Patent GB-800295-A (GB)
Title: Halogen-containing synthetic resins stabilised by hydrocarbontin dithiocarbamates
IPC: C08K5/58
Filed: 1956-10-31
Abstract: Halogen-containing synthetic resin compositions may be stabilized by incorporation therein of a hydrocarbon-tin dithiocarbamate of formula <FORM:0800295/IV (a)/1> where n is an integer from 1 to 3, R and R11 are the same or different hydrocarbon groups, R1 is the same as or different from R and R11 and is a hydrogen atom or a hydrocarbon group, R1 and R11 may be cyclized to form a ring containing a secondary nitrogen atom and when n is 2 or 3, R may represent different hydrocarbon radicals.  Specified stabilizers include dimethyl-tin bis-(N-dibutyl dithiocarbamate), dimethyl-tin bis-(N-cyclohexyl dithiocarbamate), dimethyl-tin bis-(N-phenyl dithiocarbamate), dimethyl-tin bis-(N-benzyl dithiocarbamate), dibutyl-tin di-(N-phenyl dithiocarbamate), dibutyl-tin bis-(N-butyl dithiocarbamate), dibutyl-tin bis-(N-cyclohexyl dithiocarbamate), dibutyl-tin bis-(N,N-dibutyl dithiocarbamate, tributyl-tin (N-methyl dithiocarbamate, dibutyl-tin bis-[N,N-di-(2-ethylhexyl)-dithiocarbamate], triethyl-tin (N-methyl dithiocarbamate).  The resin composition may contain a plasticiser, e.g. dioctyl phthalate.  Specified resins include polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with (a) vinyl esters of aliphatic carboxylic acids, e.g. vinyl acetate; (b) esters, nitriles and amides of unsaturated carboxylic acids such as acrylic and methacrylic acids; (c) diene compounds; (d) unsaturated dicarboxylic acids and their esters or their anhydrides, e.g. diethyl maleate, diethyl fumarate or maleic anhydride; after-chlorinated polymers and copolymers of vinyl chloride; vinyl chloridevinylidene chloride copolymers, and many others.ALSO:Hydrocarbon-tin dithiocarbamates of formula <FORM:0800295/IV (b)/1> wherein R and R11 are the same or different hydrocarbon groups, R1 is the same as or different from R and R11 and is a hydrocarbon group or hydrogen, and R1 and R11 may be cyclized to form a ring containing a secondary nitrogen atom and n is an integer from 1 to 3, may be prepared by reacting a hydrocarbon-tin compound containing a readily removable functional group bound to tin such as the oxide or halide with carbon disulphide and a primary or secondary amine.  They may also be prepared by reacting an aqueous mixture of a primary or secondary amine and sodium hydroxide with carbon disulphide to form the alkali metal salt of the desired dithiocarbamic acid which in its turn is reacted with a hydrocarbon-tin halide.  Lists of suitable hydrocarbon-tin reagents and of amines are included in the Specification.  The reaction products may be used as stabilizers in halogen containing synthetic resin compositions (see Group IV (a)). Example 1 describes the preparation of dimethyl-tin-bis-(N-dibutyl dithiocarbamate) by reacting dibutylamine and caustic soda with carbon disulphide and reacting the product with dimethyl-tin dichloride.  Other examples describe the preparation of dimethyl-tin-bis-(N-cyclohexyl dithiocarbamate), dimethyl - tin - bis - (N - phenyl dithiocarbamate), dimethyl - tin - bis - (N - benzyl dithiocarbamate), dibutyl-tin-di-(N-phenyldithiocarbamate), dibutyl-tin-bis-(N-butyl dithiocarbamate), dibutyl - tin - bis - (N - cyclohexyl dithiocarbamate), dibutyl-tin-bis-(N,N-dibutyl dithiocarbamate), tributyl - tin - (N - methyl dithiocarbamate), dibutyl - tin - bis - [N,N - di - (2 - ethyl - hexyl) - dithiocarbamate], triethyl - tin - (N - methyl dithiocarbamate) and of the dibutyl-tin salts of the dithiocarbamic acids substituted on the nitrogen atom by mixed long-chain unsaturated primary and secondary amines derived from unsaturated fats.