there is added at 3540 C., 20.8 grams (0.5 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 41.6). The addition is made portionwise over a 30-minute period and the mixture is maintained for 5 hours thereafter at a temperature of l65180 C. Throughout this 5-hour period nitrogen is bubbled into the mixture to remove water resulting from acylation.
  • a polyisobutenyl succinic anhydride having an acid number of 92 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 79 carbon atoms
  • Example 17 To a mixture of 982 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 114 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms), 605 grams of mineral oil and 20 grams of water, there is added at 98 C., 50 grams (1 equivalent) of calcium carbonate. The addition is made portionwise over a 45-minute period and the mixture is maintained for 7.5 hours thereafter at a temperature of 120-145 C.
  • a polyisobutenyl succinic anhydride having an acid number of 114 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms
  • Example 18 To a mixture of 3,150 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms), 284 grams of mineral oil and grams of water, there is added at 80l00 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a period of 15 minutes. The mixture is maintained at a temperature of 100-110 C. for 4 hours whereupon 198 grams (3 equivalents) of an amine mixture such as described in Example 5 is added portionwise over a period of 30 minutes. The mixture is heated to 150-l60 C. and held there for 3.5 hours. Throughout this 3.5-hour period, nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.77 and a nitrogen content of 0.75%.
  • Example 19 To a mixture of 524 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms), 500 grams of toluene and 10 grams of water, there is added at 80 C., 20 grams (0.5 equivalent) of sodium hydroxide. The addition is made portionwise over a period of 15 minutes. The mixture is maintained at a temperature of 80-85 C. for 1 hour and the mixture then is dried by heating at 110-115 C. for 1 hour.
  • a polyisobutenyl succinic anhydride having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms
  • Example 20 To a mixture of 990 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms), 694 grams of mineral oil and 20 grams of water, there is added at 30 C., 69 grams (1 equivalent) of potassium carbonate. The addition is made portionwise over a period of 15 minutes. The mixture is heated at 8595 C. for 1 hour and then dried by heating at l35-145 C./50 mm. for 1 hour.
  • a polyisobutenyl succinic anhydride having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms
  • Example 21 To a mixture of 1,180 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 95 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 76 carbon atoms) and 826 grams of mineral oil, there is added at 25 C., 54 grams (1 equivalent) of sodium methylate. The addition is made portionwise over a 15-minute period and the mixture then is maintained at a temperature of 85 90 C. for 1 hour. Thereupon, 109 grams (1 equivalent) of nickel bromide is added portionwise over a period of 30 minutes at 95- 105 C., after which the mixture is heated at l45160 C. for 8 hours.
  • a polyisobutenyl succinic anhydride having an acid number of 95 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 76
  • the mixture is filtered and the filtrate treated with 66 grams (1 equivalent) of an amine mixture such as described in Example 5.
  • the addition is made portionwise over a 30-minute period while the temperature is maintained at 8085 C.
  • the mixture then is heated at 150160 C. for 3.5 hours throughout which period nitrogen is bubbled into the mixture to remove water resulting from acylation.
  • the residue is filtered.
  • the filtrate has a nickel content of 1.12% and a nitrogen content of 0.56%.
  • Example 22 To a mixture of 1,245 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 90 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms), 871 grams of mineral oil and 25 grams of water, there is added at 80 C., 56 grams (1 equivalent) of potassium hydroxide. The addition is made portionwise over a 30-minute period, after which the mixture is held at 8595 C. for 1 hour, then dried by heating at l35-140 C. for 1 hour.
  • a polyisobutenyl succinic anhydride having an acid number of 90 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms
  • Example 23 To a mixture of 1,046 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 732 grams of mineral oil, there is added at 60 C., 82 grams (1 equivalent) of sodium propylate. The addition is made portionwise over a period of 15 minutes and the mixture then is heated at 80-90 for 1.5 hours. Thereupon, 122 grams (1 equivalent) of zinc nitrate trihydrate is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 90-100 C.
  • a polyisobutenyl succinic anhydride having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms
  • the mixture then is heated at 100-105 C. for 9 hours and filtered, whereupon 66 grams (1 equivalent) of an amine mixture such as described in Example is added. The addition is made portionwise over a 30-minute period with the temperature at l10-l20 C. Finally, the mixture is heated at 150160 C. for 4 hours while nitrogen is bubbled into the mixture to remove Water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.4% and nitrogen content of 0.62%.
  • Example 24 To a mixture of 400 grams (0.81 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms) and 84 grams of toluene, there is added 19.5 grams (0.445 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 43.8). The mixture is heated at 120 C. for 2.5 hours and then is cooled to 90 C., whereupon 5 grams of water, and then 34 grams (0.44 equivalent) of barium oxide are added. The mixture then is heated at 90-100 C. for 2 hours and 298 grams of mineral oil added. The temperature is raised to 160 C. and nitrogen bubbled through until the mixture is dry. The residue is filtered. The filtrate has a barium content of 3.05 percent and a nitrogen content of 0.94 percent.
  • Example 25 To a mixture of 1,200 grams (2.42 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms) and 888 grams of mineral oil, there is added 58 grams (1.325 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 43.8). The mixture is heated at 110-12t) C. for 2 hours and then cooled to C. Next, 25 grams of water, then 102 grams (1.33 equivalents) of barium oxide are added. The mixture then is heated at -100 C. for 2 hours, then nitrogen is bubbled through at 160 C. until the mixture is dry. The residue is filtered. The filtrate has a barium content of 3.0 percent and a nitrogen content of 0.93 percent.
  • a polyisobutenyl succinic anhydride having an acid number
  • Example 26 To a mixture of 397 grams (0.8 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 Weight percent and an average of 62 carbon atoms) and grams of toluene, there is added at 54-70 C., 12 grams (0.4 equivalent) of ethylene diamine. The addition is made portionwise over a 15-minute period and the mixture then heated to 115 C. where the azeotrope of toluene and water (resulting from acylation) is collected. The residue is heated at 138 C. for 1 hour.
  • a polyisobutenyl succinic anhydride having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 Weight percent and an average of 62 carbon atoms
  • Example 27 To a mixture of 400 grams (0.81 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms) and 84 grams of toluene, there is added 19.5 grams (0.41 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 43.8). The mixture is heated at 120 C. for 2.5 hours, then cooled to 90 C. and to this mixture, 5 grams of water, and then 12.5 grams (0.45 equivalent) of calcium oxide are added. The mixture is heated at 90-100 C. for 2 hours and then diluted with 285 grams of mineral oil. The mixture is then treated with nitrogen at C. to remove the toluene and water, then filtered. The filtrate has a calcium content of 0.89% and a nitrogen content of 1.03%.
  • compositions of this invention When used as lubricant additives, the compositions of this invention are usually present in lubricating oils in amounts ranging from about 0.5% to about 20% by weight. The optimum amount of said composition depends to a large extent upon the type of service to which the lubricating composition is to be subjected.
  • lubricating compositions for use in gasoline internal combustion engines may contain from about 0.8 to about 4% by weight of the product of the invention whereas lubricating compositions for use in differential housings and diesel engines may contain as much as 15% or even more of the additive.
  • additives include, for example, detergents of the ash-containing type, detergents of the ashless-containing type, oxidation inhibiting agents, corrosion inhibiting agents, viscosity index improving agents, pour point depressing agents, extreme pressure agents, color stabilizers and anti-foam agents.
  • the ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g. polyisobutene having a molecular weight of 7505,000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
  • olefin polymer e.g. polyisobutene having a molecular weight of 7505,000
  • a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide,
  • the basic salts are those salts containing larger amounts of metal than present in stoichiometric organic acid radical salts.
  • the most common method for preparing said basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent in the present of a promoter.
  • the most common metal neutralizing agents arethose of metal oxide, hydroxide, carbonate, bicarbonate or sulfide.
  • promoters include phenolic compounds, alcohols, glycols, and amines.
  • a particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of water and carbonating the mixture at an elevated temperature such as 60-200 C.
  • Extreme pressure agents and oxidation-inhibiting and corrosion-inhibiting agents are exemplified by chlorinated aliphatic hydrocarbons, organic sulfides and polysullides, phosphosulfurized hydrocarbons, phosphorus esters including dihydrocarbons and trihydrocarbon phosphites, metal thiocarbamates and metal phosphorodithioates.
  • Pour point depressing agents are illustrated by polymers of ethylene, propylene, or isobutene and poly(alklymethacrylatcs).
  • Anti-foam agents include polymeric alkyl siloxanes, poly(alkylmethacrylates), and the condensation product of alkylphenol with formaldehyde and an amine.
  • Example B SAE 10 mineral lubricating oil containing 3.1% of the product of Example 1, 5.5% of a co-polymer of alkyl methacrylate and N-vinyl pyrrolidone, and 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of (mole) of isobutyl alcohol and 35% (mole) of mixed primary-amyl alcohols.
  • Example F SAE 30 mineral lubricating oil containing 15% of the product of Example 3, 0.12% of phosphorus as a zinc salt of a phosphorodithioic acid obtained by the reaction of phosphorus pentasulfide with iso-octyl alcohol, and 0.003% of a poly-(alkyl siloxane) anti-foam agent.
  • the utility of the dispersant additives of the invention is shown by the results and evaluation of a modified version of the CRC-EX-3 engine test (ordinarily this engine test lasts for 96 hours; the modified version lasts for 144 hours).
  • the test is recognized in the lubricating field as an important test by which lubricants can be evaluated for use under light duty service conditions.
  • a lubricant is used in the crankcase of a 1954, 6-cylinder Chevrolet Powerglide engine for 144 hours under recurring cycling conditions. Each cycle consists of the following: (A) 2 hours at an engine speed of 500-325 r.p.m.
  • the engine is dismantled and inspected for sludge and varnish in accordance with the CRC deposit rating system.
  • the rating is based on (1) the extent of piston ring-filling, (2) the amount of sludge formed in the engine (on a scale of 80-0, 80 being indicative of no sludge and 0 being indicative of extremely heavy sludge), and (3) the total amount of engine deposits, i.e., sludge and varnish, formed in the engine (on a scale of 100-0, 100 being indicative of no deposts and 0 being indicative of extremely heavy deposits).
  • the utility of the invention as a dispersant is shown by the following results:
  • Example C which showed a rating of 1% top groove filling and a total deposit rating of 94 for the 120- hour period; 9% top groove filling and a total deposit rating of 90.5 for the 360-h0ur period; and 8% top groove filling and a total deposit rating of for the 480-hour completed cycle.
