US3707501A - Hydraulic fluids containing certain quaternary phosphonium salts of phosphorus acids - Google Patents

Hydraulic fluids containing certain quaternary phosphonium salts of phosphorus acids Download PDF

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Publication number
US3707501A
US3707501A US51001A US3707501DA US3707501A US 3707501 A US3707501 A US 3707501A US 51001 A US51001 A US 51001A US 3707501D A US3707501D A US 3707501DA US 3707501 A US3707501 A US 3707501A
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Prior art keywords
alkyl
phosphate
methyl
butyl
dimethyl
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US51001A
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William F Gentit
Fred Jaffe
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Akzo America Inc
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Stauffer Chemical Co
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Assigned to AKZO AMERICA INC., A CORP. OF DE reassignment AKZO AMERICA INC., A CORP. OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: STAUFFER CHEMICAL COMPANY
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
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    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • R 69 INK Y 9 [has] [H fill! YII where R, R and R" represent alkyl, aryl, alkaryl, and aralkyl groups containing from 1 to 10 carbon atoms, and R' represents alkyl or aralkyl containing from 1 to 10 carbon atoms, X represents 0 or S, Y and Y" represent alkoxy, alkylthio, alkyl, aryl, alkaryl, aralkyl, aryloxy, arylthio and alkaryloxy, and Z represents oxygen Typical compounds are illustrated as follows:
  • Such salts have been found useful as polymerization catalysts, antistatic agents, stabilizers, surfactants, and in baths for dying textile materials. These compounds and further literature thereon are available from the Carlisle Chemical Works, Inc., Reading, Ohio, as shown in Chemical Engineering News, vol. 47, No. 1, at page 7 (January 1969).
  • Lubricant compositions to which the phosphonium compositions can be added are referred to as base stocks. They include, but are not limited to, esters and amides of an acid of phosphorus, mineral oil and synthetic hydrocarbon oil base stocks, hydrocarbyl silicates, silicones, aromatic ether and thioether compounds, chlorinated biphenyl, monoesters, dicarboxylic acid esters, esters of polyhydric compounds, polyalkylene ether glycols and alcohols as well as their esters.
  • the concentration of phosphonium composition required to inhibit damage will vary depending upon the particular base stock or blend of base stocks which are employed. Preferably, between about 0.1 and about 10% by weight of the phosphonium composition is employed. More preferably, between about 0.5 and about 2.0 weight percent is employed.
  • the functional fluid composition of this invention can be compounded in any manner known R( )n 1)n wherein Y is selected from the group consisting of oxygen, sulfur and Y is selected from the group consisting of oxygen, sulfur and and Y is selected from the group consisting of oxygen, sulfur and R, R R R R and R are each selected from the group consisting of alkyl, aryl, substituted aryl and substituted alkyl wherein R, R R R R and R each can be identical or different with respect to any other radical, and a, b and c are whole numbers having a value of 0 to 1 and the sum of a+b+c is from 1 to 3.
  • alkyl radicals are as follows: methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal amyl, isoamyl, Z-methylbutyl, 2,2-dimethyl propyl, l-methyl butyl, diethylmethyl, 1,2-dimethyl propyl, tertiary amyl, normal hexyl, l-methylamyl, l-ethyl butyl, 1,2,2-trimethyl propyl, 3,3-dimethyl butyl, 1,1,2-trimethyl propyl, Z-methyl amyl, 1,1-dimethyl butyl, l-ethyl Z-methyl propyl, 1,3-dimethyl butyl, isohexyl, 3-methylarnyl, 1,2-dimethy1 butyl, 1- methyl l-ethyl propyl, 2-ethyl,
  • aralkyl groups e.g., benzyl, alphaor beta-phenylethyl, alpha-alpha dimethyl benzyl and the like.
  • cyclohexyl, cycloheptyl and the like are also included.
  • Typical examples of substituted alkyl radicals are the haloalkyl radicals which can be represented by the structure:
  • Hal refers to a halogen
  • m is less than or equal to 2n+1 and It may have any value from 0 to 18, and R and R can be hydrogen, halogen or alkyl radicals.
  • Preferred radicals are those where Hal is fiuoro and include those represented by the following formulas:
  • fluorine-containing radicals include fluorinated alkoxyalkyl radicals particularly those represented by the following formulas:
  • aryl and substituted aryl radicals are phenyl, cresyl, xylyl, halogenated phenyl, allcoxylated phenyl, cresyl and xylyl in which the available hydrogen on the aryl or substituted aryl is partially or totally replaced by a halogen, mand p-trifiuoromethylphenyl, o-, mand p-2,2,2-trifiuoroethylphenyl, o-, m and p3,3,3- trifiuoropropylphenyl and o-, m-, and p-4,4,4-trifluorobutylphenyl.
