EP0328642A1 - Fluide de traction - Google Patents

Fluide de traction Download PDF

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Publication number
EP0328642A1
EP0328642A1 EP87904959A EP87904959A EP0328642A1 EP 0328642 A1 EP0328642 A1 EP 0328642A1 EP 87904959 A EP87904959 A EP 87904959A EP 87904959 A EP87904959 A EP 87904959A EP 0328642 A1 EP0328642 A1 EP 0328642A1
Authority
EP
European Patent Office
Prior art keywords
traction
traction fluid
fluid
olefin
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP87904959A
Other languages
German (de)
English (en)
Other versions
EP0328642B1 (fr
EP0328642A4 (fr
Inventor
Narihiko Yoshimura
Hirotaka Tomizawa
Yasuji Komatsu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tonen General Sekiyu KK
Original Assignee
Tonen Corp
Toa Nenryo Kogyyo KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tonen Corp, Toa Nenryo Kogyyo KK filed Critical Tonen Corp
Publication of EP0328642A4 publication Critical patent/EP0328642A4/fr
Publication of EP0328642A1 publication Critical patent/EP0328642A1/fr
Application granted granted Critical
Publication of EP0328642B1 publication Critical patent/EP0328642B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids

Definitions

  • This invention relates to a traction fluid. More particularly, the present invention is concerned with a traction fluid comprising a diester or its derivative having two cyclohexyl rings, and a branched poly- ⁇ -olefin as the base oil.
  • Traction drive power transmissions which transmit power to a driven part through a traction drive mechanism, have attracted attention in the field of automobiles and industrial machinery, and in recent years research and development thereon has progressed.
  • the traction drive mechansim is a power transmitting mechanism using a rolling friction. Unlike conventional drive mechanisms it does not use any gears, which enables a reduction in vibration and noise as well as a smooth speed change in high-speed rotation.
  • An important goal in the automobile industry is improvement in the fuel economy of automobiles. It has been suggested that if the traction drive is applied to the transmission of automobiles to convert the transmission to a continuous variable-speed transmission the fuel consumption can be reduced by 20% or more compared to conventional transmission systems since the drive can always be in the optimum speed ratio.
  • traction coefficient is defined as the ratio of the tractional force which is caused by slipping at the contact points between rotators which are in contact with each other in a power transmission of the rolling friction type to the normal load.
  • the traction fluid is required to be comprised of a lubricating oil having a high traction coefficient. It has been confirmed that a traction fluid possessing a molecular structure having a naphthene ring exhibits a high performance. "Santotrack ®" manufactured by the Monsanto Chemical Company is widely known as a commercially available traction fluid. Japanese Patent Publication No. 35763/1972 discloses di(cyclohexyl)alkane and dicyclohexane as traction fluids having a naphthene ring.
  • the present inventors have made extensive and intensive studies with a view to developing a traction fluid which not only exhibits a high traction coefficient but which also is low in cost. As a result, they have found that the incorporation of a specified amount of branched poly- ⁇ -­olefin into a diester or its derivative in which two cyclohexyl rings are connected through a linear chain hydrocarbon can provide an economical, high-performance base oil fluid, and achieved the present invention.
  • the present invention relates to a traction fluid characterized by being a blend of a diester or its derivative represented by the following general formula wherein A′ is an ester linkage of -COO- or -OOC-, n is an integer of 1 to 10, R1 is independently selected from a hydrogen atom and alkyl groups having 1 to 8 carbon atoms, and R2 is independently selected from a hydrogen atom and alkyl groups having 1 to 3 carbon atoms: with 0.1 to 95% by weight of a branched poly- ⁇ -olefin.
  • the first object of the present invention is to provide a high-performance traction fluid having a high traction coefficient.
  • the second object of the present invention is to provide a traction fluid which is not only economical but also readily available and easily applicable to transmissions.
  • the traction fluid of the present invention comprises a base oil comprised of two components, i.e., component A comprised of a diester or its derivative, and a specific amount of a component B comprised of a branched poly- ⁇ -olefin.
  • component A is a diester or its derivative having two cyclohexyl rings and is represented by the above-mentioned structural formula.
  • A′ of the ester linkage is -COO- or -OOC-, and the number. n. of the carbon atoms in the hydrocarbon skeleton is 1 to 10, preferably 1 to 4.
  • n is zero, the traction coefficient is low while when n is 11 or more the viscosity is unfavorably high.
  • This diester or derivative thereof can be prepared by the methods stated below and has a viscosity of 5 to 50 cst, preferably 7 to 30 cst at 40°C, and 1 to 10 cst, preferably 2 to 6 cst, at 100°C.
  • the derivative includes an amino compound, an ether compound, etc.
  • the component A can be prepared by any of the following methods.
  • the first method comprises an esterification reaction of a dihydric alcohol with a cyclohexanecarboxylic acid compound.
  • the dihydric alcohol is selected from the group consisting of those having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.
  • examples of the dihydric alcohol include ethylene glycol. 1,3-propanediol, 1,3-butanediol and 1,4-butanediol.
  • cyclohexanecarboxylic acid compound examples include, besides cyclohexanecarboxylic acid, those having an alkyl group with 1 to 8 carbon atoms, e.g., methylcyclohexanecarboxylic acid, ethylcyclohexanecarboxylic acid, etc. Cyclohexanecarboxylic acid is particularly preferred.
