Chinese Journal of Chemistry 2011, 29(2), 343-350.
作者：Yue Zeng, Yan Zhang, Meidong Lang.*
關鍵字：ε-caprolactone, δ-valerolactone, poly(ε-caprolactone-co-δ-valerolactone), pendant groups
論文來源：期刊
發表時間：2011年
In this paper, aliphatic polyesters functionalized with pendant carboxylic groups were synthesized via several steps. Firstly, substituted cyclic ketone, 2-(benzyloxycarbonyl methyl)cyclopentanone (BCP) was prepared through the reaction of enamine with benzyl-2-bromoacetate, and subsequently converted into the relevant functionalized δ-valerolactone derivative, 5-(benzyloxy carbonylmethyl)-δ-valerolactone (BVL) by the Baeyer-Villiger oxidation. Secondly, the ring-opening polymerization of BVL with ε-caprolactone was carried out in bulk using stannous octoate as the catalyst to produce poly(ε-caprolactone-co-δ-valerolactone) bearing the benzyl-protected carboxyl functional groups [P(CL-co-BVL)]. Finally, the benzyl-protecting groups of P(CL-co-BVL) were effectively removed by H2 using Pd/C as the catalyst to obtain poly(ε-caprolactone-co-δ-valerolactone) bearing pendant carboxylic acids [P(CL-co-CVL)]. The structure and the properties of the polymer have been studied by Nuclear Magnetic Resonance (NMR), Fourier Infrared Spectroscopy (FT-IR) and Differential Scan Calorimetry (DSC) etc. The NMR and FT-IR results confirmed the polymer structure, and the 13C NMR spectra have clearly interpreted the sequence of ε-caprolactone and 5-(benzyloxycarbonylmethyl)-δ-valerolactone in the copolymer. When the benzyl-protecting groups were removed, the aliphatic polyesters bearing carboxylic groups were obtained. Moreover, the hydrophilicity of the polymer was improved. Thus, poly(ε- aprolactone-co-δ-valerolactone) might have great potential in biomedical fields.