GB968424A - Epithio ethers, their preparation and polymers - Google Patents

Abstract

The invention comprises epithio ethers having at least two <FORM:0968424/C1/1> groups, wherein R is hydrogen or a hydrocarbon radical, and at least one oxygen-ether linkage and derivatives thereof obtained by reaction with nucleophilic materials. The group attached to the epithio groups may be aliphatic, cycloaliphatic, aromatic or heterocyclic, saturated or unsaturated and may be substituted with halogen atoms and ester and sulphonyl radicals. The epithioethers may be prepared by the thermal dehydration of hydroxy-mercaptans, the treatment of 1,2-chlorothiols with alkaline solutions or the heating of a corresponding ethylenically unsaturated compound with sulphur or a compound that liberates sulphur on heating, but are preferably prepared by reacting an epoxyether with a thiocyanate, preferably an alkali metal thiocyanate or ammonium thiocyanate. Specified epoxyethers are those obtained by reacting bisphenol and epichlorohydrin in the presence of aqueous sodium hydroxide or by reacting glycerol, diethyl ether, boron trifluoride and epichlorohydrin. Other epoxyethers mentioned are the polymers and copolymers of allylic ethers of epoxy-containing alcohols. The epithioethers react with small quantities of nucleophilic material to form hard cross-linked water-insoluble infusible polymers (see Division C3) and with mono- and poly-functional reactants, e.g. amines, ammonia, acids, mercaptans and hydrogen sulphide, to produce monomeric derivatives.ALSO:Epithioethers having at least two <FORM:0968424/C3/1> groups, wherein R is hydrogen or a hydrocarbon radical, and at least one oxygen-ether linkage react, generally at around 25 DEG C. but preferably at 50 DEG to 150 DEG C., with small quantities, preferably 0.1% to 10%, of nucleophilic material to form hard cross-linked substantially water-insoluble infusible polymers. The groups attached to the epithio groups may be aliphatic, cycloaliphatic, aromatic or heterocyclic, saturated or unsaturated and may be substituted with halogen atoms and ester and sulphonyl groups. Specified nucleophilic materials are acids, acid anhydrides, mercaptans, amines, ammonia and certain specified metal salts. It may be desirable to employ solvents or diluents (for example ketones, esters or chlorinated hydrocarbons alone or in admixture with aromatic hydrocarbons and/or alcohols), including those which remain in the cured composition (for example diethyl phthalate, monoepithio compounds, monepoxides and cyano-substituted hydrocarbons), in the above reaction. The polymers so obtained may be further combined with polyepoxides, polyurethanes, resins, polythiopolymercaptans, polyaldehydes, polyols, synthetic oils, cellulose derivatives, vinyl polymers, bituminous materials, tars, asphalts, plasticizers, stabilizers and fillers to form compositions suitable for use as surfacing compositions, adhesives and laminating compositions.