A process for improving the coefficient of traction at high temperatures in a traction drive, and a traction drive fluid for use therein. This traction drive fluid comprises the hydrogenated product of a dimer, a trimer or a tetramer of norbornanes and/or norbornenes, as specified in the specification, and exhibits excellent traction performance over a wide temperature range from low temperature to high temperature.

Process for improving the coefficient of traction and traction drive fluid

Acetylenic epoxides and dienes

2-vinyl-6, 6-dimethylnorpinane and polymers thereof

3-vinyl-2, 2-dimethylnorcamphane and polymers thereof

Unsaturated cyclic compounds

Compounds of the formula (1): where X is -H or -CH3 are prepared by the removal of two molecules of H2 from a compound of formula (2): where Z is Cl, Br, I, OH, or OCOR, where R is alkyl, preferably methyl. When Z is OH, dehydration may be carried out by heating in the presence of alumina, aluminium silicate, phosphoric acid on silica gel, or silica-alumina at 65-150 DEG C. When Z is halogen dehydrohalogenation may be accomplished by refluxing with alcoholic caustic alkali. When Z is acyloxy the compound is pyrolized at 450-550 DEG C. The compounds of formula (2) may themselves be prepared by hydrogenation, e.g. catalytic reduction with hydrogen over nickel or platinum oxide, of the corresponding 5,6-ethylenically unsaturated compounds. Such unsaturated compounds can be formed by a Dials-Alder condensation between cyclopentadiene-1,3 or 1-methyl cyclopentadiene-1,3 and maleic anhydride, a maleic diester or maleic or fumaric acid; the anhydride or diacid grouping can then be reduced with LiAlH4 to a 2,3-dimethylol grouping or esterified; the diester grouping can be transformed to dimethylol with hydrogen and chromite or with sodium and alcohol. The hydroxyl groups can then, if desired, be transformed to halide (e.g. with phosphorus triiodide or red phosphorus and iodine) or to ester groups by acylation (e.g. with acetic anhydride). Reduction of the 5,6-unsaturation can, if desired be accomplished prior to the formation of the methylol groups. Compounds having 5,6-unsaturation may also be conveniently prepared by a Dials-Alder condensation between cyclopentadiene-1,3 or 1-methyl cyclopentadiene-1,3 and a butane-2 derivative selected from: HOCH2.CH = CH.CH2OH, ClCH2.CH = CH.CH2Cl and RCOOCH2.CH = CH.CH2OCOR, where R is alkyl, preferably methyl. The compound of formula (2) in which Z is OH can also be prepared by the reduction of a 2,3-dimethylol - bicyclo - [2 : 2 : 1] - 2,5 - heptadiene, itself prepared by a Dials-Alder condensation between cyclopentadiene-1,3 or 1-methyl cyclopentadiene - 1,3 and 1,4 - dihydroxybutyne - 2. Dicyclopentadiene may be substituted for cyclopentadiene. In an example, dicyclopentadiene and 1,4-dihydroxybutene-2 are heated at 200 DEG C. for 8 hours to give 2,3-dimethylol-bicyclo-[2 : 2 : 1]-heptane-5 which was acetylated with acetic anhydride to the corresponding diacetate and the 5,6-unsaturation removed by hydrogenation using Adams' platinum oxide catalyst. The product was pyrolized by dropping into an atmosphere of nitrogen in an externally heated tube containing glass helices at 530 DEG C. The 2,3-dimethylenebicyclo-[2 : 2 : 1]-heptane was characterized by a Dials-Alder maleic anhydride adduct of melting-point 116-119 DEG C. The compounds of formula (1) may be polymerized (see Group IV (a)).ALSO:The two compounds represented by the formula where X is -H or -CH3 (see Group IV (b)) may be polymerized in the presence of a free radical-yielding catalyst. They may also be copolymerized with 1,3-butadiene, isoprene, styrene, a -methyl styrene or chlorostyrene. They may for example be polymerized in aqueous emulsion at 40-60 DEG C. in the presence of potassium persulphate, or in bulk at 90-110 DEG C. in the presence of benzoyl peroxide. They may also be polymerized suspended in water with a monomer-soluble catalyst to give granules of polymer. In an example, 2,3-dimethylenebicyclo - [2 : 2 : 1] - heptane was polymerized at 50 DEG C. in aqueous emulsion, using sodium oleate as emulsifying agent and potassium persulphate and n-dodecyl mercaptan as catalyst system.

