EP0748863A2 - Composition de fluide de traction - Google Patents

Composition de fluide de traction Download PDF

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Publication number
EP0748863A2
EP0748863A2 EP96109344A EP96109344A EP0748863A2 EP 0748863 A2 EP0748863 A2 EP 0748863A2 EP 96109344 A EP96109344 A EP 96109344A EP 96109344 A EP96109344 A EP 96109344A EP 0748863 A2 EP0748863 A2 EP 0748863A2
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EP
European Patent Office
Prior art keywords
component
hydrogenated product
compound
traction drive
cyclohexyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP96109344A
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German (de)
English (en)
Other versions
EP0748863A3 (fr
Inventor
Yasuyuki c/o Cosmo Research Institute Sakata
Natsuhito c/o Cosmo Research Institute Soga
Toshio c/o Cosmo Research Institute Kunoki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cosmo Oil Co Ltd
Cosmo Research Institute
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Cosmo Oil Co Ltd
Cosmo Research Institute
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Publication date
Application filed by Cosmo Oil Co Ltd, Cosmo Research Institute filed Critical Cosmo Oil Co Ltd
Publication of EP0748863A2 publication Critical patent/EP0748863A2/fr
Publication of EP0748863A3 publication Critical patent/EP0748863A3/fr
Withdrawn legal-status Critical Current

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Definitions

  • the present invention relates to a traction drive fluid composition exhibiting a high traction coefficient over a wide temperature range and excellent friction characteristics.
  • a traction drive device is a power transmission utilizing rolling-sliding friction induced by resistance against a shear produced by the hardening of a fluid oil film when the oil present in a cylindrical or conical rolling body loses fluidity.
  • the traction drive device is widely used for continuously variable transmission for automobiles, continuously variable transmission for industrial vehicles, and for hydraulic equipment.
  • demand for a traction drive fluid exhibiting high traction performance has increased.
  • a traction drive device In addition to a traction drive main body, a traction drive device includes a torque converter, an oil hydraulic mechanism, a wet clutch, and the like.
  • the traction drive fluid for lubricating these parts must have excellent viscosity characteristics, friction characteristics, wear resistance, anti-seizure characteristics, corrosion resistance, low temperature fluidity, oxidation stability, rust prevention characteristics, sealing compatibility, anti-foaming characteristics, and shear stability, in addition to the above-mentioned high traction performance.
  • a thermal copolymerization product of a cyclopentadiene compound and an ⁇ -olefin compound to a composition which comprises trimers, tetramers, pentamers, and hexamers of cyclopentadiene as major components.
  • Japanese Patent Application Laid-Open No. 230696/1989 discloses that homopolymers of cyclopentadiene have a greater effect than copolymers of cyclopentadienes and other compounds and that only olefins or diens of aliphatic hydrocarbons can be used as the compounds to be copolymerized with cyclopentadiene.
  • a traction drive device in automobiles is being studied because of its excellent characteristics in saving fuel consumption. Because the traction drive for automobiles is used over a wide temperature range, the traction drive fluid used for lubricating such a traction drive device must ensure excellent cold startability of that device. In addition, because the traction drive fluid is used for controlling the oil pressure, the fluid must have the characteristics required for a hydraulic oil. Specifically, putting emphasis on the viscosity at low temperatures, viscosity-temperature performance and low temperature fluidity are the characteristics which must be improved.
  • the lock-up mechanism is a mechanism for transmitting the engine output directly to the traction drive in accordance with running conditions.
  • Introduction of a slip control using a lock-up clutch in a low-speed range is anticipated for improvement of fuel consumption at low speeds.
  • Operation of the lock-up mechanism low speeds may induce vibration of a chassis, a phenomenon called "shudder".
  • a lubricating oil with an excellent ⁇ (friction coefficient)-V (sliding speed) characteristic is required to suppress the shudder.
  • An object of the present invention is therefore to provide a traction drive fluid composition having excellent friction characteristics and a traction coefficient which is high at a temperature of about 30°C but does not decrease at high temperatures.