  • the esterification reaction is conducted with an alcohol/acid molar ratio of 1:2, or in the presence of an excess amount of the acid.
  • the former method requires the use of a catalyst and has the additional disadvantage that a monoalcohol is produced as the by-­product. Therefore, it is preferred that the esterification reaction be conducted in the presence of an excess amount of the acid.
  • reaction temperature is about 150 to 250°C, preferably 170 to 230°C, and the reaction time is 10 to 40 hr, preferably 15 to 25 hr.
  • the esterification reaction may be conducted under either elevated or reduced pressures, it is preferred that the reaction is conducted at atmospheric pressure from the standpoint of ease of reaction operation. Under this condition the excess acid serves as a catalyst.
  • An alkylbenzene such as xylene or toluene can be added in a suitable amount as a solvent. The addition of the solvent enables the reaction and temperature to be easily controlled.
  • the reaction proceeds the water which forms during the reaction evaporates.
  • the reaction is terminated when the amount of the water reaches, on a mole basis, twice that of the alcohol.
  • the excess acid is neutralized with an aqueous alkaline solution and removed by washing with water.
  • the reaction is conducted using the acid in an amount of 2 to 2.5-fold mol excess over the alcohol in the presence of a catalyst.
  • the catalyst include phosphoric acid, p-toluenesulfonic acid, and sulfuric acid.
  • the most preferable catalyst is phosphoric acid because it enhances the reaction rate and increases the yield of the ester.
  • the reaction product is finally distilled under reduced pressure to remove water and the solvent thereby obtaining the diester compound of the present invention.
  • the second method of producing the component A of the present invention comprises esterification of a cyclohexanol compound with a dicarboxylic acid having 3 to 12 carbon atoms.
  • the cyclohexanol compound include, besides cyclohexanol, those having an alkyl group with 1 to 8 carbon atoms, e.g., methylcyclohexanol and tertbutylcyclohexanol. Cyclohexanol is particularly preferred.
  • the dicarboxylic acid includes one having 3 to 12 carbon atoms in its main chain, preferably one having 3 to 6 carbon atoms in its main chain. Examples of the dicarboxylic acid include malonic acid, succinic acid and glutaric acid.
  • the esterification reaction is conducted in an alcohol/acid molar ratio of 2:1 or in the presence of an excess amount of the alcohol.
  • the esterification reaction is conducted in the presence of an excess amount of the alcohol.
  • 1 mol of the dicarboxylic acid is reacted with the alcohol in 2.5 to 5-fold mol excess.
  • the reaction temperature is about 150 to 250°C, preferably 170 to 230°C, and the reaction time is 10 to 40 hr, preferably 15 to 25 hr.
  • the esterification reaction may be conducted under either elevated or reduced pressures, it is preferred that the reaction be conducted at atmospheric pressure from the standpoint of ease of reaction operation.
  • An alkylbenzene such as xylene or toluene can be added in a suitable amount as a solvent.
  • the addition of the solvent enables the reaction temperature to be easily controlled.
  • the water which has been formed during the reaction evaporates.
  • the reaction is terminated when the amount of the water reaches twice by mol that of the alcohol.
  • Phosphoric acid, p-toluenesulfonic acid or sulfuric acid can be used as a catalyst.
  • the most preferable catalyst is phosphoric acid because it enhances the reaction rate and increases the yield of the ester.
  • the reaction product is finally distilled under reduced pressure to remove the water, solvent and excess alcohol thereby obtaining the diester compound of the present invention.
  • the poly- ⁇ -olefin component B has either a quaternary carbon atom or a tertiary carbon atom in its main chain and is a polymer of an ⁇ -olefin having 3 to 5 carbon atoms or the hydrogenation product thereof.
  • Examples of the poly- ⁇ -olefin include polypropylene, polybutene, polyisobutylene and polypentene and the hydrogenation products thereof. Polybutene, polyisobutylene and hydrogenation products thereof are particularly preferred.
  • the polyisobutylene is represented by the following structural formula:
  • the hydrogenation product of the polyisobutylene is represented by the following structural formula:
  • the degree of polymerization, n is 6 to 200.
  • polybutene and polyisobutylene used may be commercially available ones, they may also be produced by conventional and well known polymerization methods.
  • the hydrogenation product thereof is produced by reacting polyisobutylene or the like in the presence of hydrogen.
  • the molecular weight of the poly- ⁇ -olefin is preferably in the range of 500 to 10,000, more preferably in the range of 900 to 5,000.
  • the molecular weight can be adjusted by suitable methods such as decomposition of a poly- ⁇ -olefin having a high molecular weight and mixing of poly- ⁇ -olefins having different molecular weights.
  • OCP ⁇ -olefin copolymer
  • the component A in the present invention e.g., a diester of succinic acid with cyclohexanol, exhibits a traction coefficient of 0.102 to 0.106, while the component B, e.g., polybutene, exhibits a traction coefficient of 0.075 to 0.085.
  • a further improved traction fluid can be obtained by blending the component A with 0.1 to 95% by weight, particularly 10 to 70% by weight, of the poly- ⁇ -­olefin of the component B.
  • the gem-dialkyl group in the component B cooperates with the cyclohexyl ring in the component A to exhibit a synergistic effect (with respect to improvement in the traction coefficient).
  • the component B is inexpensive and exhibits excellent viscosity characteristics, a traction fluid can be economically obtained by blending component A with 0.1 to 95% by weight of component B without lowering the traction coefficient.
