EP0082967A2 - Traction fluid - Google Patents

Traction fluid Download PDF

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Publication number
EP0082967A2
EP0082967A2 EP82111051A EP82111051A EP0082967A2 EP 0082967 A2 EP0082967 A2 EP 0082967A2 EP 82111051 A EP82111051 A EP 82111051A EP 82111051 A EP82111051 A EP 82111051A EP 0082967 A2 EP0082967 A2 EP 0082967A2
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EP
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Prior art keywords
alkyl
use according
bicyclo
cycloalkyl
heptane
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EP82111051A
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German (de)
French (fr)
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EP0082967A3 (en
EP0082967B1 (en
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Herbert Vojacek
Norbert Dr. Matzat
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Optimol-Olwerke GmbH
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Optimol-Olwerke GmbH
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Priority to AT82111051T priority Critical patent/ATE29901T1/en
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/002—Traction fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M109/00—Lubricating compositions characterised by the base-material being a compound of unknown or incompletely defined constitution

Definitions

  • the invention relates to the use of organic compounds as liquids for transmitting frictional forces, in particular in friction wheel transmissions.
  • Friction gear or traction gear are devices in which a torque is transmitted by nominal point or line guidance.
  • a friction wheel transmission consists of two rollers with parallel or intersecting axes which are in tangential contact with one another, one roller being the drive element and the other being the output element.
  • the transmissible torque of such a friction or traction transmission is a direct function of the surface pressure between the rollers and the coefficient of friction of the frictional contact between the roller surfaces.
  • special advantages of traction gearboxes are the possibility of continuously changing the gear ratio under full load, without having to interrupt the load while changing the gear ratio, and its high efficiency in the entire gear ratio range.
  • a disadvantage of the friction wheel gears is still the much larger dimensions compared to gear gears with the same transferable performance and the same service life. Since the transferable power depends linearly on the circumferential speed of the friction discs at the radius of the friction contact, on the normal force that can be transmitted in the friction contact and on the friction coefficient of the friction contact that can be used for power transmission, all three influencing variables must be chosen as high as possible for the construction of a friction gear.
  • the transferable normal force is given by the permissible Hertzian pressure. This determines the service life of the gear unit.
  • the circumferential speed is restricted by the size.
  • the coefficient of friction that can be used in the transmission is essentially determined by the slip, the peripheral speed of the drive body and the contact pressure between the drive and driven bodies.
  • the coefficient of friction is defined as the quotient of the frictional force generated during the friction and the contact pressure between the drive and driven bodies.
  • the slip is defined as the absolute value of the quotient from the difference between the two peripheral speeds of the rolling elements and the larger peripheral speed.
  • the aim is for the coefficient of friction to increase rapidly with increasing slip in the area of a small slip. This achieves a good efficiency of the traction transmission.
  • the aim is for the maximum coefficient of friction to be as large as possible in order to achieve maximum utilization of the power transmission (cf. e.g. D.E.G. Tucker, ant. "Antriebstechnik" 17, No. 6, June 1978).
  • the coefficient of friction is determined by the chemical structure of the traction fluid and the operating parameters of the friction gear. These include rolling and sliding speed, normal force in friction contact, macro and micro geometry of the roller surface and thus the geometric shape of the friction contact, temperature in friction contact, drilling friction and skew.
  • DE-AS 1 644 925 and DE-AS 1 644 926 describe a large number of organic compounds.
  • suitable compounds with a high coefficient of friction for. B. decalin, 1,2-hydrindane, perhydrophenanthrene, perhydrofluorene, perhydrofluoranthene, perhydroazonaphthene, cyclohexyldecalin, primary perhydrocyclopentadiene and methylene hydrophenanthrene.
  • a high coefficient of friction of the traction fluid is also associated with high wear of the traction gear.
  • the so-called load-bearing capacity of the liquid film is as high as possible. This ensures that there is a certain lubricating effect even in the event of an emergency.
  • the object of the invention is therefore to provide traction fluids which have a high coefficient of friction in conjunction with a high load-bearing capacity. This object is achieved with the present invention.
  • the invention relates to the use of compounds having one or more cyclohexane and / or cycloheptane rings bridged by one or two alkylene chains which have one or two carbon atoms and which are substituted by one or more substituents from the
  • the group alkyl, alkylidene, alkoxy, alkanoyl, alkylcarbonyloxy, alkoxycarbonyl, oxoalkyl, mercapto, alkylmerkapto, alkanoylmerkapto, halogen and hydroxyl is substituted and in which the alkyl and alkylidene radicals have 1 to 7 carbon atoms and in which alkyl in the 0-containing substituents also mean cycloalkyl can, and two alkyl groups bonded to the same or different ring carbon atoms together can also form an alkylene group, and the ring system, the alkyl, cycloalkyl and / or alkylene groups can also contain one or more double bonds, and
  • the cyclohexane or cycloheptane ring system bridged by two or preferably an alkyl group having 1 or 2 carbon atoms is preferably a cyclohexane ring bridged by methylene or ethylene, such as, for example, B. bicyclo [2.2.2] octane, and in particular bicyclo / 3.2.1 / octane, bicyclo [3.1.1] heptane, bicyclo [2.2.1] heptane or tricyclo [5.2.1.0 2.6 ] decane.
  • the ring system can also contain one or more, preferably a double bond, and is then z.
  • B. Bicyclo [2.2.1] hept-5-ene is preferably a double bond, and is then z.
  • An alkyl group with 1 to 7 carbon atoms can be straight-chain or branched and is e.g. Example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, heptyl, isoheptyl, 2,3,3-trimethyl-butyl, etc.
  • An alkylidene group is derived from one of the alkyl groups mentioned having 1 to 7 carbon atoms, in particular from one of the preferred alkyl groups mentioned, and is z.
  • An alkylene group formed from two alkyl substituents preferably has 2 to 5 carbon atoms and is e.g. B. an ethylene, propylene, butylene or pentylene group.
  • a bridged ring system substituted with such an alkylene group is e.g. B. cyclopropane ⁇ 1-spiro-2> norbornane or decahydro-1,4-methano-azulene.
  • a cycloalkyl group is one with 3 to 7, preferably 5 to 7 carbon atoms and is e.g. Cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, and especially cyclohexyl.
  • a cycloalkyl-alkyl group is one which is composed of the cycloalkyl and alkyl radicals mentioned, in particular of the preferred ones.
  • An alkyl or cycloalkyl group can also one or more, e.g. B. contain two, and in particular a double bond.
  • alkoxy, alkanoyl, alkylcarbonyloxy and an alkoxycarbonyl group are derived from the alkyl and cycloalkyl radicals mentioned, in particular the preferably mentioned.
  • You are e.g. B. methoxy, ethoxy, cyclohexyloxy, acetyl, propionyl, hexylcarbonyl, acetoxy, propionyloxy, hexylcarbonyloxy, ethoxycarbonyl, hexyloxycarbonyl, 1- or 2-cyclohexylpropyl- (2) -oxy etc.
  • An oxoalkyl group is an alkyl group which is substituted by one or more, in particular one or two, oxo groups and which is derived from one of the alkyl radicals mentioned or also cycloalkyl radicals. It is e.g. B. 2-oxo-ethyl, 2- or 3-oxo-propyl, mono- or dioxo-butyl, pentyl or hexyl, such as. B. 1,4-dioxopentyl, 2,5-dioxo-hexyl, oxocyclohexyl, and especially formyl.
  • Halogen as a substituent preferably means fluorine and in particular chlorine.
  • the compounds according to the invention contain one or more identical or different, preferably two and in particular one bridged, cyclohexane and / or cycloheptane ring.
  • a radical which connects these rings is one which is derived from the substituents mentioned, which in this case are therefore common substituents of the ring systems to be connected.
  • Such sub stituents are e.g. B. derived from the alkyl or cycloalkyl substituents alkylene or cycloalkylene groups, such as. B.
  • cyclohexylene (1,4) or an alkylene-cycloalkylene group, derived from the alkoxy or alkoxycarbonyl groups, alkyleneoxy or alkyleneoxycarbonyl groups -alkylene-0 or -alkylene-0-C (0) -, from the alkanoyl groups derived alkylene-carbonyloxy group-alkylene-C (0) -0-, an oxycarbonyl group-OC (O) -, carbonyloxyalkyleneoxcarbonyl group-C (0) -O-alkylene-OC (O) -, alkyleneoxycarbonylalkylene group-alkylene-OC (O) - alkylene, etc.
  • the bridged ring systems and / or the alkyl and alkylene groups of the substituents of the bridged ring systems can be substituted by one or more, preferably 1 to 5, and in particular one or two of the radicals mentioned therefor, which may be the same or different.
  • Typical substituents or compound substituents of the ring systems are e.g. B.
  • tricyclo [5.2.1.0 2,6 ] decanes are also preferred which are substituted by 1 to 5, preferably 1 to 3, substituents from the group consisting of alkyl, hydroxy, mercapto, alkoxy, alkylmercapto, alkanoyloxy and alkanoylmercapto and in which one Alkyl group (or alkanoyl group) has 1 to 7 carbon atoms and can optionally be substituted by one or more, in particular one or two, hydroxyl groups, mercapto groups and / or halogen, in particular bromine or chlorine.
  • TDC tricyclo [5.2.1.o 2.6 ] decane
  • B 2-hydroxymethyl-6,6-dimethyl-bicyclo [3.1.1] heptane, 2-hydroxymethyl-3,3-dimethyl-bicyclo [2.2.1] heptane, 3-acetoxy-2,6,6-trimethyl -bicyclo [3.1.1] heptane, 2-acetoxymethyl-6,6-dimethyl-bicyclo [3.1.1] heptane, 2- (2-hydroxyethyl) -3,3-dimethyl-bicyclo [2.2.1] heptane, 2 -Methylidene-3-acetoxy-6,6-dimethyl-bicyclo [3.1.1] heptane, 4,8,8-trimethyl-9-acetoxymethyl-decahydro-1,4-methano-azulene, 4,8,8-trimethyl -9-
  • the compounds used according to the invention are known or can be prepared by methods known per se in analogy to the known compounds or from the known compounds, e.g. B. by esterification, saponification, etherification, halogenation, etc.
  • the compounds of the invention are ideal as power transmission fluids for traction gearboxes, such as. B. in belt drives or roller drives. They are characterized by a particularly favorable combination of traction properties (high coefficients of friction in the range from approximately 0.05 to approximately 0.11, sharp increase in the coefficient of friction in the range of slip up to 1%) and emergency running properties (high load-bearing capacity of the liquid film).
  • the compounds according to the invention can be used alone or in a mixture with other compounds according to the invention, but also in a mixture with other known traction liquids.
  • Other traction fluids are, for example, fully or partially hydrogenated cyclopentylbiphenylenes and naphthalenes with one or two cyclopentyl groups.
  • they can also contain conventional additives in the usual amounts, such as. B. antioxidants, rust inhibitors, density swellers, antifoams, dispersants, dyes, viscosity index improvers, extreme pressure additives, antiwear additives and / or lubricants.
  • these mixtures generally contain the compounds according to the invention in an amount of at least 5% by weight, in particular at least 30% by weight.
  • the content depends in particular on the type and properties of the other traction fluids.
  • the washers are made of a material that is described as 100 Cr 6 in accordance with DIN 17006.
  • the discs have a diameter of 80 mm.
  • the arithmetic mean roughness R a (Center Line Average CLA) of the drive and driven pulley is in the range from 0.03 to 0.12 ⁇ m.
  • the liquid to be tested is injected between the two disks at an injection temperature of 50 ° C.
  • the following traction fluid was used: 4,8,8-trimethyl-9-formyl-decahydro-1,4-methano-azulene (boiling point 116 to 120 ° C at 0.7 mbar) (Fig. 1 to 5), 2.2 -Dichloro-cyclopropane ⁇ 1-spiro-2> -3,3-dimethyl-norbornane (boiling point 120 ° C at 18 mbar) (Fig. 6 to 10), 3-hydroxy-2,6,6-trimethyl-bicyclo [3.1.1] heptane (boiling point 94 ° C. at 13 mbar) (FIGS.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Lubricants (AREA)
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Abstract

