US2892783A - Lubricant composition - Google Patents

Lubricant composition Download PDF

Info

Publication number
US2892783A
US2892783A US729560A US72956058A US2892783A US 2892783 A US2892783 A US 2892783A US 729560 A US729560 A US 729560A US 72956058 A US72956058 A US 72956058A US 2892783 A US2892783 A US 2892783A
Authority
US
United States
Prior art keywords
oil
carbon atoms
groups
weight
polymer
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 - Lifetime
Application number
US729560A
Other languages
English (en)
Inventor
Frank A Stuart
William T Stewart
Frank W Kavanagh
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.)
California Research LLC
Original Assignee
California Research LLC
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
Priority to NL238305D priority Critical patent/NL238305A/xx
Application filed by California Research LLC filed Critical California Research LLC
Priority to US729560A priority patent/US2892783A/en
Priority to BE577456D priority patent/BE577456A/xx
Priority to GB12253/59A priority patent/GB917923A/en
Priority to FR791920A priority patent/FR1225980A/fr
Priority to NL238305A priority patent/NL122867C/xx
Priority to DEC18835A priority patent/DE1248204B/de
Priority to US821686A priority patent/US3073807A/en
Application granted granted Critical
Publication of US2892783A publication Critical patent/US2892783A/en
Priority to US197839A priority patent/US3189586A/en
Priority to US427159A priority patent/US3337516A/en
Priority to US661837A priority patent/US3428615A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/005—Macromolecular compounds, e.g. macromolecular compounds composed of alternatively specified monomers not covered by the same main group
    • 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
    • C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • 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
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • 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
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/02—Polyethene
    • 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated 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
    • C10M147/00—Lubricating compositions characterised by the additive being a macromolecular compound containing halogen
    • C10M147/02—Monomer containing carbon, hydrogen and halogen only
    • 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
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated 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
    • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
    • C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated 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
    • C10M153/00—Lubricating compositions characterised by the additive being a macromolecular compound containing phosphorus
    • C10M153/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated 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
    • 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
    • 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
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
    • 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
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
    • 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
    • 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
    • C10M2203/04—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
    • C10M2203/10—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
    • 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
    • C10M2205/022—Ethene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • 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
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
    • 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
    • C10M2205/17—Fisher Tropsch reaction products
    • 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
    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
    • 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
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • 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
    • C10M2207/027—Neutral salts thereof
    • 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • 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
    • 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • 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
    • 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
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • 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
    • 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
    • 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
    • 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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • 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
    • 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
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/026—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/044—Polyamides
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/045—Polyureas; Polyurethanes
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • 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
    • C10M2223/02—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
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol-fuelled engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S526/933—Detergent property or lubricant additive

