JPH0380191B2 - - Google Patents
Info
- Publication number
- JPH0380191B2 JPH0380191B2 JP16506483A JP16506483A JPH0380191B2 JP H0380191 B2 JPH0380191 B2 JP H0380191B2 JP 16506483 A JP16506483 A JP 16506483A JP 16506483 A JP16506483 A JP 16506483A JP H0380191 B2 JPH0380191 B2 JP H0380191B2
- Authority
- JP
- Japan
- Prior art keywords
- viscosity
- traction drive
- traction
- fraction
- methyl
- 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.)
- Expired
Links
- 239000012530 fluid Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WHXXITRYIISMNG-UHFFFAOYSA-N 1-methyl-4-[2-methyl-3-(4-methylcyclohexyl)butan-2-yl]cyclohexane Chemical compound C1CC(C)CCC1C(C)(C)C(C)C1CCC(C)CC1 WHXXITRYIISMNG-UHFFFAOYSA-N 0.000 description 2
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- GHFNRUXLXRHDRQ-UHFFFAOYSA-N (1-cyclohexyl-2-methylpropan-2-yl)cyclohexane Chemical compound C1CCCCC1C(C)(C)CC1CCCCC1 GHFNRUXLXRHDRQ-UHFFFAOYSA-N 0.000 description 1
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 1
- GEPBEZWRRNVONZ-UHFFFAOYSA-N 1-cyclohexyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C1CCCCC1 GEPBEZWRRNVONZ-UHFFFAOYSA-N 0.000 description 1
- YOGPRIRTVSBYDR-UHFFFAOYSA-N 1-ethyl-4-[1-(4-ethylcyclohexyl)-2-methylpropan-2-yl]cyclohexane Chemical compound C1CC(CC)CCC1CC(C)(C)C1CCC(CC)CC1 YOGPRIRTVSBYDR-UHFFFAOYSA-N 0.000 description 1
- WLWCXXTYGZIDDR-UHFFFAOYSA-N 1-methyl-4-[2-(4-methylcyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(C)CCC1C(C)(C)C1CCC(C)CC1 WLWCXXTYGZIDDR-UHFFFAOYSA-N 0.000 description 1
- QQOXVUDLXDCXFI-UHFFFAOYSA-N 1-methyl-4-[2-methyl-1-(4-methylcyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(C)CCC1CC(C)(C)C1CCC(C)CC1 QQOXVUDLXDCXFI-UHFFFAOYSA-N 0.000 description 1
- PZJLQLLYMNKURT-UHFFFAOYSA-N 1-methyl-4-[2-methyl-1-(4-methylphenyl)propan-2-yl]benzene Chemical compound C1=CC(C)=CC=C1CC(C)(C)C1=CC=C(C)C=C1 PZJLQLLYMNKURT-UHFFFAOYSA-N 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
【発明の詳細な説明】
本発明は低粘度でトラクシヨン係数の優れたト
ラクシヨンドライブ用流体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a traction drive fluid with low viscosity and excellent traction coefficient.
トラクシヨンドライブ用の流体はトラクシヨン
ドライブ（ころがり接触による摩擦駆動装置）、
例えば自動車用無段変速機、産業用無段変速機、
水圧機器などに用いられる流体であり、高いトラ
クシヨン係数や熱および酸化に対する安定性、経
済性が要求されている。 The fluid for traction drive is traction drive (friction drive device using rolling contact),
For example, continuously variable transmissions for automobiles, continuously variable transmissions for industrial use,
It is a fluid used in hydraulic equipment, etc., and is required to have a high traction coefficient, stability against heat and oxidation, and economic efficiency.
