WO1989001020A1

WO1989001020A1 - Traction fluid

Info

Publication number: WO1989001020A1
Application number: PCT/JP1987/000561
Authority: WO
Inventors: Narihiko Yoshimura; Hirotaka Tomizawa; Yasuji Komatsu
Original assignee: Toa Nenryo Kogyo Kabushiki Kaisha
Priority date: 1987-07-29
Filing date: 1987-07-29
Publication date: 1989-02-09
Also published as: EP0328641B1; EP0328641A4; EP0328641A1

Abstract

A traction fluid which is prepared by compounding a diester represented by general formula (I) (wherein A' represents an ester bond of -COO- or -OOC-, n represents 1 to 10, R1 groups represent one or two members selected from among a hydrogen atom and an alkyl group having 1 to 8 carbon atoms, and R2 groups represent one or two members selected from among a hydrogen atom and an alkyl group having 1 to 3 carbon atoms) or its derivative is disclosed. This fluid is preferably used in a power transmission unit, particularly a traction drive unit.

Description

Details

Talk Field

Technical field

The present invention relates to a fraction flow, and more particularly to a diester or a diester having two cyclohexyl rings. It relates to TRUXI-J NFLIDE, which is formulated with the derivative as a base oil.

Background technology

In a car or an industrial machine, the drive power is transmitted to the driven parts by the drive drive mechanism. Attention has been paid to transmission certification, and research and development has been actively pursued in recent years. The friction drive mechanism is a rolling mechanism that uses 5 * rubbing, etc. I) A force transmission mechanism, which does not use gears as in the past, and therefore vibrates. In addition, noise is reduced and high speed gear shifting can be performed very smoothly. Automatic

ΦIn the industry, improving fuel efficiency of automobiles is an important issue.However, if a continuously variable transmission is applied by applying a torque drive to the transmission of the automobile, it will always be a problem. Since the engine can be operated in the highest fuel efficiency range, fuel consumption can be reduced by more than 20% compared to the conventional transmission system. It is said that . Recent studies include the development of materials with high fatigue strength and theoretical analysis of the traction mechanism. Also, the correlation between the fraction coefficients at the molecular structure level of the components is gradually being elucidated. Here, the traction coefficient is a rolling friction type dynamic. It is defined as the ratio of the traction generated by slip to the normal load of the contact portion of the tilling body that makes a large contact in force transmission concealment.

The traxion fluid must be a lubricating oil with a high traxation coefficient, and its molecular structure is naphthenic ^ The product has been confirmed to be effective, and as a commercially available product, Santrac ® .1 from Monsanto is widely known. Naphthenic ring Japanese Patent Publication No. 47-35 763 4 discloses a fraction flow having a zirconia or a dicyclone. The patent discloses that the alkan lanterns are hydrogen peroxide-added!] (Alpha Methyl) styrene: ring base It is described that the flux coefficient of the fluid on which the object or the hydridized structure is mounted has a high level c '. Special Japanese Patent Application Laid-Open No. 59-191 797-published discloses a flux for traxion containing a escaping base having a naphthene ring. The addition of aromatic nuclei to dicyclohexyl ester of cyclohexyl ester or dicyclohexyl phthalate by aromatic nuclear hydrogenation The resulting ester is preferred as a fluid for traxin.

As mentioned above, in the automobile industry in recent years, the development of continuously variable transmissions has been actively promoted. The higher the coefficient of fusion, the larger the permissible transmission power can be made with the same equipment, so that the overall equipment can be made smaller and the exhaust gas, which is a public t problem, can be reduced. Outbreak Therefore, it is expected that the maximum value of the friction coefficient is as large as possible. However, even if it is a commercial version of the Traction Field, which is currently considered to have the highest performance, such a Traction Dry However, there is a problem in that the performance that should be satisfied in terms of the friction coefficient when used in a switching device is not η, and the price is still n. In addition, the tract-in-nord proposed in Japanese Patent Publication No. 46-357763 also has a sun-track-like or similar substance as one component. Disclosure of inventions that have problems in performance and price in the same way The inventors have found that a high-traxon tractor is a relatively inexpensive traxin. As a result of intensive research to obtain a fluid, it was concluded that two cyclohexyls were linked to a polyester or a derivative thereof via a chain hydrocarbon. It is possible to economically capture oil fluids that have a higher performance by combining if

The present invention has been completed by confirming that Shigesuke is comparable.

