GB759918A - Lubricant composition - Google Patents

Lubricant composition

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Publication number
GB759918A
GB759918A GB27404/53A GB2740453A GB759918A GB 759918 A GB759918 A GB 759918A GB 27404/53 A GB27404/53 A GB 27404/53A GB 2740453 A GB2740453 A GB 2740453A GB 759918 A GB759918 A GB 759918A
Authority
GB
United Kingdom
Prior art keywords
alpha
polypolar
alcohol
copolymer
aliphatic
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
GB27404/53A
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
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Publication date
Application filed by California Research LLC filed Critical California Research LLC
Publication of GB759918A publication Critical patent/GB759918A/en
Expired legal-status Critical Current

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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10Macromolecular 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
    • C10M145/12Macromolecular 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 monocarboxylic
    • C10M145/14Acrylate; Methacrylate
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    • C10M143/00Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
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    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/04Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol, aldehyde, ketonic, ether, ketal or acetal radical
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    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10Macromolecular 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
    • C10M145/16Macromolecular 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 polycarboxylic
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    • C10M149/00Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M159/00Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/005Macromolecular compounds, e.g. macromolecular compounds composed of alternatively specified monomers not covered by the same main group
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102Aliphatic fractions
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104Aromatic fractions
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    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106Naphthenic fractions
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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    • C10M2203/108Residual fractions, e.g. bright stocks
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    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/082Macromolecular 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 monocarboxylic
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/084Acrylate; Methacrylate
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/086Macromolecular 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 polycarboxylic, e.g. maleic acid
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    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2217/022Macromolecular 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
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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

