US3859218A - Lubricating oil compositions - Google Patents

Lubricating oil compositions Download PDF

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Publication number
US3859218A
US3859218A US306850A US30685072A US3859218A US 3859218 A US3859218 A US 3859218A US 306850 A US306850 A US 306850A US 30685072 A US30685072 A US 30685072A US 3859218 A US3859218 A US 3859218A
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groups
lubricating oil
mixture
composition according
alkyl
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Graham James Jervis
Robert Robson
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy 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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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/111—Complex polyesters having dicarboxylic acid centres
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
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    • 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
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    • 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
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    • 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
    • C10M2223/043—Ammonium or amine salts thereof
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
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    • 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
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    • 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

Definitions

  • a lubricating oil composition having good antiwear Nov. 24, 1971 Great Britain 54577/71 and load carrying properties comprises a lubricating oil and a mixture of (a) a quaternary hydrocarbyl am- [52] US. Cl. 252/325 monium salt of a mono (C C alkyl dihydrogen [51] Int. Cl ClOm 3/38 phosphate and (b) a quaternary hydrocarbyl ammo- [58] Field of Search 252/325 nium salt of a di-(C, C alkyl hydrogen phosphate, e.g.
  • Lubricating oils usually require additives to improve the anti-wear and load carrying properties of the oil, and this is especially the case for aircraft lubricating oils, e.g. aviation turbine lubricants.
  • Certain amine salts of phosphoric and thiophosphoric acids have been proposed previously as anti-wear additives, but although some show good anti-wear properties they are corrosive and/or incompatible with silicone elastomers.
  • We have now found certain amine salts which not only show good anti-wear or extreme pressure properties, but also have good silicone elastomer compatibility. They also show good corrosion properties.
  • a lubricating oil composition comprises a lubricating oil and a mixture of certain amine salts.
  • This mixture comprises (a) a quaternary hydroearbyl ammonium salt of a mono (C C alkyl dihydrogen phosphate of the formula and (b) a quaternary hydrocarbyl ammonium salt of di-(C C alkyl hydrogen phosphate of the formula R O ONRABJRHU where R, R R and R are similar or dissimilar hydrocarbyl groups, R, R R and R containing a total of at least 10 carbon atoms, and R and R similar or dissimilar are C C, alkyl groups.
  • the total number of carbon atoms in R, R R and R must be at least and is preferably more, e.g. at least 14. This means that although one or more of the groups can be relatively short chain, e.g. methyl, or ethyl, one or more of the other groups must be long chain, e.g. decyl, dodecyl, etc.
  • the preferred maximum number of carbon atoms in R, R R and R is 100, whereas when the mixture is added to synthetic ester oils the preferred maximum number of carbon atoms is 40.
  • the groups R, R R and R can be different, in practice it is preferred that at least two of the groups be the same, e.g.
  • the groups R, R, R and R may be straight-chain or branched-chain.
  • R, R R and R may be alkaryl, aralkyl, cycloalkyl, or aryl, but they are preferably alkyl groups.
  • one or more of the groups R, R, R and R may be methyl, ethyl, npropyl, iso-butyl, n-hexyl, n-decyl, Z-ethyl decyl, noctadecyl, m-tolyl, p-ethyl phenyl, benxyl, cyclooctyl, phenyl, or naphthyl; provided the total number of carbon atoms int he four groups is at least 10.
  • Particularly preferred cases are where at least three of the groups s R, R, R and R are the same alkyl groups, e.g. all the same such as n-butyl, or three are octyl as in hexyl trioctyl ammonium salts.
  • each of the groups R, R R and R are termed hydrocarbyl groups, they may however be substituted by polar substituents, e.g. chlorine, or bromine atoms or keto or ethereal groups, provided these substituents are not present in proportions sufficiently large to alter significantly the hydrocarbon character of the group; e.g. the groups contain no more than l()% by weight of polar substituent based on the weight of the hydrocarbyl portion of the group.
  • polar substituents e.g. chlorine, or bromine atoms or keto or ethereal groups
  • the groups R and R are alkyl groups containing l, 2, 3 or 4 carbon atoms, i.e. they are methyl, ethyl, npropyl, iso-propyl, n-butyl, sec-butyl, or iso-butyl groups. It is preferred that both R and R are the same, e.g. both methyl groups or both ethyl groups.
