US3623987A - Functional fluids - Google Patents

Functional fluids Download PDF

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Publication number
US3623987A
US3623987A US3553A US3623987DA US3623987A US 3623987 A US3623987 A US 3623987A US 3553 A US3553 A US 3553A US 3623987D A US3623987D A US 3623987DA US 3623987 A US3623987 A US 3623987A
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mixture
percent
esters
group
carbon atoms
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Robert Alan Cameron Ker
Robert Carswell
John Lavington Clarke
Peter Anthony Burt
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COSTROL Ltd
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COSTROL Ltd
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • 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
    • C10M2215/24—Organic 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
    • C10M2215/26—Amines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic 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
    • C10M2215/30—Heterocyclic compounds
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • Hydraulic brake systems comprise metal and rubber parts which are exposed to the liquid employed as the power transmitting medium and it is essential that a liquid be used which has little, if any attack on either the metal or the rubber parts of the brakesystem, either at ordinary temperatures or at the elevated temperatures which are setup in the parts of the system adjacent to the braking surfaces during a prolonged application of the brakes. It is further more essential that the hydraulic transmission medium shoulder be stable and of a high boiling point such as not to vaporize to any substantial extent under operating conditions.
  • the liquid should have a low freezing point to withstand operating temperatures which obtain either during cold weather, or in the case of aircraft, during high altitude flight. in addition it is necessary that the liquid shall have a sufficiently low viscosity to render the system readily operable, the viscosity not changing to any material extend under operating conditions. Finally further important considerations are that the liquid shall have a low rate of vaporization and also sufficient lubricating properties properly to lubricate the moving parts of the system.
  • Fluids of this latter type in commercial use normally comprise a major proportion of one or more polyethylene glycols, ethers or polyethylene glycols, or mixtures of such compounds. Minor proportions of castor oil or lubricity additives, such as polyalkylene glycol polyesters, may be present, together with one or more corrosion inhibitors.
  • hydraulic brake fluids based on polyethylene glycols and/or ethers thereof are hygroscopic an in process of time water is absorbed from the atmosphere and the boiling point steadily falls.
  • two brake fluids having initial boiling points more than 56 C. apart may be found to have boiling points of the same order, both substantially below the initial boiling points of the fluids.
  • a typical known hydraulic brake fluid, fluid A having an initial boiling point of 216 C., was found to have a boiling point of 182 C. when l percent of water was added and a boiling point of only 141 C. when 3 percent of water was present.
  • a known high-temperature brake fluid, fluid B which had an initial boiling point of 271 C. was found to have a boiling point of 204 C. when 1 percent of water was present and of only 154 C. when 3 percent of water was present.
  • the high temperature brake fluid therefore, had become inferior to the conventional brake fluid in its original condition as a result of absorbing only 1 percent of water. 7
  • high-temperature hydraulic fluids which have relatively low hygroscopicity and high boiling points, may be formulated from certain esters of organic .dicarboxylic acids and ethers of certain glycols.
  • the invention provides a hydraulic fluid having a kinematic viscosity at 40 C. of not more than 5,000 centistokes, preferably not more than 2,000 centistokes, and preferably having a boiling point of at least 260 C., and either consisting of or comprising at least 50 percent by weight, preferably at least percent of at least one ester having the general formula (JOORMORDnOR where R is a straight or branched chain alkylene group which contains at least two, preferably from two to eight carbon atoms, R is an alkyl radical having from one to four preferably one to two carbon atoms or a phenyl radical R is anethylene, propylene or butylene group, and n is O, l 2 or 3, together with a minor amount of at least one additive.
  • the groups R- R and n may be the same or different.
  • Preferred acids R(COOH from which the esters are derived are succinic, glutaric,- adipic, azelaic, sebacic and isosebacic acids, although other dicarboxylic acids may be used, if desired, c.g. a commercially available mixture of adipic, glutaric and succinic acids, known as A.G.S. acid.”
  • Preferred examples of the glycol ethers from which the esters are made are:
  • Ethylene glycol monomethyl ether (Methyl Oxitol" or Methyl Cellosolve”).
  • Diethylene glycol monoethyl ether Diethylene glycol monoethyl ether (Dioxitol or "Carbitol).
  • Diethylene glycol monomethyl ether (Methyl Dioxitol" or Methyl Carbitol).
  • Triethylene glycol monomethyl ether (Methyl Trioxitol).
  • esters in accordance with the present invention are given in table 1 together with their physical properties, it being understood that when the esters have too high a viscosity, particularly at -40 C., then they may be blended with a suitable ester or a small amount of inert diluent to give a fluid having the viscosity requirements in accordance with the present invention.
