JPH0959660A - Fluid for traction drive - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a fluid for traction drive which has a high traction coefficient at about 30 deg.C and exhibits a small decrease in traction coefficient even at a high temp. by compounding two specific components. SOLUTION: This fluid is prepd. by compounding 85-97wt.% at least one compd. resented by formula I and/or formula II (wherein R1 to R10 are each independently H, a 1-3C alkyl, or cyclohexyl; Q1 to Q4 are each independenly an alkyl or cyclohexyl; n1 to n4 are each independently an integer of 0-5; and when n1 to n4 are each 2-5, then each of all the Q1 's to Q4 ' s is selected independently) with 15-3wt.% optionally hydrogenated thermal copolymer of a cyclopentadiene compd. with a vinylarom. hydrocarbon compd., the copolymer having a softening point of 40 deg.C or higher and a wt. average mol.wt. of 250 or higher.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a traction drive fluid. More specifically, those obtained by thermal copolymerization of cyclopentadiene and vinyl aromatic hydrocarbons, or a hydride thereof (B) component having a softening point of 40 ° C. or higher or a weight average molecular weight of 250 or higher, And (A-1) and / or (A-
The component (A), which is a compound having the structure of 2), is blended at a weight ratio (A) / (B) of 85/15 to 97/3, or the blending weight ratio (A) / (B). ) Is 85 /
When it is 15 or less, the component (C), which has a lower viscosity than that of the component (A) used therein, is further blended, and relates to a traction drive fluid exhibiting a high traction coefficient in a wide temperature range.

[0002]

2. Description of the Related Art A traction drive device is a power transmission device utilizing rolling-sliding friction resulting from a resistance force against shearing caused by a fluid oil film sandwiched between a cylindrical or conical rotating body losing fluidity and hardening. Therefore, it has been widely used in automobile continuously variable transmissions, industrial continuously variable transmissions, hydraulic equipment, and the like. Particularly in recent years, researches for higher performance or reduction in size and weight have been advanced mainly for automobile applications, and high performance fluids for traction drive have been required.

Conventionally, various traction drive fluids have been proposed in JP-A-60-228599, JP-A-60-96690, JP-A-60-58495, etc., but these have a traction coefficient at around 30.degree. Relatively expensive,
The traction coefficient decreases as the temperature rises, and the traction coefficient is low in a high temperature range, which is considered to be the oil temperature during actual running, and is not practical. Further, as a method for improving the traction coefficient at high temperature, there is JP-A-5-1292. This is because the traction coefficient in a high temperature region (around 120 ° C.) is improved by adding a thermal copolymer of cyclopentadiene and α-olefin to a cyclopentadiene-based trimer or hexamer as a main component. It is a technique to do.

Japanese Patent Application Laid-Open No. 1-230696 describes the effect of improving the traction coefficient of a cyclopentadiene-based polymer in a high temperature region. This is because a cyclopentadiene-based homopolymer has a high effect and other copolymers. Is described as being an aliphatic olefin or diene.

[0005]

The problem to be solved by the present invention is to obtain a traction drive fluid having a high traction coefficient at around 30 ° C. and having a small decrease in the traction coefficient even in a high temperature range. .

[0006]

Means for Solving the Problems The inventors of the present invention have conducted extensive studies on the development of a traction drive fluid having a high traction coefficient in a high temperature oil region, and as a result, 3
It has a high traction coefficient near 0 ° C and will be described later (A
-1) and / or compound (A-2) (component (A)) is a thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon or a hydride thereof and has a softening point of about 40 ° C or higher or weight. (A) / (B) having an average molecular weight of 250 or more (component (B)) is 85/15 to 97 /
Was added in the weight ratio of 3 or its blending weight ratio (A)
In the case where / (B) is less than 85/15, the temperature for the traction drive fluid, which has a viscosity lower than that of the component (A) used therein and which is described later, is excellent due to a synergistic effect. With the knowledge that it has characteristics,
The present invention has been completed.

