Tuning the poly(glycerol itaconate)'s Michael adducts: Post-reaction pathways to functionalization

Abstract

CC double bonds in the poly (glycerol itaconate) backbone facilitate its functionalization through post-polymerization reactions. Among these, aza- and thio-Michael addition reactions hold the potential for improving material properties, yet their application to poly (glycerol itaconate) remains underexplored. To address this gap, we synthesized poly (glycerol itaconate) (esterification degree = 71.0 %) using non-toxic and biodegradable itaconic acid and glycerol, followed by its modification via Michael addition with l-cysteine (modification degree = 24.8–96.9 %), a non-toxic alternative to diamines previously used in similar reactions. The successful functionalization of poly (glycerol itaconate) was confirmed through FTIR, NMR, and thermal analyses, verifying the presence of Michael adducts. The hydrophilicity of the crosslinked materials was demonstrated by wet contact angle measurements (<90°), while cytotoxicity tests on 24-h extracts indicated no cytotoxic effects in the two tested samples (>70 %). These findings underscore the potential of poly (glycerol itaconate) derivatives as promising materials for further applications, such as tissue engineering and related fields.