GB748137A - Improvements in or relating to lubricating oil compositions - Google Patents
Improvements in or relating to lubricating oil compositionsInfo
- Publication number
- GB748137A GB748137A GB6820/53A GB682053A GB748137A GB 748137 A GB748137 A GB 748137A GB 6820/53 A GB6820/53 A GB 6820/53A GB 682053 A GB682053 A GB 682053A GB 748137 A GB748137 A GB 748137A
- Authority
- GB
- United Kingdom
- Prior art keywords
- metal
- residue
- phosphorus
- radical
- oil
- 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
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
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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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
- C10L1/2616—Organic compounds containing phosphorus containing a phosphorus-carbon bond sulfur containing
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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
- 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
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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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/20—Natural rubber; Natural resins
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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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- 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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- 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
- C10M2207/027—Neutral salts thereof
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- 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
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- 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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- 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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- 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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- 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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- 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
- C10M2215/10—Amides of carbonic or haloformic acids
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- 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
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
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- 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
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- 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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- 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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- 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
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
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- C10M2219/089—Overbased salts
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- C10M2223/047—Thioderivatives not containing metallic elements
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- 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
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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
- C10N2040/135—Steam engines or turbines
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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
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
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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
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
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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
- C10N2040/20—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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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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
- C10N2040/32—Wires, ropes or cables lubricants
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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
- C10N2040/34—Lubricating-sealants
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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
- C10N2040/36—Release agents or mold release agents
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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
- C10N2040/38—Conveyors or chain belts
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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
- C10N2040/40—Generators or electric motors in oil or gas winning field
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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
- C10N2040/42—Flashing oils or marking oils
