SE456742B - COMPOSITION SUITABLE FOR MECHANICAL CREDIT TRANSFER AND USE OF COMPOSITION IN CONNECTION WITH TRACTION TYPE DRIVES - Google Patents

Description

456 742 2 Friction or traction drives for mechanical power transmission have been described in a number of articles in previous technical literature. They are extensively treated e.g. in U.S. Patents 3,394,603 and 3,411,369; in Journal of Chemical and Engineering Data, Vol. 5, no. 4, pages 499-507 (1960) and Hewko et al. in Proceedings of the Symposium on Rolling Contact Phenomena, pages 157-185 (1962), Eisevier, Amsterdam, Holland.

As compositions for use in traction drive devices, a large number of substances have been proposed, and among such are e.g. mineral oils (Japanese Publication No. 24,635 / 1964), mixtures of aromatic dialkyl hydrocarbons with diaryalkanes (Japanese Publication No. 40,525 / 1972), polymethyl methacrylate (Japanese Publication No. 31,828 / 1973), adamant compounds (Japanese Patents KOKAI 4,766 / 1971 and 2,yl9 / 1972 U.S. Patent 2,549,377). In the Japanese patent KOKAI 40.726 / 1980, liquids obtained by hydrogenation of bis- (Sá-methylbenzoltoluene) and / or bis- (methylmethylbenzyl) -xylene have been proposed.

In addition, there are many suggestions for naphthalene oils with naphthalene rings. These naphthalene oils include e.g. dicyclohexylmethane (U.S. Patent 3,577,361), dicyclohexylpropane (Japanese Publication No. 36,105 / 1978), hydrogenated cyclic condensation compounds (U.S. Patent 3,411, 369), naphthalines containing at least one carbonaceous cyclic ring (U.S. Patent 3,404) , naphthalene containing at least one carbonaceous cyclic ring (U.S. Patent 3,440,894), naphthalene containing at least two saturated carbonaceous cyclic rings (U.S. Patent 3,925,217) and mixtures of naphthalene and paraffins (U.S. Patent 3, S95,796 and 3,59S, 797) and an oil obtained by hydrogenation of the product resulting from the alkylation of xylene and / or toluene with styrene (Japanese Patent KOKAI 43,108 / 1980).

The aforementioned U.S. Patents 3,440,894 and 3,925,217 cover a large group of naphthalene compounds, and a large number of naphthalines are exemplified. Most of them are compounds that have one or two hydrogenated rings. Among the compounds mentioned in the mentioned patents, those with three or more hydrogenated rings are limited to a small number and include e.g. tericyclohexyls, 1,2,3-tricyclohexylpropane and tricyclohexylmethane. Although they have a high traction factor, they hardly find any practical use, as they exhibit high viscosity and a high crystallization temperature. From the previous technical literature it appears that naphthalene oils with hydrogenated rings exhibit generally prominent properties as lubricants and especially those which are used in traction drive devices.

OBJECTS OF THE INVENTION It is therefore an object of this invention to provide novel compositions suitable for use in mechanical power transmission devices. Another object of the invention is to provide such compositions which are superior in traction and other properties such as resistance to oxidation and resistance to corrosion, and which can be easily synthesized from inexpensive raw materials on a commercial scale.

A further object is to provide a new method in the use of traction drives. Other objects are to avoid disadvantages associated with hitherto existing products and to attain such advantages as will become apparent as the description proceeds.

Summary of the Invention The above-described objects are achieved by providing a composition suitable for use in mechanical power transmission devices, consisting essentially of a minor amount of an antioxidant mixed with a hydrocarbon oil having from 19 to 23 carbon atoms and three hexagonal carbocyclic rings and consists of a mixture of compounds of the following formula: (R 3) ¿(Ru) m .. (R) "(I) 456 742 4 in which R 1 is methylene or ethylene; R 2 is methylene; R 3, R 4 and R 5 are the same or different methyl or ethyl; fl m and n are each an integer from zero to 2; and x is zero or 1; and in which rings A and B are hydrogenated benzene rings and ring C is a hydrogenated benzene ring, when x is zero, said hydrogenated benzene rings being saturated with hydrogen to an extent of at least 80%, but less than 100% of the theoretical value and said hydrocarbon oil being otherwise unsaturated, the composition additionally containing up to 100 partsof alkylcyclohexane, in which the alkyl group contains from 9 to 20 carbon atoms, for every 100 parts of said hydrocarbon.

In one embodiment of the invention, x preferably has a value of 1; in another, X is equal to zero. Preferred compensations in such cases include hydrogenated 1- (benzyl-phenyl) -1-phenylethane having from zero to two substitutable methyl radicals and from zero to two substitutable ethyl radicals; hydrogenated dibenzylbenzene having from zero to two interchangeable methyl radicals and from zero to two interchangeable ethyl radicals; hydrogenated benzylphenyl having from zero to two interchangeable methyl radicals and from zero to two interchangeable ethyl radicals; and hydrogenated 1-biphenyl-1-phenylethane having from zero to two interchangeable methyl radicals and from zero to two interchangeable ethyl radicals; and hydrogenated 1-biphenyl-1-phenylethane having from zero to two interchangeable methyl radicals and from zero through two interchangeable ethyl radicals.

It is advantageous if the composition additionally contains up to 100 parts, preferably 10 to 60 parts of an alkylcyclohexane, in which the alkyl group contains from 9 to 20 carbon atoms, for every 100 parts of said hydrocarbons.

The invention also relates to a method of using traction drive devices with contact at a point or along a line between rolling solids, where the contact area is oiled with the above-mentioned composition.

