Synthesis and Reversible Hydration-Dehydration System of Copolymers Bearing a Vicinal Tricarbonyl Structure

Novel copolymers composed of a styrene (St) derivative bearing a vicinal tricarbonyl moiety and various vinyl monomers such as St, methyl methacrylate (MMA), and N-vinylpyrrolidone (NVP) were synthesized by (1) radical copolymerization of a St derivative with a 1,3-diketone structure with St, MMA, and NVP and (2) successive oxidation of the resulting copolymers with N-bromosuccinimide in DMSO to convert their 1,3-diketone moieties in the side chains into the corresponding vicinal tricarbonyl moieties. Their tricarbonyl moieties were readily hydrated in water-containing acetone to generate the corresponding copolymers bearing geminal diol structures in the side chains. On the other hand, heating the resulting copolymers bearing the geminal diol structures in vacuo-enabled successful recovery of the vicinal tricarbonyl moieties to demonstrate the reversible nature of this system. The hydration behavior in powdery state under air atmosphere saturated by water was also investigated. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 50: 2619-2625, 2012