  • compositions invention as an oxidation and corrosion inhibitor are shown by the results of an oxidation and bearing corrosion test (Tentative Standand Method 3405-T of Federal Test Method Standard No. 791).
  • This test involves the continuous operation of a single-cylinder CLR Oil Test Engine under constant speed, air-fuel ratio, and fuel flow conditions for a total of 40 hours. Before the test, the engine is thoroughly cleaned, pertinent measurements of engine parts are taken and a complete set of new piston rings and new copper-lead connecting rod test bearing inserts are installed.
  • the lubricant is evaluated with respect to stability or resistance to oxidation, copper-lead bearing corrosion, and a deposition of varnish and/or sludge on engine parts. The test does not evaluate the dispersant and detergent characteristics of the lubricant.
  • the lubricant is used in the crankcase of a single cylinder, 3.8" bore, 3.75" stroke, and 45.5" displacement engine for 40 hours under the following conditions:
  • the piston is rated for piston skirt varnish (on a scale of 10-0, 10 being indicative of no varnish and 0 being indicative of maximum amount of varnish) and the copper-lead bearing is evaluated for weight loss (a loss of less than 50 milligrams is indicative of a superior lubricant).
  • the utility of the composition of this invention as a corrosion and oxidation inhibitor is shown by this test with Example D and shows a piston skirt varnish rating of 9.9 and a copper-lead bearing weight loss of 18.6 milligrams.
  • a rust test i.e., modified ASTM procedure 13665-54. This test indicates the ability of lubricating oils to aid in preventing the rusting of ferrous parts should water or other corrosives become mixed with the oil. The test involves immersing a steel rod in 300 ml.
  • test lubricant containing 5 milliliters of acidified" water (prepared by dissolving 10 grams of glacial acetic acid and 10 grams of concentrated sulfuric acid per liter of water), agitating the lubricant at 140 F., removing the rod after 5 hours of testing and cleaning it by dipping in benzene and then in acetone, drying the rod, coating the rod with a clear lacquer to fix the rust, and inspecting the rod for rusting.
  • the duration of this test is 5 hours and, as indicated above, the rod is then evaluated for rust (on a scale of 10-0, 10 being indicative of no rust and 0 being indicative of extremely heavy rusting).
  • Example B which scored 10.
  • compositions of this invention as additives in lubricating compositions
  • an oxidation and detergency test is run in which a 350 cc. sample of a lubricant containing 1.5% by weight of the solvent-free additive is placed in a 2 x 15 (inches) borosilicate tube. A 1% x 5% (inches) SAE 1020 steel panel is immersed in the above oil composition. Thereupon, the sample is heated at 300 F. for 96 hours while air is bubbled through the sample at the rate of 10 liters per hour. The oxidized sample is cooled to F.,
  • the base oil of the lubricant sample employed in this test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 180 SUS at 100 F. The results of the test are indicated in the following table (Table II).
  • a process for preparing an oil-soluble nitrogen-containing metal salt composition comprising reacting, at a temperature within the range of from about 20 C. to about 250 C., (A) about two equivalents of a succinic compound selected from the class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, with (B) about one equivalent of a basic metal reactant selected from the class consisting of alkali metal, alkaline earth metal, lead, cadmium and zinc oxides, hydroxides, carbonates and lower alcoholates and the successive combination of an alkali metal hydroxide and an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel, and cobalt halides and nitrates, and subsequently with (C) from one to about five equivalents of an amine selected from the class consisting of alkylene polyamines and
  • a process for preparing an oil-soluble nitrogen-containing metal salt composition comprising reacting, at a temperature within the range of from about 60 C. to about 250 C., (A) one equivalent of a mono-metal salt of a hydrocarbon-substituted succinic acid in which the hydrocarbon substituent has at least about 50 aliphatic carbon atoms and the metal of said metal salt is a metal selected from the class consisting of alkali metal, alkaline earth metal, zinc, cadmium, nickel, cobalt and lead, with (B) from about one to about five equivalents of an amine selected from the class consisting of alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines having up to about eight carbon atoms in the alkylene radical and up to about six carbon atoms in the hydroxyalkyl substituent.
  • a process for preparing an oil-soluble nitrogen-containing metal salt composition comprising (A) mixing about two equivalents of a succinic compound selected from the class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, with [from] about one [to about five] equivalent[s] of an amine selected from the class consisting of alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines having up to about eight carbon atoms in the alkylene radical and up to about six carbon atoms in the hydroxyalkyl substituent, and heating the resulting mixture at a temperature sufiicient to etlect acylation and to form an acylated amine, and to remove the water formed thereby, and then (B) mixing said acylated amine with about one equivalent of a basic metal compound selected from the class consisting of alkali metal, alkaline earth metal
  • the mono-metal salt of a hydrocarbonsubstituted succinic acid is prepared by the double decomposition of an alkali metal succinate and an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel, and cobalt halides and nitrates.
  • hydrocarbon substituent of the succinic compound is a radical derived from a polyisobutene having a molecular weight within the range from about 700 to about 100,000.
  • a lubricating composition comprising a major proportion of a lubricating oil and from about 0.5% to about 20% by weight of the product of the process of claim 1.
  • a lubricating composition comprising a major proportion of a lubricating oil and from about 0.5% to about 20% by weight of the product of the process of claim 2.
  • a process for preparing an oil-soluble nitrogencontaining zinc salt composition comprising reacting (A) a mono-zinc salt of a polyisobutylene substituted succinic acid in which the molecular weight of the polyisobutylene radical is about 1,000, with (B) one to two equivalents of an alkylene polyamine, having up to about 8 carbon atoms in the alkylene radical at a temperature within the range of from about C. to about 250 C.
  • a lubricating composition comprising a major proportion of a lubricating oil and from about 0.5 to about 20% by Weight of the product of the process of claim 9.

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Description

United States Patent 26,433 AMIDE AND IMIDE DERIVATIVES OF METAL SALTS 0F SUBSTITUTED SUCCINIC AClDS William M. Le Suer, Cleveland, Ohio, assignor to The ldubrizol Corporation, Wiclrlifle, Ohio, a corporation of bio No Drawing. Original No. 3,163,603, dated Dec. 29, 1964,
Ser. No. 329,860, Dec. 11, 1963. Application for reissue Oct. 27, 1967, Ser. No. 689,732
12 Claims. (CI. 252-33.6)
Matter enclosed in heavy brackets I: appears in the original patent but forms no part of this reissue specification; matter printed in italics indicates the additions made by reissue.
ABSTRACT OF THE DISCLOSURE Oil-soluble metal salts of substituted succinic acid acylated aliphatic polyamines and processes for their preparation. These are exemplified by the alkali, alkaline earth, lead, cadmium, zinc, nickel and cobalt salts of polyisobutenyl-substituted succinic acid acylatea' alkylene polyamines. The salts are additives for lubricating compositions.
This invention relates to new chemical compositions and to mineral oil compositions containing the same and, more particularly, it relates to a novel class of chemical compositions which act as dispersants, detergents and oxidation and corrosion inhibitors. Still more particularly this invention relates to amide and imide derivatives of metal salts of substituted succinic acids.
The prior art has shown a need for efficient dispersants to hold in suspension products caused by oxidation or deterioration of a motor oil during service life, as well as other insoluble particles so that they do not settle out and form varnish or sludge or interfere with the lubrication or functioning of the various mechanical parts. Also, dispersants are useful to hold in suspension additives for specific purposes which would otherwise be insoluble in the mineral oil.
The prior art has shown also the need for efficient oxidation and corrosion inhibitors to prevent or reduce the de osition of lacquer or varnish-like coatings on the walls of the cylinders, piston rings, etc., and to prevent or reduce the corrosion of engine parts, bearings, etc. An example of a specific purpose served by a corrosion inhibitor is the prevention of copper-lead bearing corrosion.
It is therefore an object of this invention to provide novel compositions of matter.
It is also an object of this invention to provide compositions which are adapted for use as additives in hydrocarbon oils.
It is also an object of this invention to provide compositions which are useful as dispersants and oxidation inhibitors in lubricating compositions.
It is also an object of this invention to provide compositions which are useful as dispersants and oxidation inhibitors in hydrocarbon oils.
It is another object of this invention to provide a novel process for the preparation of compositions useful as dispersants and oxidation inhibitors.
It is another object of this invention to provide improved lubricating compositions.
These and other objects of this invention are accomplished by providing an oil-soluble nitrogen-containing metal salt composition prepared by the process which comprises reacting, at a temperature within the range of from about 20 C. to about 250 C., (A) about two equivalents of a succinic compound selected from the Re. 26,433 Reissued Aug. 6, 1968 "ice class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, (B) about one equivalent of a basic metal reactant selected from the class consisting of alkali metal, alkaline earth metal, lead, cadmium, and zinc oxides, hydroxides, carbonates and lower alcoholates and the combination of an alkali metal hydroxide and an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel, and cobalt halides and nitrates, and (C) from one to about five equivalents of an amine selected from the class consisting of alkylene polyamines and hydroxy alkyl-substituted alkylene polyamines. In the usual case from about one to about two equivalents of amine is used.
The hydrocarbon-substituted succinic compounds of the oil-soluble nitrogen-containing metal salt composi tions are readily obtainable from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon or other high molecular weight bydrocarbon containing an activating polar substituent, i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to the reaction with maleic anhydride or the acid thereof. Said reaction involves heating equivalent portions of the maleic anhydride and hydrocarbon, for example, at a temperature within the range of from about 100 C. to about 200 C. The resulting product is a hydrocarbon-substituted succinic anhydride. The succinic anhydride may be hydrolyzed to the corresponding acid by treatment with water or steam. The hydrocarbon-substituted succinic acid is preferred, for the purposes of this invention, when the basic metal reactant is reacted before the polyamine and the corresponding succinic anhydride is preferred when the polyamine is reacted before the basic metal reactant.
The principal sources of the hydrocarbon-substituted radical include the high molecular weight petroleum fractions and olefin polymers, particularly polymers of monoolcfins having from 2 to about 30 carbon atoms. The especially useful polymers are the polymers of l-monoolefins such as ethylene, propene, l-butene, isobutene, l-hexene, l-octcne, Z-methyl-l-heptene, 3-cyclohexyl-lbutene, and 2-methyl-5-propyl-1-hcxene. Polymers of medial olefins, i.e., olefins in which the olefinic linkage is not at the terminal position, are like useful. Such medial olefin polymers contemplated are those illustrated by Z-butene, S-pentene, and 4-octene, etc.