  • a suitable ester or a small amount of inert diluent for example a blend of 15 percent di(ethyl trioxitol) sebacate and percent (methyl oxitol adipate had the following viscosity characteristics:
  • Typical additives which may be used in the invention are lubricity additives selected from castor oil or castor oil treated in various ways, for example,
  • Castor oil to specification DTD72 Blown castor oil i.e. castor oil blown with air or oxygen while being heated.
  • Hydricin 4" i.e. a commercially available ethylene/oxide/propylene oxide treated castor oil.
  • lubricity additives which may be incorporated in hydraulic fluids in accordance with the present invention include borate esters e.g. tricresyl borate and phosphorus-containing esters, especially phosphates e.g. tricresyl phosphate.
  • the hydraulic fluids of the present invention may also include minor proportions of polyexyalkylene or ethers thereof e.g. those sold under the Reg. Trade Mark Ucon, particularly those of the LB and HB series. Suitable examples of these polyoxyalkylene glycols and their ethers and esters are given in our copending application No. 337,181 filed Jan. 13, 1964 now U.S. Pat.
  • No 3,334,048 together with examples of other suitable lubricity agents such as orthophosphate or sulfate salts of primary or secondary aromatic amines, dialkyl citrates, aliphatic dicarboxylic acids and esters thereof, specific examples being Diamylamine orthophosphate Dinonylamine orthophosphate Diamylamine sulphate Dinonyl citrate Di (2-ethyl hexyl) citrate Polyoxyethylene sebacate derived from a polyaxyethylene glycol of M.W. 200
  • Polyoxethylene azelate derived from polyoxyethylene glycol of M.W. 200
  • Corrosion inhibitors which may be used in the present invention may be selected from heterocyclic nitrogen-containing compounds e.g. benzotriazole and benzotriazole derivatives such as those described in British Pat. specification No. 1,061904 or mercapto benzothiazole. Many amines or derivatives thereof are also suitable as corrosion inhibitors, for example di n-butylamine di n-amylamine cyclohexylamine morpholine triethanolamine and soluble salts thereof e.g. cyclohexylamine carbonate.
  • heterocyclic nitrogen-containing compounds e.g. benzotriazole and benzotriazole derivatives such as those described in British Pat. specification No. 1,061904 or mercapto benzothiazole.
  • Many amines or derivatives thereof are also suitable as corrosion inhibitors, for example di n-butylamine di n-amylamine cyclohexylamine morpholine triethanolamine and soluble salts thereof e.g
  • Phosphites are also good corrosion inhibitors e.g.
  • antioxidants such as diarylamines e.g. diphenylamine, p.p. 'dioctyldiphenylamine, phenyl-a-naphthylamine or phenyl-B- naphthylamine.
  • antioxidants are those commonly known as hindered phenols which are exemplified by 2,4dimethyl-6-t-butyl phenol 2,6 di-t-butyl -4-methyl phenol 2,6 di-t-butyl phenol 1,1 bis( 3 5 di-t-butyl-4-hydroxyphenyl)methane 3,3 ',5,5 tetra-t-butyl-4-4'-dihydroxydiphenyl 3-methyl 4,6di-t-butyl phenol 4-methyl-2-t-butyl phenol
  • further additives which may be used are phenothiazine and its derivatives, for example those having alkyl or aryl, groups attached to the nitrogen atom or to the aryl groups of the molecule.
  • additives will normally be employed in conventional amounts which, in many cases, will be from 0.05 percent to percent, for example fonn 0.1 percent to 2 percent by weight.
  • di(methy1 oxitol) succinate by itself failed the water tolerance test at --40 C., but this difficulty was overcome by incorporating 10 percent of mixed polyoxyethylene glycol ethers.
  • This water tolerance test is carried out by adding 3.5 percent of water to the composition and holding it at -40 C. for 24 hours; no ice formation or cloudiness must occur.
  • the invention also provides a hydraulic system containing a hydraulic fluid consisting of, or comprising a major proportion, preferably at least percent of at least one ester having the general formula:
  • the invention also includes a method of operating a hydraulic system which method comprises employing a hydraulic fluid consisting of, or comprising a major proportion, preferably at least 80 percent, of the ester defined above.
  • EXAMPLE 1 99 percent Di(methyl oxitol) succinate 1 percent Primene 81-R (Reg. Trade Mark for a tertiary alkyl primary amine having 12 to 14 carbon atoms).
  • This composition had viscosities of 1,680 cS. at -40 C., 3.75 cS. at 50 C. and 1.59 cS. at 100 C., and a boiling point of 292 C.
  • EXAMPLE 2 87.9 percent Di( methyl oxitol) succinate 10 percent Mixed polyoxyethylene glycol ethers 1 percent Ucon 50 HB 5100 0.1 percent Benzotriazole 1 percent Primene 81R This composition had viscosities of 1,640 08. at 40 C. 4.2 cS. at 50 C. and 1.68 cS. at 100 C. and in initial boiling point of 282 C. It also passed the SAE 7OR3 water tolerance and low temperature requirements.
  • EXAMPLE 1 39.9 percent Di(methyl trioxitol) adipate 5 3.9 percent Di( methyl oxitol) adipate 5 percent Ucon H 436 0.5 percent Di-n-butylamine 0.5 Phenyl-B-naphthylamine 0.1 percent Benzotriazole 0.1 percent Phenothiazine
  • This fluid which is very similar to that of example 10, passed all the tests of the S.A.E. 70R3 Specification. The phenothiazine appeared to act in controlling the pH, and in further reducing corrosion.
