CA1174660A - Glycerol esters as fuel economy additives - Google Patents

Glycerol esters as fuel economy additives

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Publication number
CA1174660A
CA1174660A CA000401271A CA401271A CA1174660A CA 1174660 A CA1174660 A CA 1174660A CA 000401271 A CA000401271 A CA 000401271A CA 401271 A CA401271 A CA 401271A CA 1174660 A CA1174660 A CA 1174660A
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CA
Canada
Prior art keywords
composition
lubricating oil
fuel economy
oil
glycerol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000401271A
Other languages
French (fr)
Inventor
Phillip W. Brewster
Clinton R. Smith
Frederick W. Gowland
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.)
Imperial Oil Ltd
Original Assignee
Imperial Oil Ltd
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 Imperial Oil Ltd filed Critical Imperial Oil Ltd
Application granted granted Critical
Publication of CA1174660A publication Critical patent/CA1174660A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/76Esters containing free hydroxy or carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/289Partial esters containing free hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12

Landscapes

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

Abstract

ABSTRACT OF THE DISCLOSURE
Lubricating oil compositions are disclosed exhibiting improved fuel economy which contain 0.05 to 0.2 wt. % of a glycerol partial ester of a C16-C18 fatty acid as the fuel economy additive.

Description

1 This invention relates to lubricating oil composi-
2 tions which exhibit marked improvements in fuel economy.
3 ~lore particularly, this invention relates to lubricating
4 oil compositions which contain very ~inor proportions of a glycerol fatty acid ester fuel economy additi~e. It is 6 a current objective of the industry to provide lubricating 7 oil compositions which exhibit improvements in fuel savings 3 in gasoline and diesel engine vehicles. To ~eet that g current goal, a new category of additives commonly refer-red to as fuel economy additives are being developed 11 which function primarily to increase the miles or kilo-12 meters obtained per unit volume of fuel. Since modern 13 day lubricating oil co~.positions are complex fsrmulations, 14 such additives ~ust be compatible with the other components of such compositions and should not adversely affect the 16 numerous other functions of conventional lubricant addi-17 tives such as dispersancy, viscosity stability, corrosion 18 and oxidation inhibition, and the like.
19 I}lustrative of recent patents reflecting develop-ments in this field are the U.S. Patent 4,201,684 issued 21 ~ay 6, 1980 to Malec and U.S. Patent 4,208,293 issued 22 June 17, 1980 to Zaweski. These patents show th~e use of 23 fatty acid amides and sulfurized amides as additives 24 which have fuel economy benefits as demonstrated by fric-tion reducing data. The present invention concerns the 26 use of glycerol fatty acid esters as such fuel economy 27 additives, specifically glycerol esters of C16-Clg fatty 28 acids. There~is prior art disclosing the use of such 29 materials in lubricating oil compositions which is dis-cussed hereinbelow.
31 West German Applications P-2949910 and P-2949940 32 of Chevron Research Company both published July 3, 1980 33 disclose the use of glycerol fatty esters as fuel economy 34 additives. These publications correspond to U.S. Patent 3S Application Serial Nos. 970,698 and 970,699 both filed 36 December 18, 1978 by Liston. These references state that 37 the addition of 0.25 to 2 weight percent, preferably 0.40 1 17~6BO