Definitions

  • This invention relates to a novel lubricant composition, and it is particularly directed to the provision of a lubricant composition which is adapted to be employed in internal combustion engines.
  • a lubricant which will permit the engine to be operated at a high level of efiiciency over long periods of time.
  • the pri mary fuiiction of the lubricant is, of course, to reduce friction and thereby not only decrease the wear on pistons, piston walls, bearings and other moving parts, but also increase theetliciency of the engine. Additionally, it is also a function of the lubricant to prevent the deposition of solid products on the piston Walls and other surfaces of the engine coming in contact with the lubricant.
  • any metal-containing additives present in the oil may form an ash which is partially deposited out on the various surfaces of the combustion chamber and on those of the spark plugs and valves. Accordingly, it is a particular object of this invention to provide a lubricant composition which is compounded with metalor mineral-free detergents and wear-reducing additives.
  • a material normally referred to as a detergent a material normally referred to as a detergent.
  • all the detergent additives which have been successfully employed prior to the present invention on a commercial scale are organic, metal-containing compounds such as calcium petroleum sulfonate, calcium cetyl phosphate, calcium octyl salicylate, calcium phenyl stearate, the barium salt of wax-substituted benzene sulfonate, or the potassium salt of the reaction product of phosphorus pentasulfide and polybutene.
  • Various of these detergents act by reacting chemically with deposit precursors to form harmless compounds.
  • Detergents capable of acting in the latter fashion are preferably employed wherever possible, particularly in automotive engines to be operated under city driving conditions.
  • metal-containing additives few are available which are capable of solubilizing any appreciable amount of all the many types of polymer precursors which are carried into the oil from the fuel.
  • piston ring and cylinder wall wear is also one which is closely related to the composition of the crankcase lubricant.
  • abrasive wear which is caused by dust and dirt and can be remedied by suitable filtering and aircleaning means, a large part of the wear experienced by piston rings and cylinder wall is attributable to chemical attack by moisture and acidic products originating as byproducts of fuel combustion. In engines operated at optimum temperature levels, these combustion products are largely discharged through the exhaust and breather pipe.
  • the invention is based on the discovery that certain polyglycol substituted copolymers, which contain no metal component and therefore are substantially free of any ashgforming tendency, have the ability to impart excellent detergent and antiwear qualities to lubricating oils employed in internal combustion engines.
  • these copolymers have the ability to solubilize in the oil large amounts of all the various partially oxidized combustion products of the fuels employed in internal combustion engines, while also having the ability of maintaining in a state of suspension any solid .polymeric products present in the oil.
  • the copolymeric additives effectively reduce the wear experienced by piston rings and cylinder wall surfaces even under themost unfavorable operating conditions such as.
  • additives are experienced during the starting and warming up of the'engine.
  • These additives have the advantage that they apparently do not' combine chemically with the various polymer precursors which are solubilized or dispersed in the oil, nor apparently do they act by a neutralization 'reaction'in counteracting the effect of the various acidic fuel combustion by-products. Accordingly, they are capable of giving excellent protection against engine deposits and wear over extended operating periods.
  • the copolymeric additives of the polyglycol ester type are noncorrosive to the various bearing metals employed in engines.
  • The-polyglycol additive of the present invention is a predominantly aliphatic hydrocarbon macro-molecule having polyglycol groups which comprises up to about 99.9% by weight of hydrocarbon oil-solubilizing groups selected from the class consisting of aliphatic and cycloaliphatic hydrocarbon groups of at least 4 carbon atoms each and at least about 0.1% by weight of polyglycol groups having at least 5 alkylene oxide units in each polyglycol group and from 2 to 7 carbon atoms in each alkylene oxide unit, said macromolecule having an average molecular weight of at least about 50,000 and a solubility in oil of at least 0.5% by weight.
  • the essential composition of the polyglycol additive as described above is the predominantly aliphatic hydrocarbon macromolecule having polyglycol groups.
  • the aliphatic hydrocarbon portion provides the oil solubility to the additive and the polyglycol portion provides the polarity to the additive.
  • the combination of these portions in the macromolecule results in an additive having the detergent and antiwear properties as noted above.
  • A is an organic macromolecule group, preferably an aliphatic hydrocarbon group, and R is an aliphati-c or cycloaliphatic hydrocarbon group of at least 4 carbon atoms or mixtures thereof
  • L and L are suitable divalent linking groups
  • PG is a polyglycol group having at least 5 alkylene oxide units and from 2 to 7 carbon atoms in each alkylene oxide unit
  • O is a polar group other than the polyglycol group.
  • the letters x, y and aim the formula are integers showing the number of times the bracketed portions occur.
  • Illustrative polyvalent linking groups of the type mentio'ned in the preceding paragraph include alkylene groups such as methylene -CH oxy O--, carbonyl H imino carbonyloxy Ni J-O, sulfide -S' phosphonyloxy -P and imino --NH- groups and combinations thereof with alkylene groups of from 1 to 7 carbon atoms each.
  • Illustrative polar groups other than the polyglycol group include the free carboxyl group the amidocarbonyl group ((INH2) hydroxy and amino-substituted alkylamide groups (-CNH-ROH and where R is an alkylene group, preferably of not more than (carbon atoms), hydroxy and amino-substituted alkyl ester groups, heterocyclic nitrogenous groups, such as pyridyl, pyrollidyl and carbazolyl groups, epoxy groups, such as the glycidyl group, and cyano groups.
  • the amidocarbonyl group (INH2) hydroxy and amino-substituted alkylamide groups (-CNH-ROH and where R is an alkylene group, preferably of not more than (carbon atoms), hydroxy and amino-substituted alkyl ester groups, heterocyclic nitrogenous groups, such as pyridyl, pyrollidyl and carbazolyl groups, epoxy groups, such as the
  • the predominantly aliphatic hydrocarbon macromolecule of the invention due to its high molecular Weight of 'at-least.50,000 is most suitably a polymeric type com pound.
  • satisfactory polyglycol additives are obtained by attaching polyglycol groups to ethylene, propylene or isobutylene polymers by means of suitable groups.
  • Particularly suitable hydrocarbon macromolecules areobtained by copolymerizing (A) oil solubilizing olefinsof 2 to 30 carbon atoms or monomeric compounds having a polymerizable ethylenic group and containing a hydrocarbyl group of from 4 to 30 aliphatic carbon atoms, (B) polyglycol monomeric compounds having a polymerizable ethylenic linkage and a polyglycol group containing at least 5 alkylene oxide units in which each alkylene oxide unit has from 2 to 7 carbon atoms and, optionally, (C) monomeric polar compounds having a polymerizable ethylenic linkage and a polar group of the type mentioned above.
  • A oil solubilizing olefinsof 2 to 30 carbon atoms or monomeric compounds having a polymerizable ethylenic group and containing a hydrocarbyl group of from 4 to 30 aliphatic carbon atoms
  • B polyglycol monomeric
  • the oil-solubilizing aliphatic radical can be introduced into the copolymer, as will hereinafter be more fully described.
  • This aliphatic radical imparts oil solubility to the polymer and is preferably a branched or straight-chain alkyl radical or a cycloalkyl radical such as butyl, isobutyl, n-pentyl, n-hexyl, 2-ethylhexyl, decyl, dodecyl, tetradecyl, cyclohexyl, 4-ethylcyclohexyl, or the like, or an alkenyl radical such as oleyl, ricinoleyl, or the like, wherein the ethylenic double bond has substantially no copolymerizing tendency.
  • a branched or straight-chain alkyl radical or a cycloalkyl radical such as butyl, isobutyl, n-pentyl, n-hexyl, 2-ethylhexyl, decyl, dodecyl, tetradecyl, cycl
  • Oil solubilizing monomers of this general character are well known in the art and are frequently employed as the oil-solubilizing portion of copolymers which are added to lubricating oils to improve the viscosity index and pour point characteristics thereof. They include such materials as olefins and ethylenically unsaturated others, esters, ketones, aldehydes, and the like.
  • oil solubilizing monomeric compounds of component (A) may also be illustrated by the following general formula:
  • R and R are members of the group consisting of hydrogen and hydrocarbon radicals of from 4 to 30 carbon atoms, at least one of which contains an aliphatic hydrocarbon group of from 4 to 30 carbon atoms as described above
  • G and G are members of the class consisting of oxy l carbonyl i and carbonyloxy i-0 or O(]) groups and combinations thereof with not more than two alkylene groups of from 1 to 7 carbon atoms each, and n and n are 0 or 1.
  • R and R are hydrocarbon radicals, they may be alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl in structure, as illustrated by radicals such as Z-ethylhexyl, cyclohexyl, hexenyl, cyclohexenyl, phenyl, naphthyl, tertiary butylphenyl benzyl, etc., with the preferred radicals being as previously mentioned.
  • Representative oil-solubilizing olefins and monomeric compounds of the aforementioned types which can be employed to form the copolymeric additives of the present invention include the following:
  • Representative acids of this type are the acrylic, methacrylic, crotonic, tiglic, angelic, a-ethylacrylic, a-methylcrotonic, a-ethylcrotonic, fi-ethylcrotonic, fi-propylcrotonic, and hydrosorbic acids and the like. Even more desirable are the alkyl esters of acrylic and methacrylic acids containing from 10 to 20 carbon atoms in the alkyl groups, since they are found to provide highly superior polymers for the lubricant compositions of the invention and are obtainable in commercial quantities.
  • the base oil unless otherwise indicated, is a solvent-refined, wax-free, SAE-30 grade mineral lubricating oil having a viscosity index of which is derived from California waxy crude.
  • Various amounts of the copolymers are incorporated into the oil as indicated in terms of percent by weight.
  • the piston varnish ratings of the lubricant compositions were obtained by the standard FL-2 test procedure as set out in the June 21, 1948 report of the Coordinating Research Council. In this test the lubricants in a 6-cylinder Chevrolet engine, using a low-grade gasoline especially prone to cause engine deposits. At the end of each test the engine was dismantled and the detergency or deposition properties of the lubricant compositions were determined by examining the engine deposits on the piston and visually rating them as to the amount of 7 piston varnish present.
  • the piston varnish ratings of the compositions are given in numerical terms on a scale of' l0with l0 representing the complete absence of'depi5s'it's;
  • the deposition characteristics of the lubricant compositions containing the copolymeric additives were also determined in the lacquer deposition test. In this test typical engine fue'l combustion products were passed into the lubricant compositions and the ability of the lubricant compositions to solubilizeand retain the lacquer-forming materials was observed by weighing the amount of lacquer deposits fo'rrned on a fresh iron catalytic surface for a, standard perio'dtof time.
  • the lacquer deposit of the lubricant composition isftaken as the number of milligrams'deposit' onfth'e' metal surface, and may be correlated directly to the piston varnish rating obtained in the standard FLA-'2 test procedure outlined in the above para- Both the FL-2 test procedure and the lacquer deposition 'tesf'are more fully described in the disclosure which follows with'regard to the particular lubricant composition of the present invention.
  • the particular polymeric additives of the inventign' have the above-described essentialj characteristics, Poly-l 2 alkylene glycols and,,their' aIkyLethers haying molecular; weights between 220 and 30,000. are preferred .
