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EP0076595B1 - Fluides hydrauliques contenant de l'eau et des isocyanurates hydroxyalkylées - Google Patents

Fluides hydrauliques contenant de l'eau et des isocyanurates hydroxyalkylées Download PDF

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Publication number
EP0076595B1
EP0076595B1 EP82304993A EP82304993A EP0076595B1 EP 0076595 B1 EP0076595 B1 EP 0076595B1 EP 82304993 A EP82304993 A EP 82304993A EP 82304993 A EP82304993 A EP 82304993A EP 0076595 B1 EP0076595 B1 EP 0076595B1
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Prior art keywords
hydraulic fluid
weight
fluid
water
fluids
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English (en)
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EP0076595A2 (fr
EP0076595A3 (en
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Robert N. Scott
David F. Gavin
Robert J. Bucko
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Olin Corp
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Olin Corp
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
    • C10M173/02Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38Heterocyclic nitrogen compounds
    • C10M133/40Six-membered ring containing nitrogen and carbon only
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    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08Inorganic acids or salts thereof
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • C10M2215/065Phenyl-Naphthyl amines
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    • C10M2215/22Heterocyclic nitrogen compounds
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    • C10M2215/226Morpholines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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    • C10M2219/108Phenothiazine
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    • C10M2229/02Unspecified siloxanes; Silicones
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01Emulsions, colloids, or micelles