  • Particularly preferred salts are mixtures of tetra-n-butyl ammonium salts of di methyl hydrogen phosphate and methyl di hydrogen phosphate and mixtures of hexyl trioctyl ammonium salts of methyl dihydrogen phosphate and dimethyl hydrogen phosphate.
  • the mixture of acid phosphates from which the quaternary ammonium salts (a) and (b) are derived is best prepared by reacting phosphorus pentoxide with a C C, alcohol or mixture of alcohols, in a proportion of about 3 moles of alcohol per mole of pentoxide.
  • a mixture of alkyl phosphates is obtained according to the following reaction.
  • P20 BROII In practice the phosphorus pentoxide can be stirred vigorously in dry ether and the alcohol is added dropwise at a rate sufficient to cause the ether to reflux gently. The product may thereafter be filtered to remove any unreacted phosphorus pentoxide, and the ether removed by evaporation under vacuum.
  • the mixture of alkyl phosphates thus obtained is reacted with a quaternary ammonium hydroxide solution (e.g. 40% aqueous).
  • a quaternary ammonium hydroxide solution e.g. 40% aqueous.
  • Such solutions may be conveniently prepared by reacting at ambient temperature a tertiary amine with an alkyl halide to form the quaternary ammonium halide.
  • This halide is mixed with a solution of silver oxide in water, and the reaction mixture is agitated. Silver halide is precipitated and a solution containing quaternary ammonium cations and hydroxide anions is obtained.
  • the quaternary ammonium halide can be converted to the corresponding hydroxide by the use of a suitable ion exchange resin, e.g. a polystyrene divinyl benzene copolymer substituted with tertiary amine groups.
  • the amount of the amine salt mixture added to a lubricating oil, especially an aviation turbine oil, is usually a minor proportion, preferably 0.001 to 10.0% by weight, e.g. 0.01 to 5.0% by weight, based on the weight of lubricating oil.
  • the lubricating oil can be any mineral, animal, fish, vegetable or synthetic oil, for example, petroleum oil fractions ranging from spindle oil to SAE 30, 40 or 50 lubricating oil grades, castor oil, animal or fish oils or oxidised mineral oil, e.g. palm oil, lard oil, tallow oil, arachis oil or sperm oil.
  • the preferred lubricating oil is a synthetic ester and suitable diesters include diesters of the general formula ROOCRCOOR and RCOOROOCR where R represents a C to C alkyl group, while R represents a C to C saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group.
  • suitable diesters include diesters of the general formula ROOCRCOOR and RCOOROOCR where R represents a C to C alkyl group, while R represents a C to C saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group.
  • the above types of esters may be prepared from alcohols and dicarboxylic acids or glycols and monocarboxylic acids.
  • ester lubricant are the polyesters which are prepared by reacting polyhydric alcohols eg those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as trimethylolpropane, pentaerythritol and dipentaerythritol with monoand/or di-carboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid, or adipic, sebacic or azelaic acids.
  • polyhydric alcohols eg those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as trimethylolpropane, pentaerythritol and dipentaerythritol with monoand/or di-carboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid, or adipic, sebacic or azelaic acids.
  • the complex esters which may be used as base oils are formed by esterification reactions between a dicarboxylic acid, a glycol and an alcohol and/or a monocarboxylic acid. These esters may be represented by the following formulae:
  • R (OOCR COO-R ),,OOCR wherein R represents alkyl radicals derived from a monohydric alcohol, R represents hydrocarbon radicals derived from a dicarboxylic acid, e.g. alkanedioic acids, R represents divalent hydrocarbon or hydrocarbonoxy radicals such as CH (CH or -CH CH- (OCH CH or CH CH(CH (OCH CH(CH derived from an alkylene glycol or polyalkyleneglycol, while R represents the alkyl group derived from a monocarboxylic acid.
  • n in the complex ester molecule which is an integer will usually range from 1 to 6 depending upon the product viscosity desired which is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid.
  • n the product viscosity desired which is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid.
  • suitable esters of this type are the neopentyl polyol esters of trimethylol ethane, trimethylol propane, trimethylol butane and of pentaerythritol or di-pentaerythritol.
  • the preferred acids used to esterify trimethylol propane are the C to C monocarboxylic acids.
  • Particularly preferred are the C C esters, e.g. C (caprylic) and C (pelargonic) acid esters. Mixtures of these C-,C acids may be used. When such an acid mixture is used, it is preferred that the mixture average between C and C
  • one methylol group be esterified with a neo-heptanoic acid, e.g. 2,2-dimethylpentanoic acid, and the remaining methylol groups esterified with non-hindered acids, e.g. pelargonic acid.
  • This particular ester is substantially as thermally stable as the completely hindered ester but has superior volatility and low temperature characteristics.
