GB842264A - Process for the production of polymerisable polyesters and mixtures of these polyesters with polymerisable monomeric vinyl compounds - Google Patents

Abstract

A polymerizable polyester is made by (a) polyesterifing a C-mono-or di-b - alkenyl substituted aromatic dihydroxy compound or a di-oxalkylated derivative thereof with a dicarboxylic acid (or an ester-forming derivative thereof) or with an ester-forming derivative of carbonic acid or (b) polyesterifying a C- mono-or di-b -alkenyl substituted aryl-di (oxocarboxylic acid) (or an ester-forming derivative thereof) with a dihydroxy compound. Suitable dihydroxy compounds for use in process (a) are mono- or di-allylhydroquinone, 3-mono- or 3,31-diallyl4,41-dihydroxydiphenyl and the 3-mono- or 3,31-diallyl compounds of (4,41-dihydroxydiphenyl)-methane, 2,2-(4,4-dihydroxydiphenyl)-ethane or 1,1-(4,41-dihydroxydiphenyl)-propane, -butane, -pentane, or -cyclohexane, or the corresponding mono- or dimethallyl ormono-or di-crotyl compounds, or the di-oxyethylated derivaties of these substituted dihydroxy compounds: suitable dicarboxylic acids are adipic, glutamic, pimelic, fumaric, maleic, phthalic or cyclo aliphatic dicarboxylic acids which may be used in the form of their esters with mono-hydroxy compounds and suitable ester-forming derivatives of carbonic acid are dialkyl or diaryl carbonates, phosgene, or bis-chlorocarbonic esters of aliphatic, cycloaliphatic or aromatic dihydroxy compounds. In process (a), other aromatic, cycloaliphatic or aliphatic dihydroxy compounds may be used as co-reactants. Suitable dicarboxylic compounds for process (b) are the reaction products of the above-mentioned c-mono- or di-b -alkenyl substituted dihydroxy compounds and chloroacetic acid and its esters and suitable dihydroxy compounds are aliphatic, cycloaliphatic or aromatic dihydroxy compounds. The polyesters dry in thin layers when exposed to air and drying may be accelerated by addition of the usual driers. Many are soluble in aromatic hydrocarbons, esters and chlorinated solvents. They dissolve in vinyl compounds, e.g. styrene, vinyl chloride, vinyl acetate, methyl methacrylate or glycol dimethacrylate to form, after addition of a peroxide or redox catalyst, masses suitable for the production of air-drying or stove-drying lacquers or of moulding or castings which may be reinforced with glass fibre. In Examples (1) A polycarbonate from 2,2-(3,31-diallyl-4,41-diphenoxoethanol) - propane and diphenyl carbonate is dissolved in styrene and the mixture copolymerized by heating after addition of benzoyl peroxide, and if desired glass fibres; (2) A polycarbonate from 2,2-(3,31-diallyl-4,41-diphenoxoethanol)-propane, hexanediol and diphenyl carbonate is dissolved in methylene chloride and benzoyl peroxide and cobalt naphthenate added to form a lacquer; (3) A polycarbonate from 2,2-(3,31-diallyl-4,41-diphenoxoethanol) -propane, diethylene glycol and diphenyl carbonate is dissolved in toluene to form a lacquer; (4) A polycarbonate from 2,2-(3,31diallyl-4,41-diphenoxoethanol)-propane and 2,2-(4,41-dihydroxydiphenyl)-propane-bis-phenyl carbonate is copolymerized with a mixture of styrene and methyl methacrylate after the addition of benzoyl peroxide; (5) A polyester from 2,2-(3,31-diallyl-4,41-diphenoxoacetic acid)-propane, adipic acid and diethylene glycol is copolymerized with methyl methacrylate after the addition of benzoyl peroxide; (6) A polyester from 2,2-(3,31-diallyl-4,41-diphenoxoethanol)-propane and 2,2-(3,31-diallyl-4,41-diphenoxoacetic acid)-propane is dissolved in toluene and benzoyl peroxide and Co, Pb or Mn naphthenate added to form a lacquer, (7) A polyester from 2,2-(3,31-diallyl-4,41-diphenoxoethanol) -propane and adipic acid is dissolved in toluene to form a lacquer; (8) A polyester from 2,2-(3,31-diallyl-4,41-diphenoxoethanol)-propane and phthalic anhydride is copolymerized with glycolbis-methacrylate after the addition of benzoyl peroxide; (9) A polycarbonate is made from c-diallyl-hydroquinone, 1,1-(4,41-dihydroxydiphenyl)-cyclohexane and diphenyl carbonate and may be copolymerized with vinyl monomers after the addition of perhydroxy catalysts; (10) A polycarbonate from 2,2-(4,41-dihydroxydiphenyl) -propane, 2,2- (3,31-diallyl-4,41-diphenoxoethanol) -propane and phosgene is copolymerized with styrene after the addition of benzoyl peroxide; (11) A polycarbonate obtained by reacting a mixture of 2,2-(3,31-diallyl-4,41-diphenoxoethanol) -propane and 2,2-(4,41-dihydroxydiphenyl)-propane with phosgene in the presence of styrene is hardened by heating after the addition of benzoyl peroxide; (12) A polycarbonate from 2,2-(3,31-dimethallyl-4,41-diphenoxoethanol) -propane and diphenyl carbonate is copolymerized with styrene after the addition of benzoyl peroxide; (13) A polycarbonate from 3,31-dimethallyl-4,41-dihydroxydiphenyl, 1,6-hexanediol, 1,1-(4,41-dihydroxydiphenyl)-cyclohexane and diphenyl carbonate is copolymerized with styrene after the addition of benzoyl peroxide; (14) A polycarbonate from 3,31- dimethallyl-4,41-dihydroxydiphenyl, 1,1-(4,4-dihydroxydiphenyl)-cyclohexane and diphenyl carbonate is copolymerized with styrene after the addition of benzoyl peroxide; (15) A polycarbonate from 3,31-diallyl-4,41-dihydroxydiphenyl, 1,1-(4,41-dihydroxydiphenyl)-cyclohexane and diphenyl carbonate is copolymerized with styrene or a mixture of styrene and methyl methacrylate; (16) A polycarbonate from 2,2-(3,31-dimethallyl4,41-diphenoxoethanol) -propane, 2,2-(4,41-dihydroxydiphenyl), diethylene glycol and diphenyl carbonate is copolymerized with glycol dimethacrylate after the addition of benzoyl peroxide; (17) A polycarbonate from 1,1-(3,31-diallyl-4,41diphenoxoethanol) -cyclohexane, 2,2-(4,41-dihydroxydiphenyl)-propane and diphenyl carbonate is copolymerized with styrene after the addition of benzoyl peroxide; (18) A polyester from 2,2-(3,31-diallyl-4,41-diphenoxoethanol) -propane, phthalic anhydride, maleic anhydride and 1,3-butanediol is dissolved in styrene and cyclohexanone peroxide and cobalt naphthenate added for form a lacquer. (19) A polyester suitable as a stoving lacquer is made from 2,2-(3,31-diallyl4,41-diphenoxopropanol) -propane, phthalic anhydride and adipic acid.