WO1993021288A1 - Composition de lubrifiant contenant un melange d'agents modifiant le frottement - Google Patents

Composition de lubrifiant contenant un melange d'agents modifiant le frottement Download PDF

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Publication number
WO1993021288A1
WO1993021288A1 PCT/US1993/003381 US9303381W WO9321288A1 WO 1993021288 A1 WO1993021288 A1 WO 1993021288A1 US 9303381 W US9303381 W US 9303381W WO 9321288 A1 WO9321288 A1 WO 9321288A1
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Prior art keywords
composition
carbon atoms
oil
amine
weight
Prior art date
Application number
PCT/US1993/003381
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English (en)
Inventor
Ricardo Alfredo Bloch
Andrew James Dalziel Ritchie
Jack Ryer
Original Assignee
Exxon Chemical Patents Inc.
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Publication date
Application filed by Exxon Chemical Patents Inc. filed Critical Exxon Chemical Patents Inc.
Priority to CA002131098A priority Critical patent/CA2131098C/fr
Priority to JP5518519A priority patent/JPH07508771A/ja
Priority to EP93911622A priority patent/EP0649459A1/fr
Publication of WO1993021288A1 publication Critical patent/WO1993021288A1/fr

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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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    • 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
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    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
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    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • This invention relates to lubricating oil compositions which exhibit enhanced fuel economy and which contain a minor amount of the friction modifier combination of a poly fatty acid ester and an alkoxylated. hydrocarbylamine.
  • Another known category of friction modifiers includes alkoxylated hydrocarbyl mono or polyamines such as generally illustrated by formulas 1 and 2 below.
  • These amines include materials such as N,N-bis(2-hydroxyalkyl) hydrocarbyl amines such as disclosed in U.S. Patents 3,711,406, 3,796,662, 3,933,659, 4,010,106, 4,129,508, 4,170,560, 4,231,883 and 4,795,583.
  • Polyol fatty acid esters are also known to impart improved friction properties when added to lube oil compositions.
  • Canadian Patent 1,205,451 discloses the use of a combination of a glycerol partial ester of a C 16 - C 18 fatty acid and an oil soluble organic copper compound in lubricant oils to enhance fuel economy.
  • U.S. Patent 3,933,659 discloses an automatic transmission fluid containing a polyol ester or fatty acid amides as friction modifiers.
  • U.S. Patent 4,304,678 discloses hydroxyl-containing esters, including glycerol oleates, as effective friction modifiers for lubricant oils.
  • the present invention is based on the discovery that a combination of one or more alkoxylated hydrocarbylamines and one or more polyol fatty acid esters, as defined herein, added to lubricating oil compositions in specific proportions imparts a more enhanced friction modifying property to the lubricant than an equivalent quantity of either component alone.
  • the present invention provides an improved lubricating oil composition for automative internal combustion engines and transmissions which comprises an oil of lubricating viscosity having admixed therewith, in addition to conventional additives, a minor amount of friction modifier composition which reduces the coefficient of friction between moving mechanical parts, thereby providing for enhanced fuel ecomony.
  • the friction modifier composition comprises a combination of an alkoxylated hydrocarbyl amine and a polyol partial ester of a saturated or unsaturated fatty acid or a mixture of such esters. This combination of components provides for synergistic fuel ecomony effects, particularly when used as components in automotive crankcase lubricants also containing conventional additive packages, which effects are not observed in oil which contains one or the other of these components alone.
  • alkoxylated amines which are suitable as one component of the friction modifier composition of this invention have the general formula 1:
  • R 1 is a branched or straight chain hydrocarbyl group containing from about 8 to about 30 carbon atoms
  • R 2 and R 3 are independently the same or different branched or straight chain alkylene radicals containing 1 to 6 carbon atoms
  • R 4 R 5 and R 6 are independently the same or different alkylene radicals containing from 2 to 4 carbon atoms
  • X is oxygen or sulfur
  • p is 0 or an integer ranging from 1 to 20
  • t is independently 0 or 1
  • a, b and c are independently integers ranging from 1 to 4.
  • R 1 is a saturated or ethylenically unsaturated hydrocarbyl group containing from 12 to 24 carbon atoms
  • R 2 and R 3 independently contain 2-4 carbon atoms
  • R 4 , R 5 and R 6 independently contain 2 or 3 carbon atoms
  • X is oxygen and a, b and c are independently integers of 1 or 2.
