JPH041794B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a traction drive fluid,
More specifically, the present invention relates to a traction fluid with excellent traction performance which is composed of two specific types of compounds as main components. [Prior Art and Problems to be Solved by the Invention] In general, traction drive fluid is used in traction drive devices (friction drive devices using rolling contact), such as automobile continuously variable transmissions, industrial continuously variable transmissions, It is a fluid used in hydraulic equipment, etc., and is required to have a high traction coefficient, stability against heat and oxidation, and economic efficiency. In recent years, research has been focused on reducing the size and weight of traction drive devices, mainly for automotive applications, and along with this, the traction drive fluid used in these traction drive devices has also been developed to reduce the size and weight of traction drive devices, which can be used under various harsh conditions. In particular, stable high performance over a wide temperature range from low to high temperatures (approximately -30 to 120℃) (high traction coefficient, low viscosity, and excellent oxidation stability) etc.). However, none of the traction drive fluids developed so far can satisfy the above-mentioned required characteristics, and various problems have arisen. For example, a compound that exhibits a high traction coefficient at high temperatures has a high viscosity and a large stirring loss, resulting in low transmission efficiency and also has problems in low-temperature startability. On the other hand, compounds with low viscosity and excellent transmission efficiency have a low traction coefficient at high temperatures, and their viscosity decreases too much at high temperatures, causing problems with the lubrication of traction transmission devices. [Means for Solving the Problems] Therefore, the present inventors have conducted extensive research in order to solve the problems of the above-mentioned conventional technology and develop a traction drive fluid that has excellent performance over a wide temperature range. Ta. As a result, a mixture of a specific compound group with a high traction coefficient at high temperature and a specific compound group with a low viscosity has excellent overall performance as a traction drive fluid, and moreover, a synergistic effect can be obtained by mixing. It was discovered that the traction coefficient was significantly improved by this method, and the present invention was completed. That is, the present invention provides (A) an alkane derivative or cyclohexyldecalin derivative having a decalin ring and a cyclohexane ring on the same carbon, and (B) at least two methyl groups bonded to a main chain having 2 or 3 carbon atoms and having a cyclohexane ring at both ends. or a cyclopentane derivative having two cyclohexane rings as the main component, and is blended at a ratio of 10 to 900 parts by weight of (B) derivative to 100 parts by weight of (A) derivative, and at 100°C. The kinematic viscosity at
The present invention provides a traction drive fluid characterized by having a pressure of 3.0 cSt or more. The traction drive fluid of the present invention contains both the above-mentioned derivatives (A) and (B) as main components.
There are two types of (A) derivatives, one of which is an alkane derivative having a decalin ring and a cyclohexane ring on the same carbon (hereinafter referred to as "A1 type derivative"), and the other is a cyclohexane derivative. Hexyldecalin derivative (hereinafter abbreviated as "A2 type derivative"). Both A1 type derivative and A2 type derivative have both a decalin ring and a cyclohexane ring. In particular, both the decalin ring and the cyclohexane ring are bonded to the same carbon of the alkane derivative.Also, in the A2 type derivative, the decalin ring and the cyclohexane ring are directly bonded to each other. may have one or more substituents such as a methyl group introduced.There are various types of such A1 type derivatives, but usually the general formula [In the formula, R ¹ to R ⁴ each represent hydrogen or a methyl group, R ⁵ represents hydrogen or an alkyl group having 1 to 4 carbon atoms, and l, m, and n are each 1, 2,
3. ] Compounds represented by these can be mentioned. Specifically, the formula 1-(2-decaryl)-1-cyclohexylethane, represented by the formula 1-(1-decaryl)-1-cyclohexylethane, represented by the formula Or expression 1-(2-methyldecalyl)-1-cyclohexylethane, represented by the formula Or expression 1-(1-methyldecalyl)-1-cyclohexylethane, represented by the formula formula Or expression 1-dimethyldecaryl-1-cyclohexylethane, represented by the formula 1-(2-decalyl)-1-(4-
