GB604370A - Improvements in or relating to extreme pressure lubricating oil compositions - Google Patents
Improvements in or relating to extreme pressure lubricating oil compositionsInfo
- Publication number
- GB604370A GB604370A GB15291/45A GB1529145A GB604370A GB 604370 A GB604370 A GB 604370A GB 15291/45 A GB15291/45 A GB 15291/45A GB 1529145 A GB1529145 A GB 1529145A GB 604370 A GB604370 A GB 604370A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloraralkyl
- ethyl
- trithiocarbonate
- acid
- benzyl
- 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
Links
Classifications
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
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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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
-
- 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
- C10M2203/04—Well-defined cycloaliphatic compounds
-
- 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
-
- 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
- C10M2203/102—Aliphatic fractions
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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
- 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
- C10M2203/104—Aromatic fractions
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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
- 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
- C10M2203/106—Naphthenic fractions
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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
- 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
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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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
- 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
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
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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
- 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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- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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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
- 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
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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
- 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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- 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
- C10N2040/02—Bearings
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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
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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
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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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
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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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
- 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
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Abstract
The film strength or E.P. properties of lubricating oils is improved by the addition of a minor proportion (usually 1-10 per cent) of a chloraralkyl ester of a thio acid of the type <FORM:0604370/III/1> , where R is a chlor substituted aralkyl radicle, Y is oxygen or sulphur, at least one of them being sulphur, and R1 represents an alkyl, aryl, aralkyl or alkylaryl radicle or may be identical with R. The chlor benzyl xanthates, which form the subject of Specification 604,388 are excluded. Examples are a chlor phenalkyl ester of a thio acid, such as a chlorophen-alkyl trithiocarbonate; a chlorbenzyl ester of a thio acid, e.g. a chlorbenzyl thiocarbonate, or a chlorbenzyl ester of a thiocarbonic acid, such as trithiocarbonic acid. Among the compounds described are di-(trichloro benzyl) trithiocarbonate, and trichlor benzyl butyl trithiocarbonate. Chlorbenzyl esters or mono- and dithiocarbamic acids are also described, e.g. trichlor benzyl diethyl dithiocarbamate. The additives described are more effective and more chemically stable than the corresponding Cl-free compounds and are not corrosive. Most of them are freely soluble in lubricating oils, and concentrates containing up to 50 per cent or more of additive can be prepared. Seven per cent concentrations of these additives in a mineral lubricating oil of 10111 S.U. viscosity at 210 DEG F. gave film strengths of up to 365 lb. and 40 lb. in the standard S.A.E. and Alman testers respectively, while the viscosity increase at 210 DEG F. did not exceed 17 per cent after heating for 100 hours at 300 DEG F. in open beakers.ALSO:Chloraralkyl esters of thio acids are obtained by reacting a chloraralkyl chloride with an alkali metal salt of the thio acid and separating the salt split out in the formation of the desired ester. Thus, di-(chloraralkyl) trithiocarbonates are prepared by first reacting sodium sulphide and carbon disulphide in methanol solution, then refluxing the solution with the chloraralkyl chloride, removing the solvent by distillation under vacuum and the sodium chloride by washing with water. Mono-(chloraralky) alkyl trithiocarbonates are prepared by first reacting the alkyl mercaptan with ethanol and caustic soda, followed by refluxing with the chloraralkyl chloride and purifying as above. Alternatively, the chloraralkyl chloride may be reacted with a methanol solution of sodium trithiocarbonate and the product, after