  • the inventors of the present invention have conducted extensive studies to develop a traction drive fluid composition having a high traction coefficient at high temperatures and found that a composition comprising the following compounds (A-1) or (A-2) or both, as a component (A), and a thermally copolymerized product (hereinafter called "heat copolymer") of a cyclopentadiene compound and a vinyl aromatic hydrocarbon compound or a hydrogenated product thereof having a softening point of about 40°C or higher or a weight average molecular weight of 250 or larger, as a component (B) at a weight ratio (A)/(B) of 85/15 to 97/3, or a composition comprising the components (A) and (B) at a weight ratio (A)/(B) of less than 85/15 and a hereinafter described component (C) with a viscosity lower than that of the component (A), exhibits excellent temperature characteristics and excellent low temperature fluidity due to a synergistic effect of these components.
  • the inventors have further found that the friction characteristics of the composition is improved by the addition of at least one phosphorous compound, as a component (D), and at least one friction modifier, as a component (E).
  • a specific object of the present invention is to provide a traction drive fluid composition
  • a traction drive fluid composition comprising the following component (A) and component (B) at a weight ratio (A)/(B) of 85/15 to 97/3:
  • the above composition further comprises 0.01-5.0% by weight of the component (D) which is at least one compound selected from a phosphate, an acidic phosphate, a phosphite, and an acidic phosphite, and 0.01-3.0% by weight of the component (E) which is an N-type friction modifier or an ester-type friction modifier.
  • component (D) which is at least one compound selected from a phosphate, an acidic phosphate, a phosphite, and an acidic phosphite
  • component (E) which is an N-type friction modifier or an ester-type friction modifier.
  • Figure 1 shows the traction coefficients ( ⁇ ) at various temperatures of the traction drive fluid compositions prepared in Examples 1-3 and Comparative Examples 1-4.
  • Figure 2 shows the traction coefficients ( ⁇ ) at various temperatures of the traction drive fluid compositions prepared in Examples 4 and 5.
  • Figure 3 shows the traction coefficient ( ⁇ ) at various temperatures of the traction drive fluid composition prepared in Example 6.
  • C 1 -C 3 alkyl groups in the present invention are methyl, ethyl, n-propyl, and i-propyl groups.
  • the hydrogen atoms bonded to cyclic hydrocarbon structures are omitted.
  • R 1 to R 10 in the formulas (A-1) or (A-2) are preferably hydrogen, a methyl group, or an ethyl group, with the hydrogen or methyl group being particularly preferred.
  • the compound with an alkylated carbon atom adjacent to the cyclohexyl group is particularly preferred.
  • the compounds with an integer from 0 to 2 for n1 to n4 in the formulas (A-1) or (A-2) are particularly preferred.
  • Q 1 to Q 4 when these are present, are normally a methyl group.
  • the compounds of the formulas (A-1) or (A-2) are 1,2-dicyclohexylpropane, 1,2-dicyclohexyl-2-methylpropane, 2,3-dicyclohexylbutane, 2,3-dicyclohexyl-2-methylbutane, 2,3-dicyclohexyl-2,3-dimethylbutane, 1,3-dicyclohexylbutane, 1,3-dicyclohexyl-3-methylbutane, 2,4-dicyclohexylpentane, 2,4-dicyclohexyl-2-methylpentane, 2,4-dicyclohexyl-2,4-dimethylpentane, 1,3-dicyclohexyl-2-methylbutane, 2,4-dicyclohexyl-2,3-dimethylbutane, and 2,4-dicyclohexyl-2,3-dimethylpentane.
  • the compounds having a substituted ethyl, n-propyl, i-propyl, or cyclohexyl group for the methyl group in the above-listed compounds and the compounds having one or more optional positions in the cyclohexyl ring of the above listed compounds alkylated with a methyl, ethyl, n-propyl, i-propyl, or cyclohexyl group.
  • Either of the compounds of the formulas (A-1) or (A-2) may be used individually, or a mixture of a compound of the formula (A-1) and a compound of the formula (A-2) at an arbitrary proportion may be used.
  • a hydrogenated dimer of ⁇ -alkylstyrene which is one of the compounds of component (A) can be prepared by dimerization of ⁇ -alkylstyrene followed by hydrogenation of the resulting dimer.
  • the dimerization and the hydrogenation can be carried out by any optional method with no specific limitations.
