JP2002294265A - Lubricating fluid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a lubricating fluid which has a good low-temperature fluidity and a high viscosity index, exhibits an excellent performance in a wide temperature range from low to high temperatures, is advantageous in industrial production, and is used e.g. for traction drive. SOLUTION: This lubricating fluid contains a norbornane-structure-containing compound represented by formula (1) (wherein R1 and R2 are each H or a 1-4C alkyl group, or R1 and R2 are combined with each other to form a 2-4C alkanediyl or alkenediyl group; R3 and R4 are each H or a 1-4C alkyl group; R5 is a di- to tetravalent organic group having 1-20 carbon atoms and 0-2 oxygen atoms; X is O or S; m and n are each 0, 1 or 2; p is 0, 1, 2 or 3; and q is 1, 2 or 3).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a lubricating fluid particularly suitable for a traction drive.

[0002]

2. Description of the Related Art Traction drive fluids are fluids used in traction drive devices (friction drive devices by rolling contact), for example, continuously variable transmissions for automobiles, continuously variable transmissions for industrial use, hydraulic equipment, etc. It is required to have a traction coefficient, stability against heat and oxidation, economy, and the like.

In recent years, studies have been made on reducing the size and weight of traction drive devices, mainly for automotive applications, and accordingly, the traction drive fluid used in the traction drive device has been subjected to various severe conditions. Performance that can withstand use, especially from low to high temperatures (-30 to 14
Traction coefficient (ratio of tangential force to normal load) over a wide temperature range up to about 0 ° C), having a stable viscosity, appropriate viscosity, excellent thermal stability and oxidation stability, Are required.

It is said that the size of the traction drive device is inversely proportional to the traction coefficient of the traction drive fluid used to the 0.45th power.
As the traction drive fluid having a higher minimum traction coefficient in the operating temperature range is used, the size and weight of the traction drive device can be reduced.

[0005] In addition, a fluid having a low viscosity index has a large viscosity increase at a low temperature, resulting in an increase in fluid agitation resistance and a continuously variable transmission (Continuously Variable).
Low temperature startability of eTransmission (CVT for short) is deteriorated. On the other hand, at a high temperature, the viscosity of the fluid rapidly decreases, which makes it impossible to maintain a proper lubricating oil film, which may cause fatigue damage. Therefore, it is desirable that the viscosity index of the fluid be as large as possible.

As a traction drive fluid having a high traction coefficient at a high temperature and a good fluidity at a low temperature, Japanese Patent Publication No.
JP-A-1-44918, JP-A-1-198693, JP-A-3-95295, and the like disclose compounds having a norbornane ring structure.

[0007]

However, the ester compound disclosed in Japanese Patent Publication No. 61-44918 has an extremely low traction coefficient at high temperatures and lacks thermal stability, so that it cannot be put to practical use. Did not.

The dimer hydride of camphene disclosed in JP-A-1-198693 has a considerably high traction coefficient at high temperatures, but has a pour point of -27.5.
° C, there was a problem with low-temperature fluidity.

Further, the dimerized norbornanes disclosed in JP-A-3-95295 have a high traction coefficient at a high temperature and a good low-temperature fluidity, but have a long synthetic route and are not necessarily advantageous in industrial production. I can't say.

An object of the present invention is to provide a traction drive fluid having good low-temperature fluidity, a high viscosity index, excellent performance over a wide temperature range from low to high, and advantageous for industrial production. And the like to provide a lubricating fluid.

[0011]

Means for Solving the Problems The present inventors have found that a specific norbornane-containing compound has a desired traction performance when used, for example, for traction drive, is easy to synthesize, and is suitable for industrial production. The present invention was found to be advantageous, and the present invention was completed.

That is, according to the present invention, there is provided a lubricating fluid containing a norbornane-containing compound represented by the following general formula (1).

[0013]

Embedded image

[Wherein R ₁ and R ₂ each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or R ₁
And R ₂ represent an interconnected alkanediyl group having 2 to 4 carbon atoms or an alkenediyl group, R ₃ and R ₄ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R ₅ represents A divalent or tetravalent organic group having 1 to 20 carbon atoms and 0 to 2 oxygen atoms, X represents an oxygen atom or a sulfur atom, m and n are integers of 0 to 2,
Is an integer of 0 to 3, and q is an integer of 1 to 3. Preferably, it is for a traction drive.

