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Keywords:

  • aliphatic polyesters;
  • amino-functional polymer;
  • biodegradable;
  • degradable polymers;
  • functionalization of polymers;
  • hydrophilic polymers;
  • lactone synthesis;
  • lactones;
  • polyelectrolytes;
  • polyesters;
  • ring-opening polymerization

Abstract

Novel 5-Z-amino-δ-valerolactone (5-NHZ-VL) was synthesized with an aim to prepare degradable polyesters and copolyesters having amino pendant groups. Following a straightforward and efficient synthetic pathway, 5-NHZ-VL was obtained in only two steps and up to 50% yield. The monomer was fully characterized by 1H NMR, 13C NMR, ESI mass spectrometry, and HPLC. Various conventional conditions were tested for this lactone ring-opening polymerization and led to the novel corresponding poly(5-NHZ-VL) (Mn = 7000 g/mol; PD = 1.2). Following this homopolymerization, 5-NHZ-VL was copolymerized with ε-caprolactone to generate a family of copolyesters with an amino-group content ranging from 10 to 80%. Finally, the polyelectrolyte poly(5-NH3+-VL) was recovered by removal of the protecting group under acidic conditions, and integrity of the polyester backbone was confirmed by 1H NMR. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010