Definitions

  • the present invention relates to fire-resistant hydraulic fluids containing water and hydroxyalkylated isocyanurate base stocks.
  • Water-based hydraulic fluids having fire-resistant properties are well known. See R. E. Hatton, Introduction to Hydraulic Fluids, Chapter 13, “Water-Based Fluids", pages 273-287, Reinhold Publishing Corporation (1962). Such water-based fluids have been used satisfactorily in hydraulic systems containing vane, gear or axial-piston pumps. The fire resistance of these water-based fluids had depended solely upon their water content, and they were generally considered to be satisfactorily fire resistant as long as the water content was maintained. If the water is allowed to boil away or to evaporate by prolonged exposure to elevated temperatures, the residual material will burn when ignited.
  • hydroxyalkylated isocyanurates have been known as functional fluids. See U.S. Patent No. 3,859,284, which issued to Formaini et al on January 7, 1975.
  • their desirable characteristics of (1) being fire resistant in water-based fluids even after the water is removed and (2) possessing good lubricating properties while in combination with water were not known prior to the present invention.
  • EP-A-10452 discloses isocyanurate compounds and their use in functional fluid systems.
  • the substituent on each nitrogen atom is where x is an integer from 2-10, Y is hydrogen or methyl and R is C ' - 4 alkyl.
  • the isocyanurates may be used with diluents but the emphasis is on glycol ether diluents and water is only once mentioned as a possible diluent.
  • R 1 , R 2 and R 3 are defined as follows.
  • R is a hydrogen-terminated oxyalkylene chain of from 2 to 30 oxyalkylene units
  • R 2 and R 3 are each a hydrogen-terminated oxyalkylated chain of from 1 to 30 oxyalkylene units.
  • Each oxyalkylene unit has the formula wherein each R is hydrogen, methyl or ethyl.
  • the isocyanurates having a content of more than 6 moles of alkylene oxide reacted per mole of tris(hydroxyalkyl)isocyanurates are said to be, inter alia, useful in functional fluid applications, but the only utility described in detail is the preparation of polyesters for use in wire enamels and varnishes, casting resins and the preparation of ester-imide copolymers.
  • the present invention is directed to water containing hydraulic fluids with a viscosity of 100 SUS (20.52 mm 2 /s or cSt) to 400 SUS (86.2 mm 2 /s or cSt) at 100°F (38°C) which comprise
  • the present invention is also directed to the process of using these fluids in hydraulic operations.
  • the hydroxyalkylated isocyanurate base stock of the present invention may be prepared either (1) by the catalytic alkoxylation of cyanuric acid or (2) by the catalytic alkoxylation of tris(2-hydroxyethyl) isocyanurate (THEIC).
  • TEEIC tris(2-hydroxyethyl) isocyanurate
  • the former method is described in U.S. Patent No. 3,265,694, which issued to Walles et al on August 9, 1966.
  • the latter synthesis is described in U.S. Patent No. 3,741,966, which issued to Weedon et al on June 26,1973, and in U.S. Patent No. 3,859,284, which issued to Formaini et al on January 7, 1975.
  • the present invention is not to be limited to any specific method for making the hydroxyalkylated isocyanurates and any conventional method for making these compounds may be used.
  • oxide precursors of these hydroxyalkylated isocyanurates are commercially available chemicals which may be obtained from many sources. Mixtures of different oxides [e.g. ethylene oxide (EO) and propylene oxide (PO)] may also be employed as reactants, either added sequentially or mixed together.
  • EO ethylene oxide
  • PO propylene oxide
  • the number of moles of oxide reacted at each of the three reactive sites of the isocyanurate molecule will not always be the same. For example, if 12 moles of EO were reacted to 1 mole of THEIC, it does not necessarily follow that 4 moles of EO were added at each site. Instead, it may be in some instances that only 3 moles, or none, will react at one site and 5, or more, moles may react at another site. Furthermore, it should be understood that the total number of alkylene oxide moles on each resulting adduct molecule will be statistically distributed. Thus, the values for x, y and z in Formula (A) each represent the average amount of alkylene oxide units per reaction site and that the actual number may be less or greater than the amount.
  • hydroxyalkylated i.e. hydroxyethylated and hydroxypropylated and mixtures thereof
  • isocyanurates are viscous fluids. Unlike ethylene and propylene glycols, they do not require additional thickeners to make water-based hydraulic fluids of acceptable viscosities and lubricity. Generally, the viscosities of these hydroxyalkylated isocyanurates are from about 500 centistokes (cSt) to about 800 centistokes (cSt) at 100°F (38°C) which when converted to SUS values by the appropriate tables in ANSI/ ASTM 2161-79, equals from about 2300 SUS to about 3700 SUS.
  • these viscosities are more easily achieved when the amount of water in the fluid - is from 22% to 50% by weight and the preferred amount of hydroxyalkylated isocyanurate is from about 80% to about 25% by weight, depending upon the specific thickeners and additives present.
  • x, y and z in Formula (A), above be from 4 to 10.
  • water-based isocyanurate fluids of the present invention over the known water-based glycol fluids is that these hydroxyalkylated isocyanurates per se have better lubricating properties than the glycols. Therefore, lesser amounts of anti-wear and lubricity additives are needed to achieve the same lubricating properties.
  • At least one liquid phase and at least one vapor phase corrosion inhibitor are needed to prevent corrosion of metal hydraulic system parts. These corrosion inhibitors are necessary because the water would otherwise corrode the metal in which the hydraulic fluid is contained.
