NL8103378A - PREPARATION SUITABLE FOR MECHANICAL ENERGY OR POWER TRANSMISSION AND METHOD FOR WORKING TRACTION DRIVES. - Google Patents

Description

* - 1 - * β '

Preparation suitable for mechanical energy or power transmission and method for operating traction drives.

The invention relates to a composition suitable for use in mechanical energy or power transmission units. In particular, the invention relates to compositions specially adapted for use in traction drives and to a method of operating traction drives.

Until now, gearboxes and hydraulic devices have been used for energy or power transmission and for speed control. Today, a system of drives, so-called traction drives (rolling friction drives) based on point contact or line contact between rolling solids, has found recognition. These traction drives are particularly suitable in industrial machines because they provide high energy or power transmission efficiency without the vibrations characteristic of installations using positive contact gearboxes and the like.

As the fluid to be used between the contacting parts of such traction drives, a lubricant should be selected which is most suitable from a functional point of view. In particular, the fluid present between the contacting parts must have the ability to undergo a reversible glass transition, with viscosity increasing and the efficiency of energy or force transmission between surfaces under high pressure in rolling contact is enlarged, and as soon as it comes out of the area where those surfaces come into contact, it immediately returns to its original, liquid state. It must also be able to prevent direct contact between metal bodies and 8103378 V '- - ----- - --- ..... ^ -2.- to prevent metal bodies from being damaged by seizing, wear and fatigue, and, like lubricants of all kinds, perform the important functions of preventing rust from occurring and the temperature rising or becoming too high.

Friction or traction drive devices for the transmission of mechanical energy or power have been described in a number of technical publications. For example, they are described in detail in U.S. Patent Nos. 3,394,603 and 3,411,369, the Journal of Chemical and Engineering Data, Vol. 5, no. 4, pp. 499-507 (1960) by Hewko et al in Proceedings of the Symposium on Rolling Contact Phenomena, pp. 157-185 (1962), Elsevier, Amsterdam, The Netherlands.

A wide variety of materials have been proposed as preparations for use in traction-drive, including mineral oils (Japanese Patent Publication 24,635 / 1964), mixtures of dialkyl aromatic hydrocarbons with diarylalkanes (Japanese Patent Publication 40,525 / 1972), polymethyl methacrylate (Japanese Patent Publication 31,828 / 1973 ), 20 adamantanes (Japanese Patent Publications 42,067 / 1973 and 42,068 / 1973), polyolefins (Japanese Patents KOKAI 4,766 / 1971 and 2,229 / 1972) and alkyl naphthalenes (U.S. Patent 2,549,377). Japanese patent KOKAI 40.726 / 1980 has proposed liquids obtained by hydrogenating bis- (a-methylbenzyltoluene) and / or bis- (a-methylbenzyl) xylene.

In addition, proposals have also been made that relate to naphthene oils with naphthene rings.

These naphthene oils include, for example, dicyclohexylethane 30 (U.S. Patent 3,577,361), dicyclohexylpropane (Japanese Patent Publication 36,105/1978), hydrogenated condensed ring compounds (U.S. Patent 3,411,369), naphthenes with at least one saturated carbonaceous cyclic ring (U.S. Patent 3,440,894), 35 naphthenes with at least two saturated carbon-containing cyclic rings (U.S. Patent 3,925,217) and 8103378-3 - mixtures of naphthenes and paraffins (U.S. Patent Nos. 3,595,796 and 3,595,797) as well as an oil which is obtained by hydrogenating the product of the alkylation of xylene and / or toluene with styrene (Japanese Patent 5 KDKAI 43108/1980).

The above-mentioned U.S. Patents 3,440,894 and 3,925,217 include a wide variety of naphthene compounds and, for example, mention a large number of naphthenes. Most of these are compounds 10 which have one or two hydrogenated rings. Among the listed compounds, only a limited number have three or more hydrogenated rings, including tercyclohexyl compounds, for example, 1,2,3-tricyclohexylpropane and tricyclohexylmethane. Although they have a high traction factor, they are not very suitable for practical use, due to the high viscosity or high crystal precipitation temperature.

The prior art technical literature shows that naphthene oils containing hydrogenated rings generally have excellent lubricating properties, in particular properties favorable for use in traction drives.

The object of the invention is now to provide new preparations which are suitable for use in mechanical energy or power transmission devices. Another object of the invention is to provide such compositions which excel in traction properties and other properties such as oxidation resistance and corrosion resistance and which can be readily synthesized commercially from inexpensive starting materials. Yet another object of the invention is to provide a new method of operating traction drives.

The above objectives are achieved by providing a formulation suitable for use in mechanical energy or power transmission units -35 consisting essentially of a small amount of an antioxidant mixed with a hydrocarbon oil consisting of 8103378 * - 4 - bonds of 19-30 carbon atoms and with three 6-membered carbocyclic rings, consisting of a mixture of compounds of the formula 1, wherein Rj is a divalent straight or branched group C in which y is an integer of 1 t / m 3, R2 represents a group 5 ^ z®2z with a straight chain in which z is an integer from 1 to 3, R ^, R ^ and R ^ represent equal or different alkyl groups with 1 t / m 4 carbon atoms, 1, m and n each represent an integer from 0 to 3 and x is 0 or 1 and in which rings A and B are hydrogenated benzene rings and ring C represents a hydrogenated benzene ring if x is 1 and a hydrogenated benzene ring or a cyclohexane ring if x is 0, where the hydrogenated benzene rings are saturated with hydrogen for at least 80% but less than 100% of the theoretically possible degree of saturation and this hydrocarbon oil is otherwise unsaturated. The rings are preferably at least 95% saturated.

In one embodiment of the invention, x in the formula is preferably 1; in another embodiment, x is preferably 0. Preferred compounds in those cases include hydrogenated 1- (benzylphenyl) -1-phenylethane with 0 to 2 methyl substituents and 0 to 2 ethyl substituents, hydrogenated dibenzylbenzene with 0 to 2 methyl substituents and. 0 to 2 ethyl substituents, hydrogenated benzyl biphenyl having 0 to 2 methyl substituents and 0 to 2 ethyl substituents and hydrogenated 1-biphenyl-1-phenylethane with 0 to 2 methyl substituents and 0 to 2 ethyl substituents.

Advantageously, the preparation also contains up to 100 parts, preferably 10 to 60 parts of an alkylcyclohexane in which the alkyl group contains 9 to 20 carbon atoms, for every 100 parts of the said hydrocarbons.

The invention also relates to a method of operating a traction drive having an area with point or line contact between rolling solids and wherein the contact area is lubricated or oiled with a composition as described above.

