GB820451A - Vulcanization of hydroxy-containing polymers - Google Patents

Abstract

A millable and vulcanizable rubber mix comprises a copolymer of a diene and a hydroxy-containing monomer and as the vulcanizing agent therefor the reaction product of a polyisocyanate and an active hydrogen-containing compound. The dienes may be 1,3-butadiene; isoprene; 2,3-dimethyl-1,3-butadiene; piperylene; 2-methyl-1,3-pentadiene; chloroprene; methylpentadiene; methoxybutadiene; ethoxybutadiene; 2-cyanobutadiene and 2-methyl-3-cyanobutadiene. The hydroxy containing monomers may be 2-phenyl-4-hydroxy-1-butene; 2 - (4 - chlorophenyl) - 4 - hydroxy - 1 - butene; 2 - (2 - bromo - 4 - methylphenyl) - 4 - hydroxy - 1 - butene; 2 - (2 - methoxyphenyl) - 4 - hydroxy - 1 - butene; 2 - (2,4,6 - trimethyl-phenyl) - 4 - hydroxy - 1 - butene; dimethylethynylcarbinol; hydroxyethyl acrylates and methacrylates; hydroxyethylstyrene; 2 - hydroxyethyl - 5 - vinylpyridine; N - hydroxy - ethyl acrylamide and N-methylol acrylamide. The hydroxy monomer may also include a compound containing an active vinylidene group such as styrene; parachlorostyrene; paramethoxystyrene methyl acrylate; ethyl acrylate; methyl methacrylate; ethyl methacrylate; butyl methacrylate; acrylonitrile; methacrylonitrile; methacrylamide; methyl isopropenyl ketone; methyl vinyl ketone; methyl vinyl ether; vinyl acetate; vinyl chloride; vinylidene chloride; vinylfurane; vinylcarbazole; vinylacetylene or 2-methyl-5-vinylpyridine. The polyisocyanates may be m-phenylene diisocyanate; p-phenylene diisocyanate; hexamethylene diisocyanate; m-tolylene diisocyanate; p-tolylene diisocyanate; p,p1-diphenylmethane diisocyanate; p,p1-diphenyl diisocyanate; diphenyl - 3,31 - dimethyl - 4,41-diisocyanate; 2 - chloropropane diisocyanate-1,3; diphenyl - 3,31 - di - methoxy - 4,41 - diisocyanate; 2,21-diisocyanate diethyl ether; 3-(diethylamine)-pentane-diisocyanate-1,5; 1,5-naphthylene diisocyanate; pentamethylene diisocyanate; tetramethylene diisocyanate; octamethylene diisocyanate; ethylene diisocyanate; propylene - 1,2 - diisocyanate; cyclohexylene - 1,2 - diisocyanate; xylylene - 1,4 - diisocyanate; and benzene-1,2,4-triisocyanate. The active hydrogen-containing compounds may be phenol: o-, m- and p-cresol; di-n-butylamine; diphenylamine; piperidine; morpholine; phenyl-beta-naphthylamine; N - methylacetamide; N-ethyl valeramide; N-methyl-2-naphthamide; diacetamide; acetanilide; N-phenyl benzamide; succinamide; phthalimide and malonimide. In examples a 75/25 butadiene/2-phenyl-4-hydroxy-1-butene copolymer was vulcanised with the aid of the reaction products of hexamethylene diisocyanate, m-tolylene diisocyanate or p,p1-diphenylmethane diisocyanate with phenol; diphenylamine; acetanilide; p,p1-dimethoxy diphenylamine or phthalimide.