  • both p and t may be 1 or either p or t may be 1 when the other of them is 0, or p may be
  • the alkoxylated amine is a monoamine subgenus of formula 1, where p and t are each 0, having the formula 2:
  • R 1 , R 4 , R 5 , a and b are as set forth above.
  • Illustrative of more preferred alkoxylated amines within the scope of this invention include N,N',N'-tri(2-h ⁇ droxyeth ⁇ l) N-octadecyl propylene diamine, N,N',N'-tri(2-hydroxyethyl) N-octadecenyl propylene diamine, N,N',N'-tri(2-hydroxyethyl) N-hexadecyl propylene diamine, N,N',N'-tri(3-hydroxypropyl) N-octadecadienyl propylene diamine, N,N',N'-tri(2-hydroxyethyl) N-octadecyl ethylene diamine, N,N',N'-tri(2-hydroxyethyl) N-octadecenyl ethylene diamine, N,N',N'-tri(2-hydroxyethyl) N-octadecenyl
  • alkoxylated amines are those of formula 2 and wherein R 4 and R 5 each have 2 carbon atoms and include:
  • the hydroxyl amine compounds may be used as such. However they may also be used in the form of an adduct or reaction product with a boron compound, such as a boric oxide, a boron halide, a metaborate, boric acid, or a mono-, di-, or triorgano borate, such as a mono-, di-, and trialkyl borate.
  • a boron compound such as a boric oxide, a boron halide, a metaborate, boric acid, or a mono-, di-, or triorgano borate, such as a mono-, di-, and trialkyl borate.
  • a boronation agents include boric acid and boric acid esters, e.g., tributyl borate.
  • a stoichiometric amount of the boronating agent relative to the hydroxy groups present in the amine can be used or an excess of boronating agent of up to a 50-100% excess or more can be used and is often desirable for certain applications.
  • boronation can be complete or partial.
  • boronation levels vary from about 0.05 to about 7 weight % of boron in the boronated derivative.
  • the boronated derivatives are prepared in the presence of an alcoholic or hydrocarbon solvent.
  • a solvent is not essential, however. If one is used, it may be reactive or non-reactive.
  • Suitable non-reactive solvents include benzene, toluene, xylene and the like.
  • Suitable reactive solvents include isopropanol, butanol, the pentanols and the like. Reaction temperatures may vary from about 70° to about 250°C with about 110° to about 170°C being preferred.
  • the second essential component of the friction modifier composition of this invention is one or a mixture of esters of a fatty acid having the formula 3 :
  • R 7 represents an alkylene or alkenylene hydrocarbyl radical having from 10 to 18 carbon atoms
  • R 8 is the residuum of a polyhydric alcohol containing from 2 to 5 carbon atoms and from 2 to 4 hydroxyl groups
  • e is 0 or 1
  • d is an integer of 1, 2 or 3.
  • R 7 is an alkylene radi.cal contai.ni.ng 14 to 16 carbon atoms
  • R 8 is the residuum of glycerol
  • e is 0
  • d is 1 or 2.
  • esters are commercially available and may be prepared by forming the esterification product of a fatty acid such as oleic acid, stearic acid, linoleic acid, ricinoleic acid and the like with a suitable polyol such as ethylene glycol, propylene glycoi, glycerol, pentaerythritol and the like by well known esterification processes.
  • a fatty acid such as oleic acid, stearic acid, linoleic acid, ricinoleic acid and the like
  • suitable polyol such as ethylene glycol, propylene glycoi, glycerol, pentaerythritol and the like by well known esterification processes.
  • esters are the partial esters of oleic or ricinoleic acids and glycerol and include glycerol monooleate, glyceroldioleate, glycerolmonoricinoleate, glyceroldiricinoleate and mixtures thereof. Mixtures of glycerol monoleate and glycerol dioleate are most preferred.
  • the base lubricating oil into which the friction modifier composition of this invention may be incorporated includes automotive crankcase and transmission oils of lubricating viscosity for both diesel and gasoline engines, including natural and synthetic lubricating oils and mixtures thereof.
  • Natural oils include animal oils and vegetable oils such as castor oil or lard oil, liquid petroleum oils and hydrorefined oils, solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils.
  • Synthetic lubricating oils include hydrocarbon and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), pol ⁇ (1-decenes); alkylbenezenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl) benzenes); and polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols).