It has thus been found that a mixture of hydrocarbons having a backbone in which three hydrogenated benzene rings are linearly linked by two chains, CyH2y and CZHZZ, or two hydrogenated benzene rings are linearly linked directly by a Cy Cy2y group and a hydrogenated benzene or cyclohexane ring is linked 456 742 to one of them without any intermediate chain due to its special molecular structure, is particularly effective in fulfilling the objects of the present invention.

Detailed Description of the Invention The main component of the hydrocarbon oil of this invention to be used in mechanical power transmission devices is a naphthalene-type hydrocarbon compound having from 19 to 23 carbon atoms and three hydrogenated benzene rings and is represented by the aforementioned general formula I.

Where x is equal to 1, then the compound of the general formula can be expressed by the general formula II. Where x is equal to zero, this compound can therefore be expressed by the general formula III. m3), <55 "> (H55 1 32 (II) m3), m (H55, / oieei which R 1, R 2, R 3, R 4, R 5, 1, m and n have the same meanings as given above and ring C i formula III is a hydrogenated benzene or a cyclohexane ring.

Where x is 1, the compounds represented by the general formula I include, for example, hydrogenated dibenzylbenzenes, hydrogenated (methylbenzyl) -benzylbenzenes, hydrogenated (dimethylbenzyl) -benzylbenzenes, hydrogenated di- (methylbenzyl) -benzenes, hydrogenated (ethylbenzenes) benzyls - (ethylbenzyl) -benzenes, hydrogenated (diethylbenzyl) -benzylbenzenes, hydrogenated dibenzyltoluenes, hydrogenated dibenzyl-dimethylbenzenes, hydrogenated dibenzyl-ethylbenzenes, hydrogenated (methylbenzyl) -benzyl-toluenes, hydrogenated (dimethyl-benzyleneyl) -benzylene-ethylbenzyl) di- (methylbenzyl) toluenes, hydrogenated di- (ethylbenzyl) toluenes, hydrogenated di- (methylbenzyl) xylenes, hydrogenated 1,1- (benzylphenyl) -phenylethanes, hydrogenated 1,1,456,742 (methylbenzyl) -phenyl-ethanes, hydrogenated 1,1- (benzylphenyl) (methyl-phenyl) -ethanes, hydrogenated 1,1- (benzylmethylphenyl) -phenylethanes, hydrogenated 1,1- (benzylphenyl) (ethylphenyl) ethanes, hydrogenated 1,1- (benzylethylphenyl) -phenylethanes , hydrogenated phenethylbenzylbenzenes, hyd hydrogenated phenethylbenzyltoluenes, hydrogenated diphenethylbenzenes and hydrogenated diphenethyltoluenes.

Among the compounds represented by the above-mentioned general formula II, the following are particularly suitable for the purposes of the present invention: hydrogenated dibenzylbenzenes and hydrogenated (benzylphenyl) -phenylethanes or their derivatives, in which one or two substitutable methyl or ethyl radicals are included , and especially hydrogenated dibenzyltoluenes.

Where x is zero, the compounds represented by the above general formula I include, for example, hydrogenated benzyl biphenyls, hydrogenated benzyl-monomethyl-biphenyls, hydrogenated benzyl-dimethyl-biphenyls, hydrogenated benzyl-trimethyl-biphenyls, hydrogenated-benzyl-hydrogenated- benzyl-diethyl-biphenyls, hydrogenated benzyl-triethyl-biphenyls, hydrogenated biphenyltolyl-methanes, hydrogenated (methyl-biphenyl) tolyl-methanes, hydrogenated (dimethylbiphenyl) -tolyl-methanes, hydrogenated (trimethylbiphenyl) tolyl-methylene methanes, hydrogenated (diethylbiphenylyl) tolylmethanes, hydrogenated (biphenylyl) (ethylphenyl) ethanes, hydrogenated (methylbiphenylyl) (ethylphenyl) methanes, hydrogenated (dimethylbiphenylyl) (ethylphenyl) methanes (trimethylphenyl) ethylphenyl) -methanes, hydrogenated (ethylbiphenylyl) (ethylphenyl) -methanes, hydrogenated (diethylbiphenylyl) (ethylphenyl) -methanes, hydrogenated 1-biphenylyl-1-phenylethanes, hydrogenated 1- (methylbiphenylyl) -1-phenylethanes, (dimethyl-biphen ylyl) -1-phenylethanes, hydrogenated 1- (ethylbiphenylyl) -1-phenylethanes, hydrogenated 1- (diethylbiphenylyl) -1-phenylethanes, hydrogenated 1-biphenylyl-1- (methylphenyl) ethanes, hydrogenated 1- (ethylbiphenylyl) -1- (methylphenyl) ethanes, hydrogenated 1- (methylbiphenylyl) -1- (methylphenyl) ethanes, hydrogenated 1-biphenylyl-1- (ethylphenyl) ethanes, hydrogenated 1- (methylbiphenylyl) -1- (ethylphenyl) ethanes, hydrogenated 1- (dimethylbiphenylyl) -1- (ethylphenyl) ethanes, hydrogenated 1- (ethylbiphenylyl) -1- (ethylphenyl) ethanes, hydrogenated phenethylbiphenyls, hydrogenated phenethylmethylbiphenyls, hydrogenated phenethyldimethylbiphenylethylphenyl ether hydrides , hydrogenated (methylphenethyl) biphenyls, hydrogenated methylphenethyl) methylbiphenyls, hydrogenated (methylphenethyl) ethylbiphenyls and hydrogenated (ethylphenethyl) biphenyls. Among the compounds represented by the above-mentioned general formula III are hydrogenated benzyl biphenyls or their derivatives in which one or two exchangeable methyl or ethyl radicals are included, particularly suitable for the purposes of the present invention.

