Chemical Upcycling of Conventional Polyureas into Dynamic Covalent Poly(aminoketoenamide)s

The chemical upcycling of polymers is an emerging strategy to transform post-consumer waste into higher-value chemicals and materials. However, on account of the high stability of the chemical bonds that constitute their main chains, the chemical modification of many polymers proves to be difficult. Here, we report a versatile approach for the upcycling of linear and cross-linked polyureas, which are widely used because of their high chemical stability. The treatment of these polymers or their composites with acetylacetone affords di-vinylogous amide-terminated compounds in good yield. These products can be reacted with aromatic isocyanates, and the resulting aminoketoenamide bonds are highly dynamic at elevated temperatures. We show here that this conversion scheme can be exploited for the preparation of dynamic covalent poly(aminoketoenamide) networks, which are healable and reprocessable through thermal treatment without any catalyst.

Automated summary

Chemical upcycling of polymers has become an emerging strategy to convert post-consumer waste into valuable chemicals and materials. However, due to the high stability of the chemical bonds in many polymers, their chemical modification is often challenging. In this study, a versatile approach for the upcycling of linear and cross-linked polyureas was developed using acetylacetone. The resulting compounds can be reacted with aromatic isocyanates to form highly dynamic aminoketoenamide bonds, enabling the preparation of healable and reprocessable poly(aminoketoenamide) networks through thermal treatment without any catalyst.