EP0649459A1 - Composition de lubrifiant contenant un melange d'agents modifiant le frottement - Google Patents

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

Info

Publication number
EP0649459A1
EP0649459A1 EP93911622A EP93911622A EP0649459A1 EP 0649459 A1 EP0649459 A1 EP 0649459A1 EP 93911622 A EP93911622 A EP 93911622A EP 93911622 A EP93911622 A EP 93911622A EP 0649459 A1 EP0649459 A1 EP 0649459A1
Authority
EP
European Patent Office
Prior art keywords
composition
carbon atoms
oil
amine
weight
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.)
Withdrawn
Application number
EP93911622A
Other languages
German (de)
English (en)
Inventor
Ricardo Alfredo Bloch
Andrew James Dalziel Ritchie
Jack Ryer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Chemical Patents Inc
Original Assignee
Exxon Chemical Patents Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Exxon Chemical Patents Inc filed Critical Exxon Chemical Patents Inc
Publication of EP0649459A1 publication Critical patent/EP0649459A1/fr
Withdrawn legal-status Critical Current

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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
    • 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
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • 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
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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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
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
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    • C10M159/12—Reaction products
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    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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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
    • 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 is a branched or straight chain hydrocarbyl group containing from about 8 to about 30 carbon atoms
  • R 2 and R3 are independently the same or different branched or straight chain alkylene radicals containing 1 to 6 carbon atoms
  • R 4 R 5 and R6 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 .
  • R is a saturated or ethylenically unsaturated hydrocarbyl group containing from 12 to
  • both p and t may be 1 or either p or t may be l 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 , R , R , a and b are as set forth above.
  • R is a saturated or ethylenically unsaturated hydrocarbyl group having from 12 to 24 carbon. atoms, particularly a group derived from tallow amine, oleyl amine, stearyl amine, lauryl amine, behynyl amine and the like as
  • Illustrative of more preferred alkoxylated amines within the scope of this invention include 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-hexadecy1 propylene diamine r 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
  • R 4. and R 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 etaborate, 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 etaborate, 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 stoichio etric 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 represents an alkylene or alkenylene hydrocarbyl radical having from 10 to 18 carbon
  • R 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 and d is an integer of 1, 2 or 3.
  • R 7 is an alkylene radi.cal contai.ni.ng 14 to 16 a carbon atoms, R is the residuum of glycerol, e is 0 and 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 r polypropylenes, propylene-isobutylene copolymers, chlorinated ' polybutylenes, poly(1-hexenes) , poly(1-octenes) , pol ⁇ (l-decenes) ; alkylbenezenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl) benzenes) ; and polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols) .
  • polymerized and interpolymerized olefins e.g., polybutylenes r polypropylenes, prop
  • 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.
  • polyoxylalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
  • alkyl and aryl ethers of these polyoxyalkylene polymers such as methyl-polyisopropylene
  • 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, alonic 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,
  • 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_ to C _ monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, tri ethylolpropane, pentaerythritol, dipenta- erythritol 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.
  • metal containing inhibitors and detergents are used in lubricating oil in amounts of about 0.01 to 10 wt. %, more preferably about 0.1 to 5 wt. %, based on the weight of the total lubricating composition.
  • 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 1Q 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. to C. monounsatur ted dicarboxylic acid producing reaction product, which reaction product is formed by reacting a polymer of a C- 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 C1.0_ monosaturated acid material.
  • Exemplary are copper salts of a hydrocarbyl substituted C 4 to C 1Q monounsaturated dicarboxylic acid producing reaction product, which reaction product is formed by reacting a polymer of C, to C.- 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_ to C_ 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 to C._ 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 3 ⁇ G R 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 R10 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 r 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 0,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" and R 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 to C- olefin monomers, e.g. C_ to C 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_ 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. 22
  • 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 150 F or 275 F, 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:
  • 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, -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 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.
EP93911622A 1992-04-15 1993-04-09 Composition de lubrifiant contenant un melange d'agents modifiant le frottement Withdrawn EP0649459A1 (fr)

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MX9302129A (es) 1994-06-30
CA2131098C (fr) 1999-07-06
JPH07508771A (ja) 1995-09-28
AU4048793A (en) 1993-11-18
WO1993021288A1 (fr) 1993-10-28
CA2131098A1 (fr) 1993-10-16

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