  • the orthosilicates useful as base stocks include the tetraalkyl orthosilicates such as tetra(octyl)orthosilicates, tetra (2-ethylhexyl)orothosilicates and the tetra(isooctyl) orthosilicates and those in which the isooctyl radicals are obtained from isooctyl alcohol which is derived from the oxo process, and the (trialkoxysilico)trialkyl orthosolicates, otherwise referred to as hexa(alkoxy) disiloxanes, such as hexa(2-ethylbutoxy) disiloxane and hexa(2-ethylhexoxy) disiloxane.
  • hexa(alkoxy) disiloxanes such as hexa(2-ethylbutoxy) disiloxane and hexa(2-ethylhexoxy)
  • the preferred tetraalkyl orthosilicates and hexa(alkoxy) disiloxanes are those in which the alkyl or alkoxy radicals have from 4 to 12 carbon atoms and in which 6 the total number of carbon atoms in the orthosilicate is from 16 to 60.
  • hexa(alkoxy) disiloxanes in addition to the hexa(alkoxy) disiloxanes referred to above, other hexa(alkoxy) disiloxanes can be used in which the aliphatic radical of the alkoxy groups are for example, l-ethylpropyl, 1,3-dimethylbutyl, Z-methylpentyl, l-methylhexyl, l-ethylpentyl, Z-butylhexyl and l-methyl- 4-ethy1octyl.
  • the orthosilicates and alkoxy polysiloxanes can be represented by the general structure:
  • R R and R each can be alkyl, substituted alkyl, aryl, substituted aryl and can be identical or different with respect to any other radical, O is oxygen, Si is silicon, X is a member of the group consisting of carbon and silicon, m is a whole number having a value of 0 or 1, n is an integer having a value of from 1 to about 200 or more and when X is carbon, m is 0, n is l and R R and R each can be hydrogen, alkyl, substituted alkyl, aryl and substituted aryl radicals and when X is silicon m is 1, n is an integer having a value of from 1 to about 200 or more and R R and R each can be alkyl, substituted alkyl, aryl and substituted aryl.
  • substituted aryl radicals are o-, mand p-chlorophenyl, o-, mand p-bromophenyl, o-, mand p-fluorophenyl, alpha,alpha,alpha-trichlorocresyl, alpha,alpha,alpha-trifluorocresyl, xylyl and o-, mand pcresyl.
  • alkyl and haloalkyl radicals are those heretofore described.
  • siloxanes or silicones useful as base stocks are represented by the general structure:
  • R R R R R and R can each be alkyl, substituted alkyl, aryl and substituted aryl radicals and n is a whole number from about 0 to about 2000 or more.
  • alkyl and haloalkyl radicals are those heretofore described.
  • Typical examples of the siloxanes are poly(methyl)siloxane, poly(methyl, phenyl)siloxane, po1y(methyl, chlorophenyl)siloxane and poly(methyl, 3 ,3 ,3-trifluoropropyl siloxane.
  • Dicarboxylic acid esters which are suitable as base stocks are represented by the structure:
  • R and R are each selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl and R is a divalent radical selected from the group consisting of alkylene and substituted alkylene, and are prepared by esterifying dicarboxylic acids such as adipic acid, azelaic acid, suberic acid, sebacic acid, hydroxysuccinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, 2-ethylhexyl alcohol, dodecyl alcohol, 2,2-dimethyl heptanol, 1-methyl cyclohexyl methanol, etc.
  • dicarboxylic acids such as adipic acid, azelaic acid, suberic acid, sebacic acid, hydroxysuccinic acid, fumaric acid, maleic acid, etc.
  • alcohols such as butyl alcohol, hexyl alcohol, 2-ethylhexy
  • alkyl, aryl substituted alkyl and substituted aryl radicals are given above.
