US3030303A - Lubricating oil composition - Google Patents

Lubricating oil composition Download PDF

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Publication number
US3030303A
US3030303A US651598A US65159857A US3030303A US 3030303 A US3030303 A US 3030303A US 651598 A US651598 A US 651598A US 65159857 A US65159857 A US 65159857A US 3030303 A US3030303 A US 3030303A
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United States
Prior art keywords
lubricating oil
vinyl
copolymer
dithiocarbamate
methacrylate
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 - Lifetime
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US651598A
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English (en)
Inventor
Julian G Ryan
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.)
Shell USA Inc
Original Assignee
Shell Oil Co
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Filing date
Publication date
Priority to NL105971D priority Critical patent/NL105971C/xx
Priority to NL226646D priority patent/NL226646A/xx
Priority to BE566592D priority patent/BE566592A/xx
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US651598A priority patent/US3030303A/en
Priority to GB11043/58A priority patent/GB836303A/en
Priority to DEN14912A priority patent/DE1063312B/de
Priority to FR1206669D priority patent/FR1206669A/fr
Application granted granted Critical
Publication of US3030303A publication Critical patent/US3030303A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/08—Anhydrides
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • 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
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2215/26—Amines
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    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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    • C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
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    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/046—Overbasedsulfonic acid salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
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    • C10M2219/068—Thiocarbamate metal salts
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines

Definitions

  • This invention relates to lubricating oil compositions, and more particularly to highly detergent lubricating oil compositions which also possess good load carrying and high temperature stability properties.
  • the oil-soluble nitrogen-containing polymeric detergents are characterized in that they are essentially straight chain aliphatic hydrocarbon polymers having attached indirectly, through an oxygen-containing polar group, to the main hydrocarbon chain, a plurality of the same or different oleophilic alkyl radicals having at least 8 carbon atoms, and attached to different carbons of the main hydrocarbon chain a plurality of radicals containing nitrogen, preferably such that the oleophilic alkyl radicals are predominant to the nitrogen-contaim'ng radicals.
  • the polymerizable monomer reactants are used in the mol ratio of from 1:10 to 10:1 and preferably from 1:1 to 1:7 of the nitrogen-containing polymerizable compound to the polymerizable material containing an oleophilic radical, respectively.
  • the polymeric detergents range in molecular weight from 50,000 to over 2 million as determined by the light scattering method.
  • the detergent polymers are derived from at least two different polymerizable compounds, one of which contains an oleophilic alkyl radical of from 8 to 22 carbon atoms which is not part of the main hydrocarbon chain, and at least one polymerizable ntirogen-containing compound.
  • the polymers may be derived from different polymerizable compounds as above and optionally also from one or more additional polymerizable compounds which can be analogous of the above polymerizable compounds or be of entirely diflerent classes.
  • Polymerizable monomers containing oleophilic components containing an aliphatic hydrocarbon chain of at least 8 carbon atoms which is not part of the main hydrocarbon polymer chain include polymerizable esters, ethers, acids, and mixtures thereof.
  • Suitable esters include acrylic acid (including esters of acrylic acid and of alphaalkyl-substituted acrylic acid, preferably of from 3 to 4 carbon atoms) and aliphatic alcohols of at least 8 carbon atoms and preferably of from 12 to 20 carbon atoms such as decyl acrylate, lauryl acrylate, stearyl acrylate, eicosanyl acrylate, docosanyl acrylate, decyl methacrylate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, and the like and mixtures thereof.
  • esters include the vinl esters of long-chain carboxylic acids such as vinyl laurate, vinyl palmitate, vinyl stearate, vinyl oleate and the like and mixtures thereof; long-chain esters of vinylene dicarboxylic acids such as methyl lauryl fumarate and the like.
  • the technical lauryl methacrylate obtained from the commercial mixture of long-chain alcohols in the C to C range derived from coconut oil is an especially useful oleophilic component of the copolymer but the group of acrylic and alkacrylic esters of aliphatic alcohols of at least eight carbons are, in general, well suited as the oleophilic component of the copolymer.
  • the nitrogen-containing component of the polymers can be introduced through the use of appropriate copolymerizable monomers containing primary, secondary or tertiary amino. nitrogen or nitrogen-containing heterocycles which are attached ultimately to the chain of the polymer as part of the extra substituent group.
  • nitrogen-containing monomers include the amino substituted olefins such as p-(bet-adiethylaminoethyl)styrene; basic nitrogen-containing heterocycles carrying a polymerizable ethylenically unsaturated substituent, e.g.
  • the vinyl pridines and the vinl alkyl pyridines such as 2-vinyl-5-ethyl pyridine; 2-methyl-5- vinyl pyridine, 2-vinyl-pyridine, 3-vinylpyridine, 4-vinylpyridine, 3-rnethyl-5-vinylpyridine, 4-methyl-2-vinylpyridine, 4-ethyl-2-vinylpyridine and Z-butyl-S-vinylpyridine and the like.
  • N-vinyl lactams are also suitable, and particularly when they are N-vinyl pyrrolidones or N-vinyl piperidones.
  • the vinyl pyrrolidones are the preferred class of N -vinyl lactams and are exemplified by N-vinyl pyrrolidone, N-( l-methylvinyl) pyrrolidone, N-vinyl-S-methyl pyrrolidone, N-vinyl-3,3-dimethyl pyrrolidone, N-vinyl-S-ethyl pyrrolidone, N-vinyl-4-butyl pyrrolidone N-ethyl-3-vinyl pyrrolidone, N-butyl-S-vinyl pyrrolidone, 3-vinyl pyrrolias the alkyl and cycloalkyl substituted aminoalkyl and cycloalkyl substituted aminoalkyl and cycloalkyl esters of the acrylic and alkacrylic acids, e.g.
