GB647911A - Improved lubricating compositions and preparation of polymers for use therein - Google Patents
Improved lubricating compositions and preparation of polymers for use thereinInfo
- Publication number
- GB647911A GB647911A GB26709/47A GB2670947A GB647911A GB 647911 A GB647911 A GB 647911A GB 26709/47 A GB26709/47 A GB 26709/47A GB 2670947 A GB2670947 A GB 2670947A GB 647911 A GB647911 A GB 647911A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- hydroxyethyl
- hydroxypropyl
- methyl
- sulphide
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- 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
- C10M3/00—Liquid 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
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- 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
-
- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/043—Polyoxyalkylene ethers with a thioether group
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polymers suitable for use as lubricants are prepared by polymerizing an alkyl thioether or disulphide having the formula HO-R-(S)p-R-OH, where p is 1 or 2, and R is an organic radical, in the presence of a dehydration catalyst. Specified thioethers are bis-(2-hydroxyethyl), bis-(3-hydroxyamyl), bis - (6 - hydroxyhexyl), bis - (7 - hydroxyheptyl), bis - (6 - hydroxyhexyl), bis - (7 - hydroxyheptyl), bis-(8-hydroxyoctyl), bis-(9-hydroxynonyl), bis - (10 - hydroxydecyl) and bis-(12-hydroxydodecyl) sulphides and their homologues, 2 - hydroxyethyl - 2 - hydroxy-propyl, 2 - hydroxyethyl - 3 - hydroxypropyl sulphides and their homologues, bis-(1-methyl-2 - hydroxyethyl), bis - (1 - methyl - 3 - hydroxypropyl) sulphides and their homologues, (1-methyl-2-hydroxyethyl) (1-methyl-3-hydroxypropyl) sulphide, bis-(1,2-dimethyl-3-hydroxypropyl, sulphide and its homologues, bis-(di-methyl-hydroxymethyl) and bis-(1,1-dimethyl-2-hydroxyethyl) sulphides, (2-hydroxyethyl) (1 - methyl - 2 - hydroxyethyl), (2 - hydroxyethyl) (1,1 - dimethyl - 2 - hydroxyethyl) and (1 - methyl - 2 - hydroxyethyl) (1,1 - dimethyl - 2-hydroxyethyl) sulphides. Disulphides specified are bis-(g -hydroxypropyl), bis-(b -hydroxyethyl) and bis-(b -hydroxypropyl) disulphides. Suitable catalysts are concentrated sulphuric, nitric, hydrochloric, hydrobromic and hydroiodic acids, p-toluene sulphonic acid, aluminium chloride and boron trifluoride. Polymerization may be effected in liquid, solution, emulsion or gaseous phases, using diluents which may be liquid, e.g. dihydronaphthalenes, decahydronaphthalene, cycloheptane, 2,2,3-trimethylpentane, 2-methyl-3-ethylpentane, 2,4-dimethylheptane, 4-ethylheptane, 2-methyloctane, 2,6-dimethyloctane, 2,4,5,7-tetramethyloctane, 2-methylnonane and dihexyl, or gaseous, e.g. methane, ethane, propane and butane, at temperatures between 150 DEG and 300 DEG C. Alcohols may be present to etherify the polymers. Water may be removed by distillation or by dehydrating agents. Diluent removed by azeotropic distillation is preferably replaced to maintain a constant diluent/monomer ratio. After removal of catalyst the product is dehydrogenated and decolourized by percolation of solutions in benzene or toluene through fuller's earth or activated clays, followed by hydrogenation using a tungsten sulphide catalyst. The terminal hydroxyl groups of the polymers may be partially or completely esterified, e.g. to form nitrates, phosphates, sulphates or fatty acid esters, or etherified, using alkyl, aralkyl, alkoxyalkyl or alkylene halides or sodium monochloracetate, during or after polymerization. The products may be soluble in water, alcohols, esters, ethers and aromatic hydrocarbons. They are suitable for use as hydraulic brake fluids, grease bases, plasticizers for cellulose esters, e.g. nitrocellulose, and ethers, polymethacrylates and phenol-formaldehyde resins, extreme pressure additives for lubricating oils and, admixed with minor amounts of oxidation inhibitors, corrosion inhibitors or gelling agents, e.g. phenyl-a -naphthylamine, as lubricants.ALSO:Bis-(g -hydroxypropyl)-sulphide is prepared by exposing a mixture of allyl alcohol and hydrogen sulphide in a quartz tube to ultra-violet light and subjecting the product to fractional distillation. Similar thioethers may be prepared from methallyl, crotyl and isopropenyl alcohols. Bis - (b - hydroxy - a - methylethyl) - sulphide is prepared by heating at 100 DEG C. in an autoclave a mixture of allyl alcohol, hydrogen sulphide and di-n-butylamine as catalyst and fractionating. b - hydroxy - a - methylethyl mercaptan is obtained as a by-product. Bis-(g -hydroxypropyl)-disulphide is prepared by adding iodine dropwise to an aqueous solution of g -mercaptopropyl alcohol and potassium hydroxide, washing the product and fractionally distilling.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US647911XA | 1946-10-08 | 1946-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB647911A true GB647911A (en) | 1950-12-28 |
Family
ID=22058300
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26709/47A Expired GB647911A (en) | 1946-10-08 | 1947-10-03 | Improved lubricating compositions and preparation of polymers for use therein |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR953949A (en) |
GB (1) | GB647911A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4250046A (en) * | 1979-03-05 | 1981-02-10 | Pennwalt Corporation | Diethanol disulfide as an extreme pressure and anti-wear additive in water soluble metalworking fluids |
US4493533A (en) * | 1981-04-27 | 1985-01-15 | Hoffmann-La Roche Inc. | Immersion oil containing aliphatic thio compounds |
US4769164A (en) * | 1987-05-22 | 1988-09-06 | The Lubrizol Corporation | Anti-oxidant products |
US5037569A (en) * | 1987-05-22 | 1991-08-06 | The Lubrizol Corporation | Anti-oxidant products |
-
1947
- 1947-10-03 GB GB26709/47A patent/GB647911A/en not_active Expired
- 1947-10-08 FR FR953949D patent/FR953949A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4250046A (en) * | 1979-03-05 | 1981-02-10 | Pennwalt Corporation | Diethanol disulfide as an extreme pressure and anti-wear additive in water soluble metalworking fluids |
US4493533A (en) * | 1981-04-27 | 1985-01-15 | Hoffmann-La Roche Inc. | Immersion oil containing aliphatic thio compounds |
US4769164A (en) * | 1987-05-22 | 1988-09-06 | The Lubrizol Corporation | Anti-oxidant products |
US5037569A (en) * | 1987-05-22 | 1991-08-06 | The Lubrizol Corporation | Anti-oxidant products |
Also Published As
Publication number | Publication date |
---|---|
FR953949A (en) | 1949-12-15 |
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