  • the dimerization of ⁇ -methylstyrene can be carried out in the presence of a catalyst, typically an acidic catalyst, with an addition of a solvent, a reaction controlling agent, and the like, as required.
  • a catalyst typically an acidic catalyst
  • the acidic catalyst include clays such as activated clay or acid clay; mineral acids such as sulfuric acid, hydrochloric acid, or hydrofluoric acid; organic acids such as p-toluenesulfonic acid or triflic acid; Lewis acids such as aluminum chloride, ferric chloride, stannic chloride, boron trifluoride, boron tribromide, aluminum bromide, gallium chloride, and gallium bromide; and solid acids such as zeolite, silica, alumina, silica ⁇ alumina, cationic exchange resins, and heteropoly acids.
  • the amount of acidic catalyst used is usually 0.1-100% by weight, preferably 1-20% by weight, of the ⁇ -methylstyrene, but not specifically limited to these ranges.
  • a saturated hydrocarbon may be used as the solvent. Specific examples include n-pentane, n-hexane, heptane, octane, nonane, decane, cyclopentane, cyclohexane, methylcyclohexane, and decaline.
  • a reaction controlling agent is used with the object of increasing the selectivity of the dimer produced in the reaction.
  • reaction controlling agent examples include carboxylic acids such as acetic acid; acid anhydrides such as acetic anhydride and phthalic anhydride; cyclic esters such as ⁇ -butyrolactone and valerolactone; glycols such as ethylene glycol; mono-nitro compounds such as nitromethane and nitrobenzene; esters such as ethyl acetate; ketones such as mesityl oxide; aldehydes such as formalin and acetaldehyde; cellosolves; and polyalkylene glycol alkyl ethers such as diethylene glycol monoethyl ether.
  • the dimerization reaction is carried out at a temperature of -30°C to 180°C, and preferably 0°C to 160°C.
  • the hydrogenation of the ⁇ -methylstyrene dimer thus produced can also be carried out in the presence of a catalyst, with the addition of a solvent or the like as required.
  • a catalyst commonly known as a hydrogenation catalyst containing one or more metals such as nickel, ruthenium, palladium, platinum, rhodium, iridium, copper, chromium, molybdenum, cobalt, and tungsten can be used as the catalyst.
  • the amount of the catalyst used is usually 0.1 to 100% by weight, preferably 1 to 20% by weight, of the dimer, but not specifically limited to these ranges.
  • a liquid saturated hydrocarbon such as n-pentane, n-hexane, heptane, octane, nonane, decane, dodecane, cyclopentane, cyclohexane, and methylcyclohexane, may be used as the solvent.
  • This hydrogenation reaction is carried out under common hydrogenation reaction conditions, e.g. at a temperature of 20 to 300°C, preferably 40 to 200°C, and under a hydrogen pressure ranging from normal pressure to 200 Kg/cm 2 (G), preferably 20 to 100 Kg/cm 2 (G).
  • the dimerization reaction can be carried out by (i) reacting ⁇ -alkylstyrene in a solid-liquid non-homogeneous system using heteropoly acid in the amount of 1 to 100% by weight of the ⁇ -alkylstyrene in the absence of a solvent at 80 to 140°C (Japanese Patent Application Laid-open No.
  • Octahydroindanes which are cyclic isomers may be produced as by-products when the hydrogenated dimers of ⁇ -alkylstyrene are produced. It is desirable that these by-products are not contained, inasmuch as they tend to reduce the traction coefficient.
  • the purity of the hydrogenated dimers of ⁇ -alkylstyrene should be 70% by weight or higher, and preferably 90% by weight or higher.
  • the component (A) can be obtained by the coupling reaction of aromatic hydrocarbons followed by the hydrogenation of a benzene ring according to the processes described, for example, in Japanese Patent Application Laid-open No. 258131/1985 or No. 262892/1985.
  • a product with an alkyl group introduced into the cyclohexane ring can be obtained if the alkylation is carried out by an aromatic substitution reaction using a Friedel-Krafts catalyst prior to the hydrogenation.
  • the component (B) in the present invention is a heat copolymer of a cyclopentadiene compound and a vinyl aromatic hydrocarbon compound or a hydrogenated product of this heat copolymer.
