EP0302149B1 - Schmieröl mit verbesserten Eigenschaften zur Reibungsverminderung - Google Patents

Schmieröl mit verbesserten Eigenschaften zur Reibungsverminderung Download PDF

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Publication number
EP0302149B1
EP0302149B1 EP87306874A EP87306874A EP0302149B1 EP 0302149 B1 EP0302149 B1 EP 0302149B1 EP 87306874 A EP87306874 A EP 87306874A EP 87306874 A EP87306874 A EP 87306874A EP 0302149 B1 EP0302149 B1 EP 0302149B1
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Prior art keywords
composition
carbon atoms
parts
weight
reaction product
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EP87306874A
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English (en)
French (fr)
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EP0302149A1 (de
Inventor
Jan Bock
Darrell William Brownawell
Antonio Gutierrez
Max Leo Robbins
Harold Shaub
Peter L. Steyn
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to US06/846,007 priority Critical patent/US4684473A/en
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Priority to DE8787306874T priority patent/DE3775769D1/de
Priority to EP87306874A priority patent/EP0302149B1/de
Publication of EP0302149A1 publication Critical patent/EP0302149A1/de
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Classifications

    • 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
    • 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
    • C10M141/10—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 phosphorus-containing compound
    • 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
    • C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
    • 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
    • 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
    • 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
    • C10N2040/251—Alcohol-fuelled 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
    • 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 is directed to a lubricating oil composition containing an oxygenated (hydroxy) ester of a dimer acid in combination with an oil soluble alkanol phosphate to provide improved friction reducing properties and to a method of reducing friction in an internal combustion engine by using a lubricating oil composition which contains said additives.
  • European published patent application 93 598A discloses a lubricating oil composition containing, as a friction reducing additive, the reaction product of a dimer carboxylic acid having a total of 24 to 90 carbon atoms and a polyhydric alcohol having at least three hydroxyl groups and 3 to 18 carbon atoms.
  • UK patent 708 017 discloses a lubricating oil composition containing a fatty acid ester of an alcohol as an oiliness agent combined with an alkyl phosphate as a film strength improver.
  • the ester is preferably an ester of a fatty acid containing between 10 to 20 carbon atoms and a monohydric alcohol.
  • the alkyl phosphate is preferably a trialkyl phosphate.
  • the two additives act together synergistically to improve the load bearing properties of the lubricating oil composition.
  • the composition is particularly suitable for turbine oils.
  • the friction reducing additive which is used in this invention is an oil soluble oxygenated (hydroxy) ester of a dimer acid (HEDA hydroxy ester of dimer acid) in combination with an oil soluble alkanol or alkyl phosphate, wherein the oxygenated (hydroxy) ester is characterized by the formula: where R is selected from the group consisting of -CH2CH2 ⁇ -OCH2CH2] n OH; with n being equal to 1 to 5 (hereafter designated as HEDA); -CH2-CH2-N(CH2CH2OH)2 (hereinafter designated as LA214); and (hereinafter designated as LA200).
  • R is selected from the group consisting of -CH2CH2 ⁇ -OCH2CH2] n OH; with n being equal to 1 to 5 (hereafter designated as HEDA); -CH2-CH2-N(CH2CH2OH)2 (hereinafter designated as LA214); and (hereinafter designated as LA200).
  • an oxygenated (hydroxy) ester of the dimer acid as a friction-reducing agent for oils in a gasoline engine can be limited by poor solubility in the lubricating oil and adverse interactions with other lubricating oil components, wherein some of these interactions show up as sediment formation.