8103378 / * - 5 -

It has been found that a mixture of backbone hydrocarbons in which three hydrogenated benzene rings are linearly connected by two chains CyH2y and two hydrogenated benzenes are directly connected linearly by a CyH2y group and a hydrogenated benzene or cyclohexane ring directly One of the hydrogenated benzene rings is attached without an intermediate linking group, because of its particular molecular structure, is particularly effective in accomplishing the object of the present invention.

The main component of the hydrocarbon oil of the invention for use in mechanical energy or power transmission devices is a naphthenic hydrocarbon compound having 19-30 carbon atoms and having 3 hydrocarbon 6-rings represented by the aforementioned formula 1 wherein y and z are in the groups R 1 and R 2 individually are 1, 2 or 3 and y is preferably 1 or 2 and z is preferably 1 and wherein R 1, R 1 and R 1 separately represent alkyl groups having 1 to 4 carbon atoms, preferably with 1 or 2 carbon atoms and 1, m and n separately are 0, 1, 2 or 3 or preferably 0.1, 2 or 3 and most preferably 0, 1 or 2 and x is either 0 or 1.

If x is 1, the compound of general formula 1 can be represented by general formula 2. If x is 0, this compound can be represented by formula 3. In these formulas, Rj, R2, R ^ »R ^, R ^, 1, m and n the aforementioned meanings and ring G in formula 3 is a hydrogenated benzene ring or cyclohexane ring.

Compounds of general formula 1 wherein x is 1 include hydrogenated dibenzylbenzenes, hydrogenated (methylbenzyl) benzylbenzenes, hydrogenated (dimethylbenzyl) benzylbenzenes, hydrogenated di- (methyl-benzyl) -benzenes, hydrogenated (ethylbenzyl) -benzylbenzenes - (ethylbenzyl) -benzenes, hydrogenated (diethylbenzyl) -benzylbenzenes, hydrogenated dibenzyltoluenes, hydrogenated dibenzyl-dimethylbenzenes, hydrogenated dibenzyl-ethylbenzenes, hydrogenated (methylbenzyl - dimethylbenzyl- 8103378) -benzyltoluenes, hydrogenated (ethylbenzyl) -benzyltoluenes, hydrogenated di- (methylbenzyl) toluenes, hydrogenated di- (ethylbenzyl) -toluenes, hydrogenated di- (methylbenzyl) xylenes, hydrogenated 1-l- (benzylphenyl) -phenyl-phenyl) -phenyl-phenyl 1.1- / (methylbenzy1) -phenyl-7phenyl-ethanes, hydrogenated 11- (benzyl-phenyl) (methylphenyl) -ethanes, hydrogenated 11- (benzyl-methyl phenyl) -phenylethanes, hydrogenated 1,1- (benzylphenyl) - (ethylphenyl) ethanes, hydrogenated 1,1- (benzylethylphenyl) -phenylethan-10, hydrogenated phenethyl-benzylbenzenes, hydrogenated phenethyl-benzyltoluenes, hydrogenated diphenethylphenethylenophenethylene.

Among the aforementioned compounds represented by the general formula II are the hydrogenated dibenzylbenzenes and hydrogenated (benzylphenyl) phenyl ethanes or their derivatives with 1 to 2 methyl or ethyl substituents, especially hydrogenated dibenzyl toluene, especially suitable for the purpose of the invention.

The compounds represented by the general formula I, wherein x is 0, include hydrogenated benzyl biphenyls, hydrogenated benzyl mono methyl biphenyls, hydrogenated benzyl dimethyl biphenyls, hydrogenated benzyl trimethyl biphenyls, hydrogenated benzyl monoethyl biphenylen, diet biphenyls, hydrogenated benzyltriethyl-biphenyls, hydrogenated biphenylyltolylmethanes, hydrogenated (methylbiphenylyl) tolylmethanes, hydrogenated (dimethylbiphenylyl) tolyl-methylphenyl (tolynyl) tolylmethanes (methyl) tolylmethanes) hydrogenated (biphenylyl) (ethylphenyl) ethanes, hydrogenated (methylbiphenylyl) (ethylphenyl) methanes, hydrogenated (dimethylbiphenylyl) (ethylphenyl) methanes, hydrogenated (trimethylbiphenylyl) (ethylphenyl) methanes, ethylenylphenyl (ethyl) biphenyl) -35-ned (diethylbiphenylyl) (ethylf enyl) methanes, hydrogenated 1-biphenylyl-1-phenyl ethanes, hydrogenated 1- (methylbiphenylyl) - 8103378 é - 7 - 1-phenylethanes, hydrogenated 1- (dimethylbiphenylyl) -1-phenylethanes, hydrogenated 1- (ethylbiphenylyl) 1-phenylethanes, hydrogenated 1- (diethylbiphenylyl) -1-phenylethanes, hydrogenated l-biphenylyl-1- (methylphenyl) ethanes, hydrogenated 5l- (ethylbiphenylyl) -1- (methylphenyl) ethanes, hydrogenated 1- (methylbiphenylyl) - (methylphenyl) ethanes, hydrogenated 1-biphenylyl-1- (ethylphenyl) ethanes, hydrogenated 1- (methyl-biphenylyl) -1- (ethylphenyl) ethanes, hydrogenated 1- (dimethyl-biphenylyl) -1- (ethylphenyl) ethanes, hydrogenated L- (ethylbi-10 fenylyl) -L- (ethylphenyl) ethanes, hydrogenated fenethylbi- phenyls, hydrogenated phenethyl-methylbifenylen, hydrogenated phenethyl-dimethylbifenylen, hydrogenated phenethyl-ethylbifenylen, hydrogenated phenethyl-diethylbifenylen, hydrogenated (methylphenethyl) biphenyls, hydrogenated 15 (methylphenethyl) -methyl biphenyls, g ehydrogenated (methylphenethyl) ethyl biphenyls and hydrogenated (ethylphenethyl) biphenyls.

Among the above compounds of general formula 3, the hydrogenated benzyl biphenyls or derivatives thereof containing one or two methyl or ethyl substituents are particularly suitable for the purpose of the invention.

The compounds of the general formula II, for example the hydrogenated dibenzylbenzenes, are obtained by hydrogenating dibenzylbenzene obtained in the reaction of benzyl halides with benzene in the presence of a Friedel-Crafts catalyst. Of the benzyl halides, benzyl chloride appears to behave most favorably again. Advantageously, the benzyl halides are used in an amount of not more than 1 mole, preferably 0.1 to 0.5 mole, per mole of benzene.