1 to 1.25 weight percent, of a fatty acid ester wlll offer 2 a fuel economy credit of 2-3 percent in both gasoline and 3 diesel engines. Glycerol oleic acid esters are prefer-4 red. '~est German Application P-2949940 illustrates the preferred embodiment showing the use of the glycerol 6 ester at the same treat level in combinat'on with zinc 7 dihydrocarbyl dithiophosphate additives. In contrast to 8 the teachings of these references, the present invention, 9 resulting from engine testing of fully formulated composi-tions, is based upon the discovery that very low levels 11 of glycerol esters that is up to about 0.2 percent by 12 weight, provide optimum performance in terms of actual 13 evaluation of fuel economy data. No benefit is obtainable 14 in using relatively higher amounts and in some cases substantial debits in terms of formulation stability or 16 adverse performance may occur.
17 Another reference disclosing the use of polyol -18 carboxylic acid esters in lubricating oil compositions is 19 U.S. Patent 3,933,659 issued January 20, 1976 to Lyle et al which shows a multi-comoonent functional fluid, one 21 component of which can be a polyol ester friction modi-22 fier or a fatty acid amide friction modifier. The primary 23 use disclosed in that reference is~for automatic trans-24 mission fluids. U.S. Patent ~,27~,891 issued September 20, 1966 to ~urey et al discloses anti-wear additives compris-26 ing a mixture of dimer acids and a partial ester of a 27 polyhydric alcohol, the additive being noted as improving 28 lubricity as well as functioning in the anti-wear category.
29 U.S. Patent 3,112,271 to Calhoun discloses glycerol mono-oleate as an extreme pressure additive as does U.S.
31 3,112,269 issued ~ovember 23, 1963 to Calhoun et al and 32 U.S. 3,041,284 issued January 26, 1962 to Calhoun et al.
33 U.S. 2,493,483 issued to Frances et al on January 3, 1950 34 discloses marine engine lubricants which contain a partial ester of glycerol or other polyol fatty acid esters in 36 amounts of from 0.05 to 1 percent.

l Other references disclosing ~olyol esters of 2 fatty acids are represented by U.S. 2,788,326 issued to 3 Bondi et al issued April g, 1957 which discloses these 4 compounds as being useful in extreme pressure lubricants and U.S. 2atent 2,527,889 issued October 31, 1950 to 6 ~loore et al which shows the same polyol esters, such as 7 glycerol monooleate, being useful as anti-corrosion agents 8 in turbine oils in diesel fuels.
g The present invention is based upon the discovery that there is a certain range of additive concentration 11 in connection with the use of polyol esters in crankcase 12 lubricating oil compositions which imparts a degree of 13 fuel economy per unit weight of additive not heretofore 14 recognized by the art, when glycerol esters are employed in a fully formulated lubricating oil and evaluated by 16 fired engine tests. Of equal significance is the fact 17 that other desirable effects and properties of lubricating 18 oils, e.g., compatibility, detergency and dispersancy, 19 are not diminished.
In accordance with the ~resent invention, t~ere 21 are provided fuel economy promoting lubricating oil com-22 positions which comprise an oil of lubricating viscosity 23 and,as the fuel economy additive,from 0.05 to 0.2 weight 24 percent of a glycerol partial ester of a Cl6-Cl8 fatty acid, thereby providing a fuel economy improvement of 26 about l to 3 percent when compared with the same lubricat-27 ing oil composition without the fuel economy additive.
28 The lubricating oil compositions of the present 29 invention comprise both straight grade and multigrade lubricating oil formulations for both gasoline and diesel 31 (compression ignition) engines. Thus, in the practice of 32 the present invention the lubricating oil compositions 33 will contain those additive systems formulated to meet 34 the viscosity requirements or other specifications as required for qualification as a gasoline engine or diesel 36 lubricating oil. A straight grade lubricating oil formu-37 lation will normally contain conventional amounts of an I J

