GB657750A - Lubricating compositions - Google Patents
Lubricating compositionsInfo
- Publication number
- GB657750A GB657750A GB23719/47A GB2371947A GB657750A GB 657750 A GB657750 A GB 657750A GB 23719/47 A GB23719/47 A GB 23719/47A GB 2371947 A GB2371947 A GB 2371947A GB 657750 A GB657750 A GB 657750A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- esterification
- prepared
- thioethers
- gamma
- 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
- 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
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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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more 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
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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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
- 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
-
- 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
- C10M2209/10—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
-
- 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
- C10M2209/10—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
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
-
- 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
- C10M2209/10—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
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
-
- 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
- C10M2209/10—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
- C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
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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
- 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
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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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
- 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
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino 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
- 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
-
- 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
- C10M2215/26—Amines
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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
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; 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
- 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
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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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
- 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)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A lubricating composition comprises an ester prepared by esterifying with a substituted or unsubstituted, saturated or unsaturated, aliphatic monocarboxylic acid one or both end groups of a liquid long-chain polyether which may be an oxygen ether or a mixed oxygen and sulphur ether and which itself has lubricating properties and has been prepared by polymerizing one or more alkylene oxides (other than unsubstituted ethylene oxide) alkylene (other than unsubstituted ethylene glycol) dihydroxy-thioethers and dihydroxy - polysulphides, together with an extreme pressure additive, an oxidation inhibitor, a gelling agent, a corrosion inhibitor or a bodying agent. Additives to the esters specified are: substituted phenols, aromatic amines, or minor amounts of organic acids to give corrosion resistance; Na, K, Li, Ba or Ca soaps as gelling agents; polymeric methacrylates as bodying agents; and sulphur, phosphorus and chlorine compounds as extreme pressure additives. Esterification of the long-chain polyether.-Acids specified: (1) Saturated-formic, acetic, propionic, butyric, valeric, caproic, enanthylic, caprylic, pelargonic, capric, undecylenic, lauric, tridecoic, myristic, pentadecanoic, palmitic, margaric, stearic, carnaubic, cerotic, and psyllic acids. (2) Mono-olefinic-acrylic, methacrylic, dimethacrylic, crotonic, isocrotonic, vinylacetic; pentenic acids-tiglic, angelic and senecioic; hexenic, teracrylic, hypogeic, oleic, elaidic, erucic and behenic acids. (3) Polyolefinic and acetylinic acids-sorbic, linoleic, linolenic; propiolic, 2-butynoic, 2-pentynoic, amyl propiolic, palmitolic, and stearolic acids. (4) Mixtures of acids found in natural products, e.g. the acids from linseed, rapeseed, cottonseed, tall, soya bean, corn, rice, sesame, and mustard seed oils. Oleic, linoleic, and linolenic are the preferred acids. Catalysts for the esterification comprise zinc chloride, hydrogen chloride, sulphuric acid, p-toluene sulphonic acid, phosphoric acids and metal oxides, e.g. titanium oxide. The esterification may be carried out in presence of a diluent, e.g. hexanes, heptanes, octanes, nonanes, decanes, and dodecanes. The esterification product is purified by treatment to remove catalyst, acids, water and solvents. Preparation of the polyethers.