US3679587A - Functional fluid compositions containing perfluoro surfactants - Google Patents

Functional fluid compositions containing perfluoro surfactants Download PDF

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US3679587A
US3679587A US18291A US3679587DA US3679587A US 3679587 A US3679587 A US 3679587A US 18291 A US18291 A US 18291A US 3679587D A US3679587D A US 3679587DA US 3679587 A US3679587 A US 3679587A
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phosphate
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Terrill D Smith
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Monsanto Co
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084Acrylate; Methacrylate
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
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    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
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    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids

Definitions

  • This invention relates to functional fluid compositions having the ability to inhibit and control damage to mechanical members of hydraulic systems in contact with said fluid and more particularly to compositions comprising certain phosphate ester functional fluids containing an anionic perfluorinated surfactant in amounts suflicient to inhibit and control damage to mechanical members in a hydraulic system.
  • cavitation can be described as a phenomenon resulting from movement of a fluid at a given pressure to a lower pressure, the lower pressure being obtained by an increase in fluid velocity at a given point or zone in the pressure system.
  • the reduction in pressure is of such a magnitude as to cause cavitation severe enough to damage mechanical members and/ or the fluid.
  • damage herein defined to include damage to a functional fluid and to mechanical members in contact with said fluid
  • damage can be effectively reduced or inhibited in the phosphate ester based functional fluid systems by the incorporation of small amounts of perfluorinated anionic surfactant into a functional fluid.
  • perfluorinated anionic surfactants into phosphate ester based functional fluids improves the ability of such fluids to inhibit damage without adversely affecting the other properties of such fluids such as viscosity, oxidative and thermal stability, corrosion resistance in the presence of metal parts and the lubricating qualities of the functional fluid.
  • the functional fluid compositions of this invention comprise a major amount of (A) liquid phosphate esters and mixtures thereof wherein the phosphate esters are represented by the formula wherein each R is individually an alkyl or alkoxyalkyl group containing from 2 to 12 carbon atoms, phenyl groups and substituted phenyl groups containing up to 20 carbon atoms wherein the substituents are alkyl, phenyl, or phenyl alkyl and wherein the alkyl groups contain from 1 to 10 carbon atoms and (B) a damage inhibiting amount of a perfluorinated anionic surfactant.
  • A liquid phosphate esters and mixtures thereof wherein the phosphate esters are represented by the formula wherein each R is individually an alkyl or alkoxyalkyl group containing from 2 to 12 carbon atoms, phenyl groups and substituted phenyl groups containing up to 20 carbon atoms wherein the substituents are alkyl, phenyl, or phenyl
  • the phosphate ester comprises from 65 to 99.999 percent by weight of the functional fluid compositions of this invention.
  • the functional fluid compositions of this 3 invention can also contain minor amounts, i.e. up to 49% by weight, of other lubricants for example, polyesters, polyphenyl ethers, and the like.
  • the amount of the perfluorinated anionic surfactant employed in the functional fluid compositions of this invention is from as little as 0.001 to as much as 5.0 parts surfactant per 100 parts of the phosphate ester. Amounts greater than 5.0 parts can be employed if soluble in the fluid, however, no commensurate advantages are obtained thereby.
  • the perfluorinated anionic surfactants employed in the compositions of this invention are the alkali metal salts of perfluoroalkyl sulfonic acids and have the general formula (II) R SO M where M is an alkali metal, for example sodium, lithium, potassium, rubidium or cesium and R; is a C F or a cyclic C,,F group where n is an integer of from 1 to 18 and a is an integer from 4 to 18.
  • salts are, for example, potassium perfluoromethane sulfonate, potassium perfluoroethane sulfonate, sodium perfiuorobutane sulfonate, sodium perfluorocyclohexane sulfonate, potassium perfluorooctane sulfonate, cesium perfluorooctadecane sulfonate, potassium perfiuorocyclopentane sulfonate, potassium perfluoropentane sulfonate, and the like. It is preferred that the perfluorinated anionic surfactants contain at least 5 carbon atoms and especially preferred that they contain from 7 to 12 carbon atoms.