Of the various compounds suitable as Friedel-Crafts catalyst, sulfuric acid, boron trifluoride and aluminum chloride have proved particularly suitable, with aluminum chloride being considered the best choice. The amount of aluminum chloride to be used is preferably in the range of from 0.0001 to 0.1 mole per mole of benzyl chloride.

8103378

♦ Q

- 8 -

Although the reaction temperature can be selected in the range of 20 to 150 ° C, it is preferred to choose the temperature in the range of 40 to 80 ° C. Although it is sufficient if the reaction pressure is just above the minimum level required to keep the reactor contents in a liquid phase, an overpressure of 0 to 100 kPa appears to be beneficial for the reaction. This reaction produces dibenzyl benzene as a product in the form of a mixture of the ortho, meta and para isomers. These isomers can be hydrogenated as a mixture or can be hydrogenated separately. In preparation for hydrogenation, the Friedel-Crafts catalyst is removed from the reaction mixture, for example, by washing with water, and the unreacted portion of the reactants and any by-products of the reaction are expelled from the reaction mixture, for example, by distillation about the dibenzylbenzene to isolate. The isolated reaction product is then subjected to hydrogenation treatment in the presence of a hydrogenation catalyst.

As a hydrogenation catalyst, a platinum, palladium, rhodium, ruthenium or nickel catalyst is completely satisfactory. The nickel catalyst is used in an amount ranging from 0.1 to 20% by weight. The hydrogen pressure is suitably in the range of from 200 to 2100 kPa. The hydrogenation hydrogenation is used in an amount of 9 moles or more per mole of dibenzylbenzene, and preferably in an amount of 1.1 times the above molar ratio. The hydrogenation reaction temperature is in the range of from 100 to 200 ° C, preferably between 140 and 170 ° C. When the hydrogenation has proceeded to a certain degree of hydrogenation, the reaction is stopped and the hydrogenated dibenzylbenzene is isolated. This isolation of the reaction product can be achieved by simply removing the spent catalyst.

This can be done by filtration or optionally by any other conventional lubricant treatment method, eg dry clay treatment with active clay. If necessary, 8103378 τ * * - 9 - distillation can also be used for this purpose. However, distillation is generally of little benefit unless the reaction has yielded low-boiling compounds as by-products, since distillation of fully hydrogenated dibenzylbenzene and partially hydrogenated dibenzylbenzene or separation in the isomers is only very difficult.

The preparation of an alkyl-substituted hydrogenated dibenzylbenzene is accomplished by replacing the benzene or the benzyl halide or both with an alkyl-substituted benzene or alkyl-substituted benzyl halide or both as starting materials and using these starting materials in suitable combinations. Suitable alkyl substituted benzenes for this purpose are toluene, ethylbenzene, propylbenzene, xylene, cumene, diethylbenzene and methyl ethylbenzene. Suitable alkyl-substituted benzyl halides for this purpose include derivatives of benzyl halides containing a monomethyl or monoethyl substituent. If such alkyl-substituted starting materials are used, the reaction can be carried out under similar conditions as described above and the hydrogenation can be carried out in a similar manner.

When a compound of the general formula 4 (wherein and 1 have the meanings mentioned here and X represents a halogen atom) is used instead of the above benzyl halides or an alkyl-substituted derivative thereof, hydrogenated diphenethylbenzene or an alkyl substituted derivative thereof.

According to a preferred embodiment of the process for the preparation of the compounds used according to the invention, a hydrogenated compound of the type (benzylphenyl) -phenylalkane is obtained by reacting a diphenylalkane with benzyl halides in the presence of a Friedel-Crafts catalyst to obtain a (benzyl-phenyl) -phenylalkane and then hydrogenating this reaction 8103378

♦ Q

- 10-t product. In this case, when an--diphenyalkane is used as the diphenylalkane, a hydrogenated compound of the type 1- (benzylphenyl) -1-phenylalkane is obtained. Use of an alkyl-substituted 1,1-diphenylalkane or an alkyl-substituted benzyl halide or both results in the formation of a hydrogenated compound of the alkyl-substituted 1- (benzylphenyl) -1-phenylalkane type.

When a 1,3-diphenylalkane is used as diphenylalkane, a hydrogenated compound of type 10 1- (benzylphenyl) -3-phenylalkane is obtained and when a 1,2-diphenylalkane is used, a 1-benzylphenyl-2-phenylalkane or a 2-benzylphenyl -1-phenylalkane. In all these cases, the type of Friedel-Crafts catalyst, the conditions of the Friedel-Crafts reaction for alkyl halides, the conditions of hydrogenation, etc., are similar to those described above.

The above 1,1-diphenylalkanes can be obtained by reacting ethylbenzene or styrene with benzene in the presence of the Friedel-Crafts catalyst.

The compound of the general formula 3, such as, for example, hydrogenated benzyl biphenyl, are obtained in a manner similar to the compound of the general formula 2, by hydrogenation of benzyl biphenyls which are formed in the reaction of benzyl halides with biphenyls in the presence of the Friedel-Crafts catalyst. . In this case, the amount of aluminum chloride used is preferably in the range from 0.0001 to 0.05 mole per mole of benzyl chloride. Although the reaction temperature can be selected in the range from just above the melting point of the respective bi-phenyls to 180 ° C, the reaction temperature is preferably selected in the range from 70 to 100 ° C. Although the reaction pressure need only be just high enough to keep the reactor contents in a liquid phase, preference is given if the pressure is in the range of 100 to 600 kPa. This reaction yields a product of benzyl biphenyl, ie a mixture of ortho, meta and para isomers thereof.

8103378 - 11 -

These isomers can be either mixed subjected to hydrogenation or separately. * In preparation for hydrogenation, the reaction mixture is washed with water and distilled to remove the unreacted reagents and the Friedel-5 Crafts catalyst used and isolate benzyl biphenyl. The isolated benzyl biphenyl is then hydrogenated by introducing hydrogen in the presence of a hydrogenation catalyst. In this case, the hydrogenation conditions are the same as those used in the hydrogenation of the compound of general formula II.

The preparation of a hydrogenated alkyl substituted benzyl biphenyl compound is accomplished by replacing the biphenyl or benzyl halide or both with an alkyl substituted biphenyl or an alkyl substituted benzyl halide or both as starting materials and using those starting materials in suitable combinations. Suitable alkyl-substituted biphenyls are monomethyl biphenyl, monoethyl biphenyl, monopropyl biphenyl, dimethyl biphenyl, diethyl biphenyl and methyl ethyl biphenyl. Suitable alkyl-substituted benzyl halides are derivatives of benzyl halide bearing monomethyl, monoethyl or other similar substituents. When these alkyl substituted derivatives are used, the reaction can be carried out under conditions similar to those described above. The hydrogenation can also take place in a similar manner.