  • the cyclopentadiene compounds used for preparing the component (B) in the present invention include cyclopentadiene, oligomers of cyclopentadiene, cyclopentadienes into which alkyl groups are substituted, and mixtures of these compounds.
  • cyclopentadiene fractions containing about 30% by weight, preferably about 50% by weight, of cyclopentadienes, produced by steam cracking of naphtha is advantageous.
  • cyclopentadiene fractions may contain olefinic monomers which can copolymerize with alicyclic dienes such as cyclopentadiene.
  • olefinic monomers include aliphatic diolefins such as isoprene, piperilene, or butadiene, and alicyclic olefins such as cyclopentene. Although it is desirable that the content of these olefins be small, up to about 10% by weight for the cyclopentadienes is allowable.
  • a cyclopentadiene compound monomer is counted as one mol, while a dimer is counted as two mols.
  • Styrene, o-, m-, p-vinyltoluene, and ⁇ -, ⁇ -methylstyrene are given as examples of the vinyl aromatic hydrocarbons to be copolymerized with the cyclopentadiene compound for prroducing the component (B).
  • these vinyl aromatic hydrocarbons are preferably used in the amount of less than 3 mols for one mol of the cyclopentadiene compound.
  • the vinyl aromatic hydrocarbons may contain indenes such as indene, methylindene, and ethylindene.
  • C9 fractions produced by steam cracking of naphtha may be uaed for industrial purposes, the use of styrene monomer among various raw materials is particularly preferred from the viewpoint of ensuring good quality of the resulting product.
  • the component (B) of the present invention is a heat copolymer of a cyclopentadiene compound and a vinyl aromatic hydrocarbon compound or a hydrogenated product thereof.
  • the component (B) is a heat copolymer of a cyclopentadiene compound and a vinyl aromatic hydrocarbon compound or a hydrogenated product thereof.
  • a cyclopentadiene compound and a vinyl aromatic hydrocarbon compound are copolymerized in the absence or presence of a solvent, preferably in an atmosphere of inert gas such as nitrogen, at about 160 to 300°C, preferably about 180 to 280°C, for about 0.1 to 10 hours, preferably about 0.5 to 6 hours, under a pressure sufficient to maintain the raw materials in liquid form.
  • a second step polymerization is successively carried out about 160 to 280°C, for about 0.5 to 4 hours under reduced pressure. If necessary, fractions lighter than the target heat copolymer are removed by distillation or the like after the reaction.
  • the heat copolymer of a cyclopentadiene compound and a vinyl aromatic hydrocarbon compound thus produced has a softening point of 40°C or higher or a weight average molecular weight of 250 or greater; preferably a softening point of 100 to 200°C or a weight average molecular weight of 400 to 2,000.
  • this heat copolymer exhibits a high effect as a traction drive fluid without a hydrogenation treatment, it is desirable to hydrogenate the copolymer, taking its performance such as oxidation stability into consideration.
  • the hydrogenation treatment can be carried out by a conventional method.
  • the copolymer is hydrogenated by a treatment using the same hydrogenation catalyst used for the hydrogenation of the component (A), such as nickel, palladium, or platinum in the presence or absence of a solvent at about 70 to 300°C, preferably about 100 to 250°C, under a hydrogen pressure of about 10 to 200 Kg/cm 2 (G), preferably about 20 to 120 Kg/cm 2 (G), for about 0.5 to 20 hours, preferably about 1 to 10 hours.
  • the same hydrogenation catalyst used for the hydrogenation of the component (A) such as nickel, palladium, or platinum in the presence or absence of a solvent at about 70 to 300°C, preferably about 100 to 250°C, under a hydrogen pressure of about 10 to 200 Kg/cm 2 (G), preferably about 20 to 120 Kg/cm 2 (G), for about 0.5 to 20 hours, preferably about 1 to 10 hours.
  • the aromatic ring of the copolymer before the hydrogenation treatment may be alkylated.
  • a methyl, ethyl, n-propyl, i-propyl, or cyclohexyl group is used for the alkylation.
  • the viscosity of the fluid can be decreased by adding a compound having a viscosity lower than the viscosity of the component (A) at 40°C. If such a compound has a high traction coefficient, it is possible to decrease the viscosity while suppressing the reduction in the traction coefficient.