RR:

[Where Λ is an ester bond of 1 C 0 0 — or 1 0 C — n is 1 110 and R is in]-or in is a hydrogen atom And one or two selected from alkyl groups of carbon number 1. δ. One or two kinds of！-'or heterogeneous hydrogen atoms and carbon atoms A nitrogen atom or an S atom selected from the group consisting of 1 to 3 alcohols] and a diester or a derivative thereof. It is about the SHIONFLOW.

A first object of the present invention is to provide a high-performance traction single flow having a high traction coefficient. A second object of the present invention is to provide a traxicon flow that is economical, easily available, and can be applied to a human body.

The tracer fluid according to the present invention is characterized in that two cyclohexyl S chains X are bonded to each other via a branched carbohydrate. Is an induction break, and the A ′ of the ester bond having the above structural formula is -C00 or 100C-, and the carbon of the chain hydrocarbon skeleton is The number π is from 1 to 10, especially from 1 to 4 is preferred. If n is 0, the traction coefficient is low, and if n is 11 or more, the viscosity increases, which is not favorable. This diaspora or its rest is constructed according to the law 4 (5 to 50 est in Γ, particularly preferably 7 to 30 est, and 100. C has a viscosity of 1 to 10 cs, particularly preferably 2 to 6 est, and the diesterno-induced suspension includes amino compounds and c. Oxidation Compounds can be mentioned.

The di-sul can be produced by any of the following methods-the second method is to use divalent compound 4-Hydroxycarboxylic acid compound, ΎH It is a method based on the dani reaction. As the monovalent compound, one having a main chain carbon number of 1 to 10 is selected, and particularly a divalent compound having a carbon number of 1 to 4 is selected. A file is preferred. : In general, ethyl alcohol, 1-propane age, 1-3-butane age, and 1-4-butane age One of them is called out. As cyclohexan-potassium carbonyl oxide, in addition to cyclohexan-potassium carbonate, an alcohol S having 1 to 8 carbon atoms is used. In other words, it is possible to get melancholic IJ to 4-linoleic acid or ethyl acetate: I to Sancarponic acid etc. is the not to good or in, that a key service down mosquitoes Le Bonn acid to shea click b ₀ chome:. lambda Te le of reaction is the a Le co Lumpur and acid in 1 Liu 2 t le ratio It is necessary to carry out the catalyst under the condition of whether or not to go under the acid excess condition. BI: There is a question about the production of the product of norcoal. to that of the奵to have _u sum et adopted, divalent § Le:] one le of compound 1 I le in pairs Shi駁^0, '5 ^ί¾ ΐ Le (good teeth rather is especially 2 - The response is about 150 to 250>, which is preferable. The response time is 10 to 40 hours, and the preferred response time is 15 to 25 hours. ) !: It is good to reduce t>, but 'II; is preferable because of the reaction operation. Under these conditions, the excess acid acts as a catalyst. Also, an appropriate amount of styrene or toluene alkenylbenzene as a solvent can be added. By adding a solvent, the reactivity can be easily controlled. The reaction did not take place in the course of the reaction.-The water that was formed; one shot, but when the water became twice as large as the alcohol, the reaction occurred. End- The excess acid is neutralized with an aqueous solution of aluminum and removed by washing with water. If an acid is used that is difficult to remove in the alkaline washing, use 2 to 2.5 moles of the acid and react with a catalyst. As a catalyst, phosphoric acid, p-toluenesulfonic acid, sulfuric acid, etc. can be used, and β is used in view of increasing the reaction rate and increasing the ester yield. Using S is also preferred. The ester compound of the present invention can be obtained by subsequently distilling the reaction product under reduced pressure to elute water and a solvent.