That is, the gist of the present invention is that the general formula

Embedded image (In the formula, R _{1 to} R ₁₀ may be independently selected from hydrogen or a C _{1 to} C ₃ alkyl group or a cyclohexyl group, and Q _{1 to} Q ₄ may be selected from a C _{1 to} C ₃ alkyl group or a cyclohexyl group. Each of them may be independently selected, and when n _{1 to} n ₄ are 2 to 5, individual groups of a plurality of Q _{1 to} Q ₄ may be independently selected, and n _{1 to} n ₄ are 0 to 5 At least one compound represented by the formula (1) is used as the component (A), and is a thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon or a hydride thereof having a softening point of 40 ° C. or higher or A component having a weight average molecular weight of 250 or more is contained as the component (B), and the weight ratio of the component (A) to the component (B) (A)
/ (B) is 85/15 to 97/3, which is a traction drive fluid. A further subject matter of the present invention resides in a traction drive fluid which is improved while maintaining the characteristics thereof or in which some of the characteristics are changed.

As the component (A) ((A-1) and / or (A-2)), those represented by the following general formula can be used.

[0009]

Embedded image (In the formula, R _{1 to} R ₁₀ may be independently selected from hydrogen or a C _{1 to} C ₃ alkyl group or a cyclohexyl group, and Q _{1 to} Q ₄ may be selected from a C _{1 to} C ₃ alkyl group or a cyclohexyl group. Each of them can be independently selected, and when n _{1 to} n ₄ are 2 to 11, individual groups of a plurality of Q _{1 to} Q ₄ can also be independently selected, and n _{1 to} n ₄ are 0 to 11 Represents the integer of.)

In the present specification, the C ₁ -C ₃ alkyl group specifically refers to a methyl group, an ethyl group, an n-propyl group and an i-propyl group, and is bonded to a cyclic carbon skeleton. Hydrogen is not shown as a substituent.

From various viewpoints, in the present invention, among the compounds represented by the above formula, those in which n _{1 to} n ₄ are integers of 0 to 5 are used.

Of the compounds represented by the above formula, R _{1 to} R
₁₀ is preferably hydrogen or a methyl group or an ethyl group. Among these, hydrogen or a methyl group is preferable. Further, those in which the carbon atom adjacent to the cyclohexyl group is alkylated are particularly preferable. And considering the availability and cost of raw materials, n _{1 to} n ₄ are practically 0
It is particularly suitable to be in the range from 2 to 2. When Q _{1 to} Q ₄ are present, a methyl group is common. Preferred examples of (A-1) and (A-2) include 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, 2,4
-Dicyclohexyl-2,3-dimethylpentane and the like. Further, a compound in which any methyl group of the above compound is substituted with an ethyl group, an n-propyl group, an i-propyl group or a cyclohexyl group, and a cyclohexyl ring is a methyl group, an ethyl group, an n-propyl group or an i-propyl group. And those optionally alkylated with one or more groups selected from cyclohexyl groups. Also,
Each of (A-1) and (A-2) may be a single compound or a mixture prepared by mixing them at an arbitrary ratio.

For example, the α-alkylstyrene dimer hydride which is one type of the component (A) can be obtained by dimerizing α-alkylstyrene and further hydrogenating it. However, the dimerization and hydrogenation methods are not particularly limited and can be appropriately performed by any method.

