Synthesis of poly(ε-caprolactone-co-methacrylic acid) copolymer via phosphazene-catalyzed hybrid copolymerization

Abstract

Poly(ε-caprolactone-co-tert-butyl methacrylate) (CL-co-BMA) random copolymer is synthesized via hybrid copolymerization with 1-tert-butyl-4,4,4- tris(dimethylamino)-2,2-bis[tris(dimethylamino)phophoranylidenamino]-2Λ5, 4Λ5-catenadi(phosphazene) (t-BuP4) as the catalyst. The copolymer is hydrolyzed into poly(ε-caprolactone-co-methacrylic acid) (CL-co-MAA), a charged copolymer. Nuclear magnetic resonance, Fourier transform infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis measurements indicate that cyclic ester and vinyl monomer form a random copolymer. The degradation of the copolymers has also been studied by use of quartz crystal microbalance with dissipation. Poly(ε-caprolactone-co-tert- butyl methacrylate) (CL-co-BMA) random copolymer is synthesized via hybrid copolymerization with organic catalyst (t-BuP4). The hydrolysis of CL-co-BMA yields ε-caprolactone-co-methacrylic acid (CL-co-MAA), a charged degradable copolymer. CL-co-MAA enzymatically degrades much faster than poly(ε-caprolactone). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.