  • liquid phase corrosion inhibitor Any conventional liquid phase corrosion inhibitor may be employed.
  • Mercaptobenzothiazole or its alkali metal salts such as sodium mercaptobenzothiazole, tolutriazole, secondary and tertiary amines and alkali metal borates, phosphates, nitrites, phosphites and silicates, or other suitable liquid phase corrosion inhibitors may be employed.
  • the amount of liquid phase corrosion inhibitors is from about 0.1 % to about 1% by weight of the total hydraulic fluid formulation. More preferably, the amount of liquid phase corrosion inhibitors is from about 0.2% to about 0.5% by weight of the total fluid formulation.
  • Vapor phase corrosion inhibitors such as morpholine, organic bases such as cyclohexylamine, dicyclohexylamine, piperidine, and various thiazolines, pyrrolidines and hydrazines are required to protect parts not completely immersed in the fluid, especially in the fluid reservoirs which would be vulnerable to corrosion above the liquid level.
  • the amount of vapor phase corrosion inhibitors is from about 0.5% to about 2% of the total formulation. More preferably, this amount may be from about 0.7% to about 1.25% by weight of the total fluid formulation.
  • the hydraulic fluids of the present invention may be suitable for industrial hydraulic service throughout the temperature range from about -20°C to about 65°C at atmospheric pressure (higher temperatures may be used under pressurized conditions) and are homogeneous at all temperatures between about -45°C to about 80°C. They require no special packings or seals or filters. These fluids, besides being fire resistant, are non-explosive, will not attack rubber packings, are corrosion-inhibited, nontoxic, oxidation resistant, and have low pour points, good lubricity and stability in service. Furthermore, they are economical to make.
  • the hydraulic-type fluid systems in which the fluids of the present invention may be used include any system wherein a mechanical effort is converted to pressure at a first location, the pressure is transmitted from this first location to a second location via a hydraulic fluid, and the pressure is converted to a second mechanical effort at the second location.
  • the hydraulic systems contemplated by the present invention include hydraulic brake systems, hydraulic steering mechanisms, hydraulic transmissions, hydraulic jacks and hydraulic lifts, especially those that require a high degree of fire resistance. Included among these are the hydraulic systems used in heavy equipment and transportation vehicles including highway and construction equipment, railways, and aquatic vehicles.
  • additives may be added to the fluids used in the systems of this invention to control or modify performance properties.
  • additives include thickeners, buffers or pH control agents, antioxidants, viscosity index improvers, pour point depressants, lubricating additives, defoamers, stabilizers, rubber swelling adjusters, demulsifiers, dyes and odor suppressants.
  • the total amount of additives which may be incorporated into the fluid composition will vary between 0% to about 30%, preferably from about 0.1 % to 20% and more preferably from about 0.2% to about 10% by weight, based on the total weight of the fluid formulation.
  • Thickeners such as polyoxyalkylene glycol-type thickeners such as the water-initiated co-polymers of ethylene oxide and propylene oxide may optionally be added to the fluids of the present invention to effect an increase in the viscosity index of the fluid.
  • the amount of thickeners added may be from about 0% to about 20%, preferably from 0% to 15%, by weight of the total fluid formulation.
  • the addition of thickeners reduces both fire-resistance of the residual material and the lubricity of the fluid.
  • Buffers or pH control agents may optionally be employed in an amount sufficient to maintain alkaline conditions in the fluid compositions, e.g. at an apparent pH value of about 7 to about 11.5, if desired. Acidity might accelerate corrosion and render some corrosion inhibitors ineffective. Desirable buffers include potassium laurate and triethanolamine, ammonium phosphate, borates and the like. These buffers may generally be added to the fluids in amounts from about 0% to about 5% by weight of fluid formulation, preferably from 0.1 % to 1% by weight of the mixture.
  • antioxidants may optionally be used, if desired.
  • Typical antioxidants include 2,2-di(4-hydroxyphenyl) propane, phenothiazine, amines such as phenylalphanaphthylamine and hindered phenols such as dibutyl cresol.
  • the amount of antioxidant used will vary from 0% to about 3% by weight, preferably from about 0.001% to about 2% by weight, based on the total weight of the fluid formulation.
  • a defoamer such as a silicone type may be optionally used, if desired.
  • the amount of defoamer used will vary from 0% to about 0.1 % by weight of the fluid formulation; preferably, the amount will be from 0.01% to about 0.1 % by weight of the formulation.
  • additives may be incorporated into the fluid composition.
  • rubber swelling adjusters such as dodecyl benzene may be used.
  • inhibitors and additives are merely exemplary and are not intended as an exclusive listing of the many well-known materials which can be added to fluid compositions to obtain various desired properties.
  • Other illustrations of additives which may be used can be found in U.S. Patent No. 3,377,288, and in Introduction to Hydraulic Fluids by Roger E. Hatton, Reinhold Publishing Corporation (1962).
  • TSEIC tris(2-hydroxyethyl) isocyanurate
  • boron trifluoride etherate boron trifluoride etherate
  • the latter compound was used as a catalyst in an amount equal to about 1.0% of the weight of the THEIC.
  • the autoclave was sealed and the reaction mixture was heated to about 140°C to melt the THEIC.
