Easy synthesis and ring‐opening polymerization of 5‐ Z ‐amino‐δ‐valerolactone: New degradable amino‐functionalized (Co)polyesters

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 1 H NMR, 13 C 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) ( M n = 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‐NH 3 + ‐VL) was recovered by removal of the protecting group under acidic conditions, and integrity of the polyester backbone was confirmed by 1 H NMR. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010