UV-induced click-reactions such as the thiol-ene reaction are a straight-forward strategy for the synthesis of crosslinked polymers. In this study, copoly(2-oxazoline)s composed of (monofunctional) 2-ethyl-2-oxazoline and 2-nonyl-2-oxazoline as well as a (bisfunctional) 2-oxazolines containing either ether or ester bonds were synthesized by cationic ring-opening polymerizations; the bisfunctional 2-oxazolines were prepared from the thiol-ene reaction of glycol dimercaptoacetate or 2,2’-(ethylenedioxy)diethanethiol and 2-but-3’-enyl-2-oxazoline or 2-dec-9’-enyl-2-oxazoline. Crosslinked networks were synthesized either in-situ or by performing the polymeranalogous thiol-ene click reaction of copoly(2-oxazoline)s and glycol dimercaptoacetate. By variation of the repetition units and the degree of crosslinking, 80 gels were synthesized, of which 13 derivatives exhibited glass-transition temperatures in the narrow range from 20 to 30 °C, which renders them stiff below and flexible at body temperature. Only the gels that did not contain any 2-nonyl-2-oxazoline acted as hydrogels; all other gels were lipo- or amphigels. Maximum swelling degrees of 6 in water were observed. Polymer discs loaded with the tracer dye Eosin B were subjected to degradation, in the course of which highest release rates were found for the porcine liver esterase-mediated degradation at pH = 8.

Enzyme-degradable hydrogels based on copoly(2-oxazoline) networks

256th National Meeting (2018)

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