(tert-butyl)cyclohexyl)ethane, formula 1-(1-decalyl)-1-(4-
(tert-butyl)cyclohexyl)ethane, formula 2-(2-decalyl)-2-cyclohexylpropane, represented by the formula Examples include 2-(1-decalyl)2-2cyclohexylpropane represented by In addition, as A2 type derivatives, the general formula is usually [In the formula, R ³ to R ⁵ and l, m, and n are the same as above. ] It is a compound represented by the formula, specifically the formula Examples include 1-cyclohexyl-1,4-dimethyldecalin represented by: On the other hand, there are two types of (B) derivatives used with the above (A) derivatives, one of which has at least two methyl groups bonded to a main chain with 2 or 3 carbon atoms that has cyclohexane rings at both ends. The other is a cyclohentane derivative having two cyclohexane rings (hereinafter abbreviated as "B2 type derivative"). Both the B1 type derivative and the B2 type derivative have two cyclohexane rings, and one or more methyl groups may be introduced into the cyclohexane ring. There are various types of B1 type derivatives, but they usually have the general formula [In the formula, R ⁶ to ^{R 10} each represent hydrogen or a methyl group, and p and q each represent 1, 2, or 3. However, at least one of R ⁶ to R ⁸ represents a methyl group. ] or general formula [In the formula, R ⁹ , R ¹⁰ , p, and q are the same as above,
R ¹¹ to R ¹⁶ each represent hydrogen or a methyl group. However, at least two of R ¹¹ to R ¹⁶ represent a methyl group. ] The compound represented by is opened. Specific examples of compounds represented by the above general formula [] are: 1,2-di(methylcyclohexyl)-2-methylpropane, represented by the formula Examples include 2,3-di(methylcyclohexyl)-butane represented by: In addition, as a specific example of the compound represented by the above general formula [], the formula 1,3-dicyclohexyl-3-methylbutane, represented by the formula 2,4-dicyclohexylpentane, represented by the formula Examples include 2,4-dicyclohexyl-2-methylpentane represented by: In addition, as a B2 type derivative, the general formula is usually [In the formula, R ⁹ , R ¹⁰ , p, and q are the same as above,
R ¹⁷ represents hydrogen or methyl group, r is 1,
Indicates either 2 or 3. ] It is a compound represented by. Specifically, the formula Examples include 1,3-dicyclohexyl-1-methylcyclopentane represented by: The traction drive fluid of the present invention comprises the above-mentioned (A) derivative (A1 type derivative or A2 type derivative) and (B) derivative (B1 type derivative or
B2 type derivative) as the main component,
The derivative (B) is blended at a ratio of 10 to 900 parts by weight to 100 parts by weight of the derivative (A), and has a kinematic viscosity of 3.0 cSt or more at 100°C. The above-mentioned derivative (A) has a high traction coefficient at high temperatures, but its relatively high viscosity causes a large stirring loss, and there are also problems with low-temperature fluidity. On the other hand, although derivative (B) has the advantage of having a low viscosity, it has the problem that the traction coefficient decreases significantly at high temperatures, and the viscosity becomes too low, causing oil film breakage.
However, when the (A) derivative and (B) derivative are mixed so that the kinematic viscosity at 100°C is 3.0 cSt or more, as in the traction drive fluid of the present invention, it has a relatively low viscosity and can be used from low to high temperatures. It exhibits a high traction coefficient over a wide range, and has excellent overall performance without problems such as low-temperature fluidity and oil film breakage at high temperatures. Moreover, the present invention provides an excellent traction drive fluid based on the completely new knowledge that a significant improvement (synergistic effect) in the traction coefficient can be obtained by mixing the (A) derivative and the (B) derivative. be. It is generally known that the traction coefficient has additivity as shown in the following equation (ASLE
Trans.13, 105-116 (1969)), f = 〓 ⁱ C _i f _i C _i : Mixing ratio of i component f _i : Traction coefficient of i component f : Traction coefficient of mixture Also very small (2-3% Although it is said that there is a synergistic effect (SAE 710837 (1971)) in terms of the degree of No known examples. In the present invention, the mixing ratio of (A) derivative and (B) derivative is
The (B) derivative is blended at a ratio of 10 to 900 parts by weight, preferably 15 to 600 parts by weight, per 100 parts by weight of the (A) derivative.
