US2244263A - Procedure for the manufacture of caoutchouc products - Google Patents

Description

Patented June 3, 1941 PROCEDURE FOR THE MANUFACTURE OF CAOUTCHOUO PRODUCTS Walther Schrauth, Berlin-Dahlem,

Berlin, Germany, assignors,

Morgenstern,

and Stefan by mesne assignments, to Patchem A.-G. Zur

Beteiligung An Patenten Und Sonstigen Erflndungsrechten Auf Chemische Verfahren," Zurich, Switzerland, a corporation of Switzerland No Drawing. Application August 10, 1936, Serial rmany August 10, 1935 No. 95,284. In Ge 3 Claims. (CL 260-761) It has been found that substituted aromatic compounds containing no -less than 12 carbon atoms and at least 1 hydroxyl group are excellent softening and plastiiying agents for natural, regenerated and artificial caoutchouc as well as for caoutchouc masses. Such compounds are e. g. the phenols, naphthols and the like or their homologues respectively substituted by allqrl-, aralkyl-, arylor cycloalkyl-residues. As such may be mentioned e. g. the benzyl-phenol, methylcyclohexyl-cresol, menaphthyl-cresol, decalylxylenol and the like. In a similar manner one may also employ their partially or entirely hydrogenized products such as octadecylmethylcyclohexanol, the octyl-actetralol (2), the lauryldecahydronaphthol (2), the 4,4-dihydroxy-dicyclo-hexyl, the perhydrogenized 2,2- dihydroxy-l,l-dinaphthyl, the perhydrogenized 4,4-dihydroxy-diphenyl-methane, the perhydrogenized 2,2 dihydroxy-1,1 dinaphthyl-methylmethane, the perhydrogenized menaphthylcresol, a perhydrogenized product of the probable iormula tion-product, resumed condensation after the.

prior water-separation with cresol and subsequent hydrogenation.

Also the products obtainable at the reduction and preferably by the catalytic h pressure reduction of resins, resin esters, resinic acids, and being of an alcoholic character, have proved to be particularly advantageous. Good for the purpose are e. g. the resinic alcohol of the acetylsaponification number 168 dropping point of 58 and boiling point of 190-230 at a 3 mm.-mereury-pressure, and obtainable from commercial colophony by high-pressure reduction, further the damar-resin-alcohol (acetyl-saponiflcatlon,

number 120, boiling point 88), and the resinic alcohol (acetyl-saponiflcation number 122, boiling point 136) obtainable from Congo-copal by the high-pressure reduction.

By the alcoxylation or the converting into acetals or into esters the aforedescribed products may moreover be varied at ones wishes such as to be applicable also for special purposes without ado. Such products are e. g. the acetic acid ester, the lactic acid ester, the stearic acid ester, the adipic acid ester and the phthalic acid ester and alkyl ether as well as the cyclo-alkyl ether of the aforedescribed resin-alcohols, such as damar-resin-alcohol-butyl ether, Congo-copalalcohol-cetyl ether, colophony-resin-alcoholmethylcyclohexyl ether.

Sometimes, e. g. in working artificial caoutchouc, it is recommendable to use the abovementioned products in combination with a suitable solvent such as pine oil, decamphorated oil of turpentine, hydrogenized hydrocarbons, tetrahydro-naphthalene, decahydronaphthalene, hydrogenized phenols such as dimethyl-cyclohexanol, or a mixture of those solvents.

The technical advantage offered by the proposed novel products at the reaction upon natural, regenerated and artificial caoutchouc and caoutchouc masses, is to be seen in the fact that they are excellent plastiflers especially for artificial caoutchouc. Already in working the caoutchouc on the mixing cylinder they facilitate extraordinarily its absorbing capacity for most heterogeneous additional stufis. To the vulcanized products they impart a great elasticity together with a good resistance and a remarkable ductility. Moreover the products applied according to the present invention, which are generally colourless up to light-yellow and which according to the selection of the initial materials are of a viscous, thickly liquid up to a solid character, distinguished themselves by a great fastness to chemical and physical reactions and moreoveras far as hydrogenation products are accrued-by a very remarkable fastness to Example 1 A homogeneous mixture which allows of being easily worked on mixing cylinders, is obtained from:

Parts by weight First-latex-crape-caoutchouc 55) Kaolin 30 Menaphthyl-cresol or oi. an alkyl-phenol containing a rammed alkyl group with 8-10 0. atoms, or their hydrogenation- The mixture is vulcanized for 45' minutes at 140 C.

' Example 2 In the same way as indicated in Example 1 one mixes thoroughly in the mixing cylinder:

Parts Smoked sheet-caoutchouc 40 Regenerated caoutchouc 25 Chalk-" -2 Damar-resin alcohol or phthalate of the resinic alcohol obtained from Congo-copal,

mixed with pine oil (60:40) 5 Zinc oxide 5 sulfur 1.5

Mercapto-benzothiazol 0.5

whereupon the mixture is vulcanized for 40 minutes at 135 C.

Example 3 One mixes in the aforesaid manner:

Parts by weight Smoked sheet-caoutchouc 20 Synthetic butadine-caoutchouc 20 Gas-soot Silex-white 10 Zinc oxide 5 Resinic alcohol (obtained by catalytic highpressure reduction from commercial colophony) or its acetate or its butyl-ether 3 Sulfur 2 Viflcanization-accelerator 0.5 The mixture is vulcanized for 1 hour at C.

What we claim is:

1. A plastic composition comprising caoutchouc and, as a plasticizer, resinic alcohol.

2. The method of producing plastic masses which comprises combining with caoutchouc as a plasticizer, a compound oi. the group consisting of resinic alcohols, esters oi resinic alcohols with acids of the group consisting of acetic, lactic, stearic, adipic and phthalic acids, alkyl ethers and acetals oi resinic alcohols and cyclo-alkyl ethers of resinic alcohols.

3. A plastic composition comprising caoutchouc and, as a plasticizer, a compound oi the group consisting of resinic alcohols, esters of resinic alcohols with acids of the group consisting of acetic, lactic, stearic, adipic and phthalic acids. alkyl ethers and acetals of resinic alcohols, and cyclo-alkyl ethers of resinic alcohols.

WALTHER SCHRAUTH. SI'EFAN MORGENS'I'ERN.

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