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US3746645A - Polyether series synthetic lubricating oil compositions - Google Patents

Polyether series synthetic lubricating oil compositions Download PDF

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US3746645A
US3746645A US00202652A US3746645DA US3746645A US 3746645 A US3746645 A US 3746645A US 00202652 A US00202652 A US 00202652A US 3746645D A US3746645D A US 3746645DA US 3746645 A US3746645 A US 3746645A
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glycol
lubricating oil
ether
polyether
oil
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M Saito
K Minagawa
Y Tanizaki
K Furuta
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NOF Corp
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Nippon Oil and Fats Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic 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
    • C07D207/30—Heterocyclic 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
    • C07D207/34—Heterocyclic 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

Definitions

  • polyethers Illustrative of the polyethers is butoxypolyoxypropylene No Drawing. Filed Nov. 26, 1971, Ser. No. 202,652 glycol having a mplecular i t of 500 to 3,000 9 Claims priority, application Japan, D 4. 1970, tamed by the addl'tlOl'l polymerization of propylene ox1de 45/107,264 and butanol and further alkoxypolyoxypropylene glycol Int. Cl. 010m 3/30 obtained by using the aliphatic alcohols, such as meth- U.S. Cl.
  • alkoxypolyoxyethyleneoxypropylene glycol, alkoxypolyoxypro- 5 pyleneoxybutylene glycol, alkoxypolyoxyethyleneoxypropyleneoxybutylene glycol, butoxypolyoxypropylene glycol mono ether having the above described hydrocarbon groups may be cited.
  • the present invention relates to lubricating oil com- Polyether N-arnine substituted succinimides have the positions obtained by compounding a polyether N-amine following formula.
  • Lubricating oil composition for an engine oil is obtained by adding a polyoxyalkylene glycol ether N-amine substituted succinimide to a polyoxyalkylene glycol ether.
  • R R R x, y, z and n have lubricating oil.
  • R' is Polyoxyalkylene glycol ethers (abridged as polyether C H J (m is an integer of 1 to 18), R is C H (g hereinafter) have been broadly used as in petroleum series is 0 or an inte er of 1 to 15) and R is hydrogen or a lubricating oil but have not been suitable for engine oil hydrocarbon group of CgH2g+1 (f is 0 or an integer of 1 of motorcars. This is because the additives compatible to 40 to 3) and p and s are an integer of 1 to 6.
  • the polyethers have not been fully developed as compared As the dispersant for petroleum series lubricating oil, with the petroleum series lubricating oil. Accordingly, alkenyl succini id h b k o b t th bwhen the polyethers containing no detergent or dispersant stances are not at all dissolved in the polyethers or even are used for an engine Oil O mOtOrCaTS, hey are poor in if dissolved, these substances have no excellent cleaning the function for dispersing completely carbon, varnish and and dispersing ability.
  • the compounds slag formed by the incomplete combustion of fuel into the having the above Formula 2 are different from the oil and such substances deposit on piston ring groove or alkenylsuccinimides and have a compatibility with the clog the oil filter resulting into an interference of the polyethers and a high cleaning and dispersing ability. driving of engine.
  • the amount of the compounds having the above For- The inventors have found that when the polyether mula 2 added based on the polyethers is CHI-10%. (by series lubricating oils are used as a lubricating oil of weight), preferably (LS-5% by weight.
  • an internal combustion engine for example, an engine the activity is low, while even if more than 10% is added, oil of motorcars, the excellent lubricating activity can the property is not very improved.
  • the compounds having the above Formula 2 include invention which has a high compatibility and does not alkoxypolyoxyalkylene glycol monoallyl ether N-amine form ashes, to the polyether and accomplished the present substituted succinimide, alkoxypolyoxyalkylene glycol 8- invention.
  • the polyethers having a viscosity of a lubricating oil alkoxypolyoxyalkylene glycols are the compounds cited have the following formula. in the Composition 1 of the polyethers of the base oil.