  • Various additives may also be added to the traction fluid of the present invention depending upon their applications. Specifically, when the traction device undergoes a high temperature and a large load at least one additive selected from among an antioxidant, a wear inhibitor and a corrosion inhibitor may be added in an amount of 0.01 to 5% by weight. Similarly, when a high viscosity index is required a known viscosity index improver is suitably added in an amount of 1 to 10% by weight. However, since the use of polymethacrylates or olefin copolymers lowers the traction coefficient, it is preferred that, if present, they are used in an amount of 4% or less by weight.
  • traction fluid as used in the present invention is intended to mean a fluid for use in devices which transmit a rotational torque through point contact or line contact, or for use in transmissions having a similar structure.
  • the traction fluid of the present invention exhibits a traction coefficient higher than those of conventionally known fluids, i.e., exhibits a traction coefficient 5 to 15% higher than those of the conventional fluids, although the value varies depending on the viscosity. Therefore, the traction fluid of the present invention can be advantageously used for relatively low power drive transmissions including internal combustion engines of small passenger cars, spinning machines and food producing machines, as well as large power drive transmissions such as industrial machines, etc.
  • the traction fluid of the present invention is remarkably superior in its traction coefficient relative to conventional fluids.
  • the reason why the traction fluid of the present invention exhibits a high traction coefficient is not yet fully understood. However, basically, the reason is believed to reside in the unique molecular structure of the traction fluid of the present invention.
  • the component A of the traction fluid of the present invention comprises a diester having two cyclohexyl rings in its molecule.
  • the two ester linkages bring about an interdipolar force between the molecules. It is believed that the interdipolar force serves to bring the fluid into a stable glassy state under high load conditions, thereby increasing the shear strength.
  • the component B in the traction fluid of the present invention has a quaternary carbon atom of the gem-dialkyl type. Therefore when the traction device is under high load conditions the cyclohexyl rings are firmly engaged, like gears, with the gem-dialkyl portions of the quaternary carbon of the component B, while when the device is released from the load this engagement is quickly broken thereby causing fluidization.
  • Diester A of the present invention was synthesized by the following method.
  • cyclohexanol and 104 g of malonic acid i.e., 0.4 mol per mol of cyclohexanol
  • phosphoric acid was added in an amount of 1% by weight based on the total weight of the reactants.
  • the reactor was heated at 180°C.
  • the contents of the reactor were allowed to react at a temperature in the range of 180°C to 210°C under atomospheric pressure.
  • the reaction was stopped at a point when the water generated during the reaction amounted to twice, by mol. of the amount of the malonic acid.
  • reaction mixture was washed with an alkaline solution to remove unreacted compounds from the mixture of the reaction products, i.e., a diester of cyclohexanol with malonic acid, the unreacted cyclohexanol and phosphoric acid, followed by vacuum distillation, thereby isolating a pure diester (A1).
  • an alkaline solution to remove unreacted compounds from the mixture of the reaction products, i.e., a diester of cyclohexanol with malonic acid, the unreacted cyclohexanol and phosphoric acid, followed by vacuum distillation, thereby isolating a pure diester (A1).
  • diesters A2 and A3 of the present invention were synthesized using the following raw materials: A2 ?? ethylene glycol and cyclohexanecarboxylic acid (in excess acid) A3 ?? succinic acid and cyclohexanol
  • the diesters thus produced were each blended with polybutene having an average molecular weight of 900 to 2350 followed by the measurement of traction coefficient.
  • the conditions of the measurement of the traction coefficient were as follows: measuring apparatus: Soda-type four-roller traction testing machine test conditions: a fluid temperature of 20°C; a roller temperature of 30°C; a mean Hertzian pressure of 1.2 GPa; a rolling velocity of 3.6 m/s; and a slipping ratio of 3.0%.
  • the traction fluids of the present invention were found to be remarkably superior in traction performance to the conventional fluids as shown in Table 1.
  • traction coefficients of the following traction fluids were measured under the same conditions as those used in the above examples: a traction fluid consisting of 100% by weight of the component B; traction fluids obtained by blending the component A1 to A3 with 5 to 30% by weight of OCP or PMA; and a commercially available traction fluid (Santotrack ®).
  • OCP is an olefin copolymer. Specifically, an ethylene-propylene copolymer having an average molecular weight of 150,000 to 300,000 was used as OCP.
  • PMA is a polymethyacrylate. Specifically, a polymer having an average molecular weight of 50,000 to 300,000 was used as PMA.
  • Table 1 A Viscosity (cst) Viscosity index Traction coefficient Loadings % M.W.
  • the present invention relates to a traction fluid which comprises a component A comprised of a diester or the like having two cyclohexyl rings and linear-chain hydrocarbons as the skeleton and a specific amount of a component B comprised of a branched poly- ⁇ -olefin, and which exhibits not only an extremely high traction coefficient, but also is inexpensive and exhibits excellent viscosity characteristics.
  • this traction fluid in a power transmission device, particularly a traction drive device, leads to a remarkable increase in shearing force under a high load, and at the same time enables reduction in size of the device and reduced cost of the device.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Abstract

