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

Abstract

This study reports on the synthesis of new fluoro functionalized poly(ε-caprolactone)s (F-PCLs) via ring-opening polymerization (ROP) of ε-caprolactone (ε-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 (1 H-NMR and 19 F-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 are also conducted to study the biodegradation behavior of terminal F-PCLs. Experimental observations obtained by 1 H-NMR, 19 F-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.

Electrospinning of Poly(1,4‐Cyclohexanedimethylene Acetylene Dicarboxylate): Study on the Morphology, Wettability, Thermal and Biodegradation Behaviors

“…In addition, various functional groups on their hydrocarbon main chains can be easily modified for use in common chemical reactions and allow the material to be easily adapted to different processing methods. [ 5–9 ] Therefore, it is obvious that the production of innovative aliphatic polyesters with various functional groups and properties is of great importance for use in a wide variety of application areas.…”

Tuning the mechanical properties and degradation properties of polydioxanone isothermal annealing

“…These polymer materials seriously pollute the environment and endanger living organisms. As environmental awareness has increased in recent decades, the biodegradable materials offered in different areas have attracted increasing interest [2,3].…”

“…These polymer materials seriously pollute the environment and endanger living organisms. As environmental awareness has increased in recent decades, the biodegradable materials offered in different areas have attracted increasing interest [2,3].In order to avoid the possible risks of metal implants implanted in the human body, such as bone corrosion, stress shielding effect, defects of nondegradation, and the need for secondary surgery, absorbable polymer materials are being increasingly favored by researchers. At present, absorbable polymers are mostly used for implant materials that do not require high strength.…”

Bactericidal effect of cationic hydrogels prepared from hydrophilic polymers

“…Consequently, polymers are currently required to have various properties, and current studies are focused on the different properties of polymers, including biodegradability and environmental compatibility. [1,2] Hydrogels are hydrated polymeric materials usually comprising >90% water by weight. Hydrogels are used in products such as contact lenses and form the basis of cellular structure.…”