Degradable and curable poly(conjugated ester)s prepared by acryl- and conjugate-substitutions of the 'smallest' monomer

alpha-(Chloromethyl)acryloyl chloride was polymerized with various bisphenols and diamines to yield poly(conjugated ester)s. The polymer prepared from bisphenol Z underwent curing by heating at 170 degrees C, while copolymerization with methyl methacrylate afforded a crosslinked polymer. The poly(conjugated ester)s were chemically decomposed via main-chain scission by the conjugate substitution with benzyl mercaptan. Moreover, the treatment with 5 wt% aqueous ammonia resulted in complete main-chain scission to the monomeric units by conjugate substitution and acyl substitution reaction, recovering bisphenol Z. Although curing and main-chain scission resulted in contractive changes on polymer properties, both reactions were achieved by a same skeleton, alpha-(aryloxymethyl)acrylate. Thus, alpha-(chloromethyl)acryloyl chloride is the smallest monomer to incorporate such a curable and degradable skeleton.