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Effect of ionic liquids on the structural,thermal, and in vitro degradation properties of poly(ε‐caprolactone) synthesized in the presence of Candida antarctica lipase B
Authors:Urszula Piotrowska  Marcin Sobczak  Ewa Oledzka  Christèle Combes
Affiliation:1. Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy with the Laboratory Medicine Division, Medical University of Warsaw, Warsaw, Poland;2. Chair of Chemistry, Department of Organic Chemistry, Faculty of Materials Science and Design, Kazimierz Pulaski University of Technology and Humanities in Radom, Radom, Poland;3. CIRIMAT, Université de Toulouse, CNRS, INPT, UPS, ENSIACET, 4 allée Emile Monso, CS 44362, France
Abstract:The study provides detailed information on the differences in the structural, thermal and degradation properties of poly(ε‐caprolactone) synthesized in two different ionic liquids, 1‐butyl‐3‐methylimidazolium hexafluorophosphate bmim]PF6] and 1‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl)imide bmim]NTf2], regarding its further usage in the pharmaceutical field. The polymer structure confirms the presence of both linear polymer chains with end‐functional hydroxyl groups allowing covalent coupling of the therapeutic agents, and cyclic macromolecules, both affecting the degree of crystallinity of polymer. The highest macrocyclic content (64%) after 7 days of polymerization at 80 °C was observed for bmim]NTf2]. For bmim]PF6], the macrocyclic content value was not dependent on the reaction time and remained at a similar level (10–14% at 80 °C). The results of degradation test revealed that hydrolytic degradation of ester bonds is more pronounced for PCLs synthesized in bmim]NTf2], due to their lower degree of crystallinity compared with PCLs obtained in bmim]PF6]. A high purity, low polydispersity index of the obtained polymers and high yield of the process (ca., 90%) indicate that ionic liquids seem to be promising solvents for the synthesis of biomedical polymers. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133, 43728.
Keywords:degradation  drug delivery systems  ionic liquids  polyesters  properties and characterization
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