  • the reaction pressure was maintained at about 50 psig.
  • Ethylene oxide (EP) was then added to the autoclave over a period of about 3 hours until 436 grams (9.9 moles) EO was charged.
  • the reaction mixture was then post-reacted for 1 hour at 138°-150°C.
  • the reactor was cooled to room temperature, vented to remove any unreacted EO, and the contents were weighed (440.3 grams) and OH number determined (234) which corresponds to a calculated molecular weight of 719.
  • the hydroxyalkylated isocyanurate product made in Example 1 was blended with water and a polyalkylene glycol thickener' prepared by base-catalyzed, water-initiated copolymerization of a mixture of 75% EO and 25% PO by weight (36,000 cSt at 100°F) to form a hydraulic fluid having a viscosity of 200 SUS (42.95 cSt) at 100°F (38°C).
  • This fluid comprised 39.0% of the isocyanurate product, 50.0% water and 11.0% thickener.
  • the fluid was also tested for various properties. See Table I for the results.
  • reaction mixture was heated to about 125°C for an additional 16 hours, cooled to room temperature and the contents weighed (159.0 grams) and the OH number was determined (208), which corresponded to a calculated molecular formula of 809.
  • a water-based hydraulic fluid having about 200 SOS (42.95 cSt) viscosity at 100°F (38°C) comprising 73.0% by weight of the above hydroxyalkylated isocyanurate and 27.0% distilled water was prepared and tested for various properties. See Table I for the results.
  • a water-based hydraulic fluid having a 200 SUS (42.95 cSt) viscosity of 100°F (38°C) comprising 75.0% by weight of this isocyanurate product and 25.0% by weight of distilled water was then prepared and tested. The results of those tests are in Table I.
  • a hydroxyalkylated isocyanurate compound was prepared by the continuous addition of 41.4 Ibs (18.8 kg) of EO to 15.4 Ibs (7 kg) of THEIC and 60 grams of BF 3 etherate in a 10-gallon reactor. The reactor was heated to 295°F to melt the THEIC at which point agitation and EO addition were begun. Only half of the EO had been added when the pressure reached its maximum of 65 psig (448 kPa). A second 60 gram catalyst charge was added to the vapor space above the liquid reaction mixture and the run continued until the EO was consumed. The resulting fluid had an OH number of 205. The molecular weight was calculated from the OH number to be 821. The average composition from calculated molecular weight was C 3 N 3 O 3 [(CH 2 CH 2 O) 5.2 H]3. ' Poly-GO polyalkylene glycol thickener concentrate manufactured by Olin Corporation of Stamford, Connecticut.
  • a two quart batch of hydraulic fluid having a viscosity of approximately 200 SUS (42.95 cSt) was prepared by mixing 1579.8 grams of the isocyanurate base stock, 630.2 grams of distilled water, 11.0 grams of morpholine and 0.4 grams of SAG-10 silicone defoaming agent 2 in a beaker. The pH was raised to 9.5 by the addition of 14.6 grams of 1-amino-2-propanol. See Tables I and II for test results. The final composition of the fluid was:
  • the hydroxyalkylated isocyanurate product for this example was prepared by a reaction similar to that of Example 5 except that only 34.4 Ibs (15.6 kg) of EO was added and the 60 grams of catalyst was charged into the melted THEIC. No further catalyst addition was necessary.
  • the resulting fluid had an OH number of 199 and as in Example 5, the molecular weight was calculated to be 845 which corresponded to an average composition of: C 3 N 3 O 3 [(CH 2 CH 2 O) 5.4 H] 3 .
  • Two quarts of hydraulic fluid having a viscosity of approximately 200 SUS (42.95 cSt) were prepared.
  • the same polyoxyalkylene glycol thickener (36,000 cs at 100°F) as used in Example 2 was used to increase the viscosity index.
  • the viscosity of the thickener allows a lower isocyanurate fluid to water ratio to be used.
  • Corrosion inhibitors, buffers and defoamer were also added. Two hundred grams of thickener were dissolved in 925.6 grams of water with stirring and heating followed by the addition of 788.4 grams of the base stock.
  • the hydroxyalkylated isocyanurate product for this formulation was prepared by a reaction similar to that described in Example 6.
  • the resulting product had an OH number of 209. Its molecular weight was calculated to be 805 which corresponds to an average composition of: C 3 N 3 O 3 [(CH 2 CH 2 O) 5.1 H] 3 .
  • the hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7. About four quarts (3.86 x 10- 3 m 3 ) of hydraulic fluid having 200 SUS (42.95 cSt) viscosity at 100°F (38°C) were prepared and tested (see Tables I and II).
  • the fluid had the following composition:
  • the hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7. About four quarts (3.86 x 10 -3 m 3 ) of hydraulic fluid having 150 SUS (31.90 cSt) viscosity at 100°F (38°C) were prepared and tested (see Tables I and II).
  • the fluid had the following composition:
  • the hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7. About four quarts (3.86 x 10 -3 m 3 ) of hydraulic fluid having 100 SUS (20.52 cSt) viscosity at 100°F (38°C) were prepared and tested (see Tables I and II).
  • the fluid had the following composition:
  • the isocyanurate water-based fluids are comparable in physical properties and lubricity characteristics to typical water glycol fire-resistant hydraulic fluids, but offer a substantial reduction in the flammability of the residual material resulting from loss of water content.
  • Fluids of the present invention such as these may be desirable for improving safety in Naval Ship hydraulic systems, die casting machines, forging and extrusion presses, injection molding machines, continuous casters, rolling mills, furnace controls, automatic welders, hydraulic shears, continuous coal miners and mine shuttle cars, and many other uses where the threat of fires exists.