  • Polyesters which are suitable as base stocks are represented by the structure:
  • R is selected from the group consisting of hydrogen and alkyl
  • R and R are each selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl
  • a is a whole number having a value of 0 to 1
  • Z is a whole number having a value of l to 2 and when Z is 1
  • R is selected from the group consisting of hydrogen, alkyl acyloxy and substituted acyloxy and when Z is 2
  • R is oxygen, and are prepared by esterifying such polyalcohols as pentaerythritol, dipentaerythritol, trimethylolpropane, trimethylolethane and neopentyl glycol with such acids as propionic, butyric, isobutyric, n-valeric, caproic, n-heptylic, caprylic, Z-ethylhexanoic, 2,2-dimethylheptanoic and pelargonic.
  • esters which are also suitable as base stocks are the mono esters.
  • A, A A and A are each a chalcogen having an atomic number of 8 to 16, X, X X X and X each are selected from the group consisting of hydrogen, alkyl, haloalkyl, halogen, arylalkyl and substituted arylalkyl, m, n and 0 are whole numbers, each having a value of 0 to 8 and a is a whole number having a value of 0 to 1 provided that when a is 0, n can have a value of 1 to 2.
  • Typical examples of alkyl and substuted alkyl radicals are given above.
  • Typical examples of such base stocks are 2- to 7-ring ortho-, metaand para-polyphenyl ethers and mixtures thereof, 2- to 7-ring ortho-, metaand para-polyphenyl thioethers and mixtures thereof, mixed polyphenyl ether-thioether compounds in which at least one of the chalcogens represented by A, A A and A is dissimilar with respect to any one of the other ehalcogens, dihalogenated diphenyl ethers, such 18S 4-bromo-3'-chlorodiphenyl ethers and bisphenoxy biphenyl compounds and mixtures thereof.
  • Hydrocarbon oils including mineral oils derived from petroleum sources and synthetic hydrocarbon oils are suitable base stocks.
  • the physical characteristics of functional fluids derived from a mineral oil are selected on the basis of the requirements of the fluid systems and therefore this invention includes as base stocks mineral oils having a wide range of viscosities and volatilities such as naphthenic base, paraffinic base and mixed base mineral oils.
  • the synthetic hydrocarbon oils include but are not limited to those oils derived from oligomerization of olefins such as polybutenes and oils derived from high 8 alpha olefins of from 4 to 20 carbon atoms by acid catalyzed dimerization and by oligomerization using trialuminum alkyls as catalysts.
  • Chlorinated biphenyls are also useful as base stocks.
  • the fluid compositions of this invention when utilized as a functional fluid can also contain acid acceptors, dyes pour point depressants, antioxidants, antifoam agents, viscosity index improvers such as polyalkyl acrylates, polyalkyl methacrylates, polycyclic polymers, polyurethanes, polyalkylene oxides and polyesters, lubricity agents, water and the like.
  • acid acceptors dyes pour point depressants
  • antioxidants antifoam agents
  • viscosity index improvers such as polyalkyl acrylates, polyalkyl methacrylates, polycyclic polymers, polyurethanes, polyalkylene oxides and polyesters, lubricity agents, water and the like.
  • the base stocks as aforementioned can be utilized singly or as a fluid composition containing two or more base stocks in varying proportions.
  • the base stocks can also contain other fluids which include, in addition to the functional fluids, desired fluids derived from coal products, synthetics, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof), alkylene oxide type polymers (e.g., propylene oxide polymers), and derivatives including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohol, e.g., ethyl alcohol, alkyl benzenes, e.g., monoalkyl benzene such as dodecyl benzene, tetradecyl benzene, etc.) and dialkyl benzene (e.g., n-nonyl Z-ethyl hexyl benzene);
  • the phosphonium composition of the present invention is combined with a phosphate functional fluid base stock.
  • the base stock will consist primarily of trialkylphosphates being present in amounts from 50 to by weight and preferably from 65 to 75% by weight.
  • the trialkylphosphates which give optimum results are those wherein each of the alkyl group contains from 3 to 12 carbon atoms, preferably from 4 to 9 carbon atoms.
  • the alkyl groups should be of a straight chain configuration.
  • a single trialkyl phosphate may contain the alkyl group in all three positions or may possess a mixture of different alkyl groups. Mixtures of various trialkyl phosphates can be used.
  • Suitable species of trialkyl phosphates which may be employed as the base stock composition include tripropyl phosphates, ,tributyl phosphates, trihexyl phosphates, trioctyl phosphates, dipropyl octyl phosphates, dibutyl octyl phosphates, dipropyl hexyl phosphate, dihexyl octyl phosphate, dihexyl propyl phosphate, and propyl butyl octyl phosphate.