  • Such glycols may be obtained by polymerizing l,2-alky l e n oxides or mixturesthereof in the presence jot acata lysg and a suitable initiator for the reactionsuehaslwater, monohydric alcohol in the case of the alkyl Qthers meQ captans and the like.
  • the preparation 10fp'olygly'jc'qol compounds of thi s type hasbeen fully .dtscribedlheretofore in US. Patents 2,448,664and2,451,139,,for ,example, and, therefore, requires 'nodetailed discussion here.
  • polyalkylene glycol groups are found'to provide” the most effective detergent and .wear inhibiting compositionsl
  • lacquer- Y deposit 3.0%(1)tridecylmethacrylate fl) octadeeyl methacrylato, (3) monododecyl ether of 1 hexadecacthylen'e glycol I methacry fl 10/6/1 8. 4 2.8% 1)vinyl stea'rate, (2) maleic anhydride, (3) monododecyl ether of pcntaethylene glycol P methacrylate, (4) methacry e /1/2/1 325 6.
  • the polyglycol groups of the predominantly aliphatic hydrocarbon macromolecule additives-according to the invention are essentially characterized by the presence of at least 5 alkylene oxide units each with alkylene groups of from 2 to 7 carbon atoms each as previously mentioned.
  • the predomin n aliphatic hydrocarbon use cules having polyglycol groups in accordance with the invention as already mentioned are most suitably polymeric additives.
  • the polyglycol groups are operative Without regard to any specific mode of attachment to the hydrocarbon portion of the additive, particularly suitable additives are obtained by copolymerizetion of an oil-solubilizing monomer (A) with a polyglycol (B) monomer having a polymerizable ethylenic linkage and a polyalkylene glycol group of the abovedescribed type.
  • suitable polyglycol monomers are characterized by a hydrocarbon portion having a polymerizable ethylenic linkage which is connected to the polyglycol portion by a linking group of the aforementioned description.
  • Illustrative polyglycol monomeric compounds are the monoesters of 04,]3-UIISHtUI'3t6d monocarboxylic acids of 3 to 15 carbon atoms and aJB-UHSQUJI'MCG, a,,8-dicarboxylic acids of 4 to 12 carbon atoms.
  • the preferred monocanboxylic acids are those containing from 3 to 8 carbon atoms and more particularly acrylic and methacrylic acids.
  • the preferred dicarboxylic acids contain a total of from about 4 to 8 carbon atoms with maleic acid being particularly preferred.
  • polyglycol monomers are also included as suitable polyglycol monomers.
  • Such monomers are obtained when the amide of an unsaturated acid is used as an initiator in the polymerization of the 1,2-alkylene oxides or mixtures thereof as mentioned above.
  • the methacrylamide initiated polyalkylene-glycol is an example of these monomers.
  • the vinyl and allyl monoethers of polyglycols are also satisfactory polyglycol monomers.
  • Such ethers are obtained by the reaction of acetylene with preformed polyglycol or by the use of unsaturated alcohols such as allyl alcohol as initiators in the polymerization of 1,2- alkyleneoxides or mixtures thereof.
  • unsaturated alcohols such as allyl alcohol as initiators in the polymerization of 1,2- alkyleneoxides or mixtures thereof.
  • these monomers are allyl alcohol initiated polyethylene glycol and methallyl alcohol initiated polyethylene gycol.
  • R and R represent hydrogen atoms
  • R represents hydrogen or a methyl group
  • the R s are ethylene or propylene groups
  • R is hydrogen or an alkyl group of from 1 to 18 carbon atoms.
  • the optional monomeric polar compounds previously designated as the (C) monomers are monomers having a polymerizable ethylenic linkage and a polar group.
  • Many such monomeric polar compounds for use in the production of polymeric detergents for lubricating oils have been recognized and may be incorporated in the additives of the present invention without adversely afiecting the superior detergent and antiwear properties.
  • polyglycol copolymers including amino and hydroxy-substituted alkyl esters of unsaturated carboxylic acid as illustrated by the copolymer of (A) dodecyl methacrylate (B) dodecyl ether of polyethylene glycol monomethacrylate in which the polyethylene glycol has a molecular weight of 1600 and (C) ethylene-glycol monomethacrylate.
  • the optional polar groups other than the polyglycol group of the additives of the invention are incorporated into the macromolecule by various suitable methods known to the art, the preferred additives are copolymers containing copolymerized polar group monomers other than the polyglycol monomers referred to above.
  • suitable polar group monomers besides the polyglycol monomers include the heterocyclic nitrogenous monomers such as vinyl pyridine, vinyl pyrollidone and vinyl carbozole.
  • Epoxy ether and ester monomers such as glycidyl vinyl ether and glycidyl methacrylate are also illustrative of suitable polar monomers in combination with the polyglycol group monomers.
  • Various alkyl derivatives of the polar monomers are likewise satisfactory as in the case where lower alkyl groups are substituted on the ring of the heterocyclic nitrogenous monomers.
  • Combinations of the aforementioned polar groups are also included, as for example where both a vinyl pyrollidone and a dialkyl aminoalkyl ester of an unsaturated carboxylic acid are used together with the polyglycol monomer and the oil-solubilizing monomer.
  • the polyglycol additives of this invention it is important to obtain a final product which is oil soluble, i.e., which is soluble in the petroleum or other lubricating oil employed, to the extent of at least 0.5%, and preferably 2% or more by weight. Since the various oil-solubilizing aliphatic hydrocarbon groups, for example, the oil-solubilizing monomer components of the polymeric type macromolecular polyglycol additives, differ somewhat in their oil-solubilizing characteristics, preliminary tests are made with the additive to determine whether the relative proportion of aliphatic hydrocarbon, or of oil-solubilizing monomer compound in the copolymer, is high enough to impart the desired degree of oil. solubility;- If the solubility in oil is unduly low the proportion of aliphatic hydrocarbon groups is easily in creased to raise the oil solubility to the desired level,
  • a higher alco hol e.g., a C or higher aliphatic alcohol such as 1 1- octanol, 2 -ethylhexanol, decanol, dodecanol (lauryl al
  • sat sf ry oi -sol b i antiwear and detergency properties are obtained with polyma r t et or. oi -s lub z n q m s m @92 stitutes from about 40 to 99.9. weight percent of the overl rol m c mi qsit c i h th (B), MQMH.
  • the balance or polar portion of the polymer takenonthe basis of l00 w eigl:it"per n polar p t is m de u r mfii t JOO. w i ht pe cent of the (B) component and 65 I00 weight percent of the (0) component. V, 4 p,
  • the polar balance of a givencopolyn'fer according to the abovefo'rmula is equal to th'esurn of theln'u'mberof each type 'of' polar". group multiplied by. its polarityiconstant, said sum being-thendividd byzth'e number of solubilizingaliphatic carbon atoms.
  • .Thomacromolecules employed in the compositions of this invention canbe prepared by any one of several me hpq ma tk own in t rt A te e, the oil-solubilizing groups, the polyglycol groups and the option'al polar groups of the macromolecules areattached invarious ways. In the case of theessential polyglycol groups there are three general methods of attachment.
  • (1 )Il'1e polyglycolgroup may be incorporated by reactionwith a preformed polymer containing reactivecen; ters such asjree carboxyl groups.
  • Thepolyglycol group may also be introduced as a polymerizablemonomer prepared by (a) reacting a polyglycol compound with a reactive monomer such as methacrylylchloride or methacrylic acid, or .(b) initiating alkylene oxide poly merization with a suitable compound containing a poly merizable double bond, suchas allylalcohol.
  • the polyglycol group may also be incorporated'in a similar fashion by initiating thealkylene oxide polymerization with a preformed polymer containing reactive centers as described in 1). In the caseof the oil-solubilizing groups and the optional polar groups themethods of attachment would be the same except for the alkylene oxide polymerization.
  • o nemay first copolymerize a givenoil-solubilizing compoundsuch as an alkyl methacrylate with a suitablejacid component such as methacrylic acid or maleic.
  • the resulting polymer is then reacted with a polyalkylene glycol whereby a portion or all of the free -COO H groups in the polymer intermediate becomemonoester-linked to the polyalkylene glycol.
  • the polymeric additive of this invention or a suitable polymeric intermediate
  • said polymers can be prepared by conventional bulk, solution or emulsion methods in the presence of an addition polymerization initiator.
  • the copolymerization is effected in an inert organic solvent such as benzene, toluene, xylene or petroleum naphtha in the presence of a free radical-liberating type of initiator such as a peroxy compound, for examplejbenzoyl peroxide, acetyl peroxide, tert. butyl hydroperoxide, di-tert.' butyl peroxide, dibenzoyl peroxide, or di-tert.
  • a peroxy compound for examplejbenzoyl peroxide, acetyl peroxide, tert. butyl hydroperoxide, di-tert.' butyl peroxide, dibenzoyl peroxide, or di-tert.
  • amyl peroxide or an azo initiator such as 1 ,l'-azodicyclohexane-carbonitrile or a,a'-azodiisobutylronitrile.
  • the catalyst, or polymerization initiator can be employed in an amount of from about 0.1 to 10%, with a preferred range being from 0.10 to 2%. If desired, the catalyst can be added in increments as the reaction proceeds. Likewise, additional portions of the solventcan also be added from time to time in orderito maintain the solution in a homogeneous condition.
  • the temperature of copolymerization varies from about to 30091 withthe optimum tcmperature for any given preparation depending on thenature of thesolvent, the concentration of monomers present in the solvent, the catalyst, and the duration of the reaction. Much the same conditions are employed when the copolyfnerizationis efiected in bulk rather than in the presence of an'inert solvent.
  • Other types of polymeric macromolecules within the scope of the invention as described above include the condensation polymers such as linear polyamides and polyesters having linked thereto suitable oil-solubilizing groups, polyglycol groups and polar groups of the aforementioned kinds.
  • Such polyamides and polyesters are obtained by the well known condensation reactions of polybasic acids, polyamines, polyhydric alcohols, amino acids, amino alcohols, and the like.
  • condensation of tartaric acid with ethylene diamine gives a linear polyamide having hydroxyl groups along the linear chain which may be used to introduce appropriate oil-solubilizing groups and polar groups.
  • the additives of the invention have apparent molecular weights as determined by standard light scattering methods of at least 50,000. For practical purposes, molecular Weights of from 100,000 to 1,000,000 are most suitable from the standpoint of viscosity and other physical characteristics of the polymeric additives.
  • EXAMPLE I In this operation a homopolymer of dodecyl methacrylate (Acryloid 710, a product of Rohm & Haas Company) was employed as the starting material from which was prepared a copolymer intermediate of dodecyl methacrylate and methacrylic acid. Tlze preparation was as follows: A solu ion of 14 gramsof potassium hydroxide in 300 cc. of 2-ethylhexanol was prepared, and to this solution was added 800 cc. of a 40% solution in mineral oil of the methacrylate homopolymer, this amount of KOH constituting a slight excess over that theoretically required to effect the desired saponification of approximately 12% of the ester groups present in the polymer.
  • a solu ion of 14 gramsof potassium hydroxide in 300 cc. of 2-ethylhexanol was prepared, and to this solution was added 800 cc. of a 40% solution in mineral oil of the methacrylate homopolymer
  • the resulting solution was heated to 320 F. and maintained at this temperature, with stirring, for hours.
  • To this solution was then added 50 cc. of benzene along with a 50% excess of 6NHC1 over the amount theoretically required to liberate the free carboxyl groups from the corresponding salt.
  • the acidified solution was then refluxed for two hours, after which it was cooled, diluted with ethyl ether, and water washed (along with a small amount of ethyl alcohol to break the emulsion) until neutral to litmus.
  • the ether and dodecyl alcohol present in the solution were then distilled off, leaving as the oil-soluble residue a copolymer of dodecyl methacrylate and methacrylic acid wherein said components were present in a monomer ratio of 7.5 :1, respectively.
  • 140 grams of the resulting polymer intermediate were then dissolved in 250 grams of xylene and 60 grams of benzene, and to the resulting solution was added 60 grams of a mixture of polyethylene glycol compounds consisting of major portions of nonaethylene glycol and having an average molecular weight of about 400, together with one-half gram of the esterification catalyst p-toluene sulfonic acid.
