GB768701A - Copolymeric dispersants and lubricant compositions containing them - Google Patents

Copolymeric dispersants and lubricant compositions containing them

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Publication number
GB768701A
GB768701A GB15455/54A GB1545554A GB768701A GB 768701 A GB768701 A GB 768701A GB 15455/54 A GB15455/54 A GB 15455/54A GB 1545554 A GB1545554 A GB 1545554A GB 768701 A GB768701 A GB 768701A
Authority
GB
United Kingdom
Prior art keywords
copolymer
methacrylate
acid
ether
glycol
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
GB15455/54A
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
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
Application filed by California Research LLC filed Critical California Research LLC
Publication of GB768701A publication Critical patent/GB768701A/en
Expired legal-status Critical Current

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    • 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
    • C10M149/06—Macromolecular compounds obtained 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
    • 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
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • 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
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    • C10M145/12—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 monocarboxylic
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    • C10M145/10—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
    • C10M145/16—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 polycarboxylic
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    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
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    • 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
    • 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
    • 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
    • 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

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  • 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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubricants (AREA)

Abstract

Copolymers of (A) an olefinically-unsaturated compound preferably containing an oil-solubilizing group of from 4 to 30 aliphatic carbon atoms, and (B) an alpha-beta-unsaturated carboxylic acid, in which some of the carboxyl groups are ester-linked to a poly-(1,2-alkylene oxide) glycol, and some are linked to a nitrogen-containing compound to form either of the radicals <FORM:0768701/IV(a)/1> and <FORM:0768701/IV(a)/2> where R1 is hydrogen or an organic radical and R2 an organic radical are made (1) by partially hydrolysing a homopolymer of an ester of an unsaturated acid and reacting the free carboxyl groups with the desired polyglycol and nitrogen-containing compound; (2) partially esterifying a copolymer of an olefinically-unsaturated monomer of an alpha, beta-unsaturated acid or anhydride with a polyglycol and nitrogen-containing compound; or (3) polymerizing an appropriate monomer mixture. (A) may be selected from an extensive list including ethylene, 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. The alpha, beta-unsaturated acid may be acrylic, methacrylic, crotonic, tiglic, angelic, alpha-ethylacrylic, beta-ethyl crotonic, maleic, fumaric, itaconic, glutaconic, citraconic, mesaconic or aconitic. The poly-(1,2-alkylene oxide) glycol may be 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. In the case of the nitrogen containing compound the organic radical may be methyl to heptadecyl, phenyl, tolyl, xylyl, benzyl, naphthyl, 2-hydroxyethyl, 4 - hydroxycyclohexyl, 3 - azapentyl, 4-amonohexyl, 2-mercaptoethyl, 3-aza-5 - hydroxypentyl, 2 - ethyl - 6 - aminohexyl, 2-nitrohexyl, p-aminophenyl, or 2-hydroxy-6-phenylhexyl. An extensive list of monomeric nitrogen-containing compounds is given including methacrylamide, N - ethylmethacrylamide, N-phenyl methacrylamide, N,N-di-(2-hydroxyethyl)-methacrylamide, the ethylamine or ethanolamine salt of methacrylic acid, acrylamide, N,N - di - (2 - ethylhexyl) - acrylamide, crotonamide, N - (2 - nitroethyl)-crotonamide, tiglamide, maleamic acid, maleamide, N,N1 - diethylmaleamide, N - phenylmaleamic acid, lauryl N-(2-hydroxyethyl)-malemate, tetraethylene pentamine salt of lauryl maleate, N,N1 - di - (2 - mercaptoethyl)-maleamide, dodecyl N-(p-aminophenyl)-malemate, fumaramic acid, erythritol monofumaramate, dodecyl N - (2 - hydroxyethyl) - citraconamate. The copolymers may be prepared by bulk, solution or emulsion techniques in the presence of a catalyst. The copolymerization is preferably effected in an inert solvent such as benzene, toluene, xylene, or petroleum naphtha. Catalysts mentioned are benzoyl, acetyl, di-tert. butyl, and di-tert. amyl peroxides, 1,11-azodicyclohexanecarbonitrile, and alpha, alpha1 - azodiisobutyronitrile. In examples: (a) a copolymer of dodecyl methacrylate, polyethylene glycol methacrylate, N-octyl-methacrylamide and methacrylic acid is made by partially hydrolysing a homopolymer of dodecyl methacrylate and reacting with a mixture of polyethylene glycols which includes a major proportion of nonaethylene glycol and then with n-octylamine; (b) a copolymer of dodecyl methacrylate, polyethylene glycol monoether methacrylate and N - (2 - hydroxyethyl) - methacrylamide is similarly made; (c) a copolymer of vinyl 2-ethyl hexyl ether, acrylic acid, methacrylamide, and polypropylene glycol acrylate is made by copolymerizing the ether, acid, and amide in bulk, and esterifying the product with 2-propylene glycol; (d) a copolymer of dodecyl methacrylate, the methacrylate of a polyglycol mono-octyl ether and maleic anhydride is reacted first with pentaerythritol and then with isooctadecylamine; (e) a copolymer of tridecyl acrylate, the methacrylate of polyethylene glycol monoethyl ether and methacrylic acid is treated with p-nitroaniline; (f) the copolymer of (e) is reacted first with glycerol and then with n-octylamine.ALSO:A lubricant composition comprises a major proportion of an oil of lubricating viscosity and a minor proportion of an oil-soluble copolymer (see Group IV(a)) of (A) an olelinically-unsaturated compound, and (B) an alpha, betaunsaturated carboxylic acid, in which a portion of the carboxylic groups of the acid are ester-linked to a poly-(1, 2-alkylene oxide) glycol and another portion of the carboxyl groups are linked to a nitrogen-containing compound to form radicals selected from <FORM:0768701/III/1> or <FORM:0768701/III/2> where R1 is hydrogen or an organic radical and R2 an organic radical. The compositions 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. Polymers exemplified in oil compositions are (1) a copolymer of dodecyl methacrylate/polyethylene glycol methacrylate/N - octyl - methacrylamide (2) a copolymer of dodecyl methacrylate/polyethylene glycol monoether methacrylate/N - (2 - hydroxyethyl) methacrylamide, (3) a copolymer of vinyl 2 - ethyl-hexyl ether/methacrylamide/acrylic acid/polypropylene glycol acrylate (4) a copolymer of dodecyl methacrylate/polyglycol ether methacrylate/pentaerythritol maleate/maleic acid amine salt (5) a copolymer of allyl stearate/di - tridecyl maleate-mono - tridecyl polyglycol maleate/ethanolamine salt of mono-tridecyl maleate-monotridecyl maleate, (6) a copolymer of tridecyl acrylate-polyethylene glycol ether methacrylate/N - (p - nitrophenyl) methacrylamide-methacrylic acid, and (7) a copolymer of tridecyl acrylate/polyethylene glycol ether methacrylate/glycerol monomethacrylate/octyl amine salt of methacrylic acid. The function of the copolymer in the oil is that of a detergent.
GB15455/54A 1953-06-10 1954-05-25 Copolymeric dispersants and lubricant compositions containing them Expired GB768701A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US768701XA 1953-06-10 1953-06-10

