Easy Synthesis and Ring-Opening Polymerization of 5-Z-Amino-δ-valerolactone New Degradable Amino-Functionalized (Co)polyesters

Novel 5 Z amino delta 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 H-1 NMR C-13 NMR ESI mass spec trometry 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 c 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 H-1 NMR (C) 2010 Wiley Periodicals Inc J Polym Sci Part A Polym Chem 48 5891-5898 2010