EP0092946A2 - Glycerolester mit öllöslichen Kupferverbindungen als Kraftstoffzusatzmittel für wirtschaftlichere Ausnutzung - Google Patents

Glycerolester mit öllöslichen Kupferverbindungen als Kraftstoffzusatzmittel für wirtschaftlichere Ausnutzung Download PDF

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Publication number
EP0092946A2
EP0092946A2 EP83302155A EP83302155A EP0092946A2 EP 0092946 A2 EP0092946 A2 EP 0092946A2 EP 83302155 A EP83302155 A EP 83302155A EP 83302155 A EP83302155 A EP 83302155A EP 0092946 A2 EP0092946 A2 EP 0092946A2
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European Patent Office
Prior art keywords
oil
fuel economy
copper
glycerol
composition
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Granted
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EP83302155A
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English (en)
French (fr)
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EP0092946A3 (en
EP0092946B1 (de
Inventor
Phillip William Brewster
Clinton Richard Smith
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Publication of EP0092946A3 publication Critical patent/EP0092946A3/en
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Publication of EP0092946B1 publication Critical patent/EP0092946B1/de
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—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
    • 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
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2223/042—Metal salts thereof
    • 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
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11

Definitions

  • British Application 2097813A published November 10, 1982, discloses the use of 0.05 to 0.2 wt% glycerol partial esters of C 16 -C 18 fatty acids as fuel economy additives.
  • the present invention is an improvement over said British application.
  • West German Application P-2949940 and P-2949910 of Chevron Research Company both published July 3, 1980, disclose the use of glycerol fatty esters as fuel economy additives. These references state that the addition of 0.25 to 2 weight percent, preferably 0.40 to 1.25 weight percent, of a fatty acid ester will offer a fuel economy credit of 2-3 percent in both gasoline and diesel engines. Glycerol oleic acid esters are preferred.
  • West German Application P-2949940 illustrates the preferred embodiment showing the use of the glycerol ester at the same treat level in combination with zinc dihydrocarbyl dithiophosphate additives.
  • U.S. Patent 4,304,678 discloses hydroxyl-containing esters including glycerol oleates as being effective friction modifiers only at levels of 1-4 wt% with no benefit observed at levels less than 1% by wt. in oil.
  • the present invention is based upon the discovery that very low levels of glycerol esters; that is, up to about 0.2 percent by weight, in combination with certain amounts of oil-soluble organic copper compounds, provide enhanced performance of these fuel economy lubricating oils. No benefit is obtainable in using relatively higher amounts and in some cases substantial debits in terms of formulation stability or adverse performance may occur.
  • U.S. Patent 3,933,659 shows a multi-component functional fluid, one component of which can be a polyol ester friction modifier or a fatty acid amide friction modifier.
  • the primary use disclosed in that reference is for automatic transmission fluids.
  • U.S. Patent 3,273,981 discloses antiwear additives comprising a mixture of dimer acids and a partial ester of a polyhydric alcohol, the additive being noted as improving lubricity as well as functioning in the anti-wear category.
  • U.S. Patent 3,112,271 discloses glycerol mono-oleate as an extreme pressure additive as does U.S. 3,112,269 and U.S. 3,041,284.
  • U.S. 2,493,483 discloses marine engine lubricants which contain a partial ester of glycerol or other polyol fatty acid esters in amounts of from 0.05 to 1 percent.
  • oil-soluble copper compounds at levels of about 5 to 500 parts per million (ppm) of copper by weight, based on the total weight of lubricating oil composition,as a highly effective antioxidant is a relatively recent development of additive technology and is disclosed in European Published Application No. 0024146, published on February 25, 1981.