近年、このようなトラクシヨンドライブ用の流
体を用いるトラクシヨン駆動装置は、小型化かつ
高負荷条件で用いられることが多くなつた。この
ような苛酷な条件下でトラクシヨン駆動装置を使
用する場合は高い温度においても充分な性能を示
すトラクシヨンドライブ用の流体を用いる必要が
ある。これまで種々のトラクシヨンドライブ用流
体が提案されている。例えば、特公昭46−338号
公報、特公昭46−339号公報、特公昭47−35763号
公報、特公昭48−42067号公報、特公昭48−42068
号公報、特公昭53−36105号公報、特開昭55−
43108号公報、特開昭55−40726号公報などに記載
されたものが挙げられる。しかし、これらは粘度
が比較的大きく撹拌ロスによる動力伝達効率が低
下するという問題があつた。 In recent years, traction drive devices that use such fluid for traction drive have become increasingly compact and used under high load conditions. When using a traction drive device under such severe conditions, it is necessary to use a traction drive fluid that exhibits sufficient performance even at high temperatures. Various traction drive fluids have been proposed so far. For example, JP 46-338, JP 46-339, JP 47-35763, JP 48-42067, JP 48-42068.
Publication No. 53-36105, Japanese Patent Application Publication No. 1983-36105
Examples include those described in Publication No. 43108 and Japanese Patent Application Laid-open No. 40726/1983. However, these have a problem in that their viscosity is relatively large and power transmission efficiency is reduced due to stirring loss.
そこで、本発明者らは優れたトラクシヨン係数
を有するとともに、低粘度であるトラクシヨンド
ライブ用の流体を開発すべく鋭意検討を重ねた結
果、特定の化合物をベースストツクとして含有す
るトラクシヨンドライブ用の流体が、目的とする
特性を有していることを見い出し、本発明を完成
した。 Therefore, the inventors of the present invention have conducted intensive studies to develop a fluid for traction drives that has an excellent traction coefficient and a low viscosity. The present invention was completed based on the discovery that the present invention has the desired properties.
すなわち、本発明は、一般式
（式中R1，R2はそれぞれ水素、メチル基ある
いはエチル基を示し、R3は水素またはメチル基
を示す。）
で表わされる化合物をベースストツクとして含有
するトラクシヨンドライブ用流体である。 That is, the present invention provides the general formula (In the formula, R 1 and R 2 each represent hydrogen, a methyl group, or an ethyl group, and R 3 represents hydrogen or a methyl group.) This is a traction drive fluid containing a compound represented by the following as a base stock.
上記一般式（）で表わされる化合物としては
様々なものが考えられるが、具体的には次の如き
ものをあげることができる。すなわち、
式
で表わされる２−メチル−１，２−ジ（シクロヘ
キシル）プロパン、
式
で表わされる２−メチル−１，２−ジ（４−メチ
ルシクロヘキシル）プロパン、
式
で表わされる２−メチル−２，３−ジ（４−メチ
ルシクロヘキシル）ブタン、
式
で表わされる２−メチル−１，２−ジ（４−エチ
ルシクロヘキシル）プロパンなどがある。 Various compounds can be considered as the compound represented by the above general formula (), and specifically, the following can be mentioned. That is, Eq. 2-Methyl-1,2-di(cyclohexyl)propane, represented by the formula 2-Methyl-1,2-di(4-methylcyclohexyl)propane, represented by the formula 2-Methyl-2,3-di(4-methylcyclohexyl)butane, represented by the formula Examples include 2-methyl-1,2-di(4-ethylcyclohexyl)propane represented by:
本発明においてはこれらの化合物を単独あるい
は組合せて、トラクシヨンドライブ用流体のベー
スストツクとすれば良い。このような一般式
（）で表わされる化合物は、各種の方法により
製造することが可能であり、本発明においては特
に制限なく、様々な方法により製造することがで
きる。一般的な製造方法としては、ベンゼン、ト
ルエン、エチルベンゼンなどを塩化アルミニウ
ム、塩化第二鉄、塩化第二スズ、三フツ化ホウ
素、フツ化水素、硫酸などのフリーデルクラフツ
触媒の存在下に−30〜80℃においてメタリルクロ
ライド、プレニルクロライドまたはイソプレンを
反応させた後、水素化する方法をあげることがで
きる。この場合の水素化条件は、原料、触媒の種
類などにより一義的に決めることはできないが、
通常は温度20〜250℃、圧力５〜100気圧の範囲で
選定する。また水素化触媒としては白金、パラジ
ウム、ロジウム、ルテニウム、ニツケルなどを用
いればよい。このようにして得られた一般式
（）で表わされる化合物は、そのままトラクシ
ヨンドライブ用の流体のベースストツクとして用
いることができ、優れたトラクシヨン係数ならび
に酸化安定性を示すものである。また、一般式
（）の化合物は上述の方法等によれば比較的安
価に製造することができ、本発明のトラクシヨン
ドライブ用流体は価格的にも低廉である。さらに
低粘度であるため、撹拌ロスによる動力伝達効率
の低下等は生じず、他の高粘度トラクシヨンドラ
イブ用流体に対する希釈剤としても適用できる。 In the present invention, these compounds may be used alone or in combination as the base stock of the traction drive fluid. The compound represented by the general formula () can be produced by various methods, and the present invention is not particularly limited and can be produced by various methods. A typical production method involves converting benzene, toluene, ethylbenzene, etc. into -30 A method can be mentioned in which methallyl chloride, prenyl chloride or isoprene is reacted at ~80°C and then hydrogenated. The hydrogenation conditions in this case cannot be determined unambiguously depending on the raw materials, the type of catalyst, etc.
