Radical Copolymerization of Ferulic Acid Derivatives with Ethylenic Monomers.

Bio-based ferulic acid (FA), (E )-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid was converted to 1,2-disubstituted ethylenic monomer (FA1) via methyl esterification followed by silylation with tertbutyldimethylsilyl chloride. Radical copolymerization of FA1 with styrene (St), methyl methacrylate (MMA), and 4-acetoxy-3-methoxystyrene (FA2) prepared from FA were carried out using azobisisobutyronitrile as an initiator at 80°C. It is found that FA1 was copolymerized with St and FA2, but not with MMA. The formation of copolymers was confirmed by ³H- and ¹³C-NMR analyses. The reactivity ratios of FA1 and St estimated by the Fineman-Ross method are r_FA1=0.12 and r_St=2.46. In the case of the copolymerization of FA1 with FA2, the reactivity ratios, r_FA1=0.13 and r_FA2=2.66 were determined. [ABSTRACT FROM AUTHOR]