1 ashless dispersant, a normal or basic metal detergent, an 2 anti-wear additive and anti-oxidant and a multi-grade oil 3 will contain, in addition to the foregoing, a viscosity 4 index improver or viscosity modifier. In addition to these principal additives, very small proportions of 6 other special purpose additives, such as pour depressants, 7 rust inhibitors, anti-foamants and the like are con-8 ventionally blended into lubricating oil compositions.
g The fuel economy additive of the present in-vention is preferably a gl~cerol mono- or di- ester of a 11 saturated or unsaturated C16-Clg fatty acid such as oleic 12 or linoleic acid. Optimum efficiency has been found to 13 be at about the 0.2 weight percent level and use in the 14 excess of this amount may even be detrimental to the overall performance of the lubricating oil composition.
16 Crankcase oil formulations to which the present 17 invention relates are those which contain a major amount 18 of lubricating oil and effective amounts of conventional 19 additives in addition to the aforesaid fuel economy additive. Percentages of additives as described herein 21 are by weight based on the total weight of lubricating 22 oil formulation unless otherwise reported.
23 These conventional additives comprise an ashless 24 dispersant which is typically a nitrogen-containing dis-persant additive which are oil-soluble salts, amides, 26 imides and esters made from high molecular weight mono-27 and di- carboxylic acids and various amines having an 28 amino or heterocyclic nitrogen with at least one amido or 29 hydroxy group cabable of salt, amide or ester formation.
Preferred are the reaction products of polyolefin (C2-C5 31 olefin),such as polyisobutenyl~succinic anhydride with an 32 alkylene polyamine such as tetraethylenepentamine. The 33 polyisobutenyl portion has between 50 and 250 carbon 34 atoms. The alkylene polyamines are those represented by 35 the formula:
36 NH2(CH2)n(NH(CH2)n)m~~H2 1 where n is 2 to 3 and m is a number from 0 to 10. Mix-2 tures of alkylene ?olyamines which approximate tetra-3 ethylenepentamine are commercially used materials. Dis-4 persants are used generally in amounts of ~rom about 0.1 to 10 ~t. ~, preferablv in the range of about 0.5 to 5 6 wt. ~ based on the weight of the lubricating oil com-7 position.
8 Detergents useful in the formulations include 9 the normal, basic or overbased metal, that is, calcium, magnesium and so forth, salts of petroleum naphthenic 11 acids, petroleum sulfonic acids, alkyl benzene sulfonic 12 acids, alkyl phenols, alkylene-bis-phenol, oil-soluble 13 fatty acids and the like. The preferred materials are 14 the normal or overbased calcium or magnesium phenates, sulfurized phenates and/or sulfonates, and these metal-16 containing detergent additives are typically used in 17 amounts of from 1 to 3 wt. ~ based on the total weight of 18 lubricating oil compositions.
19 Examples of suitable oxidation inhibitors are hindered phenols, such as 2,6-ditertiary butyl para-21 cresol, amines, sulfurized phenol and alkyl phenothia-22 zines; usually a lubricating oil will contain about 0.01 23 to 3 wt. ~ of oxidation inhibitor depending on its 24 effectiveness.
Suitable pour point depressants, which are 26 usually present in amounts of about 0.01 to 1 wt. ~, 27 include wax alkylated aromatic hydrocarbons, olefin 28 polymers and copolymers, acrylate and methacrylate poly-29 mers and copolymers.
Anti-wear additives generally are the oil-soluble 31 zinc dihydrocarbyldithiophosphates having at least 32 a total of 5 carbon atoms, the alkyl grouo being prefer-33 ably C2-Cg. These are typically present in amounts of 34 from 0.01 to 5 wt. ~, preferably 0.5 to 1.5 wt. ~, in the lubricating oil.
36 Suitable conventional viscosity index improvers, 37 or viscosity modifiers, are the olefin polymers such as 1 polybutene, ethylene-propylene copolymers, hydrogenated 2 polymers and copoly~ers and terpolymers of styrene with 3 isoprene and/or butadiene, pol~mers of alkyl acrylates or 4 alkyl methacrylates, copolymers of alkyl methacrylates with N-vinyl pyrollidone or dimethylaminoalkyl meth-6 acrylate, post-grafted polymers of ethylene-propylene 7 with an active monomer such as maleic anhydride which may 8 ~e further reacted with an alcohol or an alkylene poly-9 amine, styrene-maleic anhydride polymers post-reacted with alcohols and amines and th~ like. These additives 11 are used in amounts of about 1.5~ to 15~ by wt., depending 12 on the exact viscosity specifications desired.
13 Suitable hydrocarbon base stocks are those 14 mineral oils of lubricating viscosity as measured by ASTM
D-455 of from about 2 to 40, preferably 5 to 20 centistokes 16 at 99C.
17 These conventional additives are used in amounts 18 nor~ally necessary to provide their attendant functions 19 in a formulated crankcase lubricating oil composltion.
Very small proportions of additional special purpose 21 additives, such as anti-foam agents or rust inhi~itors 22 may also be present in a fully formulated lubricating oil 23 composition.
24 The invention is further illustrated by the following Examples which are not to be considered as 26 limitative of its scope.
27 Example 1 28 The reference oil used in this example was a 29 formulated straight grade 20W30 crankcase mineral lubri-cating oil (corresponding to AST~ "H~" oil) to which was 31 added 0.2 weight percent of a glycerol monooleate (GM0 32 fuel economy additive or 0.2 weight percent of a fuel 33 economy additive being a mixture (G~O/GD0) of glycerol 34 monooleate and glycerol dioleate in a weight ratio of 3 parts of G~O to 2 parts of GD0 in said mixture. The 36 reference oil contained 2.10 wt. % dispersant, 1.10 wt. %
37 antioxidant, 1.00 wt. % basic metal detergent, 1.95 wt. ~