Usually, the temperature is selected in the range of 20 to 250°C and the pressure is in the range of 5 to 100 atmospheres. Further, platinum, palladium, rhodium, ruthenium, nickel, etc. may be used as the hydrogenation catalyst. The compound represented by the general formula () thus obtained can be used as it is as a base stock for a traction drive fluid, and exhibits an excellent traction coefficient and oxidation stability. Further, the compound of general formula () can be produced relatively inexpensively by the above-mentioned method, and the traction drive fluid of the present invention is also inexpensive. Furthermore, since it has a low viscosity, there is no reduction in power transmission efficiency due to stirring loss, and it can also be used as a diluent for other high-viscosity traction drive fluids.
以上の如く、本発明のトラクシヨンドライブ用
流体は、優れたトラクシヨン係数を示すものとし
て、自動車の無段変速機、水圧機器などの様々な
機械製品に幅広く利用される。 As described above, the traction drive fluid of the present invention exhibits an excellent traction coefficient and is widely used in various mechanical products such as continuously variable transmissions of automobiles and hydraulic equipment.
次に本発明の実施例を示す。 Next, examples of the present invention will be shown.
実施例 １
内容積３のフラスコにトルエン1564gと無水
塩化アルミニウム40gを入れて室温において、撹
拌しながらメタリルクロライド272gとトルエン
92gとの混合物を５時間にわたり徐徐に滴下した
後、さらに１時間撹拌して反応を行なつた。つい
で、これに水500mlを加えて塩化アルミニウムを
分解し、油層を分離したのち、油層を１規定水酸
化ナトリウム水溶液１と飽和食塩水１でそれ
ぞれ３回洗浄し、無水硫酸ナトリウムで乾燥し
た。次に、蒸留により未反応のトルエンを除去し
た後、減圧蒸留して沸点範囲106〜113℃（0.16mm
Hg）の留分500gを得た。この留分の主成分は、
２−メチル−１，２−ジ（ｐ−トリル）プロパン
であつた。Example 1 Put 1564 g of toluene and 40 g of anhydrous aluminum chloride into a flask with an internal volume of 3, and add 272 g of methallyl chloride and toluene while stirring at room temperature.
92 g of the mixture was gradually added dropwise over 5 hours, and the mixture was further stirred for 1 hour to carry out the reaction. Next, 500 ml of water was added to decompose the aluminum chloride, and the oil layer was separated. The oil layer was washed three times each with one part of a 1N aqueous sodium hydroxide solution and one part of saturated brine, and dried over anhydrous sodium sulfate. Next, unreacted toluene is removed by distillation, and then distilled under reduced pressure with a boiling point range of 106-113℃ (0.16mm
500 g of a fraction of Hg) was obtained. The main component of this fraction is
It was 2-methyl-1,2-di(p-tolyl)propane.