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GB768701A true GB768701A (en) 1957-02-20

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GB15455/54A Expired GB768701A (en) 1953-06-10 1954-05-25 Copolymeric dispersants and lubricant compositions containing them

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FR (1) FR1150894A (en)
GB (1) GB768701A (en)
NL (2) NL206960A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2892793A (en) * 1957-09-19 1959-06-30 California Research Corp Lubricant composition
WO2006015130A1 (en) * 2004-07-30 2006-02-09 The Lubrizol Corporation Dispersant viscosity modifiers containing aromatic amines
WO2010099136A1 (en) 2009-02-26 2010-09-02 The Lubrizol Corporation Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant
US8557753B2 (en) 2008-11-26 2013-10-15 The Lubrizol Corporation Lubricating composition containing a functionalized carboxylic polymer
US8637437B2 (en) 2007-11-13 2014-01-28 The Lubrizol Corporation Lubricating composition containing a polymer
US8912133B2 (en) 2007-11-13 2014-12-16 The Lubrizol Corporation Lubricating composition containing a polymer

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL238305A (en) * 1958-04-21
GB922878A (en) * 1958-06-26 1963-04-03 Monsanto Chemicals Oil-soluble copolymeric materials and compositions containing the same
DE1094392B (en) * 1959-08-12 1960-12-08 Roehm & Haas Gmbh Lubricating oil additives

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2892793A (en) * 1957-09-19 1959-06-30 California Research Corp Lubricant composition
WO2006015130A1 (en) * 2004-07-30 2006-02-09 The Lubrizol Corporation Dispersant viscosity modifiers containing aromatic amines
US7790661B2 (en) 2004-07-30 2010-09-07 The Lubrizol Corporation Dispersant viscosity modifiers containing aromatic amines
CN101031633B (en) * 2004-07-30 2010-11-10 卢布里佐尔公司 Method for lubricating diesel engine installed with waste gas recirculation device
US7960320B2 (en) 2004-07-30 2011-06-14 The Lubrizol Corporation Dispersant viscosity modifiers containing aromatic amines
US8637437B2 (en) 2007-11-13 2014-01-28 The Lubrizol Corporation Lubricating composition containing a polymer
US8912133B2 (en) 2007-11-13 2014-12-16 The Lubrizol Corporation Lubricating composition containing a polymer
US8557753B2 (en) 2008-11-26 2013-10-15 The Lubrizol Corporation Lubricating composition containing a functionalized carboxylic polymer
WO2010099136A1 (en) 2009-02-26 2010-09-02 The Lubrizol Corporation Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant
EP2431448A1 (en) 2009-02-26 2012-03-21 The Lubrizol Corporation Lubricating compositions containing the reaction product of an aromatic amine and a carboxylic functionalised polymer and dispersant
US8569217B2 (en) 2009-02-26 2013-10-29 The Lubrizol Corporation Lubricating composition containing a carboxylic functionalised polymer and dispersant
US9644167B2 (en) 2009-02-26 2017-05-09 The Lubrizol Corporation Lubricating compositions containing a carboxylic functionalised polymer and dispersant

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FR1150894A (en) 1958-01-21
NL105836C (en)

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