  • perfluorinated anionic surfactants which can be employed in the composition of this invention are the alkali metal salts of perfluorinated alkyl disulfonic acids and the like.
  • These disulfonic acid salts are, for example, dipotassium perfiuorocyclohexane disulfonic C F (SO K) dipotassium bis(perfluorocyclohexane sulfonate) and the like.
  • the perfluorinated alkyl groups represented by R include perfluorinated alkyl groups and perfluorinated cycloalkyl groups, for example, perfiuoromethyl, perfluoroethyl, perfiuoropropyl, perfiuorobutyl, perfluoropentyl, perfluoroheptyl, perfiuorooctyl, perfluorodecyl, perfluorooctodecyl, etc.
  • the cycloalkyl groups are, for example, perfluorocyclopentyl, perfiuorocyclohexyl, perfluorocycloheptyl, perfiuoro (ethylcyclohexyl perfiuoro (cyclohexylmethyl) perfiuoro (cyclohexylethyl) perfluoro (cyclohexylpropyl) perfluoro (methylcyclohexyl) perfluoro dimethylcyclohexyl) and the like.
  • the perfiuoroalkyl group contain at least 5 carbon atoms and even more preferred that it contain 7 or more carbon atoms.
  • the preferred esters of phosphoric acid which can be employed as base stocks in the compositions of the instant invention are those wherein the groups represented by R are alkyl, alkoxyalkyl, phenyl or substituted phenyl.
  • the preferred base stocks are hereinafter referred to generically as phosphates and include trialkyl phosphates, triphenyl and/or substituted phenyl phosphates and mixed phenyl and/or substituted phenyl phosphates.
  • the alkyl groups preferred are those containing from 2 to 12 carbon atoms with the total number of carbon atoms in the trialkyl phosphates being from 12 to 36 carbon atoms.
  • alkyl groups are for example, ethyl, propyl, isopropyl, butyl, hexyl, 2-ethylhexyl, dodecyl, decyl, and the like.
  • the substituted phenyl groups represented by the Rs in Formula I are those containing up to 16 carbon atoms and the alkyl groups contain 1 to carbon atoms provided that the total number of carbon atoms in all of the alkyl groups attached to any one phenyl group be at most 10 carbon atoms.
  • the alkoxyalkyl groups are for example, those having the formula H n 2n x a 2a wherein n is an integer having a value of from 1 to 10, a
  • alkoxylalkyl groups are for example methoxyethyl, ethoxyethylpropoxyethyl, ethoxypropyl, ethoxypentyl, propoxydecyl, nonyloxyethyl, octyloxybutyl and the like.
  • the substituted phenyl groups represented by R include the alkyl-substituted phenyl groups and are for example, methylphenyl, ethylphenyl, dimethylphenyl, propylphenyl, nonylphenyl, decylphenyl, dipentylphenyl, butylhexylphenyl and the like. Also included within the definition of the substituted phenyl groups represented by R, are, for example the phenylalkyl phenyl groups (C H C H --C H where n is 1 to 8) containing up to 20 carbon atoms, i.e.
  • phenylmethylphenyl C H CH C H phenylethylphenyl (C H C H C H phenylpropylphenyl (C H C H C H phenyloctylphenyl (C6H5C8H16C6H4 v and the like; and phenyl-substituted phenyl groups such as 0-, mand p-phenylphenyl (C H -C H o-, mand p-methylphenylphenyl (CH C H --C H o-, mand p-dimethylphenylphenyl ((CH C H C H and the like.
  • Typical examples of these phosphate esters are for example, dibutylphenyl phosphate, triphenyl phosphate, tricresyl phosphate, tributyl phosphate, tri-Z-ethylhexyl, trioctyl phosphate, and mixtures of the above phosphates such as mixture of tributyl phosphate and tricresyl phosphate, mixtures of isooctyl diphenyl phosphate and 2-ethy1- hexyl diphenyl phosphate, and mixtures of trialkyl phosphates and tricresyl phosphates and the like.