For example, the dimerization of α-methylstyrene can be carried out in the presence of a catalyst, generally an acidic catalyst, if necessary, with addition of a solvent, a reaction modifier and the like. Specific examples of the acid catalyst include activated clay, clay such as acid clay, sulfuric acid,
Mineral acids such as hydrochloric acid and hydrofluoric acid, organic acids such as p-toluenesulfonic acid and triflic acid, aluminum chloride, ferric chloride, stannic chloride, boron trifluoride, boron tribromide, aluminum bromide Lewis acids such as gallium chloride and gallium bromide, and solid acids such as zeolite, silica, alumina, silica-alumina, cation exchange resins,
Heteropoly acids and the like can be mentioned. The addition amount of this acidic catalyst is generally 0.1 to 100 wt with respect to α-methylstyrene.
%, Preferably 1 to 20 wt%, but there is no particular limitation. Saturated hydrocarbons may be used as the solvent, and specific examples thereof include n-pentane, n-hexane, heptane, octane, nonane, decane and the like, cyclopentane, cyclohexane, methylcyclohexane, decalin and the like. The reaction modifier is used for the purpose of increasing the selectivity of the dimer produced in this reaction, and specifically, carboxylic acids such as acetic acid, acid anhydrides such as acetic anhydride and phthalic anhydride, γ-butyrolactone and valerolactone. Cyclic esters such as ethylene glycol, glycols such as ethylene glycol, mononitro compounds such as nitromethane and nitrobenzene, esters such as ethyl acetate, ketones such as mesityl oxide, aldehydes such as formalin and acetaldehyde, cellosolves, diethylene glycol mono Examples thereof include polyalkylene glycol alkyl ethers such as ethyl ether.

The dimerization reaction is generally -30 to 180.
C., preferably 0 to 160.degree. C.

The hydrogenation of the α-methylstyrene dimer obtained as described above can also be generally carried out in the presence of a catalyst, if necessary, by adding a solvent and the like. As the catalyst, nickel, ruthenium, palladium, platinum, rhodium, iridium, copper, chromium, molybdenum, cobalt,
What is known as a so-called hydrogenation catalyst containing one or more metals such as tungsten can be used.
The amount of the catalyst added is not particularly limited, but is usually 0.1 to 100% by weight, preferably 1 to 20% with respect to the above polymer.
wt%.

Examples of the solvent include n-pentane, n-hexane, heptane, octane, nonane, decane, dodecane and the like, and liquid saturated hydrocarbons such as cyclopentane, cyclohexane and methylcyclohexane. This hydrogenation reaction is carried out in the same manner as the usual hydrogenation reaction, and is 20 to 300.
℃, preferably in the temperature range of 40 ~ 200 ℃, normal pressure ~ 2
00Kg / cm ² (G), preferably 20-100Kg / cm
It can be carried out under a hydrogen pressure of ² (G).

The process for producing the dimer of α-methylstyrene has been described above. The dimer of α-alkylstyrene substituted with an alkyl group or cycloalkyl group other than styrene or a methyl group. It will be apparent to those skilled in the art that hydrides of can be similarly prepared.

2 of α-alkylstyrene used in the present invention
Since it is necessary to particularly increase the proportion of linear bodies in the polymer hydride, it is particularly preferable that the polymer hydride is produced by the following method, which the present inventors have already applied for a patent. That is, using α-alkyl styrenes, i) 1 to 100 wt% of heteropoly acid based on the starting α-alkyl styrene, without solvent,
Is it a solid-liquid phase heterogeneous system and is dimerized at 80 to 140 ° C. (Japanese Patent Application No. 6-60251 and Japanese Patent Application Laid-Open No. 7-24257).
5), or ii) 1 based on the raw material α-alkylstyrenes
˜200 wt% heteropoly acid in the presence of a solvent that does not dissolve the catalyst, in a solid-liquid phase heterogeneous system, 30 to 14
Dimerization at 0 ° C. (Japanese Patent Application No. 6-60251, Japanese Patent Laid-Open No. H7-70251)
242575), or iii) a method of dimerizing a heteropolyacid in the presence of water (Japanese Patent Application No. 6-6025).
2, JP-A-7-242573) is preferable. The reaction solution obtained by subjecting this reaction product to the above-mentioned known hydrogenation reaction has an extremely high proportion of linear bodies, and thus has an advantage that a difficult separation step of a cyclic body can be omitted. further,
The above-mentioned dimerization method proposed by the present inventors has a high conversion rate to a dimer and can significantly shorten the reaction time, and is therefore economically advantageous.