The compound of general formula II such as e.g. hydrogenated dibenzylbenzenes are obtained by hydrogenation of dibenzylbenzene, which is obtained by a reaction of benzyl halides and benzene in the presence of a catalyst according to Friedel- Craft. Of other benzyl halides, benzyl chloride has been found to be advantageous. The benzyl halides are advantageously used in an amount of not more than 1 mol, preferably in the range from 0.1 to 0.5 mol, per mol of benzene. Among other compounds useful as Friedel-Craft catalysts, sulfuric acid, boron trifluoride and aluminum chloride have been found to be particularly suitable, with aluminum chloride being the best alternative. The amount of aluminum chloride to be used should preferably range from 0.000l to 0.1 mol per mol of benzyl chloride. Although the reaction temperature can be selected in the range from 20 ° to 150 ° C, it is preferably selected in the range from 400 to 50 ° C. Although the reaction pressure need only exceed the minimum level required to keep the products in the reaction vessel in a liquid state, an overpressure in the range from 0 to 98l kPa has proved advantageous for carrying out the reaction. This reaction gives dibenzylbenzene, which is a mixture of ortho-, meta- and paraisomers. These isomers may be subjected to hydrogenation in their mixed form or individually. Prior to hydrogenation, the Friedel-Craft catalyst is removed from the reaction mixture by washing with water, and the unreacted portions of the reagents and any by-products in the reaction are expelled from the reaction mixture by distillation to separate the dibenzylbenzene. Thereafter, the isolated reaction product is treated in the presence of a hydrogenation catalyst to undergo the hydrogenation. I.

The hydrogenation catalyst used is one of platinum, palladium, rhodium, ruthenium or nickel with good results. The nickel catalyst is used in an amount ranging from 0.1 to 20% by weight. The pressure of the hydrogen gas is suitably selected in the range from 981 to 19620 kPa overpressure. Hydrogen for the hydrogenation is used in an amount of 9 moles or more per mole of 456,742 dibenzylbenzene, preferably 1.1 times the above molar ratio. The reaction temperature during the hydrogenation is in the range: from 100 ° -1 to 111 ° C, preferably from 140 ° to 11 °.

When the hydrogenation has progressed to a predetermined hydrogenation ratio, the reaction is stopped and followed by a separation of hydrogenated dibenzylbenzene. This separation of the reaction product can be achieved simply by removing the catalyst used.

It can be performed by a separation by filtration or optionally by any common method of treatment of lubricant, for example treatment with activated clay soil. If necessary, distillation may be used for this purpose. However, the advantage of a distillation process is not so great, unless the reaction has formed compounds in the form of low-boiling by-products, otherwise it is otherwise very difficult to achieve by distillation a separation of fully hydrogenated dibenzylbenzene and partially hydrogenated dibenzylbenzene or separation. of isomers.

Preparation of an alkyl-substituted hydrogenated dibenzene is carried out by substituting benzene or benzyl halides or both with an alkyl-substituted benzene- or alkyl-substituted benzyl halide or both as raw materials, these raw materials being used in suitable combinations.

Toluene, ethylbenzene, propylbenzene, xylene, cumene, diethylbenzene and methylethylbenzene are suitable alkyl substituted benzenes for this purpose. Suitable alkyl-substituted benzyl halides for the purpose include derivatives of benzyl halides with exchangeable monomethyl or monoethyl radicals. When such alkyl-substituted raw materials are used, the reaction can be carried out under conditions similar to those described above, and the hydrogenation can be carried out in a similar manner.

When a compound of the general formula (113): δ * ~ «(in which R 3 and 1 have the same meanings given above, and X represents a halogen), was used instead of the aforementioned benzyl halides or an alkyl substituted derivative of the same, hydrogenated diphenethylbenzene or an alkyl-substituted derivative thereof can be obtained. In a preferred embodiment of the process for the preparation of the compounds of this invention, a compound of the type hydrogenated (benzylphenyl) -phenyl-alkane is obtained by reacting diphenylalkane with benzyl halides in the presence of a catalyst according to Fridel-Craft to form a ( benzylphenyl) -phenyl-alkane and then hydrogenate this reaction product. In this case, when a 1,1-diphenyl-alkane is used as diphenylalkane, a hydrogenated 1- (benzylphenyl) -1-phenyl-alkane type compound is obtained.

Use of an alkyl-substituted 1,1-diphenylalkane or an alkyl-substituted benzyl halide or both results in the preparation of a hydrogenated alkyl-substituted 1- (benzylphenyl) -1-phenyl-alkane compound. When a 1,3-diphenylalkane is used as the diphenylalkane, a hydrogenated 1- (benzylphenyl) alkane type compound is obtained, and when a 1,2-diphenylalkane is used, a 1-benzylphenyl-2-phenylalkane or a 2-benzylphenyl is obtained. -1-phenylalkane.

In all these cases, the type of Friedel-Craft catalyst, the conditions during the Friedel-Craft reaction of the alkyl halides, the conditions during the hydrogenation, etc., are similar to those described above. The aforementioned 1,1-diphenylalkanes can be obtained by a reaction of ethylbenzene or styrene and benzene in the presence of a Friedel-Craft catalyst.

The compounds of general formula III such as e.g. hydrogenated benzylbiphenyl is obtained in a manner similar to those of general formula II by hydrogenating benzylbiphenyls obtained by reacting benzyl halides with biphenyls in the presence of the Friedel-Craft catalyst. In this case, the amount of aluminum chloride to be used is preferably in the range of from 0.000l to 0.05 moles per mole of benzyl chloride. Although the reaction temperature can be selected in the range from a level exceeding the melting point of the participating biphenyls up to 180 ° C, it is preferably selected in the range from 700 to 10 ° C. Although the reaction pressure need only exceed the minimum level required to keep the contents of the reaction vessel in the liquid state, it is preferred that it fall within the range of 0 to 4905 kPa gauge. This reaction gives as a product benzyl-biphenyl, which is a mixture of ortho-, meta- and paraisomers.

