WO2001072933A2 - Compositions d'huile permettant d'ameliorer les economies de carburant - Google Patents

Compositions d'huile permettant d'ameliorer les economies de carburant Download PDF

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Publication number
WO2001072933A2
WO2001072933A2 PCT/US2001/009566 US0109566W WO0172933A2 WO 2001072933 A2 WO2001072933 A2 WO 2001072933A2 US 0109566 W US0109566 W US 0109566W WO 0172933 A2 WO0172933 A2 WO 0172933A2
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Prior art keywords
monoester
mixture
glycerol
diester
carbon atoms
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PCT/US2001/009566
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English (en)
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WO2001072933A3 (fr
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Alexander B. Boffa
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Chevron Oronite Company Llc
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Priority to AU2001247771A priority Critical patent/AU2001247771A1/en
Publication of WO2001072933A2 publication Critical patent/WO2001072933A2/fr
Publication of WO2001072933A3 publication Critical patent/WO2001072933A3/fr

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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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/028—Overbased salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
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    • 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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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • 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
    • C10M2219/046—Overbasedsulfonic acid salts
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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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    • C10M2219/00—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
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
    • C10M2219/089—Overbased salts
    • 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
    • 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
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • C10M2227/062—Cyclic esters
    • C—CHEMISTRY; METALLURGY
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/063—Complexes of boron halides
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/065—Organic compounds derived from inorganic acids or metal salts derived from Ti or Zr
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
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    • 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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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • Esters and particularly glycerol esters, have been used as friction modifiers in motor oils.
  • U. S. Patent No. 4,495,088, issued January 22, 1985 to Listen discloses lubricating oils containing borated fatty acid esters of glycerol and a succinimide.
  • the fatty acid monoester of glycerol is said to be preferred, though mixtures of mono- and diesters may be used.
  • mixtures contain at least 40% of the monoester.
  • the mixtures of mono- and diesters contain from 40 to 60 percent by weight of the monoesters.
  • commercial glycerol monooleate contains a mixture of from 45 % to 55% by weight monoester and from 55% to 45 % diester.
  • U. S. Patent No. 4,683,069, issued July 28, 1987 to Brewster et al. discloses lubricating oil compositions which contain 0.05 to 0.2 wt. % of a glycerol partial ester of a C 16 -C 18 fatty acid as a fuel economy additive.
  • Optimum efficiency is said to be found at about the 0.2 weight percent level and use in excess of this amount is said to be possibly detrimental to the overall performance of the lubricating oil composition.
  • a mixture of glycerol monooleate (GMO) and glycerol dioleate (GDO) in a weight ratio of 3 parts GMO to 2 parts GDO is used in a lubricating oil.
  • GMO glycerol monooleate
  • GDO glycerol dioleate
  • Example 2 uses this GMO/GDO mixture at levels of 0.3, 0.5, 0.4 and 0.9 wt. %.
  • European Patent No. 0092946, published November 2, 1983 discloses lubricating oil compositions containing 0.2 wt.
  • Example 2 uses this GMO/GDO mixture at levels of 0.3, 0.5, 0.4 and 0.9 wt. %.
  • European Patent No. 0466297 published January 15, 1992, discloses the use of mono-, di- or triesters of glycerol in lubricating oils to improve compatibility with nitrile rubbers.
  • the ester can be used in an amount from 0.01 to 3.0 weight percent based on the weight of the oil composition.
