EP0275315A1 - Fluide lubrifiant synthetique - Google Patents

Fluide lubrifiant synthetique Download PDF

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Publication number
EP0275315A1
EP0275315A1 EP87903906A EP87903906A EP0275315A1 EP 0275315 A1 EP0275315 A1 EP 0275315A1 EP 87903906 A EP87903906 A EP 87903906A EP 87903906 A EP87903906 A EP 87903906A EP 0275315 A1 EP0275315 A1 EP 0275315A1
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EP
European Patent Office
Prior art keywords
fluid
traction
ester
integer
hydrogen
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German (de)
English (en)
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EP0275315B1 (fr
EP0275315A4 (fr
Inventor
Narihiko Yoshimura
Hirotaka Tomizawa
Yasuji Komatsu
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Tonen General Sekiyu KK
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Tonen Corp
Toa Nenryo Kogyyo KK
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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 arid, 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 he comprised of a lubricating oil having a high traction coefficient. It has been confirmed that a traction fluid possessing a molecular structure having a naphthene 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. This patent publication discloses that a fluid obtained by incorporating the above-mentioned alkane compound in a perhydrogenated (a -methyl)styrene polymer, hydrindane compound.
  • Japanese Patent Laid-Open No. 191797/1984 discloses a traction fluid containing an ester compound having a naphthene ring. It discloses that an ester obtained by the hydrogenation of the aromatic nucleus of dicyclohexyl cyclohexanedicarboxylate or dicyclohexyl phthalate is a preferred traction fluid.
  • 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 R 1 may be the same or different. and are each a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and each R 2 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 derivat ive 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").
  • 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.
  • R 1 is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms and is preferably -a hydrogen atom or a methyl group.
  • R 2 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms and is preferably a hydrogen atom.
  • R is an alkyl group having 0 or more carbon atoms or when R 2 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 cst. particularly preferably 10 to 30 cst at 40°C and 1 to 10 est, particularly preferably 2 to 5 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 hy the following strurtural formula: wherein R 1 is independently selected from hydrogen and alkyl groups having 1 to 4 carbon atoms, R 2 is independently selected from hydrogen or an alkyl group having 1 to 8 carbon atoms, and m is an integer of 0 to 5.
  • a particularly preferred monohydric alcohol is a compound in which R 1 is hydrgen or a methyl group, R 2 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and m is an integer of 0 to 2.
  • examples of such a compound include cyclohexanol, methylcyclohexanol. and cyclohexylcarbinol.
  • the cyclohexanecarboxylic acid is a. compound represented by the following structural formula: wherein R 1 is independently selected from hydrogen and alkyl groups having 1 to 4 carbon atoms, R 2 is independently selected from hydrogen or an alkyl group having 1 to 8 carbon atoms, and n is an integer of 0 to 5.
  • a particularly preferred carboxylic acid is a compound in which R 1 is hydrogen or a methyl group.
  • R 2 is hydrogen or an alkyl group having 1 to 4 carbon atoms-, and n is an integer of 0 to 2.
  • 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 as 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.
  • 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 he 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. As the reaction proceeds.
  • the ester itself of the present invention exhibits a high traction coefficient. However, it may he blended with a second component, e.g., a poly- ⁇ -olefin such as polybutene. or other ester, which provides a further improved traction fluid.
  • a second component e.g., a poly- ⁇ -olefin such as polybutene. or other ester, which provides a further improved traction fluid.
  • the puly- ⁇ -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 hy reacting polyisobutylene or the like in the presence of hydrogen.
  • the molecular weight of f the poly ⁇ olefin is preferably in the range of 300 to 10.000, more preferably in the range of 500 to 5.000.
  • the molecular weight can be adjusted by suitable methods such as decomposition of a poly a -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 rings 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 0.100: 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 0.000 to 0.002.
  • 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 said first component 0.1 to 95% by weight, particularly 10 to 70% 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 ring 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 coeffifient.
  • 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 inhihitor, and a corrosion inhibitor, may be added in an amount of 0.01 t.o 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 believad 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 At 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 arid 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 A 1 .
  • an alkaline solution to remove unreacted compounds, i.e., cyclohexylacetic arid 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 A 1 .
  • esters A 2 and A3 of the present invention were synthesized using the following raw materials:
  • the traction coefficients of the following were determined: neat esters A 1 A 2 and A 3 ; and blends of these esters with (i) hydrogenated polybutene (B 1 ) having an average molecular weight of 1350, (ii) polybutene (B z ) having an average molecular weight of 900, and (iii) polybutene (B 3 ) having an average molecular weight of 2350 or polybutene (B 4 ) 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-a -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.
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)

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

Family

ID=15127527

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87903906A Expired - Lifetime EP0275315B1 (fr) 1986-06-10 1987-06-10 Fluide lubrifiant synthetique

Country Status (5)

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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339088A1 (fr) * 1987-09-25 1989-11-02 Tonen Corporation Fluide de traction ameliore
WO2001034738A2 (fr) * 1999-11-09 2001-05-17 The Lubrizol Corporation Formule de fluide de traction
WO2008112724A2 (fr) * 2007-03-13 2008-09-18 The Lubrizol Corporation Fluide de transmission multifonctionnel

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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
US5318711A (en) * 1993-01-21 1994-06-07 Quaker Chemical Corporation Method for lubricating metal-metal contact systems in metalworking operations with cyclohexyl esters

Citations (3)

* Cited by examiner, † Cited by third party
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
FR2384739A1 (fr) * 1977-03-26 1978-10-20 Bayer Ag Esters d'acide carboxylique, procede de leur preparation et leur emploi comme huile lubrifiante de base

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
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
FR2384739A1 (fr) * 1977-03-26 1978-10-20 Bayer Ag Esters d'acide carboxylique, procede de leur preparation et leur emploi comme huile lubrifiante de base

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO8707636A1 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339088A1 (fr) * 1987-09-25 1989-11-02 Tonen Corporation Fluide de traction ameliore
EP0339088A4 (fr) * 1987-09-25 1989-12-28 Toa Nenryo Kogyo Kk Fluide de traction ameliore.
WO2001034738A2 (fr) * 1999-11-09 2001-05-17 The Lubrizol Corporation Formule de fluide de traction
WO2001034738A3 (fr) * 1999-11-09 2002-01-10 Lubrizol Corp Formule de fluide de traction
US6372696B1 (en) 1999-11-09 2002-04-16 The Lubrizol Corporation Traction fluid formulation
WO2008112724A2 (fr) * 2007-03-13 2008-09-18 The Lubrizol Corporation Fluide de transmission multifonctionnel
WO2008112724A3 (fr) * 2007-03-13 2008-11-20 Lubrizol Corp Fluide de transmission multifonctionnel

Also Published As

Publication number Publication date
JPS62290796A (ja) 1987-12-17
JPH0774351B2 (ja) 1995-08-09
EP0275315B1 (fr) 1992-03-11
EP0275315A4 (fr) 1988-10-24
DE3777375D1 (de) 1992-04-16
WO1987007636A1 (fr) 1987-12-17
CA1293499C (fr) 1991-12-24

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