Further, the kinematic viscosity at 100° C. is determined to be 3.0 cSt or more, preferably 3.6 to 10.0 cSt. Here, even if the main components are both derivatives (A) and (B), if the kinematic viscosity at 100°C is less than 3.0 cSt, ensure that the rolling fatigue life of the traction drive device exceeds the rating. This makes long-term operation impossible. The rolling fatigue life of a rolling contact surface largely depends on the relationship between the surface roughness of both contact surfaces and the thickness of the oil film formed there, and this relationship is known as the oil film parameter Λ. Regarding the relationship between Λ and surface fatigue, it is said that if 0.9 < Λ, the life will be longer than estimated (Machine
Design7, 102 (1974)). Based on the above, if we calculate the case where it is applied to an actual bearing as an example of the rolling surface, if it has a viscosity of 3.0 cSt or more at the operating temperature (100°C), preferably 3.6 cSt or more, then at least the rated It is possible to secure a rolling fatigue life that exceeds the (design value). In other words, it is necessary to blend so that the temperature at 100°C is 3.0 cSt or more, preferably 3.6 cSt or more. Furthermore, when used for automobiles, the pour point is preferably -30°C or lower to enable smooth starting at low temperatures. As mentioned above, the traction drive fluid of the present invention contains both derivatives (A) and (B) as main components, but it may also contain various additives as needed. You can also. [Effects of the Invention] As described above, the traction drive fluid of the present invention exhibits a high and stable traction coefficient over a wide temperature range from low to high temperatures, and is excellent in various overall performances, so it can be used in automobiles. It is widely used in various mechanical products such as continuously variable transmissions for commercial and industrial use, and even hydraulic equipment. [Example] Next, the present invention will be explained in more detail with reference to Examples. The traction coefficients in Examples and Comparative Examples were measured using a two-cylinder friction tester. In other words, one of the adjacent cylinders of the same size (diameter 52 mm, thickness 6 mm, driven side is a tycoon type with a radius of curvature of 10 mm, and the driving side is a flat type without crowning) is held at a constant speed (1500 rpm), and the other is held at a constant speed (1500 rpm).
Rotate continuously from 1500prm to 1750rpm, apply a load of 7Kg to the contact area of both cylinders with a spring,
The tangential force generated between the two cylinders, that is, the traction force, was measured to determine the traction coefficient. This cylinder was made of bearing steel SUJ-2 with a mirror finish, and the maximum Hertzian contact pressure was 112 Kgf/mm ² . In addition, when measuring the relationship between the traction coefficient and oil temperature, the oil temperature was varied from 30℃ to 120℃ by heating the oil tank with a heater, and the traction coefficient and oil temperature at a slip rate of 5% were measured. This is a blot of the relationship between Furthermore, in measuring the relationship between the blending ratio of both derivatives (A) and (B) and the traction coefficient, the oil temperature was kept constant and the same method as above was used. Production Example 1 (Production of (A) Derivative) 1000 g of naphthalene, 3000 c.c. of carbon tetrachloride, and 300 g of concentrated sulfuric acid were placed in the glass flask No. 5, and the temperature inside the flask was cooled to 0° C. in an ice bath. Next, 400 g of styrene was slowly added dropwise into the mixture over 3 hours while stirring, and the reaction was completed by further stirring for 1 hour. Thereafter, stirring was stopped and the mixture was allowed to stand still to separate the oil layer. This oil layer was washed three times each with 500 c.c. of 1N aqueous sodium hydroxide solution and 500 c.c. of saturated saline, and then dried over anhydrous sodium sulfate. Subsequently, unreacted naphthalene was distilled off, and then vacuum distillation was performed to reduce the boiling point to 135-148℃/
600g of 0.17mmHg fraction was obtained. Analysis of this fraction confirmed that it was a mixture of 75 wt% 1-(1-naphthyl)-1-phenylethane and 25 wt% 1-(2-naphthyl)-1-phenylethane. Next, 500 c.c. of the above fraction was put into an autoclave No. 1, 20 g of 5% ruthenium-carbon catalyst (manufactured by Nippon Engelhard) was added, and the hydrogen pressure was 50 Kg/
Hydrogenation was carried out for 4 hours under conditions of cm ² and reaction temperature of 200°C. After cooling, the reaction solution was filtered to separate the catalyst. Subsequently, after stripping the light components from the liquid, analysis revealed that the hydrogenation rate was 99.9% or more. Also, this one is 1(1-decalyl)-1-
It was confirmed that it was a mixture of 75 wt% cyclohexylethane and 25 wt% 1-(2-decalyl)-1-cyclohexylethane. Production example 2 (Production of (B) derivative) Ethylbenzene is placed in a glass flask with an internal volume of 5.
2700 g of sodium metal, 58 g of metallic sodium, and 17 g of isopropyl alcohol were heated to 120°C, and while stirring, a mixture of 1100 g of α-methylstyrene and 300 g of ethylbenzene was gradually added dropwise over 5 hours, and then stirred for 1 hour to react. I did this. After the reaction was completed, the oil layer was separated and collected by cooling, and 200 g of methyl alcohol was added thereto, followed by washing three times each with two parts of a 5N hydrochloric acid solution and two parts of a saturated saline solution. Next, after drying with anhydrous sodium sulfate, unreacted ethylbenzene was distilled off using a rotary evaporator, and then distilled under reduced pressure to 0.06 mmH.
