EP0275315B1 - Fluide lubrifiant synthetique - Google Patents

Fluide lubrifiant synthetique Download PDF

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Publication number
EP0275315B1
EP0275315B1 EP87903906A EP87903906A EP0275315B1 EP 0275315 B1 EP0275315 B1 EP 0275315B1 EP 87903906 A EP87903906 A EP 87903906A EP 87903906 A EP87903906 A EP 87903906A EP 0275315 B1 EP0275315 B1 EP 0275315B1
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Prior art keywords
fluid
traction
ester
synthetic lubricating
groups
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German (de)
English (en)
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EP0275315A1 (fr
EP0275315A4 (fr
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Narihiko Yoshimura
Hirotaka Tomizawa
Yasuji Komatsu
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Tonen General Sekiyu KK
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Tonen Corp
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    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—Esters of 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/06—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing propene
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/08—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing butene
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • C10M2205/0245—Propene used as base material
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C10M2205/0265—Butene used as base material
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
    • 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
    • C10M2207/284—Esters of aromatic monocarboxylic acids
    • C10M2207/2845—Esters of aromatic monocarboxylic acids used as base material
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • This invention relates to a synthetic lubricating fluid comprising a monoester compound of cyclohexanol with cyclohexanecarboxylic acid, or said ester and a branched poly- ⁇ -olefin incorporated therein.
  • Traction drive power transmissions which transmit power to a driven part through a traction drive mechanism have attracted attention in the field of automobiles and industrial machinery, and in recent years extensive research and development has been conducted in this area.
  • the traction drive mechanism is a power transmitting mechanism. Unlike conventional drive mechanisms, it does not use any gears. This results in a reduction in vibration and noise as well as a smooth speed change in high-speed rotation.
  • An important goal in the automobile industry is an improvement in the fuel consumption of automobiles. It has been suggested that if the traction drive is applied to the transmission of automobiles in order to convert the transmission to a continuous variable-speed transmission the fuel consumption can be reduced by at least 20% compared with conventional transmission systems. This is due to the fact that the drive can always be in the optimum fuel consumption region of an engine.
  • traction coefficient is defined as the ratio of the tractional force which is caused by slipping at the contact points between rotators which are in contact with each other in a power transmission of the rolling friction type to the normal load.
  • a traction fluid must be comprised of a lubricating oil having a high traction coefficient. It has been confirmed that a traction fluid possessing a molecular structure having a naphtene ring exhibits a high performance. "Santotrack®,” manufactured by the Monsanto Chemical Company, is widely known as a commercially available traction fluid. Japanese Patent Publication No. 35763/1972 discloses di(cyclohexyl)alkane and dicyclohexane as traction fluids having a naphthene ring.
  • US-A-3440894 further lists a wide range of lubricating oils suitable for use as traction fluids, which comprise inter alia, esters of cycloalkane alkanoic acids with cycloalkanols, but does not compare the relative merits of the different types of cycloalkane esters disclosed.
  • the present inventors have made extensive and intensive studies to develop a traction fluid which not only exhibits a high traction coefficient but is also inexpensive. As a result, the present inventors have discovered that the incorporation of an ester having two cyclohexyl rings or its derivative, or said ester in combination with a branched poly- ⁇ -olefin, can provide an economical, high performance base oil fluid.
  • the present invention is based on this discovery.