Fluide de traction préparé en formant un composé diester représenté par la formule générale (I) à partir de 0,1 à 95 % en poids d'une poly-alpha-oléfine ramifiée. Dans la formule, A' représente une liaison ester de -COO- ou -OOC-, n est compris entre 1 et 10, les groupes R1 représentent un ou deux membres sélectionnés parmi un atome d'hydrogène et un groupe alkyle possédant de 1 à 8 atomes de carbone, et les groupes R2 représentent un ou deux membres sélectionnés parmi un atome d'hydrogène et un groupe alkyle possédant de 1 à 3 atomes de carbone. Des dérivés de ce composé sont également décrits. Ce fluide est utilisé de préférence dans une unité de transmission de puissance motrice, notamment dans une unité d'entraînement par traction.
EP87904959A 1987-07-30 1987-07-30 Fluide de traction Expired - Lifetime EP0328642B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP1987/000565 WO1989001021A1 (fr) 1987-07-30 1987-07-30 Fluide de traction

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EP0328642A4 EP0328642A4 (fr) 1989-07-25
EP0328642A1 true EP0328642A1 (fr) 1989-08-23
EP0328642B1 EP0328642B1 (fr) 1993-03-10

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EP87904959A Expired - Lifetime EP0328642B1 (fr) 1987-07-30 1987-07-30 Fluide de traction

