GB728953A - Improvements in or relating to organotin compounds and resins including same - Google Patents

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:0728953/IV (a)/1> wherein R1 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 or by fluorine on any carbon atom or by an aliphatic hydrocarbon radical containing an ethylenic or acetylenic linkage, or R1 is a heterocyclic radical, said R1 radical being attached to the sulphur atom by means of a carbon atom, and R2 represents an aliphatic hydrocarbon, aryl hydrocarbon or heterocyclic radical which may be substituted by an ether radical, said R2 radical being attached to the tin atom by means of a carbon atom (see Group IV (b)). Both the R1 radicals or 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 polychlorostyrenes, 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 fluorochloride, unsaturated ethylenic hydrocarbons, e.g. ethylene, propylene and 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-ethylhexyl)-phthalate, tricalcium phosphate and a silicate pigment.ALSO:<FORM:0728953/IV (b)/1> wherein R1 represents a hydrocarbon alkyl, hydrocarbon aryl or hydrocarbon aralkyl 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 R1 is a heterocyclic radical, said R1 radical being attached to the sulphur atom by means of a carbon atom, and R2 represents an aliphatic hydrocarbon, aryl hydrocarbon or heterocyclic radical which may be substituted by an ether radical, said R2 radical being attached to the tin atom by means of a carbon atom, and the preparation thereof by reacting at a temperature in the range of 40 DEG to 180 DEG C. a mercaptan of the formula R1SH and a stannone of the formula <FORM:0728953/IV (b)/2> wherein R1 and R2 have the above significance. The organo-tin compounds may also be prepared by reacting at a temperature in the range of 60 DEG to 200 DEG C. an alkali metal mercaptide of the formula R2S-alk and a diorgano-tin halide of the formula <FORM:0728953/IV (b)/3> wherein R1 and R2 have the above significanec and alk represents an alkali metal. Non-reactive solvents may be used in either of the above processes, e.g. hydrocarbon solvents such as benzene, toluene, xylene or petroleum ether, or chlorinated solvents such as carbon tetrachloride, trichloroethylene, tetrachloroethylene or hexachlorobutadiene, or oxygenated solvents such as diethyl ether. The radicals R2 may be the same or different and may represent methyl, ethyl, isobutyl, n-butyl, n-hexyl, lauryl, hexadecyl, phenyl b -naphthyl, 2-thienyl, 2-furyl, xenyl and 2-ethoxyethyl radicals or alkyl radicals derived from reduced coconut oil. The Specification refers to a large number of mercaptans from which the R1 radicals are derived, and the R1 radicals may be the same or different. In the examples, compounds of the above general formula are prepared wherein the R1 radicals are derived from butyl, amyl, t-dodecyl, hexadecyl, t-hexadecyl, octadecyl, tridecyl, benzyl, alkylbenzyl, p-chlorobenzyl, phenyl, p-cresyl and a - and b -naphthyl mercaptans, methylbenzoate-2-thiol, alpha-thiophenethiol 2 - { 2 - (2 - octylphenoxy) ethoxy } ethane thiol, 2-mercaptoethanol, thiosalicylic acid, the mercaptans obtained by the addition of hydrogen sulphide to triisobutylene, tetraisobutylene, 8-carbon olefines, and mixtures of 8-, 12- and 14-carbon olefines, and alkyl mercaptans where the alkyl radicals are derived from reduced coconut oil, and the R2 radicals represent methyl, n-butyl, phenyl and 2-thienyl radicals and alkyl radicals derived from reduced coconut oil.