  • a synthetic lubricating fluid comprising an ester compound or its derivative of cyclohexanol with cyclohexanecarboxylic acid, represented by the following general formula wherein n is an integer of 0 to 5 and m is an integer of 0 to 5, provided that n + m is 1 to 10, each R1 may be the same or different and are each a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and each R2 may be the same or different and is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • a synthetic lubricating fluid comprising the above-mentioned ester compound or its derivative of cyclohexanol with cyclohexanecarboxylic acid and 1 to 70% by weight of a branched poly- ⁇ -olefin.
  • a first object of the present invention is to provide a synthetic lubricating fluid having excellent properties.
  • a second object of the present invention is to provide a synthetic lubricating fluid which is not only economical but also readily available and easily applicable to transmissions.
  • the traction fluid of the present invention comprises an ester or its derivative having two cyclohexyl rings at both ends (hereinafter often referred to as “component A”), or said ester and a specific amount of a branched poly- ⁇ -olefin (hereinafter often referred to as “component B").
  • component A an ester or its derivative having two cyclohexyl rings at both ends
  • component B a specific amount of a branched poly- ⁇ -olefin
  • the component A is an ester represented by the above structural formula.
  • n is an integer of 0 to 5 and m is an integer of 0 to 5, provided that n + m is 1 to 10.
  • n is preferably an integer of 1 to 3, while m is preferably an integer of 1 to 3.
  • R1 is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms and is preferably a hydrogen atom or a methyl group.
  • R2 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms and is preferably a hydrogen atom.
  • R1 is an alkyl group having 9 or more carbon atoms or when R2 is an alkyl group having 4 or more carbon atoms the fluid is not only susceptible to decomposition but also has a viscosity which is too high.
  • the esters or their derivatives have a viscosity of 5 to 50 X10 ⁇ 6 M2/S (cst), particularly preferably 10 to 30 X10 ⁇ 6 M2/S (cst) at 40°C and 1 to 10 X10 ⁇ 6 M2/S (cst), particularly preferably 2 to 5 X10 ⁇ 6 M2/S (cst) at 100°C.
  • Examples of the derivatives of the esters include their amination products and ether compounds.
  • the ester can be produced by the following method. Specifically, the ester is produced by the esterification reaction of a monohydric alcohol with a cyclohexanecarboxylic acid compound.
  • the monohydric alcohol compound is a compound having a cyclohexyl ring and is represented by the following structural formula: wherein R1 is independently selected from hydrogen and alkyl groups having 1 to 8 carbon atoms. R2 is independently selected from hydrogen or an alkyl group having 1 to 3 carbon atoms, and m is an integer of 0 to 5.
  • a particularly preferred monohydric alcohol is a compound in which R1 is hydrogen or an alkyl group having 1 to 4 carbon atoms, R2 is hydrogen or a methyl group, and m is an integer of 0 to 2.
  • cyclohexanol examples include cyclohexanol, methylcyclohexanol, and cyclohexylcarbinol.
  • the cyclohexanecarboxylic acid is a compound represented by the following structural formula: wherein R1 is independently selected from hydrogen and alkyl groups having 1 to 8 carbon atoms. R2 is independently selected from hydrogen or an alkyl group having 1 to 3 carbon atoms, and n is an integer of 0 to 5.
  • a particularly preferred carboxylic acid is a compound in which R1 is hydrogen or an alkyl group having 1 to 4 carbon atoms, R2 is hydrogen or a methyl group, and n is an integer of 0 to 2.
  • Examples of the carboxylic acid compounds include cyclohexanecarboxylic acid, cyclohexylacetic acid and cyclohexylpropionic acid.
  • the esterification reaction is conducted in the presence of an excess amount of the alcohol using a catalyst, such a phosphoric acid, or in the presence of an excess amount of the acid. It is preferred that the esterification reaction be conducted in the presence of an excess amount of the acid.
  • 1 mol of the alcohol compound is reacted with 1.2 to 2 mol (particularly preferably 1.5 to 1.8 mol of the acid.
  • the reaction temperature is about 150 to 250°C, preferably 170 to 230°C, and the reaction time is 10 to 40 hr, preferably 15 to 25 hr.
  • the esterification reaction may be conducted under either elevated or reduced pressures it is preferred that the reaction be conducted at atmospheric pressure from the standpoint of ease of reaction operation. Under this condition the excess acid serves as a catalyst.
