JPH0468084A - Fluid for traction drive - Google Patents

Abstract

PURPOSE:To prepare a fluid for traction drive having a high traction coefficient and a high viscosity index economically by compounding a specified quantity of polybutenyl group-contg. succinimide or succinic ester with a specified hydrogenated product of cyclopentadiene type condensed ring hydrocarbon. CONSTITUTION:A cyclopentadiene compd. (e.g. dicyclopentadiene) is thermally homopolymerized or copolymerized with an alpha-olefin and/or a monovinyl-aromatic hydrocarbon (e.g. 2,4,4-trimethylpentene-1) to give a polymeric product composed of at least one polymer. It is a cyclopentadiene type condensed ring hydrocarbon composed mainly of cyclopentadiene trimer to hexamer and has an ND/CD ratio (ratio of H on the norbornene ring double bonds to H on the cyclopentene ring double bonds) of 0.9-1.3. Its hydrogenated product, having a dynamic viscosity of 1-200cSt at 40 deg.C, is compounded with 0.1-40wt.% of polybutenyl group- contg. succinimide or succinic ester (a compd. of the formula) to obtain a fluid for traction drive.

Description

[Detailed Description of the Invention] (Field of Application of Teikoku Hi) The present invention relates to a three-wheel drive river fluid.
More specifically, the main component is cyclopentadiene 7 system 17) 3-6mer, and the ratio of the amount of hydrogen on the norbornene ring double bond to the amount of hydrogen on the cyclopentene ring double bond -H (ND/C
D) is a hydride of a cyclopentadiene condensed ring hydrocarbon having a value of 09 to 1.3, and a polybutenyl group-containing co-I.
This invention relates to a traxilan drive fluid that is blended with phosphoric acid imide or ester as a base oil.

(Prior art) Traction drive devices are equipped with a cylindrical or conical rotating body in which a fluid oil film sandwiched between them loses fluidity under high pressure (hardens into a glass-like state). This is a power transmission device that uses single-sliding friction, and has been widely used in automobiles and industrial machinery.Since it does not use gears like conventional systems, it produces less vibration and noise. High-speed transmission and continuously variable speed are possible.

In recent years, advances in theoretical analysis and the development of materials with high fatigue strength have led to progress in research into improving the performance of equipment and making it smaller and lighter. Excellence is required. The fluid for traction drive must be a lubricating oil with excellent power transmission efficiency (high traction coefficient), and conventionally fluids using polycyclic or condensed ring hydrocarbons such as cyclohexane or cyclopentane as the base stock have been used since 1973.
-24635, Special Publication No. 47-40525, Special Publication No. 40525, Special Publication No. 40525
8-31828, JP 56-145993, JP 59-78296, % JP 62-4785, % JP 62-148596 or JP 62-1533.
Various proposals have been made, such as in No. 95.

(Problem to be solved by the invention) However, the above-mentioned compounds have low traction coefficients, or even if they have high traction coefficients, the manufacturing yield is complicated, or they can only be obtained at low yields (such as For example, in JP-A-62-148596, when cyclopentadiene hydrocarbons are used as starting materials, dicyclopentadiene is selectively partially hydrogenated. By a complicated method of reacting with lower aromatic hydrocarbons and then hydrogenating again, JP-A-62-478
In No. 5, cyclopentadiene and olefin are heated at a relatively low temperature and over a long period of time to form a Diels-Alder adduct, and this is further mixed with cyclopentadiene or conjugated dienes to form a Diels-Alder adduct again. When produced and then hydrogenated, the desired traction drive fluids are obtained using a complex process.

In order to solve such problems, the present inventors first hydrogenated condensed ring hydrocarbons mainly composed of cyclopentadiene trimers and hexamers, which are produced as by-products during the production of cyclopentadiene petroleum resins. It was disclosed that a product obtained by converting into a polyurethane resin is economical and has a high traction coefficient.
No. 7594).