The second ^ construction method of diester is the one-step reaction of cyclohexyl + nordide with a dicarboxylic acid having 3 to 12 carbon atoms per chain. It is a method based on As a cyclohexanol compound, a compound having a carbon number of 1 to 8 in addition to sanol, such as methyl U, is used. Especially, it is better to use the knives that can be used for the nozzles. As an acid, it has 3 to 12 carbons! Since ¾-is 仃 <J, preferably the ί chain has 3 to 6 even carbon atoms, for example, malonic acid, succinic acid In the _π- esterification reaction including acid, glutaric acid 0, etc., the reaction between alcohol and acid is carried out in a molar ratio of 2: 1 or in an excess of var-J. On the other hand, in the former, there is a possibility that by-products of monocarboxylic acid may be formed, but the excess of phenol is preferable. That is, the cyclohexanol compound reacts with dicarbonyl at a rate of 2.5 to 5 times. The reactivity is between 150 and 250, Preferably, it is 170-230 ° C, and the reaction time is 10- /! 0 hours, preferably 15 to 25 hours. The reaction pressure may be increased or reduced pressure, but normal pressure is preferred in terms of the reaction operation. Also, an appropriate amount of an alkylbenzene such as xylene or toluene can be added as a solvent. By adding the solvent, the reaction and the temperature can be easily controlled. As the reaction proceeds, the generated water evaporates, but the reaction is terminated when the water becomes twice as high as that of dicarponic acid. As the catalyst, use is made of phosphorus M, p: northenesulfonic acid, sulfuric acid or the like. The use of phosphoric acid is most preferred for increasing the reaction rate and increasing the ester yield. The jester compound of the present invention can be obtained by finally distilling the reaction product under reduced pressure to distill water, a solvent and an excess of alcohol.

In the present invention, the ester of succinic acid and cyclohexanol, for example, has a traction coefficient of 0.1. 02 to 0.106. Therefore, high performance can be achieved even if the Gestell is applied alone to the truncation drive device iS. A second component may be appropriately added to the polyester. In other words, as a second component, it has a cyclohexyl ring of diester and has a synergistic effect to exhibit an effect of improving the traction coefficient, which is also inexpensive. By selecting a component that has excellent viscosity characteristics and blending the second component into the polyester, it is possible to obtain a fractional flow more economically. it can . The amount of the second component is usually from 0.01 to 90% by weight, particularly preferably from 0.1 to 70% by weight. Various additives can be added to the fraction flow of the present invention according to the intended use. That is, if the traction device is subjected to high temperatures and heavy loads, one or more additives such as antioxidants, antiwear agents, or antioxidants may be used. It can be added at about 0.01 to 5% by weight. Similarly, when a high viscosity index is required, a known viscosity index improver may be combined with 1 to 10% by weight.

In the present invention, a torque fluid is a device S that transmits a rotating torque by point contact or line contact, and has a structure similar to these. Refers to a field used in a transmission device. The fraction fluid of the present invention has a higher fraction coefficient than conventionally known fluids, and depends on properties such as viscosity, but is different from the conventional product. It has a higher friction coefficient of 5 to 15 ° / ₀ . For this reason, the fluid of the present invention has relatively low power transmission equipment such as internal combustion engines of small passenger cars and the like, as well as power generation machines and food production machines. Of course, the present invention can also be applied favorably to a fraction drive device such as a high-powered industrial machine.