  • hydrocarbon and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylene
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification or etherification constitute another class of known synthetic lubricating oils. These are exemplified by polyoxylalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and include the alkyl and aryl ethers of these polyoxyalkylene polymers such as methyl-polyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of poly-ethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500, and mono-and polycarboxylic esters thereof such as acetic acid esters, mixed C 3 to C 6 fatty acid esters and the C 13 Oxo acid diester of tetraethylene glycol.
  • Another suitable class of synthetic lubricating oils comprises one or more esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids and alkenyl malonic acids) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether and propylene glycol).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, lin
  • esters include dibutyl adipate, di(2-eth ⁇ lhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, dodecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • Esters useful as synthetic oils also include those made from C 5 to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.
  • Silicon-based oils such as the polyalkyl, polyaryl-polyalkoxy-, or polyaryloxysiloxane oils and silicate oils comprise another useful class of synthetic lubricants. These include tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl- 2-ethylhexyl) silicate tetra-(p-tert-butyl-phenyl) silicate, hexa-(4-methyl-2-pentoxy) disiloxane, poly(methyl) siloxanes and poly (methylphenyl) siloxanes.
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
  • Unrefined, refined and rerefined oils can be used in the lubricants of the present invention.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques, such as distillation, solvent extraction, acid or base extraction, filtration and percolation are known to those skilled in the art.
  • Rerefined oils are obtained by processes similar to those used to obtain refined oils, but applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques for removal of spent additives and oil breakdown products.
  • the components of the friction modifier composition of this invention are each blended into the lube oil base stock in amounts which reduce the friction coefficient between the mechanical parts of the engine or other apparatus in which they are used, thereby enhancing fuel economy.
  • the amount of alkoxylated amine added to the base oil will range from about 0.1 to 1.0% by weight, more preferably from about 0.2 to 0.5% by weight.
  • the amount of fatty acid ester added to the base oil will range from about 0.1 to 1.0% by weight, more preferably from about 0.2 to 0.5% by weight.
  • the preferred weight ratio of the alkoxylated amine to the ester is in the range of from about 0.4 to 2.5:1 respectively, more preferably from about 0.75 to 1.5:1 respectively. Most preferably these components are added in approximately equi-weight amounts.
  • the lubricant oil of this invention is preferably also admixed with one or more additional additives to form a fully formulated oil.
  • additional additives include dispersants, detergents, oxidation inhibitors, viscosity modifiers, corrosion inhibitors, other friction modifiers, antifoaming agents, anti wear agents and the like.
  • Suitable dispersants which may be employed are known in the art.
  • a preferred class of dispersant are the ashless dispersants which are normally nitrogen-containing, oil-soluble salts, amides, imides or esters of mono or dicarboxylic acids.
  • a particularly preferred dispersant is the reaction product of a polyolefin-substituted succinic anhydride such as polyisobutenyl succinic anhydride and an alkylene polyamine, which can be further treated with a source of boron or copper.
  • a polyolefin-substituted succinic anhydride such as polyisobutenyl succinic anhydride and an alkylene polyamine, which can be further treated with a source of boron or copper.
  • Such a material is disclosed in U.S. Patent 4,938,880, the complete disclosure of which is incorporated herein by reference.
  • Such dispersants are generally added to the oil in amounts ranging from about 0.1 to about 10% by weight.
  • Metal containing rust inhibitors and/or detergents are frequently used with ashless dispersants.
  • Such detergents and rust inhibitors include the metal salts of sulphonic acids, fatty acid esters such as glycerol mono and/or di stearate (which also function as friction modifiers), alkyl phenols, sulfurized alkyl phenols, alkyl salicylates, naphthenates, and other oil soluble mono- and di-carboxylic acids.
  • Highly basic, that is overbased metal salts, which are frequently used as detergents include calcium or magnesium phenates, sulfurized phenates and/or sulfonates.
  • these metal containing inhibitors and detergents are used in lubricating oil in amounts of about 0.01 to 10 wt.
  • Marine diesel lubricating oils typically employ such metal-containing rust inhibitors and detergents in amounts up to about 20 wt. %.
  • the lube oil may also contain one or more suitable antioxidants and/or oxidation inhibitors.
  • suitable antioxidants include phenols, hindered phenols, bis-phenols, sulfurized phenols, catechol, alkylated and sulfurized alkylated catechols, diphenylamine, alkylated diphenylamines and phenyl-1-naphthlamines, alkyl and aryl borates, phosphites and phosphates, trialkyl and triaryl dithiophosphates and the like.
