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GB952151A - Lubricating oil compositions - Google Patents

Lubricating oil compositions

Info

Publication number
GB952151A
GB952151A GB31382/62A GB3138262A GB952151A GB 952151 A GB952151 A GB 952151A GB 31382/62 A GB31382/62 A GB 31382/62A GB 3138262 A GB3138262 A GB 3138262A GB 952151 A GB952151 A GB 952151A
Authority
GB
United Kingdom
Prior art keywords
polyalkenyl
mono
amine
formula
radical
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB31382/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB952151A publication Critical patent/GB952151A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
    • 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
    • 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
    • C10M2203/02—Well-defined aliphatic 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
    • 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
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2203/04—Well-defined cycloaliphatic 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • 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
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
    • 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
    • C10M2207/10—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
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—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
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular 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
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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  • Oil, Petroleum & Natural Gas (AREA)
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  • Lubricants (AREA)

Abstract

Compounds of the formula: <FORM:0952151/C2/1> where each R is a C20-500 polyalkenyl radical, each R1 is a C1-8 alkylene radical, x and y are zero or integers, and z is an integer, are prepared by reacting a C20-500 polyolefin with maleic anhydride to form a mono(polyalkenyl) succinic anhydride, and subsequently reacting this product in a mole ratio of from 2:1 to 4:1 with an amine having the formula: H2N-[(R1)x-NH]y-(R1)z-NH2 where R1, x, y and z are as defined above. If the mono(polyalkenyl) succinic anhydride is reacted in a mole ratio of from 1:10 to 2:1 with the above amine, or with such an amine in which one of the terminal amino groups is substituted by one or two C1-5 alkyl radicals, a product may be obtained which is an amino-amide, full or partial amide, or amine salt of a mono(polyalkenyl) succinic acid. The type of product obtained depends on the reactants and reaction conditions.ALSO:Compounds of the formula: <FORM:0952151/C3/1> where each R is a C20- 500 polyalkenyl radical, each R1 is a C1- 8 alkylene radical, x and y are zero or integers, and z is an integer, are prepared by reacting a C20- 500 polyolefin with maleic anhydride to form a mono(polyalkenyl) succinic anhydride, and subsequently reacting this product in a mole ratio of from 2:1 to 4:1 with an amine having the formula: <FORM:0952151/C3/2> where R1, x, y and z are as defined above. The polyolefine may be polyethylene, polypropylene, polybutylene polyisobutylene, or a copolymer of ethylene with propylene, isobutylene or a -methylstyrene. If the mono(polyalkenyl) succinic anhydride is reacted in a mole ratio of from 1:10 to 2:1 with the above amine, or with such an amine in which one of the terminal amino groups is substituted by one or two C1- 5 alkyl radicals, a product may be obtained which is an aminoamide, full or partial amide, or amine salt of a mono(polyalkenyl) succinic acid. The type of product obtained depends on the reactants and reaction conditions.ALSO:A lubricating oil composition comprises a major proportion of a lubricating oil and minor proportions of (a) an oil-soluble di-imide of a mono(polyhydrocarbon) succinic acid or anhydride and (b) an oil-soluble bisphenol. Additive (a) preferably is of the formula <FORM:0952151/C3/1) where each R is a C20-500 polycycloalkyl, poly-alkyl or polyalkenyl radical, each R1 is a C1-8 alkylene radical, x and y are zero or integers and z is an integer. Additive (b) preferably is of the formula <FORM:0952151/C3/2> where R1 is a hydrocarbon radical, preferably alkyl, m is an integer from 1 to 4, X represents -S-, -S-S-, -Se-, -S-CH2-, -CH2-S-CH2-, -CH2-O-CH2-, -CHR-, -CR2-, -(CH2)n-, NH or -O-, R being methyl or ethyl and n being 1, 2 or 3. Optionally there may be present minor proportions of (c) an oil-soluble amino-imide, or full or partial amide, or amine salt of a mono-(polyhydrocarbon succinic acid or anhydride, and/or (d) metal-free organic phosphorus compounds, e.g. phosphites, phosphonates (which may contain chlorine), phosphates, the corresponding thio-derivatives, and P2S5-terpene reaction products. Additives (a) to (d) are extensively exemplified. Further optional additives mentioned include silicone polymers, polymeric acrylic esters, dibenzyl sulphide, the condensation products of maleic anhydride and long-chain olefins, acidless tallow, and peroxidized aromatic extracts. Lubricating oils which may be used are various mineral oils, hydrocarbon lubricants derived from coal products, alkylene polymers, alkylene oxide-type polymers, dicarboxylic acid esters, liquid esters of phosphoric acids, alkyl benzenes, polyphenyls, alkyl biphenyl ethers, silicic acid esters, and polysiloxanes, examples of such oils being given.
GB31382/62A 1962-04-19 1962-08-15 Lubricating oil compositions Expired GB952151A (en)