  • the particularly preferred phosphate esters are those which remain liquid at temperatures of about 30 C.
  • the functional fluid composition of this invention can also contain polymeric viscosity index improvers such as poly(alkylmethacrylate), poly(alkylacrylates), polyoxyalkylenes, polyurethanes and the like.
  • polymeric viscosity index improvers such as poly(alkylmethacrylate), poly(alkylacrylates), polyoxyalkylenes, polyurethanes and the like.
  • the preferred polymeric viscosity index improvers which may be employed in the compositions of this invention are the polymers of alkyl esters of alpha-beta unsaturated monocarboxylic acids having the formula wherein R and R are each individually hydrogen or a C to C alkyl group, and R is a C to C alkyl group. Illustration of the alkyl groups represented by R R and R within their definitions as given above are for example methyl, ethyl, propyl, butyl, t-butyl, isopropyl, 2-ethylhexyl, hexyl, decyl, undecyl, dodecyl and the like.
  • polymers include, for example, poly(butyhnethacrylates), poly('hexylmethacrylates), poly(octylacrylates), poly- (dodecylacrylates) and polymers wherein the ester is a mixture of compounds obtained by esterifying the 04-8 unsaturated monocarboxylic acid with a mixture of monoalcohols containing from 1 to 12 carbon atoms.
  • the polyalkylmethacrylates and acrylates suitable for the purpose of this invention are in general those resulting from the polymerization of alkylmethacrylates or alkylacrylates in which the alkyl groups have from 4 to 12 carbon atoms.
  • the alkyl groups may be mixtures such as derived from a mixture of alcohols in which case there may be included some alkyl groups having as low as 2 carbon atoms and as high as about 18 carbon atoms.
  • the number of carbon atoms in the alkyl group should preferably be such that the polymer is compatible with the particular fluid use. Usually it will be satisfactory for the alkyl group of the methacrylate polymer to be from about 4 to 10 carbon atoms.
  • the alkyl group may be branched chain or isoalkyl, but it is preferably normal alkyl.
  • the molecular weight of the polymerized alkylmethacrylate can be from 15,000 to about 40,000 or the viscosity index improver can be a mixture of one or more polymers having different average molecular weights. For example, a
  • the total amount of viscosity index improver employed in the compositions of the instant invention can range from about 2 to about 20 parts per 100 parts of the total composition.
  • the ratio of high molecular weight viscosity index improver (A) to the lower molecular weight viscosity index improver (B) can be from 1 to 20 to 20 to 1. It is particularly preferred that the ratio of high molecular weight to the low molecular weight polymer be from about 2.5 to 7.5 to 7.5 to 2.5. It is even more preferred that the ratio be from 6 to 4 to 4 to 6.
  • Water can be piesent in the compositions of this invention; however, water is not necessary to obtain the inhibition of erosion of material. As little as 0.1 part of water per 100 parts of the total composition can be employed and can range as high as 2.0 parts per 100 parts of the total composition.
  • the base fluids are designated A, B, C, D and E, respectively.
  • the surfactant is a perfluorinated anionic surfactant which is the potassium salt of the perfiuoroalkane sulfonic acid C F SO K.
  • These base fluids have the following formulations:
  • Tricresyl phosphate 10.9 Tributyl phosphate 79.50 Poly(n-hexylmethacrylate), approximately 5,600
  • the fluids were prepared in the normal manner and the potassium perfluoroalkane sulfonate added in the amount indicated with stirring. The solution was then filtered and the test conducted.
  • valve is placed in a hydraulic system with a fluid supply heated to F. and maintained at a supply pressure of 3000 p.s.i.g.
  • the valve is opened to allow a constant initial flow as indicated with the downside pressure being 1500 p.s.i.g.