  • Other antioxidants include oil soluble copper compounds. The copper compound may be in the cuprous and cupric form.
  • the copper may be in the form of copper dihydrocarbyl thio- or dithio-phosphates.
  • the copper may be added as the copper salt of a synthetic or natural carboxylic acid.
  • Examples include C 10 to C 18 fatty acids such as stearic or palmitic.
  • Unsaturated acids such as oleic or branched carboxylic acids such as napththenic acids of molecular weight from 200 to
  • the copper antioxidant can comprise a copper salt of a hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing reaction product, which reaction product is formed by reacting a polymer of a C 2 to C 10 monoolefin having a number average molecular weight of 900 to 1400 (e.g., 700 to 1200) substituted with a C 4 to C 10 monosaturated acid material.
  • Exemplary are copper salts of a hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing reaction product, which reaction product is formed by reacting a polymer of C 2 to C 10 monoolefin having a number average molecular weight of from 900 to 1400 substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups, wherein there is an average of about 0.8 to 1.6 molar proportions of succinic moieties per molar proportion of the polymer.
  • the copper antioxidants will generally be added to the oil in an amount of from about 50-500 ppm by weight of the metal.
  • Corrosion inhibitors also known as anti-corrosive agents, reduce the degradation of the metallic parts contacted by the lubricating oil composition.
  • Illustrative of corrosion inhibitors are phosphosulfurized hydrocarbons and the products obtained by reaction of a phosphosulfurized hydrocarbon with an alkaline earth metal oxide or hydroxide, preferably in the presence of an alkylated phenol or of an alkylphenol thioester, and also preferably in the presence of carbon dioxide.
  • Phosphosulfurized hydrocarbons are prepared by reacting a suitable hydrocarbon such as a terpene, a heavy petroleum fraction of a C 2 to C 6 olefin polymer such as polyisobutylene, with from 5 to 30 weight percent of a sulfide of phosphorus for 0.5 to 15 hours, at a temperature in the range of 150° to 600°C. Neutralization of the phosphosulfurized hydrocarbon may be effected in the manner taught in U.S. Patent 1,969,324.
  • Oxidation inhibitors reduce the tendency of mineral oils to deteriorate in service which deterioration can be evidenced by the products of oxidation such as sludge and varnish-like deposits on the metal surfaces and viscosity growth.
  • oxidation inhibitors include alkaline earth metal salts of alkylphenolthioesters having preferably C 5 to C 12 alkyl side chains, calcium nonylphenol sulfide, barium t-octylphen ⁇ l sulfide, dioctylphenylamine, phenylalphanaphthylamine, phosphosulfurized or sulfurized hydrocarbons, etc.
  • Pour point depressants lower the temperature at which the oil will flow or can be poured. Such depressants are well known. Typical of those additives which usefully optimize the low temperature fluidity of the oil are C 8 -C 18 dialkylfumarate/vinyl acetate copolymers, polymethacrylates, and wax napthalene.
  • Foam control can be provided by an antifoamant of the polysiloxane type, e.g. silicone oil and polydimethyl siloxane.
  • an antifoamant of the polysiloxane type e.g. silicone oil and polydimethyl siloxane.
  • dihydrocarbyl dithiophosphate metal salts which are frequently used as anti-wear agents and which also provide antioxidant activity. These compounds may be generally characterized by the formula
  • R 9 and R 10 are each independently hydrocaryl groups containing from 3 to about 13 carbon atoms, M is a metal and n is an integer equal to the valence of M.
  • the hydrocarbyl groups in the phosphorodithioate structure include alkyl, cycloalkyl or alkaryl groups which may contain ether or ester linkages and which may also contain substituent groups such as halogen or nitro.
  • Illustrative alkyl groups include isopropyl, isobutyl, n-butyl, sec-but ⁇ l, amyl, n-hexyl, methylisobutyl carbinyl, heptyl, 2-ethylhex ⁇ l, diisobutyl, isooctyl, nonyl, behenyl, decyl, dodecyl, tridecyl, etc.
  • Illustrative lower alkylphenyl groups include xylyl, cresyl, butylphenyl, amylphenyl, heptyl-phenyl, etc.
  • Cycloalkyl groups likewise are useful and these include chiefly cyclohexyl and the lower alkyl-cyclohexyl radicals. Many substituted hydrocarbon groups may also be used, e.g., chloropentyl, dichlorophenyl, and dichlorodecyl.
  • These compounds are prepared by first forming the relevant phosphorodithioic acid and then reacting this product with a suitable metal containing compound.