Also useful are the interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and poly-olefins. Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene, isobutene and butadienes, propene with isoprene, ethylene with piperylene, isobutene with chloroprene, isobutene with p-methyl styrene, l-hexene with 1,3-hexadiene, l-octene with l-hexene, l-heptene with l-pentane, 3-methyl-l-butene with l-octene, 3,3-dimethyl-1-pentane with l-hexene, isobutene with styrene and piperylene, etc.
The relative proportions of the mono-olefins to the other monomers in the interpolymers influence the stability and oil-solubility of the products of this invention. Thus, for reasons of oil-solubility and stability, the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about and preferably at least about on a weight basis of units derived from the aliphatic mono-olefins and no more than about 5% of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percent of olefinic linkages should be less than about 2% of the total number of carbon-to-carbon covalent linkages.
Specific examples of such interpolymers useful in this invention include the following (percent by weight): copolymer of 95% of isobutene with of styrene, terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene, terpolymer of 95% of isobutene with 2% of l-butene and 3% of l-hexene, terpolymer of of iso-butene with 20% of l-pentene and 20% of l-octene, copolymer of of l-hexene and 20% of l-heptene, terpolymer of of isobutene with 2% of cyclohexene and 8% of l-heptene, terpolymer of 90% of isobutene with 2% of cyclohexene and 8% of propene, and copolymer of 80% of ethylene and 20% of propene.
Another source of the hydrocarbon substituent radicals includes saturated aliphatic hydrocarbons derived from highly refined high molecular weight white oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymer illustrated above or high molecular weight olefinic substances.
The hydrocarbon substituent may contain polar substi'tuents provided, however, that the polar substituents are not present in proportions sufliiently large as to alter significantly the hydrocarbon character of the radical. The polar substituents contemplated are those exemplified by chloro, bromo, keto, aldehydo, ethereal, and nitro, etc. The upper limit with respect to the proportion of such polar substituents in the radical is approximately 10% based on the weight of the hydrocarbon portion of the radical.
Another important aspect of this invention is that the hydrocarbon substituent of the hydrocarbon-substituted succinic compound should be substantially saturated, i.e., at least about percent of the total number of carbonto-carbon covalent linkages are saturated linkages. An excessive proportion of unsaturated linkages renders the molecule susceptible to oxidation, deterioration, and polymerization and results in products unsuitable for use in hydrocarbon oils in many applications.
The size of the hydrocarbon substituent of the said succinic compound appears to determine the effectiveness of the additive of this invention as a dispersant in lubricating oils. It is critically important that said substituent be large, that is, that it have at least about 50 aliphatic carbon atoms in its structure. The molecular weight of the hydrocarbon substituent should be within the range of from about 700 to about 100,000. Olefin polymers having a molecular weight of from 750 to 5,000 are preferred. However, higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 are also useful and have been found to impart viscosity index improving properties to the nitrogen-containing metal salt compositions of this invention. In many instances, the use of such higher molecular weight olefin polymers is desirable.
The most common sources of these substantially aliphatic hydrocarbon substituents are the polyolefins such as polyethylene, polypropylene, polyisobutene, etc. A particularly preferred polyolefin is polyisobutene having a molecular weight of about 1,000.
The hydrocarbon-substituted succinic acids and anhydrides are especially preferred for use as the acid-producing reactant in this process for reasons of the particular effectiveness of the products obtained from such compounds as additives in hydrocarbon oils. Said succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin polymer or a chlorinated olefin polymer described hereinabove. The reaction involves heating equivalent portions of the two reactants at a temperature within the range of from about to about 200 C. The product from such a reaction is an alkenyl succinic anhydride. The alkenyl group may be hydrogenated to an alkyl group. Also, the anhydride may be hydrolyzed to the corresponding acid by treatment with Water or steam.
As indicated earlier, in lieu of the high molecular weight olefin polymers or chlorinated hydrocarbons, other CJI high molecular weight hydrocarbons containing an activating polar substituent, i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride, may be used in the above reaction for preparing the succinic compounds. Such polar substituents are illustrated by sultide, disulfide, nitro, mercaptan, bromine, ketone, and aldehyde radicals. Examples of such polar-substituted hydrocarbons include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc. Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within the range of from about 100 C. to about 200 C.
The metals of the metal salts useful in this invention are those metals selected from the class consisting of alkali metals, alkaline earth metals, zinc, cadmium, lead, cobalt, and nickel. Examples of metal compounds contemplated are the following: sodium oxide, sodium hydroxide, sodium carbonate, sodium methylate, sodium propylate, sodium pentylate, sodium phenoxide, potassium oxide, potasium hydroxide, potassium carbonate, potassium methylate, potassium pentylate, potassium phenoxide, lithium oxide, lithium hydroxide, lithium carbonate, lithium pentylate, calcium oxide, calcium hydroxide, calcium carbonate, calcium methylate, calcium ethylate, calcium propylate, calcium chloride, calcium fluoride, calcium pentylate, calcium phenoxide, calcium nitrate, barium oxide, barium hydroxide, barium carbonate, barium chloride, barium fluoride, barium methylate, barium propylate, barium pentylate, barium nitrate, magnesium oxide, magnesium hydroxide, magnesium carbonate, magnesium ethylate, magnesium propylate, magnesium chloride, magnesium bromide, barium, iodide, magnesium phenoxide, zinc oxide, zinc hydroxide, zinc carbonate, zinc methylate, zinc propylate, zinc pentylate, zinc chloride, zinc fluoride, zinc nitrate trihydrate, cadminum oxide, cadmium hydroxide, cadmium carbonate, carmium methylate, cadmium propylate, cadmium chloride, cadmium bromide, cadmium fluoride, lead oxide, lead hydroxide, lead carbonate, lead ethylate, lead pentylate, lead chloride, lead fluoride, lead iodide, lead nitrate, nickel oxide, nickel hydroxide, nickel carbonate, nickel chloride, nickel bromide, nickel fluoride, nickel methylate, nickel pentylate, nickel nitrate hexahydrate, cobalt oxide, cobalt hydroxide, cobaltous bromide, cobaltous chloride, cobalt butylate, cobaltous nitrate hexahydrate, etc. The above metal compounds are merely illustrative of those useful in this invention and the invention is not to be considered as limited to such.
The amines useful in this invention include alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines.
A preferred source of the amine group consists of alkylene polyamines conforming for the most part to the formula wherein n is an integer preferably less than about 10, A is a hydrocarbon radical or hydrogen radical or an amino hydrocarbon radical, and the alkylene radical is preferably a lower alkylene radical having less than about 8 carbon atoms. Specific amines which are contemplated are exemplified by: ethylene diamine, triethylene tetramine, propylene diamine, decamethylene diamine, octamethylene diamine, di(hepta-methylene)triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, tetraethylene hexamine, di(trimethylene) triamine, 2-heptyl-3-(Z-aminopropyl)imidazoline, 1,3-bis (2 aminoethyl)imidazoline, pyrimidine, l (2 aminopropyl) piperazine, l,4-bis(2-aminoethyl) piperazine, and Z-mcthyl-l-(2-aminobutyl) piperazine. Higher homologues such as are obtained by condensing two or more of the above'illustrated alkylene amines are likewise useful.
Hydroxyalkyl-substituted alkylene polyamines, i.e., alkylene polyamines having 1 or more hydroxyalkyl substituents on a nitrogen atom, are likewise contemplated for use within this invention. The hydroxyalkyl-substituted alkylene polyamine-s are preferably those in which the alkyl group is a lower alkyl group, i.e., having less than about 6 carbon atoms. Examples of such amines include N-(Z-hydroxyethyl)-ethylene diamine, N,N'-bis (Z-hydroxyethyl)ethylene diamine, 1-(2-hydroxyethyl)- piperazine, lower hydroxypropyl-substituted diethylene triamine, di-hydroxypropyl-substituted tetraethylene pentamine, and N-B-hydroxypropyl)tetramethylene diamine.
Higher homologues such as are obtained by condensation of the above-illustrated alkylene amines are hydroxyalkyl-substituted alkylene amines through amino radicals or through hydroxy radicals are likewise useful. It will be appreciated that condensation through amino radicals results in a higher polyamine accompanied by removal of ammonia and that condensation to the hydroxyl radicals results in products containing ether linkages accompanied by removal of water.
The ethylene polyamines are especially useful in this invention. They are described in detail under the heading Ethylene Amines in Encyclopedia of Chemical Technology, Kirk and Othmer, volume 5, pages 898- 905, Interscience Publishers, New York (1950). Such compounds are prepared by the reaction of an alkylene chloride with ammonia which results in the production of complex mixtures of alkylene polyamines, including cyclic condensation products such as piperazines. These mixtures find use in the processes of this invention. On the other hand, quite satisfactory products may be obtained also by the use of pure alkylene polyamines. An especially useful alkylene polyamine for reasons of economy as well as the effectiveness of the products derived therefrom, is a mixture of ethylene polyamines prepared by the reaction of ethylene dichloride and ammonia and having a composition which, in its elemental analysis, corresponds to that of tctraethylene pentamine.
Another especially useful amine for reasons of economy as well as the effectiveness of the products derived therefrom is a mixture of poly(trimethylene) polyamines and the 1,3-trimethylene diamine derived from the reaction of acrolein and ammonia.
The process of this invention can be carried out either by (1) first preparing the acylated amine of the hydrocarbon-substituted succinic compound and then reacting said acylated amine with the basic metal compound, or
by (2) first preparing the mono-metal salt of the hydrocarbon-substituted succinic compound and then reacting said mono-metal salt with an alkylene polyamine or hydroxyalkyl-substituted alkylene polyamine. In the first method, it is preferred that the succinic compound be the succinic anhydride and that trace amounts of water, i.e., up to about 2.5% by weight, be present when the basic metal compound is an oxide. In the second method, it is preferred that the succinic compound be the succinic acid. In all cases, it is preferred that nitrogen or some such inert gas be bubbled through the reaction mixtures to remove any water formed as a result of the acylation reaction.