  • This mixture was reiluxed at 270 F for 10 hours, after which a sufficient quantity of solvent was distilled off to raise the reflux temperature to 335 F., with the refluxing being continued for three hours at this temperature.
  • the reaction mixture was then cooled and dissolved in an equal volume of benzene, from which solution the polymer was then precipitated out by the addition of five times the volume of a 4:1 acetone-methanol mixture.
  • This polymer incorporated dodecyl methacrylate, methacrylic acid and polyethylene glycol monomethacrylate monomer units in the approximate proportions of 7.5:085:0.15, respectively.
  • the viscosity blending characteristics of this product are substantially the same as those of Acryloid 710, indicating little change in molecular weight.
  • this polymer had an average piston varnish rating of 7.5. Further, the wear sustained by the piston 14 rings during this test was found to be but 2.6 mgs./hr'. as compared with a value of 5.5 mgs./hr. for the base oil alone.
  • EXAMPLE III 75.5 g. (0.3 mole) of octadecene, 63 g. (0.3 mole) of di-Z-ethylhexyl fumarate, 8.2 g. (0.095 mole) of crotonic acid, and 16.3 g. (0.23 mole) of tridecyl-capped polyethylene glycol methacrylate (molecular weight 708) were charged to a polymerization reactor as described in the preceding example. The mixture was stirred and heated to 220225 F. with stirring. Bulk benzoyl peroxide was added intermittently in 0.8 g. installments during the course of 7 hours. The mixture was then kept at 194 F. for a period of 88 hours.
  • the polyisobutylene corresponding roughly to heptaisobutylene.
  • 90 g. of a boron trifluoride phenol complex was added to catalyze-the alkylation.
  • An additional 90 g. of catalyst was added after the re- I
  • The-heatmg was continued for another 3 hours and 2:5 liters of a 10% solution of potassium carbonate was then added to the mixture. This mixture was stirred for half an hour,
  • the yield of lubricating oil polymer concentrate was 245 g.
  • the polymer was a copolymer of heptaisobutylene-phenoxyethyl methacrylate-metha crylic acid-dodecyl ether of decaethylene glycol methacrylate with a ratio of 20:2:5.
  • tolubric'ating oils In general, excellent detergent and antiwear properties can be imparted tolubric'ating oils by dissolving therein a quantity of from about 0.1 to 10% by weight of the polymers of the type described above, although a preferred range is from'about 1 to 5% by weight.
  • the polymers of this invention are unusually compatible with mineral and other lubricating oils in substantially all proportions, as much as 75% of the present polymerie additives can be dissolved in asuitable lubricating oil for the purpose of preparing a con- Qentrate capable of diluticnwith lubricating oils and the e'j fir pare j the anar "lubricant composition.
  • Such con cer 1trates-,jwhiclrjnay also contain other additives in desired amounts and which normally contain at least 10% of the po1yme'r,"compr ise a convenient method for handling the" polymer and maybe used as a compoundingagent for lubricants in general.
  • the polymeric additives of this invention can be used with good efiect inthe case of any one of a wide variety of oils of lubricatingviscosity, jor'of blends of such oils.
  • the base oil can be a refined Pennsylvania or other paraffin base oil, a refinednaphthenic base oil, or a synthetic hydrocarbonor nonhydrocarbon oil of lubricating viscosity.
  • synthetic oils there can be mentioned alkylated waxes ,and similar alkylated hydrocarbons of relatively high molecular weight, hydrogenated polymers 'of hydrocarbons; and theconden sation products or chl'orinatedalkylhydrocarbons with ethyl compounds.
  • 'Other suitable oils are those which are obtained by polymerization of lowermolecular'weight alkylene oxides such as propylene and/or ethylene oxide. Stillother synthetic oils areobtained by 'etherifica'tio'n' and/or este'rification of the hydroxy groups amylase oxide polymers such as, for example, the acetate of the z-ethylhexanol-initiated polymer of propylene oxide".
  • Other important classes of synthetic oils include the variousesters as, for example,
  • the present invention also contemplates the addition to the lubricant composition (particularly when the amount of copolymer em w ea'is relatively small) of auxiliary detergents and/or anti-wear agents.
  • Illustrative lubricant compositions of the above type containing the copolymeric additives of the invention in combination with'other agents may include, for example, from about'0.1 to 10% by weightof alkaline earth metal higher alkylphenate detergent and wear reducing agents such'as calcium alkylphenates having anaverage of approximately 14 carbon atoms in the alkyl group as well organic thiophosphate corrosion and high temperature oxidation inhibitors such as the reaction product of pin'ene and P 8 and the bivalent metaldihydrocarbyl dithiophosphates, zinc butyl hexyl dithiophosphate and zinc tetradecylphenyl dithiophospliate .in amounts of from about 0.
  • Temperature-viscosity improvingagents which may be employed in the tamponsa usually in amounts of from about 1 to 10% by weight, include by way of example the homopolymers of alkylmethacrylates such as the dodecyl methacrylate polymers known to the .trade as Acryloid 710 and Acryloid 763; products of Rohm &
  • the-16w temperature detergency of the oils tested is measured by determining the ability of the oil to solubilize and retain typical engine fuel deposits and precursors thereof which are formed due to incomplete combustion of the fuel. Retention of these deposits in a given oil depends upon their dispersal and upon minimizing their polymerization to lacquer.
  • the lacquer deposition test involves condensing fresh cool flame oxidation products from a standard test fuel simulating the fuel combustion products of an internal combustion engine in a steel vessel containing a certain amount of the lubricating oil being tested.
  • the steel surface of the vessel acts as an iron catalyst for polymerization of the fuel oxidation products to lacquer in the same manner as the steel surfaces in an internal combustion engine.
  • the steel vessel containing the lubricating oil is heated for 24 hours at a temperature selected to correspond with actual engine conditions.
  • the test oil is then decanted while hot from the lacquer deposits formed in the steel vessel due to polymerization and the lacquer deposits are de-oiled and weighed.
  • a low grade gasoline is employed of the type described in connection with the standard FL-2 test procedure given below.
  • the gasoline at a rate of 13.3 cc. per hour is vaporized and mixed with air, the air rate being 1.75 liters per minute.
  • the vapor mixture of gasoline and air is then fed into an elongated cool flame combustion chamber of standard design having a diameter of 1 /2 inches.
  • the cool flame combustion chamber is maintained at 695 F.
  • the test is continued for 1 hour during which the oxidation products issuing from the cool flame combustion chamber are condensed into the weighed steel catalyst vessel which contains 30 g. of the oil being tested at about room temperature.
  • the steel vessel containing test oil and condensed oxidation products is then heated for 24 hours at 110 F.
  • the oil is decanted from the lacquer deposits in the vessel, following which the deposits are de-oiled by washing with petroleum solvent.
  • the increase in weight of the steel vessel due to the lacquer deposits is then determined and recorded in milligrams as LD or lacquer deposit.
  • lacquer deposit for any given lubricant composition obtained in accordance with the procedure described above is directly correlated to the piston varnish rating or PVR obtained for the same lubricant composition in the standard FL-2 test procedure previously referred to and hereinafter more particularly described.
  • Table II which follows gives the correlated values for both the lacquer deposits and piston varnish ratings.
  • Table II LD PVR LD PVR The correlated values in the above table provide an accurate means for estimating from the lacquer deposits determined for a given oil the piston varnish rating to be obtained in the standard FL-2 Chevrolet engine test.
  • Table III gives the test data showing piston varnish ratings of various lubricant compositions and Table IV gives the test data showing lacquer deposit.
  • Table III Piston varnish rating Lubricant composition Base oil alone 3. 0 1.5% copolymer of (1) dodccyl methacrylate, (2) methacrylic acid and (3) nonaethylene glycol methacrylate in base oil 1.5% copolyrner of (l) dodecyl methacrylate, (2) methacrylic acid and (3) nonaethylene glycol methacrylate in base oil 1.5% copolymer of (l) dodecyl methacrylate, (2) methacrylic acid and (3) dodecylether of decaethylene glycol methacrylate in base 011..
  • Table IV 1 I copolymer of dodecyl methacrylate. wlth dodecyl ether! Ratio of (l) Lacquer capped polyethylene glycol (1600 mol. wt.) methacrylate Lubricant com osltton monomer to (2) deposit P monomerw (3) (mm and its evaluation as a dispersant.
  • The, product had dtethylamlnoethyl methacrylate in base nil 1 H d d th 1 t 14 10/1 1/1 244 an alkyl to dodecyl ether-capped polyethylene glycol 2.87 copo ymer o 1 o ecy me acrya e,
  • Base oil alone Mixed hexyloctyl orthosilicate 45. 2 33. 5 183 2.8% copolymer of (1) octadecene, (2) di-Z-ethylhexyl fumarate, do 10/15/3/1 47. 5 34.3 210 (3) crotonic acid and (4) tridecylether of decaethylene glycol methacrylate in base oil.
  • Base oil alone Ogtyloxyoetapropylene glycol acetate- 86. 6 39.
  • EXAMPLE VIII This example shows the copolymerization of dodecylmethacrylate, dodecyl ether-capped polyethylene glycol 1600 mol. wt.) methacrylate, and 4-vinyl pyridine.
  • EXAMPLE IX This example shows the copolymerization of dodecyl methacrylate, dodecyl ether-capped-polyethylene glycol (1600 mol. wt.) methacrylate, and glycidyl methacrylate.
  • EXAMPLE X This example shows the copolymerization of dodecyl methacrylate, dodecyl ether-capped polyethylene glycol (1600 mol. wt.) methacrylate and N,N-diethyl-aminoethyl methacrylate.
  • EXAMPLE XII This example shows copolymerizationof dodecyl methacrylate, dodecyl ether-capped polyethylene glycol (1600 mol. wt.) methacrylate, and methacrylarnide.
  • EXAMPLE XrII v i This example shows copolymerization of dodecyl methacrylate, dodecyl ether-capped polyethylene glycol (1600 mol. wt.) methacrylate, and N-vinyl carbazone.
  • glycol Charge 1 v 106 g. dodecyl methacrylate (0.418 mole) 13.5 g. dodecyl ether-capped polyethylene glycol v 1600 11101. wt.)-n1ethacrylate i 1.79 g. N-vinyl carbazole (0.009 mole) 209 g. benzene. Catalyst level 0.006% Conversion in 8 hours was 98% Ratio 86:1:1.2 2.8% in 150 neutral gave vis. at
  • EXAMPLE XIV This example shows copolymerization of dodecyl methacrylate, dodecyl ether-capped polyethylene glycol 1600 'mol. wt.) methacrylatqand 'acrylonitrile.
  • EXAMPLE xv This example shows copolymerization of dodecyl methacrylate with diethylamine initiated polyethylene glycol 2000 methacrylate.
  • the method of polymerization was as in the above examples.
  • the charge was 40 g. allylamine initiated polyethylene glycol (750; WL), (0.0251mol'e), 20 g. do! decyl methacrylate (0.079 mole) and 108: g. benzene.
  • Catalyst level was 0.015%.
  • azobisisobutylnitrile 60 g. dodecyl methacrylate and 108 g-.. benzene were added over five hours.
  • the polymerization was run for eight hours. Conversion was 82%.
  • To the reaction mix was added 100 g. of 150 neutral mineral lubricating oil1and. the benzene was, distilled off. Threevolmnes of mixed hexanes were added.
  • The. mixture was stirred at 130 F. for four hours, allowed to stand overnight, and the insolubles were separated by centrifiigation to dehaze the mixture.
  • the monomer ratio after this dehazing was 135 to 1'.
  • the asphaltene test showed the copolymer as having dispersing properties.
  • EXAMPLE. XVIII This example; illustrates. the polyglycol polymers in which the. 1 polyglycol chains. are. attached. to. a preformed polyisobutylene backbone via phosphonyloxy groups.
  • the dried polymer product upon analysis, was found to contain 0.34, 0.37% phosphorus corresponding to approximately 117 isobutylene units per glycol phosphonate group.
  • the average molecular weight was estimated as 60,000. 2.8% of the polymer in 150 neutral mineral lubricating oil had the following viscosity-temperature characteristics:
  • the polymer obtained abovev was purified by repeated precipitation with methanol. The yield of polymer was 7.2%.. Thedried. polymer was analyzed and' found to contain 1.43, 1.41% sulphur. The average molecular weight was 160,000. 2.8% of the polymer in 1.50 neutral mineral lubricating oil' had the following viscosity temperature characteristics:
  • a lubricant composition comprising. a major'portion of an oil of lubricating viscosity'and a minor portion suflicient to enhance the detergent characteristics of the composition of an oil-soluble polyglycol substituted poly mer of at least one monomer, said monomer containing of polyglycol groups, said oil-solubilizing groups being selected from the class consisting of aliphatic and cycloaliphatie hydrocarbon groups of at least 4 carbon atoms each, said polyglycol groups being selected from the class consisting of polyalkylene glycols and monoalkyl ethers thereof having from 2 to 7 carbon atoms in each alkylene group and a molecular weight between about 220 and 30,000, said polymer being substantially saturated and having a total molecular weight of at least about 50,000 and a solubility in oil of :at least 0.5% by weight, said polyglycols having at least alkylene oxide units each and being attached by a single thermally stable organic linking group to said polymer.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion suflicient to enhance the detergent characteristics of the composition of an oil soluble polyglycol substituted polymer of at least one monomer of the class consisting of olefins of from 2 to 30 carbon atoms, unsaturatedethers and unsaturated esters, said monomer containing a single polymerizable ethylenic bond and said polymer containing from about 40 to about 96% by weight of hydrocarbon oil-solubilizing groups from said polymerized monomer and from about 4 to about 60% by weight of polyglycol groups, said oil-solubilizing groups being selected from the class consisting of aliphatic and cycloaliphatic hydrocarbon groups of at least 4 carbon atoms each, said polyglycol groups being selected from the class consisting of polyalkylene glycols and monoalkyl ethers thereof having from 2 to 7 carbon atoms in each alkylene group and a molecular weightbetween
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion sufiicient to enhance the detergent characteristics of the composition of an oil-soluble polyglycol substituted poly mer of at least one monomer, said monomer containing a single polymen'zable ethylenic bond and said polymer containing from about 40 to about 96% by weight of hydrocarbon oil-solubilizing groups from said polymerized monomer and from about 4 to about 60% by weight of polyglycol groups, said oil-solubilizing groups being selected from the class consisting of aliphatic and cycloaliphatic hydrocarbon groups of at least 4 carbon atoms each, said polyglycol groups being selected from the class consisting of polyalkylene glycols and monoalkyl ethers thereof having from 2 to 7 carbon atoms in each alkylene group and a molecular weight between about 220 and 30,000, the polyglycol groups each being linked to said polymer by a single thermally stable organic linking group
  • a lubricant composition comprising a major portion of anoil of lubricating viscosity and a minor'portion, sufficient to enhance the detergent characteristics of the composition, of an oil-soluble polymer of mono mers, selected from at least each of the first two classes of the classes consisting of (A) polymerizable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from'4 to 30 aliphatic carbon atoms, (B) at least one ester of a,fi-ethylenically unsaturated monocarboxylic acids of from 3 to 15 carbon atoms each, in which the alkyl groups contain from 1 to 4 carbon atoms each, the carboxylgroups of said acids being monoester-linked to a member of the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30,000 and from 2 to 7 carbon atoms in each alkylene group and monoalkyl ethers thereof, and (
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion, suflicient to enhance the detergent characteristics of the composition, of an oil-soluble polymer of (A) polymerizable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 4 to 30 aliphatic carbon atoms, (B) at least one ester of a,fl-ethylenically unsaturated monocarboxylic acids of from 3 to 15 carbon atoms, in which the alkyl groups contain from 1 to 4 carbon atoms each, the carboxyl groups of said acids being monoester-linked to-a member of the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30,000 and from 2 to 7 carbon atoms in each alkylene group and monolkyl ethers thereof, and (C) acidic compounds selected from the group consisting of a, 3-ethylenically uns
  • lubricant composition comprising a major portion; t an oil, of lubricating viscosity and a minor portion sufiicient to enhance the detergent characteristics of the composition, of an oil-soluble polymer of (A) polymerizable' oil-solubilizing compounds having a single ethylenic linkage and'containinga monovalent hydrocarbongroup of from 4 to 30 aliphatic carbon atoms and B),- at least. one ester ofi m, 3-ethylenically unsaturated monocarboxylic acids of' from ⁇ to 15 carbonatoms, in
  • the polymer composition there being presentat-least one monomer of said (B) component and said polymer having a molecular weight of atleast 50,000 anda solubility in oil of atleast 0.5%, byweight, said n lyglycols having; at least 5' alkylene oxide units. each.
  • the alkyl groups contain from 1 to 4 carbon atoms each,. anhydrides thereof: and. monoesters of said dicarboxylic acids with an alcohol selected from the group consisting of polyalkylene. glycols. and ethers thereof as defined in (B.-) and' aliphatic hydrocarbon alcohols of from 8'1t0. 30. carbon. atoms, said (A) component constituting;from about 40 to 96% by weight and. said- (B). and (C3); components. constituting from about 4: to. 60% by. weight of*thepolymer composition, there being'presentl atleast' 4% by weightof said (B component. and said polymer-having amolecular-weight of at least 50,000 and a-solubility'in. oil: ofi at least 0.5% by: weight,- said polyglycols. having at least 5 alkylene oxide units each.
  • a lubricant composition comprising'a major portionof mineral lubricating oil and a minoriportion; .suf.-. ficient to enhance the.detergent'characteristics ofthe composition, of an oil-solublepolymer of A) polymerizable oil-solubilizing.
  • component constituting-- a. total of from about 4 to. 60% by weight of the polymer composition, there'being presout at least one monomer of said (B) component and saidpolymer. having a, molecularweight of at least 50,000 and a solubility inl oil of at least 0.5 %l by' weight, said polyglycols: having; at-least. 5- alkylene oxide units each.
  • a lubricant. composition comprising a major portion of mineral lubricating oil and from about 0.1 to 10% by weightof an oil soluble polymer of (A) polymerizableoil-solubilizing compounds having a single ethylenic linkage andcontaining: a monovalenthydrocarbon group'oif front- 4 to 3.0 aliphatic carbon atoms, (B) at least one ester of e,fl-ethylenically unsaturated monocarboxylic acids ofzfrom 3- to 15 carbon atoms, in which the alkyl groups containafrom- 1- to 4 carbon atoms each, the carboxyl groups of said acids being monoester-linked to a member of the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30g000 andfrom 2' to 7 carbon atoms in each alkylene group and monoalkyl ethers thereof, and.
  • a lubricant. composition comprising a major portion of mineral lubricating oil and from about 0.1- to 10%. by weight of: an oil-soluble polymer of (A) polymerizable oil-solubilizing compoundshaving a single ethylenic linkage and containinga monovalent hydrocarbon group of from 4 to.;30 aliphatic carbon atoms and (B) at. least one ester. of a,;3.-ethylenically unsaturated monocarboxylic acids offrom 3-to 1'5carbon atoms, in which the alkyl groups' containfrom 110 4 carbonatoms each,
  • the carboxyl groups of said acids being monoester-linked to amember of the group consisting of polyalkylene glycolshaving a molecular weight between about 220 and 30,000 and from-'2 to 7 carbonatoms in each alkylene group and;monoalkyl ethers thereof, said (A)-component constituting'frorn about. 40. to 96% by. weight and said (B) component constituting a total of from about 4 to 60% by. weightv of the polymer composition, there being present at leastone-monomer of said. (B) component and said polymerhaving-amolecular weight of at least 50,000 and asolubility in. oil of atfleast 0.5% by weight, said polyglycolsliavingat least 5 alkylene oxide units each.
  • A.lubricant.composition according to claim 13 in which the polyglycol is polyethylene glycol and there is included from about 0.1 to 10% by weight of. an oilsoluble alkaline earth metal alkyl phenate.
  • An addition agent capable of imparting enhanced detergent and antiwear characteristics to a lubricating oil consisting essentially of an oil of lubricating viscosity and from about to 75% by weight of an oil-soluble polymer of (A) polymerizable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 4 to 30 aliphatic carbon atoms and (B) at least one ester of fi-ethylenically unsaturated monocarboxylic acids of from 3 to carbon atoms, in which the alkyl groups contain from 1 to 4 carbon atoms each, the carboxyl groups of said acids being monoester-linked to a member of the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30,000 and from 2 to 7 carbon atoms in each alkylene group and monoalkyl ethers thereof, said (A) component constituting from about 40 to 96% by weight and said (B) components constituting a total of from
  • a lubricating composition comprising a major portion of a mineral lubricating oil and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) an alkyl methacrylate having an alkyl group of from 8 to 30 carbon atoms, (B) esters of methacrylic acid wherein the carboxyl group of said acid is monoester-linked to polyethylene glycols having an average molecular weight between about 400 and 10,000 and (C) methacrylic acid, said (A) component constituting from about 40 to 96% by weight and said (B) and (C) components constituting from about 4 to 60% by weight of the polymer composition, there being present at least 4% by weight of said (B) component, and said polymer having a molecular weight of at least 50,000 and a solubility in oil of at least 0.5% by weight.
  • an oil-soluble polymer of (A) an alkyl methacrylate having an alkyl group of from 8 to 30 carbon atoms, (B) esters of methacrylic
  • a lubricating composition comprising a major portion of a mineral lubricating oil and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) an alkyl methacrylate having an alkyl group of from 8 to 30 carbon atoms and (B) esters of mcthacrylic acid wherein the carboxyl groups of said acid are monoester-linked to monoalkyl ethers of polyethylene glycols having an average molecular weight between about 400 and 10,000, said (A) component constituting from about 40 to 96% by weight and said (B) component constituting from about 4 to 60% by weight of the polymer composition, there being present at least one monomer of said (B) component and said polymer having a molecular weight'of at least 50,000 and a solubility in oil of at least 0.5% by weight, said polyglycols having at least 5 alkylene oxide units each.
  • an oil-soluble polymer of (A) an alkyl methacrylate having an alkyl group of from 8 to 30 carbon
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion sufiicient to enhance the detergent characteristics of the composition of an oil-soluble polymer of monomers selected from at least each of the first two classes of the classes consisting of (A) polymerizable oil-solubilizing esters having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 8 to 30 aliphatic carbon atoms, (B) esters selected from the group consisting of monoesters and diesters of a,fi-ethylenically unsaturated u,B-dicarboxylic acids of from 4 to 12 carbon atoms each in which the alkyl groups contain from 1 to 4 carbon atoms each and wherein the carboxyl groups of said acids are monoester-linked to a member of the group consisting of aliphatic alcohols of from 8 to 30 carbon atoms and polyalkylene glycols having a molecular weight between about 220
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and from about 0.1 to 10% by weight of an oil-soluble'polymer of (A) a polymerizable oil-solubilizing ester having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 8 to 30 aliphatic carbon atoms, and (B) esters selected from the group consisting of monoesters and diesters of a,fl-ethylenically unsaturated a,fi-dicarboxylic acids of from 4 to 12 carbon atoms each in which the alkyl groups contain from 1 to 4 carbon atoms each and wherein the carbonyl groups of said acids are monoester-linked to a member of the group consisting of aliphatic alcohols of from 8 to 30 carbon atoms and polyalkylene glycols and monoalkyl ethers thereof having from 2 to 7 carbon atoms in each alkylene group and a molecular weight between
