JPS63388A - Traction drive fluid - Google Patents

Abstract

PURPOSE:To obtain the title fluid having a high coefficient of traction and excellent heat and oxidation resistance, by using a specified alkane derivative as its principal component. CONSTITUTION:A tetralin (derivative) of formula I (wherein R<5-6> are each H or 1-4C alkyl; p and q are each 1-3) or a naphthalene (derivative) of formula II (a) is reacted with an arylalkyl halide (b) of formula III (wherein R<1-4> and R<7> are each R<5> and at least one of R<1-4> is 1-4C alkyl; r is p; X is halogen) in the presence of a catalyst containing an alkali metal and/or an alkaline earth metal or a Friedel-Crafts catalyst to give an alkane derivative (A) of formula IV which consists of a 2C principal chain having terminal decalin rings and cyclohexane rings, and at least one 1-4C alkyl group attached thereto. If necessary, component A is mixed with various additives appropriately to give the title fluid.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention is applicable to traction drive devices (JJi! friction drive device δ by rolling contact), such as automatic i1j continuously variable transmissions, industrial continuously variable transmissions, hydraulic equipment, etc. Concerning fluids flowing into rivers.

[Prior Art and Problems to be Solved by the Invention] A traction drive fluid used in a traction drive device is required to have a high traction coefficient, stability against heat and liquefaction, and economic efficiency.

In recent years, traction drive devices have become smaller and lighter.
Research is focused on automotive applications. Along with this, the traction drive fluid used in this traction drive device has performance that can be used under various I/Y harsh conditions, especially from low to high temperatures (about -30 to 140°C).
It is required to be able to stably exhibit high performance over a wide temperature range up to

For this reason, it has traditionally been the case that
It has been proposed to use various compounds including No. 9 as a traction drive fluid, but none of them have been fully satisfactory overall in terms of performance.

[Means for Solving the Problems] Therefore, the present inventors have solved the problems of the above-mentioned conventional technology, and have developed a system that has a high traction coefficient over a wide temperature range from low to high temperatures, has a moderate viscosity, and has a comprehensive We conducted intensive research to develop a traction drive fluid with excellent performance.

As a result, we found that among alkane derivatives that have a decalin ring and a cyclohexane ring at both ends of the main chain with 2 carbon atoms, compounds with a specific structure have excellent overall performance. The present invention was completed based on this.

That is, the present invention is characterized in that the main component is an alkane derivative in which at least one alkyl group having 1 to 4 carbon atoms is bonded to a main chain having a j prime number of 2 and having a decalin ring and a cyclohexane ring at both ends. The present invention provides a traction drive fluid that provides

There are various types of such alkane derivatives, but they usually have the general formula: Indicates either 1, 2.3. However, at least one of RI-R'' represents an alkyl group having 1 to 4 carbon atoms.

The compound represented by this general formula [I] can be produced by various methods. For example, R4 in general formula [1]
When is hydrogen, the general formula [wherein R5+R6+P and 'l are the same as above. Tetralin or its derivatives represented by the formula 5, or naphthalene or its derivatives represented by the general formula [wherein R5, R6, q are the same as above] and R', R2, R3, R7 in the general formula 5 , r are the same as in ii7. A styrenic conductor represented by is reacted in the presence of a catalyst containing an alkali and/or an alkaline earth metal.

- General formula [wherein, R1, R2, R3, R5, R6, R', p
, q, and r are the same as above. ] or general formula [wherein R1, R2, R3, R5, R6, R', p,
q and r are the same as above. By producing a compound represented by the formula [formula Medium, R1, R2, R3, R5, R6, R', p
, q, and r are the same as above. ] The compound of the present invention represented by these can be produced.

In addition, instead of the styrene derivative represented by the above general formula [17], the general formula % formula % [wherein R1, R2, R3, R', R7, and r are the same as above, and X is a halogen atom] show. By using the arylalkyl halide represented by the following formula, the undeveloped compound #J represented by the general formula [I] can be produced. In this case, the catalyst may be the alkali-containing and/or alkaline earth metal-containing catalyst described above, or a Friedel-Craft catalyst such as aluminum chloride or ferric chloride.

