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

1990; Wiley; Volume: 181; Issue: 1 Linguagem: Inglês

10.1002/apmc.1990.051810114

1522-9505

B. Sandner, Hans‐Jörg Ziegler, Claus Bischof,

Chemical Synthesis and Reactions

Abstract The 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 R 4 NX 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 R 4 NX. MMA‐copolymers containing free carboxy groups react with an excess of ECH in the presence of R 4 NX 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.