  • the hydraulic fluids of this invention as described in the examples are suitable for use under high temperature conditions, have relatively low hygroscopicity and retain high boiling 35 points over extended periods of use.
  • ester prepared by reacting ethylene glycol mono methyl ether with a mixture known as "A.G.S. Acid” containing approximately-15596 adipic acid,
  • R is an alkylene group of two to eight carbon atoms
  • R is selected from the group consisting of an alkyl radical of one to four carbon atoms and a phenyl radical
  • % volume Increase on Natural Rubber at C. R is selected from the group consisting of ethylene,
  • propylene and butylene and 2 I n is an integer offrom 0 to 3; and mid b. an organic antioxidant;
  • said component (a) being present in the mixture in an t y oxitol) succimte 236 1-26v amount of at least 50 percent by weight based on the total 3S521233223223232.3221 1:2: :5: weight Me and components 5 and a e mmflhyl omen Adipm so selected to provide a mlxture havlng a kinemat c Di(methyl trioxitol) Adipate 0.3l 1.53 viscosity at -40 C. of not more than 5,000 c5. and a boll- Di(ethyl trioxitoUAdipate l.l7 2.82 ing point f at least 2 0 2.
  • the improvement which comprises employing as the hydraulic fluid a composition consisting essentially of a mixture of the following components:
  • iw y l n t 852 R is selected from the group consisting of an alkyl radical i'gi' gs 13$; :2; of one to four carbon atoms and a phenyl radical, Dkmcnwl maxim) sebum
  • M R is selected from the group consisting of ethylene, Di (methyl trioxitol) Azelate 2.65 propylene and butylene, and Dl(ethyl trloxltol) Azelatc 7.62 n i an i g offrom 0 to 3; and +Dl( methyl oxltol) Nylonate 13.20
  • component (a) being present in the mixture in an amount of at least 50 percent by weight based on the total weight of the mixture and components (a) and (b) being +An ester prepared by reacting ethylene glycol mono methyl ether with a mixture known as A.G.S. Acid and containing approximately 15-25 percent adipic acid,
  • the Special Castor was an ethylene oxide/propylene oxide treated castor.
  • MB castor is a heat treated air blown castor oil.
  • Rcoplex 400 was a polyoxyethylene glycol adipate of molecularweight 400 marketed by Geigy Ltd.
  • Ucon 5011B 5,100 was a polyoxyethylene polyoxypropylenc glycol ethermarketed by Union Carbide and having a viscosity of about 5,100 S. U.S. at
  • viscosity at 40 C. of not more than 5000 0S. and a boil- In a method of hydraulic transmission of power to presg P ofa! 163$! sure operated elements the improvement which comprises In a method of hy r n m n f power to pr employing as the hydraulic fluid a composition consisting ess r per lem n the Impr vem nt wh h ompri sentially of a mixture of the following components: employing as the hydraulic fluld a composition consisting esa. an ester or mixture of esters of the formula sentially of a mixture of the following components;
  • R is selected from the group consisting of an alkyl radical of one to four carbon atoms and a phenyl radical
  • R is selected from the group consisting of ethylene
  • n is an integer of from to 3;
  • a lubricity agent selected from the group consisting of castor oils, triaryl borates, triaryl phosphates, polyoxyalkylene glycols and ethers thereof, orthophosphates of primary and secondary amines, sulfates of primary and secondary amines, dialkyl citrates, saturated aliphatic dibasic carboxylic acids and alkyl esters thereof, and unsaturated aliphatic acids and their salts;
  • component (a) being present in the mixture in an amount of at least 50 percent weight based on the total weight ofthe mixture and components (a) and (b) being so selected to provide a mixture having a kinematic viscosity at 40 C. of not more than 5000cS. and a boiling point of at least 260 C.
  • R is selected from the group consisting of an alkyl radical of one to four carbon atoms and a phenyl radical
  • R is selected from the group consisting of ethylene
  • n is an integer of from 0 to 3, said ester mixture containing a major proportion of esters prepared by reacting ethylene glycol monomethyl ether with a mixture of dibasic acids containing approximately -25 percent adipic acid, 45-60 percent glutaric acid and 25-35 percent succinic acid, and a minor proportion of di(triethylene glycol monomethyl ether) adipate.
  • composition includes an organic antioxidant.
  • composition includes an organic corrosion inhibitor.
  • composition includes an organic antioxidant and an organic corrosion inhibitor.
  • component (b) of said composition is a polyoxyalkylene glycol or ether thereof in an amount of from about 5 percent to about 14 percent by weight of said composition.
  • R of the formula for said ester component (a) is selected from the group consisting of methyl and ethyl.
  • R is an alkylene group of two to four carbon atoms.
  • ester or mixture of esters is derived for an acid selected from the group consisting of succinic, glutaric, adipic, azelaic, sebacic, and isosebacic acids and mixtures thereof.
  • component (a) is a mixture of esters of the recited formula, said mixture of esters being derived from a mixture of esters consisting of adipic acid, glutaric acid and succinic acid.
  • the method of claim 14 wherein the mixture of acids consists of approximately 15 to 25 adipic acid, 45 to 60 percent glutan'c acid and 25 to 35 percent succinic acid.
  • said component (a) comprises a mixture of esters prepared by reacting ethylene glycol monomethyl ether with amixture of dibasic acids consisting of 15 to 25 percent adipic acid, 45 to 60 percent glutaric acid, and 25 to 35 percent succinic acid.