A specific example of the compound represented by the above general formula [1] is 1-decaryl-2-cyclohexylpropane represented by the formula.

1-decaryl-2-cyclohexyl-2- represented by the formula
Methylpropane.

1-cyclohexyl-2-decarylpropane represented by the formula.

1-cyclohexyl-2-decalyl-2- represented by the formula
Methylpropane.

1-decaryl-2-cyclohexylbutane represented by the formula 2-decaryl-3-cyclohexylbutane represented by the formula.

1-Cyclohexyl-2-decarylbutane represented by the formula.

1-Methyldecaryl-2-cyclohexyl-2-methylpropane represented by the formula or formula CH3.

1-Cyclohexyl-2-methyldecaryl-2-methylpropane represented by the formula or the formula CH3.

Examples include 1-decaryl-2-methylcyclohexylpropane represented by the formula.

Although the traction drive fluid of the present invention is as described above, various additives may be added as appropriate.

[Effects of the Invention] It exhibits a high and stable traction coefficient and is excellent in various overall performances.

Moreover, since the traction drive fluid of the present invention has a high traction coefficient, it is possible to reduce the size and weight of the traction drive device and extend its life.

Therefore, the traction drive fluid of the present invention is
It is widely used in various mechanical products such as continuously variable transmissions for automobiles and industrial use, and even hydraulic equipment.

[Example] Next, the present invention will be explained in more detail with reference to Examples.

Example 1 5μ glass 4 equipped with a stirrer, dropping funnel with gas inlet tube, 8-flow condenser with calcium chloride tube and thermometer
1452 g (11.0 mol) of tetralin was introduced into the second flask while introducing argon gas through the gas introduction tube.
80 g (3,5 mol) of sodium metal and 44,9 g (0,5 mol) of potassium tert-butoxide as promoter
4 mol) and heated to +25°C in an oil bath. After stirring strongly for 1 hour to disperse the metallic sodium, purified α
-Methylstyrene? 08g (6 moles) and Tetrarif 13
2 g (1 mole) of the mixed solution was added dropwise at 125° C. over 4 hours, and after the dropwise addition was completed, the reaction was completed by stirring for an additional hour. After cooling to room temperature, methanol 12 was added dropwise little by little while stirring to decompose unreacted sodium metal. The introduction of argon gas was stopped, and the reaction mixture was washed twice with 1 liter of water, then once with 1 N hydrochloric acid aqueous solution 1β, and further washed with iI! Washed twice with water. After drying the oil layer with anhydrous sodium sulfate.

This dry preservative is separated into a furnace or the liquid is distilled under reduced pressure.
400g of 10.2m+*Hg fraction was obtained at 65-168°C.

400 g of this fraction was placed in a magnetically stirred II2 stainless steel autoclave, and 20 g of a 5% by weight ruthenium-carbon catalyst (IJ, Engelhard Japan) was added, and the mixture was heated at a hydrogen pressure of 50 kg/cm2 G and a reaction temperature of 170°C. The hydrogenation reaction was carried out for 4 hours under these conditions. After cooling, the catalyst was filtered and light components were stripped to obtain 410 g of 1-(1-7'calyl)-2-cyclohexylpropane.

Note that the hydrogenation rate was 99.9% or more. The properties of this product are shown below.

■Refractive index (n20) 1.5031■ Ratio
Weight (15/4'C) 0.9378■Kinematic viscosity
45.59 cst (40℃) 5.145 cst
(100℃) ■ Viscosity index -22 (based on JIS K 2284)
■ Pour point -30,0℃ (based on JIS K 2289) Also, the traction coefficient of this 1-(1-decalyl)-2-cyclohexylpropane can be changed from 40℃ to 140℃.
The results of measurements over the range up to C are shown in FIG.

