Patent GB-800168-A (GB)
Title: Hydrocarbontin isodithiocarbamates
IPC: C07F7/22
Filed: 1956-10-19
Abstract: Hydrocarbon-tin isodithiocarbamates of formula <FORM:0800168/IV (a)/1> where n is an integer from 1 to 3, R, R1 and R11 are the same or different and are hydrocarbon radicals and when n is 2 or 3, R11 may represent different hydrocarbon radicals, are used as stabilizers in synthetic resin and rubber compositions (particularly chlorine containing vinyl resin compositions containing plasticisers) and as antioxidants, antiozonants and curing accelerators in rubber compositions, e.g. GRS rubber, neoprene and natural rubber. Compounds specified include dimethyl - tin bis - S - (N - butyl - S1 - benzyl isodithiocarbamate), dibutyl - tin bis - S - (N - benzyl - S1 - benzyl isodithiocarbamate) and triphenyl - tin - S - cyclohexyl-N-cyclohexyl isodithiocarbamate.  The Specification includes the results of stability tests carried out on a polyvinyl chloride composition containing dioctyl phthalate as plasticiser and stabilized by the first four compounds specified above.ALSO:The invention comprises hydrocarbon-tin isodithio carbamates of formula <FORM:0800168/IV (b)/1> where n is an integer from 1 to 3, R, R1-R11 are the same or different and are hydrocarbon radicals and when n is 2 or 3, R11 may represent different hydrocarbon radicals.  The hydrocarbon radicals may be alkyl, cycloalkyl, aryl, aralkyl, alkaryl, alkenyl, alkinyl or cycloalkenyl.  The compounds of the invention may be prepared by reacting an isodithiocarbamic acid with a hydrocarbon-tin oxide or chloride, such as dimethyl-tin oxide, diethyl-tin oxide, dipropyl-tin oxide, di-n-butyl-tin oxide, di-isobutyl-tin oxide, di-isoamyl-tin oxide, diphenyltin oxide, dimethyl-tin chloride, diethyl-tin chloride, ethyl n-propyl-tin dichloride, di-n-propyl-tin dichloride, di-tert.-butyl-tin dichloride, di - iso - butyl-tin dichloride, di - iso - amyltin dichloride, di-tert.-amyl-tin dichloride, trimethyl-tin chloride, triethyl-tin chloride, tri-n-butyl-tin chloride, tri-iso-butyl-tin chloride, tri-tert.-butyl-tin chloride, tri-iso-amyl-tin chloride, diethyl - n - propyl - tin chloride, diethyl - n - amyl - tin chloride, methyl - tin trichloride, triphenyl-tin chloride, tri-p-tolyl-tin chloride, trim-tolyl-tin chloride, tri-o-tolyl-tin chloride, tri-2,5-xylyl-tin chloride, tri-b -naphthyl-tin chloride, tri-benzyl-tin chloride, tri-cyclohexyl-tin chloride, diphenyl-tin dichloride, di-o-tolyl-tin dichloride, di-p-tolyl-tin dichloride, phenylethyl-tin dichloride, dibenzyl-tin dichloride, dicyclohexyl-tin dichloride, phenyl-tin trichloride, o-tolyl-tin trichloride and p-tolyl-tin trichloride.  Isodithiocarbamic acids may be prepared by reacting a primary amine with carbon disulphide and a metal (preferably an alkali-metal) hydroxide and then reacting the metal dithiocarbamate so formed with an organic halide: <FORM:0800168/IV (b)/2> The primary amine may be alkyl, alkenyl, alkinyl, cycloalkyl, aryl, or aralkyl.  Similarly the organic halide may be an alkyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkenyl or an alkinyl chloride.  Lists of suitable amines and organic chlorides are included.  In an example N-butyl S1-benzyl iso-dithiocarbamic acid is prepared by reacting butylamine with carbon disulphide in the presence of caustic soda, and reacting the product with benzyl chloride.  The so-formed N-butyl S1-benzyl isodithiocarbamic acid is reacted with dimethyl-tin oxide in toluene solution to give dimethyl-tinbis-S(N-butyl S1-benzyl isodithiocarbamate).  Other examples describe the preparation of the following compounds: dibutyl-tin-bis-S(N-benzyl - S1 - benzyl isodithiocarbamate), dibutyl - tin - bis - S(N - cyclohexyl - S1 - benzyl isodithiocarbamate), and dibutyl-tin-S,S-bis-(N-butyl-S1-benzyl isodithiocarbamate).