These isomers can be subjected to hydrogenation either in their mixed form or separately. Prior to hydrogenation, the reaction mixture is washed with water and distilled to remove reagents which did not participate in the reaction, as well as the Friedel-Craft catalysts used, and the benzyl biphenyl is separated. The separated benzyl-biphenyl is then hydrogenated by introducing hydrogen in the presence of a hydrogenation catalyst. In this case, the conditions are the same as those prevailing in the hydrogenation process for the production of the compounds of general formula II.

The production of a hydrogenated alkyl-substituted benzylbiphenyl is carried out by substituting a biphenyl or a benzyl halide or both with an alkyl-substituted biphenyl or an alkyl-substituted benzyl halide or both as raw materials by using these raw materials in suitable combinations. Suitable alkyl-substituted biphenyls are monomethylbiphenyl, monoethylbiphenyl, monopropylbiphenyl, dimethylbiphenyl, monoethylbiphenyl, monopropylbiphenyl, dimethylbiphenyl, diethylbiphenyl and methylethylbiphenyl. And suitable alkyl-substituted benzyl halides are derivatives of benzyl halides with monomethyl, monoethyl and other similar exchangeable radicals. When these alkyl-substituted derivatives are used, the reaction can be carried out under conditions similar to those described above. The hydrogenation can also be carried out in a similar manner.

When a compound represented by the general formula: (n: CH 2 - CH 2 X (in which R 3 and 1 have the same meanings given above, and X represents a halogen), was used instead of the aforementioned benzyl halides or an alkyl substituted derivatives thereof, a hydrogenated phenethylbiphenyl or an alkyl-substituted derivative thereof can be obtained.

Another preferred embodiment of the method of making the compound of this invention consists in the step of reacting cyclohexylbenzene or a biphenyl with Styrene in the presence of a Friedel-Craft catalyst and then hydrogenating the reaction product formed. Suitable Friedel-Craft catalysts for this reaction are boron trifluoride, aluminum chloride and sulfuric acid. When sulfuric acid is selected as the catalyst, it is desirable that the amount of this catalyst fall in the range of from 5 to 50% by weight based on the amount of participating biphenyl. The cyclohecylbenzene or biphenylene and styrene are preferably used in equal or almost equal molar proportions in order to prevent the otherwise possible polymerization of styrene in the reaction. The reaction temperature is desired to be low, in the range of 0 ° to 30 ° C. When the reaction is complete, the reaction mixture is washed with water to remove the catalyst used and then distilled to separate 1- (biphenylyl) -1-phenylethane or 1- (cyclohexylphenyl) -1-phenylethane as a reaction product.

The compound, when subjected to hydrogenation by the same procedure as described above, yields hydrogenated 1- (biphenyllyl) -1-phenylethane.

When a similar procedure is repeated using an alkyl-substituted cyclohexylbenzene or an alkyl-substituted biphenyl or an alkyl-substituted styrene or instead of cyclohexylbenzene or biphenyl or styrene, an alkyl-substituted hydrogenated 1- (biphenylyl)) is obtained. Alkyl-substituted cyclohexylbenzenes, suitable for use for this purpose are cyclohexylmethylbenzenes, cyclohexylethylbenzenes, cyclohexylpropylbenzenes, cyclohexyl-dimethylbenzenes, cyclohexyl-diethylbenzenes, (methylcyclohexylenyl) -benzyl-benzyl- these. Alkyl-substituted biphenyls suitable for use herein are the same as those set forth above. Suitable alkyl-substituted styrenes include the compounds represented by the general formula: 33 CH 2 -CH 2 (R) 1 A typical example of these compounds is vinyltoluene. Wkmethylstyrene can also be used to advantage in a similar manner. When these alkyl-substituted derivatives are used, the reaction can be carried out under conditions similar to those described above.

The composition of the present invention, which is to be used in mechanical power transmission devices, can be used in its independent state. When mixed with an alkYlCYk10heXä C (C9-C20), added in an amount of not more than 100 parts by weight, preferably in the range from 10 to 60 parts by weight, based on 100 parts by weight of the compound of this invention, a composition having a varying degree of viscosity can be obtained , which is useful in mechanical power transmission devices without, to any appreciable extent, deteriorating the properties which the oil is expected to exhibit for its function. Alkylcyclohexanes suitable for this purpose are obtained by hydrogenation of alkylbenzenes derived by reaction of propylene from trimer to pentamer with benzene.

The compositions of the invention may contain, in addition to their main constituents, namely a small amount of an antioxidant and a hydrocarbon oil as described above, other additives or by-products, as long as these do not adversely affect their suitability for use in mechanical power transmission. In addition to antioxidants, the compositions may thus contain such additives as anti-corrosion agents, defoamers and the like. They may also contain a small amount of the by-products which arise during the production process of the hydrocarbon oils represented by the general formula I.

However, a larger amount of aromatic hydrocarbons or compounds with a double bond is preferably avoided. In the manufacture of a compound represented by the general formula I by hydrogenation of a corresponding hydrocarbon, it is therefore desirable that it be allowed to continue until the hydrogenation reaches at least 80% of completeness, but 95% is desirable and more than 95% is preferred. A virtually complete hydration, i.e. so that less than 1% of unsaturated product needs to be removed is virtually impossible. However, such complete removal of unsaturated reagent material is not required, as the objects of this invention are not disturbed by the presence of unsaturated compounds in small amounts. The hydrocarbon oils which constitute the main components of the compositions according to the invention are thus mixtures of components in different stages of hydrogenation or isomers or both and can be used as such or in combination with suitable additives in the manner mentioned above.