  • An alkylbenzene such as xylene or toluene can be added in a suitable amount as a solvent. The addition of the solvent enables the reaction temperature to be easily controlled.
  • water which has been formed during this reaction evaporates. The reaction is terminated when an equimolar amount, with respect to the alcohol, of the water, has evaporated. The excess acid is neutralized with an aqueous alkaline solution and removed by washing with water.
  • Phosphoric acid p-toluenesulfonic acid, sulfuric acid, or the like, is used as the catalyst.
  • the most preferred catalyst is phosphoric acid because it enhances the reaction rate and increases the yield of the ester.
  • the reaction product is finally distilled under reduced pressure to remove water and the solvent, thereby obtaining the ester compound of the present invention.
  • the ester itself of the present invention exhibits a high traction coefficient. However, it may be blended with a second component, e.g., a poly- ⁇ -olefin such as polybutene or other ester, which provides as further improved traction fluid.
  • a second component e.g., a poly- ⁇ -olefin such as polybutene or other ester, which provides as further improved traction fluid.
  • the poly- ⁇ -olefin as the second component has either a quaternary carbon atom or a tertiary carbon atom in its main chain and is a polymer of an ⁇ -olefin having 3 to 5 carbon atoms or the hydrogenation product thereof.
  • the poly- ⁇ -olefins include polypropylene, polybutene, polyisobutylene and polypentene and the hydrogenation products thereof. Particularly preferred are polybutene and polyisobutylene and the hydrogenation products thereof.
  • the polyisobutylene is represented by the following structural formula:
  • the hydrogenation product of the polyisobutylene is represented by the following structural formula: In the above formulae the degree of polymerization, n, is 5 to 200.
  • polybutene and polyisobutylene are commercially available, they may also be produced by conventional polymerization methods.
  • the hydrogenation product thereof is produced by reacting polyisobutylene or the like in the presence of hydrogen.
  • the molecular weight of the poly- ⁇ -olefin is preferably in the range of 300 to 10,000, more preferably 500 to 5,000 and especially preferably 900 to 5,000.
  • the molecular weight can be adjusted by suitable methods such as decomposition of a poly- ⁇ -olefin having a high molecular weight and mixing of poly- ⁇ -olefins having different molecular weights.
  • OCP ⁇ -olefin copolymer
  • ester B an ester having at least two cyclohexyl and 1 to 3 ester linkages
  • ester B examples include a monoester, diester, or triester, obtained by the esterification of a cyclohexanol compound with a carboxylic acid.
  • a particularly preferred ester B is a monoester or diester having 1 to 10 carbon atoms in its center and having one cyclohexyl ring at each end.
  • the ester of the present invention e.g. a monoester of cyclohexylacetic acid with cyclohexyl carbinol, exhibits a traction coefficient of 0.104 to 0.106; the component B, e.g., polybutene, exhibits a traction coefficient of 0.075 to 0.085; and the ester B (a monoester of cyclohexanecarboxylic acid with cyclohexanol) exhibits a traction coefficient of 0.090 to 0.092.
  • the ester (first component) of the present invention exhibits a high traction coefficient
  • its use alone in a traction drive device results in a high performance.
  • a further improved traction fluid can be obtained by blending with sais first component 0.1 to 95% by weight, particularly 1 to 70% by weight, and especially preferably 10 to 50% by weight, of the second component comprised of a poly- ⁇ -olefin or ester B.
  • the traction coefficient of the second component is equal to or lower than that of component A
  • the gem-dialkyl group or cyclohexyl ring of the second component cooperates with the cyclohexyl of the first component to produce a synergistic effect with respect to improvement in the traction coefficient.
  • the second component is relatively inexpensive and has excellent viscosity characteristics, a traction fluid can be economically obtained by blending the first component with 0.1 to 95% by weight of the second component without lowering the traction coefficient.