  • fuel economy improving lubricating oil compositions for internal combustion engines which comprise an oil of lubricating viscosity and, as the fuel economy additive, a combination from 0.05 to 0.20 weight percent of a glycerol partial ester of a C 16 -C 18 fatty acid with from 5 to 500 ppm (parts per million) copper present in the form of an oil-soluble copper compound, preferably about 60 to 200 ppm copper being present, based upon the weight of the total composition, the copper compound also functioning as an antioxidant.
  • the lubricating oil compositions of the present invention comprise both straight grade and multigrade lubricating oil formulations for both gasoline and diesel (compression ignition) engines.
  • the lubricating oil compositions will contain those additive systems formulated to meet the viscosity requirements or other specifications as required for qualification as a gasoline engine or diesel lubricating oil.
  • a straight grade lubricating oil formulation will normally contain conventional amounts of an ashless dispersant, a normal or basic metal detergent, an anti-wear additive and an antioxidant and a multi-grade oil will contain, in addition to the foregoing, a viscosity index improver or viscosity modifier.
  • very small proportions of other special purpose additives such as pour depressants, rust inhibitors, anti-foamants and the like are conventionally blended into lubricating oil compositions.
  • the ester component of the fuel economy additive of the present invention is preferably a glycerol mono- or diester of a saturated or unsaturated C 16 -C 18 fatty acid, such as oleic or linoleic acid.
  • Optimum efficiency has been found to be at about the 0.1 to 0.2 weight percent level and use in the excess of this amount may even be detrimental to the overall performance of the lubricating oil composition.
  • Oil-soluble copper components useful herein include both cuprous or cupric compounds which are oil-soluble under normal blending conditions in the oil additive package. Particularly preferred are the copper salts of C 10 -C 22 fatty acids, such as stearic or palmitic acid, but copper salts of unsaturated acids, such as oleic acid, linoleic acid, naphthenic acid of 200-500 molecular weight or synthetic carboxylic acids are preferred.
  • the particularly preferred embodiment is copper (cupric) oleate when present in an amount to provide about 100 to 150 ppm copper in the lubricating oil composition.
  • Crankcase oil formulations to which the present invention relates are those which contain a major amount of lubricating oil and effective amounts of conventional additives in addition to the aforesaid fuel economy additive, the copper compound serving the dual function of being both an antioxidant and, in combination with the glycerol oleate, a fuel economy additive.
  • Percentages of additives as described herein are by weight based on the total weight of lubricating oil formulation unless otherwise indicated.
  • Detergents useful in the formulations include the normal, basic or overbased metal, that is, calcium, magnesium and so forth, salts of petroleum naphthenic acids, petroleum sulfonic acids, alkyl benzene sulfonic acids, alkyl phenols, alkylene-bis-phenol, oil-soluble fatty acids and the like.
  • the preferred materials are the normal or overbased calcium or magnesium phenates, sulfurized phenates and/or sulfonates, and these metal-containing detergent additives are typically used in amounts of from 1 to 3 wt % based on the total weight of lubricating oil compositions.
  • Suitable pour point depressants which are usually present in amounts of about 0.01 to 1 wt.%, include wax alkylated aromatic hydrocarbons, olefin polymers and copolymers, acrylate and methacrylate polymers and copolymers.
  • Anti-wear additives generally are the oil-soluble zinc dihydrocarbyl dithiophosphates having a least a total of 5 carbon atoms, the alkyl group being preferably C 2 -C S . These are typically present in amounts of from 0.01 to 5 wt. %, preferably 0.5 to 1.5 wt. %, in the lubricating oil.
  • Suitable conventional viscosity index improvers, or viscosity modifiers are the 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 or alkyl methacrylates, copolymers of alkylmethacrylates with N-vinyl pyrrolidone 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- reacted with alcohols and amines and the like. These additives are used in amounts of about 1.5% to 15% by wt., depending on the exact viscosity specifications desired.
  • antioxidants include phenols, hindered phenols, bis-pheno1s, sulfurized phenols, catechol, alkylated and sulfurized alkylated catechols, diphenylamine, alkylated diphenylamines and phenyl-l-naphthylamines, alkyl and aryl borates, phosphites and phosphates, trialkyl and triaryl dithiophosphates and the like.