  • the trialkyl phosphates can be combined with at least one triaryl phosphate comprising tricresyl phosphate, trixylenyl phosphate, ethyl phenyl dicresyl phosphate or isopropylphenyl diphenyl phosphate, phenyl-bis 4-alphameth ylbenzylphenyl) phosphate.
  • triaryl phosphate comprising tricresyl phosphate, trixylenyl phosphate, ethyl phenyl dicresyl phosphate or isopropylphenyl diphenyl phosphate, phenyl-bis 4-alphameth ylbenzylphenyl) phosphate.
  • tricresyl phosphate and trixylenyl phosphate are employed.
  • the triarylv phosphates in this instance function as a thickener for the trialkyl phosphates.
  • the amount of tricresyl phosphate may range between 0 and 25% by weight while the trixylenyl phosphate may range between 0 and 25% by weight.
  • the preferred range of the triaryl phosphates will be from 5 to 15% tricresyl phosphate and from 5 to 15 by weight trixylenyl phosphate.
  • the combined mixture of tricresyl phosphate and trixylenyl phosphate are blended togetherto provide a viscosity of between 145 and 230 Saybolt Universal Seconds measured at F. This blend of materials can then be combined with a trialkyl phosphate in any known manner.
  • a conventional polymeric material is then blended with a mixture of trialkyl phosphate and triaryl phosphate material which functions as a viscosity index improver.
  • polymeric material suitable with the present invention can be a mixture of from 10 to 55% by weight polymethacrylates, polyacrylates, each containing an alkyl moiety having from 1 to 20 carbon atoms.
  • the polymeric materials may be within a solvent carrier such as di-2-ethylhexyl sebacate, dioctyl adipate, di-2-ethyl hexyl adipate, or other conventional carriers.
  • the polymeric materials may be any combination of these materials. This material is thoroughly blended with a combination of ingredients to form a uniform material. The amount of material incorporated therein may range between 5 and 20% by weight.
  • a rust inhibitor with a solvent carrier such as an alkyl succinate acid and their derivatives
  • a corrosion inhibitor such as benzotriaz ole, quinizarin or the like in an amount ranging between 0.001 and 0.5% by weight is added to the mixture and thoroughly blended therewith.
  • a dye which may range between 5 and 20 parts per million is added thereto and blended therewith in a conventional manner.
  • a silicone antifoaming agent is added thereto and can be present in an amount ranging between 5 and 50 parts per million.
  • Example 1 A base stock material consisting of tricresyl phosphate in an amount of 10.45 weight percent is thoroughly blended with 8.55 weight percent of trixylenyl phosphate to attain a viscosity of 155 Saybolt Universal Seconds measured at 100 F. This blend of materials is blended with 68.96 weight percent of tributyl phosphate until the materials are thoroughly intermixed. Thereafter, 12 weight percent of a mixture of about 40% of a polyalkyl methacrylate and about 60% di-2-ethyl hexyl sebacate solvent carrier are thoroughly blended therewith. 3,4- epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate is blended into the mixture at an additive level of 1.0% by weight.
  • a conventional alkyl succinic acid rust inhibitor in an amount of 0.02 weight percent within a solvent carrier is blended therewith.
  • 0.02 weight percent of benzotriazole is thoroughly blended therewith along with a conventional dye and antifoam agent in an amount of parts per million and 15 parts per million, respectively.
  • trioctylmethylphosphonium dimethyl phosphate is blended into the mixture at various additional levels including 5%, 3%, 1.0% and 0.5% by Weight.
  • Example 1 The compositions described in Example 1 as well as other compositions were tested in the apparatus hereinafter described.
  • the apparatus is a modified Boeing wear apparatus designed to simulate the constricted fiow in the servo valve of an aircraft hydraulic system.
  • the apparatus consists of an air-driven piston-type hydraulic pump, accumulator, filter, flow meter, heat exchanger, reservoir and wear device.
  • the wear device is constructed of 52100 steel hardened to R 62. The fluid enters the device through a 0.085 inch I.D. nozzle at 2500 p.s.i.g. and 0.15 g.p.m. and impinges on a flat plate 0001 inch from the noozle
  • the wear device is disassembled after 24 test hours and the amount of wear on the fiat plate is visually estimated with the naked eye and with the aid of a microscope The results are as follows:
  • Typical phosphonium compounds 2 through 16 hereinabove described when incorporated in the phosphate ester base stock of Example 1 also reduce the wear characteristics of the fluid.
  • the phosphonium compounds described herein are useful in a wide range of lubricant compositions.