  • the test was conducted for 118 hours with the fiow rate being monitored. An increase in flow rate indicates a lack of effectiveness of the fluid to inhibit erosion of material.
  • Valve 1 employed in the test was a Bendix pressure reduction and relief valve of the spool in sleeve type.
  • the holes are drilled and finish reamed and the fiat circular surface is lapped.
  • the blocks are mounted together by a centering pin and held together by four threaded rods and end plates fitted with hydraulic line connecting ports which has zero clearance between the fiat surfaces.
  • the cylindrical blocks are rotated so that the flow rate is approximately 250 cc. per minute and the system operated with a supply pressure of 3000 p.s.i.g. and a down stream pressure of 1500 p.s.i.g.
  • test method as employed to determine relative damage has been found to correlate quite well to actual test runs on simulated hydraulic system test stands, such as the F airey Test Stand.
  • hydraulic system test stands for determining damage have correlated quite well with the hydraulic system of commercial aircraft where damage levels have been determined.
  • Functional fluid compositions of this invention with a viscosity index improver system comprising the mixture of high molecular weight and low molecular weight polymers with water concentrations sufficient to inhibit the control damage have been evaluated in actual hydraulic systems in test stands and commercial aircraft and have been found to effectively inhibit damage and are far superior to the neat fluids with additive amounts of water but employing only a single polymer as the viscosity index improver.
  • improved hydraulic pressure devices can be prepared in accordance with this invention which comprise in combination a fluid chamber and an actuating fluid composition in said chamber, said fluid comprising base stock compositions hereinbefore described.
  • the parts which are so lubricated include the frictional surfaces of the source of power, namely the pump, valves, operating pistons and cylinders, fluid motors, and in some cases, for machine tools, the ways, tables and slides.
  • the hydraulic system may be of either the constant-volume or the variable volume type of system.
  • the pumps may be of various types, including centrifugal pumps, jet pumps, turbine vane, liquid piston gas compressors, piston-type pump, more particularly the variable-stroke piston pump, the variable-discharge or variable displacement piston pump, radial-piston pump or axial-piston pump in which a pivoted cylinder block is adjusted at various angles with the piston assembly, for example, the Vickers Axial-Piston Pump, or in which the mechanism which drives the pistons is set at an angle adjustable with the cylinder block; gear-type pump, which may be spur, helical or herringbone gears, variations of internal gears, or a screw pump; or vane pumps.
  • the valves may be stop valves, reversing valves, pilot valves, throttling valves, sequence valves, relief valves, servo valves, non-return valves, poppet valves or unloading valves.
  • Fluid motors are usually constantor variabledischarge piston pumps caused to rotate by the pressure of the hydraulic fluid of the system with the power supplied by the pump power source. Such a hydraulic motor may be used in connection with a variable-discharge pump to form a variable-speed transmission. It is, therefore, especially important that the frictional parts of the fluid system which are lubricated by the functional fluid be protected from damage. Thus, damage brings about seizure of frictional parts, excessive wear and premature replacement of parts.
  • the fluid compositions of this invention when utilized as a functional fluid can also contain dyes, pour point depressants, metal deactivators, acid scavengers, antioxidants, defoamers in concentration sufficient to impart antifoam properties, such as from about 10 to about 50,000 parts per million, lubricity agents and the like.
  • the componsitions of this invention can also contain up to 2 percent by weight of oxidation and corrosion inhibitors and acid scavengers such as compounds containing one or more epoxide groups in a molecule.
  • oxidation and corrosion inhibitors and acid scavengers such as compounds containing one or more epoxide groups in a molecule.
  • epoxide containing compound containing one epoxy group are, for example, phenylglycidyl ether, glycidylcyclohexyl ether, glycidylalkylcyclohexyl ethers, butadiene monoxide, styrene oxide, 1,2-epoxydodecane, alkylglycidyl ether, 1,2-epoxyoctyloxypropane and the like.
