Abstract
In order to fabricate polymers bearing both reactive hydroxyl and other functional groups, we conducted radical polymerization of methacrylates bearing hydroxyurethane structures prepared from aminolysis of a methacrylatebearing a five-membered cyclic carbonate, and examined reactions of the resulting polymers. For the efficient synthesis aforementioned monomers, we optimized the reaction conditions, i. e., use of a trace excess amount of amines to the methacrylate bearing a five-membered cyclic carbonate at 0 ℃ in toluene, by which the undesired Michael addition to the double bonds was suppressed. The functional groups originating from the amines allow the polymers obtained from radical polymerizations of the methacrylate bearing hydroxyurethane structures to be soluble in various common organic solvents in spite of the high densities of the hydroxyl groups. The reactions of the resulting polymers with cyclic anhydrides in the presence of triethylamine and with 2-methacryloyloxyethyl isocyanate afforded polymers bearing carboxylate and methacryl groups, respectively. The polymer bearing methacrylate moieties in the side chains could be thermally networked. The reaction of the polymer with 4,4'-methylene bis(phenyl isocyanate) afforded a networked polymer.