1. Use of bicycloheptane compounds with a cyclohexane ring bridged by a methylene group, whereby the ring system is substituted by one or more substituents from the group cycloalkoxy, cycloalkanoyl, cycloalkylcarbonyloxy, cycloalkoxycarbonyl, oxocycloalkyl, whereby the cycloalkyl radicals possess 3 to 7 carbon atoms and the ring system, the cycloalkyl groups can contain one and also more double bonds and wherein the cycloalkyl groups can be substituted by one or more radicals from the group alkyl, cycloalkyl, hydroxyl, halogen, alkoxy, cycloalkoxy, alkanoyl, alkylcarbonyloxy, alkoxyoxycarbonyl, mercapto, cycloalkyloxycarbonyl and cyano in which an alkyl or cycloalkyl group possesses 1 to 7 carbon atoms and together can also represent cycloalkylalkyl and can contain one or more double bonds, and/or which are bound with a further bridged cyclohexane compound via an alkyl, alkylidene, alkoxy, alkanoyl, alkylcarbonyloxy, alkoxycarbonyl, oxoalkyl, mercapto, alkylmercapto, alkanoylmercapto group, wherein the alkyl and alkylidene radicals possess 1 to 7 carbon atoms and wherein alkyl in the O-containing substituents can also signify cycloalkyl and the ring system, the alkyl, cycloalkyl and/or alkylene groups can also contain one or more double bonds and wherein the alkyl and/or alkylene groups of the said substituents can be substituted by one or more radicals from the group alkyl, cycloalkyl, hydroxyl, halogen, alkoxy, cycloalkoxy, alkanoyl, alkylcarbonyloxy, alkoxyoxycarbonyl, mercapto, cycloalkyloxycarbonyl and cyano, in which an alkyl or cycloalkyl group possesses 1 to 7 carbon atoms and together also represent cycloalkylalkyl and can contain one or more double bonds, as traction fluid in friction drives.

Description

Die Erfindung betrifft die Verwendung von organischen Verbindungen als Flüssigkeiten zur Reibkraftübertragung, insbesondere in Reibradgetrieben.The invention relates to the use of organic compounds as liquids for transmitting frictional forces, in particular in friction wheel transmissions.

Reibrad- oder Traktionsgetriebe sind Vorrichtungen, in welchen ein Drehmoment durch nominale Punkt- oder Linienführung übertragen wird. In vereinfachter Form besteht ein solches Reibradgetriebe aus zwei Walzen mit parallelen oder sich schneidenden Achsen, die in tangentialer Berührung miteinander stehen, wobei eine Walze das Antriebsglied, und die andere das Abtriebsglied darstellt. Das übertragbare Drehmoment eines derartigen Reib- oder Traktionsgetriebes ist eine direkte Funktion der Flächenpressung zwischen den Walzen und Reibungszahl des Reibkontakts zwischen den Walzenoberflächen. Besondere Vorteile von Traktionsgetrieben sind neben einem schwingungsarmen Lauf die Möglichkeit der stufenlosen Veränderbarkeit des Übersetzungsverhältnisses unter voller Last, ohne daß die Belastung während des Änderns der Übersetzung unterbrochen werden muß, sowie ihr hoher Wirkungsgrad im gesamten Übersetzungsbereich.Friction gear or traction gear are devices in which a torque is transmitted by nominal point or line guidance. In a simplified form, such a friction wheel transmission consists of two rollers with parallel or intersecting axes which are in tangential contact with one another, one roller being the drive element and the other being the output element. The transmissible torque of such a friction or traction transmission is a direct function of the surface pressure between the rollers and the coefficient of friction of the frictional contact between the roller surfaces. In addition to a low-vibration run, special advantages of traction gearboxes are the possibility of continuously changing the gear ratio under full load, without having to interrupt the load while changing the gear ratio, and its high efficiency in the entire gear ratio range.

Ein Nachteil der Reibradgetriebe besteht immer noch in den wesentlich größeren Abmessungen gegenüber Zahnradgetrieben bei gleicher übertragbarer Leistung und gleicher Lebensdauer. Da die übertragbare Leistung von der Umfangsgeschwindigkeit der Reibscheiben am Radius des Reibkontakts, von der im Reibkontakt übertragbaren Normalkraft und von der zur Kraftübertragung ausnutzbaren Reibungszahl des Reibkontakts linear abhängt, müssen alle drei Einflußgrößen so hoch wie möglich für die Konstruktion eines Reibradgetriebes gewählt werden. Die übertragbare Normalkraft ist durch die zulässige Hertzsche Pressung gegeben. Diese bestimmt die Lebensdauer des Getriebes. Die Umfangsgeschwindigkeit wird durch die Baugröße eingeengt. Die im Getriebe ausnutzbare Reibungszahl wird im wesentlichen durch den Schlupf, durch die Umfangsgeschwindigkeit des Antriebskörpers und der Anpreßkraft zwischen dem Antriebs- und Abtriebskörper bestimmt.A disadvantage of the friction wheel gears is still the much larger dimensions compared to gear gears with the same transferable performance and the same service life. Since the transferable power depends linearly on the circumferential speed of the friction discs at the radius of the friction contact, on the normal force that can be transmitted in the friction contact and on the friction coefficient of the friction contact that can be used for power transmission, all three influencing variables must be chosen as high as possible for the construction of a friction gear. The transferable normal force is given by the permissible Hertzian pressure. This determines the service life of the gear unit. The circumferential speed is restricted by the size. The coefficient of friction that can be used in the transmission is essentially determined by the slip, the peripheral speed of the drive body and the contact pressure between the drive and driven bodies.

Die Reibungszahl ist definiert als Quotient aus der bei der Reibung entstehenden Reibkraft und der Anpreßkraft zwischen dem Antriebs- und Abtriebskörper. Der Schlupf ist definiert als der absolute Wert des Quotienten aus der Differenz der beiden Umfangsgeschwindigkeiten der Wälzkörper und der größeren Umfangsgeschwindigkeit.The coefficient of friction is defined as the quotient of the frictional force generated during the friction and the contact pressure between the drive and driven bodies. The slip is defined as the absolute value of the quotient from the difference between the two peripheral speeds of the rolling elements and the larger peripheral speed.