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EP (1) EP0328642B1 (fr)
JP (1) JPS62177099A (fr)
DE (1) DE3784732D1 (fr)
WO (1) WO1989001021A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6372696B1 (en) 1999-11-09 2002-04-16 The Lubrizol Corporation Traction fluid formulation
US7045488B2 (en) 2002-05-16 2006-05-16 The Lubrizol Corporation Cylic oligomer traction fluid

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8626510D0 (en) * 1986-11-06 1986-12-10 Shell Int Research Ester compounds as lubricants
JPS62177099A (ja) * 1987-07-30 1987-08-03 Toa Nenryo Kogyo Kk トラクシヨン用フル−ド
JPH0747752B2 (ja) * 1989-09-16 1995-05-24 株式会社コスモ総合研究所 トラクションドライブ用流体
JP4521275B2 (ja) * 2002-09-18 2010-08-11 出光興産株式会社 トラクションドライブ用流体組成物

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US3440894A (en) * 1966-10-13 1969-04-29 Monsanto Co Tractants and method of use
JPS53127970A (en) * 1977-04-14 1978-11-08 Nippon Oil & Fats Co Ltd Synthetic lubricating oil compound
JPS5496667A (en) * 1977-12-29 1979-07-31 Bayer Ag Ester carboxylate of pentaerythritol
JPS5968397A (ja) * 1982-10-13 1984-04-18 Cosmo Co Ltd リヤアクスル用ギヤ油組成物
JPS59191797A (ja) * 1983-04-14 1984-10-30 Nippon Petrochem Co Ltd トラクシヨンドライブ用流体
JPS6039715A (ja) * 1983-07-12 1985-03-01 ザ　チェリー　コーポレーション 電気製品用連動スイツチ
JPS6119697A (ja) * 1984-07-06 1986-01-28 Nippon Steel Chem Co Ltd トラクシヨンオイル組成物
JPS62177099A (ja) * 1987-07-30 1987-08-03 Toa Nenryo Kogyo Kk トラクシヨン用フル−ド

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DE2117323C3 (de) * 1971-04-08 1978-08-31 Robert Bosch Gmbh, 7000 Stuttgart Temperaturschalter
JPS619497A (ja) * 1984-06-25 1986-01-17 Nippon Oil Co Ltd 自動変速機油組成物

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US3440894A (en) * 1966-10-13 1969-04-29 Monsanto Co Tractants and method of use
JPS53127970A (en) * 1977-04-14 1978-11-08 Nippon Oil & Fats Co Ltd Synthetic lubricating oil compound
JPS5496667A (en) * 1977-12-29 1979-07-31 Bayer Ag Ester carboxylate of pentaerythritol
JPS5968397A (ja) * 1982-10-13 1984-04-18 Cosmo Co Ltd リヤアクスル用ギヤ油組成物
JPS59191797A (ja) * 1983-04-14 1984-10-30 Nippon Petrochem Co Ltd トラクシヨンドライブ用流体
JPS6039715A (ja) * 1983-07-12 1985-03-01 ザ　チェリー　コーポレーション 電気製品用連動スイツチ
JPS6119697A (ja) * 1984-07-06 1986-01-28 Nippon Steel Chem Co Ltd トラクシヨンオイル組成物
JPS62177099A (ja) * 1987-07-30 1987-08-03 Toa Nenryo Kogyo Kk トラクシヨン用フル−ド

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Title
JAPANESE PATENTS REPORT, vol. 85, no. 37, section CH, October 1985, Derwent Publications Ltd, London, GB; & JP-A-60 039 715 (TOA NENRYO K.K.K.) 07-09-1985 *
PATENT ABSTRACTS OF JAPAN vol. 012, no. 028 (C-471) <2875> 27 January 1988 & JP 62 177099 A (TOA NENRYO K.K.K.) 03 August 1987 *
See also references of WO8901021A1 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6372696B1 (en) 1999-11-09 2002-04-16 The Lubrizol Corporation Traction fluid formulation
US7045488B2 (en) 2002-05-16 2006-05-16 The Lubrizol Corporation Cylic oligomer traction fluid

Also Published As

Publication number Publication date
JPH0588760B2 (fr) 1993-12-24
WO1989001021A1 (fr) 1989-02-09
EP0328642B1 (fr) 1993-03-10
DE3784732T2 (fr) 1993-06-17
JPS62177099A (ja) 1987-08-03
EP0328642A4 (fr) 1989-07-25
DE3784732D1 (de) 1993-04-15

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