1500 g of a fraction with a boiling point range of 104 to 110° C. was obtained. As a result of analysis, this fraction was confirmed to be 2,4-diphenylpentane. Next, 500 ml of this fraction was placed in an autoclave with an internal volume of 1, and 20 g of a nickel catalyst for hydrogenation (manufactured by JGC Chemical Co., Ltd., N-113 catalyst) was added to react at a reaction temperature of 200°C and a hydrogen pressure of 50 kg/cm ^{2 .} Hydrotreated in G. After the reaction was completed, the catalyst was removed, the light components were stripped, and the hydrogenation rate was 99.9.
% or more, and this hydrogenation product was confirmed to be 2.4-dicyclohexylpentane. Example 1 75wt% of 1-(1-decalyl)-1-cyclohexylethane obtained in Production Example 1 and 1-(2-decalyl)
- A fluid consisting of 25 wt% of 1-cyclohexylethane (hereinafter referred to as "fluid A-1") and 2,4-dicyclohexylpentane obtained in Production Example 2 (hereinafter referred to as "fluid B-1") were mixed into fluid A-1. :Fluid B-1 = 3:1 (weight ratio) The properties of the fluid mixed (hereinafter referred to as "mixed fluid-1") are shown in Table 1. Further, the relationship between the traction coefficient and temperature of this mixed fluid-1 is shown in FIG. Further, FIG. 2 shows changes in the traction coefficient at 50° C. of mixed fluids obtained by changing the mixing ratio of the fluid A-1 and the fluid B-1. Comparative Example 1 The properties of the fluid A-1 obtained in Production Example 1 are shown in Table 1, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. Comparative Example 2 The properties of fluid B-1 obtained in Production Example 2 are shown in Table 1, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG.

[Table] Production Example 3 (Production of (A) derivative) The same operation as in Production Example 1 was performed except that 550 g of p-(tert-butylstyrene) was used instead of naphthalene and carbon tetrachloride. As a result of analysis, this fraction was found to contain 1-(1-tetralyl)-1-(p-(tert-butyl)phenyl)ethane and 1-(tert-butyl)phenyl)ethane. -(2-tetralyl)-1-(p-(tert-butyl)phenyl)ethane. Next, the above fraction was subjected to hydrogenation treatment and stripping in the same manner as in Production Example 1. The obtained products were 1-(1-decalyl)-1-(4-(tert-butyl)cyclohexyl)ethane and 1-(2-decaryl)-1-(4-(tert-butyl)). cyclohexyl)
It was a mixture with ethane. Production example 4 (Production of (B) derivative) 2300 g of anhydrous kyumene in the glass flask from 5
40 g of sodium metal and 11 g of isopropyl alcohol were added thereto, heated to 130°C, and 650 g of styrene was added dropwise over 3 hours with strong stirring, followed by stirring for 1 hour to complete the reaction. After stopping the stirring and allowing the mixture to stand and cool, the oil layer was taken out, 200 g of ethanol was added thereto, and the mixture was washed three times each with 2 portions of a 5N hydrochloric acid solution and 2 portions of saturated brine. After drying over anhydrous sodium sulfate, unreacted kyumene was distilled off using a rotary evaporator, and then distilled under reduced pressure to obtain a fraction with a boiling point of 115-125°C/0.13 mmHg. Analysis of this fraction revealed that it was a compound with one molecule of styrene added to kyumene, that is, 1.3-diphenyl-3.
-It was methylbutane. 500 c.c. of the above alkylated product was placed in autoclave 1, 50 g of an activated hydrogenation nickel catalyst (manufactured by JGC Chemical Co., Ltd., N-112 catalyst) was added, hydrogen pressure was 50 Kg/cm ² , and the reaction took place. Hydrogenation was carried out at a temperature of 200°C. After cooling, the reaction solution was filtered to separate the catalyst.
As a result of analysis, it was found that the hydrogenation rate was over 99.9% (confirmed by NMR analysis). When the light components were stripped and analyzed, they were found to be 1,3-dicyclohexyl-3-methylbutane. Example 2 1-(1-decalyl)-1- obtained in Production Example 3
(4-(tert-butyl)cyclohexyl)ethane and 1-(2-decalyl)-1-(4-(tert-butyl)
cyclohexyl)ethane (hereinafter referred to as "fluid A-2") and 1,3-dicyclohexyl-3-methylbutane obtained in Production Example 4 (hereinafter referred to as "fluid B-2"). :
Table 2 shows the properties of the fluid mixed at a ratio of fluid B-2 = 3:7 (weight ratio) (hereinafter referred to as "mixed fluid-2"). Further, the relationship between the traction coefficient and temperature of this mixed fluid-2 is shown in FIG. Further, FIG. 4 shows changes in the traction coefficient at 70° C. of mixed fluids obtained by changing the mixing ratio of the fluid A-2 and the fluid B-2. Comparative Example 3 The properties of fluid A-2 obtained in Production Example 3 are shown in Table 2, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. Comparative Example 4 The properties of fluid B-2 obtained in Production Example 4 are shown in Table 2, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG.