Bei Traktionsgetrieben wird angestrebt, daß in dem Bereich eines kleinen Schlupfs die Reibungszahl mit zunehmendem Schlupf rasch ansteigt. Hierdurch erzielt man einen guten Wirkungsgrad des Traktionsgetriebes. Außerdem wird angestrebt, daß die maximale Reibungszahl möglichst groß ist, um eine maximale Ausnutzung der Kraftübertragung zu erreichen (vgl. z. B. D.E.G. Tucker, ant. "Antriebstechnik" 17, Nr. 6, Juni 1978).In the case of traction gears, the aim is for the coefficient of friction to increase rapidly with increasing slip in the area of a small slip. This achieves a good efficiency of the traction transmission. In addition, the aim is for the maximum coefficient of friction to be as large as possible in order to achieve maximum utilization of the power transmission (cf. e.g. D.E.G. Tucker, ant. "Antriebstechnik" 17, No. 6, June 1978).

Die Reibungszahl wird durch die chemische Struktur der Traktionsflüssigkeit und den Betriebsparametern des Reibradgetriebes bestimmt. Dazu zählen Roll- und Gleitgeschwindigkeit, Normalkraft im Reibkontakt, Makro- und Mikrogeometrie der Rollenoberfläche und damit geometrische Gestalt des Reibkontakts, Temperatur im Reibkontakt, Bohrreibung und Schräglauf.The coefficient of friction is determined by the chemical structure of the traction fluid and the operating parameters of the friction gear. These include rolling and sliding speed, normal force in friction contact, macro and micro geometry of the roller surface and thus the geometric shape of the friction contact, temperature in friction contact, drilling friction and skew.

Zur Erhöhung des zu übertragenden Drehmoments ist von diesen Faktoren die Art und Zusammensetzung der Flüssigkeit am leichtesten veränderbar. Es hat deshalb nicht an Versuchen zur Auffindung von Verbindungen zur Verbesserung des Traktionskoeffizienten gefehlt. Die DE-AS 1 644 925 und DE-AS 1 644 926 beschreiben zu diesem Zweck eine Vielzahl von organischen Verbindungen. Als besonders geeignete Verbindungen mit hoher Reibungszahl werden z. B. Decalin, 1,2-Hydrindan, Perhydrophenanthren, Perhydrofluoren, Perhydrofluoranthen, Perhydroazonaphthen, Cyclohexyldecalin, primäres Perhydrocyclopentadien und Methylenhydrophenanthren genannt.Of these factors, the easiest way to change the type and composition of the liquid is to increase the torque to be transmitted. There has been no shortage of attempts to find connections to improve the traction coefficient. For this purpose, DE-AS 1 644 925 and DE-AS 1 644 926 describe a large number of organic compounds. As particularly suitable compounds with a high coefficient of friction, for. B. decalin, 1,2-hydrindane, perhydrophenanthrene, perhydrofluorene, perhydrofluoranthene, perhydroazonaphthene, cyclohexyldecalin, primary perhydrocyclopentadiene and methylene hydrophenanthrene.

Mit einer hohen Reibungszahl der Traktionsflüssigkeit ist aber auch ein hoher Verschleiß des Traktionsgetriebes verbunden. Um den Verschleiß auch bei hoher Reibungszahl möglichst gering zu halten, ist es erforderlich, daß auch die sogenannte Tragfähigkeit des Flüssigkeitsfilms möglichst hoch ist. Dadurch wird erreicht, daß auch im Notlauffall eine gewisse Schmierwirkung vorliegt.A high coefficient of friction of the traction fluid is also associated with high wear of the traction gear. In order to keep the wear as low as possible even with a high coefficient of friction, it is necessary that the so-called load-bearing capacity of the liquid film is as high as possible. This ensures that there is a certain lubricating effect even in the event of an emergency.

Aufgabe der Erfindung ist es deshalb, Traktionsflüssigkeiten bereitzustellen, die eine hohe Reibungszahl in Verbindung mit einer hohen Tragfähigkeit besitzen. Diese Aufgabe wird mit der vorliegenden Erfindung gelöst.The object of the invention is therefore to provide traction fluids which have a high coefficient of friction in conjunction with a high load-bearing capacity. This object is achieved with the present invention.

Gegenstand der Erfindung ist die Verwendung von Verbindungen mit einem oder mehreren durch eine oder zwei Alkylenketten, die ein oder zwei Kohlenstoffatome aufweisen, verbrückten Cyclohexan- und/oder Cycloheptanring, der durch einen oder mehrere Substituenten aus der Gruppe Alkyl, Alkyliden, Alkoxy, Alkanoyl, Alkylcarbonyloxy, Alkoxycarbonyl, Oxoalkyl, Merkapto, Alkylmerkapto, Alkanoylmerkapto, Halogen und Hydroxyl substituiert ist und worin die Alkyl- und Alkylidenreste 1 bis 7 Kohlenstoffatome besitzen und worin Alkyl in den 0-haltigen Substituenten auch Cycloalkyl bedeuten kann, und zwei an das gleiche oder verschiedene Ringkohlenstoffatome gebundene Alkylgruppen zusammen auch eine Alkylengruppe bilden können, und das Ringsystem, die Alkyl-, Cycloalkyl- und/oder Alkylengruppen auch eine oder mehrere Doppelbindungen enthalten können, und worin die Alkyl- und/oder Alkylengruppen der genannten Substituenten durch ein oder mehrere Reste aus der Gruppe Alkyl, Cycloalkyl, Hydroxy, Halogen, Alkoxy, Cycloalkoxy, Alkanoyl, Alkylcarbonyloxy, Alkoxycarbonyl, Merkapto, Cycloalkoxycarbonyl und Cyano, in denen eine Alkyl- oder Cycloalkylgruppe 1 bis 7 Kohlenstoffatome besitzen und zusammen auch Cycloalkyl-alkyl darstellen und eine oder mehrere Doppelbindungen enthalten können, substituiert sein können, und worin zwei oder mehrere verbrückte Cyclohexan- und/oder Cycloheptanringe über die genannten Substituenten miteinander verbunden sein können, als Traktionsflüssigkeit in Reibgetrieben.The invention relates to the use of compounds having one or more cyclohexane and / or cycloheptane rings bridged by one or two alkylene chains which have one or two carbon atoms and which are substituted by one or more substituents from the The group alkyl, alkylidene, alkoxy, alkanoyl, alkylcarbonyloxy, alkoxycarbonyl, oxoalkyl, mercapto, alkylmerkapto, alkanoylmerkapto, halogen and hydroxyl is substituted and in which the alkyl and alkylidene radicals have 1 to 7 carbon atoms and in which alkyl in the 0-containing substituents also mean cycloalkyl can, and two alkyl groups bonded to the same or different ring carbon atoms together can also form an alkylene group, and the ring system, the alkyl, cycloalkyl and / or alkylene groups can also contain one or more double bonds, and in which the alkyl and / or alkylene groups said substituents by one or more radicals from the group alkyl, cycloalkyl, hydroxy, halogen, alkoxy, cycloalkoxy, alkanoyl, alkylcarbonyloxy, alkoxycarbonyl, mercapto, cycloalkoxycarbonyl and cyano, in which an alkyl or cycloalkyl group have 1 to 7 carbon atoms and together also Represent cycloalkyl-alkyl and one or more double bonds may contain, may be substituted, and wherein two or more bridged cyclohexane and / or cycloheptane rings may be connected to one another via the substituents mentioned, as traction fluid in friction gears.

Das durch zwei oder vorzugsweise eine Alkylgruppe mit 1 oder 2 Kohlenstoffatomen verbrückte Cyclohexan- oder Cycloheptanringsystem ist vorzugsweise ein durch Methylen oder Äthylen verbrückter Cyclohexanring, wie z. B. Bicyclo[2.2.2]octan, und insbesondere Bicyclo/3.2.1/octan, Bicyclo[3.1.1]heptan, Bicyclo[2.2.1]heptan oder Tricyclo[5.2.1.02,6]decan. Das Ringsystem kann auch eine oder mehrere, vorzugsweise eine Doppelbindung enthalten, und ist dann z. B. Bicyclo[2.2.1]hept-5-en.The cyclohexane or cycloheptane ring system bridged by two or preferably an alkyl group having 1 or 2 carbon atoms is preferably a cyclohexane ring bridged by methylene or ethylene, such as, for example, B. bicyclo [2.2.2] octane, and in particular bicyclo / 3.2.1 / octane, bicyclo [3.1.1] heptane, bicyclo [2.2.1] heptane or tricyclo [5.2.1.0 2.6 ] decane. The ring system can also contain one or more, preferably a double bond, and is then z. B. Bicyclo [2.2.1] hept-5-ene.

Eine Alkylgruppe mit 1 bis 7 Kohlenstoffatomen kann geradkettig oder verzweigt sein und ist z. B. Methyl, Äthyl, Propyl, Isopropyl, Butyl, Isobutyl, tert.-Butyl, Pentyl, Isopentyl, Neopentyl, Hexyl, Isohexyl, Heptyl, Isoheptyl, 2,3,3-Trimethyl-butyl, usw. Bevorzugt sind Alkylgruppen mit 1 bis 4, und insbesondere mit 1 oder 2 Kohlenstoffatomen.An alkyl group with 1 to 7 carbon atoms can be straight-chain or branched and is e.g. Example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, heptyl, isoheptyl, 2,3,3-trimethyl-butyl, etc. Preferred are alkyl groups with 1 to 4, and in particular with 1 or 2 carbon atoms.