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US3385790A (en) * 1965-04-27 1968-05-28 Monsanto Co Antioxidant compositions
US3493511A (en) * 1966-12-28 1970-02-03 Mobil Oil Corp Organic compositions containing antioxidants
US3676346A (en) * 1970-02-19 1972-07-11 Exxon Research Engineering Co Lubricating oil compositions containing improved sludge inhibiting additives
EP0879831A1 (en) * 1997-05-19 1998-11-25 Bridgestone Corporation An extended polymer composition derived from grafted elastomers and polypropylene
EP0955317A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Grafted maleimide-styrene-g-polypropylene copolymers used in rubber compounds for increasing hysteresis
EP0955318A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Gels derived from extending grafted alpha-olefin-maleimide centipede polymers and polypropylene
EP0955320A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Gels derived from extending grafted comb polymers and polypropylene via a solution synthesis
EP0955319A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Soft compounds derived from polypropylene grafted disubstituted ethylene-maleimide copolymers
EP0955316A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Gels derived from extending grafted centipede polymers and polypropylene
US6133354A (en) 1998-11-17 2000-10-17 Bridgestone Corporation Copolymers as additives in thermoplastic elastomer gels
US6184292B1 (en) 1998-10-05 2001-02-06 Bridgestone Corporation Soft gel polymers for high temperature use
US6191217B1 (en) 1998-11-17 2001-02-20 Bridgestone Corporation Gels derived from polypropylene grafted alkyl vinylether-maleimide copolymers
US6207763B1 (en) 1998-06-12 2001-03-27 Bridgestone Corporation Application of disubstituted ethylene-maleimide copolymers in rubber compounds
US6248827B1 (en) 1997-12-22 2001-06-19 Bridgestone Corporation Centipede polymers and preparation and application in rubber compositions
US6384134B1 (en) 2000-06-05 2002-05-07 Bridgestone Corporation Poly(alkenyl-co-maleimide) and maleated polyalkylene grafted with grafting agent, and epoxy polymer
US8513361B2 (en) 2007-12-28 2013-08-20 Bridgestone Corporation Interpolymers containing isobutylene and diene mer units
CN111100557A (en) * 2015-06-11 2020-05-05 株式会社自动网络技术研究所 Composition for coating metal surface and covered electric wire with terminal

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US4256595A (en) * 1978-09-28 1981-03-17 Texaco Inc. Diesel lubricant composition containing 5-amino-triazole-succinic anhydride reaction product

Cited By (22)

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Publication number Priority date Publication date Assignee Title
US3385790A (en) * 1965-04-27 1968-05-28 Monsanto Co Antioxidant compositions
US3493511A (en) * 1966-12-28 1970-02-03 Mobil Oil Corp Organic compositions containing antioxidants
US3676346A (en) * 1970-02-19 1972-07-11 Exxon Research Engineering Co Lubricating oil compositions containing improved sludge inhibiting additives
EP0879831A1 (en) * 1997-05-19 1998-11-25 Bridgestone Corporation An extended polymer composition derived from grafted elastomers and polypropylene
US6248827B1 (en) 1997-12-22 2001-06-19 Bridgestone Corporation Centipede polymers and preparation and application in rubber compositions
EP0955318A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Gels derived from extending grafted alpha-olefin-maleimide centipede polymers and polypropylene
EP0955320A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Gels derived from extending grafted comb polymers and polypropylene via a solution synthesis
EP0955319A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Soft compounds derived from polypropylene grafted disubstituted ethylene-maleimide copolymers
EP0955316A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Gels derived from extending grafted centipede polymers and polypropylene
US6048930A (en) * 1998-05-06 2000-04-11 Bridgestone Corporation Grafted maleimide-styrene-g-polypropylene copolymers used in rubber compounds for increasing hysteresis
US6455626B2 (en) 1998-05-06 2002-09-24 Bridgestone Corporation Gels derived from extending grafted centipede polymers and polypropylene
US6248825B1 (en) 1998-05-06 2001-06-19 Bridgestone Corporation Gels derived from extending grafted centipede polymers and polypropylene
EP0955317A1 (en) * 1998-05-06 1999-11-10 Bridgestone Corporation Grafted maleimide-styrene-g-polypropylene copolymers used in rubber compounds for increasing hysteresis
US6204354B1 (en) 1998-05-06 2001-03-20 Bridgestone Corporation Soft compounds derived from polypropylene grafted disubstituted ethylene- maleimide copolymers
US6207763B1 (en) 1998-06-12 2001-03-27 Bridgestone Corporation Application of disubstituted ethylene-maleimide copolymers in rubber compounds
US6184292B1 (en) 1998-10-05 2001-02-06 Bridgestone Corporation Soft gel polymers for high temperature use
US6191217B1 (en) 1998-11-17 2001-02-20 Bridgestone Corporation Gels derived from polypropylene grafted alkyl vinylether-maleimide copolymers
US6133354A (en) 1998-11-17 2000-10-17 Bridgestone Corporation Copolymers as additives in thermoplastic elastomer gels
US6384134B1 (en) 2000-06-05 2002-05-07 Bridgestone Corporation Poly(alkenyl-co-maleimide) and maleated polyalkylene grafted with grafting agent, and epoxy polymer
US8513361B2 (en) 2007-12-28 2013-08-20 Bridgestone Corporation Interpolymers containing isobutylene and diene mer units
US9428619B2 (en) 2007-12-28 2016-08-30 Bridgestone Corporation Interpolymers containing isobutylene and diene mer units
CN111100557A (en) * 2015-06-11 2020-05-05 株式会社自动网络技术研究所 Composition for coating metal surface and covered electric wire with terminal

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