GB822620A - Lubricating oil additives - Google Patents

Lubricating oil additives

Info

Publication number
GB822620A
GB822620A GB24982/56A GB2498256A GB822620A GB 822620 A GB822620 A GB 822620A GB 24982/56 A GB24982/56 A GB 24982/56A GB 2498256 A GB2498256 A GB 2498256A GB 822620 A GB822620 A GB 822620A
Authority
GB
United Kingdom
Prior art keywords
vinyl
ester
pyrrolidone
oleophilic
copolymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB24982/56A
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.)
CHEMON CORP
Original Assignee
CHEMON CORP
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by CHEMON CORP filed Critical CHEMON CORP
Publication of GB822620A publication Critical patent/GB822620A/en
Expired 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
    • 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
    • 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
    • C08F220/1802—C2-(meth)acrylate, e.g. ethyl (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
    • 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
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (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
    • 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
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M2217/06—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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

A lubricating composition comprises a lubricating oil such as a petroleum base oil or a sebacate and up to 10% by weight of a copolymer of an N-vinyl pyrrolidone and an oleophilic ester containing olefinic unsaturation, in which ester oleophilic characteristics can be conferred by either the alcohol or acid moiety of the ester, the average length of the oleophilic alcohol or acid moiety of the ester ranging from 6 to 18, preferably 12 to 18, carbon atoms, and the N-vinyl pyrrolidone constituting from 5 to 50% by weight of the copolymer (see Group IV (a)). Preferred copolymers are those of N-vinyl-2-pyrrolidone with an acrylate or methacrylate of lauryl, myristyl, cetyl or stearyl alcohol or of commercially available mixtures thereof, or with vinyl caprylate. In an example, the copolymer also incorporates n-butyl methacrylate. A coating process comprises pouring on to an aluminium sheet a viscous mass obtained by copolymerizing N-vinyl-2-pyrrolidone and the acrylic acid ester of a C12-14 alkanol mixture in the presence of toluene, followed by baking for four hours at 150 DEG C. Aluminium and glass may be coated in a similar manner with a copolymer of N-vinyl-2-pyrrolidone and vinyl caprylate.ALSO:Relates to oil-soluble copolymers of an N-vinyl pyrrolidone and an oleophilic ester containing olefinic unsaturation, the oleophilic characteristics of the ester being conferred by either the alcohol or acid moiety of the ester, the average length of the oleophilic alcohol or acid moiety of the ester ranging from 6 to 18, preferably 12 to 18, carbon atoms, and the N-vinyl pyrrolidone constituting from 5 to 50% by weight of the copolymers. The N-vinyl pyrrolidone may be N-vinyl-2-pyrrolidone or a 3-methyl-, 5,5-dimethyl-, 3,3,5-trimethyl-, 3,5,5-trimethyl-, 3,3-dimethyl-5-alkyl-, 3,3-dimethyl-5-alkenyl- or 3,3-dimethyl-5-methoxy-N-vinyl pyrrolidone. The ester may be an acrylate or methacrylate of lauryl, myristyl, cetyl or stearyl alcohol or of commercially available mixtures thereof, or may be vinyl caprylate. Other monomers such as n-butyl methacrylate may be incorporated in the copolymer. Polymerization may be effected in solution in toluene, a heavy hydrocarbon oil or a chlorinated hydrocarbon, in the presence of a catalyst such as benzoyl, lauryl or acetyl peroxide, diisopropylbenzene or tertiary butyl hydroperoxide, azodiisobutyronitrile or a mixture of a hydroperoxide with a quaternary ammonium compound. The polymerization reaction may be stopped at a desired degree of polymerization by quenching with a solvent such as an oil. During the polymerization reaction a solution of catalyst in the solvent used may be added incrementally. The copolymers of the invention may be used as oil additives or to produce coatings which adhere to aluminium and glass.
GB24982/56A 1955-08-31 1956-08-15 Lubricating oil additives Expired GB822620A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA330141X 1955-08-31

Publications (1)

Publication Number Publication Date
GB822620A true GB822620A (en) 1959-10-28

Family

ID=4171420

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24982/56A Expired GB822620A (en) 1955-08-31 1956-08-15 Lubricating oil additives

Country Status (3)

Country Link
CH (1) CH330141A (en)
FR (1) FR1161098A (en)
GB (1) GB822620A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3116248A (en) * 1960-12-23 1963-12-31 Shell Oil Co Lubricating oil composition
US3153632A (en) * 1960-06-15 1964-10-20 Shell Oil Co Power transmission fluids
US3208945A (en) * 1963-05-31 1965-09-28 California Research Corp Rust resistant lubricant composition
US3215631A (en) * 1963-02-08 1965-11-02 Shell Oil Co Lubricants containing ashless nitrogencontaining polymeric detergents and complexes of acid aryl phosphates
US3328283A (en) * 1965-01-06 1967-06-27 Petrolite Corp Hydrocarbon inhibitors for use in oil refinery heat exchanger
US3328285A (en) * 1965-01-06 1967-06-27 Petrolite Corp Hydrocarbon inhibitor for use in heat exchangers of oil refinery equipment
US3372120A (en) * 1961-02-21 1968-03-05 Lubrizol Corp Lubricants containing polymeric additives
WO2010003892A1 (en) * 2008-07-10 2010-01-14 M-I Swaco Norge As Method of improving the cold flow properties of a paraffin-containing fluid

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL260895A (en) * 1960-02-26
BE608231A (en) * 1960-09-15
DE4139963A1 (en) * 1991-12-04 1993-06-09 Basf Ag, 6700 Ludwigshafen, De REDISPERIBLE DISPERSION POWDER OF N-VINYLPYRROLIDONE VINYL ACETATE COPOLYMERISATE, THE PRODUCTION AND USE THEREOF

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3153632A (en) * 1960-06-15 1964-10-20 Shell Oil Co Power transmission fluids
US3116248A (en) * 1960-12-23 1963-12-31 Shell Oil Co Lubricating oil composition
US3372120A (en) * 1961-02-21 1968-03-05 Lubrizol Corp Lubricants containing polymeric additives
US3215631A (en) * 1963-02-08 1965-11-02 Shell Oil Co Lubricants containing ashless nitrogencontaining polymeric detergents and complexes of acid aryl phosphates
US3208945A (en) * 1963-05-31 1965-09-28 California Research Corp Rust resistant lubricant composition
US3328283A (en) * 1965-01-06 1967-06-27 Petrolite Corp Hydrocarbon inhibitors for use in oil refinery heat exchanger
US3328285A (en) * 1965-01-06 1967-06-27 Petrolite Corp Hydrocarbon inhibitor for use in heat exchangers of oil refinery equipment
WO2010003892A1 (en) * 2008-07-10 2010-01-14 M-I Swaco Norge As Method of improving the cold flow properties of a paraffin-containing fluid
AU2009268130B2 (en) * 2008-07-10 2012-05-10 Schlumberger Norge As Method of improving the cold flow properties of a paraffin-containing fluid

Also Published As

Publication number Publication date
FR1161098A (en) 1958-08-20
CH330141A (en) 1958-05-31

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