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) a polymerizable oil-solubilizing ester having a single ethylenic linkage and containing a'monovalent hydrocarbon group of from 8 to 30 aliphatic carbon atoms,
  • esters selectedfrom thegroup consisting: of mono esters and diesters of a,B-ethylenically unsaturated (1,5- dicarboxylic acids of. from 4 to' 12. carbon atoms each in which the alkyl groupsv contain from 1 to 4 carbon atoms each and wherein the carboxyl groups of said acids are monoester-linked to a member: of the group consisting of aliphatic alcohols of from 8 to 30 carbon atoms and polyethylene glycols having a molecular weight between about: 220 and 30,000, only one of the terminal.
  • hydroxyl groups of said polyethylene glycols be ng linked:to said carboxylgroupsand at least one of said monoester-linked members being said polyethylene glycol, and (C) acidic compounds selected from the group consisting of w,/3-ethylenically' unsaturated monocarboxylic acids of from 3' to carbon atoms each in which the alkyl groups contain from 1 to 4 carbon atoms each, a,fl-ethylenicallyunsaturated 0:,[3-(liCfl1bOXY1iC acids of from to 12 carbon atoms each in which the alkyl groups contain from 1 to 4 carbon atoms each, anhydrides and monoesters of said dicarboxylic acids, the alcohol portion of the ester group being aliphatic hydrocarbon containing from 8 to 30 aliphatic carbon atoms, said oil-soluble polymers having a molecular weight of at least 50,000, from about 40 to 96% by weight of the oil-solubilizing component (A
  • a lubricant composition comprising a'major portion of an oil of lubricating viscosity andfrom about 0.1 to 10% by weight of an oil-soluble polymer of (A) dodecyl met-hacrylate, (B) mono(dodecyloxy) hexadecaethylene glycol maleate and (C) maleic anhydride, said oil-soluble polymers having a molecular weight of at least 50;000, from about 40 to 96% by weightof the oil-solubilizing component (A), from about 4 to 60% by' weight of components (B) and (C) and a solubility in oil of at least 0.5% by weight, there being present at least 4% by weight of said (B) component.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) a mixture ofallyl stearate and dodecyl methacrylate, (B) mono(methoxy dodecaethylene glycol) maleate and (C) maleic auhydride, said oil-soluble polymers having a molecular weight of at least 50,000, from about 40 to 96% by weight of the oil-solubilizing component (A) from about 4 to 60% by weight of components (B) and (C) and'a solubility in oil of at least 0.5% by weight, there being present at least 4% by weight of said (B) component.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) a mixture of dodecyl methacrylate" and allyl stearate, (B) mono-methoxy dodecaethylene glycol) maleate and (C) maleic anhydride, said. oil-soluble polymers having a molecular weight of at least 50,000, from about 40 to 96% by weight of the oil-solubilizing component (A), from about 4 to 60% by weight of components (B) and (C) and a solubility in oil of at least 0.5 by weight, there being present at least 4% by weight of said (B) component.
  • a lubricant composition comprising a major portion of an oil of' lubricating viscosity and a minor portionsufiicient to enhance the detergent characteristics of the. compositionv of anIoilvsoluble'polymer of monomers selected from at least each.
  • a lubricant composition comprising a major portion. of a mineral lubricating oil and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) dodecyl methacrylate, (B) tridecyl ether of decaethylene glycol monomethacrylate and (B) ethylene glycol monomethacrylate; said oil-soluble copolymer having a molecular weight of at least 50,000, from about 40 to 96% by weight of theoil-solubilizing component.(A) from about 4m 60% by weight of the- (B) and (B) componentsand a solubility in oil of at least 0.5 by weight, therebeing present at least 4% by weight of said (B) component.
  • a lubricant composition comprising a major portion of an oil of lubricating-viscosity, together with from 0.1. to l'0.%by weight, of a polymer of (A) ahigher. alkyl ester of an a,B-ethylenically unsaturated monocarboxylic acid. of from 3 to 8' carbon atoms in which the alkyl groupcontains from 8 to 30 carbon atoms, (B) esters of an a,fl-ethylenically unsaturated monocarboxylic acid of from 3 to- 8 carbon atoms each wherein the carboxyl groups.
  • said monocarboxylic acid are monoester-linked to a polyethylene glycol having an average molecular weight between about 400 and 10,000, and (B) esters ofv the monocarboxylic acids as defined in (B) wherein the carboxyl groups of said monocarboxylic acids are monoester-linked' to an alkyl polyhydric alcohol of not more than 7 carbon atoms, said polymer havinga molecular weight of atv least 50,000, from about 40 to 96% by weight of the oil-solubilizing component (A), from about 4 to 60% by weight of the (B) and (B) components and a solubility in-oil of at least 0.5 by weight, there. being present at least 4% by weight. of said (B) component.
  • a lubricant composition comprising a major portion of an oil of. lubricating viscosity, together with from 0.1 to 10% by weight, of a polymer of (A) a higher alkyl. ester of an a,;3-ethylenically unsaturated monocarboxylic acid of from 3 to 8 carbon atoms in which the-alkyl group contains from 8 to 30 carbon atoms, (B) esters of'an a,fi-ethylenically unsaturated monocarboxylic acid of from 3 to 8 carbon atoms each wherein the carboxyl groups of said monocarboxylic acid are monoester-linked to a. polyethylene glycol.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion sufiicient to enhance the detergent characteristics of the composition of an oil-soluble polymer of monomers selected from at least each of the first three classes consisting of (A) polymerizable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 4 to 30 aliphatic carbon atoms, (B) esters of acidic compounds selected from the group consisting of a,B-ethylenically unsaturated monocarboxylic acids of from 3 to "8 carbon atoms each and a, 8-ethylenically unsaturated, a,fi-dicarboxylic acids of from 4 to 12 carbon atoms each in which the alkyl groups contain from 1 to 4 carbon atoms each and wherein the carboxyl groups of said acidic compounds are monoester-linked to a member of the group consistingof polyalkylene glyco
  • a lubricant composition comprising a major portion of a mineral lubricating oil and from about 0.1 to by weight of an oil-soluble polymer of (A) dodecyl methacrylate, (B) tridecyl ether of decaethylene glycol methacrylate, (C) N-Z-hydroxyethyl methacrylamide and (D) acrylic acid, said oil-soluble polymer having a molecular weight of at least 50,000, from about 40 to 96% by weight of the oil-solubilizing component (A), from about 4 to 60% by weight of components (B), (C) and (D) and a solubility in oil of at least 0.5% by weight, there being present at least 4% by weight of said (B) component.
  • a lubricant composition comprising a major portion of a mineral lubricating oil and from about 0.1 to 10% by weight of an oil-soluble polymer of (A) dodecyl methacrylate, (B) dodecyl ether of decaethylene glycol methacrylate, (C) heptadecenyl-2-hydroxyethyl imidazoline methacrylate, and (D) methacrylic acid, said oilsoluble polymer having a molecular weight of at least 50,000, from about 40 to 96% by weight of the oilsolubilizing component (A), from about 4 to 60% by weight of components (B), (C) and (D) and a solubility in oil of at least 0.5% by weight, there being present at least 4% by weight of said (B) component.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion sufiicient to enhance the detergent characteristics of the composition of an oil-soluble polyglycol substituted polymer of olefins of from 2 to 30 carbon atoms, said polymer containing from about 40 to about 96% by weight of hydrocarbon oil-solubilizing groups from 34 said polymerized olefins and from about 4 to about 60% by weight of polyglycol, groups, said oil-solubilizing groups being selected from the class consisting of aliphatic and cycloaliphatic hydrocarbon groups of at least 4., carbon atoms each, said polyglycol groups being selected from the class consisting of polyalkylene glycols and monoalkyl ethers thereof having from 2 to 7 carbon atoms in each alky-lene group and a molecular weight between about 220 and 30,000, said polymer being substantia-lly saturated and having a total molecular weight of at least about 50,000
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion, suflicient to enhance the detergent characteristics of the composition of an oil-soluble polymer of (A) polymerizable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 4 to 30 aliphatic carbon atoms and (B) at least one monoalkenyl ether of a polyalkylene glycol selected from the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30,000 and from 2 to 7 carbon atoms in each alkylene group and monoalkyl ethers thereof, said alkenyl group having not more than 20 carbon atoms, said (A) component constituting from about 40 to 96% by weight and said (B) component constituting a total of from about 4 to 60% by weight of the polymer composition, there being present at least one monomer of said (B) component and said polymer being substantially saturated and
  • a lubricant composition according to claim 37 in which the compound (A) is alkyl methacrylate wherein the alkyl group contains from 8 to 30 carbon atoms and the polyglycol alkenyl ether of component (B) is vinyl ether of polyethylene glycol.
  • a lubricant composition according to claim 37 in which the compound (A) is alkyl methacrylate wherein the alkyl group contains from 8 to 30 carbon atoms and the polyglycol alkenyl ether of component (B) is vinyl ether of polypropylene glycol.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion sufiicient to enhance the detergent characteristics of the composition, of an oil-soluble polymer of (A) polymerizable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 4 to 30 aliphatic carbon atoms and (B) at least one N-alkenyl amino alkyl ether of a polyalkylene glycol selected from the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30,000, and from 2 to 7 carbon atoms in each alkylene group and monoalkyl ethers thereof, said alkenyl group having from 3 to 20 carbon atoms and said amino alkyl group having from 2 to 7 carbon atoms, said (A) component constituting from about 40 to 96% by weight and said (B) component consisting a total of from about 4 to 60% by Weight of the polymer composition
  • a lubricant composition according to claim 40 in which the (A) component is alkyl methacrylate wherein the alkyl group contains from 8 to 30 carbon atoms and the N-alkenyl ether is N-allyl amino ethyl monoether of polyethylene glycol.
  • a lubricant composition according to claim 40 in which the (A) component is alkyl methacrylate wherein the alkyl group contains from 8 to 30 carbon atoms and the N-alkenyl ether is N-allyl amino propyl monoether of polypropylene glycol.
  • a lubricant composition comprising a major portion of an oil of lubricating viscosity and a minor portion sufficient to enhance the detergent characteristics of the composition, of an oil-soluble polymer of (A) polymer-izable oil-solubilizing compounds having a single ethylenic linkage and containing a monovalent hydrocarbon group of from 4 to 30 aliphatic carbon atoms and (B) at least one ethylenically unsaturated acyl amido alkyl ether of a polyalkylene glycol selected from the group consisting of polyalkylene glycols having a molecular weight between about 220 and 30,000, and from 2 t0 7 carbon atoms in each alkylene group and monoalkyl ethers thereof, said acyl group having from 3 to 20 carbonatoms and saidamido alkyl group having from 2 to 7 carbon atoms, said (A) component constituting from about'40 to 96% by weight and said (B) component constituting a total of from about 4
  • Attest KARL H. AXLINE, ROBERT C. WATSON, Attesting Ofiaer, Ganwm'saiomr of Patents.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
US729560A 1958-04-21 1958-04-21 Lubricant composition Expired - Lifetime US2892783A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
NL238305D NL238305A (de) 1958-04-21
US729560A US2892783A (en) 1958-04-21 1958-04-21 Lubricant composition
BE577456D BE577456A (de) 1958-04-21 1959-04-07
GB12253/59A GB917923A (en) 1958-04-21 1959-04-10 Lubricant composition
FR791920A FR1225980A (fr) 1958-04-21 1959-04-13 Composition lubrifiante
NL238305A NL122867C (de) 1958-04-21 1959-04-18
DEC18835A DE1248204B (de) 1958-04-21 1959-04-21 Schmieroel
US821686A US3073807A (en) 1958-04-21 1959-06-22 Copolymers of olefins with sulfonyloxy compounds
US197839A US3189586A (en) 1958-04-21 1962-05-28 Detergent copolymer of unsaturated polyglycol ether
US427159A US3337516A (en) 1958-04-21 1965-01-21 Detergent copolymer of polyglycol alkenyl ethers
US661837A US3428615A (en) 1958-04-21 1967-08-21 Detergent copolymer acyl amido alkyl ethers of polyalkylene glycol