When a hydrogenated α-alkylstyrene dimer is obtained, a cyclic isomer octahydroindane may be produced as a by-product. This is preferably not included because it reduces the traction coefficient. The purity of the α-alkylstyrene dimer hydride is 70 wt% or more, preferably 90 wt% or more.

In addition to dimerization of the component (A), for example, JP-A-60-258131 and JP-A-60-262892.
As described above, it can also be obtained by nuclear hydrogenation after the coupling reaction of an aromatic compound. Prior to nuclear hydrogenation, alkylation is carried out by an aromatic substitution reaction such as Friedel-Crafts reaction, and then hydrogenation is carried out to obtain a compound having an alkyl group introduced into a cyclohexane ring.

The component (B) of the present invention is as described above.
It is a thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon or its hydride.

The cyclopentadiene used in the production of the component (B) of the present invention includes cyclopentadiene, a multimer thereof, an alkyl-substituted product thereof or a mixture thereof, and industrially steam such as naphtha. It is advantageous to use a cyclopentadiene-based fraction (CPD fraction) containing about 30 wt% or more, preferably about 50 wt% or more of cyclopentadiene obtained by cracking.

Further, the CPD fraction may contain an olefinic monomer copolymerizable with these alicyclic dienes. Examples of the olefinic monomer include aliphatic diolefins such as isoprene, piperylene and butadiene, and alicyclic olefins such as cyclopentene. The concentration of these olefins is preferably low, but about 10 wt% or less per cyclopentadiene is acceptable.

When a monomer such as cyclopentadiene is used as the cyclopentadiene, 1 mol is 2
When a monomer is used, it is calculated as 2 mol.

Examples of vinyl aromatic hydrocarbons as a raw material for copolymerization include styrene, o-, m-, p-vinyltoluene, α-, β-methylstyrene and the like, and 3 mol per 1 mol of cyclopentadiene. It is industrially preferable to blend less than this. The vinyl aromatic hydrocarbons can include indenes such as indene, methylindene and ethylindene. Industrially, it is preferable to use a so-called C ₉ fraction obtained by steam cracking such as naphtha, but from the viewpoint of the quality of the obtained product, it is particularly preferable to use a styrene monomer among these various raw materials.

The component (B) of the present invention may be a thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon or a hydride thereof, and the production method thereof is not particularly limited, but cyclopentadiene and vinyl aromatic are preferred. The following method is mentioned as one preferable example of the thermal copolymerization method of hydrocarbons.

Cyclopentadiene and vinyl aromatic hydrocarbon in the presence or absence of a solvent, preferably in an inert gas atmosphere such as nitrogen gas, at about 160 to 300.
C., preferably about 0.8 at a temperature range of about 180-280.degree.
Thermal copolymerization is carried out for 1 to 10 hours, preferably about 0.5 to 6 hours, under a pressure capable of holding the raw material system in the liquid phase.

After removing the inactive components in the raw materials, the unreacted raw materials and, if necessary, the solvent from the polymerization liquid under atmospheric pressure or reduced pressure by an operation such as distillation, the second stage polymerization is continued under reduced pressure at about 160. It is carried out at ˜280 ° C. for about 0.5 to 4 hours, and if necessary, a lighter one than the desired thermal copolymer is removed by an operation such as distillation.

The thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon thus obtained has a softening point of 40 ° C. or more or a weight average molecular weight of about 250 or more,
Preferably, the softening point is 100 ° C. or higher and 200 ° C. or lower, or the weight average molecular weight is 400 or higher and 2000 or lower.

Further, the above thermal copolymer exhibits a high compounding effect as a traction drive fluid without hydrotreating, but it is preferable to further perform hydrotreating in consideration of performances such as oxidation stability. .

