Toward Renewable and Functional Biomedical Polymers with Tunable Degradation Rates Based on Itaconic Acid and 1,8-Octanediol

Biomedical polymers face rigid requirements for the biocompatibility of their monomers, the final polymeric product, and their residual reagents from their synthesis schemes. However, their preparation still heavily relies on nonrenewable resources. Itaconate (ITA) is an organic acid that is used as a platform chemical for the production of numerous value-added chemicals and serves as a valuable green chemistry alternative to petrochemical derivatives. In recent years, the multiple roles of this molecule in cell metabolism have generated great attention, particularly as a modulator of inflammation and infection. Recently, we developed a family of ITA polyesters that leverage hydrolytically driven degradation to recapitulate its biofunctionality. This renewable-based material platform warrants characterization of material properties based on synthesis conditions in order to advance their potential application. In this work, we describe the development of ITA polyesters relying on defined reaction feed ratios and reaction times. Material characterization highlighted the significant impact of changing molar feed on molecular weight, which corresponded to increased viscosity and decreased percent degradation. Using 20% excess ITA monomers in the reaction led to optimal outcomes, suggesting opportunities in future material design. Leveraging this characterization, ITA polyesters can be altered through synthesis conditions to achieve appropriate and specific biopolymer applications.

Automated summary

Biomedical polymers require strict biocompatibility and can utilize itaconate as a renewable resource, offering a green chemistry alternative. By optimizing reaction conditions, ITA polyesters can be tailored for specific applications.