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. 2022 Dec;43(24):e2200028.
doi: 10.1002/marc.202200028. Epub 2022 Feb 24.

Hydrolyzable Poly(β-thioether ester ketal) Thermosets via Acyclic Ketal Monomers

Benjamin M Alameda  1 , Joseph Scott Murphy  1 , Bernardo L Barea-López  1 , Karly D Knox  1 , Jonathan D Sisemore  1 , Derek L Patton  1
Affiliations

Hydrolyzable Poly(β-thioether ester ketal) Thermosets via Acyclic Ketal Monomers

Benjamin M Alameda et al. Macromol Rapid Commun. 2022 Dec.

Abstract

Hydrolytically degradable poly(β-thioether ester ketal) thermosets are synthesized via radical-mediated thiol-ene photopolymerization using three novel dialkene acyclic ketal monomers and a mercaptopropionate based tetrafunctional thiol. For all thermoset compositions investigated, degradation behavior is highly tunable based on the structure of the incorporated ketal and pH. Complete degradation of the thermosets is observed upon exposure to acidic and neutral pH, and under high humidity conditions. Polymer networks composed of cross-link junctions based on acyclic dimethyl ketals degrade the quickest, whereas networks containing acyclic cyclohexyl ketals undergo hydrolytic degradation on a longer timescale. Thermomechanical analysis reveals low glass transition temperatures and moduli typical of thioether-based thermosets.

Keywords: degradability; hydrolysis; ketal; thermosets; thiol-ene photopolymerization.

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