  • the preferred acids used to esterify pentaerythritol are the C.,-C monocarboxylic acids with the more preferred esters being those of C to C acids, e.g. nvaleric, isovaleric, 2-ethyl butyric, caproic, n-heptylic, n-octanoic or 2-ethyl hexoic acids or a mixture of C to C acids.
  • Blends of diesters with minor proportions of one or more thickening agents may also be used as lubricants.
  • Formulations suitable for gas turbine lubrication include from 65 to vol.% of one or more diesters of azelaic or sebacic acid and a C -C branched chain alcohol, particularly of 2-ethyl hexanol, or 0x0 alcohols consisting predominantly of C C or C alcohols,
  • R R and R are hydrogen or C -C alkyl groups and wherein not more than two such groups is hydrogen, and n is an integer greater than 1.
  • Particularly useful compounds are poly-oxypropylene glycol and mono-ethers and the corresponding diethers.
  • the thermal stability of such diester/polyoxyalkylene glycol ethers may be improved if a small proportion of a complex ester derived from three or more carboxylic acids or alcohols, at least two of which are difunctional acids or alcohols is incorporated.
  • Such complex esters may be glycolor dicarboxylic acid centered, the molecule being terminated with a mono-hydroxy or monocarboxylic acid compound.
  • a particularly preferred complex ester of this type is derived from polyethylene glycol of molecular weight 200, 2 molecules of sebacic or azelaic acid, and 2 molecules of a C -C branched chain aliphatic monohydric alcohol, particularly 2- ethyl hexanol.
  • additives which may be incorporated in the lubricating oil include corrosion inhibitors, e.g. sebacic acid, a metal deactivator such as quinizarin, a foam inhibitor, e.g. a silicone polymer such as dimethyl silicone, an antioxidant, e.g. phenothiazine or dioctyl diphenylamine; or an antiwear additive, e.g. tricresylphosphate.
  • corrosion inhibitors e.g. sebacic acid
  • a metal deactivator such as quinizarin
  • a foam inhibitor e.g. a silicone polymer such as dimethyl silicone
  • an antioxidant e.g. phenothiazine or dioctyl diphenylamine
  • an antiwear additive e.g. tricresylphosphate.
  • the mixture of amine salts can be added to a liquid fuel oil, e.g. a diesel fuel oil.
  • EXAMPLE 1 Tetrabutyl ammonium salts of mixtures of l methyl dihydrogen phosphate and di-methyl hydrogen phosphate (2) ethyl dihydrogen phosphate and di-ethyl hydrogen phosphate, and (3) n-butyl dihydrogen phosphate and di-n-butyl hydrogen phosphate were prepared according to the following procedure.
  • a aqueous solution of the acid phosphate was stirred and tetra-n-butyl ammonium hydroxide solution (40% aq.) was added to adjust the pH to 7.
  • the solution was evaporated to dryness in the presence of a trace of n-octanol to inhibit foaming. Toluene was added and the solution again evaporated to dryness: this was repeated once to ensure an anhydrous product.
  • Each mixture was separately added to a synthetic ester base oil which also contained 1.0% by weight of tricresyl phosphate, 1.6% by weight of dioctyl diphenyl amine, and 0.4% by weight of phenothiazine.
  • the base oil was a mixture of esters obtained by the esterification of 90% by weight pentaerythritol and 10% by weight dipentaerythritol with a mixture of (C -C fatty acids.
  • the IAE gear machine failure load at 110C/2000 RPM and the Rolls Royce Silicone Elastomer zero swell temperature (C) were determined.
  • the standard Rolls Royce silicone elastomer compatibility test (Method 1,009) involves the immersion of a standard test specimen in 50 ml. of test lubricant at a temperature of 175C for 192 hours. High load carrying oils invariably cannot be made compatible with elastomers under these conditions and so in a modification of this method a series of tests were carried out at different temperatures and a plot of percent elastomer swell versus temperature was made. The temperature (extrapolated) at which the zero swell occurs is given as an index of elastomer compatibility of the oil.
  • a lubricating oil composition comprising a lubricating oil to which has been added from 0.001 to 10 percent by weight, based on the lubricating oil, of a mixture of about equal molar proportions of (a) a quaternary hydrocarbyl ammonium salt of mono (C,C alkyl dihydrogen phosphate of the formula and (b) a quaternary hydrocarbyl ammonium salt of di- (C C alkyl hydrogen phosphate of the formula 11 0 ⁇ ONRIRIBHU where R, R R and R are similar or dissimilar hydrocarbon groups, R, R", R and R containing a total of at least 10 carbon atoms, and R and R similar or dissimilar are C -C alkyl groups, said lubricating oil consisting essentially of polyester of a polyhydric alcohol selected from the class consisting of pentaerythritol, dipentaerythritol and mixtures of pentaerythritol and dipentaeryth
  • a composition according to claim 2 wherein at TABLE Carbon Chain Length Concentration IAE gear machine R-R Silicone Elastomer in acid phosphate wt.% P wt.% (amine salt) Failure Load 2000 Zero Swell mixture rpm/110C. 1b. Temp. (C)
  • Hexyl trioctyl ammonium salts of mixtures of methyl dihydrogen phosphate and dimethyl hydrogen phosphate were prepared by the same procedure of Example 1 except that hexyl trioctyl ammonium hydroxide 4.
  • composition according to claim 1 which contains a mixture of hexyl trioctyl ammonium salts of methyl dihydrogen phosphate and dimethyl hydrogen phosphate.

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3945930A (en) * 1973-09-29 1976-03-23 Toho Chemical Industry Co., Ltd. Water-soluble metal working lubricants
US3951829A (en) * 1975-05-05 1976-04-20 Cities Service Company Two-cycle and rotary combustion engine lubricant
US3979308A (en) * 1974-03-27 1976-09-07 Texaco Inc. Lubricant compositions with improved viscosity index
US4130494A (en) * 1976-05-05 1978-12-19 Exxon Research & Engineering Co. Synthetic lubricant composition
US4514311A (en) * 1983-05-09 1985-04-30 Texaco Inc. Wear-resistant aircraft engine lubricating oil
US4778610A (en) * 1985-12-27 1988-10-18 Mobil Oil Corporation Acid phosphites as multifunctional additives and compositions thereof
US5422023A (en) * 1993-10-12 1995-06-06 Exxon Research And Engineering Company Corrosion inhibitor for aviation turbine oils (PNE-628)
US5547597A (en) * 1992-05-29 1996-08-20 Tonen Corporation Lubricating oil composition for two-cycle engines
US5582760A (en) * 1995-12-22 1996-12-10 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid
US5585029A (en) * 1995-12-22 1996-12-17 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid
US5587355A (en) * 1995-12-22 1996-12-24 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiophene carboxylic acid derivatives
EP0780462A2 (en) 1995-12-22 1997-06-25 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid
US5750478A (en) * 1995-12-22 1998-05-12 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid
US5801130A (en) * 1995-12-22 1998-09-01 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives
US6001778A (en) * 1996-10-01 1999-12-14 J. Morita Manufacturing Corporation Lubricating oil for rolling bearing in high-speed rotating equipment, and bearing lubricated with the same lubricating oil
US20040144355A1 (en) * 2003-01-24 2004-07-29 Carey Vincent Mark Modification of lubricant properties in an operating all loss lubricating system
US20050014659A1 (en) * 2003-07-18 2005-01-20 Exxonmobil Research And Engineering Company Lubricating composition suitable for diesel engines

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EP0320279A3 (en) * 1987-12-09 1989-09-13 Exxon Research And Engineering Company Engine lubricating oil composition
US5348561A (en) * 1990-03-01 1994-09-20 Exxon Chemical Patents Inc. Fuel oil compositions

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US2563506A (en) * 1951-08-07 Quaternary ammonium salts of
US3720612A (en) * 1969-06-25 1973-03-13 Exxon Research Engineering Co Synthetic ester lubricating oil compositions

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US2563506A (en) * 1951-08-07 Quaternary ammonium salts of
US3720612A (en) * 1969-06-25 1973-03-13 Exxon Research Engineering Co Synthetic ester lubricating oil compositions

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3945930A (en) * 1973-09-29 1976-03-23 Toho Chemical Industry Co., Ltd. Water-soluble metal working lubricants
US3979308A (en) * 1974-03-27 1976-09-07 Texaco Inc. Lubricant compositions with improved viscosity index
US3951829A (en) * 1975-05-05 1976-04-20 Cities Service Company Two-cycle and rotary combustion engine lubricant
US4130494A (en) * 1976-05-05 1978-12-19 Exxon Research & Engineering Co. Synthetic lubricant composition
US4514311A (en) * 1983-05-09 1985-04-30 Texaco Inc. Wear-resistant aircraft engine lubricating oil
US4778610A (en) * 1985-12-27 1988-10-18 Mobil Oil Corporation Acid phosphites as multifunctional additives and compositions thereof
US5547597A (en) * 1992-05-29 1996-08-20 Tonen Corporation Lubricating oil composition for two-cycle engines
US5422023A (en) * 1993-10-12 1995-06-06 Exxon Research And Engineering Company Corrosion inhibitor for aviation turbine oils (PNE-628)
EP0780463A1 (en) 1995-12-22 1997-06-25 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiophene carboxylic acid derivatives
US5585029A (en) * 1995-12-22 1996-12-17 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid
US5587355A (en) * 1995-12-22 1996-12-24 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiophene carboxylic acid derivatives
EP0780462A2 (en) 1995-12-22 1997-06-25 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid
US5582760A (en) * 1995-12-22 1996-12-10 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid
EP0780461A1 (en) 1995-12-22 1997-06-25 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phoshate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid
US5679627A (en) * 1995-12-22 1997-10-21 Exxon Research & Engineering Company High-load carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid (law348)
US5750478A (en) * 1995-12-22 1998-05-12 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid
US5801130A (en) * 1995-12-22 1998-09-01 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives
US6001778A (en) * 1996-10-01 1999-12-14 J. Morita Manufacturing Corporation Lubricating oil for rolling bearing in high-speed rotating equipment, and bearing lubricated with the same lubricating oil
US20040144355A1 (en) * 2003-01-24 2004-07-29 Carey Vincent Mark Modification of lubricant properties in an operating all loss lubricating system
US7124728B2 (en) 2003-01-24 2006-10-24 Exxonmobil Research And Engineering Company Modification of lubricant properties in an operating all loss lubricating system
US20050014659A1 (en) * 2003-07-18 2005-01-20 Exxonmobil Research And Engineering Company Lubricating composition suitable for diesel engines
EP1498471A3 (en) * 2003-07-18 2005-04-06 ExxonMobil Research and Engineering Company Lubricating composition suitable for diesel engines
US7598212B2 (en) 2003-07-18 2009-10-06 Exxonmobil Research And Engineering Company Lubricating composition suitable for diesel engines
WO2005045206A3 (en) * 2003-10-28 2005-07-21 Exxonmobil Res & Eng Co Modification of lubricant properties in an operating all loss lubricating system
JP2007515506A (ja) * 2003-10-28 2007-06-14 エクソンモービル　リサーチ　アンド　エンジニアリング　カンパニー 運転中の全損潤滑システムにおける潤滑油特性の変更
AU2004288165B2 (en) * 2003-10-28 2009-10-08 Exxonmobil Research And Engineering Company Modification of lubricant properties in an operating all loss lubricating system

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