  • Epoxide compounds containing more than one epoxide group per molecule are, for example,
  • a hydraulic fluid composition comprising (I) a major amount of at least about 65 percent by weight of the composition of a phosphate ester and mixtures thereof having the formula wherein each R is individually an alkyl or alkoxyalkyl group containing from 2 to 12 carbon atoms, a phenyl group or a substituted phenyl group containing up to 20 carbon atoms wherein the substituents are phenyl groups, phenyl alkyl groups or alkyl groups wherein the alkyl groups contain from 1 to 10 carbon atoms, and
  • (II) from about 0.001 to about percent by weight of phosphate ester of a perfluorinated anionic surfactant selected from the group consisting of alkali metal salts of perfluoroalkyl sulfonic acid and perfluoroalkyl disulfonic acid wherein the alkyl is from 1 to about 18 carbon atoms.
  • a perfluorinated anionic surfactant selected from the group consisting of alkali metal salts of perfluoroalkyl sulfonic acid and perfluoroalkyl disulfonic acid wherein the alkyl is from 1 to about 18 carbon atoms.
  • composition of claim 1 wherein the surfactant is potassium perfluorooctane sulfonate.
  • composition as claimed in claim 1 wherein the phosphate ester is dibutylphenyl phosphate.
  • composition as claimed in claim 1 wherein the phosphate ester is tributyl phosphate.
  • composition as claimed in claim 1 wherein the phosphate ester is a mixture of tributyl phosphate and tricresyl phosphate.
  • composition as claimed in claim 1 wherein the phosphate ester is a mixture of a trialkyl phosphate and cresyldiphenyl phoosphate.
  • composition as in claim 2 wherein the phosphate ester is tributyl phosphate.
  • composition as in claim 2 wherein the phosphate ester is dibutylphenyl phosphate.
  • composition as in claim 2 wherein the phosphate ester is a mixture of tributyl and tricresyl phosphate.
  • composition as in claim 2 wherein the phosphate ester is a trialkyl phosphate and cresyldiphenyl phosphate.
  • a composition of claim 1 wherein the perfluorinated anionic surfactant has the structure wherein M is an alkali metal, m is an integer of 1 or 2, and R; is a C,,F or a cyclic C F group wherein n is an integer of from 1 to about 18, and a is an integer of from about 4 to 18.
  • a hydraulic fluid composition comprising (I) a major amount of at least about 65 percent by weight of the composition of a phosphate ester and mixtures thereof having the formula wherein each R is individually an alkyl or alkoxyalkyl group containing from 2 to 12 carbon atoms, a phenyl group or a substituted phenyl group containing up to 20 carbon atoms wherein the substituents are phenyl groups, phenyl alkyl groups or alkyl groups wherein the alkyl groups contain from 1 to 10 carbon atoms, and
  • (II) from about 0.001 to about 5 percent by weight of phosphate ester of a perfluorinated anionic surfactant selected from the group consisting of alkali metal salts of perfluoroalkyl sulfonic acid and perfiuoroalkyl disulfonic acid wherein the alkyl is from 1 to about 18 carbon atoms, and
  • a composition of claim 14 wherein the viscosity index improved is a mixture of (A) from 1 to 20 parts of a high molecular weight polymer having an average molecular weight of from 15,000 to 40,000, and
  • (B) from 1 to 20 parts of a low molecular weight polymer having an average molecular weight of from 2,000 to 12,000.
  • composition of claim 15 wherein (A) and (B) are polyalkylmethacrylates wherein the alkyl groups are of 4 to 10 carbon atoms.
  • composition of claim 16 wherein the phosphate ester is dibutylphenyl phosphate.
  • a composition of claim 17 containing up to about 2 percent by weight of 3,4-epoxycyclohexylmethyl-3,4'- epoxycyclohexanecarboxylate.