[0015]

According to the present invention, the low-temperature fluidity is good, the viscosity index is high, and excellent performance over a wide temperature range from low temperature to high temperature (for example, the traction coefficient is high, the Lubricating fluid having excellent heat and oxidation stability) and advantageous for industrial production. In particular, since the lubricating fluid according to the present invention has a high traction coefficient from low to high temperatures, when used for traction drive, the transmission efficiency of various traction drive devices can be improved. As a result, the traction drive device can be reduced in size and weight, output can be increased, and the traction drive device can be widely used for moving parts of various machines, equipment, devices, and the like. Further, since the synthesis route is short, it can be produced at low cost in industrial production, which is extremely useful.

[0016]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The lubricating fluid according to the present invention contains a norbornane-containing compound represented by the following general formula (1).

[0017]

Embedded image

Here, in the general formula (1), R₁And R
₂Are each independently a hydrogen atom, an alkyl having 1 to 4 carbon atoms.
It is a kill group. Also, R₁And R₂Are connected to each other
Alkanediyl group having 2 to 4 carbon atoms or alk
It may be an undiyl group. R ₃And R₄Is it
Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
You. R₅Is 2 to 2 carbon atoms and 0 to 2 oxygen atoms.
It is a tetravalent organic group. X is an oxygen atom or a sulfur atom
It is. m and n are integers of 0 to 2, and p is 0 to 3
And q is an integer of 1 to 3.