The inventors of the present invention have developed poly-α having branches in the above compound.
- Proposed that by blending a specific amount of olefins, a base oil fluid having a synergistically high traction coefficient could be economically provided (Patent Application No. 1-24039n Mei M
The problem to be solved by the present invention is to provide a new compound other than a branched polyα-olefin that exhibits a synergistically high traction coefficient.

(A means to take the lead in solving the problem) The present inventors have conducted intensive research to obtain a traction drive fluid with a high traction l/factor 'fKf, and as a result, we have found that It has a high traction coefficient by blending a specific amount of succinimide or ester having a polybutenyl group into a hydrogenated condensed ring hydrocarbon mainly composed of cyclopentadiene trimers to hexamers. and the viscosity index V is high (
- It was confirmed that base oil fluid could be provided economically and the present invention was completed.

That is, the present invention provides at least one polymer obtained by thermally polymerizing or thermally copolymerizing cyclopentadiene or cyclopentadiene with α-olefin and/or monovinyl aromatic hydrocarbon. It is a cyclopentadiene-based condensed ring hydrocarbon consisting of a cyclopentadiene-based trimer to hexamer as the main component, and a norbornene ring double bond hydrogen content and a 70 pentene ring double bond hydrogen content. (ND/CD) is 0.9 to 1.37) Polymer hydride is potassium, 4t) C: 'Oh, the amount of liquid to be used is 1 to 1.37)
The present invention provides a traction drive fluid characterized by comprising a succinimide or succinate ester containing polybutenyl in the range of 200 cSt. The traction drive fluid of the present invention can be easily and economically produced and exhibits a high traction coefficient and a high viscosity index. To explain the present invention in detail, the traction drive fluid of the present invention contains hydrogenated cyclopentane as component A. A compound containing a succinic acid sulfate or a succinic acid ester having a polybutenyl group is used as a component B of a hydrogen-based condensed ring hydrocarbon.

The hydrogenated cyclopentadiene-based condensed ring hydrocarbon, which is component A of the present invention, is produced by thermally polymerizing or thermally copolymerizing cyclopentadines or cyclopentadines with α-olefins and/or monovinyl aromatic hydrocarbons. It can be obtained by separating and recovering condensed ring hydrocarbons mainly composed of 3-611 cyclopentadiene derivatives from the polymerization solution by distillation or the like, and then hydrogenating them by a conventional method.

The cyclopentadiene used in the present invention includes cyclopentadiene, dicyclopentadiene, alkyl substituted products thereof, or mixtures thereof.Industrially, cyclopentadiene obtained by steam scrubbing of naphtha etc. It is advantageous to use a cyclopentadiene fraction (CPD fraction) containing 30 weight fractions or more, preferably 50 weight fractions or more.

Further, the CPD fraction may contain an olefinic comonomer copolymerizable with these alicyclic dienes.

Examples of the olefinic comonomer include imprene, piperylene, aliphatic diolefins such as butadiene, and lI'lR olefins such as cyclope/thene. It is preferable that the concentration of these solenoids is low, but it is permissible if the concentration is 10% by weight or less per cyclopentadiene.

Further, as the α-olefins which are the raw materials for copolymerization with cyclopentadiene, Cl-C14, preferably 04-C
1o α-olefins and mixtures thereof; for ethylene and propylene, derivatives from butylene, etc., or decomposition products of C rough wax, etc. are preferably used; these α-olefins include cyclopentagenes; It is industrially preferable to blend less than 4 moles per mole.

Other monovinyl aromatic hydrocarbons that are copolymerization raw materials include styrene, o, m, p-vinyltoluene, α
, β-methylstyrene, etc., and it is industrially preferable to blend less than 3 moles per mole of cyclopentadiene. These monovinyl aromatic hydrocarbons can include indenes such as indene, methyl indene, and ethyl indene, and industrially, the so-called C9 fraction obtained from steam scrubbing of naphtha etc. is used (
・It is advantageous.