  • the present invention teaches that the solubilization and stabilization of the dimer acid esters in the lubricating oils is improved by the addition of an oil-soluble alkanol or alkyl phosphate.
  • the oxygenated (hydroxy) esters of the dimer acid are classified as reaction products of a dimer carboxylic acid and a polyhydric alcohol.
  • a reaction product may be a partial, di- or polyester, with typical formulae represented as follows when using a trihydric alcohol: wherein R ⁇ is the hydrocarbon radical of the dimer acid; each R and R ⁇ may be the same or different hydrocarbon radicals associated with a trihydric alcohol; and n is an integer which typically is 1 to 5 or higher.
  • the ester reaction products can be obtained by reacting a dimer carboxylic acid or a mixture of such acids with a trihydric alcohol or other polyhydric alcohol or mixtures of such alcohols.
  • the alcohol used in preparing the friction reducing reaction product additive of this invention is a polyhydric alcohol having at least 2 hydroxy groups and from 3 to 18 carbon atoms.
  • such compounds will be aliphatic and may contain branched or unbranched hydrocarbon groups, as well as other functional groups, such as nitrogen, sulfur and phosphorus.
  • Such polyhydric alcohols will contain at least 2 hydroxyl groups and may contain more, generally from 3 to 6 hydroxyl groups, with the upper amount limited by the degree of solubility and effectiveness of the reaction product in the lubricating oil composition.
  • such polyhydric alcohol will contain 2 to 4 hydroxyl groups and 3 to 12 carbon atoms.
  • such polyhydric alcohol will be saturated, contain 3 hydroxyl groups and 3 to 8 carbon atoms.
  • Compounds of this type include diethylene glycol, glycerol (i.e., 1, 2, 3, propane triol), 1, 2, 6-trihydroxyhexane and 2, 2 ⁇ , 2 ⁇ nitrilotriethanol.
  • the carboxylic acid used in preparing the oxygenated (hydroxy) esters of the dimer acid friction reducing reaction product of this invention will be a dimer of an aliphatic saturated or unsaturated carboxylic acid, said dimer acid having a total of 24 to 90 carbon atoms, and from 9 to 42 carbon between the carboxylic acid groups.
  • the dimer acid will have a total of 24 to 60 carbon atoms and 12 to 42 carbon atoms between the carboxylic acid groups, and more preferably a total of 24 to 44 carbon atoms and 16 to 22 carbon atoms between the carboxylic acid groups.
  • the molar quantities of the dimer acid and polyhydric alcohol reactants may be adjusted so as to secure either a complete ester or partial ester and generally from 1 to 3 or more moles of polyhydric alcohol will be used per mole of dimer acid and preferably from 2 to 3 moles of alcohol per mole of acid.
  • esters While any of the dimer acids and polyhydric alcohols described above may be used in preparing the friction reducing additive of this invention, the most preferred esters, as set forth above, are those wherein the carboxyl groups are separated from the closest carboxyl group by from 2 to 12 carbon atoms. Particularly useful ester additives are obtained when the acid used is a dimer of a fatty acid, preferably those fatty acids containing 12 to 22 carbon atoms. Such dimers are, of course, clearly taught in U. S. Patent No. 3,180,832, which was granted on April 27, 1965, and U. S. Patent No. 3,429,817, which was granted on February 25, 1969, and as here indicated the hydrocarbon portion of the dimer carboxylic acid thus obtained may contain a 6 member ring.
  • dimer from linoleic acid, oleic acid and mixtures of these acids is illustrated by the following reactions: It will, of course, be appreciated that while the reactions illustrated produce the dimers, commercial application of the reactions will generally also lead to trimer formation and, in some cases, the product thus obtained will contain minor amounts of unreacted monomer or monomers. As a result, commercially available dimer acids may contain as much as 25% trimer and the use of such mixtures is within the scope of the present invention. It is also noted that prepared dimer acids may be saturated or unsaturated. While in some instances the unsaturated dimer acids are preferred, it is also contemplated that if desired dimer acids formed having one or more saturated bonds may have such unsaturation removed, e.g., by hydrogenation.