Norbornane-containing structuring for use in the present invention
Specific examples of the compound include, for example, di (bicyclo [2.
2.1] Hept-2-yl) ether, di (bicyclo)
[2.2.1] Hept-2-yl) thioether, di
(Tricyclo [4.3.0.1^{2 , 5}] Decane-3-
Yl) ether, di (tricyclo [4.3.0.1
^2,5 Decane-3-yl) thioether, di (tric
Black [4.3.0.1^2,5 ] -7-Decene-3-a
) Ether, di (tricyclo [4.3.0.1^2,
5] -8-Decene-3-yl) ether, (trisic
B [4.3.0.1^{2, 5}] -7-Decene-3-a
)-(Tricyclo [4.3.0.1^2,5] -8-
Decene-3-yl) ether, di (tricyclo [4.
3.0.1.^2,5] -7-Decene-3-yl) thioe
-Tel, di (tricyclo [4.3.0.1^{2, 5}]-
8-decene-3-yl) thioether, di (tetracyclyl)
B [4.4.0.1^2,5. 1^7,10] Dodecane-
3-yl) ether, di (tetracyclo [4.4.0.
1^2,5. 1^7,10] Dodecane-3-yl) thioe
-Tel, (bicyclo [2.2.1] hept-2-yl)
-(Tricyclo [4.3.0.1 ^2,5] Decane-3
-Yl) ether, (bicyclo [2.2.1] hept-
2-yl)-(tricyclo [4.3.0.1^2,5]
-7-decene-3-yl) ether, (bicyclo [2.
2.1] Hept-2-yl)-(tricyclo [4.3.
0.1^2,5-8-Decene-3-yl) ether,
(Bicyclo [2.2.1] hept-2-yl)-(tetra
Lacyclo [4.4.0.1^2,5. 1^{7, 10}] Dode
Can-3-yl) ether, 1,2- (bicyclo [2.
2.1] Hept-2-yloxy) ethane, 1,2-
(Tricyclo [4.3.0.1^2,5] Decane-3-
Yloxy) ethane, 1,2- (tricyclo [4.3.
0.1^2,5] -7-Decene-3-yloxy) eta
1,2- (tetracyclo [4.4.0.
1^2,5. 1^7,10] Dodecane-3-yl) eta
1,2- (bicyclo [2.2.1] hept-2-a
Loxy) propane, 1,2- (tricyclo [4.3.
0.1^2,5Decane-3-yloxy) propane,
1,2- (tricyclo [4.3.0.1^2,5] -7
-Decene-3-yloxy) propane, 1,2- (teto
Lacyclo [4.4.0.1^2,5. 1^{7, 10}] Dode
Can-3-yl) propane, 1,3- (bicyclo [2.
2.1] Hept-2-yloxy) propane, 1,3-
(Tricyclo [4.3.0.1^2,5 Decane-3-a
Loxy) propane, 1,3- (tricyclo [4.3.
0.1^2,5] -7-Decene-3-yloxy) pro
Bread, 1,3- (tetracyclo [4.4.0.1
^2,5. 1^7,10] Dodecane-3-yl) propa
1,2- (bicyclo [2.2.1] hept-2-a
Loxy) butane, 1,2- (tricyclo [4.3.
0.1^2,5Decane-3-yloxy) butane;
1,2- (tricyclo [4.3.0.1^2,5] -7
-Decene-3-yloxy) butane, 1,2- (tetra
Cyclo [4.4.0.1^2,5. 1^7,10] Dodeca
N-3-yl) butane, 1,4- (bicyclo [2.2.
1] Hept-2-yloxy) butane, 1,4- (tri
Cyclo [4.3.0.1^2,5] Decane-3-Iluo
Xy) butane, 1,4- (tricyclo [4.3.0.1
^2,5] -7-Decene-3-yloxy) butane, 1,
4- (tetracyclo [4.4.0.1^2,5. 1
^7,10] Dodecane-3-yl) butane, 1,2- (bi
Cyclo [2.2.1] hept-2-yloxy) penta
1,5- (bicyclo [2.2.1] hept-2-a
Ruoxy) pentane, 1,2- (bicyclo [2.2.
1] Hept-2-yloxy) hexane, 1,6- (bi
Cyclo [2.2.1] hept-2-yloxy) hexa
1,6- (tricyclo [4.3.0.1^2,5]
Decane-3-yloxy) hexane, 1,6- (tricy
Black [4.3.0.1^2,5] -7-Decene-3-a
Loxy) hexane, 1,6- (tetracyclo [4.
4.0.1.^2,5. 1^7,10] Dodecane-3-A
Le) hexane, 1,2- (bicyclo [2.2.1] heptane
To-2-yloxy) heptane, 1,7- (bicyclo
[2.2.1] hept-2-yloxy) heptane,
1,2- (bicyclo [2.2.1] hept-2-ylo
Xy) octane, 1,8- (bicyclo [2.2.1]
