Synthetic polymers have become some of the most important materials in modern society due to their valuable physical properties and ease of production, but these benefits are accompanied by detrimental environmental impacts. Polymeric waste is accumulating in landfills and oceans at a much faster rate than it is being recycled or broken down, in large part because the desired durability of these materials is often in conflict with rapid degradation upon end-of-life. To address this issue, we sought to develop polymeric materials that would be durable during everyday use yet easily degradable when exposed to specific, room temperature conditions. Initially focused on polyurethanes, we designed an acid-labile monomer that was copolymerized with a commercially available diisocyanate to generate polyurethane elastomers. These materials were stable even in aqueous acid, but fully degraded within minutes in anhydrous acidic conditions at room temperature. This degradation proceeds <i>via</i> a mechanism termed CyclizAtion-Triggered CHain (CATCH) cleavage, which utilizes a cyclization reaction to “catch” transient breaks along the polymer backbone. Structure-activity relationship studies show the potential to tune the kinetics of this degradation mechanism. Additional monomers containing the CATCH functionality were synthesized and incorporated into other classes of polymers, demonstrating the potential for this to be a broadly applicable method of synthesizing more easily recyclable/upcyclable crosslinked polymers.

Rapid room temperature chemical degradation of crosslinked polymers

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.