Improvements in or relating to polymers of unsaturated bicyclic compounds

The Specification comprises compounds represented by formul (1) and (2): in which X represents -H or -CH3 and in formula (1) Y represents -CH2CH2-; -O-; or -CO-O- and in formula (2) Y represents -CH2-; -CH2-CH2-; or -O-. These compounds can be polymerized or copolymerized (see Group IV (a)). The monomeric compounds can be prepared by formation of the 2- and 3-methylene groups from the corresponding compounds containing substituted 2- and 3-methyl groups -CH2Z, where Z may be Cl, Br, I, OH or OCOR, R being an alkyl group preferably methyl, by removal of HZ. When Z is OH, dehydration can be carried out by heating in the presence of a catalyst such as alumina, aluminium silicate, phosphoric acid on silica gel, or silica-alumina, at a temperature between 65 DEG and 150 DEG C. When Z is halogen, dehydrohalogenation can be performed by heating under reflux with alcoholic caustic alkali. When Z is acyloxy the desired compound can be formed by pyrolysing the acyloxy derivative at a temperature between 450 DEG and 550 DEG C. These intermediate substituted 2,3-dimethyl compounds may themselves be prepared generally by a Diels-Alder condensation between a compound of the formula (3): in which X and Y are as defined as above, and maleic anhydride, maleic esters, maleic acid or fumaric acid. The resultant bicyclic compound contains a 5,6-olefinic bond which may be reduced to give the fully saturated compound if desired. The acid, anhydride or ester formation is converted into a 2,3-dimethylol formation either by reduction of the acid or anhydride with LiAlH4 or converting into an ester which may be reduced by the action of hydrogen and a copper chromite catalyst or by sodium and alcohol. The 2,3-dimethylol groups can be converted into the corresponding halogen or acyloxy derivative by normal halogenation, e.g. with a phosphorus halide, or acylation, e.g. with an acid anhydride. Another less general method of forming the intermediate substituted dimethyl compounds is by a Diels-Alder condensation between cyclopentadiene or 1-methyl cyclopentadiene and a butene-2 derivative which may be HOCH2CH = CHCH2OH; ClCH2CH = CH-CH2Cl or RCOOCH2CH = CHCH2COOR, the product being a 2,3-dimethyl-bicyclo-[2,2,1]-hept-5-ene, in which the methyl groups carry hydroxy, chloro or acyloxy groups and in which there may be a 1-methyl substituent. Particularly suitable starting compounds for the Dials-Alder condensation are cyclopentadiene; cyclohexadiene-1,3; furan; 2-methyl furan and 1,2-pyrone, or any compound which yields such materials under the reaction conditions, e.g. dicyclopentadiene may be substituted for the monomeric material. The compounds containing no 5,6-double bond may be prepared by reduction of the corresponding unsaturated compound at any stage prior to the formation of the methylene groups. In examples: (1) 1,3-cyclohexadiene was condensed with maleic anhydride, hydrogenated to give the saturated compound and reduced to the 2,3-dimethyl derivative with LiAlH4. This was acetylated and pyrolysed to yield 2,3 - dimethylenebicyclo - [2 : 2 : 2] - octane (b.p. 89 DEG C. at 58 mm.); (2) using the general method of Example (1) 7-oxabicyclo-[2 : 2 : 1]-heptane was prepared from furan; (3) 1 : 4-dichlorobutene-2 was condensed with cyclopentadiene (introduced as the dimer) and the resultant 2,3 - di - (chloromethyl) - bicyclo - [2 : 2 : 1]-heptane-5 was dehydrochlorinated by refluxing with alcoholic caustic potash to give 2,3 - dimethylanebicyclo - [2 : 2 : 1] - heptane - 5.ALSO:Compounds represented by formul (1) and (2): in which X is -H or -CH3 and in formula (1) Y is -CH2-CH2-, -O-, or -COO-; and in formula (2) is -CH2-, -CH2-CH2- or -O-(see Group IV (b)) may be polymerized in the presence of free radical-yielding catalysts. They may also be copolymerized with 1,3-butadiene, isoprene, styrene, a -methyl styrene and chlorostyrene. They may be polymerized at 40-60 DEG C. in aqueous emulsion in the presence of potassium persulphate or in bulk at 90-110 DEG C. in the presence of benzoyl peroxide. They may also be polymerized suspended in water using a monomer-soluble catalyst to obtain granules of polymeric material. In examples: (1) 2,3-dimethylenebicyclo[2 : 2]octane was polymerized in aqueous emulsion at 50 DEG C. using sodium oleate as emulsifying agent with potassium persulphate and n-dodecyl mercaptan as catalyst system; (2) and (3) 2,3-dimethylene-7-oxabicyclo-[2 : 2 : 1]-heptane and 2,3-dimethylenebicyclo-[2 : 2 : 1]-heptane-5 were similarly polymerized.

Improvements in or relating to unsaturated bicyclic compounds and their polymers

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Improvements in or relating to polymers of unsaturated bicyclic compounds

Improvements in or relating to unsaturated bicyclic compounds and their polymers