Pt-2-yloxy) octane, 1,2- (bicyclo
[2.2.1] Hept-2-yloxy) decane, 1,
10- (Bicyclo [2.2.1] hept-2-yloxy
C) Decane, 1,5- (bicyclo [2.2.1] hept
-2-yloxy) -3-oxopentane, 1,5-
(Tricyclo [4.3.0.1^2,5] Decane-3-
Yloxy) -3-oxopentane, 1,5- (trishi
Black [4.3.0.1^2,5] -7-Decene-3-yl
Oxy) -3-oxopentane, 1,5- (tetracycl
B [4.4.0.1^2,5. 1^7,10] Dodecane-
3-yl) -3-oxopentane, 1,8- (bicyclo
[2.2.1] Hept-2-yloxy) -3,6-di
Oxooctane, 1,8- (tricyclo [4.3.0.
1^2,5] Decan-3-yloxy) -3,6-dio
Xooctane, 1,8- (tricyclo [4.3.0.1
^2,5] -7-Decene-3-yloxy) -3,6-
Dioxooctane, 1,8- (tetracyclo [4.4.
0.1^2,5. 1^7,10] Dodecane-3-yl)-
3,6-dioxooctane, 1,5- (bicyclo [2.
2.1] Hept-2-yloxy) -2,5-dimethyl
-3-oxopentane, 1,5- (tricyclo [4.
3.0.1.^2,5Decane-3-yloxy) -2,
5-dimethyl-3-oxopentane, 1,5- (tricy
Black [4.3.0.1^2,5] -7-Decene-3-a
Ruoxy) -2,5-dimethyl-3-oxopentane,
1,5- (tetracyclo [4.4.0.1^2,5. 1
^7,10Dodecane-3-yl) -2,5-dimethyl-
3-oxopentane, 1,8- (bicyclo [2.2.
1] Hept-2-yloxy) -2,5,8-trimethyl
Ru-3,6-dioxooctane, 1,8- (tricyclo
[4.3.0.1^2,5] Decan-3-yloxy)
-2,5,8-trimethyl-3,6-dioxoocta
1,8- (tricyclo [4.3.0.1^2,5]
-7-decene-3-yloxy) -2,5,8-trime
Cyl-3,6-dioxooctane, 1,8- (tetracy
Black [4.4.0.1^2,5. 1^7,10] Dodecane
-3-yl) -2,5,8-trimethyl-3,6-dio
Oxooctane, 1,3- (bicyclo [2.2.1] hep
To-2-yloxy) -2,2-dimethyl-propane,
1,3- (tricyclo [4.3.0.1^2,5] Big
N-3-yloxy) -2,2-dimethyl-propane,
1,3- (tricyclo [4.3.0.1^2,5] -7
-Decene-3-yloxy) -2,2-dimethyl-pro
Bread, 1,3- (tetracyclo [4.4.0.1
^2,5. 1^7,10Dodecane-3-yl) -2,2
-Dimethyl-propane, 1,1,1-tri (bicyclo
[2.2.1] Hept-2-yloxymethyl) eta
1,1,1-tri (tricyclo [4.3.0.1
^2,5] Decan-3-yloxy) ethane, 1,1,1
-Tri (tricyclo [4.3.0.1^2,5] -7-de
Sen-3-yloxy) ethane, 1,1,1-tri (te
Toracyclo [4.4.0.1^2,5. 1^7,10]
Decane-3-yl) ethane, 1,2,3-tri (bisic
B [2.2.1] hept-2-yloxy) propane,
1,2,3-tri (tricyclo [4.3.0.1
^2,5Decane-3-yloxy) propane,
2,3-tri (tricyclo [4.3.0.1^2,5]-
7-decene-3-yloxy) propane, 1,2-di
(Bicyclo [2.2.1] hept-2-yloxy) be
Senzen, 1,3-di (bicyclo [2.2.1] hept-
2-yloxy) benzene, 1,4-di (bicyclo
[2.2.1] hept-2-yloxy) benzene,
1,2-di (bicyclo [2.2.1] hept-2-yl
Oxymethyl) benzene, 1,3-di (bicyclo [2.
2.1] Hept-2-yloxymethyl) benzene,
1,4-di (bicyclo [2.2.1] hept-2-yl
Oxymethyl) benzene, 2,2-di (4- (bicyclo
[2.2.1] Hept-2-yloxy) phenyl) me
Tan, 2,2-di (4- (2- (bicyclo [2.2.
1] Hept-2-yloxy) ethyloxy) phenyl
L) methane, 2,2-di (4- (bicyclo [2.2.
1] Hept-2-yloxy) phenyl) ethane, 2,
2-di (4- (2- (bicyclo [2.2.1] hept-
2-yloxy) ethyloxy) phenyl) ethane,
2,2-di (4- (bicyclo [2.2.1] hept-2
-Yloxy) phenyl) propane, 2-di (4- (2
-(Bicyclo [2.2.1] hept-2-yloxy)
Ethyloxy) phenyl) propane, and the like.
You.