Accordingly, the reference to hydrogenated compounds must be understood as including such compounds which have been hydrogenated to at least 80%, preferably to at least 95% of the theoretical value.

The coefficient of reaction of a given oil is generally measured by using a traction driver. In the present invention, the measurement has been made using a four-roll friction tester of Soda's construction.

(T. Kimura and M. Muraki "TRIBOLOGY", 1979 (12), p. 255)). In this tester the transaction (roll friction) takes place in three contact areas, which are formed between an inner centrally located roller 13 * D 456 742 and three outer rollers, which are tangentially located around the non-central roller, which are arranged in such a way that equal perpendicular loads exert a pressure effect on the three contact areas.The surface pressure on contact expressed by the average Hertzian pressure falls within the range from 0.575 to 1,157 GPa The other conditions for determining traction by this tester are shown in the following table.

Table l. Conditions for traction determination.

Rotation speed 1.05 to 4.19 m / sec Sliding speed 0 to 0.22 m / sec Test rollers Material bearing steel, SUJ -2 Hardness (HV) 760 to 800 Dimensions 40 mm x 9 mm (outer rollers) (diameter and width) 40 mm x 5 mm (central rollers) Lubrication method - Drip about 10 ml / min in flow volume Temperature of fed oil 28 ° C The procedure for carrying out the test meant that the central and outer rollers were first given a constant rotational speed, after which these rollers were subjected for a load, and then the rotational speed of the outer rollers was accelerated, while the speed of the central roller was kept constant, whereby sliding / rolling conditions were developed to allow a continuous measurement of the change in friction torque or the coefficient of traction. The torque of the friction was determined by directly measuring the torque in the centerless bearing shaft of the central roller by means of a distortion meter with resistance wire.

The coefficient of traction, which was determined under the conditions described above, first tends to rise in a straight line in step with the increasing slip / roll conditions, after which a peak is followed by a fall. In the curve which can thus be drawn, the important zone falls from the point of view of the practical use of the oil, in the first part showing a straight line, where the magnitude of the value of the heat evolution due to the cutting of the oil film is not large. The traction coefficient precisely within this zone will thus only be the only one, which is taken into account in the following. 14,456,742 Under the test conditions with 1,157 GPa in average Hertzian pressure and 4.19 m / s rotational speed, for example, the following traction coefficients were achieved. viscosity (cst) traction at 40 ° C coefficient Mineral oil of naphthalene type 8.0 0.050 Hydrogenated Polyisobutylene 10.0 0.060 Dicyclohexane 2.9 0.065 Ethyldicklohexane 4.0 0.060 Methylcyclohexane Cyclohexylmethane 4.2 0.065 Dicyclohexylethane (4-cyclohexane) Hydrogenated OL ~ methylstyrene linear dimer 22 0.090 * crystallized at room temperature.

The coefficient of traction of the compound obtained by the present invention, on the other hand, reached a value as high as 0.095, which is considerably higher than the values found for the hydrocarbons mentioned above. Accordingly, it has been found that the product of this invention is even superior hydrogenated pyrimethylstyrene linear dimer, which is currently marketed as a 'best' synthetic traction fluid.

In addition to the traction coefficient and stability to oxidation, the mechanical power transmission composition required for mechanical power transmission has a solidification or freezing point lying at least at -10 ° C and a viscosity at 40 ° C of 7-150 cs: under atmospheric pressure is that prefer. 456 742 viscose (cst) solidification at 40 DEG C. or freezing point (° C) o-tercyclohexyl - 45 m-tercyclohexyl - 63β-tercyclohexyl - 162 m-, β-tercyclohexyls in mixture crystallized at room temperature. tricyclohexylmethane - 59 1.1.3-tricyclohexylpropane about 2500 As can be seen from the above, the above-mentioned compounds are not suitable as a base oil for the mechanical power transmission composition.

Furthermore, in order to ensure a stable function of a traction drive device for a long period of time, it is required that the composition for mechanical force transmission has good sealing properties. The following table shows the sealing properties of the composition for mechanical power transmission when using base oils with as suitable a viscosity as the composition and relatively good traction properties. The tests were performed at 120 ° C for 70 hours with nitrile rubber (Buna N) and acrylic rubber (Buna N) and acrylic rubber based on a method of JIS K-6301.

Base oil Examples 1 and 4 Hydrogenated fi-methylstyrene dimer oil for traction operation Rubber Nitrile- Acrylic- Nitrile- Acrylic rubber rubber rubber rubber Properties: (Buna N) (Buna N) Weight gain (%) 3.45 1.48 7.30 3.86 Volume increase (%) 6.58 3.42 13.6 7.67 Tensile strength (Kgf / cmz) 195 Bl 168 85 Elongation (%) 260 140 150 110 Hardness variation (%) -6 0 -6 -1 Aniline point ss ° c 70 c 16 _ 456 742 The oil of the present invention can be used alone, but an addition of additives is a preferred embodiment.

In addition to the traction properties described above, the oil for use in a traction drive device must have such properties as are usually expected of lubricants, e.g. oxidation stability, corrosion resistance of any viscosity index improver, abrasion resistance, anti-corrosion properties, rubber swelling ability and foam prevention ability. Depending on how the oil is to be used, suitable additives such as 2,6-di-tertiary-butyl paracresol and other similar alkylphenols, zinc dialkylthiophosphate and other similar sulfur phosphorus compounds may be added as antioxidants; amines, esters and metal salts as anti-corrosion agents; polymethacrylates as viscosity index improvers; and silicon-type polymers as antifoam agents are added.

