GB930504A - Boron and nitrogen-containing phosphor-sulphurized products, their preparation and their use as lubricant additives - Google Patents

Boron and nitrogen-containing phosphor-sulphurized products, their preparation and their use as lubricant additives

Info

Publication number
GB930504A
GB930504A GB41612/59A GB4161259A GB930504A GB 930504 A GB930504 A GB 930504A GB 41612/59 A GB41612/59 A GB 41612/59A GB 4161259 A GB4161259 A GB 4161259A GB 930504 A GB930504 A GB 930504A
Authority
GB
United Kingdom
Prior art keywords
product
acid
boric acid
boron
hydrocarbon
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
GB41612/59A
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.)
Standard Oil Co
Original Assignee
Standard Oil 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 Co filed Critical Standard Oil Co
Publication of GB930504A publication Critical patent/GB930504A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • 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
    • C10M159/00Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12Reaction products
    • C10M159/123Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/04Reaction products of phosphorus sulfur compounds with hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/34Introducing sulfur atoms or sulfur-containing groups
    • CCHEMISTRY; METALLURGY
    • 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
    • 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
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026Butene
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • CCHEMISTRY; METALLURGY
    • 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
    • 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
    • CCHEMISTRY; METALLURGY
    • 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
    • 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
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2225/00Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2225/00Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • C10M2225/041Hydrocarbon polymers
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2227/00Organic 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
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2227/00Organic 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
    • C10M2227/09Complexes with metals
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/06Groups 3 or 13
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Lubricants (AREA)

Abstract

A lubricating oil composition comprises a lubricating oil, such as hydrocarbon oils, both natural and synthetic, synthetic oils of the alkylene oxide type or polycarboxylic acid ester type, or polymerized olefines and from 0,0001 to 20% of the product of reaction of a hydrolysed phosphorous sulphide-hydrocarbon reaction product, an aliphatic amine selected from polyamines and hydroxyamines and a boron compound selected from boric acid, boric acid anhydride, boric acid esters, borophosphoric acid and fluoroboric acids. Concentrates of a suitable base oil containing more than 10%, for example up to 50%, of the boron and phosphorus-containing additives, alone or in combination with other additives, may be used for blending with lubricating oils. Specification 355,214 is referred to.ALSO:A boron and nitrogen-containing phosphorsulphurized product is made by reacting a phosphorus sulphide with a hydrocarbon polymer, hydrolysing the resulting product and reacting the hydrolysed product with an aliphatic amine compound selected from polyamines and hydroxy aliphatic amines and a boron compound selected from boric acid, boric acid anhydride, boric acid esters, borophosphoric acid and fluoroboric acids, such as difluoroboric acid and monofluoroboric acid. The polymer may be a mono-olefin polymer, copolymer or graft polymer. Polymers or copolymers of isomono-olefines, such as isobutylene and isoamylene having molecular weights from 150 to 50,000, polymers made by polymerizing the products from the vapour phase cracking of paraffin waxes or vapour phase cracked gasoline fractions, are mentioned. The hydrolysed phosphorus sulphide-hydrocarbon reaction product may be prepared by any known method. This product may be neutralized with up to 1,1 moles of amine compound per mole of acid phosphorus in the product and the resulting neutralized product is reacted with from 1 to 3 moles, based on boron, of the boron compound per mole of the resulting neutralized product. The reaction with the boron compound may be carried out in the presence of a solvent for the boron compound, the reactants heated to a temperature above 100 DEG C. and water stripped from the reaction mixture. Any solvent used is then stripped off. The product may be used as a lubricating oil additive. In examples, a hydrolysed phosphorus sulphide-hydrocarbon reaction product is made by reacting P2S5 with a butylene polymer of M.W. 750-800 at 450 DEG F. in a nitrogen atmosphere, and the product hydrolysed with steam at 300 DEG -400 DEG F.; the product is reacted with (1) ethylene diamine and boric acid; (2) a propylene diamine having a side chain derived from tallow fatty acid, and boric acid; (3) ethanolamine and boric acid; (4) triethanolamine and boric acid; (5) ethylenediamine and borophosphoric acid; (6) diethylenetriamine and difluoroboric acid; (7) triethylenetetramine and difluoroboric acid; (8) the amine used in (2) and difluoroboric acid. Specification 355,214 is referred to.ALSO:A boron and nitrogen-containing phosphorsulphurized product is made by reacting a phosphorus sulphide with a hydrocarbon, hydrolyzing the resulting phosphorus sulphide-hydrocarbon reaction product and reacting the hydrolyzed product with an aliphatic amine compound selected from boric acid, boric acid anhydride, boric acid esters, borophosphoric acid and fluoroboric acids, such as difluoroboric acid and monofluoroboric acid. The hydrocarbon used may be an olefin, paraffin, cycloparaffin, aromatic hydrocarbon, mono-olefine polymer, copolymer, graft polymer or petroleum fractions and the hydrolysed phosphorus sulphidehydrocarbon reaction product may be prepared by any known method. This product is neutralized with up to 1,1 moles of amine compound per mole of acid phosphorus in the product and the resulting neutralized product is reacted with from 1 to 3 moles, based on boron, of the boron compound per mole of the resulting neutralized product. The reaction with the boron compound may be carried out in the presence of a solvent for the boron compound, the reactants heated to a temperature above 100 DEG C. and water stripped from the reaction mixture. Any solvent used is then stripped in a vacuum or by passing nitrogen or other inert gasses through the mixture at a temperature sufficient to strip the solvent out. The product may be used as a lubricating oil additive. Specification 355,214 is referred to.
GB41612/59A 1958-12-08 1959-12-08 Boron and nitrogen-containing phosphor-sulphurized products, their preparation and their use as lubricant additives Expired GB930504A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US778576A US3108958A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
US778583A US3108959A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
US778606A US3089851A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same