  • Such a compound include the following compounds (i) to (v), of which the incorporation as the component (C) is also within the scope of the present invention.
  • the compounds (i) to (v) may be used either individually or as a mixture of two or more.
  • n5 to n7 representing the number of alkyl group in the compounds (i) to (iii), which are cyclopentadiene oligomers, are preferably integers from 0 to 4.
  • the integer n8 in the decaline compound (iv) is preferably 0 to 8, and more preferably 0 to 4.
  • the poly- ⁇ -olefin compound (v) is a compound having a quaternary or ternary carbon atom in the main chain. Olefins having 3 or more carbon atoms may be used as the raw material. A monomer to tetramer of i-butylene or a monomer to pentamer of propylene are preferably used. These olefins may be used either individually or as a mixture of two or more.
  • the branched poly- ⁇ -olefin compound having a molecular weight in the range of 100 to 1,000 maybe used, with those having a molecular weight in the range of 150 to 500 being particularly preferred. If the molecular weight of the poly- ⁇ -olefin compound is less than 100, the traction drive fluid composition is too subject to evaporation and the oil film cannot be well retained; if more than 1,000, the low temperature fluidity of the composition is decreased.
  • Poly- ⁇ -olefin compounds with no branch such as polyethylene if used as the component (C), result in a traction drive fluid composition having a small traction coefficient, and therefore cannot achieve the effect intended in the present invention.
  • the amount of the component (C)(i) to (C)(v) to be added is 10 to 70 wt%, and preferably 30 to 50 wt%.
  • traction drive fluid composition illustrated above exhibits high traction performance over a wide temperature range
  • a traction drive fluid composition with excellent friction characteristics can be obtained by adding specific amounts of the component (D) and the component (E) which are hereinafter described.
  • the component (D) is a phosphate, an acidic phosphate, a phosphite, or an acidic phosphite. These compounds are represented by one of the following formulas, wherein a plurality of Rs are individually a hydrogen, a hydrocarbon group, or a sulfur-containing hydrocarbon group having 1 to 30 carbon atoms, X is 1, 2 or 3, and Y is 1 or 2.
  • the phosphate are triaryl phosphates and trialkyl phosphates, such as benzyldiphenyl phosphate, allyldiphenyl phosphate, triphenyl phosphate, tricresyl phosphate, ethyldiphenyl phosphate, tributyl phosphate, ethyldibutyl phosphate, cresyldiphenyl phosphate, dicresylphenyl phosphate, ethylphenyldiphenyl phosphate, diethylphenylphenyl phosphate, propylphenyldiphenyl phosphate, dipropylphenylphenyl phosphate, triethylphenyl phosphate, tripropylphenyl phosphate, butylphenyldiphenyl phosphate, dibutylphenylphenyl phosphate, and tributylphenyl phosphate.
  • acidic phosphate examples include 2-ethylhexyl acid phosphate, isodecyl acid phosphate, lauryl acid phosphate, tridecyl acid phosphate, stearyl acid phosphate, iso-stearyl acid phosphate, oleyl acid phosphate, and di(2-ethylhexyl) phosphate.
  • phosphite examples include triphenyl phosphite, tri(p-cresyl) phosphite, tri(nonylphenyl) phosphite, tri-iso-octyl phosphite, diphenyl-iso-decyl phosphite, phenyl-di-iso-decyl phosphite, tri-iso-decyl phosphite, tristearyl phosphite, and trioleyl phosphite.
  • acidic phosphite di(2-ethylhexyl) hydrogenphosphite, dilauryl hydrogenphosphite, and dioleyl hydrogenphosphite.
  • the component (D) is incorporated in the traction drive fluid composition in the amount of 0.01 to 5.0% by weight, preferably 0.03 to 3% by weight, and particularly preferably 0.05 to 1% by weight.
  • the component (E) is an N-type friction modifier or an ester-type friction modifier.
  • Typical N-type friction modifiers are compounds containing -(CO)NH- (amide bond), -NH-, or -N ⁇ in the molecule.
  • the compound containing the amide bond is typified by compounds represented by the formula R 11 - (CO)NH-R 12 , wherein R 11 represents a hydrocarbon group having 3 to 20 carbon atoms and R 12 represents a hydrocarbon group having 2 to 20 carbon atoms.