  • additives may also be added to the traction fluid of the present invention depending on its applications. Specifically, when the traction device operates at high temperatures and large loads, at least one additive selected from among an antioxidant, a wear inhibitor, and a corrosion inhibitor, may be added in an amount of 0.01 to 5% by weight. Similarly, when a high viscosity index is required a known viscosity index improver is added in an amount of 1 to 10% by weight. However, since the use of polyacrylate and olefin copolymer unfavorably lowers the traction coefficient, if they are present it is preferred that they be used in an amount of 4% by weight or less.
  • synthetic lubricating fluid or traction fluid as employed in the present invention is intended to mean a fluid used in devices which transmit a rotational torque through spot contact or line contact, or used in transmissions having a similar structure.
  • the synthetic lubricating fluid of the present invention exhibits a traction coefficient higher than those of conventionally known fluids, i.e., exhibits a traction coefficient by 5 to 15% higher than those of the conventional fluids, although the value varies depending on the viscosity. Therefore, the synthetic lubricating fluid of the present invention can be advantageously used for relatively low power drive transmissions including internal combustion engines of small passenger cars, spinning machines and food producing machines, as well as large power drive transmissions such as industrial machines, etc.
  • the synthetic lubricating fluid of the present invention is remarkably superior in its traction coefficient over conventional fluids.
  • the reason why the traction fluid of the present invention exhibits a high traction coefficient is not yet fully understood. However, basically, the reason is believed to be in the unique molecular structure of the synthetic lubricating fluid of the present invention.
  • the synthetic lubricating fluid (first component) of the present invention is an ester having two cyclohexyl rings in its molecule.
  • the ester linkages bring about an interdipolar force between the molecules. It is believed that the interdipolar force serves to bring the fluid into a stable glassy state under high load conditions, thereby increasing the shearing force.
  • this second component possesses a gem-dialkyl quaternary carbon atom or a cyclohexyl ring.
  • Ester A1 according to the present invention was synthesized by the following method. Cyclohexylacetic acid and cyclohexylcarbinol (in 3:1 mole ratio) were charged into a reactor, followed by the addition of 6 g of phosphoric acid as a solvent. The reactor was then heated to 200°C, and the contents of the reactor were allowed to react under atmospheric pressure. The heating was stopped at a point when the amount of water generated during the reaction was twice by mol the amount of the cyclohexylacetic acid.
  • the reaction mixture was washed with an alkaline solution to remove unreacted compounds, i.e., cyclohexylacetic acid and cyclohexylcarbinol, from a mixture of the reaction product i.e., an ester of cyclohexylacetic acid with cyclohexylcarbinol, and the unreacted compounds, followed by vacuum distillation, thereby isolating a pure ester A1.
  • esters A2 and A3 of the present invention were synthesized using the following raw materials:
  • the traction coefficients of the following were determined: neat esters A1 A2 and A3; and blends of these esters with (i) hydrogenated polybutene (B1) having an average molecular weight of 1350, (ii) polybutene (B2) having an average molecular weight of 900, and (iii) polybutene (B3) having an average molecular weight of 2350 or polybutene (B4) having an average molecular weight of 420.
  • the measurement conditions for determining the traction coefficient are shown below.
  • the synthetic lubricating fluids of this invention are superior in traction performance to the conventional fluids tested.
  • traction coefficients of a traction fluid consisting of neat polybutene (i.e., 100 weight percent) and a commercially available traction fluid were measured under the same conditions as described in the above Examples.
  • the present invention is directed to a synthetic lubricating fluid containing a base oil comprised of an ester having two cyclohexyl rings, or said ester and a specific amount of a poly- ⁇ -olefin blended therewith.
  • the synthetic lubricating oil not only exhibits an extremely high traction coefficient but is also inexpensive and has excellent viscosity characteristics.
  • the use of the traction fluid of the present invention in a power transmission, particularly a traction drive device leads to a remarkable increase in shearing force under a high load. This enables the reduction in size of the device resulting in a reduction in cost of said device.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Abstract

