Development of Ester Free Type Poly(trimethylene carbonate) Derivatives with Pendant Fluoroaromatic Groups

Abstract

The facile method for the synthesis of ester free type poly(trimethylene carbonate) (PTMC) derivatives is previously reported. In this paper, a series of PTMC derivatives with fluoroaromatic groups in the side chain are synthesized to improve polymer properties. Thermal analysis reveals that all the PTMC derivatives have a decomposition temperature exceeding 300 °C. Furthermore, as the number of fluorine attached to the aromatic ring increases, the glass transition temperature decreases. In order to clarify the surface properties of their films, the contact angles and protein adsorption are evaluated. The hydrophobic nature is attributed to the fluorine groups at the side chain. Furthermore, it is suggested that as the number of fluorine attached to the aromatic ring increases, the protein adsorption is suspended. There is a possibility that a new biomaterial could be created by introducing a fluoroaromatic group into the side chain of PTMC with ester free structure.

Surface coating and characteristics of ester-free poly(trimethylene carbonate) bearing an aromatic urea moiety for biomaterials use

“…36 The results were similar to those of Nobuoka et al where the introduction of aromatic derivatives into the side chain of PTMC yielded a T g of up to 1 1C. 37 The presence of an SU group in the side chain of PTMC further improved T g , suggesting the presence of self-association hydrogen bonding of the polymer chains. This is supported by the findings of Shieh et al who showed that incorporating acrylic acid units into poly(N-isopropylacrylamide) (PNIPAAm) tended to increase the T g due to strong hydrogen bonding between the amide groups present in the PNIPAAm.…”

“…36 The results were similar to those of Nobuoka et al where the introduction of aromatic derivatives into the side chain of PTMC yielded a T g of up to 1 °C. 37 The presence of an SU group in the side chain of PTMC further improved T g , suggesting the presence of self-association hydrogen bonding of the polymer chains.…”

Synthesis of amphiphilic block copolymer using trimethylene carbonate bearing oligo(ethylene glycol) and investigation of thin film including cilostazol

“…[ 26 ] We also improved a synthetic pathway for ester free type TMC derivatives, [ 27 ] which brought wider variation of PTMC derivatives. [ 28 ] Although various materials have been successful with ester‐free PTMC, application as a stent coating material has yet to be achieved. We believe PTMC derivatives are useful for stent coating, because PTMC is more flexibile [ 29,30 ] compared with other biodegradable polyesters.…”