  • a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and, in an amount effective to reduce fuel consumption in an internal combustion engine, a monoester of glycerol and a carboxylic acid containing 12 to 20 carbon atoms and 0 to 3 double bonds, or a mixture of a monoester and a diester of glycerol and a carboxylic acid containing 12 to 20 carbon atoms and 0 to 3 double bonds wherein at least 75 mole percent of the mixture is monoester.
  • Also provided in accordance with this invention is a method for reducing the fuel consumption of an internal combustion engine comprising treating the moving surfaces thereof with a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and, in an amount effective to reduce fuel consumption in the internal combustion engine, a monoester of glycerol and a carboxylic acid containing 12 to 20 carbon atoms and 0 to 3 double bonds, or a mixture of a monoester and a diester of glycerol and a carboxylic acid containing 12 to 20 carbon atoms and 0 to 3 double bonds wherein at least 75 mole percent of the mixture is monoester.
  • glycerol esters of fatty acids are prepared by reacting glycerol and a fatty acid.
  • the product of this reaction is often referred to as, e.g., glyceryl monooleate.
  • glyceryl monooleate is often referred to as, e.g., glyceryl monooleate.
  • glyceryl monooleate because the starting acid was oleic acid
  • a typical commercial product contains esters of acids other than oleic acid, because the "oleic acid” used to prepare the ester is, in fact, a mixture of acids of which oleic acid may constitute only about 70 mole percent of the acids.
  • a typical commercial "glyceryl monooleate” may actually contain only about 38-40 mole percent glyceryl monooleate.
  • Canadian Patent No. 1,137,463, issued December 14, 1982, and Canadian Patent No. 1,157,846, issued November 29, 1983 confirm this usage of the term "glyceryl monooleate" when referring to a mixture of mono-, di, and/or triesters.
  • esters of the present invention are also prepared by reacting glycerol and a C ⁇ 2 -C 2 o carboxylic acid containing 0 to 3 double bonds in a conventional manner well known in the art.
  • the preferred acid is oleic acid.
  • the resulting product is a mixture of mono-, di- and triesters.
  • this reaction mixture is then distilled using conventional techniques, and the monoester portion of the distillate is recovered. This can result in a product which is essentially all monoester.
  • the esters used in the lubricating oil compositions of this invention may be all monoesters, or a mixture of mono- and diesters in which at least 75 mole percent, preferably at least 90 mole percent, of the mixture is the monoester.
  • the monoester or mixture of mono- and diesters is used in an amount effective to reduce fuel consumption in an internal combustion engine.
  • the lubricating compositions of this invention contain at least 0.3, preferably 0.3 to 2.0 weight percent of the monoester or mixture of mono- and diesters.
  • the esters of this invention may also be borated. Boration passivates hydroxyl groups on the glycerol portion of the esters which helps improve compatibility with rubber seals.
  • the borated product can be prepared by borating the ester with boric acid with removal of the water of reaction.
  • there is sufficient boron present such that each boron will react with from 1.5 to 2.5 hydroxyl groups present in the reaction mixture.
  • the reaction may be carried out at a temperature in the range of 60°C. to 135°C, in the absence or presence of any suitable organic solvent such as methanol, benzene, xylenes, toluene, neutral oil and the like.
  • a method for borating esters is disclosed in U. S. Patent No. 4,495,088, issued January 22, 1985 to Liston, which is incorporated by reference.
  • the lubricating oil used in the compositions of this invention may be mineral or synthetic oils of viscosity suitable for use in the crankcase of an internal combustion engine.
  • Crankcase lubricating oils ordinarily have a viscosity of about 1300 cSt at 0°F. to 22.7 cSt at 210°F. (99°C).
  • the lubricating oils may be derived from synthetic or natural sources.
  • Mineral oils useful in this invention include paraffinic, naphthenic and other oils used in lubricating oil compositions.
  • Synthetic oils include both hydrocarbon synthetic oils and synthetic esters.
  • Useful synthetic hydrocarbon oils include liquid polymers of alpha olefms having the proper viscosity.
  • Useful synthetic esters include the esters of both monocarboxylic and polycarboxylic acids as well as monohydroxy alkanols and polyols. It has been found that the effect of the esters of this invention on lubricating oil compositions is most pronounced in oils that have a relatively low viscosity. Therefore, the preferred oils for use in the lubricating oil compositions of this invention are those with viscosity in the range of 6 to 13 cSt kinematic viscosity at 100 °C. and of 2000 cP at -30°C. to 3500 cP at -20°C. low temperature cranking viscosity as defined in Society of Automotive Engineering Specification J300..