  • the phosphorodithioic acids are prepared by the reaction of phosphorus pentasulfide with an alcohol or phenol or mixtures of alcohols, mixtures of phenols or mixtures of alcohols and phenols.
  • the reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide, and may be carried out within the temperature range from about 50°C to about 200°C, preferably from about 50°C to about 150°C.
  • the preparation of O,O-di-n-hexyl phosphorodithioic acid involves the reaction of phosphorus pentasulfide with four moles of n-hexyl alcohol at about 100°C for about two hours.
  • Hydrogen sulfide is liberated and the residue is the defined acid.
  • the preparation of the metal salt of this acid may be effected by reaction with metal oxide. Simply mixing and heating these two reactants is sufficient to cause the reaction to take place and the resulting product is sufficiently pure for the purposes of this invention.
  • the metal salts of dihydrocarbyl phosphorodithioates which are useful in this invention include those salts containing Group I metals, Group II metals, aluminum, lead, tin, manganese, cobalt, and nickel.
  • the Group II metals, tin, iron, cobalt, lead, manganese, nickel and copper are among the preferred metals. Zinc and copper are especially useful metals.
  • metal compounds which may be reacted with the acid include lithium oxide, lithium hydroxide, sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, silver oxide, magnesium oxide, magnesium hydroxide, calcium oxide, zinc hydroxide, zinc oxide, copper oxide, strontium hydroxide, cadmium oxide, cadmium hydroxide, barium oxide, iron carbonate, copper hydroxide, lead hydroxide, tin butylate, cobalt hydroxide, nickel hydroxide, nickel carbonate and the like.
  • the incorporation of certain ingredients such as small amounts of the metal acetate or acetic acid in conjunction with the metal reactant will facilitate the reaction and result in an improved product.
  • certain ingredients such as small amounts of the metal acetate or acetic acid in conjunction with the metal reactant
  • the use of up to about 5% of zinc acetate in combination with the required amount of zinc oxide facilitates the formation of a zinc phosphorodithioate.
  • the alkyl groups R 9 and R 10 in the formula above are derived from secondary alcohols such as isopropyl alcohol, secondary butyl alcohol, 2-pentanol, 4-methyI-2-pentanol, 2-hexanol, 3-hexanol, as well as mixtures thereof.
  • These compounds are generally incorporated into the lubricating oil formulation in the range of from about 0.01 to about 5% by weight, more preferably from about 0.1 to about 3% by weight.
  • the preferred compounds are the zinc dihydrocarbyl dithiophosphites.
  • Viscosity modifiers impart high and low temperature operability to the lubricating oil and permit it to remain relatively viscous at elevated temperatures and also exhibit acceptable viscosity or fluidity at low temperatures.
  • Viscosity modifiers are generally high molecular weight polymers, including polyesters, polymethacrylates, polyacrylates and polyolefins. The viscosity modifiers may also be derivatized to include other properties or functions, such as the addition of dispersancy properties.
  • These oil soluble viscosity modifying polymers will generally have number average molecular weights of from 10 3 to 10 6 , preferably 10 4 to 10 6 , e.g., 20,000 to 250,000, as determined by gel permeation chromotography or osmometry.
  • suitable hydrocarbon polymers include homopolymers and copolymers of two or more C 2 to C 30 olefin monomers, e.g. C 2 to C 8 olefins, including both alpha olefins and internal olefins, which may be straight or branched, aliphatic, aromatic, alkyI-aromatic, cycloaliphatic, etc.
  • Particularly preferred polymers are polyisobutylenes, homopolymers and copolymers of C 2 and higher alpha olefins, atactic polypropylene, hydrogenated polymers and copolymers and terpolymers of styrene, e.g. with isoprene and/or butadiene and hydrogenated derivatives thereof.
  • the polymer may be degraded in molecular weight, for example by mastication, extrusion, oxidation or thermal degradation, and may contain oxygen.
  • These viscosity modifiers are normally added to the oil composition at a level within the range of from about 0.1 to about 10% by weight.
  • additives which serves to stabilize the compatibility of lubricant compositions containing relatively high levels of friction modifiers.
  • additives include hydrocarbyl substituted succinic anhydrides, more preferably polyolefin-substituted succinic anhydride wherein the polyolefin has a number average molecular weight of from about 500 to 10,000, more preferably from about 1000 to 3000.