[Table] Production Example 5 (Production of (A) derivative) In Production Example 1, 500 g of α-methylnaphthalene and β-
The reaction, distillation, hydrogenation treatment, and distillation were carried out in the same manner as in Production Example 1 except that 500 g of methylnaphthalene was used, and 1-(1-methyldecalyl)-1-cyclohexylethane and 1-(2-methyldecalyl) were obtained.
A mixture of -1-cyclohexylethane was obtained. Production Example 6 (Production of (B) derivative) Put 1564 g of toluene and 40 g of anhydrous aluminum chloride into a flask with an internal volume of 3, and add 272 g of methallyl chloride and toluene while stirring at room temperature.
92 g of the mixture was gradually added dropwise over 5 hours, and the mixture was further stirred for 1 hour to carry out the reaction. Next, 500 ml of water was added to decompose the aluminum chloride, and the oil layer was separated. The oil layer was washed three times each with one part of a 1N aqueous sodium hydroxide solution and one part of saturated brine, and dried over anhydrous sodium sulfate.
Next, unreacted toluene is removed by distillation, and then distilled under reduced pressure to achieve a boiling point range of 106-113℃ (0.16mmH).
500 g of fraction g) was obtained. The main component of this fraction is
It was 2-methyl-1,2-di(p-tolyl)propane. Next, 500 g of this fraction was placed in an autoclave No. 1, and a nickel catalyst (manufactured by JGC Chemical Co., Ltd.: N-
113) Add 50g, hydrogen pressure 50Kg/cm ² G, temperature 200
Hydrogenation was carried out for 3 hours at °C. As a result of removing light components from the reaction product and analyzing it, the hydrogenation rate was
99.9% or more, the main component is 2-methyl-1,2
-di(4-methylcyclohexyl)propane. Example 3 1-(1-methyldecalyl) obtained in Production Example 5
A fluid consisting of -1-cyclohexylethane and 1-(2-methyldecalyl)-1-cyclohexylethane (hereinafter referred to as "fluid A-") and 2-methyl-1,2-di(4 -methylcyclohexyl)propane (hereinafter referred to as "fluid B-"
3". ), fluid A-3: fluid B-3=
Table 3 shows the properties of the fluid mixed at a ratio of 3:2 (weight ratio) (hereinafter referred to as "mixed fluid-3"). Further, the relationship between the traction coefficient and temperature of this mixed fluid-3 is shown in FIG. Furthermore, 50% of the mixed fluid obtained by changing the mixing ratio of the above fluid A-3 and fluid B-3
Figure 6 shows the change in traction coefficient with temperature. Comparative Example 5 The properties of the fluid A-3 obtained in Production Example 5 are shown in Table 3, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. Comparative Example 6 The properties of fluid B-3 obtained in Production Example 6 are shown in Table 3, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG.

[Table] Production Example 7 (Production of (A) derivative) Production except that 1000 g of dimethylnaphthalene (manufactured by Wako Pure Chemical Industries, Ltd., dimethylnaphthalene mixture) was used instead of naphthalene and carbon tetrachloride in Production Example 1. A mixture of 1-(1-dimethyldecalyl)-1-cyclohexylethane and 1-(2-dimethyldecalyl)-1-cyclohexylethane was obtained by performing reaction, distillation, hydrogenation treatment, and distillation in the same manner as in Example 1. I got it. Example 4 Fluid consisting of 1-(1-dimethyldecalyl)-1-cyclohexylethane and 1-(2-dimethyldecalyl)-1-cyclohexylethane obtained in Production Example 7 (hereinafter referred to as "Fluid A-4") ) and Fluid B-1 obtained in Production Example 2, Fluid A-4:
Table 4 shows the properties of the fluid mixed at a ratio of fluid B-1 = 7:3 (weight ratio) (hereinafter referred to as "mixed fluid-4"). Further, the relationship between the traction coefficient and temperature of this mixed fluid-4 is shown in FIG. Further, FIG. 8 shows changes in the traction coefficient at 60° C. of mixed fluids obtained by changing the mixing ratio of the fluid A-4 and the fluid B-1. Comparative Example 7 The properties of fluid A-4 obtained in Production Example 7 are shown in Table 4, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. Note that the properties of fluid B-1 are also shown in Table 4 and FIG. 7 for reference.

[Table] Production example 8 (Production of (A) derivative) α-methylstyrene was added to the glass flask from 1.