The traction coefficient was measured using a two-cylindrical friction tester. In other words, the adjacent cylinders of the same size (diameter 52cm, thickness 6cm, radius of curvature IQ mm on the driven side)
Tyco type, drive side is flat type without crowning)
one at constant speed (1500 rpm) and the other at 15
Continuously rotate from 0Orpm to 175Orpm,
A load of 7 kg was applied by a spring to the contact portion of both cylinders, and the tangential force generated between the two cylinders, that is, the traction force, was measured to determine the traction coefficient. This cylinder has bearing steel of 5UJ
-2 Made of mirror finish, maximum Hertz contact pressure is 11
It was 2 kgf/mm2.

In addition, in measuring the relationship between the traction coefficient and oil temperature, the oil temperature was varied from 40°C to 140°C 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 plot of the relationship between

Comparative Example 1 Tetralin 1452 g (11,0 mol), 80 g (3,5 mol) of metallic sodium and 97 g (l, 7 mol) of potassium hydroxide as promoter,
Heated to 35°C. 418 g of purified styrene under stirring
(4,0 mol) and tetralin 132 g (1,
A mixed solution of 0 mol) was added dropwise over 3 hours while maintaining the temperature at 135 to 140°C. After the dropwise addition was completed, the mixture was heated and stirred for 1 hour, and then cooled to room temperature. After decomposing excess metal sodium by dropping methanol little by little while stirring, the mixture was washed with water and a 1N aqueous hydrochloric acid solution, and dried over anhydrous sodium sulfate. The dry explosive was separated from the furnace and the liquid was distilled under reduced pressure to 1N to obtain 400 g of a 70.2 mm'Hg fraction with a lighting temperature of 138 to 145°C.

Analysis of this fraction revealed that 1-(1-tetralyl)-2
- Confirmed to be phenylethane. This fraction 4
After putting 00g into a 12 volume autoclave, 15g
A 5 weight ruthenium-carbon catalyst (manufactured by Nippon Engelhard) was added thereto, and hydrogenation was carried out at a hydrogen pressure of 50 kg/cm2G and a reaction temperature of 170°C for 4 hours. After cooling, the catalyst was filtered and the light components were stripped and analyzed. The hydrogenation rate was 99.9% or more, and this product was 1-(1
-decalyl)-2-cyclohexylethane. The properties of this product are shown below. Moreover, the relationship between the traction coefficient and temperature of this product is shown in FIG.

■ Refractive index (n2') 1.5011■ Ratio
Ball (15/4℃) 0.9338■ Kinematic viscosity
27.48 cst (40℃) 4.204 c
st (100°C) ■ Pour point -35°C or lower (according to JTS K 2289) From Figure 1, this compound has a molecular structure very similar to the compound of the present invention (both have low cyclohexyl alkyl decalin traction coefficients). I understand.

Example 2 5f! 387 g of naphthalene (387 g
．． 02 mol), anhydrous aluminum chloride 20 g (0.02 mol), anhydrous aluminum chloride 20 g (0.
15 mol) and 2.5 g of nitromethane and 240 g of neophyll chloride (1.4
2 mol) was added dropwise over 4 hours, and after the addition, O'
The reaction was completed by stirring at C for 1 hour. Thereafter, water was injected to decompose the anhydrous aluminum chloride, followed by water washing and alkaline water washing, and the oil layer was separated and dried over anhydrous magnesium sulfate. After separating the desiccant from 7P and distilling off nitromethane and naphthalene using a rotary enoheporator, distillation was carried out under reduced pressure.
/O. 160 g of ImmHg fraction was obtained.

When this fraction was analyzed, it was confirmed that the main components were 1-phenyl-2-naphthyl-2-methylpropane and 1-naphthyl-2-phenyl-2-methylpropane. By subjecting this fraction to nuclear hydrogenation in the same manner as in the actual flow side 1, 1-cyclohexyl-2-decalyl-2-methylpropane and 1-decaryl-2-cyclohexyl-2
- A fluid whose main component is methylpropane was obtained. The properties of this product are shown below, and the relationship between the traction coefficient and temperature of this product is shown in FIG.