The hydrotreatment can be carried out by a usual method. For example, a catalyst used for hydrogenating the above-mentioned component (A), particularly a hydrogenation catalyst such as nickel, palladium or platinum, is used, and the amount thereof is about 70 to 70% in the presence or absence of a solvent.
A temperature range of 300 ° C, preferably about 100-250 ° C,
Hydrogen pressure about 10 to 200 kg / cm ² (G), preferably about 20
Under pressure of ~ 120Kg / cm ² (G) for about 0.5 ~ 20 hours,
Preferably, the hydrotreatment may be performed for about 1 to 10 hours.

It is also possible to carry out alkylation on the aromatic ring of the thermal copolymer before hydrotreating. In this case, the alkyl group may be methyl group, ethyl group, n-propyl group, i-
Examples thereof include a propyl group and a cyclohexyl group.

In the first embodiment of the present invention, the thermal copolymer of the components (A) and (B), a cyclopentadiene and a vinyl aromatic hydrocarbon, or a hydride thereof is mixed in a weight ratio (A). ) / (B) is 85/15 to 97/3, preferably 85/15 to 95/5. If the proportion of the component (B) is too small, the effect of improving the traction coefficient at high temperatures is hardly recognized, and if it is too large, the viscosity increases and the traction coefficient increases, but problems such as energy loss during handling or use occur. It is not preferable. However, even when the compounding ratio is within the above range, when it is desired to further reduce the viscosity, or when the component (B) is used in a larger amount than the component (A) as the second aspect of the present invention, Has a higher viscosity, so that the viscosity can be lowered by adding a compound whose viscosity at 40 ° C. is lower than that of the component (A) used therein.
Among them, if a material having a high traction coefficient is used, it is possible to reduce the viscosity while reducing the decrease in the traction coefficient. The following can be mentioned as preferred specific examples, and an embodiment using these as the component (C) is also within the scope of the present invention. The compounds (i) to (iv) may be used alone or in combination.

(I) A hydride of a compound in which dicyclopentadiene or any hydrogen thereof is substituted with a C ₁ -C ₃ alkyl group or a cyclohexyl group. The structural formula is as follows.

[0036]

Embedded image (Wherein, when Q ₅ is obtained independently selected from alkyl or cyclohexyl group C ₁ ~C _3, n ₅ represents an integer of 0. And n ₅ is 2 to 10, Each Q ₅ can be independently selected.)

(Ii) A hydride of a compound in which tricyclopentadiene or any hydrogen thereof is substituted with a C ₁ -C ₃ alkyl group or a cyclohexyl group. The structural formula is as follows.

[0038]

Embedded image (Q ₆ may be independently selected from a C ₁ -C ₃ alkyl group or a cyclohexyl group, n ₆ represents an integer of 0 to 15. When n ₆ is 2 to 15, each Q 6 ₆ can be independently selected.)

(Iii) A hydride of a compound in which tetracyclopentadiene or any hydrogen thereof is substituted with a C ₁ -C ₃ alkyl group or a cyclohexyl group. The structural formula is as follows.

[0040]

[Chemical 6] (Q ₇ can be independently selected from a C ₁ -C ₃ alkyl group or a cyclohexyl group, n ₇ represents an integer of 0-20, and when n ₇ is 2-20, each Q ₇ is Can be independently selected.)

(Iv) Decalin or any hydrogen thereof is C
Compounds substituted with the ₁ -C ₃ alkyl group or a cyclohexyl group. The structural formula is as follows.

[0042]

[Chemical 7] (Wherein, when Q ₈ is obtained independently selected from alkyl or cyclohexyl group C ₁ ~C _3, n ₈ is represented. The n ₈ is 2 to 10 an integer of 0, the Each Q ₈ can be independently selected.)

[0043] (C) The number of alkyl groups of components, given the easy availability and cost of raw materials, n ₅ ~n ₇ of cyclopentadiene polymer (i) ~ (iii) is in practice 0
It is preferably in the range of 4 to 4.

Further, n _{8 of} (iv) which is a decalin compound
Is preferably 0 to 8 and particularly preferably 0 to 4.