When a compound of the general formula 4 wherein and 1 have the aforementioned meanings and X represents a halogen atom is used in place of the above benzyl halides or an alkyl-substituted derivative thereof, hydrogenated phenethyl-biphenyl or an alkyl-substituted derivative thereof.

Another preferred embodiment of the process for the preparation of the compounds to be used according to the invention comprises the steps of reaction of cyclohexylbenzene or a biphenyl with styrene in the presence of the 81 0 3 3 7 3 »- 12 -« · \

Friedel-Crafts catalyst and hydrogenation of the resulting reaction product. Suitable Friedel-Crafts catalysts for this reaction are boron trifluoride, aluminum chloride and sulfuric acid. When sulfuric acid is used as a catalyst, the amount of this catalyst is preferably in the range of 5 to 50% by weight, based on the amount of the biphenyl compound used. The cyclohexylbenzene or biphenyl compound and the styrene are preferably used in equal or substantially equal molar amounts to exclude the otherwise possible polymerization of styrene in the reaction. The reaction temperature is preferably low on the order of 0 to 30 ° C. When the reaction is complete, the reaction mixture is washed with water to remove the spent catalyst and then distilled to isolate 1- (biphenylyl) -1-phenylethane or 1- (cyclohexyl-15-phenyl) -1-phenylethane as reaction product.

The compound, when subjected to hydrogenation in the same manner as described above, yields hydrogenated 1- (biphenylyl) -1-phenylethane.

If such a process is repeated using an alkyl-substituted cyclohexylbenzene or an alkyl-substituted biphenyl or an alkyl-substituted styrene in place of the cyclohexylbenzene or biphenyl or styrene, an alkyl-substituted hydrogenated 1- (biphenylyl) -1-phenylethane.

Cyclohexylbenzene compounds which are suitable for this purpose are alkyl-substituted cyclohexylmethylbenzenes, cyclohexylethylbenzenes, cyclohexylpropylbenzenes, cyclohexyldimethylbenzenes, cyclohexyldiethylbenzenes, (methylcyclohexyl (benzene)), (dimethylbenzenes), (dimethylbenzenes), (dimethylbenzenes) and mixtures thereof. Alkyl substituted diphenyl compounds suitable for use herein are the same as mentioned above. Suitable alkyl-substituted styrene compounds include compounds of the general formula 5, wherein R 1 and 1 have the meanings mentioned. A typical example of such compounds is vinyl 8103378 9% - 13 - toluene. Also α-methystyrene can be used in a similar manner with advantage. When these alkyl-substituted derivatives are used, the reaction can be carried out under conditions similar to those described above.

The composition according to the invention for use in mechanical energy or power transmission devices can be used as such. When it is mixed with an alkyl (C8 -C18) cyclohexane which is added to it in an amount of up to 100 parts by weight, preferably in an amount of from 10 to 60 parts by weight based on 100 parts by weight of the preparation according to the invention, a preparation can be obtained which has a varying degree of viscosity and which is suitable for use in mechanical energy or power transmission devices without substantially deteriorating the properties that the oil must have in order to perform this function. . Alkylcyclohexanes suitable for this purpose are obtained by hydrogenating alkylbenzenes obtained by reacting the propylene trimer to form propylene pentamer with benzene.

The compositions according to the invention may contain, in addition to the essential ingredients, namely a small amount of an antioxidant and a hydrocarbon oil as described above, other additives or by-products, provided that these do not affect the utility in mechanical energy or power transmission systems . For example, in addition to antioxidants, the compositions may contain additives such as anti-rust agents, anti-foaming agents, and the like.

They may also contain a small amount of the by-product and are formed during the preparation of the hydrocarbon oils of general formula 1. However, a large amount of aromatic hydrocarbons or double bond compounds should preferably be avoided. In the preparation of a compound of the general formula 1 by hydrogenating a corresponding aromatic hydrocarbon, the hydrogenation is therefore preferably continued to the extent that the hydrogenation degree is at least 80% of the maximum attainable, preferably 8103378 4 - 14. % and preferably more than 95% of the maximum achievable hydrogenation degree. Practically complete hydrogenation, for example removing the unsaturation to less than 1%, is practically impossible. However, such a complete removal of unsaturation is also not necessary because the objects of the invention are not contradicted by the presence of small amounts of unsaturated compounds. The hydrocarbon oils containing the essential components of the compositions of the invention are in practice mixtures of 10 components at different stages of hydrogenation or isomers or both and may be used as such or in combination with the appropriate additive as set forth above .

The term hydrogenated compounds should therefore be understood to mean such compounds which have been hydrogenated for at least 80% and preferably for at least 95% of the theoretical possible hydrogenation degree, calculated on the mixture.

The traction coefficient of a given oil is generally measured by means of a traction drive device. In the present invention, this measurement is performed with a four-roll machine friction tester from Soda (see T. Kimura and M. Muraki, "Tribology", 1979 (12), 255).

In this tester, traction (rolling friction) occurs in the three contact areas formed between an inner centrally located roller and three outer rollers arranged tangentially around the inner central roller. These rollers are positioned so that equal loads act perpendicular to the three contact surfaces. The surface contact pressure, expressed in the average Hertz pressure, is in the range of 0.575 to 1.157 GPa. The other conditions for determining traction with this tester are listed in Table A.

35 8103378 - 15 -

Table A

Traction determination conditions Rotation speed 1.05 to 4.19 m / s

Slip 0 to 0.22 m / s 5 Test rolls Material army steel, SUJ-2

Hardness (Hv) 760 to 800

Dimensions 40 mm x 9 mm (outer rolls) (diam. X wide - 40 mm x 5 mm (central 10 te) roll)

Lubrication method - dripping approx. 10 ml / min

Oil temperature 28 ° C

The test procedure included: first adjusting the center and outer rollers to rotate at a fixed speed; applying a load to these rollers and then accelerating the rotational speed of the outer rollers while keeping that of the central roll constant, creating a slip / roll ratio that allows continuous measurement of the change in the frictional torque or traction coefficient. The frictional torque was determined by directly measuring the torque of the non-army supported shaft of the central roller with a tension gauge tension gauge.

The traction coefficient determined under said conditions will generally first increase linearly with increasing slip / roll ratio and then peak and begin to decrease. From the point of view of the practical use of lubricating oil, the most important zone of the curve thus drawn lies in the first part of the straight line where the amount of heat generated by the shear forces (slip) in the oil layer is not yet large. Hereafter, therefore, only the traction coefficient in this area will be considered.