The first method above involves (A) mixing a succinic compound selected from the class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, with at least about one equivalent of an amine selected from the class consisting of alkylene polyamines and bydroxyalkyl-substituted alkylene polyamines, and heating the resulting mixture to elfect acylation and to form an acylated amine, and to remove the water formed thereby, and then (B) mixing said acylated amine with about one equivalent of a basic metal compound from the class consisting of alkali metal, alkaline earth metal, zinc, cadmium and lead oxides, hydroxides, carbonates and lower alcoholates, and heating the resulting mixture at a temperature "within the range of from about 20 C. to about 250 C. It is preferred that said acylation reaction be carried out at a temperature within the range of from about 80 C. to about 160 C. and for a period of time within the range of from about 3 hours to about 5 hours.
The second variant of the process comprises reacting, at a temperature within the range of from about 60 C. to about 250 C., (A) one equivalent of a mono-metal salt of a hydrocarbon-substituted succinic acid in which the hydrocarbon substituent has at least about 50 aliphatic carbon atoms and the metal of said metal salt is selected from the class consisting of alkali metals, alkaline earth metals, zinc, cadmium, nickel, cobalt, and lead, with (B) at least about one equivalent of an amine selected from the class consisting of alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines.
The mono-metal salt may be prepared by heating at a temperature within the range of from about 80 C. to about 130 C., two equivalents of a hydrocarbon-substituted succinic acid with about one equivalent of a basic metal reactant selected from the class consisting of alkali metal, alkaline earth metal, lead, cadmium, and zinc oxides, hydroxides, carbonates and lower alcoholates, for a period of time of from about 1 hour to about 5 hours. The temperature can be as low as 20 C., although usually it should be within the range above. Also, it is preferred that the reaction of the mono-metal succinate with the amine is best carried out at a temperature within the range of from about 80 C. to about 160 C. It usually requires from about 3 to about 5 hours.
The mono-metal succinate may be prepared by double decomposition of an alkali metal succinate with an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel and cobalt halides and nitrates.
The use of a solvent such as toluene, mineral oil, etc., is sometimes desirable.
The mono-metal succinates are illustrated by the structural formula:
if (I!) R-(J-C-O-M IIC|1'COII where R is a hydrocarbon substituent having at least about 50 aliphatic carbon atoms and M is one equivalent of an alkali metal, alkaline earth metal, lead, cadmium, zinc, nickel or cobalt.
The lower alcoholates referred to in this invention are alcoholates containing from one to about 16 carbon atoms. Examples of said alcoholates include methylates, ethylates, propylates, butylates, hexylates, etc.
The following examples illustrate the process of this invention:
Example 1 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene (having an average chlorine content of 4.3 weight percent and an average of carbon atoms) with maleic anhydride at about 200 C. The resulting polyisobutenyl succinic anhydride has an acid number of 103. To a mixture of 3,264 grams (6 equivalents) of this polyisobutenyl succinic anhydride, 2,420 grams of mineral oil and grams of water, there is added at to 100 C., 122.1 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a period of 30 minutes. The mixture is maintained at a temperature of -100 C. for a period of 3 hours. Thereupon, the mixture is heated to 150 C. and maintained at this temperature until it is essentially dry. The mixture is cooled to C. and there is added 245 grams (6 equivalents) of an ethylene polyamine mixture having an average composition corresponding to that of tetraethylene pentamine and an equivalent weight of 40.8. The addition is made portionwise over a period of 30 minutes whereupon the mixture is heated to a temperature of 150160 C. and maintained at this temperature for hours. Throughout the 5-hour period, nitrogen is bubbed through the mixture to remove water formed as a result of acylation. The residue is filtered. The resulting filtrate has a zinc content of 1.63% and a nitrogen content of 1.39%.
Example 2 To a mixture of 3,330 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 101 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 71 carbon atoms), 2,386 grams of mineral oil and 75 grams of water, there is added, at 8090 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a 30-minute period. The mixture is maintaind at a temperature of 90-105 C. for 4 hours. Thereupon, 122 grams (3 equivalents) of the amine mixture described in Example 1 is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 105110 C. The mixture is heated at 205-215 C. and maintained at this temperature for 4 hours. Throughout the 4-hour period, nitrogen is bubbled through the mixture to remove water formed as a result of acylation. The residue is filtered. The resulting filtrate has a zinc content of 1.64% and a nitrogen content of 0.72%
Example 3 To a mixture of 3,750 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 89.8 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms), 2,632 grams of mineral oil and 75 grams of water, there is added, at 80100 C., 60 grams (3 equivalents) of magnesium oxide. The addition is made portionwise over a 10-minute period. The mixture is maintained at a temperature of 100- 105 C. for 3 hours. Duuring the first part of this 3-hour period, 50 grams of water is added. Thereupon, 113 grams (3 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 37.8) is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 98100 C. The mixture is heated at 210215 C.
and maintained at this temperature for 4 hours. Throughout the 4-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a magnesium content of 0.55%, based on sulfate ash, and a nitrogen content of 0.64%.
Example 4 To a mixture of 3,360 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 101 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 67 carbon atoms), 2,285 grams of mineral oil and 81 grams of water, there is added, at 80-95 C., 110 grams (2.9 equivalents) of calcium hydroxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 90- 105 C. for 4 hours. Thereupon, 114 grams (3 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 37.8) is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 105110 C. The mixture is heated to 200-230 C. and maintained at this temperature for 4 hours. Throughout the 4-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a calcium content of 3.4%, based on sulfate ash, and a nitrogen content of 0.71%.
Example 5 To a mixture of 3,210 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 105 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 68 carbon atoms), 2,325 grams of mineral oil and 100 grams of water, there is added, at 80-95 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a period of 15 minutes. The mixture is maintained at a temperature of 100110 C. for 4 hours. Thereupon, 209 grams (3.17 equivalents) of a mixture of poly(trimethylene)polyamines [comprising mostly N,N-di(3-aminopropyl)-N'(3-aminopropyl)-1,3-propane diamine and having an average molecular weight of 180 and a base number of 852] is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 110130 C. The resulting mixture is heated at 150-160 C. and maintained at this temperature for 3.5 hours. Throughout this 35-hour period nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.69% and a nitrogen content of 0.67%.
Example 6 To a mixture of 3,330 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 89.8 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms), 2,386 grams of mineral oil and grams of water, there is added, at -85 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of -100 C. for 4.5 hours. Thereupon, 122 grams (3 equivalents) of the amine mixture described in Example 1 is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at -110 C. The mixture is heated to 205-215 C. and maintained at this temperature for an additional 4.5 hours. Throughout this 4.5-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.64% and a nitrogen content of 0.72%
Example 7 To a mixture of 1,028 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 109 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 65 carbon atoms), 707 grams of mineral oil and 1,500 grams of benzene, there is added at 60 C., 41 grams (1 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 41). The addition is made portionwise over a 30- minute period. The mixture is maintained at a temperature of 8590 C. for 7 hours. Throughout this 7-hour period, nitrogen is bubbled through the mixture to remove water resutling from acylation. To 1,034 grams of the above mixture and 52 grams of water, there is added 8090 C., 52 grams (0.67 equivalent) of barium oxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 80-90 C. for 2 hours. Thereupon, the mixture is heated to C. and stripped of the last traces of water. The residue is filtered. The filtrate has a barium content of 3.9% and a nitrogen content of 0.76%.
Example 8 To a mixture of 3,740 grams (7.2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinate polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 2,610 grams of mineral oil, there is added at 6080 C., 220 grams (5,4 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.7). The addition is made portionwise over a 1-hour period. The mixture is maintained at a temperature of 150-155 C. for 5 hours. Throughout this 5-hour period, nitrogen is bubbled through the mixture to remove water resulting fram acylation. To 2,180 grams of the above mixture, 8 grams of mineral oil, and 25 grams of water, there is added at 80 C., 25 grams (0.68 equivalent) of calcium hydroxide. The addition is made portionwise over a 1-hour period. The mixture is maintained at a temperature of 80-90 C. for two hours whereupon the mixture is heated to 150 C. and stripped of the last traces of water. The residue is filtered. The filtrate has a calcium content of 0.54% and a nitrogen content of 1.2%.
Example 9 To a mixture of 2,072 grams (4 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 1,425 grams of mineral oil, there is added at 60-S0 C., 81 grams (2 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.7). The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 150- 155 C. for 5 hours. Throughout this 5-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. To 2,240 grams of the above mixture and 40 grams of water, there is added at 60 C., 39 grams (0.96 equivalent) of zinc oxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 80-90 C. for 4 hours whereupon the mixture is heated to 150 C. and stripped of the last traces of water. The residue is filtered. The filtrate has a zinc content of 1.3% and a nitrogen content of 0.84%.
Example 10 To a mixture of 3,620 grams (7 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 108 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 2,490 grams of mineral oil, there is added at 6080 C., 143 grams (3.5 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.7). The addition is made portionwise over a 1-hour period. The mixture is maintained at a temperature of 150-155 C. for 5 hours throughout which period nitrogen is bubbled through the mixture to remove water resulting from acylation. To 2,170 grams of the above mixture, 84 grams of water, and 46 grams of mineral oil, there is added at 60-80 C., 84 grams (1.1 equivalents) of barium oxide. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of 80-90 C. for 2 hours whereupon the mixture is heated to 150 C. and stripped of the last traces of water. The residue is filtered. The filtrate has a barium content of 3% and a nitrogen content of 0.76%.
Example 11 To a mixture of 3,540 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 95 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 76 carbon atoms), 2,538 grams of mineral oil and grams of water, there is added at 80 C., 208 grains (3 equivalents) of potassium carbonate. The addition is made portionwise over a 30-minute period. The mixture is maintained at a temperature of -l05 C. for 4 hours whereupon 120 grams (3 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40) is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 1101 15 C. The mixture is heated to 170- 185 C. and maintained at this temperature for 4 hours. Throughout this 4-hour period nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a potassium content of 1.56 percent and a nitrogen content of 0.70 percent.
Example 12 To a mixture of 4,200 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 80 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 92 carbon atoms) and 2,930 grams of mineral oil, there is added at 80 C., 390 grams of 1-(2-hydroxyethyl)piperazine. The addition is made portionwise over a 30-minute period and the resulting mixture is maintained at a temperature of 180205 C. for 5 hours. Throughout the 5-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. To the above mixture, combined with 35 grams of water, there is added at 30 C., 159 grams (3 equivalents) of sodium carbonate. The addition is made portionwise over a 45-minute period. The temperature is maintained at 7080 C. for 3 hours whereupon the mixture is heated to 150 C. and stripped of the last traces of water. The residue is filtered. The filtrate has a sodium content of 0.88 percent and a nitrogen content of 1.1 percent.
