Hydrolysis of hydrophobic poly(2-oxazoline)s and their subsequent modification via aza-Michael addition

Abstract

Partially hydrolysed poly(2-oxazoline)s possess unique properties. However, much of the focus in this area has been on water soluble poly(2-oxazoline)s. Where hydrophobic poly(2-oxazoline)s have been used, this is often for selective hydrolysis. However, hydrolysis of very hydrophobic polymers could lead to interesting solution behaviour. Herein, we describe universal conditions for the hydrolysis of poly(2-alkyl-2-oxazoline)s suitable for both hydrophobic and hydrophilic 2-oxazolines. We show that the system utilised gives comparable rates to that of water alone for poly(2-ethyl-2-oxazoline). In addition, poly(2-fatty acid-2-oxazoline) was hydrolysed using the developed system and was found to proceed in a controlled manner allowing the targeting of specific degrees of hydrolysis, albeit much slower than for poly(2-ethyl-2-oxazoline). Finally, we demonstrate the partial functionalisation of poly(2-oxazoline)-poly(ethylene imine) co-polymers via aza-Michael addition.