Patent GB-633846-A (GB)
Title: New rubber derivatives and processes for their production
IPC: C08C19/30
Filed: 1946-11-22
Abstract: Synthetic rubber derivatives containing isocyanatoaryl or isothiocyanatoaryl groups are obtained by reacting carbonyl chloride or thiocarbonyl chloride with an amino synthetic rubber compound containing primary amino groups.  The amino derivatives may be obtained by the method of Specification 445,940 using aniline, orthotoluidine, 2 : 5-xylidine, 3 : 5 - xylidine, alpha - naphthylamine, metaphenylene diamine, 1 : 7-naphthalene diamine, 2 : 6-naphthalene diamine or 1 : 5-naphthalene diamine as the primary amine.  Preferably polyamines having amino groups on adjacent carbon atoms are not employed.  The synthetic rubbers may be polymers of isoprene, butadiene, or chlorobutadiene or copolymers of butadiene with styrene, acrylonitrile or isobutylene.  The amino rubber is preferably dissolved or dispersed as the hydrohalide or carbonate in an inert liquid such as toluene, xylene, chlorotoluene, chloroxylene, monochlorobenzene, or o-dichlorobenzene.  Optimum temperatures of reaction, lie between 100 DEG  and 160 DEG  C.  These derivatives, together with the corresponding derivatives obtained from natural rubber and guttapercha, may be reacted with compounds containing a reactive hydrogen atom, e.g. in hydroxyl, thiol, carboxyl, sulphonamide or amine groups, especially with polyvinyl alcohol, partially hydrolysed polyvinyl acetate and also with the polyethylene glycol adipate obtained by reacting 10 parts of adipic acid with 7.5 parts of ethylene glycol at 150 DEG  C.  These compounds are insoluble in rubber solvents but may swell slightly.ALSO:Rubber derivatives containing isocyanatoaryl or isothiocyanatoaryl groups are obtained by reacting carbonyl chloride or thiocarbonyl chloride with an amino-natural or synthetic rubber compound containing primary amino groups.  The amino derivative may be obtained by the method of Specification 445,940 using aniline, orthotoluidine, 2 : 5 xylidine, 3 : 5 xylidine, alpha naphthyl-amine, metaphenylene diamine, 1 : 7 naphthalene diamine, 2 : 6 naphthalene diamine or 1 : 5 naphthalene diamine as the primary amine.  Preferably polyamines having amino groups on adjacent carbon atoms are not employed. The rubbers may be Hevea rubber, balata or guttapercha, or polymers of isoprene, butadiene or chlorobutadiene or copolymers of butadiene with styrene, acrylonitrile, or isobutylene.  The amino rubber is preferably dissolved or dispersed as the hydrohalide or carbonate in an inert liquid such as toluene, xylene, chlorotoluene, chloroxylene, monochloro-benzene or o-dichlorobenzene.  Optimum temperatures of reaction lie between 100 and 160 DEG  C.  The derivatives are soluble in benzene, toluene, naphtha and carbon tetrachloride and may be used as such for bonding rubber to steel, aluminium or to a textile fabric, thread or cord.  They may also be used as a vulcanizing agent for rubber. The derivatives may be reacted with compounds containing a reactive hydrogen atom, e.g. in hydroxyl, thiol, carboxyl, sulphonamide or amino groups, especially with polyvinyl alcohol, partially hydrolysed polyvinyl acetate and also with the polyethylene glycol adipate obtained by reacting 10 parts of adipic acid with 7.5 parts of ethylene glycol at 150 DEG C.  These compounds are insoluble in rubber solvents but may swell slightly.