Eine Alkylidengruppe leitet sich von einer der genannten Alkylgruppen mit 1 bis 7 Kohlenstoffatomen ab, insbesondere von einer der bevorzugten genannten Alkylgruppen, und ist z. B. Methyliden oder Äthyliden.An alkylidene group is derived from one of the alkyl groups mentioned having 1 to 7 carbon atoms, in particular from one of the preferred alkyl groups mentioned, and is z. B. methylidene or ethylidene.

Eine aus zwei Alkylsubstituenten gebildete Alkylengruppe besitzt vorzugsweise 2 bis 5 Kohlenstoffatome und ist z. B. eine Äthylen-, Propylen-, Butylen- oder Pentylengruppe. Ein mit einer solchen Alkylengruppe substituiertes verbrücktes Ringsystem ist z. B. Cyclopropan-<1-spiro-2>-norbornan oder Decahydro-1,4- methano-azulen.An alkylene group formed from two alkyl substituents preferably has 2 to 5 carbon atoms and is e.g. B. an ethylene, propylene, butylene or pentylene group. A bridged ring system substituted with such an alkylene group is e.g. B. cyclopropane <1-spiro-2> norbornane or decahydro-1,4-methano-azulene.

Eine Cycloalkylgruppe ist eine solche mit 3 bis 7, vorzugsweise 5 bis 7 Kohlenstoffatomen und ist z.-B. Cyclopropyl, Cyclobutyl, Cyclopentyl, Cycloheptyl, und insbesondere Cyclohexyl. Eine Cycloalkyl-alkylgruppe ist eine solche, die sich aus den genannten Cycloalkyl-und Alkylresten, insbesondere aus den bevorzugt genannten, zusammensetzt.A cycloalkyl group is one with 3 to 7, preferably 5 to 7 carbon atoms and is e.g. Cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, and especially cyclohexyl. A cycloalkyl-alkyl group is one which is composed of the cycloalkyl and alkyl radicals mentioned, in particular of the preferred ones.

Eine Alkyl- oder Cycloalkylgruppe kann auch eine oder mehrere, z. B. zwei, und insbesondere eine Doppelbindung enthalten. Eine Cycloalkylgruppe mit mehr als zwei, d. h. also drei Doppelbindungen, ist Cycloheptatrien-(1,3,5)-yl und insbesondere Phenyl.An alkyl or cycloalkyl group can also one or more, e.g. B. contain two, and in particular a double bond. A cycloalkyl group with more than two, i.e. H. So three double bonds, is cycloheptatrien- (1,3,5) -yl and especially phenyl.

Eine Alkoxy-, Alkanoyl-, Alkylcarbonyloxy- und eine Alkoxycarbonylgruppe leiten sich von den genannten, insbesondere den bevorzugt genannten Alkyl- und Cycloalkylresten ab. Sie sind z. B. Methoxy, Äthoxy, Cyclohexyloxy, Acetyl, Propionyl, Hexylcarbonyl, Acetoxy, Propionyloxy, Hexylcarbonyloxy, Äthoxycarbonyl, Hexyloxycarbonyl, 1- oder 2-Cyclohexylpropyl-(2)-oxy usw.An alkoxy, alkanoyl, alkylcarbonyloxy and an alkoxycarbonyl group are derived from the alkyl and cycloalkyl radicals mentioned, in particular the preferably mentioned. You are e.g. B. methoxy, ethoxy, cyclohexyloxy, acetyl, propionyl, hexylcarbonyl, acetoxy, propionyloxy, hexylcarbonyloxy, ethoxycarbonyl, hexyloxycarbonyl, 1- or 2-cyclohexylpropyl- (2) -oxy etc.

Eine Oxoalkylgruppe ist eine durch eine oder mehrere, insbesondere eine oder zwei Oxogruppen substituierte Alkylgruppe, die sich von einer der genannten Alkylreste oder auch Cycloalkylreste ableitet. Sie ist z. B. 2-Oxo-äthyl, 2- oder 3-Oxo-propyl, Mono- oder Dioxo-butyl, Pentyl- oder Hexyl, wie z. B. 1,4-Dioxopentyl, 2,5-Dioxo-hexyl, Oxocyclohexyl, und insbesondere Formyl.An oxoalkyl group is an alkyl group which is substituted by one or more, in particular one or two, oxo groups and which is derived from one of the alkyl radicals mentioned or also cycloalkyl radicals. It is e.g. B. 2-oxo-ethyl, 2- or 3-oxo-propyl, mono- or dioxo-butyl, pentyl or hexyl, such as. B. 1,4-dioxopentyl, 2,5-dioxo-hexyl, oxocyclohexyl, and especially formyl.

Halogen als Substituent bedeutet vorzugsweise Fluor und insbesondere Chlor.Halogen as a substituent preferably means fluorine and in particular chlorine.

Die erfindungsgemäßen Verbindungen enthalten einen oder mehrere gleiche oder verschiedene, vorzugsweise zwei und insbesondere einen verbrückten Cyclohexan- und/oder Cycloheptanring. Ein diese Ringe verbindender Rest ist ein solcher, der sich von den genannten Substituenten ableitet, die in diesem Fall also gemeinsame Substituenten der zu verbindenden Ringsysteme sind. Solche Substituenten sind z. B. von den Alkyl- oder Cycloalkylsubstituenten abgeleitete Alkylen- oder Cycloalkylengruppen, wie z. B. Cyclohexylen-(1,4), oder auch eine Alkylen-cycloalkylen-Gruppe, von den Alkoxy- oder Alkoxycarbonylgruppen abgeleitete Alkylenoxy- oder Alkylenoxycarbonylgruppen -alkylen-0- oder -alkylen-0-C(0)-, von den Alkanoylgruppen abgeleitete Alkylen- carbonyloxygruppen-alkylen-C(0)-0-, eine Oxycarbonylgruppe-O-C(O)-, Carbonyloxyalkylenoxcarbonylgruppen-C(0)-O-alkylen-O-C(O)-, Alkylenoxycarbonylalkylengruppen-alkylen-O-C(O)-alkylen- usw.The compounds according to the invention contain one or more identical or different, preferably two and in particular one bridged, cyclohexane and / or cycloheptane ring. A radical which connects these rings is one which is derived from the substituents mentioned, which in this case are therefore common substituents of the ring systems to be connected. Such sub stituents are e.g. B. derived from the alkyl or cycloalkyl substituents alkylene or cycloalkylene groups, such as. B. cyclohexylene (1,4), or an alkylene-cycloalkylene group, derived from the alkoxy or alkoxycarbonyl groups, alkyleneoxy or alkyleneoxycarbonyl groups -alkylene-0 or -alkylene-0-C (0) -, from the alkanoyl groups derived alkylene-carbonyloxy group-alkylene-C (0) -0-, an oxycarbonyl group-OC (O) -, carbonyloxyalkyleneoxcarbonyl group-C (0) -O-alkylene-OC (O) -, alkyleneoxycarbonylalkylene group-alkylene-OC (O) - alkylene, etc.

Die verbrückten Ringsysteme und/oder die Alkyl- und Alkylengruppen der Substituenten der verbrückten Ringsysteme können durch einen oder mehrere, vorzugsweise 1 bis 5, und insbesondere ein oder zwei der dafür genannten Reste substituiert sein, die gleich oder verschieden sein können. Typische Substituenten oder zusammengesetzte Substituenten der Ringsysteme sind z. B. Hydroxy, Hydroxymethyl, Hydroxyäthyl, 1-Methyl-hydroxyäthyl, Acetoxy, Acetoxymethyl, Cyclohexylcarbonyl, Cyclohexyloxycarbonyl, Cyclohexylcarbönyloxy, Cyclohexylcarbonyloxymethyl, Cyclohexyloxycarbonylmethyl, 2-Äthoxycarbonyl-2-cyano-äthyl, 1-Methyl-l-cyclohexyl-äthoxycarbonyl, 1-Methyl-1-(4-methyl-cyclohexen-3-yl)-äthoxycarbonyl, 1,1-Dichlor-äthylen- (vorzugsweise an das gleiche Kohlenstoffatom des verbrückten Ringsystems unter Bildung eines Spiro-cyclopropanrings gebunden) oder 1-Methyl-1-carbonyloxy-4-(1-methyl-1-carbonyloxy- äthyl)-cyclohexan (als gemeinsamer, über die beiden Carbonylgruppen gebundener Substituent von zwei verbrückten Ringsystemen).The bridged ring systems and / or the alkyl and alkylene groups of the substituents of the bridged ring systems can be substituted by one or more, preferably 1 to 5, and in particular one or two of the radicals mentioned therefor, which may be the same or different. Typical substituents or compound substituents of the ring systems are e.g. B. Hydroxy, hydroxymethyl, hydroxyethyl, 1-methyl-hydroxyethyl, acetoxy, acetoxymethyl, cyclohexylcarbonyl, cyclohexyloxycarbonyl, cyclohexylcarbönyloxy, cyclohexylcarbonyloxymethyl, cyclohexyloxycarbonylmethyl, 2-ethoxycarbonyl-2-cyano-ethyl, 1-methyloxy-1-methyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl-1-methyl-ethyl Methyl-1- (4-methyl-cyclohexen-3-yl) ethoxycarbonyl, 1,1-dichloroethylene (preferably bonded to the same carbon atom of the bridged ring system to form a spirocyclopropane ring) or 1-methyl-1- carbonyloxy-4- (1-methyl-1-carbonyloxy-ethyl) -cyclohexane (as a common substituent of two bridged ring systems bound via the two carbonyl groups).

