2-Oxazoline-terminated polystyrene by atom-transfer radical polymerization

Abstract

Macromonomers of polystyrene containing one functional 1,3-oxazoline end group were obtained by atom-transfer radical polymerization (ATRP) using oxazoline-containing initiators. 2-(1-Bromoethyl)-1,3-oxazoline (2b) and 2-(4-(1-bromoethyl)phenyl)-1.3-oxazoline (6) were prepared for this purpose. 2-(1-Bromoethyl)-1,3-oxazoline was prepared by the bromination of 2-ethyl-1,3-oxazoline with N-bromosuccinimide (NBS). 2-(4-(1-Bromoethyl)phenyl)-1,3-oxazoline was obtained by the treatment of 4-(1-bromoethyl)benzoic acid with ethanolamine and subsequent cyclization with SOCl2. Both initiators proved to be suitable for the ATRP of styrene. Oxazoline mono-terminated polystyrenes with Mn between 2000 and 3500 g · mol-1 were obtained. The oxazoline groups were observed in the NMR spectra.