EP0466297A1 - Use of a particular ester - Google Patents

Use of a particular ester Download PDF

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Publication number
EP0466297A1
EP0466297A1 EP91302587A EP91302587A EP0466297A1 EP 0466297 A1 EP0466297 A1 EP 0466297A1 EP 91302587 A EP91302587 A EP 91302587A EP 91302587 A EP91302587 A EP 91302587A EP 0466297 A1 EP0466297 A1 EP 0466297A1
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Prior art keywords
ester
oil
glycerol
seal compatibility
composition
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EP91302587A
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German (de)
French (fr)
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EP0466297B1 (en
Inventor
Ingrid Christiane Denys
Harry Chafetz
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Texaco Services Europe Ltd
Afton Chemical Additives Corp
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Texaco Services Europe Ltd
Texaco Belgium NV SA
Texaco Development Corp
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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
    • 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
    • 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
    • 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
    • C10M129/74—Esters of polyhydroxy compounds
    • 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
    • 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
    • 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
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/286—Esters of polymerised unsaturated acids
    • 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
    • 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

  • a serious problem facing the lubricant manufacturer is that of seal deterioration in the engine.
  • All internal combustion engines use elastomer seals, such as nitrile-rubber or fluorocarbon-rubber seals, in their assembly. Over time, these seals are susceptible to serious deterioration caused by the lubricating oil composition.
  • a lubricating oil composition that degrades the elastomer seals in an engine is unacceptable to engine manufacturers and has limited value.
  • U.S. Patent No. 4,304,678 discloses a lubricating oil composition containing a friction modifier from the class of glycerol esters.
  • the present invention provides a solution to the problem of seal compatibility of a lubricating oil composition.
  • the lubricating oil composition comprises a major portion of a lubricating oil and an effective seal compatibility amount of a glycerol ester of an unsaturated fatty acid.
  • the nitrile seal compatible lubricating oil of the invention comprises an oil of lubricating viscosity and a minor amount, effective to impart nitrile-seal compatibility properties to the oil composition, of an ester of glycerol and an unsaturated fatty acid having from about 8 to 45 carbon atoms.
  • the ester which imparts the seal compatibility properties may be a mono-, di- or triester of glycerol and may be prepared from a simple unsaturated fatty acid or a mixture of unsaturated fatty acids.
  • the fatty acid will contain from about 8 to 45 carbon atoms,preferably 12 to 30 carbon atoms.
  • These fatty acids may be represented by the formula R-COOH in which R is an unsaturated aliphatic radical having from 7 to 44 carbon atoms.
  • the preferred unsaturated fatty acids have from 12 to 30 carbon atoms.
  • Typical unsaturated fatty acids which are suitable include the following: oleic, linoleic, hexadecenoic and linolenic.
  • the ester additive of the invention is made by either reacting glycerol with one or more of the prescribed fatty acids or by reacting natural triglyceride oils with water or glycerol according to known methods.
  • the ester additive may be a monoester, diester or triester or a mixture of mono-, di- and triesters. In general, it is preferable to have a high proportion of monoesters in the ester additive.
  • Typical glycerol esters of unsaturated fatty acids which are suitable are illustrated by the following: glyceryl monooleate; glyceryl dioleate; glyceryl trioleate; glyceryl monolinoleate; glyceryl dilinoleate and glyceryl trilinoleate and glyceryl ricinoleate.
  • the lubricating oils contemplated for use with the esters herein disclosed include both mineral and synthetic hydrocarbon oils of lubricating viscosity and mixtures thereof with other synthetic oils.