  • Suitable hydrocarbon base stocks are those mineral oils of lubricating viscosity as measured by ASTM D-455 of from about 2 to 40, preferably 5 to 20 centistokes at 99 0 C.
  • the reference oil used in this example was a formulated straight grade 20W30 crankcase mineral lubricating oil (corresponding to ASTM "HR" oil) to which was added 0.2 weight percent of a glycerol monooleate (GMO) fuel economy additive or 0.2 weight percent of a fuel economy additive being a mixture (GMO/GDO) of glycerol monooleate and glycerol dioleate in a weight ratio of 3 parts of GMO to 2 parts of GDO in said mixture.
  • the reference oil contained 2.10 wt % dispersant, 1.10 wt. % antioxidant, 1.00 wt. % basic metal detergent, 1. 95 wt.
  • results are expressed as a percentage fuel economy credit with respect to the referenced oil, as are all fuel economy credit results reported in the Examples.
  • Results at the 0.2 wt. % treat level for both GMO and the GMO/GDO mixture are set forth in Table I.
  • Example 1 The Laboratory Fuel Economy Test of Example 1 was repeated utilizing a 10W40 multigrade mineral oil containing 0.09 wt. % of the GMO/GDO mixture as the fuel economy additive.
  • the oil contained about 14% by wt. of a multifunctional dispersant viscosity index improver (acryloid 1155), 0.5% dispersant, 1.85% of basic metal detergent, 0.75 wt.% of anti-wear additive and 0.75% antioxidant.
  • Table III shows the fuel economy credits over the oil used as the reference in Example 1. Laboratory Fuel economy results were confirmed in the Proposed ASTM 5 Car Interim Fuel Economy Procedure which utilized the EPA car certification cycle in 5 automobiles having engine sizes of 2.3 liter, 2.8 liter, 3.7 liter, 3.8 liter and 5.0 liter. Five Car average fuel economy credit of 1.64% was obtained in one series of fuel economy tests.
  • Example 6 This will be demonstrated in Example 6.
  • Example 1-4 and 6 are presented here to illustrate these principles.
  • the LEFET test was carried out using an Oil * equivalent to the HR straight grade oil of Example 1 except that 0.3 wt. % of a 40 wt% solution of copper oleate in mineral oil, which is equivalent to 120 ppm copper was used in place of the anti- oxidant reported in Example 1.
  • the LEFET results for this test are below in Table IV:
  • oils containing both the oil-soluble organic copper compound and glycerol ester friction modifier would exhibit any complementary effect
  • different oils were formulated and tested in Ford 2.3 liter 4-cylinder engine.
  • the purpose of these tests was to evaluate the increase in fuel economy credits when the copper compound and the glycerol ester were combined over the credits obtained with these additives separately in the same engine.
  • Fuel economy credit values will vary among engines of differing sizes. This is due to the inherent differences in engine design and operating conditions. It is known therefore that the values for a 2.3 liter 4-cylinder engine will be lower than fuel economy credit values for a 5 liter 8-cylinder used in these examples.
  • balance is basestock mineral oil.
  • Oil D represents the advantage of this invention. Oils B, C, E show the maximum values one can expect to obtain based on the credits due only to the copper compound. Oil D, however, achieves a value of 0.9%. This result is not expected because it is known, as a general principle, that merely increasing the treatment level of a given fuel economy additive does not increase the credit obtained.
  • Oil G was a formulated lubricating oil having 4 wt% dispersant, 1 wt% overbased metal sulfonate, 1.5 wt% antioxidant and 2 wt% anti-wear additive.
  • Oil H was the same as Oil G , except for the inclusion of 0.1 wt% dimerized linoleic acid ester of diethylene glycol as disclosed in U.S. Patent 4, 105, 571.
  • Oil I was the same as Oil G except 0.2 wt% of the GMO/GDO ester was added.
  • Oil J was the same as Oil G except both 0.1 wt% of the dimerized linoleic acid ester and 0.2 wt% of the GMO/GDO were added. Fuel economy results for these four oils are shown below in Table V I .
  • Oil K contained 5.5 wt% dispersant, 1 wt% overbased metal sulfonate, 1.4 wt% anti-wear additive and 1 wt% anti-oxidant.
  • Oil L was the same as Oil K with .0.3 wt% of a 40 wt% solution of copper oleate (120 ppm copper) included and Oil M was the same as Oil L except 0.1 wt% of the GMO/GDO glycerol oleate was included.
  • Fuel economy credits are in Table VII below.