ついで、この留分500gを１のオートクレー
ブに入れてニツケル触媒（日揮化学社製：Ｎ−
113）50gを添加し、水素圧50Kg／cm2Ｇ、温度200
℃において３時間水素化を行なつた。反応生成物
から軽質分を除去し、分析した結果、水素化率
99.9％以上あり、主成分は２−メチル−１，２−
ジ（４−メチルシクロヘキシル）プロパンである
ことが確認された。このものの比重は0.88（15／
４℃）でああり、動粘度10.7cst（40℃）、2.41cst
（100℃）、粘度指数６、粘度20cstにおけるトラク
シヨン係数は0.087であつた。 Next, 500 g of this fraction was placed in an autoclave No. 1, and a nickel catalyst (manufactured by JGC Chemical Co., Ltd.: N-
113) Add 50g, hydrogen pressure 50Kg/cm 2 G, temperature 200
Hydrogenation was carried out for 3 hours at °C. As a result of removing light components from the reaction product and analyzing it, the hydrogenation rate was
99.9% or more, the main component is 2-methyl-1,2-
It was confirmed to be di(4-methylcyclohexyl)propane. The specific gravity of this material is 0.88 (15/
4℃), kinematic viscosity 10.7cst (40℃), 2.41cst
(100°C), viscosity index 6, and viscosity 20cst, the traction coefficient was 0.087.
なお、トラクシヨン係数の測定は２円筒型摩擦
試験機にて行なつた。すなわち、１線で接する同
じサイズの円筒（直径60mm、厚さ６mm）の片方を
一定速度（2000r.p.m.）で、もう一方の円筒をそ
れより遅い一定速度（1700r.p.m.）で回転させ、
両円筒の接触部分にバネにより140Kgの荷重を与
え、歪ゲージとトルクメーターにてトルクを測定
し、トラクシヨン係数を求めた。この円筒は炭素
鋼SCM−３で出来ており、表面はアルミナ
（0.03μ）によりパフ仕上げがされており、表面あ
らさはRmax＝0.2μであり、またヘルツ接触圧は
75Kg／mm2であつた。試験に供した油は温度調節に
より20cstにした。 The traction coefficient was measured using a two-cylinder friction tester. In other words, one cylinder of the same size (diameter 60 mm, thickness 6 mm) that is in contact with a line is rotated at a constant speed (2000 r.pm), and the other cylinder is rotated at a slower constant speed (1700 r. pm).
A load of 140 kg was applied by a spring to the contact area between both cylinders, and the torque was measured using a strain gauge and a torque meter to determine the traction coefficient. This cylinder is made of carbon steel SCM-3, the surface is puffed with alumina (0.03μ), the surface roughness is Rmax = 0.2μ, and the Hertzian contact pressure is
It was 75Kg/ mm2 . The temperature of the oil used in the test was adjusted to 20 cst.
実施例 ２
内容積５のフラスコにトルエン3500gと濃硫
酸300gを入れ０℃において撹拌しながらさらに
イソプレン450gとトルエン200gとの混合物を８
時間にわたり徐々に滴下したのち、さらに１時間
０℃で撹拌した。次いで油層を分離してこの油層
を１規定の水酸化ナトリウム水溶液１と飽和食
塩水１でそれぞれ３回洗浄し、無水硫酸ナトリ
ウムで乾燥させた。次に蒸留により未反応のトル
エンを除いた後、減圧蒸留して軽質分を除去し
た。得られた生成物500gを１のオートクレー
ブに入れ、ニツケル触媒（日揮化学社製：Ｎ−
113）50gを添加し、水素圧50Kg／cm2Ｇ、温度200
℃で３時間水素化した。反応生成物は軽質分を除
去し、得られた生成油を分析した結果、水素化率
99.9％以上であり、主成分は２−メチル−２，３
−ジ（４−メチルシクロヘキシル）ブタンである
ことが確認された。このものの比重は0.89（15／
４℃）であり、動粘度26.8cst（40）、3.8cst（100
℃）、粘度指数−78、粘度20cstにおけるトラクシ
ヨン係数は0.088であつた。Example 2 3500 g of toluene and 300 g of concentrated sulfuric acid were put into a flask with an internal volume of 5, and while stirring at 0°C, a mixture of 450 g of isoprene and 200 g of toluene was added to 8
After the mixture was gradually added dropwise over a period of time, the mixture was further stirred at 0° C. for 1 hour. The oil layer was then separated, washed three times each with 1 part of 1N aqueous sodium hydroxide solution and 1 part of saturated brine, and dried over anhydrous sodium sulfate. Next, unreacted toluene was removed by distillation, and then light components were removed by distillation under reduced pressure. 500g of the obtained product was placed in an autoclave No. 1, and a nickel catalyst (manufactured by JGC Chemical Co., Ltd.: N-
113) Add 50g, hydrogen pressure 50Kg/cm 2 G, temperature 200
Hydrogenation was carried out at ℃ for 3 hours. The light components of the reaction product were removed, and the resultant product oil was analyzed and the hydrogenation rate was determined.