The invention will now be described in more detail below with reference, for example, from practice. Wherever "parts" or "percentages" are mentioned in the following examples and elsewhere, they are parts by weight and percentages by weight, unless otherwise indicated.

In the following examples, a composition suitable for use in traction propellants was prepared by adding to hydrogenated dibenzyltoluene or equivalent oil of the invention as antioxidants 2,6-di-tertiary-butyl paracresol and zinc dialkyl dithiophosphate, each of the latter an amount of 0.5% by weight. This oil was tested for its traction coefficient under the aforementioned conditions and then subjected to an oxidation test according to the procedure described in section 3.2 (Test method for oxidative stability in oil explosion engines according to Japanese Industrial Standard (JIS) K-2514-1980 ( Test method for oxidative stability of lubricating oils).

Example 1 To 3 parts of toluene was added 0.002 to 0.01 part of aluminum chloride. The mixture was heated to 70 ° C and then allowed to react with 1 part of added benzyl chloride for two hours. The reaction mixture was washed with water to remove the catalyst and then distilled to expel the part of the reagents which did not participate in the reaction. The dibenzyltoluene thus obtained (a mixture of isomers) was placed in an autoclave and subjected to hydrogenation in the presence of a nickel catalyst for four hours, the hydrogen pressure at the start being 3924 kPa overpressure and the temperature being maintained at 20,000 to form hydrogenated isomeric mixture of dibenzyltoluene. ).

General data for this hydrogenated dibenzyltoluene are shown in Table 2.

The results of the oxidation test are shown in Table 3. For comparison, a commercially available hydrogenated OC-methylstyrene linear dimer type was subjected to the same test for traction drive devices as well as an oil made from mineral naphthalene oil.

The oxidation tests were performed under the following conditions: Amount of product tested 300 ml Temperature l65.5 ° C Time 72 hours Oxidation catalyst Copper and iron Example 2 To 4 moles of 1,1-diphenylethane was added 0.001 to 0.005 moles of aluminum chloride. The mixture was heated to 60 ° C and allowed to react with 1 mole of added benzyl chloride for 20 minutes.

Then the mixture was washed with water to remove the catalyst used, after which the residue was distilled to expel those parts of the reagents which did not participate in the reaction.

The separated 1- (benzylphenyl) -1-phenylethane (mixture of isomers) was placed in an autoclave and subjected to hydrogenation for five hours in the presence of a nickel catalyst, the liquid pressure at the start being 9810 kPa gauge and the temperature being maintained at 140 to 170 ° C. and to form hydrogenated 1- (benzylphenyl) -1-phenylethane (mixture of isomers). General data for this reaction product are shown in Table 2.

This product, in accordance with the above description, was tested for traction coefficient and subjected to the oxidation test as specified in section 3.2 JIS K-2514-1980. The results are shown in Table 3. 456 742 m Example gel 3 A hydrogenated monoethyl substituted 1- (benzylphenyl) -1-phenylethane, a mixture of the compounds of the formulas C ° z "5 9.3 _ ÉHS 2" 5 Ö .. en -O- cnz-O and O- cH: H2 -O were obtained by following the procedure of Example 2 except that 4 moles of monoethyl substituted 1,1-diphenylethane were used in place of 1,1-diphenylethane General data regarding this reaction product is shown in Table 2. This in accordance with the above composite product was tested for traction coefficient and subjected to the oxidation test specified in section 3.2 of JIS K-2514-1980 The results are shown in Table 3. 456 742 Nß.m æN.o mA. o ma.ø ~ Ho ß.m ov.o æo.o o fi. o wo.o eN.æ oN. «æo. fi oA.a æo.H mo.o mo.o mo.o mo.o v.mo. o Güßhdßm ÜH> fi0 U fl WO ¥ mH> \ & 0> ON @ WCOHUßÜHXO HÜUWU UÜ ¥ Hw0Mw fl> ¥ .CUHOGM> al HUwCOwU ¥ GHM "now mn fl o Uwe FLOW ~ m f = H ~ jr f oc al qmuumz cmuxum fi auoë al IU al øuwuvæm m f wmswxm N Hwmëwxm H Hmmëwxm> OH fl WCO al UNUHXO> al UMU FI5 wuh S00 UCOHUHwNOOXmCO fl U ¥ MHB M HHUDMB ^ uGmuoHmmux fl> v vw> oHmmn0 al # MW L al xo uwumw Hwcøvmmn nm flfl MSS f o ^ m \ mox wav uu fi nvwuæm ß al mvou> m mc f CXO «MW: m H f m unumuwu« m0xw f> "> oumwco« umu «x O UCW f b f wwmoxmco al uxnua uxcømßmwa .æv wwcm fifi wßwßwwmc al uwwøæz .O V uxcømäm fl m AUOV uxmømwmc fl n al wuw fl u QQH. .umov »m» Hwoxm fl> Awoovv .umov »w» fl woxw fl> NUCÜWWUD ^ uo «\ mH. »1H> x fi w fl uwmw æm mm mm || | «Nm fl .xmë om 1 .xmë ow 1 om 1 m.wa w.ß mm m.mAw m.wo fl wm um fl x .mæ fi mumm Nw fl x .wn fi mumm wm fl x .mn fi mumm mm.o om.o om.o cøuw fl æcmw« | ^ a >: wwH> w: mnv | a cmuw fl æcmw vmumsuaumnnm fl æuwocoë | fl | .fi »: wwAæwcwnv cwø fi ou fi wmnwn flfl ømumuuæm IH Uøuwuøæz fl mnouuæm mvm fl mmüm c mcüm fifi mmüm fl mmüm fl dm5 Hmm ümm empelmm empelmm flm2 mmc empelmm empelmm empelmml flm2 mmm empelmm empelmm empelmml The mixture was heated to 70 ° C and then allowed to react with 1 part of added benzyl chloride for 20 minutes. The reaction mixture was washed with water to remove the catalyst used, and the residue was then distilled to expel those parts of the reagents which did not participate in the reaction.

