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

• Published in: Journal of Applied Polymer Science
• Main Authors: Piotrowska, Urszula, Sobczak, Marcin, Oledzka, Ewa, Combes, Christèle
• Other Authors: Medical University of Warsaw - Poland, Kazimierz Pulaski University of Technology and Humanities in Radom, Centre interuniversitaire de recherche et d'ingenierie des matériaux (CIRIMAT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2016
• Subjects: Drug delivery systems; Ionic liquids; Polyesters; Properties and characterization; Degradation; [CHIM.POLY]Chemical Sciences/Polymers; Antarc*; Antarctica
• Online Access: https://hal.science/hal-01644363; https://hal.science/hal-01644363/document; https://hal.science/hal-01644363/file/Piotrowska_18209.pdf; https://doi.org/10.1002/app.43728

International audience 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 8C 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 8C). 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.