Derivative of bicyclo [2.2.1] heptane, method for...

Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and...

Reexamination Certificate

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Details

C252S073000, C585S010000, C585S020000

Reexamination Certificate

active

06319879

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The present invention relates to a derivative of bicyclo[2.2.1]heptane with a special structure, and particularly to a derivative of bicyclo[2.2.1]heptane with a special structure having a high traction coefficient under high temperature and an excellent viscosity characteristic under low temperature and therefore useful for fluid for a traction drive, and a method for production of such the useful derivative of bicyclo[2.2.1]heptane with a special structure economically and efficiently.
In addition, the invention relates to fluid for a traction drive, and particularly fluid for a traction drive having a high traction coefficient under high temperature and an excellent viscosity characteristic under low temperature.
RELATED ART
Fluid for a traction drive is used in such machine for traction drive as a continuously variable transmission for automobiles and a continuously variable transmission for industry as a lubricating oil to drive them.
A traction coefficient required for the fluid for traction drive is generally known as depending on the size of the traction drive. The fluid for traction drive with a higher traction coefficient is required for developing a small and light traction drive machine.
For example, in CVT (continuously variable transmission) of traction type that is developed as a continuously variable transmission for automobiles, the fluid for traction drive used for CVT requires to have enough high traction coefficient under high temperature to reach, for example, the lowest within a range of applied temperature than a designed temperature for CVT in order to make size of the CVT small and increase the capacity of its torque transmission.
Besides, the fluid for traction drive requires various performances other than the higher traction coefficient.
A low viscosity, for example, 150 MPa·s or lower is required, for example, in −40° C. to keep excellent starting performance in a cold region.
On the other hand, it is required to suppress volatilization of base oil and keep enough thickness of an oil layer for use under high temperature.
Among them, increasing the traction coefficient under the high temperature does not support decreasing the viscosity under the low temperature. Developing traction oil to realize both these performances was very difficult. Against such background, the inventors of the invention enthusiastically studied and discovered a group of compounds excellent in the traction coefficient under the high temperature (the publication of unexamined applications, Koukai Publication 1995-103387). However, those compounds showed insufficient characteristics of viscosity under the low temperature.
SUMMARY OF THE INVENTION
The invention was achieved in the view aforementioned and for the purpose of providing a derivative of bicyclo[2.2.1]heptane with a high traction coefficient under high temperature and an excellent viscosity characteristic under low temperature and useful for the fluid for a traction drive and also providing a method for producing such derivative economically and efficiently.
Besides, the invention was achieved for the purpose of providing the fluid for traction drive, having a high traction coefficient under high temperature and an excellent viscosity characteristic under low temperature.
As a result of a research series of the inventors, who discovered that derivative of bicyclo[2.2.1]heptane with a special structure having a special structure shows particularly excellent performances as the fluid for traction drive and that the derivative of bicyclo[2.2.1]heptane can be economically and efficiently prepared by dimerization of a special olefinic alicyclic ring compound as a material under a special reaction condition and then by hydrogenation.
In addition, the inventors found as a result of a series of research that a synthetic oil with a special property shows excellent performances as the fluid for traction drive.
The invention has been completed based on these findings.
The followings are the abstract of the invention.
(1) At least one of any compounds of cyclo[2.2.1]heptane, exo-2-methyl-exo-3-methyl-endo-2-[(endo-2-methylbicyclo[2.2.1]hept-exo-3-yl)methyl]bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo-[2.2.1]hept-exo-2-yl)methyl]bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-methylbicyclo[2.2.1]hept-exo-3-yl)methyl]bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo[2.2.1]hept-exo-2-yl)methyl]bicyclo[2.2.1]heptane, endo-2-methyl-exo-3-methyl-exo-2-[(endo-3-methylbicyclo[2.2.1]hept-endo-2-yl)methyl]bicyclo[2.2.1]heptane, or endo-2-methyl-exo-3-methyl-exo-2-[(endo-2-methylbicyclo[2.2.1]hept-endo-3-yl)methyl]bicyclo[2.2.1]heptane, particularly the mixture of exo-2-methyl-exo-3-methyl-endo-2-[(endo-3-methylbicyclo[2.2.1]hept-exo-2-yl)methyl]bicyclo[2.2.1]heptane and exo-2-methyl-exo-3-methyl-endo-2-[(endo-2-methylbicyclo[2.2.1]hept-exo-3-yl)methyl]bicyclo[2.2.1]heptane, the mixture of endo-2-methyl-exo-3-methyl-exo-2-[(exo-3-methylbicyclo[2.2.1]hept-exo-2-yl)methyl]bicyclo[2.2.1]heptane and endo-2-methyl-exo-3-methyl-exo-2-[(exo-2-methylbicyclo[2.2.1]hept-exo-3-yl)methyl]bicyclo[2.2.1]heptane, or the mixture of endo-2-methyl-exo-3-methyl-exo-2-[(endo-3-methylbicyclo[2.2.1]hept-endo-2-yl)methyl]bicyclo[2.2.1]heptane and endo-2-methyl-exo-3-methyl-exo-2-[(endo-2-methylbicyclo[2.2.1]hept-endo-3-yl)methyl]bicyclo[2.2.1]heptane.
(2) A method for producing derivative of bicyclo[2.2.1]heptane represented by the following formula (VII)
(In the formula, m represents 2 or 3 and n represents 1 or 2).
and characterized by dimerizing a bicyclo[2.2.1]heptane ring compound such as 2-methylene-3-methylbicyclo[2.2.1]heptane, 3-methylene-2-methylbicyclo[2.2.1]heptane, etc., of which methylene group and methyl group were substituted and/or a bicyclo[2.2.1]heptene ring compound such as 2,3-dimethylbicyclo[2.2.1]hept-2-ene, etc., of which methyl group was substituted, under the presence of an acid catalyst, preferably a Lewis acid, at 60° C. or lower temperature and hydrogenating the produced dimer under the presence of a catalyst for hydrogenation preferably a nickel catalyst at 200-300° C.
(3) Fluid for a traction drive, characterized by consisting of a synthetic oil having physical properties described the following (a) to (f).
(a) molecular weight: 210 or larger.
(b) kinematic viscosity at 40° C.: 10-25 mm
2
/s
(c) viscosity index: 60 or higher
(d) pour point: −40° C. or lower
(e) density at 20° C.: 0.93 g/cm
3
or higher
(f) traction coefficient at 140° C.: 90% or higher of the coefficient of 2,4-dicyclohexyl-2-methylpentane
(4) Fluid for a traction drive according to (3), wherein a synthetic oil is hydrogenated dimer of at least one alicyclic compound selected from bicyclo[2.2.1]heptane ring compounds, bicyclo[3.2.1]octane ring compounds, bicyclo[3.3.0]octane ring compounds, and bicyclo[2.2.2]octane ring compounds.
(5) Fluid for a traction drive according to (3), wherein a synthetic oil is a compound represented by the following general formula (VIII).
(In the formula, both R
1
and R
2
represent hydrogen atoms or alkyl groups with carbon numbers of 1-3, R
3
represents a methylene group, an ethylene group, or a trimethylene group that may be substituted by a methyl group or an ethyl group in a side chain, r represents 0 or 1, and both p and q represent integral numbers of 1-3).
(6) Fluid for a traction drive consisted of a derivative of bicyclo[2.2.1]heptane represented by the following formula

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