■ Refractive index (n20) 1.5033 ■ Specific gravity (+
5/4℃) 0.9344 ■ Kinematic viscosity 89.02 cSt (40℃)8
．． 431 cst (100°C) ■ Pour point -12.5°C (based on JIS K 2289) Comparative example 2 1! 198 g of tetralin (1,5
mol) and 20 g (0.15 mol) of anhydrous aluminum chloride were added thereto, and 278 g (3.0 mol) of 5ec-butyl chloride was added dropwise at 40°C with stirring over 6 hours. One reaction was completed by stirring for 30 minutes. Thereafter, water was injected to decompose the anhydrous aluminum chloride, and then the aqueous layer was separated, and the oil layer was washed three times with a 1N aqueous sodium hydroxide solution and further dried over anhydrous sodium sulfate. After that, vacuum distillation is performed, and the score is 95 to 1.
233 g of a 12°0/0.3a+oHg fraction was obtained.

As a result of analysis, it was confirmed that this fraction was mainly composed of bis(5ec-butyl)tetralin. By nuclear hydrogenating this fraction in the same manner as in Example 1, bis(
A fraction containing mainly 5ea-butyl) and y-decalin was obtained. The kinematic viscosity of this product is 12.83 cSt (40℃)
, 2.394cSt (100°C), specific gravity (15/4°C) is 0.8888, and refraction i(n
”) was 1.4823. The relationship between the traction coefficient and temperature of this product is shown in FIG.

From FIG. 1, it can be seen that although this compound has a molecular structure similar to the compound of the present invention (both are decalin derivatives), it has a significantly low traction coefficient.

Comparative Example 3 500 g of naphthalene (3,9
1 mol), 500 g of carbon tetrachloride and anhydrous ferric chloride 2
Add 4g (0.15 mol) and stir at 10-15°.
250 g (1.97 mol) of pencil chloride was added dropwise over 3 hours. After the dropwise addition was completed, the mixture was further stirred at 100C for 30 minutes to complete the reaction. After that, water was injected to decompose the anhydrous ferric chloride, followed by washing with water and alkaline water, separating the oil layer, and dry-exploding it with anhydrous magnesium sulfate. After filtering out the desiccant and distilling off carbon tetrachloride and naphthalene using a rotary evaporator, vacuum distillation was performed to obtain 120 g of a fraction with a temperature of 143 to 146°C/0.3 mmHg.

When this fraction was analyzed, it was confirmed to be a 4/1'lQ compound of 1-benzylnaphthalene and 2-benzylnaphthalene. By nuclear hydrogenating this fraction in the same manner as in Example 1, 1-cyclohexylmethyldecalin 20, 27 cSt (40°C), 3.465 cSt
(100℃), and the specific gravity (+5/4℃) is 0.9
352, and the refractive index (nl) was 1,5008. Moreover, the relationship between the traction coefficient and temperature of this product is shown in FIG.

From FIG. 1, it can be seen that although this compound has a molecular structure similar to the compound of the present invention (both are cyclohexyl alkyl decalins), it has a significantly low traction coefficient.

[Brief explanation of the drawing]

FIG. 1 is a graph showing the relationship between fluid traction coefficient and temperature in Examples of the present invention and Comparative Examples. #＋j Junto Hidemitsu Idemitsu Kosan Co., Ltd.
, New,. Nico

Claims (2)

[Claims] (1) A traction drive characterized in that its main component is an alkane derivative formed by bonding at least one alkyl group having 1 to 4 carbon atoms to a main chain having 2 carbon atoms and having a decalin ring and a cyclohexane ring at both ends. Fluid for use. (2) Alkane derivatives have the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 to R^7 are each hydrogen or carbon number 1]
~4 alkyl group, p, q, r are 1, 2, respectively
, 3. However, at least one of R^1 to R^4 represents an alkyl group having 1 to 4 carbon atoms. ] The traction drive fluid according to claim 1, which is a compound represented by the following.