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

Youwei Ma, Xuesong Jiang, Jie Yin, Christoph Weder, José Augusto Berrocal, Zixing Shi

2022Angewandte Chemie International Edition28 citationsDOI

Abstract

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.

Topics & Concepts

Covalent bondPolymerThermal stabilityChemical modificationMaterials scienceChemical stabilityChemical bondPolymer chemistryYield (engineering)Chemical engineeringOrganic chemistryChemistryComposite materialEngineeringPolymer composites and self-healingSynthetic Organic Chemistry MethodsCarbon dioxide utilization in catalysis
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