Wie oben erwähnt, werden auch Tricyclo[5.2.1.02,6]decane bevorzugt, die durch 1 bis 5, vorzugsweise 1 bis 3 Substituenten aus der Gruppe Alkyl, Hydroxy, Mercapto, Alkoxy, Alkylmercapto, Alkanoyloxy und Alkanoylmercapto substituiert sind und worin eine Alkylgruppe (bzw. Alkanoylgruppe) 1 bis 7 Kohlenstoffatome besitzt und gegebenenfalls durch eine oder mehrere, insbesondere ein oder zwei Hydroxygruppen, Mercaptogruppen und/oder Halogen, insbesondere Brom oder Chlor, substituiert sein kann.As mentioned above, tricyclo [5.2.1.0 2,6 ] decanes are also preferred which are substituted by 1 to 5, preferably 1 to 3, substituents from the group consisting of alkyl, hydroxy, mercapto, alkoxy, alkylmercapto, alkanoyloxy and alkanoylmercapto and in which one Alkyl group (or alkanoyl group) has 1 to 7 carbon atoms and can optionally be substituted by one or more, in particular one or two, hydroxyl groups, mercapto groups and / or halogen, in particular bromine or chlorine.

Das Tricyclo[5.2.1.o2,6]decan (TDC) weist folgende Struktur auf:

Figure imgb0001
Zur Verwendung von Reibradgetrieben gut geeignete repräsentative erfindungsgemäße Verbindungen sind z. B. das 2-Hydroxymethyl-6,6-dimethyl-bicyclo[3.1.1]heptan, 2-Hydroxymethyl-3,3-dimethyl-bicyclo[2.2.1]heptan, 3-Acetoxy-2,6,6-trimethyl-bicyclo[3.1.1]heptan, 2-Acetoxymethyl-6,6-dimethyl-bicyclo[3.1.1]heptan, 2-(2-Hydroxyäthyl)-3,3-dimethyl-bicyclo[2.2.1]heptan, 2-Methyliden-3-acetoxy-6,6-dimethyl-bicyclo[3.1.1]heptan, 4,8,8-Trimethyl-9-acetoxymethyl-decahydro-1,4- methano-azulen, 4,8,8-Trimethyl-9-hydroxymethyl-decahydro-l,-4-methano- azulen, 2-Cyano-3-(3,3-dimethyl-bicyclo[2.2.1]-hept-2-yl-propionsäureäthylester, 2,2-Dichlor-cyclopropan- <1-spiro-2>-6,6-dimethyl-bicyclo[3.1.1]heptan, (3,3-Dimethyl- bicyclo[2.2.1.]hept-2-yl)-carbonsäure-cyclohexylester, 3-Cyclohexylcarbonyloxymethyl-6,6-dimethyl-bicyclo[3.1.1] heptan, 3-Cyclohexylcarbonyloxy-2,6,6-trimethyl- bicyclo[3.1.1]heptan, 3-(3,3-Dimethyl-bicyclo[2.2.1]hept-2-yl)--carbonyloxy-2,6,6-trimethyl-bicyclo[3.1.1]heptan, 3-(3,3-Dimethyl-bicyclor2.2.1]-hept-2-yl)-carbonyloxy- methyl-2,2-dimethyl-bicyclo[2.2.1]-heptan, Bornan-(und/oder Isobornan)-yl-cyclohexancarbonsäureester, 2-(1-Methyl-1-cyclohexyl-äthoxycarbonyl)-3,3-dimethyl-bicyclo[2.2.1]-heptan, 4,8,8-Trimethyl-9-(3,3-dimethyl-bicyclo[2.2.1]-hept-2-yl-carbonyloxymethyl-decahydro-1,4-methano-azulen, Isoborneol, 2-£1-(4-Methyl-cyclohex-3-enyl)-1-methyl- äthoxycarbonyl]-3,3-dimethyl-bicyclo[2.2.1]heptan, 1-Methyl-1-[(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-car- bonyloxy]-4-[1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)--1-methyl-äthyl]-cyclohexan; insbesondere das 3-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]heptan, 2,2-Dimethyl-3-cyclohexyloxycarbonylmethyl-bicyclo[2.2.1]heptan, 2,2-Dimethyl-3-(2-cyano-2-äthoxycarbonyl-äthyl)-bicyclo [2.2.1]heptan, 2,2-Dichlor-cyclopropan 1-spiro-2 -3,3-dimethyl-norbornan, 4,8,8-Trimethyl-9-formyl- decahydro-1,4-methano-azulen; und in erster Linie das 1,5-Dimethyl-6-cyclohexanoyloxy-bicyclo[3.2.1]octan, das 2,2-Dimethyl-3-cyclohexanoyloxy-methyl-bicyclo-[2.2.1]-heptan, das 4,8,8-Trimethyl-9-cyclohexanoyloxy- methyl-decahydro-1,4-methano-azulen das 4,8,8-Trimethyl-9-(2-cyano-2-äthoxycarbonyl-äthyl)-decahydro-1,4-methano- azulen, das 8(9)-Hydroxy-, das 8(9),3,4-Trihydroxy-, das 3(4)-Hydroxymethylen-, das 3(4) oder 8(9)-Diacetyloxy-und das 3(4,5)-Di-isobuttersäureester-tricyclo[5.2.1.o2,6]-decan.The tricyclo [5.2.1.o 2.6 ] decane (TDC) has the following structure:
Figure imgb0001
 Representative compounds according to the invention which are well suited for use with friction wheel gears are e.g. B. 2-hydroxymethyl-6,6-dimethyl-bicyclo [3.1.1] heptane, 2-hydroxymethyl-3,3-dimethyl-bicyclo [2.2.1] heptane, 3-acetoxy-2,6,6-trimethyl -bicyclo [3.1.1] heptane, 2-acetoxymethyl-6,6-dimethyl-bicyclo [3.1.1] heptane, 2- (2-hydroxyethyl) -3,3-dimethyl-bicyclo [2.2.1] heptane, 2 -Methylidene-3-acetoxy-6,6-dimethyl-bicyclo [3.1.1] heptane, 4,8,8-trimethyl-9-acetoxymethyl-decahydro-1,4-methano-azulene, 4,8,8-trimethyl -9-hydroxymethyl-decahydro-l, -4-methano-azulene, 2-cyano-3- (3,3-dimethyl-bicyclo [2.2.1] -hept-2-yl-propionic acid ethyl ester, 2,2-dichloro- cyclopropan- <1-spiro-2> -6,6-dimethyl-bicyclo [3.1.1] heptane, (3,3-dimethyl- bicyclo [2.2.1.] hept-2-yl) carboxylic acid cyclohexyl ester, 3-cyclohexylcarbonyloxymethyl-6,6-dimethyl-bicyclo [3.1.1] heptane, 3-cyclohexylcarbonyloxy-2,6,6-trimethyl-bicyclo [ 3.1.1] heptane, 3- (3,3-dimethyl-bicyclo [2.2.1] hept-2-yl) - carbonyloxy-2,6,6-trimethyl-bicyclo [3.1.1] heptane, 3- ( 3,3-dimethyl-bicyclor2.2.1] -hept-2-yl) -carbonyloxy-methyl-2,2-dimethyl-bicyclo [2.2.1] -heptane, bornane (and / or isobornane) -yl-cyclohexane carboxylic acid ester, 2- (1-methyl-1-cyclohexyl-ethoxycarbonyl) -3,3-dimethyl-bicyclo [2.2.1] heptane, 4,8,8-trimethyl-9- (3,3-dimethyl-bicyclo [2.2. 1] -hept-2-yl-carbonyloxymethyl-decahydro-1,4-methano-azulene, isoborneol, 2- £ 1- (4-methyl-cyclohex-3-enyl) -1-methyl-ethoxycarbonyl] -3.3 -dimethyl-bicyclo [2.2.1] heptane, 1-methyl-1 - [(3,3-dimethyl-bicyclo [2.2.1] hept-2-yl) -carbonyloxy] -4- [1- (3rd , 3-dimethyl-bicyclo [2.2.1] hept-2-yl) - 1-methyl-ethyl] -cyclohexane, in particular 3-hydroxy-2,6,6-trimethyl-bicyclo [3.1.1] heptane, 2,2-dimethyl-3-cyclohexyloxycarbonylmethyl-bicyclo [2.2.1] heptane, 2,2-dimethy l-3- (2-cyano-2-ethoxycarbonyl-ethyl) bicyclo [2.2.1] heptane, 2,2-dichlorocyclopropane 1-spiro-2 -3,3-dimethyl-norbornane, 4,8,8 Trimethyl-9-formyl-decahydro-1,4-methano-azulene; and primarily 1,5-dimethyl-6-cyclohexanoyloxy-bicyclo [3.2.1] octane, 2,2-dimethyl-3-cyclohexanoyloxy-methyl-bicyclo- [2.2.1] heptane, 4.8 , 8-Trimethyl-9-cyclohexanoyloxy-methyl-decahydro-1,4-methano-azulene 4,8,8-trimethyl-9- (2-cyano-2-ethoxycarbonyl-ethyl) -decahydro-1,4-methano azulene, the 8 (9) hydroxy, the 8 (9), 3,4-trihydroxy, the 3 (4) hydroxymethylene, the 3 (4) or 8 (9) diacetyloxy and the 3rd (4,5) -di-isobutyric acid ester tricyclo [5.2.1.o 2,6 ] -decane.