Under the test conditions of, for example, an average Hertz pressure of 1.157 GPa and a rotation speed of 4.19 m / s, the following traction coefficients were obtained: 8103378 - 16— *

Viscosity (est) Traction-at 40 ° C_ coefficient

Naphthenic mineral oil 8.0 0.050

Hydrogenated polyisobutene 10.0 0.060 Dicyclohexane 2.9 0.065

Ethyldicyclohexane 4.0 0.060

Methylcyclohexyl-

Cyclohexylmethane 4.2 0.065

Dicyclohexylethane 4.0 0.070 10 sec-dodecylcyclohexane 5.4 0.050

Tercyclohexyl Compounds (mixtures of o and m) 0.090

Hydrogenated linear dimer of α-methylstyrene 22 0.090 15 x Crystals precipitated at room temperature,

In contrast, the traction coefficient of the preparation according to the invention was 0.095, a value clearly higher than the values found with the aforementioned hydrocarbons. It has therefore been found that the product of the invention outperforms even hydrogenated linear dimer of α-methylstyrene which is now on the market as a very good synthetic traction fluid.

In addition to a good traction coefficient and a good resistance to oxidation, a preparation for mechanical energy or power transmission must also have at least a pour point or freezing point of -10 ° C and preferably a viscosity at 40 ° C under atmospheric pressure of 7 to 150 est.

Viscosity (est) Pour point or 30 at 40 ° C - freezing point (° C) o-tercyclohexyl compound - 45 m-tercyclohexyl compound - 63 p-tercyclohexyl compound - 162 mixture of m- and p-tercyclo crystals hexyl compounds precipitated at room temperature tricyclohexylmethane - 59 1.1.3-tricyclohexylpropane ca 2500 8103378 Λ - 17 -

As is apparent from the foregoing, the above compounds are not suitable as a base oil for a mechanical energy or power transmission formulation.

Furthermore, to ensure stable operation of a traction device for a long time, the mechanical energy or power transmission preparation must have good sealing properties. The following table shows the sealing properties of a mechanical energy or power transmission formulation using base oils of suitable viscosity and relatively good traction properties. The tests were performed at 120 ° C for 70 h with nitrile rubber (Buna N) and acrylic rubber, according to a method from JIS K-6303.

15 _Basic oil_

Examples I and IV Oil for traction drive on the basis of hydrogenated α-methyls tyrene-_-dimer_ _Rubber_

Ni vibr- Acrylic- Nitrile- Acrylic rubber rubber rubber rubber

Property_ (Buna N) (Buna N) _ 25 Weight gain (%) 3.45 1.48 7.30 3.86

Volume increase (%) 6.58 3.42 13.6 7.67

Tensile strength (MPa) 19.5 8.1 16.8 8.5

Rack (Z) 260 140 150 110

Variation in hardness (Z) -6 0 -6 -1

30 Aniline tip 85 ° C 70 ° C

The oil according to the invention can be used as such, but additives are preferably included.

In addition to the traction properties described above, the oil for use in a traction drive must also have properties as would normally be expected from ordinary lubricants such as, for example, oxidation resistance, corrosion resistance 8103378-18 improving the viscosity index, wear resistance, anti-rust properties, a certain swelling effect on rubber and the ability to prevent slipping. Therefore, depending on the intended application, suitable additives may be included, for example, 2,6-di-tertiary-butyl paracresol and other similar alkyl phenols, zinc dialkyl dithiophosphate and other similar sulfur phosphorus compounds such as antioxidants, amines, esters and metal salts as anticorrosive agents, polymethacrylates as agents for improving the viscosity index and silicone polymers as anti-foaming agents.

The invention will now be further described with reference to the following exemplary embodiments.

In the following examples, a composition suitable for use in traction drives was prepared by adding 2,6-di-tertiary-butyl-p-cresol and zinc dialkyldithiophosphate to hydrogenated dibenzyltoluene or a similar oil according to the invention. antioxidants, each in an amount of 0.5% by weight. The traction coefficient of this oil was determined under the aforementioned conditions and the oil was then subjected to an oxidation test according to the method described in section 3.2 (test method for the oxidation resistance of machine oil for internal combustion engines) from the Japanese Industrial Standard. (JIS) 25 K-2514-1980 (Test method for the oxidation resistance of lubricating oils).

Example I

0.002 to 0.01 parts of aluminum chloride was added to 3 parts of toluene. The mixture was heated to 70 ° C and then it was reacted for 2 h with 1 part of benzyl chloride added to it. The reaction mixture was washed with water to remove the spent catalyst and then distilled to remove the unreacted portion of the reagents. The dibenzyl-35 toluene (mixture of isomers) thus obtained was placed in an autoclave and, in the presence of a nickel catalyst, hydrogenated for 4 h 8103378-19 - under the following conditions: initial hydrogen pressure 4100 kPa, temperature 200 ° C, to hydrogenate the dibenzyltoluene (mixture of the isomers). The general properties of this hydrogenated dibenzyltoluene are shown in Table B.

The results of the oxidation test were as reported in Table C. For comparison, a commercially available traction drive oil based on hydrogenated linear α-methylstyrene dimer and an oil prepared from a naphthenic mineral oil was subjected to the same tests.

The oxidation test was conducted under the following conditions:

Quantity of test sample 300 ml

Temperature 165.5 ° C

Duration 72 h 15 Oxidation catalyst Copper and iron

Example II

0.001 to 0.005 gmoles of aluminum chloride were added to 4 gmoles of 1,1-diphenylethane. The mixture was heated to 60 ° C and then allowed to react for 20 min with 1 µmole of added benzyl chloride. The reaction mixture was then washed with water to remove the spent catalyst and distilled to remove the unreacted portion of the reagents. The isolated 1- (benzylphenyl) -1-phenylethane (mixture of isomers) was placed in an autoclave and hydrogenated in the presence of a nickel catalyst under the following conditions: initial hydrogen pressure 10100 kPa; temperature 140-170 ° C, duration 5 h, yielding hydrogenated 1- (benzylphenyl) -1-phenylethane (mixture of isomers). The general properties of this reaction product were as reported in Table B.

This product, mixed with additives as described above, was tested to determine the traction coefficient and subjected to the oxidation test according to section 3.2 of JIS K-2514-1980. The results are shown in Table G.

8103373 - 20 -

Example III

A mixture of hydrogenated monoethyl-substituted 1- (benzylphenyl) -1-phenyl-ethane or compounds of formulas 6 and 7 was prepared according to the procedure of Example 2 except that 4 µmoles of monoethyl-substituted 1,1-diphenylethane were used instead of the 1.1 di-phenylethane. The general properties of this reaction product are shown in Table B. This product, after being mixed with additives in the manner described above, was tested to determine the traction coefficient and subjected to the oxidation test according to section 3.2 of JIS K-2514- 1980.