In addition, when a monomer such as cyclopentadiene is used as the cyclopentadiene, it is assumed to be 1 mol, and when a dimer is used, it is assumed to be 2 mol. As one of the polymerization or thermal copolymerization methods, the following method may be mentioned. or 160 to 300 in the absence, preferably in an inert gas atmosphere such as nitrogen gas.
1:', preferably 0.1 in the temperature range of 180-280C.
Thermal polymerization or thermal copolymerization is carried out under a pressure capable of maintaining the raw material system in a liquid phase for 1 to 10 hours, preferably 0.5 to 6 hours. After removing the inactive components in the raw materials, unreacted raw materials, and, if necessary, the solvent by distillation or other operations from the polymerization solution under reduced pressure to increased pressure, the second stage of polymerization is then carried out at 160 to 280 tl' under reduced pressure.
C. for 0.5 to 4 hours, it is possible to obtain a polymer which can be used as a base stock for a traction drive fluid containing a desired cyclopentadiene trimer to hexamer as a main component. The ratio (ND/CD) of the hydrogen on the norbornene ring double bond (NI) to the hydrogen t (CD) on the cyclopentene ring double bond of the cyclopentadiene system 3 to 6 is determined by hydrogen nuclear magnetic resonance method ( 5.9 ppm measured by 1H-NMR)
Number of hydrogens on the nearby norbornene ring double bond and 5.6pp
It was determined by the ratio of the number of hydrogens on the cyclopentene ring double bond near m. The conditions for the thermal polymerization or thermal copolymerization described above are set so that the cyclopentadiene polymer has an ND/CD of 0.9 to 1.3, preferably 09 to LO. That is, the cyclopentadiene-based condensed ring hydrocarbon of the present invention is a cyclopentadiene-based fused ring hydrocarbon having the above-mentioned higher ND/CD ratio.
The main component is ~6-mer.

The cyclopentadiene condensed ring hydrocarbon used in the present invention does not necessarily have to have all polymers of each degree of polymerization from trimer to hexamer as a main component, If only low polymers are used as the base stock of the Traxcon drive fluid, the freezing point will be higher than OC, which makes use at low temperatures a problem, and the Traxicon coefficient is also somewhat low. When only the inverse 'c'll & n combination is used, although it shows a high traction coefficient, the kinematic viscosity at 4oC and 100C is somewhat high and there are disadvantages such as energy loss during handling or use. Therefore, it is preferable to use a material containing appropriate amounts of a low polymer and a high polymer and having an appropriate kinematic viscosity.

In addition, the condensed ring hydrocarbon mainly composed of cyclopentadiene trimers to hexamers according to the present invention exhibits a high traction coefficient in a wide temperature range even without hydrogenation treatment, but it also has an odor when handled. It is further hydrotreated to take into account other properties such as oxidation stability and oxidation stability.

The hydrogenation treatment can be carried out in a conventional manner. Tato 1-
1' 70 to 300 C1 in the presence or absence of a solvent using a hydrogenation catalyst such as nickel, palladium or platinum
Preferably a temperature range of 100 to 250C, a hydrogen pressure of 10 to
200 ky/cyn2 (G), preferably 20-12
The hydrogenation treatment may be carried out under a pressure of 0 to μ'z (G) for 0.5 to 20 hours, preferably 1 to 10 hours. After the hydrogenation treatment, the catalyst and, if necessary, the solvent are removed to obtain the desired component A of the traxilan drive fluid. The kinematic viscosity at 40C of the hydride is 1 to 200 cSt, preferably 3
~100 cSt, more preferably 5 to 70 cSt, and the hydride exhibits high traction drive performance over a wide temperature range. In this way, component A of the high-performance traction drive fluid of the present invention can be obtained by a simple process as a by-product of cyclopentadiene resin, and has far superior economic efficiency than conventional known techniques. It is.

The hydrogenated product of the cyclopentadiene-based condensed ring hydrocarbon used in the present invention is, for example, cyclopentadiene, cyclopentadiene and α-olefins.When the raw materials are Matahashi cyclopentadiene and monovinyl aromatic hydrocarbon, gel permini. -Silane chromatography (GPC)
, gas chromatography-mass spectrometry (GC-MS)
) etc., it is estimated that it is a mixture having a structure represented by the following general formulas (1) to [1].In the formula, when R is a group other than ■, It is a saturated hydrocarbon group derived from α-olefins or monovinyl aromatic hydrocarbons copolymerized with .

CI) [■] [1] (In the formula, R is H, a C4 to C14 alkyl group, a substituted or unsubstituted cyclohexyl ethyl group, etc., or a substituted,
unsubstituted bicyclo[4,3,01non-7-yl group, etc.
m is 1-4. ) The succinimide or co-phosphoric acid ester having a polybutenyl group as component B is represented by the following formula (where R represents a polybutenyl group)
(1- represents a divalent saturated aliphatic hydrocarbon group having 2 to 5 carbon atoms, and X represents an integer of 0 to 10); ~
200, preferably about 50 to 100 degrees.

Further, the desirable molecular weight of the succinimide or ester is 800 to 6,000 degrees. Succinimide having a polybutenyl group is generally synthesized by reacting polybutenyl succinic anhydride obtained by reacting polybutene with maleic anhydride and a polyamine. Examples of polyamines include single diamines such as ethylene diamine, propylene diamine, butylene diamine and benchlene diamine; polyalkylene polyamines such as diethylene triamine, triethylene tetramine,
Examples include tetraethylenepentamine, pentaethylenehexamine, di(methylethylene)triamine, diethylenetriamine, tributylenetetramine, and pentapentylenehexamine.

The major component of the present invention has a high traction coefficient of 0.070 to 0.095 even by itself, but this major component KB component has a high traction coefficient of about 0.070 to 0.095.
If it is blended in a range of 1 to 40 weight range, preferably about 3 to 30 weight range, the Traxine carbon coefficient will be significantly increased. If it is too small, the traxilane coefficient will not increase, and if it is too large, the viscosity will increase, making it impractical.

Although it is not clear why the addition of component B improves the traxilane coefficient, it is thought that the polybutenyl group of component B acts synergistically with the major components, resulting in the improvement.

The succinimide or succinimide having a polybutenyl group is usually diluted with mineral oil to about 30 to 60%.

The vehicle drive fluid that is the object of the present invention contains antioxidants, anti-wear additives, and various additives depending on the application.
The yield can be adjusted by adding 05 to 5% by weight, and may further contain a branched polyα-olefin.

(Effects of the Invention) The transportation fluid for driving in the present invention consists of two component base oils. The major component of these, hydrogenated cyclopentadiene condensed ring hydrocarbons, is simply hydrogenated using a specific fraction of the inexpensive by-products from the production of CPD petroleum resins as raw materials. It is easy to manufacture and has excellent economic efficiency.

In addition, component B is commonly used as an additive for lubricating oil.
The Traxyl Indive River Fluid, which is simply a combination of these two components in specific proportions, has excellent economic efficiency. Furthermore, it is unexpected that the combination of these two components exhibits a synergistically higher traction coefficient than the case of component A alone.

(Example) The present invention will be described in detail below with reference to Examples. However, the present invention is not limited to these Examples.

The evaluation of the tractor drive fluids obtained in the comparative examples and examples was carried out in the following manner.

Traction coefficient: ll! g Using a cylindrical friction tester, the drive shaft rotation speed was 1,000 rptn (2,09vn
/s), expressed as the ratio of the transmitted tangential force to the normal load measured at a slip rate of 5%, a normal load of 114 kpf, and a supplied oil temperature of 40C.

Examples 1 to 3 Dicyclopentadiene obtained from steam scrubbing of naphtha 750% by weight, cyclopentadiene fraction 60054 (6,8 2.4.4-mol) and 2.4.4-)limethylpentene - 175% by weight and 400M C8 fraction consisting of fractions other than σ-olefins.2. ．． 7 mol) and the solvent xylene 400f in a nitrogen atmosphere at 260C118kPf/cr112・G.
Thermal polymerization was carried out for 3 hours.

Inert fractions and unreacted raw materials in the raw materials are distilled off from the thermal copolymerization liquid at 239C first under pressure and then under reduced pressure,
Further, while conducting the second stage polymerization, the temperature was maintained under a reduced pressure of 50 TORR for 1 hour to obtain a cyclopentadiene condensed ring hydrocarbon 961 containing the desired tosulcyclopentadiene-α-olefin copolymer. At the same time, 7 clobentadiene resin 3571 having a softening point of 142C was obtained as residue.

ND/CD of cyclopentadiene-based fused ring hydrocarbon is 1
．． It was 0. Next, 2 weights of a nickel-based catalyst was added to 96f of the cyclopentadiene-based condensed R hydrocarbons, and hydrogenated for 4 hours at a hydrogen pressure of 60k)15I'' (G) and a reaction temperature of 180C. A cyclopentadiene-based condensed ring hydrocarbon was obtained.

The compound contains cyclopentadiene 3, 4, and 5.6 mers with a GPC area ratio of 34% by weight, 24% by weight, and 18% by weight, respectively.
It contained 11% by weight and had a kinematic viscosity of 25.5 cSt at 40r.

Next, 30 and 20.10 weight percent of succinimide having the structure of the following formula was added as component B to the hydrogenated cyclopentadiene condensed ring hydrocarbon produced by the loquat process.

(R: polybutenyl group with a degree of polymerization of 24, R''; carbon number 3
(Divalent saturated aliphatic hydrocarbon group) Example 4 10% by weight of fluoric acid imide having the structure of the following formula was added to the A component of Examples 1 to 3 as the B component.

(R; polybutenyl group with a degree of polymerization of 40, R3; carbon number 3
(divalent saturated aliphatic hydrocarbon group) Example 5 A succinic acid ester having the structure of the following formula was blended as component B to component A in Examples 1 to 30 in an amount of 10% by weight.

R-CH-C-OR CH2-C-OR (R; polybutenyl group with an IF degree of about 25) Example 6 10 weight succinate esters having the structure of the following formula were added to the A component of Examples 1 to 3 as the B component. The relationship was mixed.

(R; polybutenyl group with degree of polymerization of 30) Comparative Example 1 Component A alone used in Examples 1 to 3.

Comparative Example 2 Hydrogenated polybutene with an average molecular weight of 400 was used alone.

Comparative Example 3 Linear alkylbenzene (average molecular weight 32o) was blended with the A component of Examples 1 to 3 as another component.

Comparative Example 4 α-
Mainly composed of methylstyrene linear dimer hydride.

The traction coefficients of Examples and Comparative Examples were measured and the results are shown in Table 1.

As is clear from the results in Table 1, the Trafsilane Live River fluid of the present invention has an extremely high traction coefficient and viscosity index, and is also economically superior.

Claims (1)

[Claims] (1) (A) cyclopentadiene or cyclopentadiene consisting of at least one polymer obtained by thermal polymerization or thermal copolymerization of cyclopentadiene and α-olefins and/or monovinyl aromatic hydrocarbons A pentadiene-based condensed ring hydrocarbon, which is a cyclopentadiene-based 3
The main component is a hexamer, and the ratio of the amount of hydrogen on the norbornene ring double bond to the amount of hydrogen on the cyclopentene ring double bond (ND
/CD) is a hydride of a polymer of 0.9 to 1.3,
A fluid for traction drive, characterized in that it has a kinematic viscosity at 40°C in the range of 1 to 200 cSt, and (B) 0.1 to 40% by weight of a succinimide or succinic acid ester having a polybutenyl group is blended therein. .