An oil-soluble copolymer comprises monomer units of (A) an ethylenic compound which contains a group of from 4 to 30 aliphatic or cycloaliphatic carbon atoms; and (B) an aliphatic alpha, beta-unsaturated carboxylic acid, wherein at leaast a proportion of the carboxyl groups are ester linked to a polypolar alcohol in which at least half and not less than two of the carbon atoms are attached to hydroxy, nitro, mercapto and/or amino polar groups, the copolymer molecule containing from 1 to 20 monomer units for each (B), and not more than 10 units of an ester of the (B) component with a polypolar alcohol, the molecular weight of the copolymer being at least 2000. Compounds of type (A), of which numerous examples are provided, are aliphatic, cycloaliphatic and aromatic mono-olefines, diolefines, vinyl, allyl, propenyl, isopropenyl, methallyl, crotyl, decenyl and eicosenyl ethers, and esters of unsaturated acids and unsaturated alcohols. Compounds of type (B) specified are acrylic, methacrylic, crotonic, tiglic, angelic, alpha-ethylacrylic, alpha-methylcrotonic, alpha-ethylcrotonic, beta-ethylcrotonic, alpha-butylcrotonic, hydrosorbic, maleic, fumaric, citraconic, mesaconic, itaconic and aconitic acids. Polypolar alcohols specified with which the above acids are esterified are ethylene glycol, glycerine, ethanolamine, diethanolamine, triethanolamine, 1,2-propylene glycol, sorbitol, mannitol, glucose, erythritol, pentaerythritol, dipentaerythritol, tripentaerythritol, nitroethanol, mercaptoethanol, 3-mercaptopropanol, 3,5 - dihydroxycyclohexanol, hydroxyethylethylenediamine, N,N1 - dihydroxyethylethylenediamine and 2-aza-propanol. The copolymers may be prepared by (1) copolymerizing the monomer components to produce the desired copolymer, for example by copolymerizing a mixture of dodecyl methacrylate, methacrylic acid and pentaerythritol monomethacrylate, or a mixture of 2-ethylhexyl allyl ether, acrylic acid and 2-hydroxyethyl methacrylate; (2) partially hydrolysing a homopolymer such as polydodecyl methacrylate and then esterifying the resulting carboxyl groups with a polypolar alcohol such as pentaerythritol or ethanolamine; (3) preparing an acid copolymer, for example of maleic anhydride and 2-ethylhexyl acrylate and then esterifying the carboxyl groups thereof with a polypolar alcohol such as pentaerythritol; and (4) preparing an acid copolymer, for example of maleic anhydride and allyl stearate, and first esterifying a proportion of the carboxyl groups with dodecyl alcohol and then esterifying a proportion of the remaining carboxyl groups with a polypolar alcohol such as ethanolamine or dihydroxyethylene diamine. The copolymers, or their polymeric intermediates, may be prepared by bulk, emulsion or, preferably, solution methods, suitable solvents being benzene, toluene, xylene or petroleum naphtha. Polymerization may be assisted by catalysts such as benzoyl peroxide, acetyl peroxide, tert. butyl hydroperoxide, ditert. butyl peroxide, dibenzoyl peroxide, ditert. amyl peroxide, 1,11-azodicyclohexane carbonitrile or alpha,alpha1-azodi-isobutyronitrile. As the polymerization proceeds catalyst can be added in increments and additional portions of solvent can also be added from time to time. The copolymers are used as additives to lubricating oils which may be natural hydrocarbon lubricants or synthetic lubricants such as alkylated wax, hydrogenated polymers of hydrocarbons, condensation products of chlorinated alkyl hydrocarbons with aryl compounds, polymers of propylene and/or ethylene oxides, oils obtained by the etherification and/or esterification of alkylene oxide polymers, e.g. the acetate of the 2-ethylhexanol initiated polymer of propylene oxide, tricresyl phosphate, di-(2-ethylhexyl) sebacate, and silicate esters.ALSO:Lubricating compositions comprise a major proportion of an oil of lubricating viscosity and a minor proportion sufficient to enhance the detergent characteristics of the oil of a copolymer of (A) an organic compound which contains an ethylenic linkage and, in addition, a group of from 4 to 30 aliphatic or cycloaliphatic carbon atoms, and (B) an aliphatic alpha, betaunsaturated carboxylic acid, wherein at least a proportion of the carboxyl groups of the (B) component are ester linked to a polypolar alcohol in which at least half and not less than two of the carbon atoms present therein are attached to hydroxy, nitro, mercapto, and/or amino polar groups, the copolymer molecule containing from 1 to 20 monomer units of the (A) component for each monomer unit of the (B) component, and not more than 10 units of a ester of the (B) component with a polypolar alcohol, the total number of monomer units in each copolymer being such that a molecular weight of at least 2000 is obtained. Compounds of type (A), of which numerous examples are provided are aliphatic, cycloaliphatic and aromatic mono-olefines, diolefines, vinyl allyl, propenyl, isopropenyl, methallyl, crotyl, decenyl and eicosenyl ethers, and esters of unsaturated alcohols and unsaturated acids. Compounds of type (B) specified are acrylic, methacrylic, crotonic, tiglic, angelic, alpha-ethylacrylic, alpha-methylcrotonic, alpha-ethylcrotonic, beta-ethylcrotonic, alpha-butylcrotonic, hydrosorbic, maleic, fumaric atraconic, mesaconic, itaconic, and fumaric acids. Polypolar alcohols specified with which the above acids are esterified are ethylene glycol, glycerine, ethanolamine, diethanolamine, triethanolamine, 1, 2 - propylene glycol, sorbitol, mannitol, glucose, erythritol, pentaerythritol, dipentaerythritol, tripentaerythritol, nitroethanol, mercaptoethanol, 3 - mercaptopropanol, 3, 5 - dihydroxycyclohexanol, hydroxyethylene diamine, N, N1 - dihydroxyethylethylene diamine, and 2 - aza - propanol. The lubricating oils used may be natural hydrocarbon lubricants or synthetic lubricants such as alkylated waxes, hydrogenated polymers of hydrocarbons, condensation products of chlorinated alkyl hydrocarbons with aryl compounds, polymers of propylene and/or ethylene oxides, oils obtained by the etherification and/or esterification of alkylene oxide polymers, e.g. the acetate of the 2-ethylhexanol initiated polymer of propylene oxide, tricresyl phosphate, di(2 - ethylhexyl)sebacate, and silicate esters.
GB27404/53A 1952-10-22 1953-10-06 Lubricant composition Expired GB759918A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1094392B (en) * 1959-08-12 1960-12-08 Roehm & Haas Gmbh Lubricating oil additives
US3033790A (en) * 1958-06-17 1962-05-08 Shell Oil Co Lubricating composition
DE1135604B (en) * 1958-11-18 1962-08-30 Shell Int Research lubricant
DE1248204B (en) * 1958-04-21 1967-08-24 California Research Corp Lubricating oil
EP0471266A1 (en) * 1990-08-11 1992-02-19 Röhm Gmbh Use of oligomers, respectively cooligomers of (meth)acrylates esters and 1-alkenes as synthetic oils
WO2008058108A2 (en) * 2006-11-08 2008-05-15 The Lubrizol Corporation Crosslinked polymer

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248204B (en) * 1958-04-21 1967-08-24 California Research Corp Lubricating oil
US3033790A (en) * 1958-06-17 1962-05-08 Shell Oil Co Lubricating composition
DE1135604B (en) * 1958-11-18 1962-08-30 Shell Int Research lubricant
DE1094392B (en) * 1959-08-12 1960-12-08 Roehm & Haas Gmbh Lubricating oil additives
US3163605A (en) * 1959-08-12 1964-12-29 Roehm & Haas Gmbh Lubricating oil additives
EP0471266A1 (en) * 1990-08-11 1992-02-19 Röhm Gmbh Use of oligomers, respectively cooligomers of (meth)acrylates esters and 1-alkenes as synthetic oils
WO2008058108A2 (en) * 2006-11-08 2008-05-15 The Lubrizol Corporation Crosslinked polymer
WO2008058108A3 (en) * 2006-11-08 2008-10-02 Lubrizol Corp Crosslinked polymer
US8012917B2 (en) 2006-11-08 2011-09-06 The Lubrizol Corporation Crosslinked polymer
CN101548002B (en) * 2006-11-08 2013-04-24 卢布里佐尔公司 Crosslinked polymer

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