The results are shown in Table C.

15 8103378 - 21 - ra ö Λ 3 g ra g »c‘ d

m Q) i-n <M

3 rj o CM Γ * t>.

* ZL + j ra ·> · * “* S 'm -r) o 00 era m l ό« S ^ o M H-i »3 0

d <U I

0 <1) - 1 M

e o i «

Τί · Η Η H JL jL it L

u 4J bs <D * ra ra d jz j * w o a aj-QcuCTi ra w ^ p w dd'peo ^ tnmp o g · w «η g | OH »B» »P ° 2 S’ ¢ 0 ji> 1 o ov £ 3 <i-q I oo Η λα S * 5 ij

2 “S ί;" ϊ * "" -S3 S

»£« a S> Mfg <* oo «

S 'S'iS 3 0-ï-> g3 * HO <NK | - <N

«Wl 2> · Η d Τ3" ""

ewe, 3 3> *? L ° - OO

^ <U Ό W d

• H d ® 0) Φ i — 1 CÖ * H O O

O ra ra d H

1 p H

-JL 3 H

A I rH

ra>, d ^ · raai σ \ oo co co d ff ra - * o ra ° ° ° - ra ra ra ow ra g * g f-Γ— no d bom .d σ \ O m vo ë g * g ° oo

OOHiJ »0« «l„ P2 I

d.M ^ cuoi-ivor'.oco "g ° {P, N H PO Cö O 'W> j

cd >> d >> d - I J5 I

& »D ra d ra 'O

ra ra, Q ra γ-j S ’ra O '* -y Ή rü S ö fd d n ° H!

i — l 60 i S 2 I

| ö%> 3 «o O EO P

Hg ί ϋΐ ° - - ~ T3 ld · β * w> § ÖO Ό O I-J g o i — i i-ι <u ra ra g <* S η ί § ° S ra 00 22! d ü0i- (** o * _ o 'g .¾ o ^ oovomocMCT », .2 * öo UN rHVO OJ ΙΛ 0 \ P <D -Cf λλιιλι -fid ui— d, n σ> co Ό <nj ra SI 1 J 1 ° - ° - ° - "i <S: 3 3 uo => - oo | *, öo λ £> ί o ïï jg JQ) jg ·

o I O

rj ü «Η I · Η

o O ^ I * <u I W

o o 6 ^ ra öo i ra o i ra o o ^ ^ · η ö ra μ μ I · β

n 4J-H W5 I

^ v- / OO O + J * ÜM * 0 <ÜIH

wcö S ö 3J3C0-HIO

CÖ Μ Φ Q 3 O · Μ I

η -π ·? Ν, 7ί2! 2 ra m d & 0 rag! 12 ^ ww ^ p.00 M-) cp> g ÖO CM I w ri orad ma) ra ratooi * h o 4J 4J o öo «h jq) 04-i * pexj ira ο. .ί! .η dpo Pp oo dra ip ra * ^ 3 <! rara «nra ί-» ia · ϊ — ί> j 4_j 4-j ë ti 10) · Ρ ra i ra ü 2 .Η · Η · Η d I ra 0) -H -rl ra ÖO + J <U om CH «M 3 S m .ri * J ra e S Ρ- ·· -ι 6 * 61 ra ra 2ooo, 2o rnrao ra ^ ra p · ι m Q | Ü) Ü U 4-1 i>! - <· Η öó o-urararaw-ü f S3 S1 ^ f-2SJ ^

• Η · -Η -Η -H -r) d >> ij 2 S 2 Yy M

Pd coó >> 00! E h o> H W h m ί * 8103378.-22-

Example XV

0.001 to 0.005 parts of aluminum chloride were added to 5 parts by weight of biphenyl. The mixture was heated to 70 ° C and then it was reacted for 20 minutes with 5 1 parts by weight of benzyl chloride which were added. The reaction mixture was washed with water to remove spent catalyst and then distilled to remove the unreacted fractions of the reagents. The benzyl biphenyl (a mixture of isomers) formed was autoclaved with an internal volume of 1 liter and, in the presence of a nickel catalyst, hydrogenated under an initial hydrogen pressure of 100-100 kPa at 140-170 ° C for 2 hours. This gave hydrogenated biphenyl (a mixture of isomers). The general properties of this hydrogenated benzyl biphenyl are reported in Table D.

This product, mixed as described above with 0.5 wt% of 2,6-di-tertiary-butyl-p-cresol and 0.5 wt% zinc dialkyldithiophosphate as antioxidants was tested for its traction coefficient and subjected to the oxidation test according to paragraph 3.2 of JIS K-2514-1980. The results are shown in Table E.

Example V

A hydrogenated benzyl-monoethyl biphenyl, a mixture of formulas 8 and 9 was prepared according to the method of Example IV except that 5 parts by weight of monoethyl biphenyl and 0.03 parts by weight of aluminum chloride were used. The general properties of this reaction product are shown in Table D.

This product, mixed with other components as described above, was tested for the traction coefficient and subjected to an oxidation test according to section 3.2 of JIS K-2514-1980. The results are shown in Table E.

Example VI

1 liter of cyclohexyl benzene and 200 ml of concentrated hydrochloric acid were placed in a reactor, after which the mixture was kept at 15 ° C. Then, 800 ml of a 1: 1 mixture of cyclohexylbenzene and styrene were added dropwise to the mixture over 2 hours over the course of 2 hours while keeping the temperature of the mixture between 15 and 20 ° C. At the end of the dropwise addition of this mixture, 200 ml of concentrated sulfuric acid were added to continue the reaction for an additional 30 minutes. The reaction mixture was then repeatedly washed with water to remove residual sulfuric acid and then distilled to give 1- (cyclohexylphenyl) -1-phenylethane (mixture of structural isomers). Then, 1 liter of 1- (cyclohexylphenyl) -10 1-phenylethane was autoclaved and, in the presence of a nickel catalyst, hydrogenated for 2 hours at an initial hydrogen pressure of 100-100 kPa at 140-170 ° C to give hydrogenated 1- (biphenylyl) - 1-phenylethane (a mixture of structural isomers). The general properties of this hydrogenation product are shown in Table D.

A preparation suitable for traction drive was prepared by incorporating in this hydrogenated product the same additives as mentioned above and this preparation was tested to determine the traction coefficient and subjected to the oxidation test of paragraph 3.2 of JIS K- 2514-1980. The results are shown in Table E.