Fluide lubrifiant synthétique préparé par formulation d'un composé de cyclohexanecarboxylate de cyclohexyle représenté par la formule générale (I) (dans laquelle n et m représentent chacun un entier de 0 à 5, à condition que la somme de n et de m soit comprise entre 1 et 10; les groupes R1 peuvent être identiques ou différents et chacun représente un atome d'hydrogène ou un groupe alkyle possédant de 1 à 8 atomes de carbone, et les groupes R2 peuvent être identiques ou différents et chacun représente un atome d'hydrogène ou un groupe alkyle possédant de 1 à 3 atomes de carbone), ou bien son dérivé. Ce fluide lubrifiant synthétique et de préférence utilisé dans les dispositifs de transmission de puissance, notamment dans les dispositifs d'entraînement par traction.

Claims (11)

1. Fluide lubrifiant synthétique, comprenant au moins un ester, ou son dérivé, représenté par la formule
Figure imgb0008
 dans laquelle
   n représente un nombre entier de 0 à 5 et m représente un nombre entier de 0 à 5, sous réserve que la somme n + m soit égale à une valeur de 1 à 10,
   les groupes R₁, qui peuvent être identiques ou différents, sont choisis chacun indépendamment entre l'hydrogène et des groupes alkyle en C₁ à C₈, et
   les groupes R₂, qui peuvent être identiques ou différents, sont choisis chacun indépendamment entre l'hydrogène et des groupes alkyle en C₁ à C₃.
2. Fluide suivant la revendication 1, dans lequel n représente un nombre entier de 1 à 3.
3. Fluide suivant la revendication 1, dans lequel m représente un nombre entier de 1 à 3.
4. Fluide suivant la revendication 1, dans lequel les groupes R₁ sont choisis indépendamment entre l'hydrogène et des groupes alkyle en C₁ à C₄.
5. Fluide suivant la revendication 1, dans lequel les groupes R₂ sont choisis indépendamment entre l'hydrogène et des groupes méthyle.
6. Fluide lubrifiant synthétique suivant l'une quelconque des revendications 1 à 5, comprenant en outre 1 à 70 % en poids d'au moins une poly-α-oléfine ramifiée ou de son produit d'hydrogénation.
7. Fluide suivant la revendication 6, dans lequel la poly-α-oléfine possède un poids moléculaire moyen de 500 à 10 000.
8. Fluide suivant la revendication 6 ou la revendication 7, dans lequel la poly-α-oléfine possède un poids moléculaire moyen de 900 à 5000.
9. Fluide suivant l'une quelconque des revendications 6 à 8, qui contient 10 à 50 % en poids de la poly-α-oléfine.
10. Fluide suivant l'une quelconque des revendications 1 à 9, contenant au moins un additif choisi entre un anti-oxydant, un agent anti-usure, un inhibiteur de corrosion et un agent améliorant l'indice de viscosité.
11. Utilisation d'un fluide suivant la revendication 1, comme fluide lubrifiant ou fluide de traction.
EP87903906A 1986-06-10 1987-06-10 Fluide lubrifiant synthetique Expired - Lifetime EP0275315B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP134401/86 1986-06-10
JP61134401A JPH0774351B2 (ja) 1986-06-10 1986-06-10 合成潤滑フル−ド

Publications (3)

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EP0275315A1 EP0275315A1 (fr) 1988-07-27
EP0275315A4 EP0275315A4 (fr) 1988-10-24
EP0275315B1 true EP0275315B1 (fr) 1992-03-11

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EP (1) EP0275315B1 (fr)
JP (1) JPH0774351B2 (fr)
CA (1) CA1293499C (fr)
DE (1) DE3777375D1 (fr)
WO (1) WO1987007636A1 (fr)

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Publication number Priority date Publication date Assignee Title
JPH086109B2 (ja) * 1987-04-01 1996-01-24 東燃料株式会社 トラクシヨン流体
WO1989002911A1 (fr) * 1987-09-25 1989-04-06 Toa Nenryo Kogyo Kabushiki Kaisha Fluide de traction ameliore
US5318711A (en) * 1993-01-21 1994-06-07 Quaker Chemical Corporation Method for lubricating metal-metal contact systems in metalworking operations with cyclohexyl esters
US6372696B1 (en) 1999-11-09 2002-04-16 The Lubrizol Corporation Traction fluid formulation
BRPI0808844A2 (pt) * 2007-03-13 2018-10-23 Lubrizol Corp composição lubrificante adequada para lubrificar uma transmissão e método para lubrificar a mesma

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Publication number Priority date Publication date Assignee Title
US3440894A (en) * 1966-10-13 1969-04-29 Monsanto Co Tractants and method of use
US3803037A (en) * 1970-04-07 1974-04-09 Monsanto Co Lubricants having improved load-bearing properties
DE2713440A1 (de) * 1977-03-26 1978-09-28 Bayer Ag Carbonsaeureester, deren herstellung und verwendung als basisschmieroel
JPS59191797A (ja) * 1983-04-14 1984-10-30 Nippon Petrochem Co Ltd トラクシヨンドライブ用流体
JPS619497A (ja) * 1984-06-25 1986-01-17 Nippon Oil Co Ltd 自動変速機油組成物
JP2714332B2 (ja) * 1992-10-07 1998-02-16 株式会社東芝 データ記録再生装置およびディスク固定方法

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Publication number Publication date
CA1293499C (fr) 1991-12-24
JPS62290796A (ja) 1987-12-17
EP0275315A1 (fr) 1988-07-27
DE3777375D1 (de) 1992-04-16
EP0275315A4 (fr) 1988-10-24
WO1987007636A1 (fr) 1987-12-17
JPH0774351B2 (ja) 1995-08-09

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