  • the polyether N-amine substituted succinimides R .fl H H OLZQH CH QLLCH QH O (PASI) having the above Formula 2 are produced in the L ⁇ l )A I I i following manner.
  • olefin ether of alkoxypolyoxyalkylene glycol is reacted with maleic anhydride and then with a poly- R and R are hydrogen or hydrocarbon groups of amine to f i i m 2m+1 0T k 2k1: a R3 and 4 re hy rogen or
  • the above described olefin ethers are produced in the fvllkyl g p of J 2 +1, m 18 an integef 0f 1 t0 k following manner.
  • Alkoxypolyoxyalkylene glycol is added 15 Integer 0f 3 t0 1' is all Integer 0f 1 and with metallic sodium or sodium methylate (CH ONa) x, y, z and n are 0 or an integer of 1 to 100. to convert the end OH group into ONa, to which a
  • the polyethers having the above Formula 1 are obmonohaloolefin is reacted.
  • the monohaloolefin has the tained by subjecting to an addition polymerization profollowing formula.
  • the unreacted polyamine and the solvent are dis- I tilled off to obtain the product.
  • the polvammes have the following formula In the above formula, X is chlorine, bromine or iodine HQN CH -NH H and R and R have the same meanings as described L ⁇ (8) above.
  • Illustrative of the monohaloolefin is allyl chloride and include ethylenediamine, diethylenetriamine, triethyland B-methallyl chloride. enetetramine, tetraethylenepentamine, trimethylenedi- For example, butoxypolyoxypropylene glycol is reacted amine and tetramethylenediamine.
  • EXAMPLE 1 7 Nae 100 parts of butoxypolyoxypropylene glycol allyl ether CH; (5) having a molecular weight of about 1,000 is added with Alternatively, an alcohol having the following Formula 6 105 Parts of maleic anhydride and Parts P y OH D (ditert.-butyl peroxide, made by Nippon 0118 and Fats 40 Co., Ltd.) and the resulting mixture was reacted at 180- 1 190 C.
  • an alcohol having the following Formula 6 105 Parts of maleic anhydride and Parts P y OH D (ditert.-butyl peroxide, made by Nippon 0118 and Fats 40 Co., Ltd.) and the resulting mixture was reacted at 180- 1 190 C.
  • butoxypolyoxypropylene is polymerized with alkylene oxides and then the end OH glycol allyl ether succinic anhydride in a reaction ratio of group is reacted with alkylmonochloride (R' X) to .form more than 95%.
  • alkylmonochloride R' X
  • an alkylethe 110 parts of said succinic anhydride is dissolved in 130 1 mole of the olefin ether having the above Formula 5 parts of xylol and 10.5 parts of tetraethylenepentamine is is reacted with 1-7 moles, preferably l-3 moles of maleic added dropwise thereto at 160 C. in 2 hours.
  • the reacanhydride at a temperature of ISO-230 C., preferably tion mixture is cured for 3 hours and then xylol and the 180-200 C. for 5-20 hours. unreacted polyamine are distilled olf to obtain 120 parts 0 of butoxypolyoxypropylene glycol allyl ether succinimide.
  • EXAMPLE 3 Less than 2% by weight of organic peroxide may be The reaction is effected in the same manner as described added as the reaction catalyst.
  • the reacpropyleneoxybutylene glycol allyl ether (molar ratio of tion may be effected in gaseous nitrogen by adding EOzPOzBO; 1:821) having a molecular weight of about xylol, toluene and the like as a diluting solvent.
  • Sample oil A, B, C, D of the Table 1 fuel: L.P.G. Standard of exchange, 30,000 kin/3 months.
  • n is an integer of l-100, (Ll-10% by weight of a polyoxyalkylene glycol ether N-amine substitutcd succinimide having the following formula R O CH CHO CH CHO CH CHO L i. M l, M i, )1
  • NorE.Isopro water means a solution of 10 g. of sample dissolved in 60 ml. of a mixture of isopropyl alcohol and water (mixture ratio of isopropyl alcohol to water is 10:6 by volume).