1 ~74660 1 anti-wear additive, 0.21 wt. % pour depressant and 0.001 2 wt. % anti-foam agent. This type of reference oil, which 3 is generally accepted by the industry for establishing fuel economy data, provides a reproducible baseline against which fuel economy credits may be measured and is 6 considered to provide test results which accurately reflect 7 the effect of a given fuel economy additive.
8 Fuel economy was evaluated using the Laboratory 9 Engine Fuel ~conomy Test (L~FET) summarized below:
The fuel economy test used is a fired engine 11 procedure. ~he engine is a 5.0 L, V-8 Chevrolet engine 12 coupled to a water cooled electric dynamometer. The 13 engine is run with a dry sump by the use of external oil 14 pumps. One pump supplies oil to the oil gallery from an external sump and a second pump scavenges the sump and 16 returns the oil to the external sump. The conditions 17 that the engine runs at are as follows:
Condition Speed Load Temperature (C) (rpm) (in lb) Coolant Oil 21 1 (idle)a 800 400 80 98 22 2 (30 mph)b 1200 450 80 98 23 3 (30 mph)a 1200 900 80 98 24 4 (55 mph)b 2200 900 80 98 26 a - engine load higher than road load.
27 b - engine load equivalent to road load.
28 The results are expressed as a percentage credit 29 with respect to the referenced oil. Results at the 0.2 wt. % treat level for both G~O and the GM0/GD0 mixture 31 are set forth in Table I.

1 17d~660 2 TABL~ I - LEFET ~ESULTS
3 ~uel Economy Credit, Engine Conditi~n G~O GMO/GDO
1 4.0 2.6 6 2 2.5 3.0 7 3 1.5 1.8 4 0.9 0.6 9Weighted Average 1.9 1.8 Exam~le 2 11 (a) Comparative evaluations utilizing increased 12 amounts of the G~O/GDO mixture, that is, at the 0.3 13 weight percent and 0.5 weight percent levels showed no 14 increase in fuel economy credit for treatment at these levels and in some cases, an adverse effect on fuel 16 economy credits or other lubricating oil peLformance 17 criteria, such as increased piston deposit formation 18 tendencies or poor results in bearing corrosion tests.
19 (b) Coefficient of friction (CF) testing using a Roxana Four-ball wear tester in accordance with the 21 procedure described in ASTM D226-67 at 110C, 2.5 RPM at 22 both 15 kg and 3 kg was carried out with a formulated 23 mineral oil (Base oil) containing conventional amounts of 24 dispersant (2.12%), basic metal sulfonate (1.02%), anti-oxidant (0.72%), anti-wear additive (1.96~) and viscosity 26 index improver (only present at 8.7 wt. ~ in test oils 5 27 and 6 to evaluate compatibility) to which was added vary-28 ing amounts of the GD0/G~O mixture. The results in 29 Table II below show essentially no additional friction reducing benefit at levels in excess of 0.2 wt. ~ and at 31 0.9 wt. % in the test hazing evidencing potential in-32 stability or incompatibility was observed.