Example VII

Hydrogenated 1- (ethyl biphenylyl) -1-phenyl ethane, a mixture of compounds of formulas 10 and 11 was prepared according to the procedure of Example VI, except that 1 liter of monoethyl biphenyl was used instead of the cyelo-hexylbenzene and 800 ml a 1: 1 mixture of monoethyl biphenyl and styrene was used in place of the mixture of cyclohexylbenzene and styrene. The general properties of this product 30 are shown in Table D. This product, after mixing with additives as described above, was tested to determine the traction coefficient and then subjected to the oxidation test of Section 3.2 of JIS K-2514-1980. The results are shown in Table E.

35 8103378 φ + v '- 24 - <u o co

• H

I ö

_ φ u1i -cf CM

I | μ 43 O cm r-1 r--, -, 4) 4-Y ay 1> ·> · 1 ·> r4. 03 44 -i4 o oo cn m 03>, 1-1 3 Γί

M iH <USO

Φ> 1 _ 43 £ ® ö d S3 ö <u te »s

Cd 44 cd on co I

00Ή 43 σι O lO Ifl I I I Φ M

O 43 44 a O a a tl d tl S tl μ, -4φθι-4 - or-co · ρ4, η ω i g)

03>, r4 MO - - σι 4-1 O 3 B

>, 43>, 3 cm I ü ft Μ 1rj 43 44 fi Φ Λ Oij

0) <U (U 1-4 Μ> ι · ι4 I

O ^ 44 14 4-1 Mi d (t S3 Φ φ φ σ o o oo

μ M-rlÖOl3®OCM'd-CM

φ O> γ1 M «« 1 1

03 O · π ft iH>, O - O O

fl | i-4> · Η Cti 44 Μ ^ -Ν0Φ f4> 03 co Φ r4 Cd 43 φ θ3 M r4 Φ>, Cd · τ4 S3 CO φ>, ÖH4i ·> M rH cd -Η Φ 43 Φ>, 4 -1 CO Μ Cd <44 Ο Cd CO S3 4-1 00 (3Φσ> οο4θβ φ Ο Φ Η «Ο 1 1 Ο Μ44>, Ογ4ΟΙ'-Ο00 Μ 03 · Η (3 Μ 00 Ν di ft 03>, 43 Φ SI φ r4 45 ^ 44 Φ · ρ4 Φ φ II 1-4 44 Φ ΓΟ - - Cd-QH ΟΙ 00 ιΟ m ο3 μ η ο ο ο - Ρ », Ο> Λ Λ Λ λ I μ & ο ο ο ο τ-4 Φ Ο> ο3>, 03 _> 4 45 ι-4 (3 Φ 4-> Φ d 03 φ φ 43 ^ ι-4 S3 Ο · 4-1 Φ φ Ö α | xj cd Φ ÖO Ο cn CO Cd Cd-QH C \ 00 CO 00 (3oör4c \ ocNinS 44 μ> ooo - 0JMr4>, AQ «A r-4 O 1 aaa

ft03>, ÖO, P00 \ £ 3O00 SO O - O O

ft>, N Φ SvD CM σι co> cd 43 (3 C44 Φ I Φ _d Φ Φ "14 —1 f4 U O 43 43 4c!".

co S3 03 fi Ö Μ Φ r4 Φ Φ W Φ i — t ÖO 03 4-1 Φ

φ -H 03 1 — I H 5 | C ΟΊ O 00 O

n <UMr4 Φ Φ Φ μ> 0—0 CM

cd Φ >> 43 43 -HO ““ "“ £ 4 Φ Φ (3 CdOO 0-00 (3 C Φ a H -H> φ Φ 44 CO 44 S ÖO 1rl LH O 44 Φθ, σσ \ θ <Νσ \ : φο3 ÖO μ ι — I απ4αα Or4 r4> d>, Ο μ - uo 00 CJ Φ <3>, n dd- - σι ιφ 43 ö Φ I Φ 43 m φφ t — I · γ4μ> σ> vo io m 0.0 44 44 Ο W Ο Ο O. - Ο Ο Λ Λ Λ Λ cd> ο — ο ο Μ Η Ο

Ο Ο χ- \ «-J

Ο Ο & «cd 1 Ο Ο 'Ö0 44 Φ Φ * ί - S3 φ Μ · Η ^ 4 β -Η ÖO Cd 44

Cd 44 03 Μ 43 Cd Λ Λ d (3 SS co 03 44 44 μ Φ Ο S Ο >> CO CO ÖO -Η 43 Ν r4 pd

O O CO Ü M ft O

, ÖO -Η ·· Φ r4 O

(3, O CJC 44 44> Cd d Φ

cd O 44440 'H 44' CO Cd O 03> S

, 0 vt -Η -H 'μ ΙΦ O 44 44 · CJ "^ 44 Φ Φ Φ OM-HO / -, (3cd | 3 co ιη · ϊ" 0 44 44 4J f5 CJft®4JÖ0cdC®

β _> Γ4 ,, - ι · μ c Φ I φ 44 cd öO

-V- 'r-J CO CO S ÖO Φ Ή' rl g S u ® v

00 μ O O ft O 44 co P O ft "H

• Η · Φ CJ CJ 44 μ 44CdOCdW®44l44 p £ | O 44 co co Φ o3 CJo30 | 3 '' - 43cJ®

• -Η · ι4 -H -H>, cd>, CO Φ bp cd O

CA O>> O fd $ 4 «1t4 0Ss5MS4 HO> H '-' H44ft 8103378« * .r · - 25 -

Example VIII

Dodecybenzene, obtained by reaction of propylene tetramer with benzene, was placed in an autoclave and, in the presence of a nickel catalyst, hydrogenated under an initial water pressure of 50100 kPa at 150 ° C for 4 hours to prepare alkyl cyclohexane. A traction drive oil was prepared by mixing 50 parts by volume of this alkylcyclohexane with 50 parts by volume of the hydrogenated dibenzyl toluene obtained in Example 1 and incorporating 0.5 wt% in this mixture based on the amount of the mixture, of 2,6-di-tertiary-butyl-p-cresol and 0.5 wt% zinc dialkyl dithiophosphate. This fluid was tested to determine the traction coefficient and subjected to the oxidation test according to section 3.2 of JIS K-2514-1980. The results of these 15 tests, along with the general properties are listed in Table F.

Example IX

Following the procedure of Example VIII, a traction drive oil was prepared from 20 parts by volume of the alkylcyclohexane obtained in Example VIII

and 50 parts by volume of hydrogenated benzyl biphenyl as obtained in Example IV. The liquid was then subjected to the same tests as described in Example VIII. The results are shown in Table F.