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US729560A US2892783A (en) 1958-04-21 1958-04-21 Lubricant composition
US821686A US3073807A (en) 1958-04-21 1959-06-22 Copolymers of olefins with sulfonyloxy compounds
US66183767A 1967-08-21 1967-08-21

Publications (1)

Publication Number Publication Date
US2892783A true US2892783A (en) 1959-06-30

Family

ID=32475432

Family Applications (5)

Application Number Title Priority Date Filing Date
US729560A Expired - Lifetime US2892783A (en) 1958-04-21 1958-04-21 Lubricant composition
US821686A Expired - Lifetime US3073807A (en) 1958-04-21 1959-06-22 Copolymers of olefins with sulfonyloxy compounds
US197839A Expired - Lifetime US3189586A (en) 1958-04-21 1962-05-28 Detergent copolymer of unsaturated polyglycol ether
US427159A Expired - Lifetime US3337516A (en) 1958-04-21 1965-01-21 Detergent copolymer of polyglycol alkenyl ethers
US661837A Expired - Lifetime US3428615A (en) 1958-04-21 1967-08-21 Detergent copolymer acyl amido alkyl ethers of polyalkylene glycol

Family Applications After (4)

Application Number Title Priority Date Filing Date
US821686A Expired - Lifetime US3073807A (en) 1958-04-21 1959-06-22 Copolymers of olefins with sulfonyloxy compounds
US197839A Expired - Lifetime US3189586A (en) 1958-04-21 1962-05-28 Detergent copolymer of unsaturated polyglycol ether
US427159A Expired - Lifetime US3337516A (en) 1958-04-21 1965-01-21 Detergent copolymer of polyglycol alkenyl ethers
US661837A Expired - Lifetime US3428615A (en) 1958-04-21 1967-08-21 Detergent copolymer acyl amido alkyl ethers of polyalkylene glycol

Country Status (6)

Country Link
US (5) US2892783A (de)
BE (1) BE577456A (de)
DE (1) DE1248204B (de)
FR (1) FR1225980A (de)
GB (1) GB917923A (de)
NL (2) NL122867C (de)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992184A (en) * 1957-11-19 1961-07-11 Exxon Standard Sa Lubricant compositions
US3001942A (en) * 1958-12-15 1961-09-26 California Research Corp Lubricant composition
US3010906A (en) * 1955-03-09 1961-11-28 Exxon Standard Sa Lubricating oil additives
US3018247A (en) * 1960-03-15 1962-01-23 California Research Corp Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
US3033790A (en) * 1958-06-17 1962-05-08 Shell Oil Co Lubricating composition
US3037056A (en) * 1959-03-30 1962-05-29 California Research Corp Amido polyglycols
US3041283A (en) * 1958-05-19 1962-06-26 Shell Oil Co Lubricating compositions
US3057803A (en) * 1958-04-12 1962-10-09 Roehm & Haas Gmbh Hydraulic fluids with polymeric viscosity index improvers
US3081261A (en) * 1960-08-25 1963-03-12 California Research Corp Lubricants containing lead dithiophosphates
US3189543A (en) * 1962-08-03 1965-06-15 California Research Corp Grease yields
US3216940A (en) * 1962-12-18 1965-11-09 California Research Corp Polymeric compositions and lubricants containing them
US4703087A (en) * 1985-12-21 1987-10-27 Wolff Walsrode Ag Water-soluble polymers and their use as auxiliaries for building materials
US4778869A (en) * 1979-05-29 1988-10-18 American Cyanamid Company Activated ester monomers and polymers
US5210166A (en) * 1985-11-07 1993-05-11 Basf Aktiengesellschaft Copolymers of ethylene with polyalkylene glycol (meth)acrylates
US5306437A (en) * 1991-11-30 1994-04-26 Hoechst Aktiengesellschaft Copolymers and their use as lubricants and release agents for processing thermoplastics
US5718821A (en) * 1991-07-18 1998-02-17 Hoechst Aktiengesellschaft Copolymers of ethylenically unsaturated carboxylic acid esters with polyoxyalkylene ethers of lower, unsaturated alcohols as flow-improving agents for paraffin containing oils

