Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(epsilon-caprolactone)s

Abstract

This study reports on the synthesis of new fluoro functionalized poly(epsilon-caprolactone)s (F-PCLs) via ring-opening polymerization (ROP) of epsilon-caprolactone (epsilon-CL) for different time intervals (24 and 48 h.) by using 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (OFP) as an initiator. The structure and properties of F-PCLs are investigated by Fourier-transform infrared (FT-IR), proton and fluorine 19 nuclear magnetic resonance (H-1-NMR and F-19-NMR) spectroscopies, gel permeation chromatography (GPC), energy dispersive scanning electron microscopy (SEM-EDS), atomic force microscopy (AFM), water contact angle (WCA) measurements, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). Enzymatic degradation experiments arc also conducted to study the biodegradation behavior of terminal F-PCLs. Experimental observations obtained by H-1-NMR, F-19-NMR and GPC indicate that higher reaction time leads to the formation of higher fluorinated repeating units in F-PCLs. This observation is confirmed by results of SEM-EDS, AFM, WCA, DSC and TGA analyses, respectively. Based on the biodegradability study of F-PCLs in degradation solutions in the presence and absence of porcine pancreatic lipase, it can observed that utilization of more extended time in the ROP reaction medium decreases the biodegradation of resulting polymer. With the obtained features, biodegradable F-PCLs might have potential applications, particularly in the fields of drug delivery and tissue engineering, requiring improved thermal but lower wettability properties.