GB768690A - Copolymeric dispersants and lubricant compositions containing them - Google Patents

Copolymeric dispersants and lubricant compositions containing them

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Publication number
GB768690A
GB768690A GB6124/54A GB612454A GB768690A GB 768690 A GB768690 A GB 768690A GB 6124/54 A GB6124/54 A GB 6124/54A GB 612454 A GB612454 A GB 612454A GB 768690 A GB768690 A GB 768690A
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GB
United Kingdom
Prior art keywords
methacrylate
glycol
polyethylene glycol
alpha
monoether
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
GB6124/54A
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
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California Research LLC
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Filing date
Publication date
Application filed by California Research LLC filed Critical California Research LLC
Publication of GB768690A publication Critical patent/GB768690A/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • 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
    • 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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    • 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
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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
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • CCHEMISTRY; METALLURGY
    • 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
    • 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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    • 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
    • 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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    • 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
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106Naphthenic fractions
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108Residual fractions, e.g. bright stocks
    • CCHEMISTRY; METALLURGY
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • CCHEMISTRY; METALLURGY
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2213/00Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
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    • C10M2213/00Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
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    • C10M2213/00Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06Perfluoro polymers
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2217/023Macromolecular 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
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
    • C10M2221/00Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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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
    • C10M2221/00Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043Polyoxyalkylene ethers with a thioether group
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
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    • C10M2227/00Organic 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
    • C10M2227/02Esters of silicic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

