Copolymerization of 2,6-dimethyl-4-bromophenol with 2-methyl-4-bromo-6-allylphenol and other p-bromophenols

Abstract

A series of poly(phenylene oxide) copolymers was prepared from 2,6-dimethyl-4-bromophenol and 2-methyl-4-bromo-6-allylphenol by the Price method of interfacial oxidative coupling. The physical and chemical properties of the copolymers were correlated with the molar proportions of the bromophenols. The thermosetting rates were proportional to the concentration of the allyl function and were of interest in the development of high-temperature thermosetting resins and adhesives. The preparation and copolymerization of 2-methyl-6-(α-methallyl)-4-bromophenol were also investigated. Homopolymerization of 2-methyl-4-bromophenol or 2,2′-methylenebis-(4-bromo-6-methylphenol) under the same conditions did not occur to any significant degree. When these bromophenols were used in attempted copolymerizations with 2,6-dimethyl-4-bromophenol, only low molecular weight homopolymers of the latter were obtained. The effect of these nonpolymerizing bromophenols as chain stoppers is discussed in connection with the mechanism for this type of polymerization.