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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
- C10N2040/44—Super vacuum or supercritical use
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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
- C10N2040/50—Medical uses
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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
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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
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- Oil, Petroleum & Natural Gas (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
Abstract
An additive for lubricating oils or other hydrocarbon products, e.g. motor fuels (see Group III) comprises an ester having the formula R1CH(OH)P(O)(R2)(R2) wherein R1 is hydrogen or a C1 to C12 hydrocarbon radical and R2 is a hydroxyl radical, a C1 to C30 alcohol residue, a sulphur-containing alcohol residue containing up to 30 carbon atoms, a C1 to C30 mercaptan residue, a phenol residue, an alkyl phenol residue, a thiophenol residue, an alkyl phenol sulphide residue, or a carbamic acid or thiocarbamic acid residue, at least one R2 being one of said organic groups, or (b) the product obtained by phosphosulphurizing the above ester, or (c) a polyvalent metal salt of either of the additives (a) and (b). R1 is preferably a straight or branched chain alkyl group, e.g. methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, n-hexyl, isooctyl, 2-ethylhexyl, decyl, and dodecyl. It may also be a cycloalkyl, aralkyl, aryl or alkaryl radical, e.g. methylcyclohexyl, ethyl cyclohexyl, phenylethyl, phenyl propyl, phenyl, cresyl, or tert-butyl phenyl. The hydrocarbon group in the alcohol residue R2 may be one of the above specified groups but should preferably contain 12 to 24 carbon atoms. Thus it may be a tetradecyl, hexadecyl, octadecyl or tetracosyl radical or an alkenyl radical such as decenyl, octadecenyl, or a C6-C24 polypropenyl radical. The additives may be obtained by condensing an aldehyde R1CHO with phosphorus trichloride and hydrolysing the resulting trichloro condensation product to form a hydroxy phosphonic acid R1CH(OH).P(O)(OH)2 which is then esterified with an alcohol or phenol. Several alcohols and phenols are specified, including sulphurized alcohols, sulphur-containing alcohols, e.g. 2-dodecyl-thioethanol, alkyl phenols, and alkyl phenol sulphides. Products in which R2 is a mercaptan, thiophenol, carbamic acid or thiocarbamic acid residue may be obtained by reacting a phosphonic acid chloride R1CH(OH)P(O)(Cl)2 with a metal mercaptide, thiophenolate, carbamate, or thiocarbamate. The metal salts may be prepared by treating the partial esters (containing one P-OH group) with a finely-divided metal oxide or hydroxide. Specified metals are Group II metals, e.g. calcium. barium, magnesium, and strontium; also nickel, cobalt, tin, lead, zinc, copper, aluminium, iron, and manganese. The neutralization to form the salt may be carried out in a lubricant base oil. The metal may also be used in the form of metal carbide or metal alkoxide. The phosphosulphurized products may be prepared by reacting the esters with a sulphide of phosphorus such as P2S3, P2S5, P4S3\t or P4S7 or mixtures thereof or with mixtures of elemental sulphur and elemental phosphorus. A mixture of one or more sulphides of phosphorus and elemental sulphur and/or elemental phosphorus may also be used. The phospho-sulphurization may be carried out in an organic solvent or in a lubricant base oil. Metal salts of the phosphosulphurized products may be obtained by a procedure similar to that described above for the preparation of the metal salts of the esters. Examples describe the production of: (1) the partial ester of 1-hydroxy-n-butylphosphonic acid and tertiary octylphenol sulphide by reacting them together in the presence of xylene and concentrated sulphuric acid and removing the water formed; (2) the calcium salt of the product of (1) by dissolving the latter in ether and adding the solution to a suspension of calcium hydroxide in ice and water; (3) the calcium salt of the partial ester octadecenyl-1-hydroxy-n-butyl phosphonate by reacting 1-hydroxy-n-butyl-phosphonic acid, and oleyl alcohol in xylene while removing the water formed and then reacting with calcium hydroxide as in (2); (4) the calcium salt of the ester of 1-hydroxy-n-butylphosphonic acid and sulphurized oleyl alcohol by a procedure similar to that used in (3); and (5) the calcium salt of the product obtained by reacting the partial ester formed in (3) with phosphorus pentasulphide in the presence of dioxane, the calcium salt being formed by neutralizing the phospho - sulphurized product with sodium hydroxide and then adding an aqueous solution of calcium chloride.ALSO:A lubricating oil composition comprises