1 ~74~60 TABLE I I - CF RESULTS
2 Test Oil CF (15 kg) CF (3 kg) Compatibility 3 1. Base Oil 0.23 0.19 Clear 4 2. Base Oil + 0.18 0.14 Clear 0.1% GDO/GMO
3. Base Oil + 0.11 0.11 Clear 6 0.2~ GDO/GMO
7 4. Base Oil + 0.11 0.11 Clear 8 0.3% GDO/GMO
9 5.* Base Oil + 0.11 0.11 Clear 0.4% GDO/G~O
6.* Base Oil + 0.10 0.10 Hazy ll 0.9% GDO/G~O

14 * 8.7 wt. 3 of a V.I. improver was present only in formulations 5 and 6 since compatibility was important 16 at these concentrations.
17 ExamPle 3 A 18 (~) The laboratory fuel economy test of Example 1 19 was repeated utilizing a 10W40 multigrade mineral oil containing 0.09 wt. ~ of the GMO/GDO mixture as the fuel 21 economy additive. The oil contained about 14~ by wt. of 22 a multifunctional dispersant viscosity index improver, 23 0.5% dispersant, 1.85% of basic metal detergent, 0.75 wt.
24 of anti-wear additive and 0.75% antioxidant.
Table III shows the fuel economy credits over 26 the oil used as the reference in Example 1.

28 TA8LE III - ~ULTI-GR~DE OIL-LEF~T RESULTS

Engine Condition Fuel Economy Credit, 36 Weighted Average 1.8 ~174660 tb) Utilizing the same oil as Example ~(a) the 2 laboratory fuel economy results were confirmed in the 3 Proposed ASTM 5 Car Interim Fuel Economy Procedure which 4 utilized the E~A car certification cycle in 5 automobiles having engine sizes of 2.3 liter, 2.8 liter, 3.7 liter, 6 3.8 liter and 5.0 liter. Five Car average fuel economy 7 credit of 1.64~ was obtained in one series of fueI
8 economy tests.

.

.

Claims (7)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE PROPERTY OR
PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A lubricating oil composition formulated for use as a crankcase lubricating oil composition for gasoline or diesel engines consisting essentially of a major amount of a mineral oil of lubricating viscosity which has incorporated therein (i) from about 0.05 - 0.20 wt. % of a glycerol partial ester, or mixtures thereof, of a C16-C18 fatty acid, said ester providing a fuel economy improvement of about 1 - 3 percent when said lubricating oil composition is employed in the crankcase of said engines, (ii) an ashless dispersant, (iii) a metal detergent additive, (iv) a zinc dihydrocarbyl dithiophosphate anti-wear additive and (v) an antioxidant, said dispersant, detergent anti-wear additive and antioxidant being present in conventional amounts to provide their normal attendant functions.
2. The composition of claim 1 wherein the fatty acid is oleic acid.
3. The composition of claim 1 wherein said partial ester is a mixture of glycerol monooleate and glycerol dioleate.
4. The composition of claim 1 or 3 wherein there is present 0.1 to 0.2 weight percent of said partial ester.
5. The composition of claim 1 or 3 wherein said lubricating oil composition contains a viscosity index improver.
6. The composition of claim 1 or 3 wherein said composition is a gasoline engine lubricating oil composition.
7. The composition of claim 1 or 3 wherein said composition is a diesel engine lubricating oil composition.
CA000401271A 1981-05-06 1982-04-20 Glycerol esters as fuel economy additives Expired CA1174660A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26098781A 1981-05-06 1981-05-06
US260,987 1981-05-06

Publications (1)

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CA1174660A true CA1174660A (en) 1984-09-18

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CA000401271A Expired CA1174660A (en) 1981-05-06 1982-04-20 Glycerol esters as fuel economy additives