Example 13 To a mixture of 524 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 Weight percent and an average of 66 carbon atoms), 365 grams of mineral oil and 20 grams of water, there is added at 80-100 C., 21 grams (0.5 equivalent) of lithium hydroxide. The addition is made portionwise over a 15-rninute period. The mixture is maintained at a temperature of 110 C. for 4 hours whereupon 20.4 grams (0.5 equivalent) of an amine mixture such as described in Example 1 is added portionwise over a 30-minute period while the temperature of the mixture is maintained at 110-135 C. The mixture is heated to -160 C. and held there for 3.5 hours. Throughout the 35-hour period, nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a lithium content of 0.25 percent and a nitrogen content of 0.80 percent.
Example 14 To a mixture of 523 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 370 grams of mineral oil, there is added at 70 C., 21 grams (0.5 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 40.5). The addition is made portionwise over a 15-minute period whereupon 10 grams of water, and then 20 grams (0.5 equivalent) of zinc oxide,
are added while the mixture is maintained at 80 C. The mixture is heated first at 100-110 C. for 4 hours, then at l50l60 C. for 6 hours. Nitrogen is bubbled into the mixture throughout the 6-hour period to remove water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 0.84 percent and a nitrogen content of 0.80 percent.
Example To a mixture of 5.44 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 103 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 70 carbon atoms) and 380 grams of mineral oil, there is added at -25 C., 43 grams (0.5 equivalent) of magnesium methylate. The addition is made portionwise over a -minute period. The mixture is maintained at a temperature of -75 C. for 3 hours whereupon 20.4 grams (0.5 equivalent) of an amine mixture such as described in Example 1 is added portionwise over a 30-minute period while the temperature is maintained at C. The mixture is heated at 160175 C. for 4 hours. Throughout this 4-hour period, nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a magnesium content of 0.85 percent and a nitrogen content of 0.72 percent.
Example 16 To a mixture of 609 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 92 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 79 carbon atoms) and 426 grams of mineral oil, there is added at 3540 C., 20.8 grams (0.5 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 41.6). The addition is made portionwise over a 30-minute period and the mixture is maintained for 5 hours thereafter at a temperature of l65180 C. Throughout this 5-hour period nitrogen is bubbled into the mixture to remove water resulting from acylation. Thereupon, 63 grams (0.5 equivalent) of potassium pentylate is added over a 30-minute period while the temperature of the mixture is maintained at 6065 C. The mixture is maintained at a temperature of -95 C. for 3.5 hours. The mixture then is heated to 150 C. and stripped of the water and alcohol. The residue is filtered. The filtrate has a potassium content of 1.1 percent and a nitrogen content of 0.65 percent.
Example 17 To a mixture of 982 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 114 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms), 605 grams of mineral oil and 20 grams of water, there is added at 98 C., 50 grams (1 equivalent) of calcium carbonate. The addition is made portionwise over a 45-minute period and the mixture is maintained for 7.5 hours thereafter at a temperature of 120-145 C. Then 67 grams (1 equivalent) of an amine mixture such as described in Example 5 is added portionwise over a 30-minute period while the temperature of the mixture is maintained at 1l5-l25 C. The mixture is heated to 165-l75 C. and maintained at this temperature for 4 hours. Throughout this 4-hour period nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a calcium content of 0.9 percent and a nitrogen content of 0.71 percent.
Example 18 To a mixture of 3,150 grams (6 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms), 284 grams of mineral oil and grams of water, there is added at 80l00 C., 122 grams (3 equivalents) of zinc oxide. The addition is made portionwise over a period of 15 minutes. The mixture is maintained at a temperature of 100-110 C. for 4 hours whereupon 198 grams (3 equivalents) of an amine mixture such as described in Example 5 is added portionwise over a period of 30 minutes. The mixture is heated to 150-l60 C. and held there for 3.5 hours. Throughout this 3.5-hour period, nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.77 and a nitrogen content of 0.75%.
Example 19 To a mixture of 524 grams (1 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms), 500 grams of toluene and 10 grams of water, there is added at 80 C., 20 grams (0.5 equivalent) of sodium hydroxide. The addition is made portionwise over a period of 15 minutes. The mixture is maintained at a temperature of 80-85 C. for 1 hour and the mixture then is dried by heating at 110-115 C. for 1 hour. Then 59.3 grams (0.5 equivalent) of nickel chloride hexahydrate is added portionwise over a period of 30 minutes, at 80-90 C. This temperature is maintained for 6 hours, then the mixture is heated at C. for 6 hours. The mixture is filtered and the filtrate treated with 306 grams of mineral oil and 17.8 grams (0.44 equivalent) of an amine mixture such as described in Example 1. The resulting mixture is heated at 160 C. for 3.5 hours, during which time nitrogen is bubbled through the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a nickel content of 0.69 percent and a nitrogen content of 0.82 percent.
Example 20 To a mixture of 990 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms), 694 grams of mineral oil and 20 grams of water, there is added at 30 C., 69 grams (1 equivalent) of potassium carbonate. The addition is made portionwise over a period of 15 minutes. The mixture is heated at 8595 C. for 1 hour and then dried by heating at l35-145 C./50 mm. for 1 hour. Thereupon, grams (1 equivalent) of cobaltous nitrate hexahydrate is added portionwise over a period of 45 minutes while the temperature of the mixture is maintained at 9095 C. The mixture then is heated at l30150 C. for 9 hours and filtered. The filtrate is treated with 66 grams (1 equivalent) of an amine mixture such as described in Example 5. The addition is made portionwise over a 30- minute period while the temperature is maintained at l20125 C. The mixture is then heated at -185 C. for 4 hours throughout which period nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a cobalt content of 1.34% and a nitrogen content of 0.66%.
Example 21 To a mixture of 1,180 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 95 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 76 carbon atoms) and 826 grams of mineral oil, there is added at 25 C., 54 grams (1 equivalent) of sodium methylate. The addition is made portionwise over a 15-minute period and the mixture then is maintained at a temperature of 85 90 C. for 1 hour. Thereupon, 109 grams (1 equivalent) of nickel bromide is added portionwise over a period of 30 minutes at 95- 105 C., after which the mixture is heated at l45160 C. for 8 hours. The mixture is filtered and the filtrate treated with 66 grams (1 equivalent) of an amine mixture such as described in Example 5. The addition is made portionwise over a 30-minute period while the temperature is maintained at 8085 C. The mixture then is heated at 150160 C. for 3.5 hours throughout which period nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a nickel content of 1.12% and a nitrogen content of 0.56%.
Example 22 To a mixture of 1,245 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 90 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 81 carbon atoms), 871 grams of mineral oil and 25 grams of water, there is added at 80 C., 56 grams (1 equivalent) of potassium hydroxide. The addition is made portionwise over a 30-minute period, after which the mixture is held at 8595 C. for 1 hour, then dried by heating at l35-140 C. for 1 hour. Thereupon, 104.2 grams (1 equivalent) of barium chloride is added portionwise over a period of 30 minutes, with the temperature at 80-90 C. The mixture then is heated at 130140 C. for 9 hours, and filtered. To the filtrate there is added 41 grams (1 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 41). The addition is made portionwise over a 30-minute period, with the temperature at 110- 140 C. The mixture then is heated at 160-465 C. for 4 hours, throughout which period nitrogen is bubbled into the mixture to remove water resulting from acylation. The residue is filtered. The filtrate has a barium content of 2.7% and a nitrogen content of 0.61%.
Example 23 To a mixture of 1,046 grams (2 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 107 and prepared, as in Example 1, from maleic anhydride and chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 66 carbon atoms) and 732 grams of mineral oil, there is added at 60 C., 82 grams (1 equivalent) of sodium propylate. The addition is made portionwise over a period of 15 minutes and the mixture then is heated at 80-90 for 1.5 hours. Thereupon, 122 grams (1 equivalent) of zinc nitrate trihydrate is added portionwise over a period of 30 minutes while the temperature of the mixture is maintained at 90-100 C. The mixture then is heated at 100-105 C. for 9 hours and filtered, whereupon 66 grams (1 equivalent) of an amine mixture such as described in Example is added. The addition is made portionwise over a 30-minute period with the temperature at l10-l20 C. Finally, the mixture is heated at 150160 C. for 4 hours while nitrogen is bubbled into the mixture to remove Water resulting from acylation. The residue is filtered. The filtrate has a zinc content of 1.4% and nitrogen content of 0.62%.
Example 24 To a mixture of 400 grams (0.81 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms) and 84 grams of toluene, there is added 19.5 grams (0.445 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 43.8). The mixture is heated at 120 C. for 2.5 hours and then is cooled to 90 C., whereupon 5 grams of water, and then 34 grams (0.44 equivalent) of barium oxide are added. The mixture then is heated at 90-100 C. for 2 hours and 298 grams of mineral oil added. The temperature is raised to 160 C. and nitrogen bubbled through until the mixture is dry. The residue is filtered. The filtrate has a barium content of 3.05 percent and a nitrogen content of 0.94 percent.
Example 25 To a mixture of 1,200 grams (2.42 equivalents) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms) and 888 grams of mineral oil, there is added 58 grams (1.325 equivalents) of an amine mixture such as described in Example 1 (but with an equivalent weight of 43.8). The mixture is heated at 110-12t) C. for 2 hours and then cooled to C. Next, 25 grams of water, then 102 grams (1.33 equivalents) of barium oxide are added. The mixture then is heated at -100 C. for 2 hours, then nitrogen is bubbled through at 160 C. until the mixture is dry. The residue is filtered. The filtrate has a barium content of 3.0 percent and a nitrogen content of 0.93 percent.
Example 26 To a mixture of 397 grams (0.8 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 Weight percent and an average of 62 carbon atoms) and grams of toluene, there is added at 54-70 C., 12 grams (0.4 equivalent) of ethylene diamine. The addition is made portionwise over a 15-minute period and the mixture then heated to 115 C. where the azeotrope of toluene and water (resulting from acylation) is collected. The residue is heated at 138 C. for 1 hour. To 204 grams thereof, mixed with 200 grams of mineral oil and 4 grams of water, there is added at 70 C., 7.7 grams (0.01 equivalent) of barium oxide. This mixture is heated to C. over a 1-hour period and held at 145150 C. for 2 hours. The residue is filtered. The filtrate has a barium content of 0.4 percent and a nitrogen content of 0.79 percent.