The amount of component (C) added is 10 to 60 wt.
%, Preferably 30 to 50 wt%.

In the general formulas in the present specification, []
The symbol with Q attached indicates that the substitution position of the substituent Q is arbitrary.

The fluid for traction drive which is the object of the present invention can be prepared by adding various additives such as antioxidants and antiwear agents in an amount of 0.05 to 10 wt% depending on the application.

The thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon, which are the components (A) and (B), or the hydride thereof in the present invention has a traction coefficient particularly in a high temperature region due to a synergistic effect. Greatly improve.
This means that the traction coefficients in Examples 1 to 6 to be described later are Comparative Examples 1 and 2 using only the component (A),
It is understood that it is higher than both Comparative Example 3 using the component (C) alone and Comparative example 4 using the mixture of the component (B) and the component (C).

The synergistic effect of a large improvement in the traction coefficient by the combination of the components (A) and (B) in the present invention is not seen in the above-mentioned JP-A-5-1292.
Further, the synergistic effect that we have found in the present invention is exerted between the component (A), a thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon, or a hydride thereof, The operation is different from that of the above-mentioned JP-A-1-230696.

[0050]

EXAMPLES The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.

The traction drive fluids obtained in Examples and Comparative Examples were evaluated by the following methods. Traction coefficient: Using a four-cylinder type friction tester, drive shaft rotation speed 2,000 rpm (4.19 m / s), slip ratio 5%,
It was expressed as the ratio of the transmitted tangential force to the normal load measured at a normal load of 395 Kg and a test oil temperature of 30 ° C to 120 ° C.

Production Example 1 1200 g of α-methylstyrene, 400 g of H ₂ O, H ₃
800 g of PW ₁₂ O ₄₀ was placed in a 5 liter glass reactor, a cooling device and a thermometer were attached, and reaction was carried out at 100 ° C. for 3 hours. After cooling, the aqueous layer was removed, and the organic layer was dehydrated with anhydrous Na ₂ SO ₄ . Na ₂ SO ₄ was removed by filtration. When the organic layer was analyzed by gas chromatography, α-
The conversion of methylstyrene is 89.5 wt%, the yield of α-methylstyrene dimer is 86.4 wt%, and the selectivity is 9
It was 6.5 wt%.

1200 g of the organic layer thus obtained was
Place in a 0 l autoclave and add 50 cyclohexane.
00 g and N-113 (JGC Chemical Co., Ltd., hydrogenation catalyst) 120 g were added and the autoclave was sealed. The reaction was carried out at a hydrogen pressure of 60 kg / cm ² (G) and a reaction temperature of 180 ° C. for 5 hours, followed by cooling and removal of the catalyst by filtration. The hydrogenated product of cyclohexane and α-methylstyrene was distilled off to obtain 1250 g of a product. When analyzed by gas chromatography, 2,4-dicyclohexyl-2-methylpentane (hereinafter referred to as component (a-1). This is structurally one specific example of component (A-2). The purity was 96.5 wt%.

Production Example 2 A thermometer and a cooling tube were attached to a 5 liter glass reactor, 2300 g of anhydrous cumene, 40 g of metallic sodium and 11 g of isopropyl alcohol were placed therein, heated to 130 ° C., and 650 g of styrene was stirred for 3 hours. The mixture was added dropwise and continuously stirred for 1 hour for reaction. After stirring was stopped and cooled, the oil layer was taken out, 200 g of ethanol was added, and 5
It was washed three times with an aqueous solution of N hydrochloric acid and 2 l of a saturated saline solution. After drying over anhydrous Na ₂ SO ₄ , unreacted cumene was distilled off by a rotary evaporator, and then distilled under reduced pressure to give a boiling point of 115 to 125 ° C. (0.13 mmHg) fraction 700 g.
I got 450 g of this fraction was placed in a 10 l autoclave, 4500 g of cyclohexane and 45 g of N-113 (JGC Chemical Co., Ltd.) hydrogenation catalyst were placed therein, and the autoclave was closed. 180 ℃ under hydrogen pressure 60Kg / cm ² (G),
It was hydrogenated for 5 hours and cooled to room temperature. The catalyst is filtered off,
When cyclohexane was distilled off by a rotary evaporator and then analyzed, 1,3-dicyclohexyl-3-methylbutane (hereinafter referred to as component (a-2). This is a structural example of component (A-2). There was).

