Polydioxanone Derivative Bearing Methoxy Groups toward Bio‐Functional Degradable Polymers Exhibiting Hydration‐Driven Biocompatibility

Abstract

An aliphatic poly(ester-ether) with methoxy side chains from a glycerol derivative that exhibits increased hydration properties for potential applications in blood-contacting medical devices is developed. The poly(ester-ether) is prepared by ring-opening polymerization (ROP) of an analogue of 1,4-dioxan-2-one (DX) with a methoxy-containing substituent in the presence of acidic organocatalysts. It is found that the ring-chain equilibrium resides in the ROP of the DX analogue at room temperature and at relatively low monomer concentration (≈2 m). The organocatalytic ROP has enabled more than 80% monomer conversion at temperatures below 0 °C in the bulk state. The methoxy-bearing poly(ester-ether) is insoluble in water, amorphous, and viscous, demonstrating a high level of interaction with water when evaluating the thermal properties of the hydrated polymer and water contact angles. The polymer also shows susceptibility to hydrolysis and end-group dependence on thermal degradation. These results suggest a good potential for methoxy-bearing poly(ester-ether) as a biodegradable and biocompatible polymer derived from renewable feedstocks.

Organocatalyzed ring-opening reactions of γ-carbonyl-substituted ε-caprolactones

“…19,20 These results further lead to the recent developments of ether-functionalized PTMC and polydioxanone. [21][22][23] However, biodegradation of the PTMC analogues proceeds slowly compared to that of aliphatic polyesters. 20,24 We hypothesize that PCL analogues with similar sidechain structures can be of interest because they can indicate different degradation proles while retaining the blood compatibility.…”