Example 27 To a mixture of 400 grams (0.81 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 113 and prepared, as in Example 1, from maleic anhydride and a chlorinated polyisobutylene having an average chlorine content of 4.3 weight percent and an average of 62 carbon atoms) and 84 grams of toluene, there is added 19.5 grams (0.41 equivalent) of an amine mixture such as described in Example 1 (but with an equivalent weight of 43.8). The mixture is heated at 120 C. for 2.5 hours, then cooled to 90 C. and to this mixture, 5 grams of water, and then 12.5 grams (0.45 equivalent) of calcium oxide are added. The mixture is heated at 90-100 C. for 2 hours and then diluted with 285 grams of mineral oil. The mixture is then treated with nitrogen at C. to remove the toluene and water, then filtered. The filtrate has a calcium content of 0.89% and a nitrogen content of 1.03%.
When used as lubricant additives, the compositions of this invention are usually present in lubricating oils in amounts ranging from about 0.5% to about 20% by weight. The optimum amount of said composition depends to a large extent upon the type of service to which the lubricating composition is to be subjected.
For example, lubricating compositions for use in gasoline internal combustion engines may contain from about 0.8 to about 4% by weight of the product of the invention whereas lubricating compositions for use in differential housings and diesel engines may contain as much as 15% or even more of the additive.
This invention contemplates also the use of other additives with the products of this invention in lubricating compositions. Such additives include, for example, detergents of the ash-containing type, detergents of the ashless-containing type, oxidation inhibiting agents, corrosion inhibiting agents, viscosity index improving agents, pour point depressing agents, extreme pressure agents, color stabilizers and anti-foam agents.
The ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g. polyisobutene having a molecular weight of 7505,000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride. The most commonly used salts of such acids are those of sodium, potassium lithium, calcium magnesium, strontium, and barmm.
The basic salts are those salts containing larger amounts of metal than present in stoichiometric organic acid radical salts. The most common method for preparing said basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent in the present of a promoter. The most common metal neutralizing agents arethose of metal oxide, hydroxide, carbonate, bicarbonate or sulfide. Examples of promoters include phenolic compounds, alcohols, glycols, and amines. A particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of water and carbonating the mixture at an elevated temperature such as 60-200 C.
Extreme pressure agents and oxidation-inhibiting and corrosion-inhibiting agents are exemplified by chlorinated aliphatic hydrocarbons, organic sulfides and polysullides, phosphosulfurized hydrocarbons, phosphorus esters including dihydrocarbons and trihydrocarbon phosphites, metal thiocarbamates and metal phosphorodithioates.
Pour point depressing agents are illustrated by polymers of ethylene, propylene, or isobutene and poly(alklymethacrylatcs). Anti-foam agents include polymeric alkyl siloxanes, poly(alkylmethacrylates), and the condensation product of alkylphenol with formaldehyde and an amine.
The following examples are illustrative of lubricating compositions of this invention (all percentages are by weight):
Example A SAE mineral lubricating oil containing 3.1% of the product of Example 1, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 65% (mole) of isobutyl alcohol and (mole) of mixed primaryamyl alcohols, and 0.003% of a poly-(alkyl siloxane) anti-foam agent.
Example B SAE 10 mineral lubricating oil containing 3.1% of the product of Example 1, 5.5% of a co-polymer of alkyl methacrylate and N-vinyl pyrrolidone, and 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of (mole) of isobutyl alcohol and 35% (mole) of mixed primary-amyl alcohols.
Example C SAE 30 mineral lubricating oil containing 2.1% of the product of Example 2, 11% of a basic calcium sulfonate obtained by carbonating a mineral oil solution of a calcium polydodecyl-benzene sulfonate and an excess of calcium hydroxide in the presence of an aqueous alcohol, 0.08% of anthranilic acid, 2% of a basic barium sulfonate obtained by carbonating a mineral oil solution of a barium petroleum sulfonate and an excess of barium hydroxide in the presence of a phenolic compound, 2% of a calcium salt derived from the condensation of a heptylphenol, calcium hydroxide and para-formaldehyde carried out in the presence of a base and in a mineral oil solution, 0.002% of a poly-(:alkyl siloxane) anti-foam agent.
Example D SAE 30 mineral lubricating oil containing 3.1% of the product of Example 2, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 65% (mole) of isobutyl alcohol and 35% (mole) of mixed primaryamyl alcohols, and 0.003% of a poly-(alkyl siloxane) antifoam agent.
Example E SAE 20 mineral lubricating oil containing 3.3% of the product of Example 2, 0.075 of phosphorus as a zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 65% (mole) of isobutyl alcohol and 35% (mole) of mixed primary-amyl alcohols, and 0.003% of a poly-(alkyl siloxane) anti-foam agent.
Example F SAE 30 mineral lubricating oil containing 15% of the product of Example 3, 0.12% of phosphorus as a zinc salt of a phosphorodithioic acid obtained by the reaction of phosphorus pentasulfide with iso-octyl alcohol, and 0.003% of a poly-(alkyl siloxane) anti-foam agent.
Example G SAE 30 mineral lubricating oil containing 2.1% of the product of Example 5, 11% of a basic calcium sulfonate obtained by carbonating a mineral oil solution of a calcium polydodecyl-benzene sulfonate and an excess of calcium hydroxide in the presence of an aqueous alcohol, 0.075 of anthranilic acid, 2.1% of a basic barium sulfonate obtained by carbonating a mineral oil solution of a barium petroleum sulfonate and an excess of barium hydroxide in the presence of a phenolic compound, 2% of a calcium salt derived from the condensation of a heptylphenol, calcium hydroxide and para-formaldehyde carried out in the presence of a base and in a mineral oil solution, and 0.002% of a poly-(alkyl siloxane) antifoam agent.
Example H SAE 20 mineral lubricating oil containing 1.4% of the product of Example 6, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 65 (mole) of isobutyl alcohol and 35% (mole) of mixed primaryamyl alcohols, 1.2% of a barium detergent prepared by neutralizing with barium oxide, in the presence of a phenolic compound, the hydrolyzed reaction product of a polypropylene with phosphorus pentasullide, and 0.003% of a poly-(alkyl siloxane) anti-foam agent.
Example I SAE 20 mineral lubricating oil containing 3% of the product of Example 24. 0.0075 of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 65% (mole) 17 of isobutyl alcohol and 35% (mole) of mixed primary-1 amyl alcohols, and 0.003% of a poly-(alkyl siloxane) anti: foam agent.
The above lubricating compositions are merely illustrative and the scope of the present invention is not to be considered as limited by them, but is intended to include the use of all of the additives previously illustrated as well as others within the broad concept of the invention described herein.
The utility of the dispersant additives of the invention is shown by the results and evaluation of a modified version of the CRC-EX-3 engine test (ordinarily this engine test lasts for 96 hours; the modified version lasts for 144 hours). The test is recognized in the lubricating field as an important test by which lubricants can be evaluated for use under light duty service conditions. In this particular test, a lubricant is used in the crankcase of a 1954, 6-cylinder Chevrolet Powerglide engine for 144 hours under recurring cycling conditions. Each cycle consists of the following: (A) 2 hours at an engine speed of 500-325 r.p.m. under load at an oil sump temperature of 100-125 F., and an air-fuel ratio of 01:1;(B) 2 hours at an engine speed of 2500:25 r.p.m. under a load of 40 brake-horsepower at an oil sump temperature of 160-l70 F., and an air-fuel of 16:1; (C) 2 hours at an engine speed of 2500125 r.p.m. under a load of 40 brake-horsepower at an oil sump temperature of 240- 250 -F., and an air-fuel ratio of 16:1.
At the end of the test, the engine is dismantled and inspected for sludge and varnish in accordance with the CRC deposit rating system. The rating is based on (1) the extent of piston ring-filling, (2) the amount of sludge formed in the engine (on a scale of 80-0, 80 being indicative of no sludge and 0 being indicative of extremely heavy sludge), and (3) the total amount of engine deposits, i.e., sludge and varnish, formed in the engine (on a scale of 100-0, 100 being indicative of no deposts and 0 being indicative of extremely heavy deposits). The utility of the invention as a dispersant is shown by the following results:
TABLE I Percent Total Lubricant Tested Piston Sludge Deposit Rlng- Rating Rating Filling (1) Example E 77.9 06. 7 (2) Example H l 77. 3 95.1 (3) Example I 2 71. 7 90. 0
Further illustration of the usefulness of the products of this invention as dispersants in motor oils is gained from testing in a bore, single-cylinder Caterpillar Diesel test engine equipped with the EX 7999 High Speed Changeover Group and operated at a constant speed and B.t.u. input. This test is recognized in the field as an important test to determine the effect of an engine oil on ring sticking, wear, and the accumulation of piston deposits in a 480-hour endurance run. The lubricant is changed at 120-hour intervals; the test lasts 480 hours. The conditions of the testing operation are as follows:
Speed 1800-310 r.p.m. Load 40 B.H.P. Fuel (0.4% sulfur) 5850iB.t.u./min., 0.3 lbs./min.
Oil sump temperature 205i5 F. Intake air temperature 255:5 F. Intake air pressure 53.0:03" Hg abs.
test with Example C, which showed a rating of 1% top groove filling and a total deposit rating of 94 for the 120- hour period; 9% top groove filling and a total deposit rating of 90.5 for the 360-h0ur period; and 8% top groove filling and a total deposit rating of for the 480-hour completed cycle.
The utility of the composition invention as an oxidation and corrosion inhibitor is shown by the results of an oxidation and bearing corrosion test (Tentative Standand Method 3405-T of Federal Test Method Standard No. 791). This test involves the continuous operation of a single-cylinder CLR Oil Test Engine under constant speed, air-fuel ratio, and fuel flow conditions for a total of 40 hours. Before the test, the engine is thoroughly cleaned, pertinent measurements of engine parts are taken and a complete set of new piston rings and new copper-lead connecting rod test bearing inserts are installed. The lubricant is evaluated with respect to stability or resistance to oxidation, copper-lead bearing corrosion, and a deposition of varnish and/or sludge on engine parts. The test does not evaluate the dispersant and detergent characteristics of the lubricant. The lubricant is used in the crankcase of a single cylinder, 3.8" bore, 3.75" stroke, and 45.5" displacement engine for 40 hours under the following conditions:
proper fuel flow at specified airfuel ratio.