  • the synthetic hydrocarbon oils include long chain alkanes, such as cetanes, and olefin polymers, such as trimers and tetramers of octene and decene.
  • the synthetic oils, which can be used as the sole lubricating oil, or which can be mixed with the mineral or synthetic hydrocarbon oil include (1) fully esterified ester oils, with no free hydroxyls, such as pentaerythritol esters of monocarboxylic acids having 2 to 20 carbon atoms, (2) polyacetals and (3) siloxane fluids.
  • esters are those made from polycarboxylic acids and monohydric alcohols. More preferred are the ester fluids made from pentaerythritol, or mixtures thereof with di- and tripentaerythritol, and an aliphatic monocarboxylic acid containing from 1 to 20 carbon atoms, or mixtures of such acids.
  • An effective amount of ester in the lubricant for nitrile seal compatibility is an amount ranging from about 0.01 to 3.0 weight percent based on the weight of the oil composition.
  • a preferred concentration is from 0.1 to 0.75 weight percent.
  • a lubricating oil additive and blended lubricating oil compositions containing the additive is the compatibility of the oil composition with the rubber seals employed in the engine.
  • Some of the nitrogen containing succinimide dispersants and other additives such as active sulfur compounds employed in crankcase lubricating oil compositions may have the effect of seriously degrading the elastomer seals in internal combustion engines.
  • such additives are known to attack rubber seals, such as nitrile rubber and fluorocarbon rubber seals which are commonly employed in internal combustion engines. This deterioration exhibits itself by sharply degrading the flexibility of the seals and in increasing their hardness. This is such a critical problem that a number of automotive engine builders
  • the test method for the Mercedes-Benz Seal Compatibility Test is based on the VDA 521-01 test procedure.
  • the seal compatibility test is conducted by soaking samples of the elastomer-rubber in the oil under investigation at an elevated temperature and then measuring the effect of the oil composition on the rubber sample for volume change, elongation change, hardness change and tensile strength change.
  • test oil is added in a ratio of 1:80 of elastomer to oil in the beaker.
  • the elastomer specimens in the beaker are aged for 168 hours in an oven maintained at 100° C.
  • the beakers are removed from the oven and the specimens are removed from the beaker and cleaned with absorbent paper. Elongation and tensile strength measurements are made on each aged specimen. Each specimen is weighed in air and in water and measured for hardness.
  • Oil 2 containing the glyceryl monooleate exhibited excellent nitrile seal compatibility properties.
  • Oil 1 A fully formulated lubricating oil composition designated as Oil 1 was employed in the CCMC Seal Test, the Mercedes-Benz Seal Test and the MAN Seal Test. Modifications of this oil, designated as Oil 2 containing 0.20 weight percent glyceryl monooleate and Oil 3 containing 0.55 weight percent glyceryl monooleate, which was supplied by C. P. Hall, were also employed in the CCMC Seal Test. The elastomer tested was a nitrile rubber. The test results are indicated in Table 2 below.
  • the additive oils of the invention containing glyceryl monooleate exhibited excellent improved nitrile seal compatibility properties.
  • the lubricating oil employed in this example was a fully formulated gasoline engine oil and is designated as Oil 1.
  • Oil 2 contains 0.20 weight percent of glyceryl monooleate
  • Oil 3 contains 0.55 weight percent of glyceryl monooleate
  • oil 4 contains 0.20 weight percent of Radiasurf 7150, another brand of glyceryl monooleate.
  • a commercial Ford Factory Fill lubricating oil composition was tested in the CCMC Seal Compatibility Test.
  • a modified oil or variant was prepared containing 0.20 weight percent of glyceryl monooleate.
  • a nitrile rubber was used in the test. The results are reported in Table 4 below.
  • glycerol esters were tested in the same lubricating oil employed in Example II. In all cases, the glycerol ester was employed in a concentration of 0.20 weight percent. The following table lists the oils tested and the particular glycerol ester.
  • the test results show that there is criticality in the nature of the glycerol ester.