25 8103378 ν - 26 -

Table F ”--- -............ ~

General characteristics

Property_ Example VIII Example IX

S.G. (15/4 ° C) 0.88 0.87 5 Appearance colorless, clear colorless, clear

Viscosity (est) (40 ° C) 20.2 17.5

Viscosity (est) (100 ° C) 3.4 3.1

Pour point (° C) -37.5 -35

Flash point (° C) 150 150 10 Hydrogenation degree (%) 98 98

Traction coefficient and result of oxidation test

Example VIII Example IX Traction coefficient 0.086 0.088 Oxidation test:

Viscosity ratio 1.08 1.07

Increase total acid number (mg KOH / g) 0.07 0.05

Heptane-insoluble fraction 20 after the oxidation test (wt%) 0.15 0.13

As can be seen from the examples, the addition of dodecylcyclohexane yielded preparations with a significantly lower viscosity and considerably lower pour points without any substantial loss in the traction coefficient or the oxidation stability.

It will be understood that the invention is not limited to the exact details of the implementation or the exact compounds, preparations and methods described above, but also includes all kinds of modifications and equivalents apparent to those skilled in the art.

8103378

Claims (21)

1. A composition suitable for use in mechanical energy or power transmission units, consisting essentially of a small amount of an antioxidant, mixed with a hydrocarbon oil, characterized in that the hydrocarbon oil has 19 to 30 carbon atoms and per molecule has three six-membered carbocyclic rings and consists of a mixture of compounds of the formula 1, wherein R 1 represents a divalent straight or branched C 5 chain in which y is an integer from 1 to 3, a straight C group in which z is an integer from 1 to 3, R ^, R ^ and Rj. equal or different alkyl groups represent lein 1 to 4 carbon atoms, 1, m and n each represent an integer from 0 to 3 and x 0 or 1 and wherein rings A and B are hydrogenated benzene rings and ring C is a hydrogenated benzene ring, if x is 1 and represents a hydrogenated benzene ring or a cyclohexane ring if x is 0 where the hydrogenated benzene rings are saturated for at least 80 Z but less than 100% of what is theoretically possible and the hydrocarbon oil is otherwise unsaturated. 1 '- 27 - Preparation according to claim 1, characterized in that the benzene rings in the compound of formula 1 are at least 95% saturated. Preparation according to Claim J or 2.25, characterized in that x in formula 1 has the value 1. Preparation according to claim 3, characterized in that the hydrocarbon oil comprises hydrogenated 1- (benzyl-phenyl) -1-phenylethane with 0 to 2 methyl substituents and 0 to 2 ethyl substituents. Preparation according to claim 3, characterized in that the hydrocarbon oil comprises hydrogenated dibenzyl benzene having 0 to 2 methyl substituents and 0 to 2 ethyl substituents. 6. Preparation according to claim 5, characterized in that x in formula 1 has the value 0. Preparation according to claim 6, characterized in that the hydrocarbon oil comprises hydrogenated benzyl diphenyl having 0 to 2 methyl substituents and 0 to 2 ethyl substituents. 8. A composition according to claim 6, characterized in that the hydrocarbon oil comprises hydrogenated 1-biphenyl-1-phenylethane with 0 to 2 methyl substituents and 0 to 2 ethyl substituents. Preparation according to any one of the preceding claims, characterized in that it additionally contains per 100 parts by weight of the hydrocarbon oil to 100 parts by weight of an alkyl cyclohexane in which the alkyl group contains 9 to 20 carbon atoms. Preparation according to claim 9, characterized in that the amount of alkylcyclohexane per 100 parts by weight of the hydrocarbon oil is 10 to 60 parts by weight. A method of operating a traction drive having a point or line contact region between rolling solids, characterized in that the contact region is lubricated with a hydrocarbon oil containing 19 to 30 carbon atoms and having three six carbocyclic rings and consists of a mixture of compounds of the formula 1, wherein Rj represents a divalent straight or branched C rRep where y is an integer from 1 to 3, R 2 represents a straight ^ z ^ 2z 8 rop where z is an integer from 1 to 3 3, R ^, R ^ and R ^ is equal or different alkyl groups having 1 to 4 carbon atoms, 1, m and n each represent an integer from 0 to 3 and x is 0 or 1 and the rings A and B hydrogenated benzene rings and ring C is a hydrogenated benzene ring if x is 1 and a hydrogenated benzene ring or a cyclohexane ring if x is 0, wherein the hydrogenated benzene rings are at least 80% but less than 100 % of the theoretically possible hydrogenation degree are saturated with hydrogen and the hydrocarbon oil is otherwise unsaturated. 12. Process according to claim II, characterized in that the rings in the hydrocarbon oil are at least 95% saturated. 8103378 J - 29 - A method according to claim 11 or 12, characterized in that the hydrocarbon oil is stabilized with an antioxidant. 14. Process according to claims 11-13, 5, characterized in that x in formula 1 has the value I. Process according to claims 11-13, characterized in that the hydrocarbon oil comprises hydrogenated (benzyl-phenyl) -phenylethane with 0 to 2 methyl substituents and 0 to 2 ethyl substituents. Process according to claims 11-13, characterized in that the hydrocarbon oil comprises hydrogenated di-benzylbenzene having 0 to 2 methyl substituents and 0 to 2 ethyl substituents. Method according to claims 11-13, 15, characterized in that x has the value 0. Process according to claims 11-13, characterized in that the hydrocarbon oil comprises hydrogenated benzyl biphenyl having 0 to 2 methyl substituents and 0 to 2 ethyl substituents. Process according to claims 11-13, characterized in that the hydrocarbon oil comprises hydrogenated biphenyl-phenylethane having 0 to 2 methyl substituents and 0 to 2 ethyl substituents. A method according to any one of the claims IJ-19, characterized in that the preparation contains per 100 parts of the hydrocarbon oil up to 100 parts of an alkylcyclohexane in which the alkyl group contains 9 to 20 carbon atoms. 21. Process according to claims 11-20, characterized in that the composition contains on every 100 parts of the hydrocarbon oil 10 to 60 parts of an alkylcyclohexane in which the alkyl group has 9 to 20 carbon atoms. 8103378 - V- »(ΡΛ (R *)« (RA CRA <&) - / ry r, -Tb cy (αΛ_ r, -Tb j- r, -yc \ '1 ^ 2 (Rj ^ (Ri, L (r \ CH »,, & νφ-Ö o" ö. 3 4 CH, X 5 CiHf CH CHj CH, O “O“ '- O 0 “<^ cm'O 6 7 oo ^} o * <Po 8 9 CH> ^ ^ OOA Ol £ K3 10 11 NIPPON STEEL CHEMICAL CO., LTD., Tokyo, Japan MITSUBISHI OIL COMPANY, Limited, Tokyo, Japan 8103378