  • R R R x, y, z and n have the same meanings as described above, R' is C H i (m is an integer of 1-18), R is C,;H;, (g is 0 or an integer of 1-15), R is hydrogen or a hydrocarbon group of C H (f is 0 or an integer of 1-3) and p and s are an integer of 1-6.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

LUBRICANTING OIL COMPOSITION FOR AN ENGINE OIL IS OBTAINED BY ADDING A POLYOXYALKYLENE GLYCOL ETHER N-AMINE SUBSTITUTED SUCCINIMIDE TO A POLYOXYALKYLENE GLYCOL ETHER.

Description

r: 3,746,645 Ice Patented July 17, 1973 3,746,645 pylene oxide or butylene oxide alone and an aliphatic POLYETHER SE SYNTHETIC LUBRICATING alcohol (ROH) or subjecting to a random or block-co- GIL QOMPOSITIPNS polymerization two or more these oxides or ethylene oxide Masahim Sam), sagamlhara Yoshlhar Tamzakl Kama simultaneously and said alcohol and if necessary, the end kura, and Keiichi Furuta and Kenichiro Minagawa, Kawasaki, Japan, assignors to Nippon 011s and Fats 5 Company Limited, Tokyo, Japan OH group may be alkyl etherified.
Illustrative of the polyethers is butoxypolyoxypropylene No Drawing. Filed Nov. 26, 1971, Ser. No. 202,652 glycol having a mplecular i t of 500 to 3,000 9 Claims priority, application Japan, D 4. 1970, tamed by the addl'tlOl'l polymerization of propylene ox1de 45/107,264 and butanol and further alkoxypolyoxypropylene glycol Int. Cl. 010m 3/30 obtained by using the aliphatic alcohols, such as meth- U.S. Cl. 252-515 A 4 Claims anol, ethanol, propanol, 2-ethyl-hexanol, Ziegler alcohol and oxo alcohol known as derivatives of petroleum chem- ABSTRACT OF THE DISCLOSURE istry and the like, may be mentioned. In addition, alkoxypolyoxyethyleneoxypropylene glycol, alkoxypolyoxypro- 5 pyleneoxybutylene glycol, alkoxypolyoxyethyleneoxypropyleneoxybutylene glycol, butoxypolyoxypropylene glycol mono ether having the above described hydrocarbon groups may be cited. The present invention relates to lubricating oil com- Polyether N-arnine substituted succinimides have the positions obtained by compounding a polyether N-amine following formula.
Lubricating oil composition for an engine oil is obtained by adding a polyoxyalkylene glycol ether N-amine substituted succinimide to a polyoxyalkylene glycol ether.
substituted succinimide to a polyether series synthetic In the above formula, R R R x, y, z and n have lubricating oil. the same meanings as in the above Formula 1, R' is Polyoxyalkylene glycol ethers (abridged as polyether C H J (m is an integer of 1 to 18), R is C H (g hereinafter) have been broadly used as in petroleum series is 0 or an inte er of 1 to 15) and R is hydrogen or a lubricating oil but have not been suitable for engine oil hydrocarbon group of CgH2g+1 (f is 0 or an integer of 1 of motorcars. This is because the additives compatible to 40 to 3) and p and s are an integer of 1 to 6. the polyethers have not been fully developed as compared As the dispersant for petroleum series lubricating oil, with the petroleum series lubricating oil. Accordingly, alkenyl succini id h b k o b t th bwhen the polyethers containing no detergent or dispersant stances are not at all dissolved in the polyethers or even are used for an engine Oil O mOtOrCaTS, hey are poor in if dissolved, these substances have no excellent cleaning the function for dispersing completely carbon, varnish and and dispersing ability. On the contrary, the compounds slag formed by the incomplete combustion of fuel into the having the above Formula 2 are different from the oil and such substances deposit on piston ring groove or alkenylsuccinimides and have a compatibility with the clog the oil filter resulting into an interference of the polyethers and a high cleaning and dispersing ability. driving of engine. The amount of the compounds having the above For- The inventors have found that when the polyether mula 2 added based on the polyethers is CHI-10%. (by series lubricating oils are used as a lubricating oil of weight), preferably (LS-5% by weight. In less than 0.1% an internal combustion engine, for example, an engine the activity is low, while even if more than 10% is added, oil of motorcars, the excellent lubricating activity can the property is not very improved. be attained by compounding the dispersant of the present The compounds having the above Formula 2 include invention which has a high compatibility and does not alkoxypolyoxyalkylene glycol monoallyl ether N-amine form ashes, to the polyether and accomplished the present substituted succinimide, alkoxypolyoxyalkylene glycol 8- invention. methallyl ether N-substituted succinimide and the like and The polyethers having a viscosity of a lubricating oil alkoxypolyoxyalkylene glycols are the compounds cited have the following formula. in the Composition 1 of the polyethers of the base oil.