  • Preferred polyolefin substituent groups include polyisobutylene, polybutene-1, as well as copolymers of butene-1 with ethylene and/or propylene.
  • Polyisobutyenyl succinic anhydride is a preferred compatibilizer for this purpose.
  • This ingredient may be present in the lubricant composition at a level within the range of about 0.1 to 5% by weight, and is preferably present at about the same level as the total weight of friction modifier additives.
  • Compositions which contain one or more of these numerous additives are typically blended by physical admixture into the lube oil in amounts effective to provide their normal attendant function.
  • compositions within the scope of this invention can be demonstrated using what is referred to as a Sequence VI Dynanometer Fuel economy test, more specifically described as the ASTM Sequence VI test method RR: DO-2: 1204. This test is run using a 3.8 liter Buick V-6 engine equipped with cooling means to maintain a relatively constant engine oil temperature of 150oF or 275oF, coupled to a power absorbing dynanometer such that the engine speed and power output can be tightly controlled.
  • the lubricant to be evaluated is first flushed into the engine and aged at an oil temperature of 225 deg. F for 32 hours.
  • the engine is then set to a specific speed and power output, and the test is conducted at the temperature for the two test stages of 150 deg. F and 275 deg. F.
  • the engine is calibrated prior to each candidate run, using industry standard viscosity and friction modified reference oils. At each stage the average brake specific consumption is calculated.
  • the lubricant in the engine is detergent flushed then flushed to an SAE 30 baseline oil and the measurements are repeated. These measurements are then used to calculate the Equivalent Fuel Economy Improvement (EFEI) of the candidate relative to the baseline oil.
  • EFEI Equivalent Fuel Economy Improvement
  • a base control SAE 10W-30 formulation was prepared by mixing about 94 parts by volume of mineral oil with effective amounts of the following additive ingredients to total 100 parts: a) - Polybutenyl succinic anhydride polyamine product (borated);
  • Example 1 Control formulation + 0.5% V. glycerol oleate esters
  • Example 2 Control formulation + 0.5% V. N,N-bis
  • Example 3 Control formulation + 0.25% V. glycerol oleate esters + 0.25% V. N,N-bis (2-hydroxyethyl) tallow amine.
  • test results show that each of the glycerol oleate mixtures and N,N-bis (2-hydroxyethyl) tallow amine exhibit enhanced fuel efficiency in the base formulation when added to the control formulation at a 0.5% by volume concentration, with the N,N-bis (2-hydroxyethyl) tallow amine being somewhat superior.
  • Example 4 Control formulation + 0.25% V. N,N-bis
  • Example 5 Control formulation + 0.5% V. N,N-bis

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Abstract

Composition d'huile lubrifiante améliorée destinée à des systèmes de transmission et des moteurs thermiques d'automobiles, constituée d'une huile possédant une viscosité permettant la lubrification, dans laquelle on a ajouté et mélangé une faible quantité d'une composition d'agents modifiant le frottement qui réduit le coefficient de frottement entre des en pièces mécaniques en mouvement et produit une économie de carburant plus importante. La composition d'agents modifiant le frottement comprend un mélange d'une amine hydrocarbyle alcoxylée et d'un ester partiel de polyol d'un acide gras saturé ou non saturé ou un mélange de ces esters, chacun de ces éléments étant préférablement présent dans une proportion comprise entre environ 0,1 et environ 1,0 % en poids sur la base du poids de l'huile. Cette association de constituants produit plus particulièrement des effets synergiques sur l'économie de carburant lorsqu'on les utilise comme composants dans des lubrifiants de carters-moteurs d'automobiles contenant également des additifs classiques; ces effets n'apparaissant pas avec de l'huile ne renfermant qu'un seul de ces composants.