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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)
  • Liquid Carbonaceous Fuels (AREA)
EP83302155A 1982-04-22 1983-04-15 Glycerolester mit öllöslichen Kupferverbindungen als Kraftstoffzusatzmittel für wirtschaftlichere Ausnutzung Expired EP0092946B1 (de)

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Cited By (28)

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Publication number Priority date Publication date Assignee Title
FR2505355A1 (fr) * 1981-05-06 1982-11-12 Exxon Research Engineering Co Composition d'huile lubrifiante contenant un ester partiel de glycerol
EP0260863A3 (de) * 1986-09-15 1989-02-15 Exxon Research And Engineering Company Schmieröl
EP0280579A3 (en) * 1987-02-27 1989-03-15 Exxon Chemical Patents Inc. Low phosphorus/low zinc lubricants
EP0294045A3 (en) * 1987-05-11 1989-03-22 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
FR2634780A1 (fr) * 1988-08-01 1990-02-02 Lubrizol Corp Composition d'huile lubrifiante et concentre pour sa preparation contenant une composition de derive carboxylique, un ester et un sel metallique d'acide dihydrocarbyldithiophosphorique
US4938881A (en) * 1988-08-01 1990-07-03 The Lubrizol Corporation Lubricating oil compositions and concentrates
US4952328A (en) * 1988-05-27 1990-08-28 The Lubrizol Corporation Lubricating oil compositions
US4956108A (en) * 1987-07-29 1990-09-11 Mobil Oil Corporation Copper salts of thiodipropionic acid derivatives as antioxidant additives process of making the same and fuel composition thereof
US4957651A (en) * 1988-01-15 1990-09-18 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
US4981602A (en) * 1988-06-13 1991-01-01 The Lubrizol Corporation Lubricating oil compositions and concentrates
US5013467A (en) * 1987-09-16 1991-05-07 Exxon Chemical Patents Inc. Novel oleaginous composition additives for improved rust inhibition
US5021173A (en) * 1988-02-26 1991-06-04 Exxon Chemical Patents, Inc. Friction modified oleaginous concentrates of improved stability
US5049290A (en) * 1987-05-11 1991-09-17 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US5141657A (en) * 1987-10-02 1992-08-25 Exxon Chemical Patents Inc. Lubricant compositions for internal combustion engines
US5244591A (en) * 1992-03-23 1993-09-14 Chevron Research And Technology Company Lubricating oil compositions for internal combustion engines having silver bearing parts
US5320765A (en) * 1987-10-02 1994-06-14 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines
EP0652279A1 (de) * 1993-06-07 1995-05-10 Ethyl Corporation Brennstoffersparnis und Verhinderung der Oxidation in Schmierölzusammensetzungen für Verbrennungsmotoren
US6254849B1 (en) * 1999-07-28 2001-07-03 Chevron U.S.A. Inc. Zeolite SSZ-52
WO2001059037A3 (en) * 2000-02-14 2002-01-24 Exxonmobil Res & Eng Co Lubricating oils having improved fuel economy retention properties
EP1925655A1 (de) 2006-11-22 2008-05-28 Infineum International Limited Schmierölzusammensetzungen
EP2161326A1 (de) 2008-09-05 2010-03-10 Infineum International Limited Schmierölzusammensetzungen
EP2390306A1 (de) 2009-12-01 2011-11-30 Infineum International Limited Schmierölzusammensetzung
WO2011161406A1 (en) 2010-06-25 2011-12-29 Castrol Limited Uses and compositions
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
EP3115443A1 (de) 2015-07-07 2017-01-11 Ab Nanol Technologies Oy Organometallische salzzusammensetzung, verfahren zu deren herstellung und schmiermitteladditivzusammensetzung
EP3252130A1 (de) 2016-06-03 2017-12-06 Infineum International Limited Additivpaket und schmierölzusammensetzung
WO2020089212A1 (en) 2018-10-29 2020-05-07 Castrol Limited Lubricant compositions

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US6892531B2 (en) * 2003-04-02 2005-05-17 Julius J. Rim System for and methods of operating diesel engines to reduce harmful exhaust emissions and to improve engine lubrication
JP6027578B2 (ja) * 2013-08-30 2016-11-16 良光 長井 潤滑促進液
CN107964441A (zh) * 2017-10-19 2018-04-27 山东源根石油化工有限公司 一种有机铜抗氧剂以及含有该有机铜抗氧剂的柴油机油
EP3868765A1 (de) * 2020-02-21 2021-08-25 Ab Nanol Technologies Oy Verfahren zur herstellung einer organometallischen salzzusammensetzung sowie verwendung der zusammensetzung in einem schmiermittelzusatz

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US2911367A (en) * 1957-07-01 1959-11-03 Gulf Oil Corp Mineral lubricating oil composition
CA1137463A (en) * 1978-12-18 1982-12-14 Thomas V. Liston Mileage-improving lubricating oil
GB2056482A (en) * 1979-08-13 1981-03-18 Exxon Research Engineering Co Lubricating oil compositions
GB2097813B (en) * 1981-05-06 1985-09-25 Exxon Research Engineering Co Glycerol esters in lubricating oils as fuel economy additives