Production Example 3 500 g of a cyclopentadiene fraction consisting of 75.0 wt% of dicyclopentadiene obtained by steam cracking of naphtha, 5.4 wt% of an olefin and the balance of the saturated hydrocarbon, 125 g of styrene monomer and 775 g of xylene. And in a nitrogen atmosphere at 18 kg / cm ² (G), 260 ° C
And reacted for 3 hours. Inert fraction in the raw material from the reaction solution,
The unreacted raw materials and the solvent were first distilled off under pressure and then under reduced pressure at 252 ° C., and then 50 Torr. Was maintained at the same temperature for 1 hour under reduced pressure, and the second-stage polymerization was carried out while distilling off the cyclopentadiene-based condensate. From the bottom, 401 g of cyclopentadiene-vinyl aromatic hydrocarbon thermal copolymer was obtained. N-111 (JGC Chemical Co., Ltd., hydrogenation catalyst) 3 wt% was added and hydrogenated at a hydrogen pressure of 60 kg / cm ² (G) at a reaction temperature of 220 ° C. for 6 hours to obtain the desired hydrogenated cyclopentadiene-vinyl aromatic. 401 g of a hydrocarbon thermal copolymer (hereinafter referred to as the component (b). This is structurally one specific example of the component (B)) was obtained. Softening point 175 ° C,
The weight average molecular weight was 1,300.

Production Example 4 600 g of the cyclopentadiene fraction used in Production Example 3 and 400 g of xylene as a solvent were mixed under a nitrogen atmosphere at 18 kg / cm.
² (G) was reacted at 260 ° C. for 3 hours. Inert fraction in the raw material, unreacted raw material and solvent from the reaction solution under pressure first,
After distilling off at 160 ° C. under reduced pressure, 50 Torr. The mixture was kept under the reduced pressure of 1 hour at the same temperature to obtain 56 g of a desired cyclopentadiene condensate. N-111 (a hydrogenation catalyst, JGC Chemical Co., Ltd.) was added to 56 g of the obtained fraction.
wt% was added, hydrogen pressure 60 kg / cm ² (G), reaction temperature 18
A hydrogenated cyclopentadiene-based condensate (hereinafter referred to as “component (c-1)” is reacted at 0 ° C. for 4 hours. Structurally, it is one specific example of component (iii) as the component (C) as an average composition. .) Was obtained. GPC analysis showed that cyclopentadiene 3,4,5,6 mer was 41
%, 25% by weight, 19% by weight, and 7% by weight.

Production Example 5 The hydrogenated cyclopentadiene condensate obtained in the same manner as in Production Example 4 was distilled to obtain 48 wt% as an overhead component. GPC analysis showed that cyclopentadiene 3,4,5 pentamers were 85 wt%, 13 wt% and 2 wt, respectively.
% (Hereinafter, referred to as the component (c-2). This is one specific example of the component (C) as a structurally average composition).

Production Example 6 2-Ethylnaphthalene (Aldrich) 1 kg, N-11
100 g of a trinuclear hydrogenation catalyst (manufactured by JGC Chemical Co., Ltd.) and 10 kg of cyclohexane were placed in a 20 l autoclave and sealed.
The mixture was stirred and reacted at 200 ° C. for 5 hours under a hydrogen pressure of 6.0 MPa. After cooling, the autoclave was opened, the catalyst was removed by filtration, and cyclohexane was evaporated to give 2-
1.06 kg of ethyldecalin was obtained (hereinafter (c-3)
Described as an ingredient. Structurally, this is one specific example of component (iv) of component (C). ).