removal of the solvent, dissolved in benzene to facilitate washing with water. O-ethyl-S-chloraralkyl monothiocarbonates are prepared by reacting the chloraralkyl chloride with a solution of Bender's salt in ethanol, pouring the mixture into an excess of water and extracting the oil with a volatile solvent such as ether from which it is subsequently recovered. The chloraralkyl esters of benzothiolic acid are prepared by reacting the chloraralkyl chloride with a suspension of the potassium salt of benzothiolic acid in ethanol. The latter salt was prepared by reacting benzoyl chloride with an alcoholic solution of potassium hydrogen sulphide, precipitating the benzothiolic acid formed by the addition of hydrochloric acid, and neutralizing with aqueous potassium hydroxide. Mono-(chloraralkyl) dialkyl dithiocarbamates are prepared by reacting the chloraralkyl chloride with an ethanol solution of the diethyl amine salt of the dialkyl dithiocarbamic acid prepared by reacting diethyl amine with a solution of carbon disulphide in the alkyl alcohol, e.g. ethanol. After removal of the solvent the reaction product was washed with water, dilute hydrochloric acid and finally water again, preferably with the aid of a water immiscible solvent. After removal of the latter the residue was dried and filtered through a bed of adsorbtive decolorising clay. Chlor phenyl ethyl, ethyl xanthates are prepared by the chloride of the chlor phenyl ethyl benzene dissolved in acetone or ethanol with potassium ethyl xanthate at refluxing temperature. Examples of chloraralkyl esters of thio acids mentioned are di-(trichlor benzyl) trithio-carbonate, trichlor benzyl butyl trithiocarbonate, o-chlor benzyl butyl trithiocarbonate, di-(o-chlor benzyl) tritiocarbonate, o-ethyl s-trichlor benzyl-monothiocarbonate, trichlor benzyl diethyl dithiocarbamate, dichlor diethyl phenyl ethyl, ethyl xanthate, a -(2,4-dichlor phenyl) ethyl trithiocarbonate, di-(chlor ethyl phenyl ethyl) trithiocarbonate, di-(dichlorethyl phenyl ethyl) trithiocarbonate, di-(trichlor ethyl phenyl ethyl) trithiocarbonate, di-(tetrachlor ethyl phenyl ethyl) trithiocarbonate, the trichlor benzyl ester of benzothiolic acid, and trichlor phenyl ethyl, ethyl xanthate. Most or all of these products are oily liquids moderately to freely soluble in mineral (hydrocarbon) lubricating oils. The chloraralkyl chlorides were prepared by catalytic chlorination, using iron filings as catalyst for ring chlorination and exposure to ultra-violet light for chlorination of the side chains. Specification 604,388 is referred to.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US540891A US2438599A (en) | 1944-06-17 | 1944-06-17 | Lubricating oil composition |
US542607A US2396487A (en) | 1944-06-17 | 1944-06-28 | Chloraralkyl esters of thio acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB604370A true GB604370A (en) | 1948-07-02 |
Family
ID=27066547
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15291/45A Expired GB604370A (en) | 1944-06-17 | 1945-06-15 | Improvements in or relating to extreme pressure lubricating oil compositions |
Country Status (2)
Country | Link |
---|---|
US (2) | US2438599A (en) |
GB (1) | GB604370A (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3172900A (en) * | 1965-03-09 | v-oc-schs | ||
US2560371A (en) * | 1945-12-29 | 1951-07-10 | Standard Oil Dev Co | Sulfur-halogen compound |
US2491772A (en) * | 1945-12-29 | 1949-12-20 | Standard Oil Dev Co | Extreme pressure lubricants |
US2600737A (en) * | 1947-11-03 | 1952-06-17 | Phillips Petroleum Co | Method of making tertiary alkyl trithiocarbonates |
US2623018A (en) * | 1949-12-17 | 1952-12-23 | Standard Oil Dev Co | Extreme pressure lubricant |
US2673839A (en) * | 1951-04-28 | 1954-03-30 | Standard Oil Dev Co | Lubricating oil composition |
US2731487A (en) * | 1951-08-11 | 1956-01-17 | Stauffer Chemical Co | Asymmetric tertiary alkyl trithiocarbonates |
US2846461A (en) * | 1955-02-21 | 1958-08-05 | Universal Oil Prod Co | Production of esters of dithiocarboxylic acids |
NL280296A (en) * | 1961-07-03 | |||
CH429723A (en) * | 1963-06-12 | 1967-02-15 | Sandoz Ag | Process for the production of parasiticides |
US3328453A (en) * | 1963-08-07 | 1967-06-27 | Stauffer Chemical Co | Fluoroformal and fluorthioformal compounds and production thereof |
US3320298A (en) * | 1964-05-13 | 1967-05-16 | Velsicol Chemical Corp | Methyl s-isopropyl 2, 3, 5, 6-tetrahalo-monothioterephthalates |
US3311652A (en) * | 1964-10-13 | 1967-03-28 | Velsicol Chemical Corp | Methyl s-n-propyl 2, 3, 5, 6-tetrahalo-monothioterephthalate |
US3309391A (en) * | 1964-10-13 | 1967-03-14 | Velsicol Chemical Corp | Methyl s-allyl- and methyl s-propargyl-2, 3, 5, 6-tetrahalomonothioterephthalate |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2161566A (en) * | 1936-08-01 | 1939-06-06 | Socony Vacuum Oil Co Inc | Lubricating oil and method of protecting same |
NL62771C (en) * | 1938-08-03 | |||
US2368670A (en) * | 1939-10-06 | 1945-02-06 | Lubri Zol Dev Corp | Lubricating composition |
US2247045A (en) * | 1940-10-23 | 1941-06-24 | Socony Vacuum Oil Co Inc | Extreme pressure lubricant |
US2369150A (en) * | 1940-11-27 | 1945-02-13 | Continental Oil Co | Lubricating oil |
US2343393A (en) * | 1940-12-19 | 1944-03-07 | Phillips Petroleum Co | Lubricant |
-
1944
- 1944-06-17 US US540891A patent/US2438599A/en not_active Expired - Lifetime
- 1944-06-28 US US542607A patent/US2396487A/en not_active Expired - Lifetime
-
1945
- 1945-06-15 GB GB15291/45A patent/GB604370A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US2438599A (en) | 1948-03-30 |
US2396487A (en) | 1946-03-12 |
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