After completion of the test, the piston is rated for piston skirt varnish (on a scale of 10-0, 10 being indicative of no varnish and 0 being indicative of maximum amount of varnish) and the copper-lead bearing is evaluated for weight loss (a loss of less than 50 milligrams is indicative of a superior lubricant). The utility of the composition of this invention as a corrosion and oxidation inhibitor is shown by this test with Example D and shows a piston skirt varnish rating of 9.9 and a copper-lead bearing weight loss of 18.6 milligrams.
Further illustration of the usefulness of the products of this invention as corrosion and oxidation inhibitors is shown by the results of a rust test, i.e., modified ASTM procedure 13665-54. This test indicates the ability of lubricating oils to aid in preventing the rusting of ferrous parts should water or other corrosives become mixed with the oil. The test involves immersing a steel rod in 300 ml. of a test lubricant containing 5 milliliters of acidified" water (prepared by dissolving 10 grams of glacial acetic acid and 10 grams of concentrated sulfuric acid per liter of water), agitating the lubricant at 140 F., removing the rod after 5 hours of testing and cleaning it by dipping in benzene and then in acetone, drying the rod, coating the rod with a clear lacquer to fix the rust, and inspecting the rod for rusting. The duration of this test is 5 hours and, as indicated above, the rod is then evaluated for rust (on a scale of 10-0, 10 being indicative of no rust and 0 being indicative of extremely heavy rusting). The utility of the compositions of this invention with respect to the above test is shown by testing Example B which scored 10.
To further illustrate the utility of the compositions of this invention as additives in lubricating compositions, an oxidation and detergency test is run in which a 350 cc. sample of a lubricant containing 1.5% by weight of the solvent-free additive is placed in a 2 x 15 (inches) borosilicate tube. A 1% x 5% (inches) SAE 1020 steel panel is immersed in the above oil composition. Thereupon, the sample is heated at 300 F. for 96 hours while air is bubbled through the sample at the rate of 10 liters per hour. The oxidized sample is cooled to F.,
homogenized with 0.5% of water and allowed to stand at room temperature for 24 hours. Thereupon, the sample is filtered through two layers of No. 1 Whatman filter paper 20 mm. Hg pressure. The precipitate is Washed with naphtha and dried and is then weighed. The resulting weight is taken as a measure of the effectiveness of the additive to inhibit oxidation and disperse the sludge formed during the test. The greater the weight of the precipitate the less effective the additive. The base oil of the lubricant sample employed in this test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 180 SUS at 100 F. The results of the test are indicated in the following table (Table II).
TABLE II Product of Sludge (mg. per 100 this invention: cc. of sample) None 800-1200 Product of Example 3 27.4 Product of Example 7 10.4 Product of Example 9 6 Product of Example 11 102 What is claimed is:
l. A process for preparing an oil-soluble nitrogen-containing metal salt composition comprising reacting, at a temperature within the range of from about 20 C. to about 250 C., (A) about two equivalents of a succinic compound selected from the class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, with (B) about one equivalent of a basic metal reactant selected from the class consisting of alkali metal, alkaline earth metal, lead, cadmium and zinc oxides, hydroxides, carbonates and lower alcoholates and the successive combination of an alkali metal hydroxide and an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel, and cobalt halides and nitrates, and subsequently with (C) from one to about five equivalents of an amine selected from the class consisting of alkylene polyamines and hydroxyalkylsubstituted alkylene polyamines having up to about eight carbon atoms in the alkylene radical and up to about six carbon atoms in the hydroxyalkyl substituent.
2. A process for preparing an oil-soluble nitrogen-containing metal salt composition comprising reacting, at a temperature within the range of from about 60 C. to about 250 C., (A) one equivalent of a mono-metal salt of a hydrocarbon-substituted succinic acid in which the hydrocarbon substituent has at least about 50 aliphatic carbon atoms and the metal of said metal salt is a metal selected from the class consisting of alkali metal, alkaline earth metal, zinc, cadmium, nickel, cobalt and lead, with (B) from about one to about five equivalents of an amine selected from the class consisting of alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines having up to about eight carbon atoms in the alkylene radical and up to about six carbon atoms in the hydroxyalkyl substituent.
3. A process for preparing an oil-soluble nitrogen-containing metal salt composition comprising (A) mixing about two equivalents of a succinic compound selected from the class consisting of hydrocarbon-substituted succinic acids and hydrocarbon-substituted succinic anhydrides wherein the hydrocarbon substituent has at least about 50 aliphatic carbon atoms, with [from] about one [to about five] equivalent[s] of an amine selected from the class consisting of alkylene polyamines and hydroxyalkyl-substituted alkylene polyamines having up to about eight carbon atoms in the alkylene radical and up to about six carbon atoms in the hydroxyalkyl substituent, and heating the resulting mixture at a temperature sufiicient to etlect acylation and to form an acylated amine, and to remove the water formed thereby, and then (B) mixing said acylated amine with about one equivalent of a basic metal compound selected from the class consisting of alkali metal, alkaline earth metal, zinc, cadmium and lead oxides, hydroxides, carbonates and lower alcoholates, and heating the resulting mixture at a temperature within the range of from about 20 C. to about 250 C.
4. The process of claim 2 wherein the mono-metal salt of a hydrocarbonsubstituted succinic acid is prepared by the double decomposition of an alkali metal succinate and an inorganic metal salt selected from the class consisting of alkaline earth metal, lead, cadmium, zinc, nickel, and cobalt halides and nitrates.
5. The process of claim 2 wherein the hydrocarbon substituent of the succinic compound is a radical derived from a polyisobutene having a molecular weight within the range from about 700 to about 100,000.
6. The process of claim 2 wherein the amine is a polyethylene polyamine.
7. A lubricating composition comprising a major proportion of a lubricating oil and from about 0.5% to about 20% by weight of the product of the process of claim 1.
8. A lubricating composition comprising a major proportion of a lubricating oil and from about 0.5% to about 20% by weight of the product of the process of claim 2.
9. A process for preparing an oil-soluble nitrogencontaining zinc salt composition comprising reacting (A) a mono-zinc salt of a polyisobutylene substituted succinic acid in which the molecular weight of the polyisobutylene radical is about 1,000, with (B) one to two equivalents of an alkylene polyamine, having up to about 8 carbon atoms in the alkylene radical at a temperature within the range of from about C. to about 250 C.
10. A lubricating composition comprising a major proportion of a lubricating oil and from about 0.5 to about 20% by Weight of the product of the process of claim 9.
11. The product of the process of claim 1.
12. The product of the process of claim 9.
References Cited The following references, cited by the Examiner, are of record in the patented file of this patent or the original patent.
UNITED STATES PATENTS 3,018,250 l/l962 Anderson et al. 252-5l.5 3,018,291 1/1962 Anderson et al. 25251.5 X 3,087,936 4/1963 Le Suer 252-51.5 X
PATRICK P. GARVIN, Primary Examiner.
US26433D 1963-12-11 Amide and imide derivatives of metal salts of substituted succinic acids Expired USRE26433E (en)

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Cited By (145)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539513A (en) * 1967-05-16 1970-11-10 Britannic Petroleum Co Ltd The Lubricant additive
US4502971A (en) * 1982-03-24 1985-03-05 Exxon Research & Engineering Co. Concentrates of lubricant additives
US4637886A (en) 1982-12-27 1987-01-20 Exxon Research & Engineering Co. Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
US4834892A (en) 1985-10-03 1989-05-30 Elf France Additives for lubricating oils, their process of preparation and lubricating compositions containing them
US4866141A (en) 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same
US4954277A (en) 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
US4956108A (en) 1987-07-29 1990-09-11 Mobil Oil Corporation Copper salts of thiodipropionic acid derivatives as antioxidant additives process of making the same and fuel composition thereof
US5043083A (en) * 1988-06-16 1991-08-27 Exxon Chemical Patents, Inc. Method for preparing salts of polyolefinic substituted dicarboxylic acids in oleaginous mixtures of reduced viscosity
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5444135A (en) * 1992-12-17 1995-08-22 Exxon Chemical Patents Inc. Direct synthesis by living cationic polymerization of nitrogen-containing polymers
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
EP0713907A2 (en) 1994-09-26 1996-05-29 Ethyl Petroleum Additives Limited Zinc additives of enhanced performance capabilities
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5629434A (en) 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Functionalization of polymers based on Koch chemistry and derivatives thereof
EP0778333A2 (en) 1995-11-09 1997-06-11 The Lubrizol Corporation Carboxylic compositions, derivatives, lubricants, fuels and concentrates
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
US5646332A (en) 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5650536A (en) 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5767046A (en) 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
US5811379A (en) * 1996-06-17 1998-09-22 Exxon Chemical Patents Inc. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
US6066603A (en) 1996-06-17 2000-05-23 Exxon Chemical Patents Inc. Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US6147036A (en) 1996-08-08 2000-11-14 The Lubrizol Corporation Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives and derivatives thereof
US6172015B1 (en) 1997-07-21 2001-01-09 Exxon Chemical Patents, Inc Polar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof
US6403725B1 (en) 1999-08-20 2002-06-11 The Lubrizol Corporation Metal containing dispersant polymers from condensation of polymers containing acidic group with overbased compositions containing reactive nucleophilic group
US20020072558A1 (en) * 2000-12-08 2002-06-13 University Sains Malaysia Rubber derivatives and method for their preparation
US20040147410A1 (en) * 2003-01-15 2004-07-29 Milner Jeffrey L Extended drain, thermally stable, gear oil formulations
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
EP1652910A2 (en) 1994-10-17 2006-05-03 The Lubrizol Corporation Overbased metal salts useful as additives for fuels and lubricants
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20070000745A1 (en) * 2005-06-30 2007-01-04 Cameron Timothy M Methods for improved power transmission performance
US20070004603A1 (en) * 2005-06-30 2007-01-04 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US20070042916A1 (en) * 2005-06-30 2007-02-22 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US20080015124A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant composition
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Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1054093A (en) * 1963-06-17
