Introduction of hydroxyethyl and glycidyl ester groups into methyl methacrylate copolymers by polymer analogous reactions

Abstract

AbstractThe reactions of 2‐chloroethanol and epichlorohydrin (ECH), respectively, with alkali salts of partially hydrolyzed methyl methacrylate (MMA) polymers as well as with MMA copolymers containing free carboxy groups were studied. Quaternary ammonium halogenides R4NX are effective catalysts of these reactions. Up to 80% of alkali carboxylate groups were converted into hydroxyethyl ester groups to yield completely soluble copolymers. By reaction of ECH with alkali salts of the copolymers, crosslinked products were obtained. The gel fraction may be reduced from 87% to 5% if the reaction is carried out in the presence of R4NX. MMA‐copolymers containing free carboxy groups react with an excess of ECH in the presence of R4NX via the chlorohydrin ester and dehydrochlorination (transepoxidation) to produce completely soluble glycidyl ester copolymers of low chlorine content (≤0.4%). Yields of epoxy groups up to 95% have been attained.