  • Preferred hydrocarbon groups are alkyl or alkenyl groups. Specific examples include ethyl hexyl amide, butyl hexyl amide, butyl decyl amide, ethyl hexadecyl amide, butyl eicosyl amide, and dihexadecyl amide. Of these, particularly preferred are butyl decyl amide, ethyl hexadecyl amide, and butyl eicosyl amide.
  • the compound containing an -NH- group is typified by compounds represented by the formula R 13 -NH-R 14 , wherein R 13 and R 14 individually represent a hydrocarbon group having 2 to 20 carbon atoms.
  • R 13 and R 14 individually represent a hydrocarbon group having 2 to 20 carbon atoms.
  • Specific examples include ethyl hexyl amine, ethyl decyl amine, butyl decyl amine, ethyl hexadecyl amine, and butyl eicosyl amine. Of these, particularly preferred are ethyl decyl amine, butyl decyl amine, and butyl eicosyl amine.
  • the compound containing an -N ⁇ group is typified by compounds represented by the formula R 15 -N(R 16 -COOH) 2 , wherein R 15 and R 16 individually represent a hydrocarbon group having 2 to 20 carbon atoms.
  • R 15 and R 16 individually represent a hydrocarbon group having 2 to 20 carbon atoms.
  • a specific example is C 18 H 37 -N(C 8 H 16 -COOH) 2 .
  • This is a compound containing both a carboxyl group and the -N ⁇ bond.
  • the ester-type friction modifiers include an ester group, -COOH-, and include such compounds as methyl hexanoate, methyl undecanoate, methyl tetradecanoate, methyl octadecanoate, butyl eicosanoate, octadecyl acetate, and ditetradecyl succinate. Of these, methyl tetradecanoate and methyl octadecanoate are preferred.
  • the component (E) is incorporated in the traction drive fluid composition in the amount of 0.01-3.0% by weight, preferably 0.03-1% by weight, and particularly preferably 0.05-0.5% by weight. If this amount is too small, only slight improvement can be achieved in the anti-shudder characteristic ( ⁇ -V characteristic); if too large, the static friction coefficient is decreased and sliding of the wet clutch is produced due to the decrease in the transmission torque capacity.
  • additives may be incorporated in the traction drive fluid composition of the present invention.
  • additives include anti-wear agents, ashless-type dispersants, metallic-type detergents, antioxidants, rust inhibitors, metal deactivators, viscosity index improvers, pour point depressants, metal deactivators, and anti-foaming agents.
  • these additives are: as the metallic-type detergents, alkaline earth metal sulfonates and alkaline earth metal phenates; as the ashless-type dispersants, alkenyl succinic acid imide, alkenyl succinic ester, and amides of long-chain fatty acid and polyamine (amino-amide type); as the wear preventives, zinc dialkyldithiophosphate; as the anioxidants, amine-type anioxidants and phenol-type anioxidants; as the rust inhibitors, alkenyl succinic ester and alkenyl succinic half ester; as the metal deactivators, benztriazole and thiadizole; as the viscosity index improvers, polymethacrylates and olefin copolymers; as the pour point depressants, polymethacrylates; and as the anti-foaming agents, silicon compounds and ester-type anti-foaming agents.
  • composition of the components (A) and (B), or the composition further added with the component (C) which has a viscosity smaller than the component (A) provides a traction drive fluid composition having a high traction coefficient in a wide temperature range and exhibiting excellent low temperature fluidity.
  • the traction drive fluid composition of the present invention thus having a high traction coefficient over a wide temperature range and exhibiting excellent friction characteristics is particularly useful for use in vehicles.
  • 1,200 g of ⁇ -methylstyrene, 400 g of water, and 800 g of H 3 PW 12 O 40 were placed in a 5 l reaction vessel made of glass equipped with a cooling tube and a thermometer, and reacted at 100°C for 3 hours. After the reaction, the reaction mixture was cooled to remove a water layer. The organic layer was dehydrated with anhydrous Na 2 SO 4 . After removal of the Na 2 SO 4 by filtration, the organic layer was analyzed by gas chromatography to confirm that the conversion rate of ⁇ -methylstyrene was 89.5wt%, the yield of ⁇ -methylstyrene dimer was 86.4 wt%, and the selectivity was 96.5 wt%.