The benzylphenyl produced (a mixture of isomers) was placed in an autoclave with an internal volume of 1 liter and subjected to hydrogenation in the presence of nickel as catalyst for two hours, the hydrogen pressure at the start being 9810 kPa gauge and the temperature being maintained at 140 to 170 ° C to form hydrogenated benzylbiphenyl (a mixture of isomers). General data for this hydrogenated benzylbiphenyl are shown in Table 4.

This product, compounded above with 0,5% by weight of 2,6-di-tertiary-butyl-paracresol and zinc-dialkyl-dithiophosphate each as antioxidants, was tested for its coefficient of traction and subjected to the oxidation test in the manner specified in paragraph 3.2 in JIS K-25l4- 1980. The results are given in Table 5.

Example 5 A hydrogenated benzyl-monoethylbiphenyl, a mixture of compounds of the formulas C235 CZRS Q wfesö o fl z-: ä fl was obtained by repeating the procedure of Example 4 except using 5 parts of monoethylbiphenyl and 0.03 part of aluminum chloride. General data on this reaction product are given in Table 4. This reaction product, composed in the above manner, was tested for its coefficient of traction and subjected to the oxidation test specified in section 3.2 of JIS K-2514-1980.

The results are found in Table 5. 21 456 742 Example 6 1 liter of cyclohexylbenzene and 200 ml of concentrated sulfuric acid were introduced into a reaction vessel, and the resulting mixture was kept at a temperature of 15 ° C. Then, to the resulting mixture was added dropwise over a period of two hours 800 ml of a mixture of cyclohexylbenzene and styrene in a mixing ratio of 1: 1, while keeping the temperature of the mixture in the range from 15 ° to 20 ° C. At the end of the dropwise addition to the mixture, 200 ml of concentrated sulfuric acid were added to allow the reaction to proceed for a further 30 minutes. Then the mixture was washed several times with water to remove residues of sulfuric acid, whereupon the residue was distilled to separate 1- (cyclohexylphenyl) -1-phenylethane (a mixture of isomers). Then 1 liter of 1- (cyclohexyl-phenyl) -1-phenylethane was introduced into an autoclave and subjected to hydrogenation in the presence of nickel as a catalyst for two hours, the hydrogen pressure at the start being 9810 kPa gauge, and the temperature maintained at 140 ° to 11 ° C. ° c 1 And to form hydrogenated 1- (b-phenyllyl) -1-phenylethane (a mixture of structural isomers).

General data regarding this product are shown in Table 4.

A composition suitable for traction operation was prepared, in which case the same additive as above was added in this hydrogenated product, and the product was tested for the traction coefficient and subjected to the oxidation test specified in section 3.2 of JIS K-2514-1980. The results are given in Table 5.

Example 7 Hydrogenated 1- (ethylbiphenylyl) -1-phenylethane, a mixture of compounds of the formulas ° 2 "5 __ CH3 CH3 'cgns \ - ~' * ~ f ~ \ (from <¥ _ / - cn ~ { Was obtained by repeating the procedure of Example 6 except that 1 liter of monoethylbiphenyl was used instead of the cyclohexylbenzene, and 800 ml of a mixture of monoethylbiphenyl and styrene in a mixing ratio of 1: 1 was used instead of mixing cyclohexylbenzene and styrene.General data for this product are given in Table 4. This product composed in the above manner was tested for its traction coefficient and was subjected to the oxidation test specified in section 3.2 of JIS K-25l4-1980. The results are found in Table 5. 456 742 Nh.m æ ~ .o m fl. a æa.o oN.o ma.o ~ æ muK fl>. um> 0H & mcOHvø © «x0 _ uovuw uucmumon om flfl m flfi o ~. ~ O«. ° @ o. ° m @ .o @ ° .o @oo .m \ møx va. Vm fi øß sum m fl uuøu> m wcwcxo «Nm o ~ .A mo. Fl mo.a o fl.fl wo.H wønß fifi mnuwu mu0u fl møMm «>"> oumu: 0 «uøu« x0 n: .o mo.o mo.o mo.o mo.o mmo.o UCO f O fl muwoxmcøwuxmua UMMC f c | øuocm> «uvwcoau | x« U »How m flfi o nn f ø Iumë FLOW umnca fi ca ~ muwnZ a fl uhumn al æuwënoß nmuwuøæm ß Homäwxm m Ammëwxm m Hmmëøxm« Awmëwxm uxcømuwua microns> oumm = O fl umn al xo> m UNU al omou nuo wcw f O fl wuwoxwco al uxmus m fifi mnma wa mm wm mm ^ ». wu = -H «nHnwwm = fi ~ w ~ u> m sme m. ~ fl | .xma ø ~ | .äns øwa man Au V uxnømmma fl n fi wuw m. = H ° .ß m. @ m. «Au ° = ~ w.» mu. uw »« moxw fl> Aon ~ .om m.mw ~ .fi «^ wOcwv ^ # mov uwu fl m0xm«> uß fi x _mn ~ m ~ m @ uß fl x .mø fi muwm um fi x .ww fl muwm um fi x .mo fl muwm wø = ø «m» a nm. mm.o mm.o mm.o ~ U0v \ mav vx fl b x fl u fl ummw cmuu fi ncmw cmuw fi æcww Hæcww fl n | fl | .fi> H »= w« fl n ~ »» w. «H | .H> H> = w« fl n.aH ~> »wo = oa | ~> m = wn. ~> = ww «n ~> m = ~ n IH fl øuuuvæx uøuouønm umuouøæm øøumunäm mmxmcmmm fl un fl mu NCÉNÉH .mä v H fi ønøa 24 456 742 Example 8 catalyst and with a hydrogen pressure at the start of 4905 kPa overpressure for 4 hours during which the temperature was maintained at 150 ° C, to form alkylcyclohexane. An oil for traction drive devices was prepared by mixing 50 parts by volume of this alkylcyclohexane with 50 parts by volume of the hydrogenated dibenzyltoluene obtained in Example 1, and to this mixture was added 0.5% by weight, based on the amount of mixture, of 2,6-di each. tertiary-butyl paracresol and zinc dialkyl dithiophosphate. This liquid was tested for its traction coefficient and subjected to the oxidation test in accordance with the provisions of section 3.2 of JIS K 2514-1980.