The polyether N-amine substituted succinimides R .fl H H OLZQH CH QLLCH QH O (PASI) having the above Formula 2 are produced in the L\ l )A I I i following manner.
(1) Namely, olefin ether of alkoxypolyoxyalkylene glycol is reacted with maleic anhydride and then with a poly- R and R are hydrogen or hydrocarbon groups of amine to f i i m 2m+1 0T k 2k1: a R3 and 4 re hy rogen or The above described olefin ethers are produced in the fvllkyl g p of J 2 +1, m 18 an integef 0f 1 t0 k following manner. Alkoxypolyoxyalkylene glycol is added 15 Integer 0f 3 t0 1' is all Integer 0f 1 and with metallic sodium or sodium methylate (CH ONa) x, y, z and n are 0 or an integer of 1 to 100. to convert the end OH group into ONa, to which a The polyethers having the above Formula 1 are obmonohaloolefin is reacted. The monohaloolefin has the tained by subjecting to an addition polymerization profollowing formula.
X RCH: C=CHI action, the unreacted polyamine and the solvent are dis- I tilled off to obtain the product. The polvammes have the following formula In the above formula, X is chlorine, bromine or iodine HQN CH -NH H and R and R have the same meanings as described L\ (8) above. Illustrative of the monohaloolefin is allyl chloride and include ethylenediamine, diethylenetriamine, triethyland B-methallyl chloride. enetetramine, tetraethylenepentamine, trimethylenedi- For example, butoxypolyoxypropylene glycol is reacted amine and tetramethylenediamine.
O (9) with allyl chloride. When PASI of the present invention is added to the polyether, this dispersant shows an excellent lubricating crH O CH,CH-OH CHBONB property and cleaning and dispersing ability and does not 3 form ashes and is suitable for the use for an engine oil of an internal combustion engine. C4H9O CHrCH-O-NB CH3OH The following examples are given for the purpose of H (4) illustration of this invention and are not intended as limitations thereof. C4H O(OH;CH-O -Na C1GH,OH=0H, In the examples, part and percent mean by weight.
EXAMPLE 1 7 Nae 100 parts of butoxypolyoxypropylene glycol allyl ether CH; (5) having a molecular weight of about 1,000 is added with Alternatively, an alcohol having the following Formula 6 105 Parts of maleic anhydride and Parts P y OH D (ditert.-butyl peroxide, made by Nippon 0118 and Fats 40 Co., Ltd.) and the resulting mixture was reacted at 180- 1 190 C. for 5 hours to obtain butoxypolyoxypropylene is polymerized with alkylene oxides and then the end OH glycol allyl ether succinic anhydride in a reaction ratio of group is reacted with alkylmonochloride (R' X) to .form more than 95%. an alkylethe 110 parts of said succinic anhydride is dissolved in 130 1 mole of the olefin ether having the above Formula 5 parts of xylol and 10.5 parts of tetraethylenepentamine is is reacted with 1-7 moles, preferably l-3 moles of maleic added dropwise thereto at 160 C. in 2 hours. The reacanhydride at a temperature of ISO-230 C., preferably tion mixture is cured for 3 hours and then xylol and the 180-200 C. for 5-20 hours. unreacted polyamine are distilled olf to obtain 120 parts 0 of butoxypolyoxypropylene glycol allyl ether succinimide.