  • lubricant as employed herein is intended to include fluids employed primarily for their lubricity as well as those employed as pressure transmission agents.
  • the phosphonium compounds areuseful as extreme pressure additives in fluids including aircraft gas turbine lubricants, as additives in fire-resistant industrial lubricants including gear and cutting oils and in brake fluids.
  • a hydraulic fluid which comprises:
  • a major amount of a base stock material selected from the group consisting of the esters and amides of an acid of phosphorus, mineral oils, synthetic hydrocarbon oils, orthosilicates, alkoxy polysiloxanes, silicones, polyphenyl ethers, polyphenyl thioethers, chlorinated biphenyls, esters of dicarboxylic acids and monohydric alcohols, esters of monocarboxylic acids and monohydric alcohols, esters of monocarboxylic acids and polyhydric alcohols, and mixtures thereof, polyalkylene ether alcohols and esters thereof, and
  • R, R and R" each represent alkyl, aryl, alkaryl and aralkyl groups containing from 1 to 10 carbon atoms
  • R'" represents alkyl or aralkyl groups containing from 1 to 10 carbon atoms
  • X represents an oxygen or sulfur atom
  • Y and Y" represent lower alkoxy, lower alkyl, phenyl lower alkylphenyl, phenyl lower alkyl, phenoxy and lower alkylphenoxy
  • Z represents oxygen
  • composition in accordance with claim 1 wherein said base stock material is selected from the group of esters and amides of an acid of phosphorus having the formula:
  • Y is selected from the group consisting of oxygen, sulfur and l a N Y is selected from the group consisting of oxygen, sulfur and Y is selected from the group consisting of oxygen, sulfur and R, R R R R and R are each selected from the group consisting of alkyl, aryl, substituted aryl and substituted alkyl; and a, b and c are Whole numbers having a value of to 1 such that the sum a+b+c has a value from 1 to 3.
  • a composition in accordance with claim 2 wherein said ester of an acid of phosphorus is a trialkyl phosphate.
  • a composition in accordance with claim 2 wherein said ester of an acid of phosphorus is a mixture of trialkyl phosphates and triaryl phosphates.
  • composition in accordance with claim 4 wherein said trialkyl phosphates are present in an amount between about 50 and about 90% by weight and said triaryl phosphates are present in an amount up to about 50% by weight.
  • composition in accordance with claim 1 containing an alkyl succinate rust inhibitor admixed therewith.
  • a composition in accordance with claim 1 containing a corrosion inhibitor admixed therewith, said corrosion inhibitor being selected from the group consisting of benzotriazole and quinizarin.
  • a composition in accordance with claim 10 wherein said corrosion inhibitor is benzotriazole.
  • composition in accordance with claim 1 containing a 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate acid acceptor.
  • a composition in accordance with claim 2 containing a dye and a silicone antifoaming agent admixed therewith.
  • composition of claim 1 wherein Y and Y" are selected from the group consisting of lower alkyl and phenyl.
  • composition of claim 1 wherein said phosphonium compound is methyltrioctylphosphonium dimethyl phosphate.
  • a method of operating a hydraulic pressure device wherein a displacing force is transmitted to a displaceable member by means of a hydraulic fluid comprising a major amount of base stock material selected from the group consisting of the esters and amides of an acid of phosphorus, mineral oils, synthetic hydrocarbon oils, orthosilicate, alkoxy polysiloxanes, silicones, polyphenyl ethers, polyphenyl thioethers, chlorinated biphenyls, esters of dicarboxylic acids and monohydric alcohols, esters of monocarboxylic acids and monohydric alcohols and esters of monocarboxylic acids and polyhydric alcohols and mixtures thereof, polyalkylene ether alcohols and esters thereof, and a wear inhibiting amount of a phosphonium compound in accordance with the formula:
  • R, R' and R" each represent alkyl aryl, alkaryl or aralkyl group containing from 1 to 10 carbon atoms, and R"' represents alkyl or aralkyl groups containing from 1 to 10 carbon atoms
  • X represents oxygen or sulfur
  • Y and Y" represent lower alkoxy, lower alkyl, phenyl, lower alkylphenyl, phenyl lower alkyl, phenoxy and lower alkylphenoxy
