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GB770771A - Copolymeric dispersants and lubricant compositions containing them - Google Patents

Copolymeric dispersants and lubricant compositions containing them

Info

Publication number
GB770771A
GB770771A GB10885/54A GB1088554A GB770771A GB 770771 A GB770771 A GB 770771A GB 10885/54 A GB10885/54 A GB 10885/54A GB 1088554 A GB1088554 A GB 1088554A GB 770771 A GB770771 A GB 770771A
Authority
GB
United Kingdom
Prior art keywords
glycol
methacrylate
dodecyl
ether
oil
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
GB10885/54A
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 GB770771A publication Critical patent/GB770771A/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
    • C10M149/10—Macromolecular compounds obtained 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
    • 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
    • C08F26/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
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    • C10M2201/083—Inorganic acids or salts thereof containing nitrogen nitrites
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2223/042—Metal salts thereof
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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    • 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
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    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • 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
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    • 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
    • C10M2229/02—Unspecified siloxanes; Silicones
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    • 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
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
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    • 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
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    • 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
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    • 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
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

Oil-soluble copolymers consisting of (A) a compound having an olefinic double bond and an oil-solubilizing group of 4 to 30 aliphatic carbon atoms and (B) an alpha, beta-unsaturated carboxylic acid in which from 1 to 10 of the carboxyl groups are ester-linked to a poly-1,2-alkylene oxide glycol and from 1 to 10 of the carboxyl groups are ester linked to an alcohol which, in addition to the hydroxy group through which the ester linkage is formed, is substituted by at least one hydroxyl, mercapto, nitro, or amine radical are made by (1) polymerizing an appropriate monomeric mixture, (2) introducing into a homopolymer of (A) the desired radicals or (3) aftertreating a copolymer of (A) and an alpha, beta-unsaturated carboxylic acid. (A) may be selected from an extensive list including hexene-1, cyclohexene and substituted cyclohexenes, p-octylstyrene, 2-hexadecyl-butadiene-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, betaethyl crotonic, maleic, fumaric, itaconic, glutaconic, citraconic, mesaconic or aconitic. The poly-(1,2-alkylene oxide) glycols 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. The other esterifying compound may be ethylene glycol, ethanolamine, 1,2-propylene glycol, sorbitol, mannitol, glucose, erythritol, pentaerythritol, dipentaerythritol, tripentaerythritol, nitroethanol, mercaptoethanol, 3-mercapto-propanol, 3,5 - dihydroxycyclohexanol, hydroxyethyl ethylenediamine, 2 - aza - propanol, diethanolamine or 2,2,6,6-tetramethylolcyclohexane. The intermediate or final polymers may be prepared by bulk, solution, or emulsion techniques. Preferably, the polymerization is effected in an inert organic solvent such as benzene, toluene or xylene. Suitable catalysts are benzoyl, acetyl, di-tert.-butyl or di-tert.-amyl peroxide, tert.-butyl hydroperoxide, or 1,11-azodicyclohexane-carbonitrile or alpha,alpha1-azodiisobutyronitrile. In examples: (a) maleic anhydride and allyl stearate are copolymerized in toluene in the presence of benzoyl peroxide and the product reacted with dodecyl alcohol and ethanolamine hydrochloride and then with a mixture of polyethylene glycols mainly nonaethylene glycol; (b) the amine in (a) is replaced by dihydroxyethylethylene-diamine hydrochloride; (c) a homopolymer of dodecyl methacrylate is hydrolysed to give a copolymer of dodecyl methacrylate and methacrylic acid, which is esterified with 2-ethyl hexanol, the glycol used in (a) and pentaerythritol; (d) the pentaerythritol in (c) is replaced by tripentaerythritol, and (f) 2-ethylhexyl allyl ether, 3-hydroxypropyl methacrylate and triethylene glycol isobutyl ether methacrylate are polymerized in benzene and toluene. The copolymers are used as additives to lubricating oils.ALSO:A lubricant composition comprises a major proportion of an oil of lubricating viscosity and a minor proportion of an oil-soluble copolymer consisting of (A) a compound which as an olefinic double bond and an oil-solubilizing group of 4 to 30 aliphatic carbon atoms and (B) an alpha, beta-unsaturated carboxylic acid in which from 1 to 10 of the carboxyl groups are ester-linked to a poly-1, 2 alkylene oxide glycol and from 1 to 10 of the carboxyl groups are ester-linked to an alcohol which in addition to the hydroxyl group through which the ester linkage is formed is substituted by at least one hydroxyl, mercapto, nitro, or amine radical (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 a highly refined wax-free base oil, of V.1.85 and derived from California waxy crude is compounded with the following copolymers-allyl stearatedodecyl maleatedodecyl 2-aminoethylmaleate-dodecyl (polyethylene glycol) maleate, allyl searate-dodecyl maleatedodecyl (dihydroxyethyl ethylenediamine) maleate-dodecyl (polyethylene glycol) maleate, dodecyl methacrylate-methacrylic acid-polyethylene glycol methacrylatetripentaerythritol or pantaerythritol monomethacrylate, 2-ethylhexyl allyl ether-3-hydroxypropyl methacrylate-isobutyl ether triethylene glycol methacrylate, and dodecyl methacrylate-polyethylene glycol methacrylate-2-aminoethyl methacrylate.
GB10885/54A 1953-05-18 1954-04-13 Copolymeric dispersants and lubricant compositions containing them Expired GB770771A (en)

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FR (1) FR1111338A (en)
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US3057803A (en) * 1958-04-12 1962-10-09 Roehm & Haas Gmbh Hydraulic fluids with polymeric viscosity index improvers

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US3143513A (en) * 1960-02-26 1964-08-04 Exxon Research Engineering Co Lubricant composition
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US3116248A (en) * 1960-12-23 1963-12-31 Shell Oil Co Lubricating oil composition
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US5349019A (en) * 1988-12-24 1994-09-20 Hoechst New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils
DE3843922A1 (en) * 1988-12-24 1990-06-28 Hoechst Ag NEW COPOLYMERS, THEIR MIXTURES WITH POLY (METH) ACRYLIC ACID ESTERS AND THEIR USE FOR IMPROVING THE FLOWABILITY OF RAW OILS IN THE COLD

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DE747186C (en) * 1942-01-01 1945-01-08 Removable paneling for landing gear struts or the like that can be retracted into the airframe of an aircraft

Cited By (1)

* 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

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