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  • Lubricants (AREA)

Claims (15)

1. Un fluide hydraulique contenant de l'eau avec une viscosité de 100 SUS (20,52 mm2/s ou cSt) à 400 SUS (86,2 mm2/s ou cSt) à 100°F (38°C) qui comprend
(a) 20% à 60% en poids d'eau:
(b) 25 à 80% en poids d'un isocyanurate hydroxyalkylé ayant pour formule:
Figure imgb0014
dans laquelle x, y et z sont chacun de 3 à 15 et chaque R est individuellement choisi parmi un hydrogène et un méthyle;
(c) 0,01% à 5% en poids d'un inhibiteur de la corrosion en phase liquide; et
(d) 0,01 % à 5% en poids d'un inhibiteur de la corrosion en phase vapeur.
2. Le fluide hydraulique de la revendication 1 qui contient de 22% à 50% en poids d'eau.
3. Le fluide hydraulique de la revendication ou 2 dans lequel chaque R est un hydrogène.
4. Le fluide hydraulique de la revendication 1 ou 2 dans lequel chaque R est un méthyle.
5. Le fluide hydraulique de l'une quelconque des revendications précédentes dans lequel x, y et z sont chacun de 4 à 10.
6. Le fluide hydraulique de l'une quelconque des revendications précédentes dans lequel ledit inhibiteur de la corrosion en phase liquide comprend du mercaptobenzothiazole sodique.
7. Le fluide hydraulique de l'une quelconque des revendications 1 à 5 dans lequel ledit inhibiteur de la corrosion en phase liquide comprend du tolutriazole.
8. Le fluide hydraulique de l'une quelconque des revendications 1 à 5 dans lequel ledit inhibiteur de la corrosion en phase liquide comprend une combinaison de mercaptobenzothiazole sodique et de tolutriazole.
9. Le fluide hydraulique de l'une quelconque des revendications précédentes dans lequel ledit , inhibiteur de la corrosion en phase vapeur est la morpholine.
10. Le fluide hydraulique de l'une quelconque des revendications précédentes qui contient de plus de 0% à 15% en poids d'un épaississant.
11. Le fluide hydraulique de la revendication 10 dans lequel ledit épaissassant est un copolymère d'oxyde d'éthylène et d'oxyde de propylène.
12. Le fluide hydraulique de l'une quelconque des revendications précédentes qui contient de plus de 0,1% à 1% en poids d'au moins un tampon.
13. Le fluide hydraulique de la revendication 12 dans lequel ledit tampon est choisi parmi le laurate de potassium, la triéthanolamine et leurs mélanges.
14. Le fluide hydraulique de l'une quelconque des revendications précédentes qui contient de plus 0,01 % à 0,1% en poids d'un antimousse.
15. Un procédé dans lequel un premier effort mécanique est transformé en une pression en un premier emplacement, la pression est transmise dudit premier emplacement à un second emplacement par un fluide hydraulique et ladite pression est transformée en un second effort mécanique audit second emplacement; caractérisé par l'emploi du fluide de l'une quelconque des revendications précédentes comme dit fluide hydraulique.
EP82304993A 1981-10-02 1982-09-22 Fluides hydrauliques contenant de l'eau et des isocyanurates hydroxyalkylées Expired EP0076595B1 (fr)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
RU2103334C1 (ru) * 1995-07-18 1998-01-27 Акционерное общество закрытого типа "Центральный научно-исследовательский и проектно-конструкторский институт морского флота" Смазочная композиция

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CN102010782A (zh) * 2010-12-14 2011-04-13 上海德润宝特种润滑剂有限公司 一种抗燃液压液组合物及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0010452A1 (fr) * 1978-10-25 1980-04-30 Olin Corporation Composés d'isocyanurate tris-(polyalcoxyalcoylé) et leur utilisation comme fluides fonctionnels

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BE734848A (fr) * 1968-06-21 1969-12-01 Allied Chem

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0010452A1 (fr) * 1978-10-25 1980-04-30 Olin Corporation Composés d'isocyanurate tris-(polyalcoxyalcoylé) et leur utilisation comme fluides fonctionnels

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2103334C1 (ru) * 1995-07-18 1998-01-27 Акционерное общество закрытого типа "Центральный научно-исследовательский и проектно-конструкторский институт морского флота" Смазочная композиция

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EP0076595A3 (en) 1983-07-20

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