99.9% or more, the main component is 2-methyl-2,3
-Di(4-methylcyclohexyl)butane was confirmed. The specific gravity of this material is 0.89 (15/
4℃), kinematic viscosity 26.8 cst (40), 3.8 cst (100
The traction coefficient was 0.088 at a viscosity index of -78 and a viscosity of 20 cst.
比較例 １
３のガラス製フラスコにｐ−メチルスチレン
1200mlおよび55％硫酸300mlを入れ、撹拌しなが
ら110℃で２時間反応させた。撹拌終了後、静置
し、水層と油層とを分離して、油層を３％水酸化
ナトリウム水溶液１と飽和食塩水１でそれぞ
れ３回洗滌後、無水硫酸ナトリウムで乾燥させ
た。未反応のｐ−メチルスチレンを留去後蒸留
し、沸点144〜153℃／0.2mmHg留分600gを得た。
この留分は分析の結果ｐ−メチルスチレンの線状
二量体98％と環状二量体２％の混合物であること
が確認された。Comparative Example 1 P-methylstyrene was added to the glass flask of 3.
1200 ml and 300 ml of 55% sulfuric acid were added, and the mixture was reacted at 110°C for 2 hours with stirring. After stirring, the mixture was allowed to stand, separated into an aqueous layer and an oil layer, and the oil layer was washed three times each with 1 part of a 3% aqueous sodium hydroxide solution and 1 part of a saturated saline solution, and then dried over anhydrous sodium sulfate. After unreacted p-methylstyrene was distilled off, 600 g of a fraction with a boiling point of 144-153°C/0.2 mmHg was obtained.
Analysis of this fraction confirmed that it was a mixture of 98% linear dimer and 2% cyclic dimer of p-methylstyrene.
この留分を実施例１と同様に水添し後処理する
ことにより、ｐ−メチルスチレンの線状二量体水
添物を主成分とするトラクシヨンドライブ用流体
を得た。 This fraction was hydrogenated and post-treated in the same manner as in Example 1 to obtain a traction drive fluid containing a hydrogenated linear dimer of p-methylstyrene as a main component.
この水添して得られた化合物の性状は比重
（15／４℃）0.88、動粘度11.4cst（40℃）、2.6cst
（100℃）、粘度指数26、粘度20cstにおけるトラク
シヨン係数は、0.077であり、本発明のものより
トラクシヨン係数が劣ることがわかつた。 The properties of the compound obtained by hydrogenation are: specific gravity (15/4℃) 0.88, kinematic viscosity 11.4cst (40℃), 2.6cst
(100°C), a viscosity index of 26, and a viscosity of 20 cst, the traction coefficient was 0.077, which was found to be inferior to that of the present invention.