Add 590g of Cumyl Chloride 750 and blow in dry hydrogen chloride gas while stirring at room temperature.
I got g. Next, 2000 g of tetralin and 70 g of titanium tetrachloride were placed in the glass flask in step 5, and the temperature inside the flask was cooled to 0°C in an ice bath. The mixture was slowly added dropwise over 3 hours and stirred for an additional 1 hour to complete the reaction. After post-treatment in the same manner as in Example 1, vacuum distillation was performed to obtain 400 g of a 133-140°C/0.03 mmHg fraction. Analysis of this fraction confirmed that it was 2-tetralyl-2-phenylpropane. Next, 400 g of this material was placed in autoclave 1, and 30 g of 5% ruthenium-carbon powder for hydrogenation (manufactured by Nippon Engelhard Co., Ltd.) was added, under the conditions of hydrogen pressure of 50 Kg/cm ² and reaction temperature of 150°C. Hydrogenation treatment was carried out for 4 hours. After cooling, the same post-treatment as in Production Example 1 was performed and analysis revealed that the hydrogenation rate was 99.9% or more, indicating that this product was 2-decalyl-
It was confirmed that the decalin ring was 2-cyclohexylpropane and contained 90% of the cis form and 10% of the trans form. Example 5 2-decalyl-2-cyclohexylpropane obtained in Production Example 8 (hereinafter referred to as "Fluid A-5")
and Fluid B-2 obtained in Production Example 4, Fluid A
-5:Fluid B-2 The properties of the fluid mixed at a ratio of 1:1 (weight ratio) (hereinafter referred to as "mixed fluid-5") are shown in Table 5. Further, the relationship between the traction coefficient and temperature of this mixed fluid-5 is shown in FIG. Further, FIG. 10 shows changes in the traction coefficient at 50° C. of mixed fluids obtained by changing the mixing ratio of the fluid A-5 and the fluid B-2. Comparative Example 8 The properties of fluid A-5 obtained in Production Example 8 are shown in Table 5, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. In addition, Table 5 and FIG. 9 also show the properties of fluid B-2 for reference.

[Table] Production example 9 (Production of (B) derivative) α-methylstyrene was added to the glass flask from step 3.
1000g and 50g of acid clay and ethylene glycol
50g was added and reacted at 140°C for 2 hours with stirring. After separating the catalyst from the reaction solution, unreacted α-methylstyrene and ethylene glycol were distilled off to obtain 900 g of a fraction with a boiling point of 125-130°C/0.2 mmHg. As a result of NMR analysis and gas chromatography analysis, this fraction was confirmed to be a mixture of 95% linear dimer and 5% cyclic dimer of α-methylstyrene. This fraction was hydrogenated and post-treated in the same manner as in Production Example 2 to obtain a traction drive fluid containing 2,4-dicyclohexyl-2-menylpentane as a main component. Example 6 Fluid A-5 obtained in Production Example 8 and Production Example 9
2,4-dicyclohexyl-2-methylpentane (hereinafter referred to as "fluid B-4") obtained in
Table 6 shows the properties of the fluid mixed at a ratio of fluid A-5: fluid B-4 of 1:1 (weight ratio) (hereinafter referred to as "mixed fluid-6"). Further, the relationship between the traction coefficient and temperature of this mixed fluid-6 is shown in FIG. Further, FIG. 12 shows changes in the traction coefficient at 60° C. of mixed fluids obtained by changing the blending ratio of fluid A-5 and fluid B-4. Comparative Example 9 The properties of fluid B-4 obtained in Production Example 9 are shown in Table 6, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. In addition, Table 6 and
Figure 1 also shows the properties of fluid A-5 for reference.