The method for producing the norbornane-containing compound used in the present invention is not particularly limited, and it can be obtained by various methods. Usually, norbornenes are reacted with active hydrogen in the presence of an acid catalyst. It can be produced by reacting a compound having up to 4 compounds to form an ether or a thioether.

Examples of the acid catalyst include clays such as activated clay and acid clay, mineral acids such as sulfuric acid, hydrochloric acid and hydrofluoric acid, p-toluenesulfonic acid, triflic acid, sulfonic acid groups and sulfate groups. Organic acids such as cation exchange resins, aluminum chloride, ferric chloride, stannic chloride, boron trifluoride, boron tribromide, aluminum bromide, Lewis acids such as gallium chloride, gallium bromide, diethylaluminum Organoaluminum compounds such as chloride and ethylaluminum dichloride, and solid acids such as zeolite, silica, alumina, silica-alumina, and heteropolyacid can be used, and may be appropriately selected in consideration of ease of handling and economic efficiency. The use amount of these catalysts is not particularly limited, but is usually 0.01 to 100% by weight, preferably 0.1 to 100% by weight based on the total amount of norbornenes.
10% by weight.

Compounds having 2 to 4 active hydrogens include, for example, water, 1,2-ethanediol, 1,3-
Propanediol, 1,4-butanediol, 1,5-
Pentanediol, 1,6-hexanediol, 1,8
-Octanediol, 1,10-decanediol, 1,
2-propanediol, 1,2-butanediol, 1,
2-hexanediol, 1,2-octanediol,
1,2-decanediol, diethylene glycol, triethylene glycol, 2,2-dimethyl-1,3-propanediol, dipropylene glycol, 1,2,3-
Propanetriol, 1,1,1-tri (hydroxymethyl) ethane, 1,1,1, -tri (hydroxymethyl) propane, tetra (hydroxymethyl) methane,
1,3-dihydroxymethylbenzene, 1,4-dihydroxymethylbenzene, bisphenol A ethoxylate, 4,4′-isopropylidenediphenol, 4,
4′-ethylidene diphenol, 4,4′-methylidene diphenol, hydroquinone, resorcin, catechol, 1,2,4-trihydroxybenzene, hydrogen sulfide,
Examples thereof include 1,2-ethanedithiol, 1,3-propanedithiol, and 1,4-butanedithiol.

In synthesizing the norbornane-containing compound used in the present invention, a solvent can be added as necessary. The addition of the solvent facilitates handling of the norbornenes, active hydrogen compounds and catalysts during the reaction, or controls the progress of the reaction.

Examples of such a solvent include n-pentane,
n-Hexane, heptane, octane, nonane, decane, etc. and cyclopentane, cyclohexane, methylcyclohexane, most of saturated hydrocarbons such as decalin can be used, and the catalyst is a catalyst having a weak reaction promoting property such as clay. In this case, aromatic hydrocarbons such as benzene, toluene, and xylene, and tetralin can also be used.

The reaction conditions are generally 0 ° C. to 180 ° C.
In the above temperature range, appropriate conditions are set depending on the type of the catalyst, the solvent, and the like. For example, when reacting norbornene and water in the presence of sulfuric acid, the reaction is carried out at room temperature to 100 ° C, preferably 60 ° C or higher.

If the reaction product obtained by the synthesis reaction has an unsaturated bond, it can be saturated by a hydrogenation reaction to obtain the compound of the above general formula (1). However, the method of the hydrogenation reaction is not particularly limited. For example, when dicyclopentadiene is used as a norbornene and reacted with water, a carbon-carbon double bond remains in the product, but hydrogenation of this compound is usually carried out by reacting hydrogen in the presence of a catalyst. This is done by causing As the catalyst used for the hydrogenation reaction, a catalyst known as a so-called hydrogenation catalyst containing one or more kinds of metals such as nickel, ruthenium, palladium, platinum, rhodium, iridium, copper, chromium, molybdenum, cobalt, and tungsten. Can be used. The addition amount of this catalyst is in the range of 0.1 to 100% by weight, preferably 1 to 10% by weight based on the norbornane-containing compound.

The hydrogenation proceeds without solvent, but a solvent can be used. In this case, the type of the solvent is n-pentane, n-hexane, heptane, octane, nonane, decane, or the like. Liquid saturated hydrocarbons such as dodecane, cyclopentane, cyclohexane and methylcyclohexane, ethers such as tetrahydrofuran and dioxane, and alcohols such as isopropanol and isobutanol can be used.

The hydrogenation reaction temperature is usually from room temperature to 250
C., preferably 40 to 200 ° C., and the reaction pressure is from normal pressure to 20 MPa, preferably 0.5 MPa to 10 M
It is within the range of Pa, and can be performed by the same operation as a general hydrogenation reaction.

The lubricating fluid of the present invention may contain other lubricating fluids, if necessary, in addition to the above-mentioned norbornane-containing compound. Examples of other lubricating fluids include various fluids such as oils which have not been used alone as well as those conventionally used as lubricating fluids. For example, mineral substances such as paraffinic mineral oil, naphthenic mineral oil and intermediate mineral oil, alkylbenzene, polybutene, poly-α-olefin, synthetic naphthel, ester, ether and the like can be used in a very wide range of liquid substances. Among them, alkylbenzene, polybutene and synthetic naphthene are preferred. Here, examples of the synthetic naphthene include an alkane derivative having two or more cyclohexane rings, an alkane derivative having at least one decalin ring and one or more cyclohexane rings, an alkane derivative having two or more decalin rings, a cyclohexane ring or a decalin ring. Are compounds having a structure in which two or more are directly bonded. Specific examples of such synthetic naphthenes include 1-cyclohexyl-1-decalylethane, 1,3
-Dicyclohexyl-3-methylbutane, 2,4-dicyclohexylpentane, 1,2-bis (methylcyclohexyl) -2-methylpropane, 1,1-bis (methylcyclohexyl) -2-methylpropane, 2,4-dicyclohexyl- 2-methylpentane and the like can be mentioned.