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2505355A1 (fr) * 1981-05-06 1982-11-12 Exxon Research Engineering Co Composition d'huile lubrifiante contenant un ester partiel de glycerol
EP0260863A3 (de) * 1986-09-15 1989-02-15 Exxon Research And Engineering Company Schmieröl
EP0280579A3 (en) * 1987-02-27 1989-03-15 Exxon Chemical Patents Inc. Low phosphorus/low zinc lubricants
US5049290A (en) * 1987-05-11 1991-09-17 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
US4915857A (en) * 1987-05-11 1990-04-10 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
EP0294045A3 (en) * 1987-05-11 1989-03-22 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
US4956108A (en) * 1987-07-29 1990-09-11 Mobil Oil Corporation Copper salts of thiodipropionic acid derivatives as antioxidant additives process of making the same and fuel composition thereof
US5013467A (en) * 1987-09-16 1991-05-07 Exxon Chemical Patents Inc. Novel oleaginous composition additives for improved rust inhibition
US5320765A (en) * 1987-10-02 1994-06-14 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines
US5141657A (en) * 1987-10-02 1992-08-25 Exxon Chemical Patents Inc. Lubricant compositions for internal combustion engines
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US4957651A (en) * 1988-01-15 1990-09-18 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
US5021173A (en) * 1988-02-26 1991-06-04 Exxon Chemical Patents, Inc. Friction modified oleaginous concentrates of improved stability
US5282991A (en) * 1988-02-26 1994-02-01 Exxon Chemical Patents Inc. Friction modified oleaginous concentrates of improved stability
US4952328A (en) * 1988-05-27 1990-08-28 The Lubrizol Corporation Lubricating oil compositions
US4981602A (en) * 1988-06-13 1991-01-01 The Lubrizol Corporation Lubricating oil compositions and concentrates
EP0389573B1 (de) * 1988-08-01 1995-01-11 The Lubrizol Corporation Schmieröl-zusammensetzungen und konzentrate
US4957649A (en) * 1988-08-01 1990-09-18 The Lubrizol Corporation Lubricating oil compositions and concentrates
FR2634780A1 (fr) * 1988-08-01 1990-02-02 Lubrizol Corp Composition d'huile lubrifiante et concentre pour sa preparation contenant une composition de derive carboxylique, un ester et un sel metallique d'acide dihydrocarbyldithiophosphorique
US4938881A (en) * 1988-08-01 1990-07-03 The Lubrizol Corporation Lubricating oil compositions and concentrates
BE1001977A3 (fr) * 1988-08-01 1990-05-02 Lubrizol Corp Compositions d'huiles lubrifiantes.
US5244591A (en) * 1992-03-23 1993-09-14 Chevron Research And Technology Company Lubricating oil compositions for internal combustion engines having silver bearing parts
EP0652279A1 (de) * 1993-06-07 1995-05-10 Ethyl Corporation Brennstoffersparnis und Verhinderung der Oxidation in Schmierölzusammensetzungen für Verbrennungsmotoren
US6254849B1 (en) * 1999-07-28 2001-07-03 Chevron U.S.A. Inc. Zeolite SSZ-52
US6379531B2 (en) * 1999-07-28 2002-04-30 Chevron U.S.A. Inc. Zeolite SSZ-52
WO2001059037A3 (en) * 2000-02-14 2002-01-24 Exxonmobil Res & Eng Co Lubricating oils having improved fuel economy retention properties
EP1925655A1 (de) 2006-11-22 2008-05-28 Infineum International Limited Schmierölzusammensetzungen
EP2161326A1 (de) 2008-09-05 2010-03-10 Infineum International Limited Schmierölzusammensetzungen
EP2390306A1 (de) 2009-12-01 2011-11-30 Infineum International Limited Schmierölzusammensetzung
US9080120B2 (en) 2010-06-25 2015-07-14 Castrol Limited Uses and compositions
WO2011161406A1 (en) 2010-06-25 2011-12-29 Castrol Limited Uses and compositions
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
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
EP3115443A1 (de) 2015-07-07 2017-01-11 Ab Nanol Technologies Oy Organometallische salzzusammensetzung, verfahren zu deren herstellung und schmiermitteladditivzusammensetzung
WO2017005967A1 (en) 2015-07-07 2017-01-12 Ab Nanol Technologies Oy Organometallic salt composition, a method for its preparation and a lubricant additive composition
US10618865B2 (en) 2015-07-07 2020-04-14 Ab Nanol Technologies Oy Organometallic salt composition, a method for its preparation and a lubricant additive composition
EP3252130A1 (de) 2016-06-03 2017-12-06 Infineum International Limited Additivpaket und schmierölzusammensetzung
WO2020089212A1 (en) 2018-10-29 2020-05-07 Castrol Limited Lubricant compositions

Also Published As

Publication number Publication date
EP0092946A3 (en) 1985-08-14
EP0092946B1 (de) 1988-03-16
JPH0377837B2 (de) 1991-12-11
CA1205451A (en) 1986-06-03
DE3376016D1 (en) 1988-04-21
JPS58191795A (ja) 1983-11-09

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