0.11,0(oH,oH-o- -orr2-0H=om era-cf EXAMPLE 2 5H: )n 0 100 parts of lauroxypolyoxyethyleneoxypropylene glycol methallyl ether (molar ratio of E0 to PO; 1:9) having a molecular weight of 1,200 is added with 12 parts of 0 maleic anhydride and the mixture is reacted at 180-190 C. for 20 hours. As the amine, 8.5 parts of methylene tetramine is used and the reaction is effected in the same CH: 11 manner as in Example 1 to obtain 117 parts of lauroxypolyoxyethyleneoxypropylene glycol methallyl ether succinimide.
(7) EXAMPLE 3 Less than 2% by weight of organic peroxide may be The reaction is effected in the same manner as described added as the reaction catalyst. In order to prevent the i Example 1 except that methoxypolyoxyethyleneoxythermal decomposition of the reaction product, the reacpropyleneoxybutylene glycol allyl ether (molar ratio of tion may be effected in gaseous nitrogen by adding EOzPOzBO; 1:821) having a molecular weight of about xylol, toluene and the like as a diluting solvent. After the 1,000 is used and 5.0 parts of tetramethylenediamine is reaction, unreacted maleic anhydride and xylol are reused as the polyamine, to obtain 114 parts of meth-oxymoved by a distillation under a reduced pressure. polyoxyethyleneoxypropyleneoxybutylene glycol allyl Thereafter, 1 mole of the compound having the above ether suceinimid described Formula 7 is dissolved in xylol and then 1-7 I h example, E0 is ethylene oxide, PO is propylene moles, preferably 1-3 moles of a polyamine is added id d B0 i b t l id thereto gradually and the reaction mixture is heated at 120-180 C. to effect dehydration while refluxing xylol, EXAMPLE 4 whereby imide is formed. The progress of the reaction can The compositlon of samples of engine oil is shown in be observed by the amount of water formed. After the rethe following Table l.
TABLE 1 Dispersant Polyether P-a-NA Sample Name Part Name (viscosity) Part (part) A Butgxypolyoxyprgpylene glycol allyl 2 Butoxypolyoxypropylene glycol (SAE- iO). 96 2 e er succ e. B Lauroxypolyoxyethyleneoxypropylene Lauroxypolyoxyethyleneoxypropylen 93 2 glycol methallyl ether succinimide. gsxoElggolar ratio of E0 to P0, 1:9) 0 Methoxypolyoxyethyieneoxypro- 3 Methoxypolyoxyethyleneoxypro- 95 2 pyleneoxybutylene glycol allyl ether pyleneoxybutylene glycol (molar ratio succinimide. EOzPOzBO, 1:8:1) (SAE-40). D N Butoxypolyoxypropylene glye 98 2 P-a-NA is an antioxidant of phenyl-u-naphthyi amine.
Test manner The dispersant was added to an engine oil of motorcar and the runnnig test was made. A common motorcar having a displacement of 2,000 cc. was used and the running test was effected based on the following standard of the exchange of the sample oil.
Sample oil A, B, C, D of the Table 1, fuel: L.P.G. Standard of exchange, 30,000 kin/3 months.
Four new cars were charged with the sample oils separately and the cars were run under usual running condition and after about 240,000 km. was run for 2 years, each portion of the engine was checked based on C.R.C. estimation standard.
