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
Authority
GB
United Kingdom
Prior art keywords
vinyl
oil
peroxide
ether
mercepto
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
GB16680/59A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB846856A publication Critical patent/GB846856A/en
Expired legal-status Critical Current

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    • 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
    • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
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    • 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
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—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
    • C08F236/04—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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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers 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
    • C08F36/04—Homopolymers 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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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
    • C10L1/2468—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained by reactions involving only carbon to carbon unsaturated bonds; derivatives thereof
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    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
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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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FR (1) FR1233702A (en)
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US3189547A (en) * 1959-07-03 1965-06-15 Shell Oil Co Lubricating compositions
US3206400A (en) * 1960-10-10 1965-09-14 Shell Oil Co Mineral oil composition
US3310536A (en) * 1962-12-10 1967-03-21 Shell Oil Co Oil soluble polymers
US3322669A (en) * 1965-02-03 1967-05-30 Chevron Res Sulfur substituents of propene/butene copolymers as v.i. improvers
FR2598711B1 (en) * 1986-05-13 1988-09-16 Inst Nat Rech Chimique SULFUR POLYMERIC PRODUCTS WITH MAIN POLYMER SKELETON AND RESIDUES PENDING LINEAR OR BRANCHED CONNECTED TO ONE OR MORE OF THEIR SKELETED AUDIT ENDS, THEIR MANUFACTURING PROCESS AND THEIR APPLICATIONS FOR EXTRACTION AND / OR SEPARATION OF HEAVY METALS
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
US4894410A (en) * 1988-03-09 1990-01-16 Minnesota Mining And Manufacturing Company Fluorine-containing polymers with pendent thioorgano groups
US5225091A (en) * 1988-08-01 1993-07-06 Exxon Chemical Patents Inc. Ethylene alpha-olefin polymer substituted thiocarboxylic acid lubricant dispersant additives
US5205947A (en) * 1988-11-07 1993-04-27 Exxon Chemical Patents Inc. Dispersant additives comprising amine adducts of dicarboxylic acid monoepoxy thiol reaction products
US5057617A (en) * 1988-11-07 1991-10-15 Exxon Chemical Patents Inc. Dispersant additives prepared from monoepoxy thiols
WO1995035331A1 (en) * 1994-07-25 1995-12-28 Wan Jeffrey K S Dithio-containing anti-yellowing agents for pulp and paper
DE19938859A1 (en) * 1999-08-17 2001-02-22 Bayer Ag Functionalized double-bond rubbers

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US2581092A (en) * 1948-01-02 1952-01-01 Standard Oil Dev Co Olefin-diolefin copolymers and mercaptan adducts
GB761897A (en) * 1953-03-30 1956-11-21 California Research Corp Lubricant composition
GB776455A (en) * 1953-10-29 1957-06-05 Exxon Research Engineering Co Additive compositions for lubricating oils and lubricating compositions containing them
NL92381C (en) * 1954-05-10
NL238305A (en) * 1958-04-21

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FR1233702A (en) 1960-10-12
US3041283A (en) 1962-06-26

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