Patent GB-676248-A (GB)
Title: Improvements in or relating to a method for the vulcanization of rubber
IPC: C08K5/00
Filed: 1950-01-17
Abstract: Synthetic rubbers are vulcanized by heating in the presence of sulphur and a compound having the structure <FORM:0676248/IV (a)/1> where M is a member of the group consisting of hydrogen atoms, metals, and ammonium and alkyl-, cycloalkyl-, and aralkyl-substituted ammonium groups; and R1 and R2 are alkyl, cycloalkyl, hydroxyalkyl, cyanoalkyl, aralkyl, carbamyl or thiocarbamyl radicals and R1 or R2 but not both may be hydrogen.  R1 and R2 may be methyl, ethyl, 2-cyanoethyl, 2-hydroxyethyl, propyl, butyl, 2-cyanobutyl, amyl, benzyl, phenethyl, cyclohexyl, or methyl cyclohexyl radicals.  M may be zinc, magnesium, ammonia, methylamine, ethylamine, isopropylamine, butylamine, benzylamine, cyclohexylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, methyl propylamine, N-methyl cyclohexylamine, dicyclohexylamine, dibenzylamine, piperidine, trimethylamine, or triethylamine. Specified compounds are N,N-dibutyl maleamic acid, N-cyclohexylmaleamic acid, N,N - dicyclohexyl maleamic acid, N - ethyl phthalamic acid, N-butyl phthalamic acid, N,N-di-isopropyl phthalamic acid, N,N-dibutyl phthalamic acid, N,N - dicyclohexyl phthalamic acid, zinc salt of N-butyl maleamic acid, zinc salt of N-ethyl phthalamic acid, zinc salt of N-butyl phthalamic acid, zinc salt of N,N-dicylohexyl phthalamic acid, isopropylamine salt of N-isopropyl maleamic acid, butyl amine salt of N-butyl maleamic acid, dicyclohexylamine salt of N,N-dicyclohexyl maleamic acid, ethylamine salt of N-ethyl phthalamic acid, isopropylamine salt of N-isopropyl phthalamic acid, butylamine salt of N-butyl phthalamic acid, and the dicyclohexylamine salt of N,N-dicyclohexyl phthalamic acid.  These compounds may be prepared according to the methods set out in Group IV (b).  In examples, the activating properties of some of these compounds is illustrated on mixes consisting of GR-S, carbon black, zinc oxide, sulphur, mercaptobenzthiazole, and hydrocarbon oil plasticizer.ALSO:Accelerators for natural or synthetic rubber having the structure <FORM:0676248/IV (b)/1> where M is a member of the group consisting of hydrogen, metals, ammonium, and alkyl-, cycloalkyl-, and aralkyl-substituted ammonium groups; and where R1 and R2 are alkyl, cycloalkyl, aralkyl, or carbamyl radicals, and R1 or R2 but not both may be hydrogen may be produced by reacting the appropriate amine with phthalic anhydride, and then if necessary, further reacting with the appropriate soluble metal salt.  R1 and R2 may be methyl, ethyl, 2-cyano ethyl, 2-hydroxyethyl, propyl, butyl, 2-cyanobutyl, amyl, benzyl, phenethyl, cyclohexyl, methyl cyclohexyl, or thiocarbamyl radicals.  The salt forming groups may be zinc, magnesium, ammonia, methyl amine, ethyl amine, isopropyl amine, butyl amine, benzylamine, cyclohexyl amine, dimethyl amine, diethyl amine, diisopylamine, dibutyl amine, methyl propyl amine, N-methyl cyclohexylamine, dicyclohexylamine, dibenzylamine, piperidine, trimethyl amine, or triethyl amine.  Specified compounds which may be produced are N,N-dibutyl maleamic acid, N-cyclohexyl maleamic acid, N,N-dicyclohexyl maleamic acid, N-ethyl phthalamic acid, N-butyl phthalamic acid, N,N-diisopropyl phthalamic acid, N,N-dibutyl phthalamic acid, N,N-dicyclohexyl phthalamic acid, zinc salt of N-butyl maleamic acid, zinc salt of N-ethyl phthalamic acid, zinc salt of N-butyl phthalamic acid, zinc salt of N,N-dicyclohexyl phthalamic acid, isopropyl amine salt of N-isopropyl maleamic acid, butyl amine salt of N-butyl maleamic acid, dicyclohexyl amine salt of N,N-dicyclohexyl maleamic acid, ethyl amine salt of N-ethyl phthalamic acid, isopropyl amine salt of N-isopropyl phthalamic acid, butyl amine salt of N-butyl phthalamic acid, and dicyclohexyl amine salt of N,N-dicyclohexyl phthalamic acid.