Die erfindungsgemäß verwendeten Verbindungen sind bekannt oder können nach an sich bekannten Methoden in Analogie zu den bekannten Verbindungen oder aus den bekannten Verbindungen, z. B. durch Veresterung, Verseifung, Verätherung, Halogenierung usw. hergestellt werden.The compounds used according to the invention are known or can be prepared by methods known per se in analogy to the known compounds or from the known compounds, e.g. B. by esterification, saponification, etherification, halogenation, etc.

Die erfindungsgemäßen Verbindungen eignen sich hervorragend als Kraftübertragungsfluide für Traktionsgetriebe, wie z. B. in Umschlingungsgetrieben oder Wälzgetrieben. Sie zeichnen sich durch eine besonders günstige Kombination von Traktionseigenschaften (hohe Reibungszahlen im Bereich von etwa 0,05 bis etwa 0,11, starken Anstieg der Reibungszahl im Bereich eines Schlupfes bis 1 %) und Notlaufeigenschaften (hohe Tragfähigkeit des Flüssigkeitsfilms) aus.The compounds of the invention are ideal as power transmission fluids for traction gearboxes, such as. B. in belt drives or roller drives. They are characterized by a particularly favorable combination of traction properties (high coefficients of friction in the range from approximately 0.05 to approximately 0.11, sharp increase in the coefficient of friction in the range of slip up to 1%) and emergency running properties (high load-bearing capacity of the liquid film).

Die erfindungsgemäßen Verbindungen können allein oder im Gemisch mit anderen erfindungsgemäßen Verbindungen, aber auch im Gemisch mit anderen bekannten Traktionsflüssigkeiten verwendet werden. Als andere Traktionsflüssigkeiten eignen sich beispielsweise ganz oder teilweise hydrierte Cyclopentylbiphenylene und -naphthaline mit einer bis zwei Cyclopentylgruppen. Daneben können sie auch noch übliche Zusatzstoffe in den dafür üblichen Mengen enthalten, wie z. B. Antioxidantien, Rostinhibitoren, Dichtaufquellmittel, Antischaummittel, Dispergiermittel, Farbstoffe, Viskositätsindexverbesserer, Extreme Pressure Additives, Antiverschleiß-Additive und/oder auch Schmiermittel.The compounds according to the invention can be used alone or in a mixture with other compounds according to the invention, but also in a mixture with other known traction liquids. Other traction fluids are, for example, fully or partially hydrogenated cyclopentylbiphenylenes and naphthalenes with one or two cyclopentyl groups. In addition, they can also contain conventional additives in the usual amounts, such as. B. antioxidants, rust inhibitors, density swellers, antifoams, dispersants, dyes, viscosity index improvers, extreme pressure additives, antiwear additives and / or lubricants.

Werden die erfindungsgemäßen Verbindungen in Mischung mit anderen Traktionsflüssigkeiten verwendet, so enthalten diese Mischungen die erfindungsgemäßen Verbindungen im allgemeinen in einer Menge von mindestens 5 Gew.-%, insbesondere von mindestens 30 Gew.-%. Der Gehalt richtet sich dabei insbesondere nach der Art und den Eigenschaften der anderen Traktionsflüssigkeiten.If the compounds according to the invention are used in a mixture with other traction liquids, these mixtures generally contain the compounds according to the invention in an amount of at least 5% by weight, in particular at least 30% by weight. The content depends in particular on the type and properties of the other traction fluids.

Die folgenden Beispiele erläutern die Erfindung, ohne sie darauf zu beschränken.The following examples illustrate the invention without restricting it.

B e i s p i e 1 1Example: 1 1

In einem Zwei-Scheiben-Reibungsprüfstand nach K. Stößel (Konstruktion 31, 1979, 2 bis 6) wird die Abhängigkeit der Reibungszahl µ vom Schlupf s bestimmt.The dependence of the coefficient of friction µ on the slip s is determined in a two-disc friction test bench according to K. Stößel (construction 31, 1979, 2 to 6).

Die Scheiben bestehen aus einem Werkstoff, der nach DIN 17006 mit 100 Cr 6 beschrieben wird. Die Scheiben haben einen Durchmesser von 80 mm. Der arithmetische Mittenrauhwert Ra (Center Line Average CLA) der An- und Abtriebsscheibe liegt im Bereich von 0,03 bis 0,12 µm.The washers are made of a material that is described as 100 Cr 6 in accordance with DIN 17006. The discs have a diameter of 80 mm. The arithmetic mean roughness R a (Center Line Average CLA) of the drive and driven pulley is in the range from 0.03 to 0.12 µm.

Die zu prüfende Flüssigkeit wird bei einer Einspritztemperatur von 50 °C zwischen die beiden Scheiben gespritzt.The liquid to be tested is injected between the two disks at an injection temperature of 50 ° C.

B e i s p i e 1 2Example: 1 2

In dem in Beispiel 1 beschriebenen Zwei-Scheiben-Reibungsprüfstand wurden die folgenden Verbindungen untersucht, für die in den Fig. 1 bis 27 der Zeichnung die Abhängigkeit der Reibungszahlen vom Schlupf bei verschiedenen Anpreßkräften FN (im Bereich von 125 bis 4080 N) und Umfangsgeschwindigkeiten v1 (im Bereich von 0,42 bis 12,57 m/s) dargestellt wird.In the two-disk friction test bench described in Example 1, the following connections were investigated, for which the dependency of the coefficients of friction on the slip at different contact forces F N (in the range from 125 to 4080 N) and peripheral speeds in FIGS. 1 to 27 of the drawing v 1 (in the range of 0.42 to 12.57 m / s) is shown.

Als Traktionsflüssigkeit wurden verwendet: 4,8,8-Trimethyl-9-formyl-decahydro-1,4-methano-azulen (Siedepunkt 116 bis 120 °C bei 0,7 mbar) (Fig. 1 bis 5), 2,2-Dichlor-cyclopropan-<1-spiro-2> -3,3-dimethyl- norbornan (Siedepunkt 120 °C bei 18 mbar) (Fig. 6 bis 10), 3-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]heptan (Siedepunkt 94 °C bei 13 mbar) (Fig. 11 bis 14), 4,8,8-Trimethyl-9-cyclohexanoyloxymethyl-decahydro-1,4-methano-azulen (Fig. 15 bis 18), 1,5-Dimethyl-6-cyclohexanoyloxy-bicyclo[3.2.1]octan (Fig. 19 bis 23) und 2,2-Dimethyl-3-cyclohexyloxycarbonylmethyl-bicyclo [2.2.1]-heptan (Fig. 24 bis 27).The following traction fluid was used: 4,8,8-trimethyl-9-formyl-decahydro-1,4-methano-azulene (boiling point 116 to 120 ° C at 0.7 mbar) (Fig. 1 to 5), 2.2 -Dichloro-cyclopropane <1-spiro-2> -3,3-dimethyl-norbornane (boiling point 120 ° C at 18 mbar) (Fig. 6 to 10), 3-hydroxy-2,6,6-trimethyl-bicyclo [3.1.1] heptane (boiling point 94 ° C. at 13 mbar) (FIGS. 11 to 14), 4,8,8-trimethyl-9-cyclohexanoyloxymethyl-decahydro-1,4-methano-azulene (FIGS. 15 to 18 ), 1,5-dimethyl-6-cyclohexanoyloxy-bicyclo [3.2.1] octane (Fig. 19 to 23) and 2,2-dimethyl-3-cyclohexyloxycarbonylmethyl-bicyclo [2.2.1] -heptane (Fig. 24 to 27).

B e i s p i e 1 3Example: 1 3

Wie in Beispiel 2 beschreiben, wurden verschiedene Tricyclo[5.2.1.o2,6]-decane untersucht.As described in Example 2, various tricyclo [5.2.1.o 2,6 ] decanes were investigated.

Die Ergebnisse sind in den Figuren 28 bis 37 der beigefügten Zeichnung dargestellt.The results are shown in Figures 28 to 37 of the accompanying drawings.

Als Traktionsflüssigkeiten wurden verwendet:

  • Das 8(9)-Hydroxyderivat (TDC Alkohol A; Fig. 28, 29),
  • das 8(9),3,4-Trihydroxyderivat (TDC Alkohol B; Fig. 30, 31),
  • das 3(4)-Hydroxymethylderivat (TDC Alkohol C; Fig. 32, 33),
  • Das Di-Acetylesterderivat; (Fig. 34, 35) und
  • das Di-Isobuttersäureesterderivat (Fig. 36, 37).
The following traction fluids were used:
  • The 8 (9) hydroxy derivative (TDC alcohol A; Fig. 28, 29),
  • the 8 (9), 3,4-trihydroxy derivative (TDC alcohol B; Fig. 30, 31),
  • the 3 (4) hydroxymethyl derivative (TDC alcohol C; Fig. 32, 33),
  • The di-acetylester derivative; (Figs. 34, 35) and
  • the di-isobutyric acid ester derivative (Fig. 36, 37).