a major proportion of a lubricating oil and a minor proportion of an additive comprising (a) an ester having the formula R1CH(OH). P(O)(R2)(R2) wherein R1 is hydrogen or a C1 to C12 hydrocarbon radical and R2 is a hydroxyl radical, a C1 to C30 alcohol residue, a sulphur-containing alcohol residue containing up to thirty carbon atoms, a C1 to C30 mercaptan residue, a phenol residue an alkyl phenol residue, a thiophenol residue, an alkyl phenol sulphide residue, or a carbamic acid or thiocarbamic acid residue, at least one R2 being one of said organic groups, or (b) the product obtained by phosphosulphurizing the above ester or (c) a polyvalent metal salt of either of the additives (a) and (b). R1 is preferably a straight or branched chain alkyl group, e.g. methyl, ethyl, propyl, isopropyl, butyl, tert.-butyl, n-hexyl, isooctyl, 2-ethylhexyl, decyl and dodecyl. It may also be a cycloalkyl, an alkyl aryl or alkaryl radical, e.g. methylcyclohexyl, ethyl-cyclohexyl, phenylethyl, phenylpropyl, phenyl, cresyl, or tert.-butyl phenyl. The hydrocarbon group in the alcohol residue R2 may be one of the above specified groups but should preferably contain 12 to 24 carbon atoms. Thus it may be a tetradecyl, hexadecyl, octadecyl or tetracosyl radical or an alkenyl radical such as decenyl, octadecenyl, or a C6-C24 polypropenyl radical. The additives may be obtained (see Group IV(b)) by condensing an aldehyde (R1CHO) with phosphorus trichloride and hydrolyzing the resulting trichloro condensation product to form a hydroxy phosphonic acid of the formula R1CH(OH). P(O)(OH)2 which is then esterified with an alcohol or phenol. Several alcohols and phenols are specified including sulphur-containing alcohols, alkyl phenols and alkyl phenol sulphides. Products in which R2 is a mercaptan, thiophenol, carbamic acid or thiocarbamic acid residue may be obtained by reacting a phosphoric acid chloride R1CH(OH)P(O) (Cl)2 with a metal mercaptide, thiophenolate, carbamate or thiocarbamate. The metal salts may be prepared by treating the partial esters (containing one P-OH group) with a finely divided metal oxide or hydroxide. Specified metals are Group II metals, e.g. calcium, barium, magnesium, and strontium; also nickel, cobalt, tin, lead, zinc, copper, aluminium, iron and manganese. The metal may also be used in the form of metal carbide or metal alkoxide. The neutralization to form the salt may be carried out in a lubricant base oil. The phospho-sulphurized products may be prepared by reacting the esters with a sulphide of phosphorus such as P2S3, P2S5, P4S3 or P4S7 or mixtures thereof or with mixtures of elemental sulphur and elemental phosphorus. A mixture of one or more sulphides of phosphorus and elemental sulphur and/or elemental phosphorus may also be used. The phosphosulphurization may be carried out in an organic solvent or in a lubricant base oil. Metal salts of the phosphosulphurized products may be obtained by a procedure similar to that described above for the preparation of the metal salts of the esters. The additives are preferably added to the lubricating oil in proportions of from 0.01 per cent to 15 per cent by weight of the total composition. Other additives such as phenols, phenol sulphides, metal soaps, metal petroleum sulphonates, metal phenates, metal alcoholates, metal alkyl phenol sulphides, metal organo-phosphates, -phosphites,- thiophosphates and -thiophosphites, metal-xanthates, -thioxanthates, and thiocarbamates may also be present. Other agents which may be present are dyes, pour point depressants, heat thickened fatty oils, sulphurized fatty oils, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, and olefin polymers. The lubricating oil base stock may be a straight mineral lubricating oil or distillate, a hydrogenated oil, a white oil, or a synthetic oil such as the polyether or polyester type or one prepared by the polymerization of olefins, by the reaction of oxides of carbon with hydrogen, or by the hydrogenation of coal or its products. Mixtures of such synthetic lubricants with mineral oil lubricants may also be used and in some cases cracking coal tar fractions and coal tar or shale oil distillates may be used. The additives may also be employed in other mineral oil compositions and hydrocarbon products, e.g. in motor fuels, mineral oil base hydraulic fluids, torque converter fluids, cutting oils, flushing oils, turbine oils, transformer oils, industrial oils, gear lubricants and greases. Examples describe the production of (1) the partial ester of 1-hydroxy-n-butylphosphonic acid and tertiary octyl phenol sulphide and its calcium salt: (2) the calcium salt of the partial ester-octadecnyl 1-hydroxy-n-butyl phosphonic acid and sulphurized oleyl alcohol; and (4) the calcium salt of the product obtained by reacting the partial ester-octadecenyl -1- hydroxy-n-butyl phosphonate with phosphorus pentasulphide. The results of a carbon slack dispersion test on a solvent extracted paraffinic base oil containing 1 per cent of the metal salt products of (1) (2) and 4 respectively and of a bearing corrosion test on a solvent extracted paraffinic lubricating oil containing 0.5 per cent of the partial ester product obtained in (1), the metal salt obtained in (1) and the product obtained in (2) respectively are given and compared with the results obtained with the base oil above.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US288955A US2758971A (en) | 1952-05-20 | 1952-05-20 | Blending agents for mineral oils |