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL238305A (de) * 1958-04-21
US3194678A (en) * 1960-12-20 1965-07-13 Eastman Kodak Co Polymers cross-linked with sulfur dioxide, fabrics coated therewith, and coating method
US3255114A (en) * 1963-09-09 1966-06-07 Chevron Res Lubricant compositions
GB1112788A (en) * 1967-04-14 1968-05-08 Shell Int Research Lubricant compositions
US3652411A (en) * 1969-12-04 1972-03-28 Mobil Oil Corp Polyglycol base lubricant
US3966625A (en) * 1971-09-23 1976-06-29 Nippon Oils And Fats Company Limited Lubricating oil composition containing polyoxyalkylene glycol diether viscosity-index improvers
US3951831A (en) * 1975-01-17 1976-04-20 Rohm And Haas Company Antioxidant-containing viscosity index improvers for high temperature service
DE3112456A1 (de) * 1981-03-28 1982-10-07 Hoechst Ag, 6000 Frankfurt "verfahren zur verbesserung der fliessfaehigkeit von mineraloelen"
JPS60130640A (ja) * 1983-12-16 1985-07-12 Dainippon Ink & Chem Inc ビニル共重合体樹脂水分散液の製造方法
US4876384A (en) * 1985-04-22 1989-10-24 Diamond Shamrock Chemicals Co. Radiation-hardenable diluents
US5110889A (en) * 1985-11-13 1992-05-05 Diamond Shamrock Chemical Co. Radiation hardenable compositions containing low viscosity diluents
US5219965A (en) * 1990-11-27 1993-06-15 Bausch & Lomb Incorporated Surface modification of polymer objects
US5177165A (en) * 1990-11-27 1993-01-05 Bausch & Lomb Incorporated Surface-active macromonomers
DE4423358A1 (de) * 1994-07-04 1996-01-11 Roehm Gmbh Dispergierwirksame Cooligomere und Copolymere
EP1069139A3 (de) * 1999-07-13 2003-03-12 Clariant GmbH Wässrige Polymerdispersion, ihre Herstellung und Verwendung
US7135303B2 (en) 2000-02-28 2006-11-14 The United States Of America As Represented By The Department Of Health And Human Services Regulators of type-1 tumor necrosis factor receptor and other cytokine receptor shedding
JP5345274B2 (ja) * 2006-03-24 2013-11-20 株式会社日本触媒 炭化水素基含有グラフト重合体およびその製造方法
DE102006049381A1 (de) * 2006-10-19 2008-04-24 Süd-Chemie AG Amphiphile Pfropfpolymere
US8207099B2 (en) 2009-09-22 2012-06-26 Afton Chemical Corporation Lubricating oil composition for crankcase applications
US9708424B2 (en) 2011-09-27 2017-07-18 Kaneka Corporation (Meth)acryloyl-terminated polyisobutylene polymer, method for producing the same, and active energy ray-curable composition
JP6088972B2 (ja) * 2011-09-27 2017-03-01 株式会社カネカ （メタ）アクリロイル末端ポリイソブチレン系重合体、その製造方法、および活性エネルギー線硬化性組成物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2792382A (en) * 1952-11-26 1957-05-14 Phillips Petroleum Co Condensation products of alkene oxides and hydroxylated polymers of conjugated dienes and their preparation
US2824840A (en) * 1953-04-01 1958-02-25 Exxon Research Engineering Co Lubricating oil composition

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2189735A (en) * 1938-01-28 1940-02-06 Norton Co Resin bonded abrasive article
US2498656A (en) * 1948-05-29 1950-02-28 Petrolite Corp Processes for breaking petroleum emulsions
US2602079A (en) * 1948-11-12 1952-07-01 Petrolite Corp Oxyalkylated derivatives of resinous polymers of vinyl esters
US2637698A (en) * 1948-12-30 1953-05-05 Standard Oil Dev Co Mineral oil lubricating composition containing a copolymer of an alkyl ester of itaconic acid and an alkyl acrylate or methacrylate
US2737496A (en) * 1952-02-16 1956-03-06 Du Pont Lubricating oil compositions containing polymeric additives
GB759918A (en) * 1952-10-22 1956-10-24 California Research Corp Lubricant composition
NL206960A (de) * 1953-06-10
US2806842A (en) * 1955-10-24 1957-09-17 Colgate Palmolive Co Alkylene oxide graft copolymers
US2892818A (en) * 1956-03-26 1959-06-30 California Research Corp Detergent copolymers
US2892820A (en) * 1956-03-29 1959-06-30 California Research Corp Oil soluble polymers containing polyalkylene glycol side-chains
US2892819A (en) * 1956-03-29 1959-06-30 California Research Corp Detergent copolymers
NL238305A (de) * 1958-04-21

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2792382A (en) * 1952-11-26 1957-05-14 Phillips Petroleum Co Condensation products of alkene oxides and hydroxylated polymers of conjugated dienes and their preparation
US2824840A (en) * 1953-04-01 1958-02-25 Exxon Research Engineering Co Lubricating oil composition

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3010906A (en) * 1955-03-09 1961-11-28 Exxon Standard Sa Lubricating oil additives
US2992184A (en) * 1957-11-19 1961-07-11 Exxon Standard Sa Lubricant compositions
US3057803A (en) * 1958-04-12 1962-10-09 Roehm & Haas Gmbh Hydraulic fluids with polymeric viscosity index improvers
US3041283A (en) * 1958-05-19 1962-06-26 Shell Oil Co Lubricating compositions
US3033790A (en) * 1958-06-17 1962-05-08 Shell Oil Co Lubricating composition
US3001942A (en) * 1958-12-15 1961-09-26 California Research Corp Lubricant composition
US3037056A (en) * 1959-03-30 1962-05-29 California Research Corp Amido polyglycols
US3018247A (en) * 1960-03-15 1962-01-23 California Research Corp Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
US3081261A (en) * 1960-08-25 1963-03-12 California Research Corp Lubricants containing lead dithiophosphates
US3189543A (en) * 1962-08-03 1965-06-15 California Research Corp Grease yields
US3216940A (en) * 1962-12-18 1965-11-09 California Research Corp Polymeric compositions and lubricants containing them
US4778869A (en) * 1979-05-29 1988-10-18 American Cyanamid Company Activated ester monomers and polymers
US5210166A (en) * 1985-11-07 1993-05-11 Basf Aktiengesellschaft Copolymers of ethylene with polyalkylene glycol (meth)acrylates
US4703087A (en) * 1985-12-21 1987-10-27 Wolff Walsrode Ag Water-soluble polymers and their use as auxiliaries for building materials
US5718821A (en) * 1991-07-18 1998-02-17 Hoechst Aktiengesellschaft Copolymers of ethylenically unsaturated carboxylic acid esters with polyoxyalkylene ethers of lower, unsaturated alcohols as flow-improving agents for paraffin containing oils
US5306437A (en) * 1991-11-30 1994-04-26 Hoechst Aktiengesellschaft Copolymers and their use as lubricants and release agents for processing thermoplastics

Also Published As

Publication number Publication date
US3428615A (en) 1969-02-18
NL122867C (de) 1967-09-15
BE577456A (de) 1959-04-30
DE1248204B (de) 1967-08-24
US3337516A (en) 1967-08-22
GB917923A (en) 1963-02-13
US3189586A (en) 1965-06-15
NL238305A (de)
US3073807A (en) 1963-01-15
FR1225980A (fr) 1960-07-06

Similar Documents

Publication Publication Date Title
US2892783A (en) Lubricant composition
US3519565A (en) Oil-soluble interpolymers of n-vinylthiopyrrolidones
US2892786A (en) Lubricant composition
US3381022A (en) Polymerized olefin substituted succinic acid esters
US2993032A (en) Detergent copolymers
US3277157A (en) Polyoxyalkylene acrylates and methacrylates
US2892820A (en) Oil soluble polymers containing polyalkylene glycol side-chains
US3048544A (en) Lubricant composition
US3087893A (en) Copolymers of maleic anhydride and unsaturated esters as additives in oils
US2892793A (en) Lubricant composition
EP0204587A2 (de) Schmierölzusammensetzung
US2892816A (en) Detergent copolymers
US2892821A (en) Detergent copolymers
US2892788A (en) Lubricant composition
US2892819A (en) Detergent copolymers
US3001942A (en) Lubricant composition
US2892818A (en) Detergent copolymers
US2892792A (en) Lubricant composition
US3208945A (en) Rust resistant lubricant composition
US3046260A (en) Detergent copolymer
US2892791A (en) Lubricant composition
US3160612A (en) Detergent copolymer
US3048615A (en) Tertiary alkyl azomethine copolymers
US3192165A (en) Mineral oil composition
US3163605A (en) Lubricating oil additives