  • a cyclopentadiene fraction obtained from steam cracking of naphtha (consisting of 75.0 wt% of dicyclopentadiene, 5.4 wt% of olefins, and balance of which the major component is saturated hydrocarbons), 125 g of styrene monomer, and 775 g of xylene were reacted at 260°C in a nitrogen atmosphere at a pressure of 18 Kg/cm 2 (G) for 3 hours.
  • N111TM a hydrogenation catalyst, manufactured by Nikki Kagaku Co., Ltd.
  • This copolymer is one of the examples of the component (B) and hereinafter referred to as a component (b).
  • the copolymer had a softening point of 175°C and a weight average molecular weight of 1,300.
  • N111TM a hydrogenation catalyst, manufactured by Nikki Kagaku Co., Ltd.
  • This product is structurally one of the examples of the compound (iii) of the component (C) and hereinafter referred to as a component (c-1).
  • a hydrogenated cyclopentadiene condensate prepared in the same manner as in Synthetic Example 4 was distilled to obtain 48 wt% of an overhead fraction.
  • a GPC analysis of this overhead fraction confirmed that the product contained trimer, tetramer, and pentamer of cyclopentadiene in the amount respectively of 85 wt%, 13 wt%, and 2 wt%.
  • This product is structurally one of the examples of the compound (ii) of the component (C) and hereinafter referred to as a component (c-2).
  • Traction drive fluid compositions with the formulation shown in Table 1 were prepared using the products prepared in Synthetic Examples 1-6.
  • Traction drive fluid compositions were prepared according to the formulation shown in Tables 2-1 and 2-2, wherein, (A) is 2,4-dicyclohexyl-2-methylpenetane, (B) is hydrogenated copolymer of cyclopentadiene and vinyl aromatic hydrocarbons, (C1) is hydrogenated cyclopentadiene condensate (dimers and trimers), and (C2) is polyisobutylene with a weight average molecular weight of 300.
  • the transmission torque capacity was measured by SAE No. 2 test using two paper disks for automatic transmission, four steel plates for automatic transmission, at a rotation of motor of 3,000 rpm (dynamic cycle) or 0.7 rpm (static cycle), a pressure of 2.81 kg/cm 2 , and an oil bath temperature of 120°C.
  • the static friction coefficient at static cycle was measured after 500 cycle operation at dynamic cycle. The transmission torque capacity was deemed to be sufficient if the static friction coefficient was 0.120 or greater.
  • Friction coefficient at a rotation of 1 rpm ( ⁇ 1) and a rotation of 50 rpm ( ⁇ 50) were measured at a fluid temperature of 40°C and a pressure of 10 kg/cm 2 using a paper disk for automatic change gear and a steel plate for automatic change gear.
  • the anti-shudder performance indicated by the ratio ⁇ 1/ ⁇ 50 was calculated.
  • the value ⁇ 1/ ⁇ 50 less than 1 indicates that no shudder occurrs.
  • the viscosity at -30°C was measured according to the Brookfield viscosity test method of ASTM D 2983.
  • a transmitted tangential stress was measured using a four-cylinder friction tester at a driving axial rotation of 2,000 rpm (4.19 m/s), a specific sliding of 5%, a transmitted tangential stress of 395 kg, and test fluid temperatures of 30°C and 120°C.
  • the traction coefficient is expressed by the ratio of the transmitted tangential stress against the transmitted tangential stress.
  • the compositions of Examples 7-14 possessed a high traction coefficient in a wide temperature range and exhibited excellent transmission torque capacity and anti-shudder performance, although the low-temperature fluidity of these compositions was rather small.
  • the addition of the component (C) as a low-viscosity component or a viscosity decreasing agent improved the temperature characteristics and resulted in traction drive fluid compositions with excellent low-temperature fluidity.
  • the compositions of Examples 15-19 has a traction coefficient slightly smaller than that of the compositions in Examples 7-14, their temperature characteristics and low-temperature fluidity are more excellent.