  • beta-methylaminoethyl acrylate 4-diethyl-aminocyclohexyl methacrylate, beta, beta-didodecylaminoethyl acrylate, and the like; unsaturated ethers of amino alcohols such as the vinyl ethers of such alcohols, 'e.g. beta-aminoethyl vinyl ether, beta-diethylaminoethyl vinyl ether, and the like; amides of unsaturated carboxylic acids wherein an amino substituent is carried on the amide nitrogen such as N(betadimethylaminoethyl) acrylamide; polymerizable unsaturated amines, e.g. diallylamine, and they like.
  • unsaturated ethers of amino alcohols such as the vinyl ethers of such alcohols, 'e.g. beta-aminoethyl vinyl ether, beta-diethylaminoethyl vinyl ether, and the like
  • These detergent polymers may contain variable but substantial amount of from about 5 to 30% based on the final product of other polymerizable components such as vinyl and allyl formates, acetates, propionate's, butyrates, and the like; polymerizable unsaturated'short-chain hydrocarbons, e,g. the. monoolefins such. as ethylene, propylene, isobutylene, styrene, vinyltoluene, and the like and the short-chain'dienes such as. '1,3'-buta'diene, isoprene, and the like; unsaturated short-chain carboxylic acids and their derivatives such as the alpha-methylene-carboxylic acids and their derivatives, e.g.
  • acrylic acid methyl methacrylate, butyl methacrylate, acrylonitrile, methacrylamide, and the like
  • short-chain unsaturated ethers particularly the vinyl and allyl ethers, e.g. ethyl vinyl ether, butyl vinyl ether, and the like.
  • the polymers can be prepared by any suitable means such as described in US. patent application Serial No. 571,612, filed March 15, 1956, and U.S. Patent 2,737,452.
  • EXAMPLE III A mixture of about 6 moles of lauryl methacrylate, 1 mole of N-vinyl pyrrolidone and 0.5% by weight of benzoyl peroxide was reacted in a suitable reaction vessel for a period of about 10 hours at about 65 C. The polymer was then dispersed in benzene and thereafter precipitatedwith a mixture of acetone and methanol. This was repeated and a copolymer of lauryl methacrylate/N- vinyl pyrrolidone having a nitrogen content of 0.45% by weight and a molecular weight in excess of 250,000 was recovered. The polymer contained the monomer units in the ratio as provided in the mixture.
  • EXAMPLE IV- A mixture of i020 parts of technical lauryl methacry- VII late, parts of methacrylanilide, 60 parts of beta-diethylaminoethyl methacrylate, 300 parts of mineral oil and 3.6 parts of alpha, alpha'-azodiisobutyronitrile was agitated together at 60i2 C. under nitrogen. After two hours some thickening of the charge was observed and during the next 16 hours, 900 parts more of mineral oil was added gradually as the polymerization proceeded. There was thus obtained a barely stirrable oil solution of a copolymer of the three polymerizable components in essentially the mole proportions charged, i.e. 86.4/ 8.5/5.1.
  • the technical lauryl methacrylate used in the preparation above is the methacrylic acid ester of technical lauryl alcohol which is obtained by reduction of the fatty acids of coconutoil and is a mixture of saturated straight chain alcohols ranging from about 10 to 18 carbon atoms.
  • a typical example will contain approximately 3%.C 61% C12, CH' C15 C18 alcohols.
  • the mineral lubricating oils used in compositions of this invention can be obtained from any parafiinic, naphthenic,.asphaltic or mixed base crude, and/or mixtures thereof.
  • the viscosity of these oils may vary over a wide range, such as from 100 SUS at 100 F. to 100 SUS at 210 F.
  • Mineral lubricating oils which are particularly desirable for use in compositions of the invention can be obtained from West Texas Ellenburger crudes, East Texas crudes, Oklahoma crudes, California crudes.
  • a useful solvent refined East Texas mineral lubricating oil had the following properties Pour point, F
  • Viscosity centistokes at 100 Fa.. Viscosity index
  • the additive combination is effective in lubricating oil compositions in amounts ranging from about 0.1% to about and preferably from about 0.5% to 6% by weight each, based on the final lubricating oil composition.
  • compositions of this invention are illustrated by the following:
  • COMPOSITION E Terpolymer of Example VII 5.5% wt. Zn diamyl dithiocarbamatc 0.5% wt. Zn dimethylcyclohexyl thiophosphate 0.92% wt. Basic Ca petroleum sulfonate 1.0% SA. Mineral lubricating oil Balance.
  • COMPOSITION F Copolymer of Example I 5.5% wt. Zn diamyl dithiocarbamate 0.4% wt. Zn dimethylcyclohexyl thiophosphate 0.92% wt. Basic Ca petroleum sulfonatc 1.0% SA. Mineral lubricating oil Balance.
  • compositions of this invention are shown in Table II when they were tested in the Timken machine for load carrying properties and in the Cadillac engine under heavy duty highway-cycle test and in the COT engine 80-hour high-temperature test for cleanliness, corrosion and overall engine conditions.