[Table] Production example 10 (Production of (B) derivative) In a 1-volume glass four-necked flask equipped with a stirrer, dropping funnel, reflux condenser with a calcium chloride tube, thermometer and forked tube with a gas inlet tube. Decalin
200 ml, 9.2 g (0.40 mol) of sodium metal and 11.2 g (0.20 mol) of potassium hydroxide were added. Next, argon gas was introduced into the flask through the gas introduction tube at a rate of 100 ml per minute for 10 minutes, and then the rate was reduced to 10 ml per minute while stirring. Thereafter, the mixture was heated to 135° C. in an oil bath, and 473 g (4.0 mol) of α-methylstyrene was added dropwise over 1 hour. After the dropwise addition was completed, heating and stirring were continued for an additional 30 minutes. After cooling to room temperature, 100 ml of methanol was added dropwise while stirring to decompose unreacted sodium metal. Stop the introduction of argon gas and add 200% of the reaction mixture to each
Washed 3 times with 1 ml of water. The oil layer was dried with anhydrous sodium sulfate and distilled under reduced pressure (139-141℃/0.2mm
Hg) to obtain a fraction containing 250.7 g (2.12 mol) of 1-methyl-1,3-diphenylcyclopentane as a main component. Next, 200 g (0.85 mol) of the above 1-methyl-1,3-diphenylcyclopentane and 10 g of nickel catalyst (manufactured by JGC Chemical Co., Ltd., N-113) were added to a stainless steel autoclave with electromagnetic stirring type 1. ,
The hydrogenation reaction was carried out for 2 hours at a hydrogen pressure of 20 atm and a temperature of 150°C. After the reaction, the liquid from which the catalyst was removed by filtration and the liquid that adhered to the catalyst was collected using xylene were combined, and the xylene was distilled off using a rotary evaporator to obtain 206 g of 1,3-dicyclohexyl-1-methylcyclopentane. A fraction to be used as a component was obtained. Example 7 Fluid A-5 obtained in Production Example 8 and Production Example 10
1,3-dicyclohexyl-1-methylcyclopentane (hereinafter referred to as "Fluid B-5") obtained in
, fluid A-5: fluid B-5 = 1:1 (weight ratio)
(hereinafter referred to as "mixed fluid-7")
The properties are shown in Table 7. Further, the relationship between the traction coefficient and temperature of this mixed fluid-7 is shown in FIG. Furthermore, FIG. 14 shows changes in the traction coefficient of the mixed fluid at 50° C. by changing the mixing ratio of the fluid A-5 and fluid B-5. Comparative Example 10 The properties of fluid B-5 obtained in Production Example 10 are shown in Table 7, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. In addition, Table 7 and
3 also shows the properties of fluid A-5 for reference.

[Table] Example 8 Fluid A-1 obtained in Production Example 1 and Production Example 9
Fluid A-1: Fluid B-
Table 8 shows the properties of the fluid mixed at a ratio of 1:1 (weight ratio) (hereinafter referred to as mixed fluid-8). Also, the relationship between the traction coefficient and temperature of this mixed fluid-8 is shown in Figure 15. Furthermore, the above fluid A-
The change in the traction coefficient at 30℃ of the mixed fluid obtained by changing the blending ratio of 1 and fluid B-4 is shown in the 16th graph.
As shown in the figure. Note that in Table 8 and Figure 15, fluid A-
1. The properties of fluid B-4 are also shown for reference.

[Table] Production Example 11 (Production of (A) derivative) 591 g of α-methylstyrene was placed in a 1-volume glass four-necked flask equipped with a stirrer, a reflux condenser with a calcium chloride tube, a thermometer, and a gas introduction tube.
(5 mol), potassium t-butoxide 2.8 g (0.05
mol) and t-butanol 3.7 g (0.05 mol)
added. Next, argon gas was introduced into the flask through the gas inlet tube at a rate of 10 ml per minute, and the flask was heated at a temperature of 149° C. for 22 hours with stirring. After cooling, the introduction of argon gas was stopped, and the reaction mixture was transferred to a distillation vessel, and unreacted α-methylstyrene was distilled off under reduced pressure. Added to separatory funnel. Furthermore, 300 ml of ether was added to this separating funnel, and after shaking, the aqueous layer was removed. Subsequently, the ether layer was washed twice with 250 ml of water each time, and then the ether layer was dried over anhydrous magnesium sulfate. Next, after distilling off the ether, distillation under reduced pressure (135-137℃/0.2mmHg)
1,4-dimethyl-4-phenyl-1,2,3,4-tetrahydronaphthalene65 with a purity of 96%.
g (yield 11%) was obtained. Next, the 1,4-dimethyl-
59.1 g (0.25 mol) of 4-phenyl-1,2,3,4-tetrahydronaphthalene, 200 ml of methylcyclohexane, and a nickel catalyst for hydrogenation (JGC Chemical)
Co., Ltd., N-113 catalyst) was added, hydrogen pressure was 50 atm,
The hydrogenation reaction was carried out at a temperature of 200°C for 2 hours. After the reaction, the liquid from which the catalyst was removed by filtration and the liquid that adhered to the catalyst were collected with 50 ml of methylcyclohexane were combined, and the methylcyclohexane was distilled off using a rotary evaporator to obtain a purity of 96.