  • Z represents oxygen

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  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US51001A 1970-06-29 1970-06-29 Hydraulic fluids containing certain quaternary phosphonium salts of phosphorus acids Expired - Lifetime US3707501A (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932294A (en) * 1974-01-11 1976-01-13 Chevron Research Company Functional fluid containing a hydrolysis suppressor
US4088591A (en) * 1972-09-18 1978-05-09 General Electric Company Silicone fluid useful as a brake fluid
US4252662A (en) * 1974-02-11 1981-02-24 Stauffer Chemical Company Functional fluids containing ammonium salts of phosphorus acids
US5205951A (en) * 1987-06-30 1993-04-27 Chevron Research And Technology Company Phosphate ester-based functional fluids containing an epoxide and a compatible streaming potential-inhibiting metal salt
US6214777B1 (en) 1999-09-24 2001-04-10 Ecolab, Inc. Antimicrobial lubricants useful for lubricating containers, such as beverage containers, and conveyors therefor
WO2003020843A1 (en) * 2001-09-05 2003-03-13 Cytec Canada Inc. Composition comprising phosphonium salts and their use
US6599866B2 (en) 2001-04-20 2003-07-29 Exxonmobil Research And Engineering Company Servo valve erosion inhibited aircraft hydraulic fluids
US20040127370A1 (en) * 2002-11-15 2004-07-01 Poirier Marc Andre Hydraulic fluids with erosion resistance
EP2126013A1 (en) * 2006-12-19 2009-12-02 Castrol Limited Lubricating oil compositions and uses
US20150232777A1 (en) * 2014-02-20 2015-08-20 Ut-Battelle, Llc Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8507419B2 (en) 2010-03-08 2013-08-13 Basf Se Salts of thiophosphoric acids and use thereof in lubricants
EP2545061B1 (de) 2010-03-08 2014-07-09 Basf Se Salze von thiophosphorsäuren und deren verwendung in schmierstoffen

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4088591A (en) * 1972-09-18 1978-05-09 General Electric Company Silicone fluid useful as a brake fluid
US3932294A (en) * 1974-01-11 1976-01-13 Chevron Research Company Functional fluid containing a hydrolysis suppressor
US4252662A (en) * 1974-02-11 1981-02-24 Stauffer Chemical Company Functional fluids containing ammonium salts of phosphorus acids
US5205951A (en) * 1987-06-30 1993-04-27 Chevron Research And Technology Company Phosphate ester-based functional fluids containing an epoxide and a compatible streaming potential-inhibiting metal salt
US6214777B1 (en) 1999-09-24 2001-04-10 Ecolab, Inc. Antimicrobial lubricants useful for lubricating containers, such as beverage containers, and conveyors therefor
US6599866B2 (en) 2001-04-20 2003-07-29 Exxonmobil Research And Engineering Company Servo valve erosion inhibited aircraft hydraulic fluids
WO2003020843A1 (en) * 2001-09-05 2003-03-13 Cytec Canada Inc. Composition comprising phosphonium salts and their use
US20040127370A1 (en) * 2002-11-15 2004-07-01 Poirier Marc Andre Hydraulic fluids with erosion resistance
EP2126013A1 (en) * 2006-12-19 2009-12-02 Castrol Limited Lubricating oil compositions and uses
US20100093577A1 (en) * 2006-12-19 2010-04-15 Craig Ritchie Lubricting oil compositions and uses
US20150232777A1 (en) * 2014-02-20 2015-08-20 Ut-Battelle, Llc Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives
US9957460B2 (en) * 2014-02-20 2018-05-01 Ut-Battelle, Llc Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives
US20180208869A1 (en) * 2014-02-20 2018-07-26 Ut-Battelle, Llc Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives
US10435642B2 (en) * 2014-02-20 2019-10-08 Ut-Battelle, Llc. Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives

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ZA713389B (en) 1972-01-26
IL36930A (en) 1974-03-14
NO131462C (enrdf_load_stackoverflow) 1975-06-04
BE769225A (fr) 1971-12-29
FR2096564B1 (enrdf_load_stackoverflow) 1975-07-11
FR2096564A1 (enrdf_load_stackoverflow) 1972-02-18
EG10516A (en) 1976-04-30
SU404274A3 (enrdf_load_stackoverflow) 1973-10-26
CA969528A (en) 1975-06-17
GB1310801A (en) 1973-03-21
NL7108962A (enrdf_load_stackoverflow) 1971-12-31
NO131462B (enrdf_load_stackoverflow) 1975-02-24
SE374760B (enrdf_load_stackoverflow) 1975-03-17
IL36930A0 (en) 1971-07-28
CH563448A5 (enrdf_load_stackoverflow) 1975-06-30

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