GB635903A - Improvements in or relating to high molecular weight copolymers, more especially as lubricating oil additives - Google Patents

Improvements in or relating to high molecular weight copolymers, more especially as lubricating oil additives

Info

Publication number
GB635903A
GB635903A GB31961/46A GB3196146A GB635903A GB 635903 A GB635903 A GB 635903A GB 31961/46 A GB31961/46 A GB 31961/46A GB 3196146 A GB3196146 A GB 3196146A GB 635903 A GB635903 A GB 635903A
Authority
GB
United Kingdom
Prior art keywords
alcohols
oil
wax
vinyl ester
esters
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
GB31961/46A
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.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
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 Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to GB31961/46A priority Critical patent/GB635903A/en
Priority to FR939471D priority patent/FR939471A/en
Publication of GB635903A publication Critical patent/GB635903A/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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • C08F222/00—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
    • C08F222/10—Esters
    • C08F222/12—Esters of phenols or saturated alcohols
    • C08F222/16—Esters having free carboxylic acid groups, e.g. monoalkyl maleates or fumarates
    • C08F222/165—Esters having free carboxylic acid groups, e.g. monoalkyl maleates or fumarates the ester chains containing seven or more carbon atoms
    • 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
    • C10M2203/06—Well-defined aromatic compounds
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular 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
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—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 type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—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 type
    • C10M2209/086—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 type polycarboxylic, e.g. maleic acid
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B47/00—Methods of operating engines involving adding non-fuel substances or anti-knock agents to combustion air, fuel, or fuel-air mixtures of engines

Landscapes

  • 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)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Lubricating oils have their properties such as pour point and viscosity index improved by incorporating a copolymer of a dialkyl fumarate and a vinyl ester of a fatty acid. The alcohol of the fumaric ester is saturated and contains an average of 8-18 carbon atoms, preferably 13.5 as in the product known under the Registered Trade Mark "Lorol." The resulting copolymer is both a pour point depressant and viscosity index improver. Lower alcohols give copolymers which are only viscosity index improvers. The preferred vinyl ester is vinyl acetate (see Group IV (a)). They may be used in concentrations of up to 10 per cent of the oil, examples of which are paraffinic oils including diesel fuel and domestic heating oil base stocks, mineral seal oil and refined kerosene. The copolymers may also be added to greases containing metal soaps or to paraffin wax compositions. Other additives may also be added and include dyes, anti-oxidants, wax-phenol or wax-naphthalene condensation products, polybutene, polyacrylates, polyvinyl ethers and esters.ALSO:A dialkyl fumarate of one or more saturated alcohols having an average of 8 to 18 carbon atoms in the molecule is heated with a vinyl ester of a fatty acid in the presence of an oxygen yielding catalyst to yield a copolymer suitable as a lubricant additive. Suitable alcohols of the fumaric ester are the product obtained by hydrogenating coconut oil, octyl, decyl, octadecyl and cetyl alcohols and minor amounts of lower alcohols, e.g. hexyl and amyl alcohols. Suitable vinyl esters are those of acetic, propionic, butyric, lauric, myristic and palmitic acids, including the vinyl ester of coconut oil acids. Polymerization may be effected at 50-125 DEG C. in an inert atmosphere using super-atmospheric pressure or refluxing. Diluents such as petroleum ether, refined naphtha, kerosene or lubricating oil may be employed. Suitable catalysts are peroxides, e.g. benzoyl, acetyl and tert.-butyl hydroperoxide and tert.-butyl perbenzoate. The products may be used in concentrations of up to 10 per cent in paraffinic, naphthenic and mixed base oils, in greases containing metal soaps, paraffin wax compositions, refined kerosene, and mineral seal oil. Other ingredients which may be added include dyes, anti-oxidants, other lubricant additives, e.g. wax-naphthalene or waxphenol condensation products, polybutene, polyacrylates, polyvinyl ethers and esters.
GB31961/46A 1946-10-28 1946-10-28 Improvements in or relating to high molecular weight copolymers, more especially as lubricating oil additives Expired GB635903A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB31961/46A GB635903A (en) 1946-10-28 1946-10-28 Improvements in or relating to high molecular weight copolymers, more especially as lubricating oil additives
FR939471D FR939471A (en) 1946-10-28 1947-01-02 High molecular weight copolymers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31961/46A GB635903A (en) 1946-10-28 1946-10-28 Improvements in or relating to high molecular weight copolymers, more especially as lubricating oil additives

Publications (1)

Publication Number Publication Date
GB635903A true GB635903A (en) 1950-04-19

Family

ID=10330957

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31961/46A Expired GB635903A (en) 1946-10-28 1946-10-28 Improvements in or relating to high molecular weight copolymers, more especially as lubricating oil additives

Country Status (2)

Country Link
FR (1) FR939471A (en)
GB (1) GB635903A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721878A (en) * 1951-08-18 1955-10-25 Exxon Research Engineering Co Strong acid as a polymerization modifier in the production of liquid polymers
DE1031918B (en) * 1955-11-16 1958-06-12 Exxon Research Engineering Co Mineral oil-based lubricating oil containing a copolymer of a vinyl ester with a fumaric acid dialkyl ester mixture
DE1037631B (en) * 1955-12-07 1958-08-28 Exxon Research Engineering Co Lubricating oil mixture
DE1248201B (en) * 1960-10-24 1967-08-24 Exxon Research Engineering Co Process for dewaxing mineral oils
EP2071013B1 (en) * 2007-12-03 2017-11-08 Infineum International Limited Lubricant composition comprising a flow improver having a bi-modal side-chain distribution

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721878A (en) * 1951-08-18 1955-10-25 Exxon Research Engineering Co Strong acid as a polymerization modifier in the production of liquid polymers
DE1031918B (en) * 1955-11-16 1958-06-12 Exxon Research Engineering Co Mineral oil-based lubricating oil containing a copolymer of a vinyl ester with a fumaric acid dialkyl ester mixture
DE1037631B (en) * 1955-12-07 1958-08-28 Exxon Research Engineering Co Lubricating oil mixture
DE1248201B (en) * 1960-10-24 1967-08-24 Exxon Research Engineering Co Process for dewaxing mineral oils
EP2071013B1 (en) * 2007-12-03 2017-11-08 Infineum International Limited Lubricant composition comprising a flow improver having a bi-modal side-chain distribution

Also Published As

Publication number Publication date
FR939471A (en) 1948-11-16

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