Patent GB-887543-A (GB)
Title: Process for the production of linear, hardenable bis-glycidal ethers of carbonic acid esters
IPC: C08G59/22
Filed: 1959-12-07
Abstract: New hardenable compounds are the bis-glycidyl ethers of mono- or poly-carbonate esters of formula <FORM:0887543/IV (a)/1> wherein n=0 to about 40 and R1, R2 and R3 are the residues of an aliphatic, cycloaliphatic or aromatic dihydroxy compound, at least one of the residues being that of an aromatic dihydroxy compound.  The hydroxy-terminated esters may be made by reacting an aromatic dihydroxy compound (optionally in admixture with an aliphatic or cycloaliphatic dihydroxy compound) with an aliphatic or aromatic diester of carbonic acid or with phosgene. Epoxidation of the esters may be effected by reacting them with epichlorhydrin in the presence of a hydrogen chloride binding agent and either a solvent for the organic ingredients of the reaction mixture or a liquid dispersing medium.  Alternatively, if the phosgenation method is used to make the esters, the reaction with the epichlorhydrin may be effected concurrently with the phosgenation.  Specified aromatic dihydroxy compounds are dihydroxy substituted benzene, naphthalene, diphenyl, tetrachlorobenzene, and diphenylalkanes, -cycloalkanes, -ether, -sulphide, -sulphoxide, -sulphone and -ketone.  Specified other dihydroxy compounds are alkane- and cycloalkane-diols, oxy- and thioalkylene glycols, xylylene glycols, 2,2-(4,41-dihydroxydicyclohexyl)-propane, 4,41-dihydroxydicyclohexylmethane and 2,6-dihydroxydecahydronaphthene.  The bis-glycidyl ethers are soluble in methylene chloride, chloroform, ethylene chloride, benzene, toluene, dioxane, tetrahydrofurane, ethyl acetate, acetone, cyclohexane and dimethyl formamide.  They may be hardened by basic or acid catalysts, e.g. alkali metal hydroxides, amines, amides, polycarboxylic acids, polycarboxylic anhydrides (e.g. phthalic anhydride) or the sodium salt of bis-phenol A.  They may be used in the preparation of lacquers, binding agents, adhesives, moulded articles and foams.  Examples describe the preparation of and subsequent hardening of the bis-glycidyl ethers of polycarbonates of bis-phenol A, 2,2-(4,41-dihydroxy-diphenyl)-butane and 4,41-dihydroxy -3,31-dimethyl-diphenyl -sulphide.ALSO:The invention comprises bis-glycidyl ethers of carbonic acid esters of formula <FORM:0887543/IV (b)/1> wherein n is 0 to about 40 and R1, R2 and R3 are the residues of aliphatic, cycloaliphatic or aromatic dihydroxy compounds, at least one of the residues being that of an aromatic dihydroxy compound.  The hydroxy-terminated ester may be made by reacting an aromatic dihydroxy compound (optionally in admixture with an aliphatic or cycloaliphatic dihydroxy compound) with an aliphatic or aromatic diester of carbonic acid or with phosgene. Epoxidation of the esters may be affected by reacting them with epichlorhydrin in the presence of a hydrogen chloride binding agent and either a solvent for the organic ingredients of the reaction mixture or a liquid dispersing medium.  Alternatively, if the phosgenation method is used to make the esters, the reaction with the epichlorhydrin may be effected concurrently with the phosgenation.  Specified aromatic dihydroxy compounds are dihydroxy substituted benzene, naphthalene, diphenyl, tetrachlorobenzene, and diphenyl-alkanes, -cycloalkanes, -ether, -sulphide, -sulphoxide, -sulphone and ketone.  Specified other dihydroxy compounds are alkane- and cycloalkane diols, oxy- and thioalkylene glycols, xylylene glycols, 2,2-(4,41-dihydroxydicyclohexyl) - propane, 4,41 - dihydroxydicyclohexyl-methane and 2,6-dihydroxydecahydronaphthalene. Examples describe the preparation of the bis-glycidyl ethers of carbonate esters of 2,2-(4,41-dihydroxydiphenyl)-propane, 2,2 - (4,41 - dihydroxydiphenyl) - butane and 4,41'- dihydroxy - 3,31 - dimethyl - diphenyl - sulphide and the subsequent hardening of the resulting esters (see Group IV(a)).