PCT/US1993/003381 1992-04-15 1993-04-09 Composition de lubrifiant contenant un melange d'agents modifiant le frottement WO1993021288A1 (fr)

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CA002131098A CA2131098C (fr) 1992-04-15 1993-04-09 Composition lubrifiante contenant un melange de modificateurs de friction
JP5518519A JPH07508771A (ja) 1992-04-15 1993-04-09 混合摩擦調整剤を含有する潤滑油組成物
EP93911622A EP0649459A1 (fr) 1992-04-15 1993-04-09 Composition de lubrifiant contenant un melange d'agents modifiant le frottement

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0652279A1 (fr) * 1993-06-07 1995-05-10 Ethyl Corporation Economie de carburant et inhibition de l'oxydation dans des compositions lubrifiantes pour moteurs à combustion interne
WO1999018175A1 (fr) * 1997-10-03 1999-04-15 Infineum Usa Lp Compositions lubrifiantes
WO2002079353A1 (fr) * 2001-03-29 2002-10-10 The Lubrizol Corporation Composition d'additif d'essence concentre, compositions de carburant et procede connexe
EP1418353A2 (fr) * 2002-11-06 2004-05-12 Nissan Motor Company, Limited Dispositif de glissement à faible frottement
GB2402942A (en) * 2003-05-29 2004-12-22 Nissan Motor Cutting oil composition for machine tool
EP1510594A2 (fr) * 2003-08-21 2005-03-02 Nissan Motor Co., Ltd. Organe de guidage glissant à bas coefficient de frottement et dispositif de glissement à faible frottement l'incorporant
SG131759A1 (en) * 2002-05-22 2007-05-28 Chevron Oronite Co Lubricating compositions for friction material interfaces
WO2011161406A1 (fr) 2010-06-25 2011-12-29 Castrol Limited Utilisations et compositions
WO2012025901A1 (fr) 2010-08-27 2012-03-01 Total Raffinage Marketing Lubrifiant moteur
WO2012056191A1 (fr) 2010-10-26 2012-05-03 Castrol Limited Compositions de carburant et de lubrifiant non aqueuses comprenant des esters d'acides gras d'acides hydroxycarboxyliques et leurs utilisations
WO2012168151A1 (fr) 2011-06-09 2012-12-13 Castrol Limited Compositions, procédés et utilisations
WO2013098354A1 (fr) * 2011-12-27 2013-07-04 Shell Internationale Research Maatschappij B.V. Huile pour moteur destinée à des véhicules motorisés
CN103314090A (zh) * 2010-11-24 2013-09-18 雪佛龙奥伦耐有限责任公司 包含摩擦调节剂共混物的润滑油组合物
WO2013189674A1 (fr) 2012-06-20 2013-12-27 Castrol Limited Modificateur de frottement et son utilisation dans des lubrifiants et des carburants
WO2013189675A1 (fr) 2012-06-20 2013-12-27 Castrol Limited Modificateurs de friction et leur utilisation dans des lubrifiants et des carburants
EP2735604A1 (fr) 2012-11-22 2014-05-28 Castrol Limited Procédé de préparation d'une composition de lubrifiant
CN111315852A (zh) * 2017-11-09 2020-06-19 禾大国际股份公开有限公司 包含摩擦调节剂的润滑油制剂
US10907111B2 (en) 2015-02-06 2021-02-02 Castrol Limited Use of a hydrocarbyl-substituted salicylic acid detergent as an inhibitor of lead corrosion
WO2021064059A1 (fr) 2019-10-02 2021-04-08 Castrol Limited Additifs anti-usure au phosphore non métalliques
US10982166B2 (en) 2015-02-06 2021-04-20 Castrol Limited Use of a boron-containing additive as an inhibitor of lead corrosion

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JP4511154B2 (ja) * 2003-11-11 2010-07-28 新日本石油株式会社 エンジン油用潤滑油組成物
JP2009126868A (ja) * 2007-11-19 2009-06-11 Adeka Corp 潤滑油添加剤組成物及びそれを含有する潤滑油組成物
US9029304B2 (en) * 2008-09-30 2015-05-12 Chevron Oronite Company Llc Lubricating oil additive composition and method of making the same
FR2974111B1 (fr) * 2011-04-14 2013-05-10 Total Raffinage Marketing Lubrifiant cylindre pour moteur marin deux temps
WO2014136906A1 (fr) * 2013-03-06 2014-09-12 Ｊｘ日鉱日石エネルギー株式会社 Modificateur de frottement et composition d'huile lubrifiante
JP6780826B2 (ja) * 2017-03-16 2020-11-04 出光興産株式会社 潤滑油組成物及び内燃機関の摩擦低減方法

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EP0652279A1 (fr) * 1993-06-07 1995-05-10 Ethyl Corporation Economie de carburant et inhibition de l'oxydation dans des compositions lubrifiantes pour moteurs à combustion interne