Examples 1 to 6 and Comparative Examples 1 to 4 Using the products obtained in the above Production Examples 1 to 6, traction drive fluids having the composition shown in Table 1 were produced.

[0060]

[Table 1]

A-1: 2,4-dicyclohexyl-2-
Methyl pentane a-2: 1,3-dicyclohexyl-3-methylbutane b: Hydrogenated cyclopentadiene-vinyl aromatic hydrocarbon thermal copolymer c-1: Cyclopentadiene polymer, 3,4
Content of 5 and 6 mer is 41wt%, 25wt%, 1 respectively
9 wt% and 7 wt% c-2: cyclopentadiene polymer having 3,4
The pentamers are 85 wt%, 13 wt% and 2 wt% respectively c-3: 2-ethyldecalin

The traction coefficients of the fluids of Examples 1 to 6 and Comparative Examples 1 to 4 were measured at temperatures of 30 ° C to 120 ° C, respectively. The obtained results are shown in FIGS. 1, 2, and 3 with the horizontal axis as the measured temperature and the vertical axis as the traction coefficient μ. The results of Examples 1 to 6 are all superior to the results of Comparative Examples 1 to 4.

[0063]

The traction drive fluid of the present invention can have a high traction coefficient in a wide temperature range.

[Brief description of drawings]

FIG. 1 is a graph showing the relationship between the temperature and the traction coefficient of traction drive fluids of Examples 1 to 3 and Comparative Examples 1 to 4.

FIG. 2 is a graph showing the relationship between the temperature of the traction drive fluid and the traction coefficient of Examples 4 and 5.

FIG. 3 is a graph showing the relationship between the temperature of the traction drive fluid and the traction coefficient of Example 6.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI technical display location C10N 40:04 (72) Inventor Toshio Koto 1134-2 Gongendo, Satte City, Saitama Cosmo General Co., Ltd. Research and Development Center

Claims (3)

[Claims] 1. A compound of the general formula (In the formula, R _{1 to} R ₁₀ may be independently selected from hydrogen or a C _{1 to} C ₃ alkyl group or a cyclohexyl group, and Q _{1 to} Q ₄ may be selected from a C _{1 to} C ₃ alkyl group or a cyclohexyl group. Each of them may be independently selected, and when n _{1 to} n ₄ are 2 to 5, individual groups of a plurality of Q _{1 to} Q ₄ may be independently selected, and n _{1 to} n ₄ are 0 to 5 At least one compound represented by the formula (1) is used as the component (A), and is a thermal copolymer of cyclopentadiene and vinyl aromatic hydrocarbon or a hydride thereof having a softening point of 40 ° C. or higher or A component having a weight average molecular weight of 250 or more is contained as the component (B), and the weight ratio of the component (A) to the component (B) (A)
/ (B) is 85 / 15-97 / 3, The fluid for traction drives characterized by the above-mentioned. 2. A compound as a component (C), which further comprises at least one of the following compounds and has a viscosity at 40 ° C. lower than that of the component (A) used therein. The fluid for a traction drive according to claim 1. (I) dicyclopentadiene or any hydrogen thereof is C
Hydride of compound substituted with _{1 to} C ₃ alkyl group or cyclohexyl group (ii) Hydride of compound in which tricyclopentadiene or any hydrogen thereof is substituted with C _{1 to} C ₃ alkyl group or cyclohexyl group ( iii) hydride of a compound in which tetracyclopentadiene or any hydrogen thereof is substituted with a C ₁ -C ₃ alkyl group or a cyclohexyl group (iv) decalin or any hydrogen thereof is a C ₁ -C ₃ alkyl group or cyclohexyl Compounds substituted with groups 3. A component (A) and a component (B) as defined in claim 1 and a component (C) as defined in claim 2, wherein the weight ratio of the component (A) and the component (B) (A). ) /
(B) is less than 85/15, a traction drive fluid.