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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)
  • Sealing Material Composition (AREA)
  • Lubricants (AREA)

Abstract

A lubricating oil composition comprising an oil of lubricating viscosity and a minor amount effective to provide nitrile elastomer seal compatibility to the oil composition of an ester of glycerol and an unsaturated fatty acid.

Description

  • Internal combustion engines operate under a wide range of temperatures including low temperature stop-and-go service, as well as high temperature conditions produced by continuous high speed driving. Sludges or insolubles are produced under some operating conditions and dispersants are added to the lubricating oil so that potentially insoluble materials remain dispersed in the oil.
  • It is known to employ nitrogen containing dispersants and/or detergents in the formulation of crankcase lubricating oil compositions. Many of the known dispersant/detergent compounds are based on the reaction of an alkenylsuccinic acid or anhydride with an amine or polyamine to produce an alkylsuccinimide or an alkenylsuccinamic acid as determined by selected conditions of reaction.
  • It is also known to chlorinate alkenylsuccinic acid or anhydride prior to the reaction with an amine or polyamine in order to produce a reaction product in which a portion of the amine or polyamine is attached directly to the alkenyl radical of the alkenyl succinic acid or anhydride. The thrust of many of these processes is to produce a product having a relatively high level of nitrogen in order to provide improved dispersancy in a crankcase lubricating oil composition.
  • A serious problem facing the lubricant manufacturer is that of seal deterioration in the engine. All internal combustion engines use elastomer seals, such as nitrile-rubber or fluorocarbon-rubber seals, in their assembly. Over time, these seals are susceptible to serious deterioration caused by the lubricating oil composition. A lubricating oil composition that degrades the elastomer seals in an engine is unacceptable to engine manufacturers and has limited value.
  • It is an object of this invention to provide a lubricating oil composition which does not degrade nitrile elastomer seals in internal combustion engines.
  • U.S. Patent No. 4,304,678 discloses a lubricating oil composition containing a friction modifier from the class of glycerol esters.
  • The present invention provides a solution to the problem of seal compatibility of a lubricating oil composition. The lubricating oil composition comprises a major portion of a lubricating oil and an effective seal compatibility amount of a glycerol ester of an unsaturated fatty acid.
  • The nitrile seal compatible lubricating oil of the invention comprises an oil of lubricating viscosity and a minor amount, effective to impart nitrile-seal compatibility properties to the oil composition, of an ester of glycerol and an unsaturated fatty acid having from about 8 to 45 carbon atoms. The ester which imparts the seal compatibility properties may be a mono-, di- or triester of glycerol and may be prepared from a simple unsaturated fatty acid or a mixture of unsaturated fatty acids. In general, the fatty acid will contain from about 8 to 45 carbon atoms,preferably 12 to 30 carbon atoms. These fatty acids may be represented by the formula R-COOH in which R is an unsaturated aliphatic radical having from 7 to 44 carbon atoms.
  • The preferred unsaturated fatty acids have from 12 to 30 carbon atoms. Typical unsaturated fatty acids which are suitable include the following: oleic, linoleic, hexadecenoic and linolenic.
  • The ester additive of the invention is made by either reacting glycerol with one or more of the prescribed fatty acids or by reacting natural triglyceride oils with water or glycerol according to known methods. The ester additive may be a monoester, diester or triester or a mixture of mono-, di- and triesters. In general, it is preferable to have a high proportion of monoesters in the ester additive.
  • Typical glycerol esters of unsaturated fatty acids which are suitable are illustrated by the following: glyceryl monooleate; glyceryl dioleate; glyceryl trioleate; glyceryl monolinoleate; glyceryl dilinoleate and glyceryl trilinoleate and glyceryl ricinoleate.
  • The lubricating oils contemplated for use with the esters herein disclosed include both mineral and synthetic hydrocarbon oils of lubricating viscosity and mixtures thereof with other synthetic oils. The synthetic hydrocarbon oils include long chain alkanes, such as cetanes, and olefin polymers, such as trimers and tetramers of octene and decene. The synthetic oils, which can be used as the sole lubricating oil, or which can be mixed with the mineral or synthetic hydrocarbon oil include (1) fully esterified ester oils, with no free hydroxyls, such as pentaerythritol esters of monocarboxylic acids having 2 to 20 carbon atoms, (2) polyacetals and (3) siloxane fluids. Especially useful among the synthetic esters are those made from polycarboxylic acids and monohydric alcohols. More preferred are the ester fluids made from pentaerythritol, or mixtures thereof with di- and tripentaerythritol, and an aliphatic monocarboxylic acid containing from 1 to 20 carbon atoms, or mixtures of such acids.
  • An effective amount of ester in the lubricant for nitrile seal compatibility is an amount ranging from about 0.01 to 3.0 weight percent based on the weight of the oil composition. A preferred concentration is from 0.1 to 0.75 weight percent.
    • Seal Compatibility Tests
  • An important property of a lubricating oil additive and blended lubricating oil compositions containing the additive is the compatibility of the oil composition with the rubber seals employed in the engine. Some of the nitrogen containing succinimide dispersants and other additives such as active sulfur compounds employed in crankcase lubricating oil compositions may have the effect of seriously degrading the elastomer seals in internal combustion engines. In particular, such additives are known to attack rubber seals, such as nitrile rubber and fluorocarbon rubber seals which are commonly employed in internal combustion engines. This deterioration exhibits itself by sharply degrading the flexibility of the seals and in increasing their hardness. This is such a critical problem that a number of automotive engine builders