Publications (1)

Publication Number Publication Date
GB930504A true GB930504A (en) 1963-07-03

Family

ID=27419742

Family Applications (1)

Application Number Title Priority Date Filing Date
GB41612/59A Expired GB930504A (en) 1958-12-08 1959-12-08 Boron and nitrogen-containing phosphor-sulphurized products, their preparation and their use as lubricant additives

Country Status (5)

Country Link
US (3) US3108959A (en)
DE (1) DE1255221B (en)
FR (1) FR1246407A (en)
GB (1) GB930504A (en)
NL (1) NL246131A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3185728A (en) * 1960-06-20 1965-05-25 Texaco Inc Ethylene diamine salts of thiophosphonic acids
US3294684A (en) * 1963-07-11 1966-12-27 Standard Oil Co Lubricant compositions containing detergency additives
US4438013A (en) 1983-05-27 1984-03-20 Olin Corporation Phosphorylated and thiophosphorylated poly(oxyalkylated) hydrazines and selected adducts and their use as corrosion inhibitors
US5026493A (en) * 1989-08-03 1991-06-25 Ethyl Petroleum Additives, Inc. Reduced ash content lubricants
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof
CN115820329B (en) * 2022-12-30 2023-10-31 太原理工大学 Lubricating oil with lamellar borophosphate amine compound as additive and preparation method thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2053474A (en) * 1934-12-11 1936-09-08 Du Pont Higher alkyl borates and silicates and process for preparing same
US2160917A (en) * 1937-06-10 1939-06-06 Standard Oil Co Lubricant
US2316082A (en) * 1941-03-24 1943-04-06 Standard Oil Co Lubricant
US2346156A (en) * 1942-02-16 1944-04-11 Standard Oil Co Compounded lubricant
US2636258A (en) * 1949-02-23 1953-04-28 Jones Allen Fluid can punch and opener
BE581744A (en) * 1950-12-22
US2636858A (en) * 1951-06-07 1953-04-28 Standard Oil Dev Co Mineral oil additive
US2809934A (en) * 1953-10-01 1957-10-15 Standard Oil Co Detergent lubricants and lubricating oil additives and process of making the same
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
US2900376A (en) * 1955-10-31 1959-08-18 Standard Oil Co Hydrolysis of phosphorus sulfide-hydrocarbon reaction product
US3002924A (en) * 1958-05-26 1961-10-03 Standard Oil Co Lubricant additive and composition containing same

Also Published As

Publication number Publication date
FR1246407A (en) 1960-10-10
NL246131A (en)
US3089851A (en) 1963-05-14
US3108959A (en) 1963-10-29
DE1255221B (en) 1967-11-30
US3108958A (en) 1963-10-29

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