The fraction flow of the present invention has a significantly higher fraction coefficient than known fluids, but for any reason, the fraction flow is high. It is not yet completely understood how to represent the shear coefficient. Basically, it is thought that the fraction fluid of the present invention is based on a specific molecular structure. F. The flux of the present invention is a ester, which is a diester having two cyclohexyl rings in a compound molecule. However, due to the two ester bonds, an intermolecular twin force acts between the molecules. It is considered that this dipole force changes the fluid into a stable glassy state under the high load condition of the traktion device, and increases the anti-shearing force. In addition, the traxone fluid of the present invention has an appropriate bending because the basic carbon atom is ester-bonded to two cyclo π-hexyl rings. It has a characteristic structure. Therefore, when the load of the tractor π-unit is high, the presence of the cyclohexyl ring and the chain-like hydrocarbon bond is also determined as V ^; It is thought that when they are released from the load, they quickly leave and become fluidized.

Best mode for carrying out the invention

¾Examples 4 ~ 4

The compound [A] of the present invention was synthesized by the following method.

First, succinic acid 1183 and cyclohexanol 2502 (2.5 moles per mole of succinic acid) were collected in a reaction vessel, and phosphoric acid was removed. A single S% of the whole holiday was added. Next, the reaction vessel was ripened to 180 ° C, and reacted at a temperature of 180 to 21 (TC at a constant / lower temperature. The water generated as the reaction progressed was agitated. The heating was stopped when the molar amount of the acid became twice as much as that of the acid.The reaction product was cyclohexanol succinate ester, and the unreacted material was cyclohexane. Remove unreacted substances from mixture with alcohol and phosphoric acid For this purpose, pure washing (A1) was isolated after washing with alkaline and vacuum distillation.

According to the method of Oka, the following materials (A2 to A4) were synthesized using the following raw materials.

Λ 2… Cyclohexanol and malonic acid

Λ 3… Ethylene glycol and cyclohexane sulfonic acid (acid excess)

A a… 1,3-butanediol and cyclohexancarbonic acid (acid excess)

Next, the traction coefficient of the thus produced polyester was determined. The measurement conditions of the fraction coefficient are as follows.

Measuring device: Soda type 4 Roller trasion testing machine Test conditions: Oil temperature 20 ° C, Roller temperature 3 (TC

Average Hertz pressure 1.2 GPa, Rolling speed 3.6 / S Sliding rate 3.0%

As shown in Fig. II, the fractionation fluid of the invention of the present invention has outstandingly superior fractionation performance as compared with the conventional fractionation flow. I understood.

Comparative Examples 1 to 4

As comparative samples, commercially available fractionation flow B (Monthant, Santrac), polybutene C (average molecule 900), commercial version Naphthene-based fluid D (having〗 to 3 cyclic π-hexyl rings), and dicyclohexyl Using a phosphoric acid diester, the traxion coefficient was measured by the method shown in Examples. As a result, as shown in Table 1, each of the comparative samples had a transaction coefficient of 10 to 15% as compared with the diester compound of the present invention. _U knew small things

Table 1

Industrial applicability

The present invention relates to a runaway for a fraction containing a diester having two cyclohexyl rings and a chain hydrocarbon as a skeleton, which is an extremely high fraction. It has a shear coefficient. Also, excellent teeth be viscosity characteristics ^¾ value also of the Ru Oh.

Therefore, the power transmission device, especially the tractive drive

If used for ^, the shear force under heavy load can be dramatically increased, so that the equipment can be miniaturized and supplied economically. effective .

Claims

(υ — general formula

RI

[In the formula, A 'is an ester of one COO O or -00 C-ϋ', η is Tono I 0, R is 1 is η or heterogeneous hydrogen source. One or 2 W and R 2 selected from an alkyl group having 1 to 8 carbon atoms or one or more m and a hydrogen atom and an alkyl group having 1 to 3 carbon atoms; The element is selected from the group consisting of the following elements: a gesture symbol indicated by ^ Fluid.

Di. I. The R の of the chain is one or more of the same or different and is selected from a hydrogen atom and an alkyl group having 1 to 4 carbon atoms. The field shown.

(3) The first term in the range of the request where the η of the guest is 1 to 4

The ') rule of ¾.

('1) The fluid according to claim 18, wherein R 2 of the ester is any one of a hydrogen atom and a methyl group.