WO1999018175A1 (fr) * 1997-10-03 1999-04-15 Infineum Usa Lp Compositions lubrifiantes
US6844301B2 (en) 1997-10-03 2005-01-18 Infineum Usa Lp Lubricating compositions
WO2002079353A1 (fr) * 2001-03-29 2002-10-10 The Lubrizol Corporation Composition d'additif d'essence concentre, compositions de carburant et procede connexe
SG131759A1 (en) * 2002-05-22 2007-05-28 Chevron Oronite Co Lubricating compositions for friction material interfaces
EP1418353A2 (fr) * 2002-11-06 2004-05-12 Nissan Motor Company, Limited Dispositif de glissement à faible frottement
EP1418353A3 (fr) * 2002-11-06 2005-06-29 Nissan Motor Company, Limited Dispositif de glissement à faible frottement
GB2402942B (en) * 2003-05-29 2006-05-24 Nissan Motor Hard-carbon coated machine tool and cutting oil composition therefor
GB2402942A (en) * 2003-05-29 2004-12-22 Nissan Motor Cutting oil composition for machine tool
EP1510594A3 (fr) * 2003-08-21 2006-04-26 Nissan Motor Co., Ltd. Organe de guidage glissant à bas coefficient de frottement et dispositif de glissement à faible frottement l'incorporant
EP1510594A2 (fr) * 2003-08-21 2005-03-02 Nissan Motor Co., Ltd. Organe de guidage glissant à bas coefficient de frottement et dispositif de glissement à faible frottement l'incorporant
WO2011161406A1 (fr) 2010-06-25 2011-12-29 Castrol Limited Utilisations et compositions
US9080120B2 (en) 2010-06-25 2015-07-14 Castrol Limited Uses and compositions
WO2012025901A1 (fr) 2010-08-27 2012-03-01 Total Raffinage Marketing Lubrifiant moteur
WO2012056191A1 (fr) 2010-10-26 2012-05-03 Castrol Limited Compositions de carburant et de lubrifiant non aqueuses comprenant des esters d'acides gras d'acides hydroxycarboxyliques et leurs utilisations
US9828564B2 (en) 2010-10-26 2017-11-28 Castrol Limited Non-aqueous lubricant and fuel compositions comprising fatty acid esters of hydroxy-carboxylic acids, and uses thereof
US9127232B2 (en) 2010-10-26 2015-09-08 Castrol Limited Non-aqueous lubricant and fuel compositions comprising fatty acid esters of hydroxy-carboxylic acids, and uses thereof
US8703680B2 (en) 2010-11-24 2014-04-22 Chevron Oronite Company Llc Lubricating composition containing friction modifier blend
EP2643440A4 (fr) * 2010-11-24 2013-10-23 Chevron Oronite Co Composition lubrifiante contenant mélange de modificateur de frottement
EP2643440A2 (fr) * 2010-11-24 2013-10-02 Chevron Oronite Company LLC Composition lubrifiante contenant mélange de modificateur de frottement
CN103314090A (zh) * 2010-11-24 2013-09-18 雪佛龙奥伦耐有限责任公司 包含摩擦调节剂共混物的润滑油组合物
WO2012168151A1 (fr) 2011-06-09 2012-12-13 Castrol Limited Compositions, procédés et utilisations
WO2013098354A1 (fr) * 2011-12-27 2013-07-04 Shell Internationale Research Maatschappij B.V. Huile pour moteur destinée à des véhicules motorisés
WO2013189674A1 (fr) 2012-06-20 2013-12-27 Castrol Limited Modificateur de frottement et son utilisation dans des lubrifiants et des carburants
WO2013189675A1 (fr) 2012-06-20 2013-12-27 Castrol Limited Modificateurs de friction et leur utilisation dans des lubrifiants et des carburants
EP2735604A1 (fr) 2012-11-22 2014-05-28 Castrol Limited Procédé de préparation d'une composition de lubrifiant
US10907111B2 (en) 2015-02-06 2021-02-02 Castrol Limited Use of a hydrocarbyl-substituted salicylic acid detergent as an inhibitor of lead corrosion
US10982166B2 (en) 2015-02-06 2021-04-20 Castrol Limited Use of a boron-containing additive as an inhibitor of lead corrosion
CN111315852A (zh) * 2017-11-09 2020-06-19 禾大国际股份公开有限公司 包含摩擦调节剂的润滑油制剂
WO2021064059A1 (fr) 2019-10-02 2021-04-08 Castrol Limited Additifs anti-usure au phosphore non métalliques

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CA2131098A1 (fr) 1993-10-16
MX9302129A (es) 1994-06-30
EP0649459A1 (fr) 1995-04-26
AU4048793A (en) 1993-11-18
CA2131098C (fr) 1999-07-06

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