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

Abstract

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)-ɛ-caprolactone (CCL) by the Baeyer-Villiger oxidation reaction using 3-chloroperoxybenzoic acid ( mCPBA) as the oxidant. Finally, the novel functionalized poly(ɛ-caprolactone) bearing the pendant N-isopropylamide functional groups, poly(6-( N-isopropyl-2-carbamoylethyl)-ɛ-caprolactone- co-ɛ-caprolactone)s (poly(CCL- co-CL)), were carried out successfully by bulk ring-opening polymerization of CCL and ɛ-CL initiated by Sn(Oct) 2. Poly(CCL- co-CL) were characterized by 1H NMR, 13C 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 °C was adopted to proceed the degrading study all through. Compared with poly(ɛ-caprolactone), the hydrolytic degradation of poly(CCL- co-CL) was much faster, which is confirmed by the weight loss and change of intrinsic viscosity.