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JP (1) JPS57187394A (en)
AU (1) AU554024B2 (en)
BE (1) BE893083A (en)
CA (1) CA1174660A (en)
DE (1) DE3216390C2 (en)
FR (1) FR2505355B1 (en)
GB (1) GB2097813B (en)
HK (1) HK41090A (en)
IT (1) IT1151566B (en)
NL (1) NL8201866A (en)
SG (1) SG60888G (en)

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Publication number Priority date Publication date Assignee Title
DE3376016D1 (en) * 1982-04-22 1988-04-21 Exxon Research Engineering Co Glycerol esters with oil-soluble copper compounds as fuel economy additives
WO1988006616A1 (en) * 1987-03-02 1988-09-07 Idemitsu Kosan Company Limited Lubricating oil composition
US5273672A (en) * 1987-03-02 1993-12-28 Idemitsu Kosan Company Limited Lubricating oil composition containing a partial ester of a polyhydric alcohol and a substituted succinic acid ester
US5064546A (en) * 1987-04-11 1991-11-12 Idemitsu Kosan Co., Ltd. Lubricating oil composition
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
EP0466297B1 (en) * 1990-07-09 1994-06-01 Ethyl Additives Corporation Use of a particular ester
US5282990A (en) * 1990-07-31 1994-02-01 Exxon Chemical Patents Inc. Synergistic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine
WO1992002602A1 (en) * 1990-07-31 1992-02-20 Exxon Chemical Patents Inc. Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine
JP5127102B2 (en) * 2001-09-06 2013-01-23 Jx日鉱日石エネルギー株式会社 Lubricating oil composition for internal combustion engines
RU2451062C2 (en) * 2006-02-21 2012-05-20 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. Lubricating oil composition
CN103097497B (en) * 2010-06-25 2015-05-06 卡斯特罗尔有限公司 Uses and compositions
CN103314084B (en) 2010-10-26 2015-11-25 卡斯特罗尔有限公司 The non-water lubricating agent of the fatty acid ester containing hydroxycarboxylic acid and fuel composition and uses thereof
GB201817589D0 (en) 2018-10-29 2018-12-12 Castrol Ltd Lubricant compositions
CN114591778A (en) * 2022-02-15 2022-06-07 黄国帮 Energy-saving emission-reducing diesel and gasoline engine oil formula

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GB709903A (en) * 1950-04-06 1954-06-02 Standard Oil Dev Co Lubricating oil composition
US2911367A (en) * 1957-07-01 1959-11-03 Gulf Oil Corp Mineral lubricating oil composition
US3933659A (en) * 1974-07-11 1976-01-20 Chevron Research Company Extended life functional fluid
CA1137463A (en) * 1978-12-18 1982-12-14 Thomas V. Liston Mileage-improving lubricating oil
CA1157846A (en) * 1978-12-18 1983-11-29 Thomas V. Liston Fuel economy
EP0039998B1 (en) * 1980-05-08 1984-04-18 Exxon Research And Engineering Company Lubricating oil composition containing sediment-reducing additive
JPS5776096A (en) * 1980-10-31 1982-05-12 Idemitsu Kosan Co Ltd Lubricant oil composition
DE3376016D1 (en) * 1982-04-22 1988-04-21 Exxon Research Engineering Co Glycerol esters with oil-soluble copper compounds as fuel economy additives

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IT1151566B (en) 1986-12-24
GB2097813B (en) 1985-09-25
GB2097813A (en) 1982-11-10
IT8221100A0 (en) 1982-05-05
NL8201866A (en) 1982-12-01
JPS57187394A (en) 1982-11-18
HK41090A (en) 1990-06-01
AU554024B2 (en) 1986-08-07
DE3216390C2 (en) 1996-11-21
FR2505355B1 (en) 1986-04-11
BE893083A (en) 1982-11-05
FR2505355A1 (en) 1982-11-12
SG60888G (en) 1989-03-10
AU8340582A (en) 1982-11-11
DE3216390A1 (en) 1983-01-13

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