  • COT ENGINE (CRC SINGLE CYLINDER ENGINE) R.p m 2800 Jacket temp F-.. 375' Oil temp F 275 Carburetor air temp F 110 Time hours 80 Table 11 Chrysler Test 1 COT Tim- Eng. Composition ken Intake Test Load, Sludge Overall Valve Bearlbs. Rating Rating Deposmg wt it loss Ratin D (present invention) 28 91 85 E (present invention) 28 95 90 80 Composition X 2 16 60 78 68 A (present invention) 30 267 Mineral lubricating oil 10 50 50 60 l, 157
  • composition X is same as composition D except it contained no Zinc diamyl dithiocarbamate.
  • compositions B, C, E and F when tested in the Timken machine and in the Cadillac engine gave results similar to composition D. Also compositions B, C, D, E and F when tested in the COT engine efiectively inhibited corrosion and the engine was clean and in good condition. On the other hand when the zinc dialkyldithiocarbamate was omitted from these compositions and tested as described above load carrying properties were poor (about same as for composition X) and the engines were in poor condition at the end of these tests.
  • the additive combination of this invention is useful for providing superior detergent and wear inhibiting properties to lubricating oils which contain small amounts (0.1% to 3%) of other agents such as metal dithiophosphates (Zn alkyl dithiophosphate) metal organic sulfonates, e.g. neutral or basic Ca, Ba or Zn petroleum sulfonate, amines such as phenyl-alpha-naphthylamine, octadecylamine, alkyl phenol, viscosity-index improvers and pour point depressants such as the Acryloids, and specifically, Acryloid, 150, 618, 710, and/or 768, made by Rohm and Haas and described in US.
  • Zn alkyl dithiophosphate metal organic sulfonates
  • amines such as phenyl-alpha-naphthylamine, octadecylamine, alkyl phenol
  • Patent 2,710,842 condensation products of chlorinated parafiin wax and naphthalene; extreme pressure agents such as amine salts of trichloromethane phosphinic acid, its ester, amides or amine salts; organic sulfides and mixtures thereof.
  • compositions of this invention are used as engine oils, turbine oils, gear oils, and in various other fields of lubrication Where detergency and wear inhibiting properties are essential.
  • a lubricating oil composition consisting essentially of a major amount of mineral lubricating oil and from about 0.1% to about 10% of an oil-soluble copolymer selected from the group consisting of (1) a copolymer of a C alkyl methacrylate and a vinylpyridine in the mol ratio of 1:1 to 7:1, respectively, and (2) a C1240 alkyl methacrylate and a vinylpyrrolidone in the mol ratio of 1:1 to 7:1, respectively, the copolymer having a molecular weight of from 50,000 to 2,000,000 and a minor but load carrying and stabilizing amount of an oilsoluble divalent metal salt of a dialkyl dithiocarbamic acid, the divalent metal being selected from the group consisting of Zinc and cadmium.
  • an oil-soluble copolymer selected from the group consisting of (1) a copolymer of a C alkyl methacrylate and a vinylpyridine in the mol ratio of 1:1 to 7:1, respectively, and (2) a C1240 al
  • a lubricating oil composition consisting essentially of a major amount of a mineral lubricating oil and from about 0.5 to about 6% of an oil-soluble copolymer of a C1240 alkyl methacrylate and vinylpyrrolidone in the mol ratio of 1:1 to 7:1, respectively, and having amolecular weight of from 50,000 to 2,000,000 and a minor, but loadcarrying amount, of an oil-soluble zinc dialkyl dithiocarbamate.
  • a lubricating composition consisting essentially of a major amount of a mineral lubricating oil and from about 0.5 to about 6% of a copolymer of lauryl methacrylate/Z-methyl-S-Vinyl-pyridine in the mol ratio of 1:1 to 7 :1, respectively, and having a molecular weight of 7 from 50,000 to 2,000,000 ancl.-from about 0.5% to about 6% byweight of zinc diamyl dithiocarbamate.
  • a lubricating composition consisting essentially of a major amount of a mineral lubricating oil and from about 0.5 to about 6% of a copolymer of stearyl methacrylate/vinyl pyrrolidone in' the mol ratio of 1:1 to 7:1, respectively, and having a molecular weight of from 50,000 to 2,000,000 and from about 0.5 to about 6% by weight of zinc dlamyl dithiocar-bamate.
  • a lubricating composition consisting essentially of a major amount of a mineral lubricating oil and'from about 0.5% to about 6% of a. copolymer of lauryl methacrylate/vinyl pyrrolidone in the mol ratio of 1:1 to 7:1, respectively, and having'a molecular weight of from 50,000