% 1-cyclohexyl-1,4-dimethyldecalin (58.9 g, yield 98%) was obtained. Example 9 1-cyclohexyl-1 obtained in Production Example 11,
4-dimethyldecalin (hereinafter referred to as "fluid A-6") and fluid B-1 obtained in Production Example 2,
Table 9 shows the properties of the fluid (hereinafter referred to as "mixed fluid-9") mixed at a ratio of fluid A-6: fluid B-1 = 85:15 (weight ratio). Further, the relationship between the traction coefficient and temperature of this mixed fluid-9 is shown in FIG. Further, FIG. 18 shows changes in the traction coefficient at 50° C. of mixed fluids obtained by changing the mixing ratio of the fluid A-6 and the fluid B-1. Comparative Example 11 The properties of fluid A-6 obtained in Production Example 11 are shown in Table 9, and the relationship between the traction coefficient and temperature of this fluid is shown in FIG. In addition, Table 9 and Table 1
Figure 7 also shows the properties of fluid B-1 for reference.

[Table] Comparative example 12 Fluid B-2 and fluid B-5 at 1:1 (weight ratio)
Table 10 shows the properties of the fluid mixed in (hereinafter referred to as "mixed fluid-10"). In addition, the relationship between the traction coefficient of this mixed fluid -10 and temperature is calculated as follows:
It is shown in Figure 9. Furthermore, the fluid B-2 and the fluid B-
Figure 20 shows the changes in traction coefficient at 100°C of mixed fluids obtained by changing the blending ratio of No. 5. Comparative example 13 Fluid B-3 and fluid B-4 at 1:1 (weight ratio)
Table 11 shows the properties of the fluid mixed in (hereinafter referred to as "mixed fluid-11"). In addition, the relationship between the traction coefficient and temperature of this mixed fluid -11 is expressed in the second
Shown in Figure 1. Furthermore, the fluid B-3 and the fluid B-
Figure 22 shows the changes in traction coefficient at 60°C of mixed fluids obtained by changing the blending ratio of No. 4.

【table】

【table】 [Brief explanation of drawings]

1st, 3rd, 5th, 7th, 9th, 11th, 13th, 15th, 1st
Figures 7, 19, and 21 are graphs showing the relationship between the traction coefficient and temperature of the fluid in Examples and Comparative Examples. Also, 2nd, 4th, 6th, 8th, 1st
Figures 0, 12, 14, 16, 18, 20 and 22 show the results obtained by mixing two types of fluids obtained in the production example.
It is a graph showing changes in the traction coefficient when the mixing ratio is changed.

Claims (1)

[Scope of Claims] 1 (A) an alkane derivative or cyclohexyldecalin derivative having a decalin ring and a cyclohexane ring on the same carbon; and (B) at least two methyl groups in the main chain having 2 or 3 carbon atoms and having a cyclohexane ring at both ends. The main component is an alkane derivative formed by bonding or a cyclopentane derivative having two cyclohexane rings, and is blended in a ratio of 10 to 900 parts by weight of (B) derivative to 100 parts by weight of (A) derivative, and A traction drive fluid characterized by a kinematic viscosity of 3 cSt or more at 100°C. 2 (A) An alkane derivative having a decalin ring and a cyclohexane ring on the same carbon has the general formula [In the formula, R ¹ to R ⁴ each represent hydrogen or a methyl group, R ⁵ represents hydrogen or an alkyl group having 1 to 4 carbon atoms, and l, m, and n are each 1, 2,
3. ] The traction drive fluid according to claim 1, which is a compound represented by: 3 (A) Cyclohexyldecalin derivative has the general formula [In the formula, R ³ to R ⁵ and l, m, and n are the same as above. ] The traction drive fluid according to claim 1, which is a compound represented by: 4 (B) 2 carbon atoms with cyclohexane rings at both ends
An alkane derivative with at least two methyl groups bonded to the main chain of the general formula [In the formula, R ⁶ to ^{R 10} each represent hydrogen or a methyl group, and p and q each represent 1, 2, or 3. However, at least one of R ⁶ to ^{R 3} represents a methyl group. ] The traction drive fluid according to claim 1, which is a compound represented by: 5 (B) 3 carbon atoms with cyclohexane rings at both ends
An alkane derivative with at least two methyl groups bonded to the main chain of the general formula [In the formula, R ⁹ , R ¹⁰ , p, and q are the same as above,
R ¹¹ to R ¹⁶ each represent hydrogen or a methyl group. However, at least two of R ¹¹ to R ¹⁶ represent a methyl group. ] The traction drive fluid according to claim 1, which is a compound represented by: 6 (B) A cyclopentane derivative having two cyclohexane rings has the general formula [In the formula, R ⁹ , R ¹⁰ , p, and q are the same as above,
R ¹⁷ represents hydrogen or methyl group, r is 1,
Indicates either 2 or 3. ] The traction drive fluid according to claim 1, which is a compound represented by: