US3853777A - Oil compositions - Google Patents

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Publication number
US3853777A
US3853777A US00257631A US25763172A US3853777A US 3853777 A US3853777 A US 3853777A US 00257631 A US00257631 A US 00257631A US 25763172 A US25763172 A US 25763172A US 3853777 A US3853777 A US 3853777A
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esters
oils
group
mineral
oil
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US00257631A
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English (en)
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H Gersmann
Bruggen G Van
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Shell USA Inc
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Shell Oil Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
    • C07F9/4866—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the ester moiety containing a substituent or structure which is considered as characteristic
    • C07F9/4875—Esters with hydroxy aryl compounds
    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • 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
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/135—Steam engines or 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/50—Medical uses
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This class of novel compounds consists of esters which are represented by the general formula wherein X is oxygen or sulfur, R is a hydrocarbyl group, which may be substituted with one or more hetero atoms or hetero groups, and R is a naphthalene ring, which may be substituted, or a benzene ring which carries at one ortho position with respect to the oxygen atom a hydrocarbyl group which is attached to the benzene ring nucleus via a quaternary carbon atom, and which benzene ring may contain other substituents such as halogen atoms, hydroxyl groups, nitro groups and the like.
  • the invention therefore relates to the aforementioned novel esters and to compositions comprising one or more mineral and/or synthetic oils or fuels and one or more of these esters.
  • esters of the invention are esters of hydrocarbylphosphinic acids or hydrocarbylthiophosphinic acids,
  • mula may denote several types of hydrocarbyl groups such as an alkyl group, a cycloalkyl group, an aryl group, an alkaryl group, an arylalkyl group.
  • R stands for an aromatic group such as a phenyl group are very suitable.
  • R may be substituted with one or more heteroatoms or hetero groups, for example, a halogen atom, a nitro group, a substituted or unsubstituted amino group, and the like.
  • An advantageous substituent is a chlorine atom, such as a chlorine atom in a benzene ring, in particular in the para position with respect to the carbon atom of the benzene ring which is attached to the phosphorus atom.
  • R' is a phenyl group or a phenyl group substituted with a chloro group, a C alkyl, or a lower alkyl amino group.
  • substituent is C alkyl, i.e., methyl through hexyl
  • representative R groups include tolyl, ethylphenyl, propylphenyl, isopropylhexyl, hexylphenyl and the like.
  • Representative lower alkyl amino substituents include amino groups substituted with alkyls of l to 4 carbon atoms such as methylamino, dimethylamino, ethylamino, methylethylamino, and the like.
  • esters of the invention are derived from a naphthol or preferably from an alkylphenol ROH, wherein R is a benzene ring which carries at one ortho position with respect to the hydroxyl group a hydrocarbyl group which is attached to the benzene nucleus via a quaternary carbon atom; this hydrocarbyl group very suitably contains not more than 20 carbon atoms, and is preferably an aliphatic group, in particular a tertbutyl group.
  • the benzene nucleus in the alkylphenol ROH may contain one or more other substituents, which may be hydrocarbyl groups or substituted hydrocarbyl groups and/or heteroatoms and/or hetero groups, for example, halogen atoms, hydroxyl groups, nitro groups, and the like.
  • substituents such as 2-methyl-6-tert-butylphenol, bis(3,5-di-tert-butyl-4- hydroxyphenyl)methane, and in particular 2,6- ditertbutyl-4-methylphenol or 2,4-dimethyl-6-tertbutylphenol, in the latter two cases R representing ...H3.c.. --Cl-h or CH3 respectively.
  • esters of hydrocarbylphosphinic acids and phenols which are substituted at both ortho positions relative to the hydroxyl group with a hydrocarbyl group which is attached to the benzene nucleus via a quaternary carbon atom are in many cases difficult owing to the bulky groups around the hydroxyl group, esters of hydrocarbylphosphinic acids and phenols which at only one ortho position are attached to a quaternary carbon atom, are preferred in case they are on the same performance level with respect to the desired properties.
  • esters of the invention may be represented by the formula i u -on,
  • n 2 wherein X is oxygen or sulfur, R is Y is hydrogen, chloro, C alkyl or lower alkyl amino, and R is a phenyl group with at least one tert-butyl substituent ortho to the connecting oxygen atom and containing to 30 carbon atoms.
  • X oxygen or sulfur
  • R is Y is hydrogen, chloro, C alkyl or lower alkyl amino
  • R is a phenyl group with at least one tert-butyl substituent ortho to the connecting oxygen atom and containing to 30 carbon atoms.
  • a more preferred class of compounds is that in which Y is hydrogen or chloro.
  • Y is hydrogen or chloro and R has from 12 to 15 carbon atoms.
  • esters of the invention can be prepared in any desired way.
  • they can be prepared by reacting a hydrocarbyl dichlorophosphine, or substituted hydrocarbyl dichlorophosphine, with an alphaor beta naphthol or with a phenol containing a hydrocarbyl group which is attached via a quaternary carbon atom to the benzene nucleus at an ortho position with respect to the hydroxyl group, in the presence of a tertiary ammonium compound, and subsequent partial hydrolysis of the reaction product obtained.
  • the esters may also be prepared by reacting a hydrocarbyl dichlorophosphine, or a substituted hydrocarbyl dichlorophosphine, with an alkali salt, e.g, sodium salt, of a naphthol or of a phenol containing a hydrocarbyl group which is attached via a quaternary carbon atom to the benzene nucleus at an ortho position with respect to the hydroxyl group, with liberation of an alkali chloride, and subsequent partial hydrolysis of the reaction product obtained.
  • an alkali salt e.g, sodium salt
  • oil compositions particularly lubricating oil compositions, containing the esters of the invention possess anti-wear properties under extreme pressure.
  • the esters according to the invention may be incorporated in oils or liquid hydrocarbon fuels More than one ester can be used.
  • fuels include heavy residual fuels, distillate fuels such as gasoline, aviation turbine fuel, gas oil and the like.
  • the esters can also be incorporated in oils, e.g., a crude mineral oil; prefera bly, they are incorporated in lubricating oils, which may be a mineral or synthetic oil or mixtures thereof. Examples thereof include lubricating oil for combustion engines and lubricating oils for steam turbines and further mineral and synthetic functional liquids such as hydraulic oils, heat transfer oils and automatic transmission oils.
  • the esters of the invention can be incorporated in lubricating greases based on mineral or synthetic oils.
  • the esters are of special importance for improving the oxidation stability of mineral lubricating oils or mixtures thereof.
  • the oils in which the esters of the invention are incorporated are mineral oils, they can be obtained from naphthenic, paraffinic, asphaltic or mixed base crudes and/or mixtures thereof, for example, neutral oils having viscosities of from 100 to 6500 SSU at 100F.
  • the mineral oils may be oils obtained by straight distillation or oils which after distillation have been subjected to one or more refining treatments, such as extractions, dewaxing or a hydrogen treatment. They may contain residual components.
  • Synthetic lubricants suitable for the invention are of various types, such as aliphatic esters, silicones, polyalkylene oxides, polyphenyl ethers, fluorinated hydrocarbons, polyolefins, and phosphate esters.
  • silicones include methyl silicone, methylphenyl silicone, methylchlorophenyl silicone, etc.
  • polyalkylene oxides are polyisopropylene oxide, polyisopropylene oxide diether, and polyisopropylene oxide diester.
  • Fluorinated hydrocarbons include fluorinated oils and perfluorinated hydrocarbons.
  • Preferred synthetic lubricant base stocks are esters of alcohols having 1 to 20, especially 4 to l2, carbon atoms and aliphatic carboxylic acids having from 3 to 20, especially 4 to l2, carbon atoms.
  • esters oils are diisooctyl adipate, diisodecyl adipate and mixtures thereof.
  • Other preferred esters for use as base stocks in the present invention are esters of monocarboxylic acids having 3 to 12 carbons and polyalcohols, such as pentaerythiitol, dipentaerythritol, and trimethylolpropane. Pentaerythrityl and dipentaerythrityl esters of mixtures of C, acids are particularly suitable base oils for the compositions of the invention. Preparation of these esters is described in Eichemeyer, US. Pat. No. 3,038,859, issued June 12, 1962, and Young, US. Pat. No. 3,121,109, issued Feb. ll, 1964.
  • the concentration of the esters in the oils may vary within wide limits, but is suitably from about 0.1 to about 10 percent by weight, and preferably from about 0.2 to about 5 percent by weight.
  • the esters can be added as such to the oils or in the form of a concentrate which has been prepared, for example, by incorporation of the esters in a small quantity of oil.
  • the oils may contain other additives, such as anti-corrosion agents, additives to improve the viscosity and the viscositytemperature behavior detergents and other substances which are usually added to the aforementioned oils.
  • the oils may incorporate other compounds with an antioxidant and/or anti-wear action,
  • EXAMPLE 1 Preparation of the ester of 2,4-dimethyl-6-tertbutylphenol and p-chlorophenylphosphinic acid A suspension of the sodium salt of 2,4-dimethyl-6- tort-butylphenol in toluene was gradually added in about 2 hours to a solution of an equimolar amount of p-chlorophenylphosphinic acid in toluene at about C The mixture obtained was refluxed for 1 hour. After cooling water was added with stirring, the aqueous layer was discarded and the organic layer washed with an aqueous sodium hydrogen carbonate solution.
  • Table II shows that a much higher load is needed for the oils containing the compounds of the invention in order to cause seizure than for undoped oil or oil containing Cereclor 42.
  • a lubricant composition consisting essentially of a major amount of a mineral lubricating oil and from about 0.1 to about 10 percent by weight of a compound having the formula wherein X is oxygen or sulfur, R is F. Y i
  • Y is hydrogen, chloro. C alkyl or lower alkyl amino, and R is a phenyl group with at least one tert-butyl substituent ortho to the connecting oxygen atom and containing 10 to 30 carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
US00257631A 1971-06-02 1972-05-30 Oil compositions Expired - Lifetime US3853777A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1859171A GB1399236A (en) 1971-06-02 1971-06-02 Phosphorus acid esters and oil compositions containing them

Publications (1)

Publication Number Publication Date
US3853777A true US3853777A (en) 1974-12-10

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US (1) US3853777A (enExample)
DE (1) DE2226643A1 (enExample)
FR (1) FR2140112B1 (enExample)
GB (1) GB1399236A (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020151442A1 (en) * 2001-02-07 2002-10-17 The Lubrizol Corporation Lubricating oil composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1117546A (en) * 1978-03-02 1982-02-02 John D. Spivack Hydrolytically stable ortho-alkylated phenyl phosphonites and stabilized compositions

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3088917A (en) * 1961-01-11 1963-05-07 Weston Chemical Corp Mixtures of secondary and tertiary phosphite esters of ether alcohols
US3115466A (en) * 1960-05-05 1963-12-24 Ethyl Corp Synergistic antioxidants
US3321401A (en) * 1964-09-18 1967-05-23 British Petroleum Co Lubricating compositions
US3493638A (en) * 1965-11-01 1970-02-03 Ethyl Corp Bis(3,5-dihydrocarbyl-4-hydroxyphenyl)hydrogen phosphonates
US3553131A (en) * 1967-04-24 1971-01-05 Mobil Oil Corp Lubricant containing an aminephosphonate combined additive
US3718590A (en) * 1970-09-25 1973-02-27 Monsanto Co Polyphenyl thioether lubricating compositions
US3748269A (en) * 1970-12-30 1973-07-24 Monsanto Co Polyphenyl thioether lubricating compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3115466A (en) * 1960-05-05 1963-12-24 Ethyl Corp Synergistic antioxidants
US3088917A (en) * 1961-01-11 1963-05-07 Weston Chemical Corp Mixtures of secondary and tertiary phosphite esters of ether alcohols
US3321401A (en) * 1964-09-18 1967-05-23 British Petroleum Co Lubricating compositions
US3493638A (en) * 1965-11-01 1970-02-03 Ethyl Corp Bis(3,5-dihydrocarbyl-4-hydroxyphenyl)hydrogen phosphonates
US3553131A (en) * 1967-04-24 1971-01-05 Mobil Oil Corp Lubricant containing an aminephosphonate combined additive
US3718590A (en) * 1970-09-25 1973-02-27 Monsanto Co Polyphenyl thioether lubricating compositions
US3748269A (en) * 1970-12-30 1973-07-24 Monsanto Co Polyphenyl thioether lubricating compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020151442A1 (en) * 2001-02-07 2002-10-17 The Lubrizol Corporation Lubricating oil composition

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Publication number Publication date
FR2140112A1 (enExample) 1973-01-12
FR2140112B1 (enExample) 1977-12-23
DE2226643A1 (de) 1973-01-04
GB1399236A (en) 1975-06-25

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