Claims (19)

1. Verwendung von Verbindungen mit einem oder mehreren durch eine oder zwei Alkylenketten, die ein oder zwei Kohlenstoffatome aufweisen, verbrückten Cyclohexan und/oder Cycloheptanring, der durch einen oder mehrere Substituenten aus der Gruppe Alkyl, Alkyliden, Alkoxy, Alkanoyl, AlkylcarbcnyLoxy, Alkoxycarbonyl, Oxoalkyl, Merkapto, Alkylmerkapto, Alkanoylmerkapto, Halogen und Hydroxyl substituiert ist und worin die Alkyl- und Alkylidenreste 1 bis 7 Kohlenstoffatome besitzen und worin Alkyl in den 0-haltigen Substituenten auch Cycloalkyl bedeuten kann, und zwei an das gleiche oder verschiedene Ringkohlenstoffatome gebundene Alkylgruppen zusammen auch eine Alkylengruppe bilden können, und das Ringsystem, die Alkyl-, Cycloalkyl- und/oder Alkylengruppen auch eine oder mehrere Doppelbindungen enthalten können, und worin die Alkyl- und/oder Alkylengruppen der genannten Substituenten durch ein oder mehrere Reste aus der Gruppe Alkyl, Cycloalkyl, Hydroxy, Halogen, Alkoxy, Cycloalkoxy, Alkanoyl, Alkylcarbonyloxy, Alkyloxycarbonyl, Merkapto, Cycloalkyloxycarbonyl und Cyano, in denen eine Alkyl- oder Cycloalkylgruppe 1 bis 7 Kohlenstoffatome besitzen und zusammen auch Cycloalkylalkyl darstellen und eine oder mehrere Doppelbindungen enthalten können, substituiert sein können, und worin zwei oder mehrere verbrückte Cyclohexan-und/oder Cycloheptanringe über die genannten Substituenten miteinander verbunden sein können, als Traktionsflüssigkeit in Reibgetrieben.1. Use of compounds having one or more cyclohexane and / or cycloheptane ring bridged by one or two alkylene chains which have one or two carbon atoms and which is substituted by one or more substituents from the group alkyl, alkylidene, alkoxy, alkanoyl, alkylcarboxy loxy, alkoxycarbonyl, Oxoalkyl, mercapto, alkylmerkapto, alkanoylmerkapto, halogen and hydroxyl and in which the alkyl and alkylidene radicals have 1 to 7 carbon atoms and in which alkyl in the 0-containing substituents can also mean cycloalkyl, and two alkyl groups bonded to the same or different ring carbon atoms can also together form an alkylene group, and the ring system, the alkyl, cycloalkyl and / or alkylene groups also one or more double bonds may contain, and wherein the alkyl and / or alkylene groups of the substituents mentioned by one or more radicals from the group alkyl, cycloalkyl, hydroxy, halogen, alkoxy, cycloalkoxy, alkanoyl, alkylcarbonyloxy, alkyloxycarbonyl, mercapto, cycloalkyloxycarbonyl and cyano, in which one Alkyl or cycloalkyl groups have 1 to 7 carbon atoms and together also represent cycloalkylalkyl and can contain one or more double bonds, can be substituted, and in which two or more bridged cyclohexane and / or cycloheptane rings can be connected to one another via the substituents mentioned, as traction fluid in Friction drives. 2. Verwendung nach Anspruch 1, dadurch gekennzeichnet , daß die Verbindungen einen oder zwei gleiche oder verschiedene verbrückte Cyclohexan- und/oder Cyeloheptanringe enthalten.2. Use according to claim 1, characterized in that the compounds contain one or two identical or different bridged cyclohexane and / or cyeloheptane rings. 3. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß ein verbrückter Ring ein Bicyclo[3.2.1]octan, Bicyclo[3.1.1]heptan, Bicyclo[2.2.1]heptan oder Tricyclo[5.2.1.02,6]decan ist.3. Use according to claim 1 or 2, characterized in that a bridged ring is a bicyclo [3.2.1] octane, bicyclo [3.1.1] heptane, bicyclo [2.2.1] heptane or tricyclo [5.2.1.0 2.6 ] is decan. 4. Verwendung nach Anspruch 3, dadurch gekennzeichnet , daß das Bicyclo[2.2.1]heptan zusammen mit einer Alkylengruppe als Substituent ein Cyclopropan-<1-spiro-2> -norbornan oder Decahydro-1,4-methano-azulen bildet.4. Use according to claim 3, characterized in that the bicyclo [2.2.1] heptane together with an alkylene group as a substituent forms a cyclopropane <1-spiro-2> norbornane or decahydro-1,4-methano-azulene. 5. Verwendung nach Anspruch 3, dadurch gekennzeichnet, daß man das 1,5-Dimethyl-6-cyclohexanoyloxy-bicyclo[3.2.1]octan einsetzt.5. Use according to claim 3, characterized in that the 1,5-dimethyl-6-cyclohexanoyloxy-bicyclo [3.2.1] octane is used. 6. Verwendung nach Anspruch 3, dadurch gekennzeichnet , daß man das 2,2-Dimethyl-3-cyclohexanoyloxymethyl-bicyclo [2.2.1]heptan einsetzt.6. Use according to claim 3, characterized in that the 2,2-dimethyl-3-cyclohexanoyloxymethyl-bicyclo [2.2.1] heptane is used. 7. Verwendung nach Anspruch 3, dadurch gekennzeichnet , daß man das 3-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]heptan einsetzt.7. Use according to claim 3, characterized in that the 3-hydroxy-2,6,6-trimethyl-bicyclo [3.1.1] heptane is used. 8. Verwendung nach Anspruch 3, dadurch gekennzeichnet , daß man das 2,2-Dimethyl-3-cyclohexyloxycarbonylmethyl- bicyclo[2.2.1]heptan einsetzt.8. Use according to claim 3, characterized in that the 2,2-dimethyl-3-cyclohexyloxycarbonylmethyl-bicyclo [2.2.1] heptane is used. 9. Verwendung nach-Anspruch 3, dadurch gekennzeichnet , daß man das 2,2-Dimethyl-3-(2-cyano-2-äthoxycarbonyl-äthyl)-bicyclo[2.2.1]heptan einsetzt.9. Use according to claim 3, characterized in that the 2,2-dimethyl-3- (2-cyano-2-ethoxycarbonyl-ethyl) -bicyclo [2.2.1] heptane is used. 10. Verwendung nach Anspruch 4, dadurch gekennzeichnet , daß man das 2,2-Dichlor-cyclopropan<1-spiro-2> -3,3-dimethyl- norbornan einsetzt.10. Use according to claim 4, characterized in that the 2,2-dichloro-cyclopropane <1-spiro-2> -3,3-dimethyl-norbornane is used. 11. Verwendung nach Anspruch 4, dadurch gekennzeichnet , daß man das 4,8,8-Trimethyl-9-formyl-decahydro-1,4-methano- azulen einsetzt.11. Use according to claim 4, characterized in that the 4,8,8-trimethyl-9-formyl-decahydro-1,4-methano-azulene is used. 12. Verwendung nach Anspruch 4, dadurch gekennzeichnet , daß man das 4,8,8-Trimethyl-9-cyclohexanoyloxymethyl-deca- hydro-1,4-methano-azulen einsetzt.12. Use according to claim 4, characterized in that the 4,8,8-trimethyl-9-cyclohexanoyloxymethyl-deca- hydro-1,4-methano-azulene is used. 13. Verwendung nach Anspruch 4, dadurch gekennzeichnet , daß man das 4,8,8-Trimethyl-9-(2-cyano-2-äthoxycarbonyl-äthyl) -decahydro-1,4-methano-azulen einsetzt.13. Use according to claim 4, characterized in that the 4,8,8-trimethyl-9- (2-cyano-2-ethoxycarbonyl-ethyl) -decahydro-1,4-methano-azulene is used. 14. Verwendung nach Anspruch 3, dadurch gekennzeichnet , daß man das 8- oder 9-Hydroxy-tricyclo-[5.2.1.02,6]-decan; 8- oder 9,3,4-Trihydroxy-tricyclo-[5.2.1.02,6]-decan; 3- oder 4-Hydroxymethyl-tricyclo-[5.2.1.02,6]-decan und/oder 3- oder 4, 8- oder 9-Dihydroxymethyl- tricyclo[5.2.1.02,6]-decan einsetzt.14. Use according to claim 3, characterized in that the 8- or 9-hydroxy-tricyclo- [5.2.1.0 2,6 ] decane; 8- or 9,3,4-trihydroxy-tricyclo- [5.2.1.0 2,6 ] decane; 3- or 4-hydroxymethyl-tricyclo [5.2.1.0 2,6 ] -decane and / or 3- or 4, 8- or 9-dihydroxymethyl-tricyclo [5.2.1.0 2,6 ] -decane is used. 15. Verwendung nach einem der Ansprüche 1 bis 14, dadurch gekennzeichnet, daß man eine der beanspruchten Verbindungen oder eine Mischung aus zwei oder mehreren der beanspruchten Verbindungen einsetzt.15. Use according to one of claims 1 to 14, characterized in that one of the claimed compounds or a mixture of two or more of the claimed compounds is used. 16. Verwendung nach einem der Ansprüche 1 bis 15, dadurch gekennzeichnet, daß man die beanspruchten Verbindungen im Gemisch mit anderen Traktionsflüssigkeiten verwendet.16. Use according to one of claims 1 to 15, characterized in that one uses the claimed compounds in a mixture with other traction fluids. 17. Verwendung nach Anspruch 16, dadurch gekennzeichnet, daß man die beanspruchten Verbindungen in einer Menge von mindestens 5 Gew.-%, insbesondere mindestens 30 Gew.-% verwendet.17. Use according to claim 16, characterized in that the claimed compounds are used in an amount of at least 5% by weight, in particular at least 30% by weight. 18. Verwendung nach einem der Ansprüche 15 bis 17, dadurch gekennzeichnet, daß die Traktionsflüssigkeiten übliche Zusatzstoffe enthalten.18. Use according to any one of claims 15 to 17, characterized in that the traction fluids contain conventional additives. 19. Verwendung der in den Beispielen beschriebenen Verbindungen als Traktionsflüssigkeit.19. Use of the compounds described in the examples as a traction fluid.
EP82111051A 1981-12-30 1982-11-30 Traction fluid Expired EP0082967B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82111051T ATE29901T1 (en) 1981-12-30 1982-11-30 TRACTION FLUID.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813151938 DE3151938A1 (en) 1981-12-30 1981-12-30 TRACTION FLUID
DE3151938 1981-12-30