  • require that all crankcase lubricating oils pass a seal compatibility test before the oil composition will be rated acceptable for engine crankcase service. The seal compatibility tests used for nitrile rubbers are described below and are designed to determine the seal compatibility properties of a crankcase lubricating oil composition.
  • The test method for the Mercedes-Benz Seal Compatibility Test is based on the VDA 521-01 test procedure.
  • The seal compatibility test is conducted by soaking samples of the elastomer-rubber in the oil under investigation at an elevated temperature and then measuring the effect of the oil composition on the rubber sample for volume change, elongation change, hardness change and tensile strength change.
  • The specimens are weighed in air and in water to the nearest mg. After weighing in water, each specimen is dried on clean filter paper. The elongation and tensile strength of three of the specimens are measured.
  • The hardness of the specimens is determined with a durometer. The specimens conform to the standard S2 definition.
  • Six specimens are suspended in a beaker by inserting a piece of nichrome wire through the small hole in the end of each specimen. The specimens are arranged so that they do not touch each other or the beaker. The test oil is added in a ratio of 1:80 of elastomer to oil in the beaker. The elastomer specimens in the beaker are aged for 168 hours in an oven maintained at 100° C.
  • At the end of the test period, the beakers are removed from the oven and the specimens are removed from the beaker and cleaned with absorbent paper. Elongation and tensile strength measurements are made on each aged specimen. Each specimen is weighed in air and in water and measured for hardness.
  • Further details of seal compatibility test methods or nitrile elastomers required by Mercedes-Benz, CCMC and MAN are illustrated in the tables that follow.
    • Mercedes-Benz
  • Figure imgb0001
  • CCMC
    Figure imgb0002
  • M.A.N.
    Figure imgb0003
    Figure imgb0004
  • The following examples illustrate the practice of this invention.
    • EXAMPLE I
  • The base oil employed in this example was a refined oil (NMP SN 100/200) which was fully formulated with a conventional detergent-inhibitor package. The fully formulated oil (Oil 1) and a modification containing 0.55 weight percent glyceryl monooleate (Oil 2) were tested for their effect on a nitrile rubber (NBR-34 formulated from an acrylonitrile-butadiene copolymer containing about 34 percent of acrylonitrile) in the Mercedes-Benz Seal Compatibility Test. The percent change in tensile strength (TS) and in elongation (E) were reported.
    Figure imgb0005
  • Oil 2 containing the glyceryl monooleate exhibited excellent nitrile seal compatibility properties.
    • EXAMPLE II
  • A fully formulated lubricating oil composition designated as Oil 1 was employed in the CCMC Seal Test, the Mercedes-Benz Seal Test and the MAN Seal Test. Modifications of this oil, designated as Oil 2 containing 0.20 weight percent glyceryl monooleate and Oil 3 containing 0.55 weight percent glyceryl monooleate, which was supplied by C. P. Hall, were also employed in the CCMC Seal Test. The elastomer tested was a nitrile rubber. The test results are indicated in Table 2 below.
    Figure imgb0006
  • The additive oils of the invention containing glyceryl monooleate exhibited excellent improved nitrile seal compatibility properties.
    • EXAMPLE III
  • The lubricating oil employed in this example was a fully formulated gasoline engine oil and is designated as Oil 1. Oil 2 contains 0.20 weight percent of glyceryl monooleate, Oil 3 contains 0.55 weight percent of glyceryl monooleate and oil 4 contains 0.20 weight percent of Radiasurf 7150, another brand of glyceryl monooleate. These oils were tested in the Mercedes Benz Seal Test and the results are set forth in Table 3 below.
    Figure imgb0007
  • All of the oils containing the glyceryl monooleate exhibited excellent nitrile seal compatibility properties.
    • EXAMPLE IV
  • A commercial Ford Factory Fill lubricating oil composition was tested in the CCMC Seal Compatibility Test. A modified oil or variant was prepared containing 0.20 weight percent of glyceryl monooleate. A nitrile rubber was used in the test. The results are reported in Table 4 below.
    Figure imgb0008
  • The foregoing results demonstrate that the modified oil containing 0.20 percent of glyceryl monooleate gave excellent results in the CCMC Seal compatibility Test for the nitrile rubber.
    • EXAMPLE V
  • A variety of glycerol esters were tested in the same lubricating oil employed in Example II. In all cases, the glycerol ester was employed in a concentration of 0.20 weight percent. The following table lists the oils tested and the particular glycerol ester.
  • Oil No.
    • 1 Radiasurf 7150 Glyceryl Monooleate
    • 2 Radiasurf 7140 Glyceryl Monostearate, approx. 35% monoglycerides
    • 3 Radiasurf 7600 Glyceryl Monostearate, approx. 52% monoglycerides
    • 4 Radiasurf 7153 Glyceryl Monoricinoleate
    • 5 None (Ref. oil)
  • These oils were tested in a Mercedes-Benz Seal Compatibility Test and the results are set forth in Table 5 below.
    Figure imgb0009
  • The test results show that there is criticality in the nature of the glycerol ester. The esters formed from glycerol and a saturated fatty acid, namely glyceryl monostearate, fail to pass the test limits for the Mercedes-Benz Seal Compatibility Test while the oils containing a glycerol ester of an unsaturated fatty acid gave excellent nitrile seal compatibility properties.

