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: National Science Centre (Poland), PRELUDIUM 6 research scheme
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2016
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/app.43728; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fapp.43728; https://onlinelibrary.wiley.com/doi/pdf/10.1002/app.43728

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][PF 6 ] and 1‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl)imide [bmim][NTf 2 ], 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][NTf 2 ]. For [bmim][PF 6 ], 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][NTf 2 ], due to their lower degree of crystallinity compared with PCLs obtained in [bmim][PF 6 ]. 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.