Synthesis of functional polymers by atom transfer radical polymerization

Abstract

The preparation of monochelic polystyrene by atom transfer radical polymerization (ATRP) was investigated. The polymer analogous pathway by substitution of the bromide by an alcoholate resulted in significant elimination of the bromide and the degree of functionalization was low. Better results were achieved by the use of functional initiators. Carboxylic acid- and anhydride-bearing initiators were prepared by bromination of the commercially available 4-ethylbenzoic acid and the 4-methylphthalic anhydride, respectively. With these two products monochelic polystyrenes were synthesized. Further modification of the 4-(1-bromoethyl)benzoic acid led to initiators with a hydroxy or an oxazoline moiety. Again, the respective functional polystyrenes were obtained.