Synthesis and characterization of fluorocarbon chain end‐capped poly(carbonate urethane)s as biomaterials: A novel bilayered surface structure

Abstract

Poly(carbonate urethane)s (PCUs) are usually considered as biostable elastomers for long-term implantation. However, their hydrolytic stability is still questionable. The biodegradation appears to be initiated by oxidative and hydrolytic substances released by inflammatory cells. Therefore, the biostability of polyurethane might be improved with control of surface structure to reduce inflammatory response. A new type of PCUs end-capped with perfluoro chains was synthesized to explore a new avenue. A fluorinated alcohol, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol (PDFOL), was end-capped to the backbones of PCUs by reaction of the --OH in PDFOL with the --NCO end groups in PCU backbones. Contact angle measurement, X-ray photoelectron spectroscopy, atomic force microscopy, and attenuated total reflectance-Fourier transform infrared spectroscopy were used to examine their surface structure and properties. Elemental analysis, gel permeation chromatography, differential scanning calorimetry, and tensile testing were used to assess bulk chemistry and properties. The fluorocarbon end-capped poly (carbonate urethane)s (FPCUs) maintained the high mechanical properties (about 40 MPa tensile strength) and typical microphase separation structure of polyurethane elastomers. Results from surface analyses revealed the presence of a double-layered structure at the surfaces of the FPCUs. The first one was composed of fluorocarbon tails rising up on the uppermost layer and the second one made up of hard-segments. This novel bilayered surface structure could protect the weak carbonate linkages in soft segments, and consequently, may potentially increase the biostability of this kind of polyurethanes.