GB717201A - Lubricating compositions - Google Patents

Lubricating compositions

Info

Publication number
GB717201A
GB717201A GB12974/52A GB1297452A GB717201A GB 717201 A GB717201 A GB 717201A GB 12974/52 A GB12974/52 A GB 12974/52A GB 1297452 A GB1297452 A GB 1297452A GB 717201 A GB717201 A GB 717201A
Authority
GB
United Kingdom
Prior art keywords
oil
oils
phosphorizing
terpene
lubricating
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
GB12974/52A
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 GB717201A publication Critical patent/GB717201A/en
Expired legal-status Critical Current

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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
    • 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
    • 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
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • 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
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • 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
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/24—Epoxidised acids; Ester derivatives thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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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
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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
    • 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
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • 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
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    • 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
    • C10M2209/082—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 monocarboxylic
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
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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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/08—Halogenated waxes
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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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
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
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    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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    • C10M2215/16—Nitriles
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    • C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
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    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
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    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/064—Thiourea type compounds
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    • C10M2219/083—Dibenzyl sulfide
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    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

Phosphorized terpene compounds are employed as ingredients of lubricating compositions (see Group III). The expression "terpene compound" is used to include not only monoterpenes but also the higher terpenes such as sesquiterpenes, diterpenes, and polyterpenes, and the oxygenated derivatives of all such terpenes. Suitable terpene compounds include alpha- and beta-pinene, dipentene, terpinolene, menthene, alpha-terpineol, camphene, limonene, turpentine, pine oil, camphor oil, terpenes obtained as a by-product in the manufacture of synthetic camphor, carene, fenchene, terpinene, camphoric acid and abietic acid. The phosphorizing agents used for the preparation of the phosphorized terpene compounds may be such that sulphur or selenium in addition to phosphorus is introduced into the terpene compound. Suitable phosphorizing agents are P2S5, P4S3, P2Se5, P2Se3, P, P2O5, POCl3, PCl3, PCl5, PSCl3 and H3PO4. The terpene compounds can also be first reacted with a sulphurizing or selenizing agent, e.g. SCl2, S2Cl2, sodium polysulphide, SeCl2 or SeCl4, and thereafter retreated with a phosphorizing agent, e.g. P2O5, P2S5 or phosphoric acid, so that the final reaction product contains both sulphur or selenium and phosphorus. If desired, the terpene compound may be first treated with a phosphorizing agent and then with a sulphurizing or selenizing agent. The final reaction product may be refined by solvent treatment or neutralized with a nitrogen base. Suitable organic nitrogen bases are amines, quaternary ammonium compounds, morpholine and piperidine. Examples are given of the phosphorizing of turpentine and alphapinene with P2S5.ALSO:A lubricating composition, particularly suitable for use in aviation engines, comprises a lubricating oil having incorporated therein a minor proportion of a phenol or thiophenol which is substituted by organic radicals at the ortho and para positions, at least one of the ortho substituents being an alkyl radical which is linked to the aromatic nucleus by a tertiary carbon atom, and a minor proportion of a phosphorized terpene compound. The lubricating oil may be a hydrocarbon oil or it may be a mineral oil blended with a fixed oil, such as castor oil or lard oil, and/or with a synthetic lubricating oil, such as polymerized olefins, copolymers of alkylene glycols and oxides, esters of polybasic organic and inorganic acids (e.g. di- (2-ethylhexyl) sebacate, dioctyl phthalate and trioctyl phosphate), polymeric tetrahydrofuran and silicone polymers (e.g. dimethyl silicone polymer). If desired, such synthetic lubricating oils may be used as the lubricating oil base either above or mixed with fixed oils. The expression "terpene compound" is used to include not only monoterpenes but also the higher terpenes such as sesquiterpenes, diterpenes, and polyterpenes, and the oxygenated derivatives of all such terpenes. Suitable terpene compounds include alpha- and betapinene, dipentene, terpinolene, menthene, alphaterpineol, camphene, limonene, turpentine, pine oil, camphor oil, terpenes obtained as a byproduct in the manufacture of synthetic camphor, carene, fenchene, terpinene, camphoric acid and abietic acid. The phosphorizing agents used for the preparation of the phosphorized terpene compounds may be such that sulphur or selenium in addition to phosphorous is introduced into the terpene compound. Suitable phosphorizing agents are P2S5, P4S3, P2Se5, P2Se3, P, P2O5, POCl3, PCl3, PCl5, PSCl3 and H3PO4. The terpene compounds can also first be reacted with a sulphurizing or selenizing agent, e.g. SCl2, S2Cl2, sodium polysulphide, SeCl2 or SeCl4, and thereafter re-treated with a phosphorizing agent, e.g. P2O5, P2S3 or phosphoric acid, so that the final reaction product contains both sulphur or selenium and phosphorus. If desired, the terpene compound may be first treated with a phosphorizing agent and then with a sulphurizing or selenizing agent. The final reaction product may be refined by solvent treatment or neutralized with a nitrogen base. Suitable organic nitrogen bases are amines, quaternary ammonium compounds, morpholine and piperidine. The lubricating composition may contain additional ingredients such as blooming agents, pour point depressants, viscosity improvers, extreme pressure agents, anti-foaming agents and detergents and a number of such ingredients are specified. The lubricating compositions may also be used as motor oils, turbine oils, steam cylinder oils, marine engine oils and refrigeration oils, and used for various lubrication purposes other than engine lubrication, such as slushing and flushing oils, rust inhibiting oils, quenching and drawing oils, greases and wax compositions. In the examples, mineral lubricating oil compositions are described wherein the phenol is 2, 6-ditert.-butyl-4-methylphenol or 2, 21-methylene bis (4-methyl-6-tert.-butyl phenol) and the phosphorized terpene compound is P2S5-turpentine or P2S5-alpha-pinene reaction product.
GB12974/52A 1951-05-25 1952-05-22 Lubricating compositions Expired GB717201A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US228356A US2684334A (en) 1951-05-25 1951-05-25 Lubricating oil containing a reaction product of p2s5-terpene and 2.4.6-trialkylphenol