When the above-mentioned other lubricating fluid is mixed with the norbornane-containing compound, the mixing ratio of the norbornane-containing compound is not particularly limited, and the desired performance (for example, traction performance) and other lubrication to be mixed can be obtained. Although it may be appropriately selected depending on the type of the lubricating fluid, it is usually at least 5% by weight, preferably at least 30% by weight of the entire lubricating fluid.

The lubricating fluid of the present invention may further contain, if necessary, an antioxidant, a rust inhibitor, a detergent / dispersant, a pour point depressant,
Viscosity index improver, extreme pressure agent, anti-wear additive, anti-fatigue agent,
Various additives such as an antifoaming agent, an oiliness improver, and a coloring agent can be added in appropriate amounts. The mixing ratio of the various additives is not particularly limited, and may be generally 0 to 95% by weight, preferably about 1 to 70% by weight of the entire lubricating fluid.

[0032] The lubricating fluid according to the present invention is -30 to 14
The traction coefficient over about 0 ° C. is usually 0.07 or more, preferably 0.08 or more, and the traction coefficient is high from low to high temperatures.

The lubricating fluid according to the present invention has a viscosity index:
Usually it is 10 or more, preferably 20 or more.

The lubricating fluid of the present invention includes traction drive fluid, transmission oil, hydraulic oil, compressor oil,
Although it can be used for electric insulating oil and the like, it is particularly suitable for traction drive of a traction drive device that can be used for various machines, equipment, devices and the like.

[0035]

Next, the present invention will be described based on more detailed examples, but the present invention is not limited to these examples. In the following examples, parts are by weight unless otherwise specified.

Example 1 In a glass reactor, methylcyclohexane 10
0 parts, 100 parts of norbornene, 100 parts of water and 10 parts of 1N sulfuric acid were added, and the mixture was reacted at 80 ° C. for 5 hours with stirring. Next, the mixture was cooled to 40 ° C., 1 part of calcium carbonate was added, and the mixture was stirred at 40 ° C. for 3 hours, and it was confirmed that the aqueous layer became neutral. Then, the mixture was again heated and stirred, water was separated under reflux, and the solid content was removed by filtering the content liquid. After heating under normal pressure nitrogen atmosphere, methylcyclohexane and unreacted norbornene were distilled off. Then, distillation under reduced pressure was carried out, and 95 parts of a fraction having a boiling point of 90 to 126 ° C./0.1 torr (containing a compound having a norbornane structure) was recovered.

The collected fraction was analyzed by gas chromatography, mass spectrometry and nuclear magnetic resonance spectroscopy. As a result, di (bicyclo [2.2.1] hept-2-yl) ether, that is, It was found to be an ether having 14 carbon atoms and 1 oxygen (molecular weight = 206, purity = 94%) represented by 1).

The traction coefficient of the recovered fraction is 4
Using a roller traction coefficient tester, a peripheral speed of 3.1
4 m / s, maximum Hertz pressure 1.49 GPa, slip rate 2%
The oil temperature was measured at 40 ° C. and 100 ° C. under the test conditions described above.

Example 2 A reaction was carried out in the same manner as in Example 1 except that 100 parts of dicyclopentadiene was used in place of norbornene. After the reaction, neutralization treatment was performed in the same manner as in Example 1 to separate water, and the organic layer was filtered to remove solids. Then, the mixture was placed in a stainless steel autoclave, and a nickel diatomaceous earth catalyst (Ni
= 45%), and a hydrogenation reaction was performed for 3 hours under the conditions of a hydrogen pressure of 4.5 MPa and 200 ° C. Next, the content was taken out by cooling to 40 ° C., and filtered to remove the catalyst. Then, in the same manner as in Example 1, methylcyclohexane and dicyclopentadiene hydrogenated product were distilled off, followed by distillation under reduced pressure to obtain a fraction having a boiling point of 135 to 155 ° C./0.1 torr (containing norbornane structure compound) 91 Parts were collected.