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US3779930A (en) * 1970-06-16 1973-12-18 Ici Australia Ltd Fluids
US3914182A (en) * 1970-01-20 1975-10-21 Burmah Oil Trading Ltd Hydraulic fluids
US4260505A (en) * 1978-10-25 1981-04-07 Olin Corporation Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids
US4719025A (en) * 1984-08-07 1988-01-12 Toyota Jidosha Kabushiki Kaisha Synthetic lubrication oil compositions
US5560854A (en) * 1992-09-18 1996-10-01 Nissan Motor Co., Ltd. Working fluid composition for HFC refrigerant compressor containing benzotriazole derivatives, and a process for improving lubrication in a compressor
US5614268A (en) * 1994-12-15 1997-03-25 Varley; Michael J. Coating composition
US5707945A (en) * 1993-09-14 1998-01-13 Unichema Chemie B. V. Base fluids
EP2123249A4 (en) * 2007-02-09 2015-01-14 Kokyu Alcohol Kogyo Co Ltd OIL SOLUTION AND AGENTS, MOISTURE BACKING AGENT AND PREPARATION THEREOF FOR TOPICAL APPLICATION
US9512381B2 (en) 2009-05-05 2016-12-06 Rhein Chemie Rheinau Gmbh Lubricity enhancing additives, a method for producing the same and use thereof
CN110770328A (zh) * 2017-06-28 2020-02-07 陶氏环球技术有限责任公司 低voc润滑剂组合物

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GB1341901A (en) * 1971-01-21 1973-12-25 Burmah Oil Trading Ltd Hydraulic fluids

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US2542785A (en) * 1947-12-29 1951-02-20 Du Pont Hydraulic fluids
US2629693A (en) * 1947-07-01 1953-02-24 Shell Dev Lubricating composition
US2857421A (en) * 1954-10-27 1958-10-21 Exxon Research Engineering Co Reclamation of used synthetic lubricating oils
US2916457A (en) * 1953-12-01 1959-12-08 Hoechst Ag Pressure transmitting fluids for brakes and hydraulic apparatus
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US2629693A (en) * 1947-07-01 1953-02-24 Shell Dev Lubricating composition
US2542785A (en) * 1947-12-29 1951-02-20 Du Pont Hydraulic fluids
US2916457A (en) * 1953-12-01 1959-12-08 Hoechst Ag Pressure transmitting fluids for brakes and hydraulic apparatus
US2857421A (en) * 1954-10-27 1958-10-21 Exxon Research Engineering Co Reclamation of used synthetic lubricating oils
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions
US3274113A (en) * 1963-08-28 1966-09-20 Sun Oil Co Oxidation resistant hydraulic oil

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3914182A (en) * 1970-01-20 1975-10-21 Burmah Oil Trading Ltd Hydraulic fluids
US3779930A (en) * 1970-06-16 1973-12-18 Ici Australia Ltd Fluids
US4260505A (en) * 1978-10-25 1981-04-07 Olin Corporation Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids
US4719025A (en) * 1984-08-07 1988-01-12 Toyota Jidosha Kabushiki Kaisha Synthetic lubrication oil compositions
US5560854A (en) * 1992-09-18 1996-10-01 Nissan Motor Co., Ltd. Working fluid composition for HFC refrigerant compressor containing benzotriazole derivatives, and a process for improving lubrication in a compressor
US5707945A (en) * 1993-09-14 1998-01-13 Unichema Chemie B. V. Base fluids
US5614268A (en) * 1994-12-15 1997-03-25 Varley; Michael J. Coating composition
EP2123249A4 (en) * 2007-02-09 2015-01-14 Kokyu Alcohol Kogyo Co Ltd OIL SOLUTION AND AGENTS, MOISTURE BACKING AGENT AND PREPARATION THEREOF FOR TOPICAL APPLICATION
US9512381B2 (en) 2009-05-05 2016-12-06 Rhein Chemie Rheinau Gmbh Lubricity enhancing additives, a method for producing the same and use thereof
CN110770328A (zh) * 2017-06-28 2020-02-07 陶氏环球技术有限责任公司 低voc润滑剂组合物

Also Published As

Publication number Publication date
DK123038B (da) 1972-05-08
DE1288720B (de) 1969-02-06
AT279787B (de) 1970-03-25
GB1083324A (en) 1967-09-13
NL6507855A (da) 1965-12-20
DE1288720C2 (de) 1975-01-16
BE665653A (da) 1965-10-18

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