Aza-Michael addition reaction: Post-polymerization modification and preparation of PEI/PEG-based polyester hydrogels from enzymatically synthesized reactive polymers

Christian Hoffmann, Mihaiela C. Stuparu, Anders Daugaard, Anzar Khan

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The utility of aza-Michael addition chemistry for post-polymerization functionalization of enzymatically prepared polyesters is established. For this, itaconate ester and oligoethylene glycol are selected as monomers. A Candida Antarctica lipase B catalyzed polycondensation reaction between the two monomers provides the polyesters, which carry an activated carbon-carbon double bond in the polymer backbone. These electron deficient alkenes represent suitable aza-Michael acceptors and can be engaged in a nucleophilic addition reaction with small molecular mono-amines (aza-Michael donors) to yield functionalized linear polyesters. Employing a polyamine as the aza-Michael donor, on the other hand, results in the formation of hydrophilic polymer networks.

Original languageEnglish
Pages (from-to)745-749
Number of pages5
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume53
Issue number6
DOIs
Publication statusPublished - 2015 Mar 15
Externally publishedYes

Keywords

  • Aza-Michael addition
  • Enzymatic polymerization
  • Functionalization of polymers
  • Hydrogels
  • Polyesters

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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