Claims (7)

1. A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount effective to provide nitrile elastomer seal compatibility properties to the oil composition of an ester of glycerol and an unsaturated fatty acid having from 8 to 45 carbon atoms.
2. A composition as claimed in Claim 1 in which said ester is a mono-, di- or triester of glycerol or a mixture thereof.
3. A composition as claimed in Claim 1 or Claim 2 in which said ester is predominantly a monoester of glycerol.
4. A composition as claimed in Claim 1 in which said ester is glyceryl monooleate, glyceryl ricinoleate or glyceryl linoleate.
5. A composition according to any one of the preceding claims in which said lubricating oil composition contains from 0.01 to 3 weight percent of said glycerol ester.
6. The use of an ester of glycerol and an unsaturated fatty acid having from 8 to 45 carbon atoms in an oil of lubricating viscosity in order to provide nitrile elastomer seal compatibility properties.
7. The use of an ester of glycerol and an unsaturated fatty acid having from 8 to 45 carbon atoms to provide nitrile elastomer seal compatibility properties to a lubricating oil.
EP91302587A 1990-07-09 1991-03-25 Use of a particular ester Expired - Lifetime EP0466297B1 (en)

Applications Claiming Priority (2)

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US54977590A 1990-07-09 1990-07-09
US549775 1990-07-09

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EP0466297A1 true EP0466297A1 (en) 1992-01-15
EP0466297B1 EP0466297B1 (en) 1994-06-01

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025548A1 (en) * 1993-04-28 1994-11-10 Henkel Kommanditgesellschaft Auf Aktien Hydraulic oils having improved compatibility with seals
US5866520A (en) * 1996-01-31 1999-02-02 Chevron Chemical Company Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke cycle engines
US6087308A (en) * 1998-12-22 2000-07-11 Exxon Research And Engineering Company Non-sludging, high temperature resistant food compatible lubricant for food processing machinery
US6090761A (en) * 1998-12-22 2000-07-18 Exxon Research And Engineering Company Non-sludging, high temperature resistant food compatible lubricant for food processing machinery
WO2017205274A1 (en) * 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions

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US2493483A (en) * 1948-04-26 1950-01-03 Shell Dev Marine engine lubricant
FR1032168A (en) * 1950-04-06 1953-06-30 Standard Oil Dev Co Lubricating oil composition
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
FR2277882A1 (en) * 1974-07-11 1976-02-06 Chevron Res LONG LIFE FUNCTIONAL FLUID
GB2097813A (en) * 1981-05-06 1982-11-10 Exxon Research Engineering Co Glycerol esters in lubricating oils as fuel economy additives
EP0305538A1 (en) * 1987-03-02 1989-03-08 Idemitsu Kosan Company Limited Lubricating oil composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2493483A (en) * 1948-04-26 1950-01-03 Shell Dev Marine engine lubricant
FR1032168A (en) * 1950-04-06 1953-06-30 Standard Oil Dev Co Lubricating oil composition
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
FR2277882A1 (en) * 1974-07-11 1976-02-06 Chevron Res LONG LIFE FUNCTIONAL FLUID
GB2097813A (en) * 1981-05-06 1982-11-10 Exxon Research Engineering Co Glycerol esters in lubricating oils as fuel economy additives
EP0305538A1 (en) * 1987-03-02 1989-03-08 Idemitsu Kosan Company Limited Lubricating oil composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025548A1 (en) * 1993-04-28 1994-11-10 Henkel Kommanditgesellschaft Auf Aktien Hydraulic oils having improved compatibility with seals
US5866520A (en) * 1996-01-31 1999-02-02 Chevron Chemical Company Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke cycle engines
US6087308A (en) * 1998-12-22 2000-07-11 Exxon Research And Engineering Company Non-sludging, high temperature resistant food compatible lubricant for food processing machinery
US6090761A (en) * 1998-12-22 2000-07-18 Exxon Research And Engineering Company Non-sludging, high temperature resistant food compatible lubricant for food processing machinery
WO2017205274A1 (en) * 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
US11174449B2 (en) 2016-05-24 2021-11-16 The Lubrizol Corporation Seal swell agents for lubricating compositions

Also Published As

Publication number Publication date
DE69102217D1 (en) 1994-07-07
DE69102217T2 (en) 1994-09-15
EP0466297B1 (en) 1994-06-01

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