GB846856A - Novel polymeric compounds - Google Patents

Novel polymeric compounds

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Publication number
GB846856A
GB846856A GB16680/59A GB1668059A GB846856A GB 846856 A GB846856 A GB 846856A GB 16680/59 A GB16680/59 A GB 16680/59A GB 1668059 A GB1668059 A GB 1668059A GB 846856 A GB846856 A GB 846856A
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United Kingdom
Prior art keywords
vinyl
oil
peroxide
ether
mercepto
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Expired
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GB16680/59A
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Bataafsche Petroleum Maatschappij NV
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Bataafsche Petroleum Maatschappij NV
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Publication of GB846856A publication Critical patent/GB846856A/en
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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
    • C10M151/00Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F236/00Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
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    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
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    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/24Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2462Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
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    • C10M3/00Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2800/00Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/10Copolymer characterised by the proportions of the comonomers expressed as molar percentages
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    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06Well-defined aromatic compounds
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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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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/283Esters of polyhydroxy compounds
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/286Esters of polymerised unsaturated acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
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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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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M2229/00Organic 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
    • C10M2229/02Unspecified siloxanes; Silicones
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    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
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    • C10N2040/08Hydraulic fluids, e.g. brake-fluids
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

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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)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

A polymeric compound which may be used as a lubricating oil additive (see Group III) consists of a linear hydrocarbon back-bone chain, a plurality of oil-solubilizing hydrocarbyl radicals having at least 8 carbon atoms, and a plurality of -S-(CH2)n-X radicals, wherein n is an integer of 1 to 4 and X stands for a polar substituant, each radical being attached directly or indirectly to a different carbon atom of the back-bone chain, The hydrocarbon radicals may be indirectly attached to the back-bone chain by a carboxy or amide radical. The polymeric compound may be produced by reacting a mercepto compound of the formula H-S(CH2)n-X with an oil soluble unsaturated polymeric compound. The mercepto compound may be mercepto acetic acid, mercepto propionic acid, mercepto butyric acid, ethyl merceptoectate, ethyl merceptobutylate, 2-merceptoethanol, 2 and 3 merceptoproponol, 2-, 3-, and 4-mercaptobutanol methyl or ethyl 2-mercaptoethyl ether, mercaptoethylamine, mercaptobutylamine, (mercaptoethyl) diethyl amine. The oil soluble unsaturated polymeric compound may be prepared by copolymerizing a polyene hydrocarbon with a monoethylenically unsaturated monomer having at least 10 carbon atoms The polyene hydrocarbons may be 1,3- and 1,4-pentadiene, isoprene, 1,3-hexadiene, 1,3,5-heptortriene, 1,3-cyclopentadiene, methyl cyclopentadiene, 1,3- and 1,4-cyclohexadiene, and methylcyclohexadiene. The monoethylenically unsaturated monomers may be decene-1, dodecene-1, tridecene-1, tetradecene-1, hexodecene-1, heptodecene-1, octadecene-1, tritriacontene-1, tetratriacontene-1, heptacontene-1, 4-methyl-decene-1, 4,4,-dimethyl-decene-1, 5,5-dimethylhexene-1, 5,5,7,7,-tetramethyldecene-1,4,4,6,6,-tetramethylheptene-1, vinyl decanoate, vinyl laurate, vinyl tridecanoate, vinyl myristate, vinyl pentadecanoate, vinyl palmitate, vinyl margarate, vinyl stearate, vinyl nonadecanoate, vinyl arachidate, vinyl behenate, vinyl 4,5,6,-trimethyldodecanoate, vinyl 6,8,9,-triethyl tridecanoate, vinyl-12-hydroxystearate, vinyl 9,10,-dihydroxystearate, vinyl chlorostearate, vinyl cyanostearate, vinyl acetyl stearate, allyl stearate, vinyl dodicyl ether, vinyl tridecyl ether, vinyl tetracosyl ether, vinyl hexacosyl ether, allyl dodecyl ether, N-lauryl methacrylamide, N-stearate methacrylamide, N,N-distearyl methacrylamide. The copolymers may be made in the presence of a catalyst such as a Ziegler catalyst, diethyl peroxide, tertiary butyl hydroperoxide, dibenzoyl peroxide, dimethylthienyl peroxide, dicyclohexyl peroxide, dilauroyl peroxide, urea peroxide, sodium bisulphite, diethyl sulphoxide, ammonium persulphate, alkali metal perborates, alpha, alpha-azodiisobutyronitrile. The final sulphur containing polymer may be obtained by using as catalyst or initiator, ultraviolet light tert-butyl peroxide, alpha, alpha-azodiisobutyronitrile or emulsion redox systems for example a mixture of sodium bisulphite, and persulphate ammonium persulphate, and alkali metal perborates.ALSO:Lubricating oils comprise a minor proportion of a polymeric compound which may be prepared according to the method set out in Group IV(a) consisting of a linear hydrocarbon backbone chain, a plurality of oilsolubilizing hydrocarbyl radicals having at least 8 carbon atoms and a plurality of -S-(CH2)n-X radicals, wherein n is an integer of 1 to 4 and X stands for a polar substituent, each radical being attached directly or indirectly to a different carbon atom of the backbone chain. The lubricating oil base may be a mineral oil or a synthetic oil such as a polymerized olefine, alkylated aromatic, isomerised wax or a copolymer of alkylene glycol and alkylene oxide as described in U.S.A. Specifications 2,425,755, 2,425,845 and 2,775,733, or di-2-ethyl hexyl sebacate or di-2-ethyl hexyl adipate esters of polyhydric alcohols and monocarboxylic acids such as pentacrythritol tetracaproate. The hydrocarbon oils may be blended with castor oil, lard oil or silicone polymers. In a typical example, 1-octadecene, 1 dodecene and isoprene were copolymerized in the presence of Ziegler catalyst and the resulting copolymer reacted with mercaptoacetic acid. 2% of this product was added to a mineral oil.
GB16680/59A 1958-05-19 1959-05-15 Novel polymeric compounds Expired GB846856A (en)

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ES2003864A4 (en) * 1986-12-24 1988-12-01 Monsanto Co RESIN SUPPORT FOR THE SYNTHESIS OF PEPTIDES IN SOLID PHASE.
FR2614312B1 (en) * 1987-04-24 1990-03-09 Elf Aquitaine WATER SOLUBLE ADDITIVES WITH EXTREME PRESSURE EFFECT FOR AQUEOUS FUNCTIONAL FLUIDS, FUNCTIONAL FLUIDS AND CONCENTRATED AQUEOUS COMPOSITIONS CONTAINING SAID ADDITIVES.
GB8711191D0 (en) * 1987-05-12 1987-06-17 Bp Chemicals Additives Lubricating oil additives
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DE19938859A1 (en) * 1999-08-17 2001-02-22 Bayer Ag Functionalized double-bond rubbers

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GB776455A (en) * 1953-10-29 1957-06-05 Exxon Research Engineering Co Additive compositions for lubricating oils and lubricating compositions containing them
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NL238305A (en) * 1958-04-21

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US3041283A (en) 1962-06-26

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