Epoxy functionalized polymethacrylates based on various multifunctional d-glucopyranoside acetals


Correspondence to: D. Neugebauer (E-mail: dorota.neugebauer@polsl.pl)


The synthesis of acetal-derived d-glucopyranosides with a various number of hydroxyl groups (the first step, acetalization) and their modified forms with bromoester groups (the second step, esterification) are presented here. The latter, due to the type of functional groups, can be used to initiate the controlled atom transfer radical polymerization. The copolymerizations of equimolar feed of methacrylate monomers, namely, methyl methacrylate and glycidyl methacrylate, were initiated by prepared new glycoinitiators, based on methyl α-d-glucopyranoside (MeαdGlu) or 2-(hydroxymethyl)phenyl-β-d-glucopyranoside (salicin), in the presence of the catalyst system CuCl/dNbpy in anisole at 30 °C. The conditions were sufficient for successful synthesis of well-defined copolymers with sugar cores sheltered by two-, three-, four-, or six-polymethacrylate segments with various polymerization degrees (DParm = 15 – 70) and low dispersity indices (Ð = 1.15–1.30). Because of the presence of oxirane groups, the star-copolymers can be functionalized in further steps by biologically active compounds or modified to amphipilics. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2483–2494