Patent GB-728954-A (GB)
Title: Improvements in or relating to organotin compounds and resins including same
IPC: C08K5/58
Filed: 1951-06-25
Abstract: A resinous composition comprises a vinyl chloride polymer or copolymer thereof with another ethylenically unsaturated compound, and from 0.2 to 5.0 per cent of an organo-tin compound of the general formula <FORM:0728954/IV (a)/1> wherein R1 represents an aliphatic hydrocarbon, aryl hydrocarbon or heterocyclic radical which may be substituted by an ether radical, said R1 radical being attached to the tin atom by means of a carbon atom, and R2 represents a hydrocarbon alkyl, hydrocarbon aryl or hydrocarbon aralkyl radical which may be substituted by an ether, carboxylic, carboxylic ester, thiol or hydroxy radical or by a halogen other than fluorine on an aromatic ring carbon atom or by fluorine on any carbon atom or by an aliphatic hydrocarbon radical containing an ethylenic or acetylenic linkage, or R2 is a heterocyclic radical, said radical R2 being attached to the sulphur atom by means of a carbon atom (see Group IV (b)).  The R2 radicals may be the same or different.  Suitable compounds for copolymerization with vinyl chloride are vinyl esters, e.g. vinyl bromide and fluoride, fatty acid vinyl esters such as vinyl acetate, chloroacetate and butyrate and vinyl alkyl sulphonates, vinyl ethers, e.g. vinyl ethyl ether, vinyl isopropyl ether and vinyl chloroethyl ethers, cyclic ethylenically unsaturated compounds, e.g. styrene, the mono- and poly-chlorostyrenes, coumarone, indene, vinyl naphthalenes, vinyl pyridines and vinyl pyrroles, acrylic acid and its derivatives, e.g. ethyl acrylate, methyl methacrylate, ethyl methacrylate, ethyl chloroacrylates, acrylonitrile, methacrylonitrile, diethyl maleate and diethyl fumarate, vinylidene compounds, e.g. vinylidene chloride, bromide and fluorchloride, unsaturated ethylenic hydrocarbons, e.g. ethylene, propylene or isobutene, allyl compounds, e.g. allyl acetate, allyl chloride and allyl ethyl ether, and conjugated and cross-conjugated ethylenically unsaturated compounds, e.g. butadiene, isoprene, chloroprene, 2,3 - dimethylbutadiene - 1,3, piperylene and divinyl ketone.  The resinous composition may be in the form of a thin flexible film and may contain other ingredients such as di-(2-ethyl-hexyl)-phthalate, tricalcium phosphate and a silicate pigment.ALSO:The invention comprises organo-tin compounds of the general formula <FORM:0728954/IV (b)/1> wherein R1 represents an aliphatic hydrocarbon, aryl hydrocarbon or heterocyclic radical which may be substituted by an ether radical, said R1 radical being attached to the tin atom by means of a carbon atom, and R2 is a hydrocarbon alkyl, hydrocarbon aryl or hydrocarbon aralkyl radical which may be substituted by an ether, carboxylic, carboxylic ester, thiol or hydroxy radical or by a halogen atom other than fluorine on any aromatic ring carbon atom or by fluorine on any carbon atom or by an aliphatic hydrocarbon radical containing an ethylenic or acetylenic linkage, or R2 is a heterocyclic radical, said radical R2 being attached to the sulphur atom by means of a carbon atom, and the preparation thereof by reacting at a temperature between 40 DEG  and 180 DEG  C. on organostannic acid of the formula <FORM:0728954/IV (b)/2> OH with a mercaptan of the formula R2-SH, R1 and R2 having the above significance.  The reaction may be carried out in a non-reactive solvent, e.g. hydrocarbon solvents such as benzene, toluene, xylene or petroleum ether, or chlorinated solvents such as carbon tetrachloride, trichloroethylene, tetrachloroethylene or hexachlorobutadiene. The radical R1 may represent the methyl, ethyl, n-butyl, iso-butyl, n-hexyl, 2-ethylhexyl, lauryl, n-hexadecyl, phenyl, a -naphthyl, 2-thienyl, xenyl and 2-(ethoxy)-ethyl and alkyl radicals derived from reduced coconut oil.  The Specification refers to a large number of mercaptans from which the R2 radicals are derived, and the R2 radicals may be the same or different.  In the examples compounds of the above general formula are prepared wherein the R1 radicals are methyl, ethyl, n-butyl, phenyl and 2-thienyl radicals and alkyl radicals derived from reduced coconut oil, and the R2 radicals are derived from n-butyl, sec.-amyl, octadecyl, t-dodecyl, a -naphthyl, p-cresyl and p-chlorobenzyl mercaptan, alkyl mercaptans where the alkyl radicals are derived from reduced coconut oil, 2-mercaptoethanol, methylbenzoate-2-thiol and a mixture 2- and 3-mercapto-alpha-pinenes.