Publications (1)

Publication Number Publication Date
GB717201A true GB717201A (en) 1954-10-20

Family

ID=22856855

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12974/52A Expired GB717201A (en) 1951-05-25 1952-05-22 Lubricating compositions

Country Status (4)

Country Link
US (1) US2684334A (en)
DE (1) DE947417C (en)
FR (1) FR1061981A (en)
GB (1) GB717201A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993856A (en) * 1957-11-18 1961-07-25 Texaco Inc Lubricant containing a sulfurized terpene and sulfurized sperm oil
US3102863A (en) * 1959-06-15 1963-09-03 Shell Oil Co Lubricating compositions
US3100748A (en) * 1959-11-10 1963-08-13 Shell Oil Co Lubricating compositions
US3328360A (en) * 1962-07-06 1967-06-27 Exxon Research Engineering Co Polymers containing phosphorus
CN104479736A (en) * 2014-12-03 2015-04-01 烟台市牟平区留德润滑油销售有限公司 Waste lube distillate oil refinement method

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2257872A (en) * 1940-11-09 1941-10-07 Gulf Research Development Co Insulating oil composition
US2486188A (en) * 1943-07-14 1949-10-25 Sinclair Refining Co Lubricant
NL71486C (en) * 1944-06-09
US2515281A (en) * 1946-06-06 1950-07-18 Sinclair Refining Co Process for preparing lubricating oil addends
US2489249A (en) * 1947-03-31 1949-11-29 Shell Dev Lubricant
US2515222A (en) * 1947-07-18 1950-07-18 Sinclair Refining Co Sulfurized condensate of alphapinene and phosphorus pentasulfide
NL142969B (en) * 1947-10-28 Monsanto Co PROCESS FOR PREPARING A MIXTURE CONTAINING POLYVINYL CHLORIDE AND / OR ONE OR MORE VINYL CHLORIDE VINYL ACETATE COPOLYMERS AND A PHTHALATE PROCESSING AGENT.

Also Published As

Publication number Publication date
US2684334A (en) 1954-07-20
DE947417C (en) 1956-08-16
FR1061981A (en) 1954-04-16

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