The recovered fraction is subjected to gas chromatography.
Analysis, mass spectrum analysis and nuclear magnetic resonance spectrum
As a result of the analysis, di (tricyclo [4.3.0.1
^2,5 -7-Decene-3-yl) ether, that is,
Ether having 20 carbon atoms and 1 oxygen represented by the formula (1)
(Molecular weight = 286, purity = 92%)
Was.

The traction coefficient of the recovered fraction was measured in the same manner as in Example 1.
7, 0.091 at 100 ° C.

[0042]Example 3 In place of norbornene in Example 1, tetracyclo [4.
4.0.1.^2,5. 1^7,10] -3-dodecene 10
The reaction was carried out in the same manner as in Example 1 using 0 parts. reaction
Thereafter, water was separated by neutralization in the same manner as in Example 1.
Next, after removing the solid content in the same manner as in Example 1,
Tylcyclohexane was removed. Furthermore, 0.1tor
Unreacted tetracyclo [4.4.0.1 under reduced pressure of r
^2,5. 1 ^7,10-3-Dodecene is distilled off,
98 parts of the reaction product (containing norbornane structure compound)
Obtained.

The collected reaction product was subjected to mass spectrum analysis, nuclear magnetic resonance spectrum analysis and high performance liquid chromatography analysis, and as a result, di (tetracyclo [4.
4.0.1 ^2,5 . 1 ^7,10 ] dodecane-3-yl) ether, that is, 2 carbon atoms represented by the general formula (1)
4. It was found that the product contained an ether having an oxygen number of 1 (molecular weight = 338) (purity> 95%).

The traction coefficient of the recovered reaction product was measured in the same manner as in Example 1.
108 and 0.095 at 100 ° C.

Example 4 In place of water in Example 1, 1,4-butanediol 44 was used.
And 50 parts of a sulfonic acid type strongly acidic cation exchange resin in place of sulfuric acid.
The reaction was performed at 0 ° C. for 10 hours. After cooling to 40 ° C., the ion-exchange resin was removed by filtration, and then methylcyclohexane and unreacted norbornene were removed under a normal pressure nitrogen atmosphere. Thereafter, distillation under reduced pressure is performed, and the boiling point is 140 to 160 ° C /
0.1 torr fraction (including norbornane structure compound) 1
21 parts were collected.

The collected fraction was analyzed by mass spectrometry, nuclear magnetic resonance spectroscopy and high performance liquid chromatography, and as a result, 1,4- (bicyclo [2.2.
1] Hept-2-yloxy) butane, that is, ether having 18 carbon atoms and 2 oxygen atoms (molecular weight = 278, purity> 90%) represented by the general formula (1).

The traction coefficient of the recovered fraction was measured in the same manner as in Example 1.
4, 0.078 at 100 ° C.

Comparative Example 1 The traction coefficient of an isobutene oligomer hydrogenated product (number average molecular weight: 350), which is known to provide a high traction coefficient, was measured in the same manner as in Example 1. 103 and 0.066 at 100 ° C.

From the above, it was confirmed that in Examples 1 to 4, higher traction coefficients were obtained at 40 ° C. and 100 ° C. than in Comparative Example 1.

In Examples 1-4, it was confirmed that the fluidity was excellent at low temperature (-30 ° C.), the viscosity index was high (all were 20 or more), and the synthesis route was short.

[0051]

As described above, according to the present invention, the low-temperature fluidity, the high viscosity index, the excellent performance over a wide temperature range from low to high, and the industrial production It is also possible to provide a lubricating fluid such as a traction drive fluid, which is also advantageous.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C10N 40:16 C10N 40:16 40:30 40:30

Claims (2)

[Claims] 1. A lubricating fluid containing a norbornane-containing compound represented by the following general formula (1). Embedded image Wherein R ₁ and R ₂ are each independently a hydrogen atom,
An alkyl group having 1 to 4 carbon atoms or an alkanediyl group or an alkenediyl group having 2 to 4 carbon atoms wherein R ₁ and R ₂ are connected to each other, and R ₃ and R ₄ each independently represent a hydrogen atom, 4 represents an alkyl group, and R ₅ represents 2 to 2 carbon atoms having 1 to 20 carbon atoms and 0 to 2 oxygen atoms.
X represents a tetravalent organic group, X represents an oxygen atom or a sulfur atom, m and n are integers of 0 to 2, p is an integer of 0 to 3, and q is an integer of 1 to 3. ] 2. A traction drive system.
3. A lubricating fluid according to claim 1.