01 (molecular weight 1,200) (SAE-40).
having the following formula of 1-100, and n is an integer of l-100, (Ll-10% by weight of a polyoxyalkylene glycol ether N-amine substitutcd succinimide having the following formula R O CH CHO CH CHO CH CHO L i. M l, M i, )1
Analysis of the sample oil cH=c-oH,-oH-o L After about 30,000 km. was run for 3 months, the 2 D J, total amount of oil was discharged and exchanged. The z analyzed value is shown in Table 2.
TABLE 2 Sample 011 A B C D Before After Before After Before After Before After Item use use use use use use Viscosity, 98.9 C. (0st.) 15. 6 15. 6 13. 6 Viscosity, 37.8 C. (cst.). 96. 5 99. 8 87. 1 Viscosity index number-. 141. 0 139. 6 138. 8 PH (isopro water) 9. 1 4. 0 3. 4 Remaining carbon, percent 1.3 1. 68 Heptane, insoluble percent portion- 2. 9 4. 5 Carbon dispersibility Good Bad Oil element condition G d 1 1 Fairly bad.
NorE.Isopro water means a solution of 10 g. of sample dissolved in 60 ml. of a mixture of isopropyl alcohol and water (mixture ratio of isopropyl alcohol to water is 10:6 by volume).
The estimation of each portion of engine is shown in the following Table 3.
TABLE 3 A B c D Running distance of sample Oil, km- 239, 372 236, 579 230, 370 239, 671
Item:
Cleaning ability of piston:
Deposit of carbon on top ring groove Deposit on ring groo Deposit on ring land.. Agglomeration on ring Deposit on piston crown Deposit on under crown... Deposit on piston skirt.-.- Cleaning ability of lubricating oil tellillli No No No No wherein R R R x, y, z and n: have the same meanings as described above, R' is C H i (m is an integer of 1-18), R is C,;H;, (g is 0 or an integer of 1-15), R is hydrogen or a hydrocarbon group of C H (f is 0 or an integer of 1-3) and p and s are an integer of 1-6.
2. Polyether series synthetic lubricating oil composition as claimed in claim 1, wherein the polyoxyalkylene glycol ether Nsubstituted succinimide is butoxypolyoxypropylene glycol allyl ether succinimide.
3. Polyether series synthetic lubricating oil composition as claimed in claim 1, wherein the polyoxyalkylene glycol ether N-substituted succinimide is lauroxypolyoxyethyleneoxypropylene glycol methallyl ether succinimide.
4. Polyether series synthetic lubricating oil composition as claimed in claim 1, wherein the polyoxyalkylene glycol ether N-substituted succinimide is methoxypolyoxyethyleneoxypropyleneoxybutylene glycol allyl ether succinimide.
References Cited UNITED STATES PATENTS WERTEN F. W. BELLAMY, Primary Examiner Patent No. 3,7 6,6 5 Dated November 26, 1971 Inventor(s) IT ET AL It is eertified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Column 3, line 35 "NaC"" should be NaCl Column 3, line 56 "Cn"" should be CH Column 6, Line nu "138.8"" should be 138.5 Column 6, line 5 "31 1'" should be 3.8
-'Column 6, line &6 "1.68"" should be' 1.6M Column 6, line- 47 1.5" should be u.8
- Signed and sealed this 29th day of October 1974.
(SEAL) Attest:
McCOY M. GIBSON JR. C. MARSHALL DANN Attesting Officer Commissioner of Patents
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3897454A (en) * 1968-10-08 1975-07-29 Atlantic Richfield Co Polyalkylene glycol polyalkylene polyamine dispersants for lubricant fluids
US4194985A (en) * 1974-01-14 1980-03-25 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3897454A (en) * 1968-10-08 1975-07-29 Atlantic Richfield Co Polyalkylene glycol polyalkylene polyamine dispersants for lubricant fluids
US4039461A (en) * 1968-10-08 1977-08-02 Atlantic Richfield Company Polyalkylene glycol polyalkylene polyamine succinimide dispersants for lubricant fluids
US4194985A (en) * 1974-01-14 1980-03-25 The Lubrizol Corporation Polymeric compositions, method for their preparation, and lubricants containing them

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