SYNTHESIS OF NOVEL MACROMONOMERS AND TELECHELICS OF POLY(2-ALKYL-2-OXAZOLINE)S

Novel macromonomers and telechelics of poly(2-alkyl-2-oxazoline) (PROZO) were synthesized by utilizing termination of propagating species (2-oxazolinium ions) in the living polymerization of 2-alkyl-2-oxazoline (ROZO) with suitable nucleophiles. Two types of p-vinylbenzyl-type macromonomers were obtained by terminating living PROZO with sodium p-vinylbenzyl alkoxide or with sodium p-vinylbenzyl mercaptide. The synthesis of telechelics having a functional group (SH, COOH) on both ends of PROZO was achieved by using a bis(2-oxazolinium salt) initiator. The PROZO dithiol was synthesized by two methods: (1) termination of the living species on both ends with NaSH, and (2) aminolysis of PROZO bis(O-ethyldithiocarbonate) given by treatment of the living PROZO with potassium O-ethyldithiocarbonate. Termination of the living PROZO with the sodium salt of di-t-butyl malonate yielded a PROZO with di-t-butyl malonate moieties on both polymer ends, from which the PROZO dicarboxylic acid was derived via free tetracarboxylic acid. (C) 1995 John Wiley & Sons, Inc.