  • the ester friction reducing additive of this invention will generally be used at a concentratoin level of from 0.1 to 2.0 parts by weight per 100 parts of lubricating oil composition, more preferably from 0.1 to 1.0, and most preferably from 0.2 to 1.0 parts.
  • the oil-soluble alkanol will generally be used at a concentration of from 1 to 10 parts by weight per part of the ester friction reducing additive, more preferably 1 to 5, and most preferably about 2 to about 4.
  • the lubricating base oil will generally comprise a major amount of the lubricating composition, i.e., at least 50% by weight thereof, and will include liquid hydrocarbons, such as the mineral lubricating oils and the synthetic lubricating oils, and mixtures thereof.
  • the synthetic oils which can be used include diester oils, such as di(2-ethylhexyl) sebacate, azelate and adipate; complex ester oils, such as those formed from dicarboxylic acids, glycols and either monobasic acids or monohydric alcohols; silicone oils; sulfide esters; organic carbonates; and other synthetic oils known in the art.
  • additives may be added to the oil composition of the present invention to form a finished oil.
  • additives include dispersants, antiwear agents, antioxidants, corrosion inhibitors, detergents, pour point depressants, extreme pressure additives, viscosity index improvers, etc. These additives are typically disclosed, for example, in Lubricant Additives by C. V. Smalheer and R. Kennedy Smith, 1967, pages 1-11, and in U. S. Patent No. 4,105,571.
  • Oils A and B are fully formulated SF quality SAE 10W-30 passenger car engine oils. Each oil is formulated with standard additives used in the industry to meet the requirements of current gasoline engines. Oils A and B contain the sam viscosity index improvers, dispersants, detergents, antioxidants, pour depressants and antifoamant additives. Oil A contains a zinc dialkyl dithiophosphate antiwear additive made with primary alcohols, while oil B contains a zinc dialkyl dithiophosphate antiwear additive made with secondary alcohols. This is the only difference between oils A and B.
  • Oil A and oil B, each formulated with 0.5 weight percent HEDA solubilized with C8Oh at a 3/1 alcohol/HEDA weight ratio were tested for relative friction using a ball on cylinder test, described in the Journal of the American Society of Lubricating Engineers , entitled ASLE Transactions , Volume 4, pages 1-11, 1961.
  • the apparatus consists basically of a fixed metal ball loaded against a rotating cylinder. The weight on the ball and the rotation of the cylinder can be varied during any given test or from test to test. Also, the time of any given test can be varied. Generally, however, steel on steel is used at a constant load, constant rpm, and a fixed time and in each of the tests of these examples a 4 Kg load, 0.26 rpm and 70 minutes was used.
  • oil A and oil B each with 0.5 weight percent HEDA and 1.5 weight percent C8OH, gave lower BOC friction than the base case oils without HEDA/C8 alcohol (oil A or oil B).
  • oil A or oil B the BOC data on the oxidized oil from the 3 hour Lube Stability Test (LST) is a better predictor of fuel economy differences during field service than fresh oil data.
  • Table I lists the surfactants and alcohols tested as solubilizers for dimer acid esters.
  • CO for the solubilizer refers to a series of ethoxylated nonyl phenols produced by GAF Corp. under the trademark name Igepal®.
  • OXO refers to oil soluble alcohols manufactured by the OXO process.
  • DM refers to the Igepal DM® series of ethoxylated dinonyl phenols manufactured by the GAF Corp.
  • Spans® are products of ICI Americas, Inc.; Tetronics® are products of BASF Wyandott Corp.; Tritons® are products of Rohm and Haas, Inc.; Aerosol® are products of American Cyanamid; and Emphos® designates a series of alkyl phosphates manufactured by Witco Chemical Corp. Of all the materials tested, only the alkanols and alkyl phosphates formed clear solutions, with HEDA in oil A at the ratios of solubilizer/ester indicated in the second column of Table I.