Publications (1)
Publication Number | Publication Date |
---|---|
GB748137A true GB748137A (en) | 1956-04-25 |
Family
ID=23109388
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6820/53A Expired GB748137A (en) | 1952-05-20 | 1953-03-12 | Improvements in or relating to lubricating oil compositions |
Country Status (2)
Country | Link |
---|---|
US (1) | US2758971A (en) |
GB (1) | GB748137A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987002714A1 (en) * | 1985-10-28 | 1987-05-07 | Giovanni Bozzetto S.P.A. | Process for the preservation of organic products |
WO1990009425A1 (en) * | 1989-02-08 | 1990-08-23 | The Lubrizol Corporation | Lubricants containing salts of hydroxyalkane phosphonic acids |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2879285A (en) * | 1955-12-30 | 1959-03-24 | Monsanto Chemicals | Dialkyl and di (haloalkyl) alpha-mercaptophosphonate esters and process for their preparation |
DE1067162B (en) * | 1957-04-25 | 1959-10-15 | Esso Research and Engineering Company, Elizabeth, N. J. (V. St. A.J | Lubricants and methods of making the same |
US2982727A (en) * | 1957-12-31 | 1961-05-02 | Exxon Research Engineering Co | Lubricants containing salts and esters of oxygen-containing acids of phosphorus |
US3001938A (en) * | 1958-04-01 | 1961-09-26 | Exxon Research Engineering Co | Lubricants containing salts of organic-substituted phosphorus - containing acids |
NL121615C (en) * | 1958-09-06 | 1900-01-01 | ||
US3247113A (en) * | 1961-11-13 | 1966-04-19 | Shell Oil Co | Lubricating compositions and additives therefor |
NL129043C (en) * | 1964-08-14 | |||
US3477953A (en) * | 1966-11-29 | 1969-11-11 | Hooker Chemical Corp | Sequestration of metal ions with hydroxyalkyl phosphine oxides |
US3644206A (en) * | 1968-11-14 | 1972-02-22 | Mobil Oil Corp | Lubricating oils or fuels containing adducts of phosphorodithioate esters |
US4475943A (en) * | 1981-07-01 | 1984-10-09 | Monsanto Company | Herbicidal α-hydroxy phosphonates |
US4529528A (en) * | 1983-12-14 | 1985-07-16 | Mobil Oil Corporation | Borated amine-phosphite reaction product and lubricant and fuel containing same |
JPS61280499A (en) * | 1985-06-05 | 1986-12-11 | Sumitomo Chem Co Ltd | Amine adduct compound of aluminum phosphinate and plant blight controlling agent containing said compound as active component |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2228671A (en) * | 1938-10-04 | 1941-01-14 | Standard Oil Co | Compounded mineral oil |
US2311305A (en) * | 1940-05-06 | 1943-02-16 | Union Oil Co | Method of producing lubricating material |
US2279502A (en) * | 1940-10-09 | 1942-04-14 | Eastman Kodak Co | Yarn conditioning process and composition therefor |
GB549296A (en) * | 1941-04-12 | 1942-11-16 | Du Pont | Manufacture of improved lubricants |
GB552061A (en) * | 1941-09-18 | 1943-03-22 | Siegfried Ltd B | Improvements in or relating to the preparation of organic phosphinous acids |
US2420893A (en) * | 1944-01-04 | 1947-05-20 | Standard Oil Dev Co | Compounded lubricating oil |
US2476813A (en) * | 1946-12-20 | 1949-07-19 | Union Oil Co | Lubricating composition |
US2506310A (en) * | 1946-12-28 | 1950-05-02 | Standard Oil Dev Co | Lubricating oil composition |
US2579810A (en) * | 1949-08-18 | 1951-12-25 | Research Corp | Process of preparing substituted hydroxymethylphosphonic esters |
-
1952
- 1952-05-20 US US288955A patent/US2758971A/en not_active Expired - Lifetime
-
1953
- 1953-03-12 GB GB6820/53A patent/GB748137A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987002714A1 (en) * | 1985-10-28 | 1987-05-07 | Giovanni Bozzetto S.P.A. | Process for the preservation of organic products |
WO1990009425A1 (en) * | 1989-02-08 | 1990-08-23 | The Lubrizol Corporation | Lubricants containing salts of hydroxyalkane phosphonic acids |
US5059335A (en) * | 1989-02-08 | 1991-10-22 | The Lubrizol Corporation | Lubricants containing salts of hydroxyalkane phosphonic acids |
AU623750B2 (en) * | 1989-02-08 | 1992-05-21 | Lubrizol Corporation, The | Lubricants containing salts of hydroxyalkane phosphonic acids |
Also Published As
Publication number | Publication date |
---|---|
US2758971A (en) | 1956-08-14 |
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