  • the former compositions are therefore suitable as a traction drive fluid for vehicles used under the condistions of a wide temperature range.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
EP96109344A 1995-06-13 1996-06-11 Composition de fluide de traction Withdrawn EP0748863A3 (fr)

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JP170233/95 1995-06-13
JP17023395 1995-06-13
JP34989295A JP3425024B2 (ja) 1995-06-13 1995-12-21 トラクションドライブ用流体
JP349892/95 1995-12-21

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0949319A2 (fr) * 1998-04-08 1999-10-13 Nippon Mitsubishi Oil Corporation Fluide de traction
EP1118654A1 (fr) * 1999-04-16 2001-07-25 Nippon Mitsubishi Oil Corporation Fluides pour entrainement par traction
EP1391499A1 (fr) * 2001-05-29 2004-02-25 Idemitsu Kosan Co., Ltd. Preparation d'huile de base lubrifiante
WO2007084207A1 (fr) * 2006-01-17 2007-07-26 Exxonmobil Chemical Patents Inc. Système d'additifs pour fluides de lubrification
WO2020150123A1 (fr) * 2019-01-17 2020-07-23 The Lubrizol Corporation Fluides de traction
WO2020186139A1 (fr) * 2019-03-13 2020-09-17 Valvoline Licensing And Intellectual Property Llc Nouveau fluide de traction presentant des propriétés améliorées à basse température

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* Cited by examiner, † Cited by third party
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JP3811996B2 (ja) * 1996-07-10 2006-08-23 株式会社コスモ総合研究所 トラクションドライブ用流体
KR101148645B1 (ko) 2003-10-08 2012-05-30 이데미쓰 고산 가부시키가이샤 윤활유 기유 및 윤활유 조성물

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EP0526218A1 (fr) * 1991-07-31 1993-02-03 Tonen Corporation Fluides de traction dérivés d'oligomères du cyclopentadiene
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JPS60228599A (ja) * 1984-04-27 1985-11-13 Idemitsu Kosan Co Ltd トラクシヨンドライブ用流体
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EP0526218A1 (fr) * 1991-07-31 1993-02-03 Tonen Corporation Fluides de traction dérivés d'oligomères du cyclopentadiene
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0949319A3 (fr) * 1998-04-08 2001-03-21 Nippon Mitsubishi Oil Corporation Fluide de traction
EP0949319A2 (fr) * 1998-04-08 1999-10-13 Nippon Mitsubishi Oil Corporation Fluide de traction
EP1118654A4 (fr) * 1999-04-16 2007-03-07 Nippon Mitsubishi Oil Corp Fluides pour entrainement par traction
EP1118654A1 (fr) * 1999-04-16 2001-07-25 Nippon Mitsubishi Oil Corporation Fluides pour entrainement par traction
EP1391499A4 (fr) * 2001-05-29 2009-06-03 Idemitsu Kosan Co Preparation d'huile de base lubrifiante
EP1391499A1 (fr) * 2001-05-29 2004-02-25 Idemitsu Kosan Co., Ltd. Preparation d'huile de base lubrifiante
WO2007084207A1 (fr) * 2006-01-17 2007-07-26 Exxonmobil Chemical Patents Inc. Système d'additifs pour fluides de lubrification
WO2020150123A1 (fr) * 2019-01-17 2020-07-23 The Lubrizol Corporation Fluides de traction
US11384306B2 (en) 2019-01-17 2022-07-12 The Lubrizol Corporation Traction fluids
WO2020186139A1 (fr) * 2019-03-13 2020-09-17 Valvoline Licensing And Intellectual Property Llc Nouveau fluide de traction presentant des propriétés améliorées à basse température
US10894930B2 (en) * 2019-03-13 2021-01-19 Valvoline Licensing And Intellectual Property Llc Traction fluid with improved low temperature properties
US10927321B2 (en) 2019-03-13 2021-02-23 Valvoline Licensing And Intellectual Property Llc Traction fluid with improved low temperature properties
CN113692438A (zh) * 2019-03-13 2021-11-23 胜牌许可和知识产权有限公司 具有改进的低温性能的新型牵引流体
CN113692438B (zh) * 2019-03-13 2022-10-18 胜牌许可和知识产权有限公司 具有改进的低温性能的牵引流体

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