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EP0082967A2 true EP0082967A2 (en) 1983-07-06
EP0082967A3 EP0082967A3 (en) 1985-08-28
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0266848A2 (en) * 1986-11-06 1988-05-11 Shell Internationale Researchmaatschappij B.V. Ester compound lubricants
EP0361347A1 (en) * 1988-09-26 1990-04-04 Mitsubishi Oil Company, Limited Lubricating oil for traction drives
EP0402881A1 (en) * 1989-06-16 1990-12-19 Idemitsu Kosan Company Limited Process for improving the coefficient of traction.
EP0508292A1 (en) * 1991-04-08 1992-10-14 Idemitsu Kosan Company Limited Traction drive fluid, process for producing the same and bicyclo octane compound
EP0943599A1 (en) * 1998-03-20 1999-09-22 Clariant GmbH Terpene ethers and their uses
WO2003014268A1 (en) * 2001-08-08 2003-02-20 Idemitsu Kosan Co., Ltd. Fluids for traction drive
WO2005035699A1 (en) 2003-10-08 2005-04-21 Idemitsu Kosan Co., Ltd. Lube base oil and lubricating oil composition
RU2479626C2 (en) * 2007-06-25 2013-04-20 Идемицу Козан Ко., Лтд. Lubricating oil for continuously variable transmission
US20130123553A1 (en) * 2010-07-20 2013-05-16 Idemitsu Kosan Co., Ltd. Lubricating oil composition and lubricating oil composition for continuously variable transmission

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0660315B2 (en) * 1986-05-17 1994-08-10 新日鐵化学株式会社 Lubricating base oil composition and method for producing the same
JP4891469B2 (en) * 1998-07-01 2012-03-07 出光興産株式会社 Traction drive fluid
JP5759685B2 (en) * 2010-07-20 2015-08-05 出光興産株式会社 Lubricating oil composition
JP5816497B2 (en) * 2010-09-15 2015-11-18 出光興産株式会社 Lubricating oil composition for continuously variable transmission
EP3778834A4 (en) * 2018-03-27 2021-12-29 Idemitsu Kosan Co.,Ltd. Lubricating oil base oil, lubricating oil composition containing same, and continuously variable transmission using said lubricating oil composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE569756A (en) *
DE934889C (en) * 1952-08-02 1955-11-10 Ruhrchemie Ag Process for the preparation of esters and / or polyesters of the tricyclodecane series
US2879299A (en) * 1952-05-31 1959-03-24 Ruhrchemie Ag Dicyclopentadien derivatives
DE1806401A1 (en) * 1967-11-01 1969-06-19 Sun Oil Co Power transmission fluid for traction drives
DE2133584A1 (en) * 1970-07-06 1972-02-03 Sun Oil Co., Philadelphia, Pa. (V.St.A.) Hydrocarbons

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3411369A (en) * 1966-10-13 1968-11-19 Monsanto Co Tractive fluids and method of use
US3577361A (en) * 1968-05-22 1971-05-04 Monsanto Co Synthetic power transmission fluids
FR2085901B1 (en) * 1970-04-07 1974-03-08 Monsanto Co
US3652418A (en) * 1970-05-21 1972-03-28 Monsanto Co Tractive fluid compositions
JPS5336105B1 (en) * 1970-09-23 1978-09-30
GB1319031A (en) * 1971-01-12 1973-05-31 Sun Oil Co Traction drive fluids
CA1033708A (en) * 1974-02-19 1978-06-27 Monsanto Company Lubricants for roller contact bearings
US3925217A (en) * 1974-03-28 1975-12-09 Monsanto Co Lubricants for rolling contact bearings
DE2937521A1 (en) * 1978-09-19 1980-03-27 Nippon Oil Co Ltd HYDRAULIC FLUID FOR TRANSMISSION
DE3009848A1 (en) * 1980-03-14 1981-09-24 Bayer Ag, 5090 Leverkusen OLIGOISOBUTYLCYCLOHEXANE, METHOD FOR THE PRODUCTION AND USE THEREOF

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE569756A (en) *
US2879299A (en) * 1952-05-31 1959-03-24 Ruhrchemie Ag Dicyclopentadien derivatives
DE934889C (en) * 1952-08-02 1955-11-10 Ruhrchemie Ag Process for the preparation of esters and / or polyesters of the tricyclodecane series
DE1806401A1 (en) * 1967-11-01 1969-06-19 Sun Oil Co Power transmission fluid for traction drives
DE2133584A1 (en) * 1970-07-06 1972-02-03 Sun Oil Co., Philadelphia, Pa. (V.St.A.) Hydrocarbons

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0266848A2 (en) * 1986-11-06 1988-05-11 Shell Internationale Researchmaatschappij B.V. Ester compound lubricants
EP0266848A3 (en) * 1986-11-06 1988-10-05 Shell Internationale Research Maatschappij B.V. Ester compound lubricants
EP0361347A1 (en) * 1988-09-26 1990-04-04 Mitsubishi Oil Company, Limited Lubricating oil for traction drives
US5043497A (en) * 1988-09-26 1991-08-27 Mitsubishi Oil Co., Ltd. Lubricating oil for traction drives
EP0402881A1 (en) * 1989-06-16 1990-12-19 Idemitsu Kosan Company Limited Process for improving the coefficient of traction.
US5126065A (en) * 1989-06-16 1992-06-30 Idemitsu Kosan Co., Ltd. Process for improving the coefficient of traction and traction drive fluid
EP0508292A1 (en) * 1991-04-08 1992-10-14 Idemitsu Kosan Company Limited Traction drive fluid, process for producing the same and bicyclo octane compound
US5283384A (en) * 1991-04-08 1994-02-01 Idemitsu Kosan Co., Ltd. Traction drive fluid, process for producing the same and bicyclo octane compound
EP0943599A1 (en) * 1998-03-20 1999-09-22 Clariant GmbH Terpene ethers and their uses
US6395689B1 (en) 1998-03-20 2002-05-28 Clariant Gmbh Terpene ethers and their use
WO2003014268A1 (en) * 2001-08-08 2003-02-20 Idemitsu Kosan Co., Ltd. Fluids for traction drive
US7402715B2 (en) 2001-08-08 2008-07-22 Idemitsu Kosan Co., Ltd. Fluids for traction drive
WO2005035699A1 (en) 2003-10-08 2005-04-21 Idemitsu Kosan Co., Ltd. Lube base oil and lubricating oil composition
EP1672050A1 (en) * 2003-10-08 2006-06-21 Idemitsu Kosan Co., Ltd. Lube base oil and lubricating oil composition
EP1672050A4 (en) * 2003-10-08 2008-09-17 Idemitsu Kosan Co Lube base oil and lubricating oil composition
US7964540B2 (en) 2003-10-08 2011-06-21 Idemitsu Kosan Co., Ltd. Lube base oil and lubricating oil composition
RU2479626C2 (en) * 2007-06-25 2013-04-20 Идемицу Козан Ко., Лтд. Lubricating oil for continuously variable transmission
US20130123553A1 (en) * 2010-07-20 2013-05-16 Idemitsu Kosan Co., Ltd. Lubricating oil composition and lubricating oil composition for continuously variable transmission
EP2597140A1 (en) * 2010-07-20 2013-05-29 Idemitsu Kosan Co., Ltd. Lubricating oil composition and lubricating oil composition for continuously variable transmission
EP2597140A4 (en) * 2010-07-20 2014-11-26 Idemitsu Kosan Co Lubricating oil composition and lubricating oil composition for continuously variable transmission
RU2564027C2 (en) * 2010-07-20 2015-09-27 Идемицу Козан Ко., Лтд. Lubricating oil composition and lubricating oil composition for continuously variable transmission
US9156751B2 (en) 2010-07-20 2015-10-13 Idemitsu Kosan Co., Ltd. Lubricating oil composition and lubricating oil composition for continuously variable transmission

Also Published As

Publication number Publication date
DE3277377D1 (en) 1987-10-29
JPS58154799A (en) 1983-09-14
DE3151938A1 (en) 1983-07-07
EP0082967A3 (en) 1985-08-28
EP0082967B1 (en) 1987-09-23
JPS6144918B2 (en) 1986-10-04
ATE29901T1 (en) 1987-10-15

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