Synthesis, characterization and degradability of the novel aliphatic polyester bearing pendant N-isopropylamide functional groups

The synthesis, characterization, and degradability of the novel aliphatic polyester bearing pendant N-isopropylamide functional group are reported for the first time. 2-(N-Isopropyl-2-carbamoylethyl)cyclohexanone (CCH) was first synthesized by the Michael reaction of N-isopropylacrylamide with cyclohexanone and was subsequently converted into 6-(N-isopropyl-2-carbamoylethyl)-epsilon-caprolactone (CCL) by the Baeyer-Villiger oxidation reaction using 3-chloroperoxybenzoic acid (mCPBA) as the oxidant. Finally, the novel functionalized poly(epsilon-caprolactone) bearing the pendant N-isopropylamide functional groups, poly(6-(N-isopropyl-2-carbamoylethyl)-epsilon-caprolactone-co-epsilon-caprolactone)s (poly(CCL-co-CL)), were carried out successfully by bulk ring-opening polymerization of CCL and epsilon-CL initiated by Sn(OCt)(2). Poly(CCL-co-CL) were characterized by H-1 NMR, C-13 NMR, SEC and DSC. The copolymer containing 9.1 mol% CCL formed flexible films and was used to study its degradability. A phosphate buffer (pH = 7.4) with temperature 37 degrees C was adopted to proceed the degrading study all through. Compared with poly(epsilon-caprolactone), the hydrolytic degradation of poly(CCL-co-CL) was much faster, which is confirmed by the weight loss and change of intrinsic viscosity. (C) 2008 Elsevier Ltd. All rights reserved.