Synthesis of (bio)-degradable poly( β-thioester)s via amine catalyzed thiol-ene click polymerization

Joke Vandenbergh, Kayte Ranieri, Thomas Junkers

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37 Citations (Scopus)

Abstract

The well-known thiol-ene click reaction is used to polymerize dithiols and diacrylate monomers. Using catalytic amounts of hexylamine, poly(ester-sulfi de)s are synthesized via consecutive Michael additions between 1,4-butanedithiol and 1,6-hexanediol diacrylate. The molecular weight of the polymers is controlled by the stoichiometric balance of the reagents and by optimizing reaction time. Maximum conversion is achieved at close to 20 min at room temperature. Thermal characterization of the polymer shows a melting temperature of 53 °C and good thermal stability of up to 200 °C. The poly( β -thioester) readily degrades when in contact with acetic acid or NaOH solutions, but also degradation under more biological relevant conditions is indicated by partial hydrolysis of the ester linkages in phosphate buffers.

Original languageEnglish
Pages (from-to)2611-2617
Number of pages7
JournalMacromolecular Chemistry and Physics
Volume213
Issue number24
DOIs
Publication statusPublished - 21 Dec 2012
Externally publishedYes

Keywords

  • Biodegradable
  • Click reaction
  • Michael addition
  • Polyesters
  • Step-growth polymerization
  • Thiol-ene chemistry

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