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
US651598A 1957-04-09 1957-04-09 Lubricating oil composition Expired - Lifetime US3030303A (en)

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NL105971D NL105971C (de) 1957-04-09
NL226646D NL226646A (de) 1957-04-09
BE566592D BE566592A (de) 1957-04-09
US651598A US3030303A (en) 1957-04-09 1957-04-09 Lubricating oil composition
GB11043/58A GB836303A (en) 1957-04-09 1958-04-08 Lubricating oil compositions
DEN14912A DE1063312B (de) 1957-04-09 1958-04-08 Schmiermittel
FR1206669D FR1206669A (fr) 1957-04-09 1958-04-09 Huiles lubrifiantes composées

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3131119A (en) * 1960-04-06 1964-04-28 Rohm & Haas Oil-dispersible dithiocarbamates
US3151076A (en) * 1959-05-28 1964-09-29 Shell Oil Co Oil additives and lube oils containing them
US3163605A (en) * 1959-08-12 1964-12-29 Roehm & Haas Gmbh Lubricating oil additives
US3166507A (en) * 1962-08-13 1965-01-19 Union Carbide Corp Lubricating oils containing alkyl acrylate-vinylpyridine n-oxide copolymers
US3171779A (en) * 1961-12-27 1965-03-02 Texaco Inc Plant composition
US3172856A (en) * 1965-03-09 Copolymers of n-alkyl piperazine acry- late and alkyl acrylate and lubricat- ing oils containing them
US3179591A (en) * 1960-04-25 1965-04-20 Shell Oil Co Lubricating compositions
US3206403A (en) * 1965-09-14 Distillate and raffinate
US3215632A (en) * 1962-06-22 1965-11-02 Shell Oil Co Lubricating compositions
US3224975A (en) * 1962-12-03 1965-12-21 Ethyl Corp Lubricating oil compositions
US3224968A (en) * 1962-12-03 1965-12-21 Ethyl Corp Lubricating oil compositions
US3265619A (en) * 1963-05-03 1966-08-09 Shell Oil Co Heavy duty lubricants
US3397146A (en) * 1966-08-22 1968-08-13 Union Carbide Corp Lubricating compositions
US3462367A (en) * 1966-10-31 1969-08-19 Shell Oil Co Lubricating oils containing an antioxidant mixture of zinc and antimony dialkyl dithiocarbamates
US3718591A (en) * 1967-11-27 1973-02-27 Shell Oil Co Lubricant compositions containing terpolymers
US4178258A (en) * 1978-05-18 1979-12-11 Edwin Cooper, Inc. Lubricating oil composition
US4181618A (en) * 1974-12-03 1980-01-01 Institut Francais Du Petrole Grafted copolymers and their use as additives for lubricating oils
US6210696B1 (en) 1998-04-27 2001-04-03 Rohm And Haas Company Stable pesticide dispersions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3116248A (en) * 1960-12-23 1963-12-31 Shell Oil Co Lubricating oil composition
NL272801A (de) * 1960-12-23
US3336225A (en) * 1966-01-17 1967-08-15 Dow Chemical Co Method and composition for reducing friction on conveyors

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US2450633A (en) * 1944-10-31 1948-10-05 California Research Corp Compounded oil
US2666044A (en) * 1951-03-09 1954-01-12 Du Pont Alkyl acrylate/n-hydrocarbon-substituted acrylamide/unsaturated tertiary amino compound copolymers
US2737496A (en) * 1952-02-16 1956-03-06 Du Pont Lubricating oil compositions containing polymeric additives
US2794781A (en) * 1955-02-25 1957-06-04 Shell Dev High temperature aromatic-free mineral lubricating oil compositions
US2825695A (en) * 1956-06-15 1958-03-04 Shell Dev Lubricating compositions
US2839512A (en) * 1955-12-30 1958-06-17 Shell Dev Vinylpyridine long chain acrylic ester copolymers and their preparation
US2866729A (en) * 1956-07-27 1958-12-30 Shell Dev Quenching oil compositions
US2889282A (en) * 1956-09-17 1959-06-02 Shell Dev Lubricating oil compositions

