Patent GB-646741-A (GB)
Title: Improvements in accelerators
IPC: C08K5/00
Filed: 1948-03-24
Abstract: N-beta-cyanoethyl thiocarbamo sulphonamides having the general formula <FORM:0646741/IV (a)/1> where R is a group from acyclic, alicyclic, aryl, and aralkyl hydrocarbons and beta-cyanoethylene and R1 and R11 are groups from hydrogen, acyclic, alicyclic, and aralkyl hydrocarbons, are used in synthetic rubbers as accelerators. Typical sulphonamides are N-beta - cyanoethyl N - ethyl thiocarbamo sulphonamide, N - beta - cyanoethyl N, N1 - di-n - butyl thiocarbamo sulphonamide, N - n-butyl N - beta - cyanoethyl N1 - cyclohexyl thiocarbamo sulphonamide, di - beta - cyanoethyl thiocarbamo sulphonamide, N-n-butyl N-beta cyanoethyl thiocarbamo sulphonamide, N - ethyl N - beta - cyanoethyl N - cyclohexyl thiocarbamo sulphonamide, N-n-butyl N-betacyanoethyl N1,N1-diethyl thiocarbamo sulphonamide, N-beta-cyanoethyl N-ethyl N1-n-butyl thiocarbamo sulphonamide, and N-beta-cyanoethyl N,N1,N1-triethyl thiocarbamo sulphonamide.  In examples, five of the above specified sulphonamides are separately mixed with butadiene-styrene or butadiene-acrylonitrile copolymer, sulphur, coal tar softener, carbon black and zinc oxide, and conventional accelerators such as diphenyl guanidine, mercaptobenzthiazole or dibenzthiazole sulphide may also be used.ALSO:N-beta-cyanoethyl thiocarbamo sulphenamides having the general formula <FORM:0646741/IV (b)/1> where R is a group from acyclic, alicyclic, aryl, and aralkyl hydrocarbons and beta-cyanoethylene, and R1 and R11 are groups from hydrogen, acylic, alicyclic and aralkyl hydrocarbons are used as rubber accelerators as described in Group V.  In an example N-beta-cyanoethyl N-ethyl thiocarbamo sulphenamide is prepared by treating with an excess of monochloramine the dithiocarbamate obtained by reacting together N-beta-cyanoethyl ethylamine, sodium hydroxide and carbon disulphide. In further examples the following sulphenamide are prepared by similar methods: N-beta-cyanoethyl N,N1-n-dibutyl thiocarbamo sulphenamide, N-n-butyl N-beta-cyanoethyl N1-cyclohexyl thiocarbamo sulphenamide, di-beta-cyanoethyl thiocarbamo sulphenamide, N-n-butyl N-beta cyanoethyl thiocarbamo sulphenamide, N-ethyl N-beta-cyanoethyl N1-cyclohexyl thiocarbamo sulphenamide, N-n-butyl N-beta cyanoethyl N1,N1-diethyl thiocarbamo sulphenamide, N-beta-cyanoethyl N-ethyl N1-n-butyl thiocarbamo sulphenamide and N-beta-cyanoethyl N,N1,N1-triethyl thiocarbamo sulphenamide.ALSO:N - beta - cyanoethyl thiocarbamo sulphoamides having the general formula <FORM:0646741/V/1> where R is a group from acyclic, alicyclic, aryl, and aralkyl hydrocarbons and beta-cyanoethylene; and R1 and R11 are groups from hydrogen, acyclic, alicyclic, and aralkyl hydrocarbons are used in natural and synthetic rubbers as accelerators.  The preparation of the following sulphonamides according to the method described in Group IV (b) is given: N - beta - cyanoethyl N - ethyl thiocarbamo sulphonamide, N - beta - cyanoethyl N, N1-di - n - butyl thiocarbamo sulphonamide, N - n - butyl N - beta - cyanoethyl N1 - cyclohexyl thiocarbamo sulphonamide, di - betacyanoethyl thiocarbamo sulphonamide, N - n-butyl N-beta cyanoethyl thiocarbamo sulphonamide, N - ethyl N - beta - cyanoethyl N-cyclohexyl thiocarbamo sulphonamide, N -n-butyl N - beta - cyanoethyl N1,N1 - diethyl thiocarbamo sulphonamide, N - beta - cyanoethyl N - ethyl N1 - n - butyl thiocarbamo-sulphonamide, and N-beta-cyanoethyl N,N1,N1-triethyl thiocarbamo sulphonamide.  In addition many other such sulphonamides are specified.  In examples 5 of the above specified sulphonamides are separately mixed with butadiene-styrene copolymer, sulphur, coal tar softener, carbon black and zinc oxide. Butadiene-acrylonitrile copolymer may replace the above copolymer and conventional accelerators such as diphenyl guanidine, mercaptobenzthiazole or dibenzthiazole sulphide may also be used.