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Cited By (22)

* 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
US3941562A (en) * 1973-06-04 1976-03-02 Calgon Corporation Corrosion inhibition
US4302346A (en) * 1979-06-28 1981-11-24 Chevron Research Company Erosion-inhibited functional fluid
US4324674A (en) * 1980-08-28 1982-04-13 Chevron Research Company Amine salt stabilized phosphate ester-based functional fluid
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
WO1993025641A1 (fr) * 1992-06-11 1993-12-23 Monsanto Company Liquide fonctionnel
US5314643A (en) * 1993-03-29 1994-05-24 Betz Laboratories, Inc. High temperature corrosion inhibitor
US5344652A (en) * 1990-04-05 1994-09-06 Minntech Corporation Anticorrosive microbicide
WO1996017517A1 (fr) * 1994-12-09 1996-06-13 Chevron U.S.A. Inc. Liquides hydrauliques pour aeronef
US5817606A (en) * 1996-08-08 1998-10-06 Rohm And Haas Company Viscosity index improving additives for phosphate ester-containing hydraulic fluids
US6030543A (en) * 1993-03-04 2000-02-29 Great Lakes Chemical Corporation Aircraft hydraulic fluid basestocks
WO2000024848A1 (fr) * 1998-10-23 2000-05-04 Exxonmobil Research And Engineering Company Solutions a base d'ester phosphorique et fluide hydraulique d'aeronef les comprenant
USRE37101E1 (en) * 1992-06-11 2001-03-20 Solutia Inc. Stabilized phosphate ester-based functional fluid compositions
US6254799B1 (en) 1998-11-10 2001-07-03 Exxonmobil Research And Engineering Company Phosphate ester base stocks comprising mixed n-butyl/isobutyl phosphate esters and aircraft hydraulic fluids comprising the same
US6319423B1 (en) 1998-10-23 2001-11-20 Exxonmobil Research & Engineering Co. Phosphate ester base stocks and aircraft hydraulic fluids comprising the same
WO2002086035A1 (fr) * 2001-04-20 2002-10-31 Exxonmobil Research And Engineering Company Fluides fonctionnels favorisant la resistance a l'erosion des servovalves
US6599866B2 (en) 2001-04-20 2003-07-29 Exxonmobil Research And Engineering Company Servo valve erosion inhibited aircraft hydraulic fluids
US6703355B2 (en) 2000-08-04 2004-03-09 Exxonmobil Research And Engineering Company Method for lubricating high pressure hydraulic system using phosphate ester hydraulic fluid
US20040127370A1 (en) * 2002-11-15 2004-07-01 Poirier Marc Andre Hydraulic fluids with erosion resistance
US20060229225A1 (en) * 2005-01-11 2006-10-12 Clean Earth Technologies, Llc Peracid/peroxide composition and use thereof as an anti-microbial and a photosensitizer
US20060278846A1 (en) * 2005-06-14 2006-12-14 Wolfe Terry C High performance phosphate ester hydraulic fluid
WO2017099956A1 (fr) 2015-12-07 2017-06-15 Exxonmobil Research And Engineering Company Compositions de fluide fonctionnel contenant des inhibiteurs d'érosion

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3941562A (en) * 1973-06-04 1976-03-02 Calgon Corporation Corrosion inhibition
US3932294A (en) * 1974-01-11 1976-01-13 Chevron Research Company Functional fluid containing a hydrolysis suppressor
US4302346A (en) * 1979-06-28 1981-11-24 Chevron Research Company Erosion-inhibited functional fluid
US4324674A (en) * 1980-08-28 1982-04-13 Chevron Research Company Amine salt stabilized phosphate ester-based functional fluid
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
US5344652A (en) * 1990-04-05 1994-09-06 Minntech Corporation Anticorrosive microbicide
USRE37101E1 (en) * 1992-06-11 2001-03-20 Solutia Inc. Stabilized phosphate ester-based functional fluid compositions