比較例 ２
３のガラス製フラスコにフエニルシクロヘキ
サン800g、ｎ−ヘキサン200gおよび濃硫酸300g
を入れ、０℃に冷却した。反応温度を０℃に保ち
撹拌しながらスチレン260gを３時間かけて滴下
し、更に１時間撹拌して反応を行なつた。撹拌停
止後静置し、硫酸層と油層とを分離して、油層を
３％水酸化ナトリウム水溶液１と飽和食塩水１
とでそれぞれ３回洗浄後、無水硫酸ナトリウム
で乾燥させた。溶媒ｎ−ヘキサンと未反応のフエ
ニルシクロヘキサンを留去した後蒸留し、沸点
130〜143℃／0.15mmHg留分520gを得た。Comparative Example 2 800 g of phenylcyclohexane, 200 g of n-hexane, and 300 g of concentrated sulfuric acid were placed in the glass flask of 3.
was added and cooled to 0°C. While stirring the reaction temperature at 0° C., 260 g of styrene was added dropwise over 3 hours, and the reaction was further stirred for 1 hour. After stopping the stirring, leave it to stand, separate the sulfuric acid layer and the oil layer, and add the oil layer to 1 part of 3% sodium hydroxide aqueous solution and 1 part of saturated brine.
After washing three times with and drying with anhydrous sodium sulfate. After distilling off the solvent n-hexane and unreacted phenylcyclohexane, the boiling point
520g of a 130-143°C/0.15mmHg fraction was obtained.
この留分は分析の結果、１−フエニル−１−
（シクロヘキシルフエニル）エタンであることが
確認された。 As a result of analysis, this fraction was found to be 1-phenyl-1-
It was confirmed to be (cyclohexyl phenyl) ethane.
この留分を実施例１と同様に水素化し後処理す
ることにより、１−シクロヘキシル−１−（ジシ
クロヘキシル）エタンを得た。 This fraction was hydrogenated and post-treated in the same manner as in Example 1 to obtain 1-cyclohexyl-1-(dicyclohexyl)ethane.
この化合物の性状は比重（15／４℃）0.93、動
粘度68.0cst（40℃）、6.57cst（100℃）、粘度指数−
６、粘度20cstにおけるトラクシヨン係数は0.084
であつた。これは本発明のものに較べ粘度が大き
いことがわかつた。 The properties of this compound are specific gravity (15/4℃) 0.93, kinematic viscosity 68.0cst (40℃), 6.57cst (100℃), viscosity index -
6. Traction coefficient at viscosity 20cst is 0.084
It was hot. It was found that this had a higher viscosity than that of the present invention.
Claims (1)
いはエチル基を示し、R3は水素またはメチル基
を示す。） で表わされる化合物をベースストツクとして含有
するトラクシヨンドライブ用流体。[Claims] 1. General formula (In the formula, R 1 and R 2 each represent hydrogen, a metal group, or an ethyl group, and R 3 represents hydrogen or a methyl group.) A traction drive fluid containing a compound represented by the following as a base stock.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16506483A JPS6058495A (en) | 1983-09-09 | 1983-09-09 | Fluid for traction drive |
| US06/647,110 US4556503A (en) | 1983-09-09 | 1984-09-04 | Traction drive fluids |
| EP84110655A EP0135871B1 (en) | 1983-09-09 | 1984-09-07 | Traction drive fluids |
| DE8484110655T DE3480851D1 (en) | 1983-09-09 | 1984-09-07 | POWER TRANSFER LIQUIDS. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16506483A JPS6058495A (en) | 1983-09-09 | 1983-09-09 | Fluid for traction drive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6058495A JPS6058495A (en) | 1985-04-04 |
| JPH0380191B2 true JPH0380191B2 (en) | 1991-12-24 |
Family
ID=15805169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16506483A Granted JPS6058495A (en) | 1983-09-09 | 1983-09-09 | Fluid for traction drive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6058495A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009119831A1 (en) | 2008-03-28 | 2009-10-01 | 富士フイルム株式会社 | Composition and method for forming coating film |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH066711B2 (en) * | 1986-01-23 | 1994-01-26 | 出光興産株式会社 | Fluid for Traction Drive |
| JP2577399B2 (en) * | 1987-09-17 | 1997-01-29 | 出光興産株式会社 | Method for producing traction drive fluid |
-
1983
- 1983-09-09 JP JP16506483A patent/JPS6058495A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009119831A1 (en) | 2008-03-28 | 2009-10-01 | 富士フイルム株式会社 | Composition and method for forming coating film |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6058495A (en) | 1985-04-04 |
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