-In order to have lubricating properties these must have a chain of at least 10 carbon atoms. They may be prepared from (1) alkylene oxides, epihalohydrins, glycides; (2) glycols derived from ethylene oxide or trimethylene glycol; the polymethylene glycols may have non-hydrocarbon radicals as substituents, e.g. hydroxyl, carboxyl, carbonyl groups or S, Se, Te, P, or N atoms; (3) hydroxy thioethers and polysulphides; (4) copolymers of members of the same or different classes aforesaid. Long lists of members of the above classes are given in the Specification. The thioethers are of the general formula HO-R(S)pR-OH, where the R's are organic radicals and p is an integer from 1-6. They include primary dihydroxy thioethers of the general formula HO-R-CH2S-CH2-R-OH which may be prepared by "abnormal" condensation of unsaturated alcohols with hydrogen sulphide, e.g. bis (gamma-hydroxypropyl) sulphide is prepared by condensation of allyl alcohol and H2S in a quartz tube irradiated by a 25 degree watt mercury vapour lamp. Gamma-mercapto alcohol is a by-product of the above reaction and may be isolated in the fraction distilling off at 132-134 DEG C. When reacted with iodine and potassium hydroxide bis-(gamma-hydroxypropyl) disulphide was obtained. The following examples illustrate the preparation of polyethers and their esterification: (1) the 2-ethylhexoate ester of polytrimethylene glycol was prepared by heating 700 parts trimethylene glycol and 28 parts p-toluene sulphonic acid in boiling decalin for 72 hours; 450 parts ethyl hexoic acid in 900 parts benzene were then added and the mixture refluxed until water separation ceased. A red oil was obtained which was purified by treatment with activated carbon, washing with NaOH and distillation. (3) Trimethylene glycol was polymerized as above and then esterified by refluxing with acetic anhydride in presence of p-toluene sulphonic acid; (4) polymerized bis(gamma-hydroxypropyl) sulphide and polymerized trimethylene glycol were acetylated as in (3); (5) glycidyl isopropyl ether was polymerized in presence of SnCl2, the polymer was acetylated as in (3). The Specification as open to inspection under Sect. 91 referred to the esterification of thio ethers having hydroxyl substituents on both organic radicals attached to the sulphur atoms. This subject-matter does not appear in the Specification as accepted.ALSO:Esters having lubricating properties are prepared by esterifying with a substituted or unsubstituted, saturated or unsaturated, aliphatic monocarboxylic acid, one or both end groups of a liquid long-chain polyether which may be an oxygen ether or a mixed oxygen and sulphur ether and which itself has lubricating properties and has been prepared by polymerizing one or more alkylene oxides (other than unsubstituted ethylene oxide), alkylene glycols (other than unsubstituted ethylene glycol), dihydroxy - thioethers and dihydroxy - polysulphides. Acids specified for the esterification are: (1) saturated-formic, acetic, propionic, butyric, valeric, caproic, enanthylic, caprilyic, pelargonic, capric, undecylenic, lauric, tridecoic, myristic, pentadecanoic, palmitic, margaric, stearic, carnaubic, carotic, and psyllic acids; (2) mono-olefinic-acrylic, methacrylic, dimethyacrylic, crotonic, isocrotonic, vinylacetic; pentenic acids such as tiglic, angelic and senecioic; hexenic, teracrylic, hypogeic, oleic, elaidic, erucic and behenic acids; (3) polyolefinic and acetylinic acids-sorbic, linoleic, linolenic; propiolic, 2-butynoic, 2-pentynoic, amyl propiolic, palmitolic, and stearolic acids; (4) mixtures of acids found in natural products, e.g. the acids from linseed, rapeseed, cottonseed, tall, soyabean, corn, rice, sesame, and mustard seed oils. Reference is made to hydroxy, ketonic and amino acids and sulphur-treated unsaturated acids, e.g. oleic acid. Oleic, linoleic, and linolenic are the preferred acids. Catalysts for the esterification comprise zinc chloride, hydrogen chloride, sulphuric acid, p-toluene sulphonic acid, phosphoric acids and metal oxides, e.g. titanium oxide. The esterification may be carried out in presence of a diluent, e.g. hexanes, heptanes, octanes, nonanes, decanes, and dodecanes. The esterification product is purified by treatment to remove catalyst, acids, water and solvents. The polyether starting materials-in order to have lubricating