RU2167921C2 (ru) * 1992-06-11 2001-05-27 Солютия Инк. Авиационная гидравлическая жидкость (варианты)
US5464551A (en) * 1992-06-11 1995-11-07 Monsanto Company Stabilized phosphate ester-based functional fluid compositions
WO1993025641A1 (fr) * 1992-06-11 1993-12-23 Monsanto Company Liquide fonctionnel
US6030543A (en) * 1993-03-04 2000-02-29 Great Lakes Chemical Corporation Aircraft hydraulic fluid basestocks
US5314643A (en) * 1993-03-29 1994-05-24 Betz Laboratories, Inc. High temperature corrosion inhibitor
WO1996017517A1 (fr) * 1994-12-09 1996-06-13 Chevron U.S.A. Inc. Liquides hydrauliques pour aeronef
US5817606A (en) * 1996-08-08 1998-10-06 Rohm And Haas Company Viscosity index improving additives for phosphate ester-containing hydraulic fluids
US5863999A (en) * 1996-08-08 1999-01-26 Rohm And Haas Company Viscosity index improving additives for phosphate ester-containing hydraulic fluids
US6319423B1 (en) 1998-10-23 2001-11-20 Exxonmobil Research & Engineering Co. Phosphate ester base stocks and aircraft hydraulic fluids comprising the same
US6649080B2 (en) 1998-10-23 2003-11-18 Exxonmobil Research And Engineering Company Phosphate ester base stocks and aircraft hydraulic fluids comprising the same
WO2000024848A1 (fr) * 1998-10-23 2000-05-04 Exxonmobil Research And Engineering Company Solutions a base d'ester phosphorique et fluide hydraulique d'aeronef les comprenant
US6254799B1 (en) 1998-11-10 2001-07-03 Exxonmobil Research And Engineering Company Phosphate ester base stocks comprising mixed n-butyl/isobutyl phosphate esters and aircraft hydraulic fluids comprising the same
US6652772B2 (en) 1998-11-10 2003-11-25 Exxonmobil Research And Engineering Company Phosphate ester base stocks comprising mixed n-butyl/isobutyl phosphate esters and aircraft hydraulic fluids comprising the same
US6703355B2 (en) 2000-08-04 2004-03-09 Exxonmobil Research And Engineering Company Method for lubricating high pressure hydraulic system using phosphate ester hydraulic fluid
US20030040443A1 (en) * 2001-04-20 2003-02-27 Poirier Marc Andre Functional fluids with servo valve erosion resistance
US6599866B2 (en) 2001-04-20 2003-07-29 Exxonmobil Research And Engineering Company Servo valve erosion inhibited aircraft hydraulic fluids
WO2002086035A1 (fr) * 2001-04-20 2002-10-31 Exxonmobil Research And Engineering Company Fluides fonctionnels favorisant la resistance a l'erosion des servovalves
US20040127370A1 (en) * 2002-11-15 2004-07-01 Poirier Marc Andre Hydraulic fluids with erosion resistance
US20060229225A1 (en) * 2005-01-11 2006-10-12 Clean Earth Technologies, Llc Peracid/peroxide composition and use thereof as an anti-microbial and a photosensitizer
US8110538B2 (en) 2005-01-11 2012-02-07 Biomed Protect, Llc Peracid/peroxide composition and use thereof as an anti-microbial and a photosensitizer
US20060278846A1 (en) * 2005-06-14 2006-12-14 Wolfe Terry C High performance phosphate ester hydraulic fluid
US7582225B2 (en) 2005-06-14 2009-09-01 Solutia, Inc. High performance phosphate ester hydraulic fluid
WO2017099956A1 (fr) 2015-12-07 2017-06-15 Exxonmobil Research And Engineering Company Compositions de fluide fonctionnel contenant des inhibiteurs d'érosion

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GB1301056A (en) 1972-12-29
BE763986A (fr) 1971-09-09
DE2111174B2 (de) 1978-11-02
NL149849B (nl) 1976-06-15
JPS5128074B1 (fr) 1976-08-17
DE2111174A1 (de) 1971-09-23
FR2084372A5 (fr) 1971-12-17
DE2111174C3 (de) 1979-07-12
NL7103046A (fr) 1971-09-14
CA949546A (en) 1974-06-18

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