US3346493A (en) * 1963-12-26 1967-10-10 Lubrizol Corp Lubricants containing metal complexes of alkenyl succinic acid-amine reaction product
GB1068547A (en) * 1963-12-26 1967-05-10 Exxon Research Engineering Co Metal carbonate overbased lubricant detergent-dispersants
US3306908A (en) * 1963-12-26 1967-02-28 Lubrizol Corp Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds
GB1052380A (en) * 1964-09-08
US3281357A (en) * 1964-12-02 1966-10-25 Lubrizol Corp Process for preparing nitrogen and aluminum containing compositions
US3492229A (en) * 1966-08-26 1970-01-27 Monsanto Co Functional fluid compositions
US3490737A (en) * 1966-08-26 1970-01-20 Monsanto Co Functional fluid compositions
US3454496A (en) * 1967-01-17 1969-07-08 Shell Oil Co Lubricant compositions
GB1121578A (en) * 1967-11-06 1968-07-31 Lubrizol Corp Reaction products of high molecular weight hydrocarbon succinic acid compounds, amines and heavy metal compounds
US3666662A (en) * 1970-04-23 1972-05-30 Chevron Res Alkali metal succinamate compositions for lubricating oils
US4012330A (en) * 1975-02-10 1977-03-15 Exxon Research & Engineering Co. Lithium salts of hydrocarbon substituted amic acid as low ash rust inhibitors
USRE32235E (en) * 1976-04-29 1986-08-26 The Lubrizol Corporation Magnesium-containing complexes, method for their preparation, and compositions containing the same
US4200544A (en) * 1976-04-29 1980-04-29 The Lubrizol Corporation Magnesium-containing greases and method for their preparation
US4253976A (en) * 1979-02-21 1981-03-03 The Lubrizol Corporation Magnesium oxide-carboxylate complexes, method for their preparation, and compositions containing the same
US4260500A (en) * 1979-02-21 1981-04-07 The Lubrizol Corporation Magnesium-containing complexes, method for their preparation, and compositions containing the same
JPS6079012A (en) * 1983-10-06 1985-05-04 Nippon Zeon Co Ltd Production of water-soluble dicarboxylic acid imide compound
DE3572344D1 (en) * 1984-02-09 1989-09-21 Lubrizol Corp Process for making substituted carboxylic acids and derivatives thereof
US4774345A (en) * 1985-03-21 1988-09-27 Engelhard Corporation Amine-complexed zinc salts of organic diacids
US4626283A (en) * 1985-03-21 1986-12-02 Engelhard Corporation Corrosion and marine growth inhibiting compositions
CA1281706C (en) * 1985-10-25 1991-03-19 Reed H. Walsh Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines
US4997594A (en) * 1985-10-25 1991-03-05 The Lubrizol Corporation Compositions, concentrates, lubricant compositions, fuel compositions and methods for improving fuel economy of internal combustion engines
US4780111A (en) 1985-11-08 1988-10-25 The Lubrizol Corporation Fuel compositions
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof
GB8916447D0 (en) * 1989-07-19 1989-09-06 Ici Plc Composition,process and use
US5075019A (en) * 1989-12-14 1991-12-24 Exxon Chemical Patents Inc. Low sediment method for preparing copper salts of polyolefinic-substituted dicarboxylic acids
US5232616A (en) * 1990-08-21 1993-08-03 Chevron Research And Technology Company Lubricating compositions
US5221491A (en) * 1991-08-09 1993-06-22 Exxon Chemical Patents Inc. Two-cycle oil additive
US5330667A (en) * 1992-04-15 1994-07-19 Exxon Chemical Patents Inc. Two-cycle oil additive
US5304315A (en) * 1992-04-15 1994-04-19 Exxon Chemical Patents Inc. Prevention of gel formation in two-cycle oils
GB2284815B (en) * 1993-12-14 1997-09-10 Ethyl Petroleum Additives Ltd Dispersants for lubricating oil
US5562867A (en) * 1993-12-30 1996-10-08 Exxon Chemical Patents Inc Biodegradable two-cycle oil composition
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US7182795B2 (en) * 2002-03-13 2007-02-27 Atton Chemical Intangibles Llc Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same
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ES2955555T3 (en) 2006-04-24 2023-12-04 Lubrizol Corp Turbine lubrication method using star polymers
US20080299057A1 (en) * 2007-05-29 2008-12-04 Samuel Qcheng Sun Lin Method and compositions for dispersing particulate solids in oil
KR20160128406A (en) 2014-03-05 2016-11-07 더루우브리졸코오포레이션 Emulsifier components and methods of using the same
US20160272915A1 (en) 2015-03-18 2016-09-22 The Lubrizol Corporation Lubricant compositions for direct injection engines
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US11214753B2 (en) 2020-01-03 2022-01-04 Afton Chemical Corporation Silicone functionalized viscosity index improver

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL124306C (en) * 1959-08-24
US3087936A (en) * 1961-08-18 1963-04-30 Lubrizol Corp Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound

Cited By (185)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539513A (en) * 1967-05-16 1970-11-10 Britannic Petroleum Co Ltd The Lubricant additive
US4502971A (en) * 1982-03-24 1985-03-05 Exxon Research & Engineering Co. Concentrates of lubricant additives
US4637886A (en) 1982-12-27 1987-01-20 Exxon Research & Engineering Co. Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
US4834892A (en) 1985-10-03 1989-05-30 Elf France Additives for lubricating oils, their process of preparation and lubricating compositions containing them
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
US4866141A (en) 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same
US4954277A (en) 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
US4956108A (en) 1987-07-29 1990-09-11 Mobil Oil Corporation Copper salts of thiodipropionic acid derivatives as antioxidant additives process of making the same and fuel composition thereof
US5043083A (en) * 1988-06-16 1991-08-27 Exxon Chemical Patents, Inc. Method for preparing salts of polyolefinic substituted dicarboxylic acids in oleaginous mixtures of reduced viscosity
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5650536A (en) 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5629434A (en) 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Functionalization of polymers based on Koch chemistry and derivatives thereof
US5629394A (en) * 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Direct synthesis by living cationic polymerization of nitrogen-containing polymers
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
US5646332A (en) 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5444135A (en) * 1992-12-17 1995-08-22 Exxon Chemical Patents Inc. Direct synthesis by living cationic polymerization of nitrogen-containing polymers
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5663130A (en) * 1992-12-17 1997-09-02 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5696064A (en) 1992-12-17 1997-12-09 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5698722A (en) 1992-12-17 1997-12-16 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5703256A (en) 1992-12-17 1997-12-30 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5717039A (en) 1992-12-17 1998-02-10 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US6030930A (en) 1992-12-17 2000-02-29 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives
US5767046A (en) 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
EP0713907A2 (en) 1994-09-26 1996-05-29 Ethyl Petroleum Additives Limited Zinc additives of enhanced performance capabilities
EP1652910A2 (en) 1994-10-17 2006-05-03 The Lubrizol Corporation Overbased metal salts useful as additives for fuels and lubricants
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
EP0778333A2 (en) 1995-11-09 1997-06-11 The Lubrizol Corporation Carboxylic compositions, derivatives, lubricants, fuels and concentrates
US5811379A (en) * 1996-06-17 1998-09-22 Exxon Chemical Patents Inc. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US6066603A (en) 1996-06-17 2000-05-23 Exxon Chemical Patents Inc. Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US6468948B1 (en) 1996-06-17 2002-10-22 Infineum Usa L.P. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US6147036A (en) 1996-08-08 2000-11-14 The Lubrizol Corporation Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives and derivatives thereof
US6172015B1 (en) 1997-07-21 2001-01-09 Exxon Chemical Patents, Inc Polar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof
US6403725B1 (en) 1999-08-20 2002-06-11 The Lubrizol Corporation Metal containing dispersant polymers from condensation of polymers containing acidic group with overbased compositions containing reactive nucleophilic group
US6743866B2 (en) * 2000-12-08 2004-06-01 Universiti Sains Malaysia Rubber derivatives and method for their preparation
US20020072558A1 (en) * 2000-12-08 2002-06-13 University Sains Malaysia Rubber derivatives and method for their preparation
EP2284248A2 (en) 2002-07-16 2011-02-16 The Lubrizol Corporation Slow release lubricant additives gel
EP2460870A1 (en) 2002-10-04 2012-06-06 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2436753A1 (en) 2002-10-04 2012-04-04 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2366762A1 (en) 2002-10-04 2011-09-21 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
US20040147410A1 (en) * 2003-01-15 2004-07-29 Milner Jeffrey L Extended drain, thermally stable, gear oil formulations
US7888299B2 (en) 2003-01-15 2011-02-15 Afton Chemical Japan Corp. Extended drain, thermally stable, gear oil formulations
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US20070054813A1 (en) * 2003-09-25 2007-03-08 Chip Hewette Boron free automotive gear oil
US20080009426A1 (en) * 2003-11-10 2008-01-10 Iyer Ramnath N Lubricant Compositions and Methods Comprising Dispersant and Detergent
US9267093B2 (en) 2003-11-10 2016-02-23 Afton Chemical Corporation Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
EP2230292A1 (en) 2003-11-10 2010-09-22 Afton Chemical Corporation Methods of lubricating transmissions
US20100279901A1 (en) * 2003-11-10 2010-11-04 Iyer Ramnath N Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
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US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20070000745A1 (en) * 2005-06-30 2007-01-04 Cameron Timothy M Methods for improved power transmission performance
US20070042916A1 (en) * 2005-06-30 2007-02-22 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US20070004603A1 (en) * 2005-06-30 2007-01-04 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US7902133B2 (en) 2006-07-14 2011-03-08 Afton Chemical Corporation Lubricant composition
US7879775B2 (en) 2006-07-14 2011-02-01 Afton Chemical Corporation Lubricant compositions
US20080015124A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant composition
US7833953B2 (en) 2006-08-28 2010-11-16 Afton Chemical Corporation Lubricant composition
WO2010099136A1 (en) 2009-02-26 2010-09-02 The Lubrizol Corporation Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant
EP2431448A1 (en) 2009-02-26 2012-03-21 The Lubrizol Corporation Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant
WO2011022266A2 (en) 2009-08-18 2011-02-24 The Lubrizol Corporation Lubricating composition containing an antiwear agent
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WO2011022245A1 (en) 2009-08-18 2011-02-24 The Lubrizol Corporation Lubricating composition containing an antiwear agent
WO2011022317A1 (en) 2009-08-18 2011-02-24 The Lubrizol Corporation Lubricating composition containing an antiwear agent
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WO2011075403A1 (en) 2009-12-14 2011-06-23 The Lubrizol Corporation Lubricating composition containing an antiwear agent
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WO2011075401A1 (en) 2009-12-14 2011-06-23 The Lubrizol Corporation Lubricating composition containing a nitrile compound
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WO2012030590A1 (en) 2010-08-31 2012-03-08 The Lubrizol Corporation Lubricating composition containing an antiwear agent
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US3163603A (en) 1964-12-29
DE1570869C3 (en) 1978-09-14

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