  • the lubricating oil compositions of this invention may also contain additives other than the esters of this invention.
  • additives can comprise ashless dispersants which are typically nitrogen-containing dispersant additives that are oil soluble salts, amides, imides and esters made from high molecular weight mono- and dicarboxylic acids and various amines having an amino or heterocyclic nitrogen with at least one amido or hydroxy group capable of salt, amido, or ester formation.
  • ashless dispersants are typically nitrogen-containing dispersant additives that are oil soluble salts, amides, imides and esters made from high molecular weight mono- and dicarboxylic acids and various amines having an amino or heterocyclic nitrogen with at least one amido or hydroxy group capable of salt, amido, or ester formation.
  • Preferred are the reaction products of polyolefin (C 2 -C 5 olefin), such as polyisobutenyl, succinic anhydride with an alkylene polyamine such as
  • Dispersants are used generally in amounts from about 0.1 to 10 wt. %, preferably in the range of about 0.5 to 5 wt. % based on the weight of the lubricating oil composition.
  • Detergents may also be used in the lubricating oils compositions of this invention. They include the neutral, basic or overbased metal (normally alkali or alkaline earth metal) salts of petroleum naphthenic acids, petroleum sulfonic acids, alkylaryl sulfonic acids, alkyl phenols, alkylene-bis-phenol, oil soluble fatty acids and the like.
  • the preferred materials are the neutral or overbased calcium or magnesium phenates, sulfurized phenates and/or sulfonates. These detergents are typically used in amounts from 1 to 3 wt. % based on the total weight of the lubricating oil composition. Oxidation inhibitors may also be used. Examples of oxidation inhibitors include hindered phenols, such as 2,6-ditertiary butyl para-cresol, amines, sulfurized phenol and alkyl phenothiazines. Normally, they are used in amounts from about 0.01 to 3 wt. % based on the weight of the lubricating oil composition.
  • the lubricating oil compositions can also contain pour point depressants, which are usually present in amounts from about 0.01 to 1 wt. % based on the weight of the lubricating oil composition. They include wax alkylated aromatic hydrocarbons, olefin polymers and copolymers, and acrylate and methacrylate polymers and copolymers. Anti-wear additives may also be used. Typically they are oil soluble zinc dihydrocarbyldithiophosphates having at least a total of 5 carbon atoms, the alkyl group preferably being C 2 -C 8 . They are typically present in amounts of from 0.01 to 5 wt. %, preferably 0.5 to 1.5 wt.
  • Viscosity index improvers, or viscosity modifiers may also be included in the lubricating oil compositions of this invention. Normally, they are olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpolymers of styrene with isoprene and/or butadiene, polymers of alkyl acrylates and alkyl methacrylates, copolymers of alkyl methacrylates with N- vinyl pyrollidone or dimethylaminoalkyl methacrylate, post-grafted polymers of ethylene-propylene with an active monomer such as maleic anhydride which may be further reacted with an alcohol, or an alkylene polyamine, styrene-maleic anhydride polymers post-treated with alcohols and amines and the like.
  • an active monomer such as maleic anhydride which may be further reacted with an alcohol, or an alkylene poly
  • additives are used in amounts of about 1.5 to 15 wt. % based on the weight of the lubricating oil composition, depending on the exact viscosity specification desired.
  • the foregoing additives (other than the esters of this invention) are used in amounts normally necessary to provide their attendant functions in a fully formulated crankcase lubricating oil composition.
  • Very small proportions of additional special purpose additives, such as anti-foam agents or rust inhibitors may also be present in the lubricating oil compositions of this invention.
  • This invention will be further understood by reference to the following illustrative examples. The examples include preferred but non-limiting embodiments of the invention.
  • Lubricating oil compositions were formulated using the components indicated in the table below.
  • FCBC is the fuel consumption for the base case and FCSample is the fuel consumption for a given sample.
  • Weighting factors are derived from ASTM methods of fuel economy determination.
  • Sample B Base case oil with 0.3 wt. % of a mixture of 68 mole % borated glycerol monooleate (GMO) and 32 mole % borated glycerol dioleate (GDO)
  • Sample C Base case oil with 0.3 wt. % of a mixture of 68 mole % non-borated

