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Radical polymerizations of two stereoisomeric trimethacrylates with rigid adamantane‐like cores from naturally occurring myo‐inositol Part A Polymer chemistry

Okamoto, Shusuke, Tanaka, Kentaro, Sudo, Atsushi
Journal of polymer science 2018 v.56 no.15 pp. 1743-1748
crosslinking, moieties, myo-inositol, polymerization, polymers, thermal stability
Two stereoisomeric trimethacrylates, T1 and T2, which share a common adamantane‐like rigid core, were synthesized from naturally occurring myo‐inositol, and their radical polymerization behaviors were investigated. For the synthesis of T1, myo‐inositol was converted to triol 1, bearing one equatorial hydroxyl group and two axial hydroxyl groups, by orthoesterification, which was used as a precursor. For the synthesis of T2, 1 was converted to triol 2, bearing three axial hydroxyl groups, which was used as a precursor. Investigations on the radical polymerization of T1 and T2, which potentially accompanies the cyclopolymerization of the axially oriented methacrylate moieties, revealed significant differences between the two. (1) The polymerization of T1 affords networked and thus insoluble polymers PT1, while that of T2 affords less crosslinked and thus soluble polymers PT2. (2) The amount of residual methacrylate moieties was larger in PT2 than in PT1. (3) PT2 had higher thermal stability than PT1, though PT2 contained a larger amount of unreacted methacrylate moieties. These tendencies were successfully correlated with the difference in cyclopolymerization efficiency between the polymerizations of the two monomers. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1743–1748