The results of the samples are shown together with general data in Table 4.

Example 9 Repeating the procedure of Example 9, a traction propulsion oil was prepared from 50 parts by volume of alkylcyclohexane obtained in Example 8 and 50 parts by volume of hydrogenated benzylbiphenyl obtained in Example 4. Thereafter, the liquid was subjected to the same test as described in Example 8. The results are shown in Table 6.

Table 6 General data Property Example 8 Example 9 specific gravity (1s / 4 ° c) 9.88 0.87 Appearance Colorless, clear Colorless, clear Viscosity (cst) (40%) 20.2 17.5 Viscosity (cst) (100 ° C) 3.4 3.1 Solidification point (° C) -37.5 -35 Flash point <° c) iso 150 Hydration ratio (%) 98 98 25 456 742 Traction coefficient and result of the oxidation test Test point Example 8 Example 9 Traction coefficient 0.086 0.088 Oxidation test: Viscosity ratio 1.08 1.07 Increase in total oxygen number (mg Con / g) 0.07 0.05 Insoluble heptanes after the oxidation test (weight percent) 0.15 0.13 As can be seen from the examples, the addition of dodecylcyclohexane in the compositions resulted in significantly lower viscosities and significantly lower solidification points without any more significant loss in traction coefficient or stability against oxidation.

It should be clearly understood that the invention is not to be limited to the exact working details or exact compounds, compositions, methods or procedures shown and described, as obvious modifications and equivalent dispositions will be readily apparent to those skilled in the art. .

Claims (9)

456 742 26 PATENT REQUIREMENTS 1. A composition suitable for use in mechanical power transmission units, characterized in that it comprises a minor amount of an antioxidant in admixture with a hydrocarbon oil having 19-23 carbon atoms and three hexagonal carbocyclic rings and is a mixture of compounds of the following formula: (net m 'men nl (122): c (I) in which R 1 is methylene or ethylene; R 2 is methylene; R 3, R 4 and R 5 1, m and n are each an integer from zero to 2; is the same or different methyl or ethyl, and x is zero or 1, and in which the rings A and B are hydrogenated benzene rings and ring C is a hydrogenated benzene ring, when x is zero, said hydrogenated benzene rings being saturated with hydrogen to an extent - of at least 80%, but less than 100% of the theoretical value and said hydrocarbon oil is otherwise unsaturated, the composition optionally additionally containing up to 100 parts of alkylcyclohexane, in which the alkyl group contains from 9 to 20 carbon atoms, for every 100 parts of said hydrocarbon. 2. A composition according to claim 1, characterized in that said benzene rings are saturated up to at least 95%. A composition according to claim 1, characterized in that x in the formula is l. 4. A composition according to claim 3, characterized in that said hydrocarbon consists of hydrogenated 1- (benzylphenyl) -1-phenylethane having from zero to and 456 742 27 with 2 exchangeable methyl radicals and from zero to two exchangeable ethyl radicals. 5. A composition according to claim 3, characterized in that said hydrocarbon consists of hydrogenated dibenzylbenzene having from zero to two interchangeable methyl radicals and from zero to two interchangeable ethyl radicals. Composition according to Claim 5, characterized in that x in the formula is 0. 7. A composition according to claim 6, characterized in that said hydrocarbon consists of hydrogenated benzyl biphenyl having from zero to two interchangeable methyl radicals and from zero to two interchangeable ethyl radicals. 8. A composition according to claim 6, characterized in that said hydrocarbon consists of hydrogenated l-biphenyl-1-phenylethane having from zero to two exchangeable methyl radicals and from zero to two substitutable ethyl radicals. Use of a combination according to claim 1 in connection with traction drive devices, which in one place or along a line have contact between rolling solids, meaning that the contact area - is oiled with a hydrocarbon oil having 19-23 carbon atoms and three hexagonal carbocyclic rings and consists of a mixture of compounds of the following formula: 013)! (R ") m '(1155 H1 but C (I) 1 in which R is methylene or ethylene; R 2 is methylene; R 3, R 4 and R 5 are the same or different methyl or ethyl; 1, m and n are each an integer from zero to 2, and x is zero or 1, and in which the rings A and B are hydrogenated benzene rings and ring C is a hydrogenated benzene ring, when x is zero, said hydrogenated benzene rings being saturated with hydrogen to an extent of at least 80%, but less than 100% of the theoretical value and the said hydrocarbon oil is otherwise unsaturated.