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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)

Claims (10)

  1. Schmierölzusammensetzung, die
    a) ein Basisschmieröl;
    b) 0,1 bis 2,0 Gewichtsteile pro 100 Gewichtsteile der Schmierölzusammensetzung des Reaktionsprodukts einer dimeren Carbonsäure mit insgesamt 24 bis 90 Kohlenstoffatomen und 9 bis 42 Kohlenstoffatomen zwischen den Carbonsäuregruppen und einem mehrwertigen Alkohol mit mindestens 3 bis 18 Kohlenstoffatomen, wobei das Reaktionsprodukt unter Verwendung von 1 bis 3 Molen Alkohol pro Mol dimerer Säure gebildet worden ist; und
    c) ein bis 10 Gewichtsteile einer öllöslichen Verbindung pro Teil des Reaktionsprodukts aus b), wobei die öllösliche Verbindung ausgewählt ist aus den Alkanolen und Alkylphosphaten, umfaßt.
  2. Zusammensetzung nach Anspruch 1, bei der die dimere Carbonsäure 24 bis 60 Kohlenstoffatome aufweist und der mehrwertige Alkohol 3 bis 12 Kohlenstoffatome aufweist.
  3. Zusammensetzung nach Anspruch 1 oder 2, bei der der mehrwertige Alkohol 2 oder mehr Hydroxylgruppen aufweist.
  4. Zusammensetzung nach einem der Ansprüche 1 bis 3, bei der 0,1 bis 1,0 Gewichtsteile des Reaktionsprodukts pro 100 Gewichtsteile der Schmierölzusammensetzung eingesetzt worden sind.
  5. Zusammensetzung nach einem der Ansprüche 1 bis 4, bei dem der Alkohol ausgewählt ist aus Diethylenglykol, Glycerin, 1,2,6-Trihydroxyhexan und 2,2',2"-Nitrilotriethanol.
  6. Zusammensetzung nach einem der Ansprüche 1 bis 5, bei dem die Carbonsäure eine Fettsäure ist, die 12 bis 22 Kohlenstoffatome enthält.
  7. Zusammensetzung nach einem der Ansprüche 1 bis 6, bei der 0,1 bis 1,0 Gewichtsteile (pbw) des Reaktionsprodukts pro 100 pbw der Zusammensetzung eingesetzt worden sind und der Alkohol ausgewählt ist aus Diethylenglykol, Glycerin, 1,2',6-Trihydroxyhexan und 2,2',2"-Nitrilotriethanol.
  8. Zusammensetzung nach einem der Ansprüche 1 bis 7, bei der das Alkanol durch die Formel:
    Figure imgb0016
     gekennzeichnet ist, wobei R 2 bis 16 Kohlenstoffatome enthält und linear oder verzweigt sein kann und R' Wasserstoff oder eine gerade oder verzweigte Kohlenwasserstoffkette ist, die 1 bis 5 Kohlenstoffatome enthält.
  9. Zusammensetzung nach einem der Ansprüche 1 bis 8, bei der das Alkylphosphat durch die Formel
    Figure imgb0017
     gekennzeichnet ist, wobei R₁ ein Alkyl- oder eine Alkylarylgruppe mit 6 bis 18 Kohlenstoffen in der Alkylkette ist und R₂ das gleiche wie R₁ oder H ist.
  10. Verfahren zur Reibungsminderung in einem Verbrennungsmotor, bei dem der Motor geschmiert wird, indem eine Schmierölzusammensetzung verwendet wird, die 0,1 bis 2 Gewichtsteile pro 100 Gewichtsteile der Schmierölzusammensetzung eines Additivs enthält, daß das Reaktionspropdukt in der dimeren Carbonsäure mit 24 bis 90 Kohlenstoffatomen und eines mehrwertigen Alkohols mit mindestens zwei Hydroxylgruppen und 3 bis 18 Kohlenstoffatomen ist, in Kombination mit einer öl-löslichen Verbindung ausgewählt aus der Gruppe bestehend aus Alkanolen und Alkylphosphaten.
EP87306874A 1986-03-31 1987-08-03 Schmieröl mit verbesserten Eigenschaften zur Reibungsverminderung Expired - Lifetime EP0302149B1 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US06/846,007 US4684473A (en) 1986-03-31 1986-03-31 Lubricant oil composition with improved friction reducing properties
DE8787306874T DE3775769D1 (de) 1987-08-03 1987-08-03 Schmieroel mit verbesserten eigenschaften zur reibungsverminderung.
EP87306874A EP0302149B1 (de) 1987-08-03 1987-08-03 Schmieröl mit verbesserten Eigenschaften zur Reibungsverminderung

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Application Number Priority Date Filing Date Title
EP87306874A EP0302149B1 (de) 1987-08-03 1987-08-03 Schmieröl mit verbesserten Eigenschaften zur Reibungsverminderung

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EP0302149B1 true EP0302149B1 (de) 1992-01-02

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9289729B2 (en) 2013-03-16 2016-03-22 Dow Global Technologies Llc Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8968828B2 (en) 2011-01-24 2015-03-03 Dow Global Technologies Llc Composite polyamide membrane
WO2013048763A1 (en) * 2011-09-29 2013-04-04 Dow Global Technologies Llc Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent
US9051227B2 (en) 2013-03-16 2015-06-09 Dow Global Technologies Llc In-situ method for preparing hydrolyzed acyl halide compound
US9051417B2 (en) 2013-03-16 2015-06-09 Dow Global Technologies Llc Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
GB708017A (en) * 1951-08-23 1954-04-28 Standard Oil Dev Co Lubricating oil composition
US4459223A (en) * 1982-05-05 1984-07-10 Exxon Research And Engineering Co. Lubricant oil composition with improved friction reducing properties

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9289729B2 (en) 2013-03-16 2016-03-22 Dow Global Technologies Llc Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer

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DE3775769D1 (de) 1992-02-13

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