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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)
  • Lubricants (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Copolymers of (A) a total of from 75 to 97 mol. per cent of at least one olefinically unsaturated polymerizable compound having an oil-solubilizing group of 4 to 30 aliphatic carbon atoms; (B) at least one lower aliphatic alpha, beta-unsaturated monocarboxylic acid, and (C) at least one ester of a poly-1,2-alkylene glycol and a lower aliphatic alpha, beta-unsaturated monocarboxylic acid are made (1) by polymerizing a mixture of (A), (B) and (C) in the presence of a catalyst; (2) introducing into a homopolymer of (A), units of (B) and (C); or (3) introducing into a copolymer of (A) and (B), units of (C). (A) may be selected from an extensive list including hexene-1, cyclohexene and substituted cyclohexenes, p-octylstyrene, 2-hexadecylbutadiene-1,3, vinyl n-butyl ether, allyl cyclohexyl ether, methallyl n-hexyl ether, vinyl p-octylphenyl ether, 1-decenyl 2-phenylbutyl ether, vinyl caproate, allyl stearate, methallyl palmitate, dodecyl acrylate, cyclohexyl methacrylate, decyl vinyl acetate, p-tert. amylphenyl octadecyl maleate, di-2-ethylhexyl maleate, di-dodecyl mesaconate and citraconate, and 1-hexadecenyl myristate. (B) may be derived from acrylic, methacrylic, crotonic, tiglic, angelic, alpha-ethylacrylic, alpha - methyl crotonic, alpha - ethylcrotonic, beta-ethylcrotonic, alpha-butylcrotonic, hydrosorbic, alpha-ethylhydrosorbic, or alpha-propylhydrosorbic acid. (C) is an ester of an acid as in (B) and a polyglycol such as diethylene glycol, pentaethylene glycol, nonaethylene glycol, tetra - 1,2 - propylene glycol, the monobutyl ether of heptaethylene glycol or a polymer of one or more 1,2-alkylene oxides of molecular weight up to 10,000, in which if desired, at least one of the end groups is replaced by alkoxy or acyloxy groups. The copolymers or polymer intermediates are prepared by conventional methods, e.g. bulk, solution or emulsion, in the presence of catalysts such as benzoyl, acetyl, di-tert. butyl or di-tert. amyl peroxide, tert. butyl hydroperoxide, 1,11-azodicyclohexane-carbonitrile, or alpha, alpha1azodiisobutyronitrile. In examples: (a) a copolymer of dodecyl methacrylate, methacrylic acid and polyethylene glycol monomethacrylate is made by partially hydrolysing a homopolymer of dodecyl methacrylate and reacting with a mixture of polyethylene glycol compounds consisting of a major proportion of nonaethylene glycol of average molecular weight about 400; (b) a copolymer of 2-ethylhexyl allyl ether, acrylic acid and tetra-1,2-propylene glycol acetate acrylate is made by preparing a copolymer of 2-ethylhexyl allyl ether and acrylic acid by reacting the monomers in benzene in the presence of benzoyl peroxide and reacting it with tetra-1,2-propylene glycol monoacetate; (c) a copolymer of 2-ethyl-hexyl acrylate, dodecyl acrylate, methacrylic acid and the monooctyl ether of tridecaethylene glycol is made by reacting a copolymer of 2-ethylhexyl acrylate and methacrylic acid with dodecanol and then with the monooctyl ether of tridecaethylene glycol, and the following copolymers are made by bulk polymerizing the monomers in the presence of benzoyl peroxide, lauryl methacrylate and methacrylic acid and the methacrylate of the lauryl monoether of polyethylene glycol, or the methacrylate of octadecyl monoether of polyethylene glycol, or the methacrylate of the methyl monoether of polyethylene glycol or the methacrylate of polypropylene glycol, tridecyl methacrylate and methacrylic acid and the methacrylate of the tridecyl monoether of polyethylene glycol, octadecyl methacrylate and methacrylic acid and the methacrylate of the lauryl monoether of polyethylene glycol, and (alkylphenoxy)-ethyl methacrylate and methacrylic acid and the methacrylate of the lauryl monoether of polyethylene glycol. The copolymers are used as additives for lubricating oils.ALSO:A lubricant composition comprises a major proportion of an oil of lubricating viscosity and a minor proportion of an oilsoluble copolymer of (a) a total of from 75 to 97 mole per cent of an olefinically unsaturated polymerizable compound having an oil solubilizing group of 4 to 30 aliphatic carbon atoms; (b) at least one monomer unit of a lower aliphatic alpha, beta-unsaturated, monocarboxylic acid, and (c) at least one monomer unit of an ester of a polyoxy-1, 2-alkylene glycol and a lower aliphatic, alpha; beta-unsaturated monocarboxylic acid (see Group IV(a)). The composition may also contain pour-point depressants, oiliness and extreme pressure agents, antioxidants, corrosion inhibiting agents, blooming agents, thickening agents, detergents, anti-wear agents, or compounds for enhancing the temperature-viscosity characteristics of oils. Oils mentioned are refined Pennsylvania or other paraffin base oil, a refined naphthenic base oil, alkylated waxes, hydrogenated hydrocarbon polymers, the condensation products of chlorinated alkyl hydrocarbons with aryl compounds, polymers of propylene and/or ethylene oxide and acetates of these polymers, di-(2-ethylhexyl) sebacate, tricresyl phosphate, silicate esters, or a mixture of a mineral oil and a synthetic oil. In examples the following copolymers are added to a solvent-refined California base oil of viscosity 65 S.S.U. to 110 S.S.U. at 210 DEG F.-lauryl methacrylate and methacrylic acid and the methacrylate of lauryl monoether of polyethylene glycol or the methacrylate of octadecyl monoether of polyethylene glycol, or the methacrylate of methyl monoether of polyethylene glycol or the methacrylate of polypropylene glycol, octadecyl methacrylate/methacrylic acid/and the methacrylate of lauryl monoether of polyethylene glycol, and (alkylphenoxy)-ethyl methacrylate/methacrylic acid/and the methacrylate of lauryl monoether of polyethylene glycol. The function of the copolymer is that of a detergent.
GB6124/54A 1953-03-04 1954-03-02 Copolymeric dispersants and lubricant compositions containing them Expired GB768690A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US768690XA 1953-03-04 1953-03-04

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GB768690A true GB768690A (en) 1957-02-20

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GB6124/54A Expired GB768690A (en) 1953-03-04 1954-03-02 Copolymeric dispersants and lubricant compositions containing them

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057803A (en) * 1958-04-12 1962-10-09 Roehm & Haas Gmbh Hydraulic fluids with polymeric viscosity index improvers
GB2148913A (en) * 1983-08-30 1985-06-05 Ici Plc Water-dilutable coating compositions
EP0542111A2 (en) * 1991-11-13 1993-05-19 Röhm Gmbh Motor oil with high dispensing capacity

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057803A (en) * 1958-04-12 1962-10-09 Roehm & Haas Gmbh Hydraulic fluids with polymeric viscosity index improvers
GB2148913A (en) * 1983-08-30 1985-06-05 Ici Plc Water-dilutable coating compositions
EP0542111A2 (en) * 1991-11-13 1993-05-19 Röhm Gmbh Motor oil with high dispensing capacity
EP0542111A3 (en) * 1991-11-13 1993-06-16 Roehm Gmbh Motor oil with high dispensing capacity

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