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DE947186C (de) * 1951-03-09 1956-08-09 Du Pont Zusatz zu Schmieroelen und Heizoelen
GB770771A (en) * 1953-05-18 1957-03-27 California Research Corp Copolymeric dispersants and lubricant compositions containing them
BE529084A (de) * 1953-05-25
NL92381C (de) * 1954-05-10

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US2450633A (en) * 1944-10-31 1948-10-05 California Research Corp Compounded oil
US2666044A (en) * 1951-03-09 1954-01-12 Du Pont Alkyl acrylate/n-hydrocarbon-substituted acrylamide/unsaturated tertiary amino compound copolymers
US2737496A (en) * 1952-02-16 1956-03-06 Du Pont Lubricating oil compositions containing polymeric additives
US2794781A (en) * 1955-02-25 1957-06-04 Shell Dev High temperature aromatic-free mineral lubricating oil compositions
US2839512A (en) * 1955-12-30 1958-06-17 Shell Dev Vinylpyridine long chain acrylic ester copolymers and their preparation
US2825695A (en) * 1956-06-15 1958-03-04 Shell Dev Lubricating compositions
US2866729A (en) * 1956-07-27 1958-12-30 Shell Dev Quenching oil compositions
US2889282A (en) * 1956-09-17 1959-06-02 Shell Dev Lubricating oil compositions

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3206403A (en) * 1965-09-14 Distillate and raffinate
US3172856A (en) * 1965-03-09 Copolymers of n-alkyl piperazine acry- late and alkyl acrylate and lubricat- ing oils containing them
US3151076A (en) * 1959-05-28 1964-09-29 Shell Oil Co Oil additives and lube oils containing them
US3163605A (en) * 1959-08-12 1964-12-29 Roehm & Haas Gmbh Lubricating oil additives
US3131119A (en) * 1960-04-06 1964-04-28 Rohm & Haas Oil-dispersible dithiocarbamates
US3179591A (en) * 1960-04-25 1965-04-20 Shell Oil Co Lubricating compositions
US3171779A (en) * 1961-12-27 1965-03-02 Texaco Inc Plant composition
US3215632A (en) * 1962-06-22 1965-11-02 Shell Oil Co Lubricating compositions
US3166507A (en) * 1962-08-13 1965-01-19 Union Carbide Corp Lubricating oils containing alkyl acrylate-vinylpyridine n-oxide copolymers
US3224975A (en) * 1962-12-03 1965-12-21 Ethyl Corp Lubricating oil compositions
US3224968A (en) * 1962-12-03 1965-12-21 Ethyl Corp Lubricating oil compositions
US3265619A (en) * 1963-05-03 1966-08-09 Shell Oil Co Heavy duty lubricants
US3397146A (en) * 1966-08-22 1968-08-13 Union Carbide Corp Lubricating compositions
US3462367A (en) * 1966-10-31 1969-08-19 Shell Oil Co Lubricating oils containing an antioxidant mixture of zinc and antimony dialkyl dithiocarbamates
US3718591A (en) * 1967-11-27 1973-02-27 Shell Oil Co Lubricant compositions containing terpolymers
US4181618A (en) * 1974-12-03 1980-01-01 Institut Francais Du Petrole Grafted copolymers and their use as additives for lubricating oils
US4178258A (en) * 1978-05-18 1979-12-11 Edwin Cooper, Inc. Lubricating oil composition
US6210696B1 (en) 1998-04-27 2001-04-03 Rohm And Haas Company Stable pesticide dispersions

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GB836303A (en) 1960-06-01
NL226646A (de)
NL105971C (de)
BE566592A (de)
FR1206669A (fr) 1960-02-11

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