properties-must have a chain of at least 10 carbon atoms. They may be prepared from (1) alkylene oxides, epihalohydrins, glycides; (2) glycols, e.g. those derived from ethylene or trimethylene glycol; the latter glycols have the general formul <FORM:0657750/IV (b)/1> or <FORM:0657750/IV (b)/2> where s is an integer and the free valencies are satisfied by hydrogen or organic radicals and such radicals include, for the trimethylene glycols, hydroxyl, carboxyl and carbonyl groups and also S, Se, Te, P or N atoms; higher polymethylene glycols are also mentioned; (3) hydroxy thioethers and polysulphides; (4) copolymers of members of the same of different classes aforesaid. Long lists of members of the above classes are given in the Specification. The thioethers are of the general formula HO-R(S)pR-OH, where the R's are organic radicals, preferably saturated aliphatic hydrocarbon radicals which, however, may contain carboxy, carbonyl or hydroxy groups, and p is an integer preferably from 1-6. They include primary dihydroxy thioethers of the general formula HO-R-CH2S-CH2-R-OH, which may be prepared by "abnormal" condensation of unsaturated alcohols with hydrogen sulphide, e.g. bis-(gamma-hydroxypropyl) sulphide is prepared by condensation of allyl alcohol and H2S in a quartz tube irradiated by a 250-watt mercury vapour lamp; other suitable alcohols are mentioned. Gamma-mercapto propyl alcohol is a by-product of the above reaction and may be isolated in the fraction distilling off at 132-134 DEG C. When reacted with iodine and potassium hydroxide bis - (gamma - hydroxypropyl) disulphide was obtained. The polysulphides have the same general formula but p is preferably 2 to 6. The following examples illustrate the preparation of polyethers and their esterification. Lubricating compositions comprising the ester products of the invention are described (see Group III). (1) 2-ethyl-hexoate ester of polytrimethylene glycol.-700 parts trimethylene glycol and 28 parts p-toluene sulphonic acid were heated in boiling decalin for 72 hours; 450 parts ethyl hexoic acid in 900 parts benzene were then added and the mixture refluxed until water separation ceased. A red oil was obtained which was purified by treatment with activated carbon, washing with NaOH, and distillation. (3) Trimethylene glycol was polymerized as above and then esterified by refluxing with acetic anhydride in presence of p-toluene sulphonic acid. (4) Polymerized bis-(gamma-hydroxypropyl) sulphide and polymerized trimethylene glycol were acetylated as in (3). (5) Glycidyl isopropyl ether was polymerized in presence of SnCl2, the polymer was acetylated as in (3). The Specification as open to inspection under Sect. 91 relates to the preparation of esters of compounds having the general formula H[(O-R3)m-(StR4)p-1]n-OH, where R3 and R4 are organic radicals and m, n, p and t are integers including one, by esterification of polymers and copolymers of alkylene oxides, alkylene glycols, monomers and polymers of hydroxy thioethers and of hydroxy polysulphides by means of the appropriate carboxylic acids or the corresponding salts, anhydrides, cyanides and chlorides. The acids mentioned include, in addition to the above-specified acids, aliphatic
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US657750XA | 1946-08-31 | 1946-08-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB657750A true GB657750A (en) | 1951-09-26 |
Family
ID=22065015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23719/47A Expired GB657750A (en) | 1946-08-31 | 1947-08-27 | Lubricating compositions |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR952622A (en) |
GB (1) | GB657750A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1132123B (en) * | 1955-06-07 | 1962-06-28 | Inst Francais Du Petrol | Process for the preparation of castor oil fatty acid polyethylene glycol esters suitable as lubricating oils |
US3189547A (en) * | 1959-07-03 | 1965-06-15 | Shell Oil Co | Lubricating compositions |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE930102C (en) * | 1952-11-08 | 1955-07-11 | Bayer Ag | Lubrication of refrigeration systems |
-
1947
- 1947-08-27 GB GB23719/47A patent/GB657750A/en not_active Expired
- 1947-09-01 FR FR952622D patent/FR952622A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1132123B (en) * | 1955-06-07 | 1962-06-28 | Inst Francais Du Petrol | Process for the preparation of castor oil fatty acid polyethylene glycol esters suitable as lubricating oils |
US3189547A (en) * | 1959-07-03 | 1965-06-15 | Shell Oil Co | Lubricating compositions |
Also Published As
Publication number | Publication date |
---|---|
FR952622A (en) | 1949-11-21 |
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