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne des compositions d'huile lubrifiante renfermant une fraction majeure d'huile à viscosité lubrifiante et, en quantité suffisante pour réduire la consommation d'huile dans un moteur à combustion interne, un monoester de glycérol et un acide carboxylique renfermant entre 12 et 20 atomes de carbone et présentant entre 0 et 3 liaisons doubles, ou bien un mélange de monoester et de diester de glycérol et un acide carboxylique renfermant entre 12 et 20 atomes de carbone et présentant entre 0 et 3 liaisons doubles, sachant que le monoester représente au moins 75 % du mélange, en moles. Lesdites compositions sont utiles pour améliorer les économies de carburant dans les moteurs à combustion interne.
PCT/US2001/009566 2000-03-28 2001-03-23 Compositions d'huile permettant d'ameliorer les economies de carburant WO2001072933A2 (fr)

Priority Applications (1)

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AU2001247771A AU2001247771A1 (en) 2000-03-28 2001-03-23 Oil compositions having improved fuel economy efficiency

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US09/537,855 2000-03-28

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7256162B2 (en) 2003-09-26 2007-08-14 Arizona Chemical Company Fatty acid esters and uses thereof
DE102006054511A1 (de) * 2006-11-20 2008-05-21 Lothar Bendel Mehrkomponenten-Schmiermittel auf Esterbasis für Verbrennungsmotoren
EP1925655A1 (fr) 2006-11-22 2008-05-28 Infineum International Limited Compositions d'huile lubrifiante
EP2161326A1 (fr) 2008-09-05 2010-03-10 Infineum International Limited Compositions d'huile lubrifiante
EP2390306A1 (fr) 2009-12-01 2011-11-30 Infineum International Limited Composition d'huile de lubrification
EP2880140B1 (fr) 2012-07-30 2016-07-27 Shell Internationale Research Maatschappij B.V. Composition d'huile lubrifiante pour moteurs à combustion interne
EP3252130A1 (fr) 2016-06-03 2017-12-06 Infineum International Limited Ensemble d'additifs et composition d'huile lubrifiante

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EP0036708A1 (fr) * 1980-03-24 1981-09-30 Mobil Oil Corporation Additifs réduisant le frottement
US4495088A (en) * 1981-07-01 1985-01-22 Chevron Research Company Method for improving fuel economy of internal combustion engines
US4683069A (en) * 1981-05-06 1987-07-28 Exxon Research & Engineering Co. Glycerol esters as fuel economy additives
US5114603A (en) * 1988-02-08 1992-05-19 Amoco Corporation Friction reducing lubricating oil composition
EP0905221A1 (fr) * 1997-09-23 1999-03-31 NCH Corporation Compositions d'additifs multifonctionnels pour lubrifiants

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GB2038355A (en) * 1978-12-18 1980-07-23 Chevron Res Method of Improving Fuel Economy of an Internal Combustion Engine and Composition Therefor
EP0036708A1 (fr) * 1980-03-24 1981-09-30 Mobil Oil Corporation Additifs réduisant le frottement
US4683069A (en) * 1981-05-06 1987-07-28 Exxon Research & Engineering Co. Glycerol esters as fuel economy additives
US4495088A (en) * 1981-07-01 1985-01-22 Chevron Research Company Method for improving fuel economy of internal combustion engines
US5114603A (en) * 1988-02-08 1992-05-19 Amoco Corporation Friction reducing lubricating oil composition
EP0905221A1 (fr) * 1997-09-23 1999-03-31 NCH Corporation Compositions d'additifs multifonctionnels pour lubrifiants

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7256162B2 (en) 2003-09-26 2007-08-14 Arizona Chemical Company Fatty acid esters and uses thereof
DE102006054511A1 (de) * 2006-11-20 2008-05-21 Lothar Bendel Mehrkomponenten-Schmiermittel auf Esterbasis für Verbrennungsmotoren
DE102006054511B4 (de) * 2006-11-20 2009-06-10 Lothar Bendel Motorölzusammensetzung und deren Verwendung
EP1925655A1 (fr) 2006-11-22 2008-05-28 Infineum International Limited Compositions d'huile lubrifiante
EP2161326A1 (fr) 2008-09-05 2010-03-10 Infineum International Limited Compositions d'huile lubrifiante
EP2390306A1 (fr) 2009-12-01 2011-11-30 Infineum International Limited Composition d'huile de lubrification
EP2880140B1 (fr) 2012-07-30 2016-07-27 Shell Internationale Research Maatschappij B.V. Composition d'huile lubrifiante pour moteurs à combustion interne
RU2635555C2 (ru) * 2012-07-30 2017-11-14 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. Композиция смазочного масла для двигателей внутреннего сгорания
EP2880140B2 (fr) † 2012-07-30 2023-03-08 Shell Internationale Research Maatschappij B.V. Composition d'huile lubrifiante pour moteurs à combustion interne
EP3252130A1 (fr) 2016-06-03 2017-12-06 Infineum International Limited Ensemble d'additifs et composition d'huile lubrifiante

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AU2001247771A1 (en) 2001-10-08

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