Considerable attention has been focused on developing materials that readily degrade in the natural environment. While many reports have focused on incorporating esters and anhydrides into polymer backbones, ketals have been underutilized in applications outside biomedical applications. Herein, we report a route to synthesize hydrolytically labile poly(thioether ketal) thermoplastics via thiol-ene photopolymerizations. We found that the incorporation of ketal moieties along the polymer backbone enabled rapid degradation under acidic aqueous environments. In each case, polymer hydrolytic stability was predicated on two variables – 1) hydrolytic stability derived from the stability of the ketal moiety and 2) polymer backbone hydrophobic/hydrophilic characteristics. The thermal properties of the resulting materials were found to be characteristic of general thiol-ene materials, i.e. T<sub>g</sub> well below room temperature.

Development of hydrolytically labile poly(thioether ketal) thermoplastics

ACS Spring Meeting 2021

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