Dynamic β-Amino Sulfonamides for the Synthesis of Covalent Adaptable Networks
Year: 2025
Type: article
Abstract: Thermosets are indispensable for their lightweight and excellent thermomechanical properties but suffer from nonrecyclability, exacerbating plastic pollution. Covalent Adaptable Networks (CANs), leveraging dynamic covalent bonds, address this challenge. This study explores β-amino sulfonamides (BASA) as novel dynamic and thermoreversible linkers for CANs. Compared to previously investigated β-amino amides (BAAs), small molecule BASA studies show a faster amine exchange reaction via (retro)aza-Michael reactions in a temperature window from 140 to 180 °C. More importantly, in contrast to the acrylamide monomers released from BAAs, the vinyl sulfonamide monomers released from BASAs are more robust and can resist homopolymerization at elevated temperatures. We showed that bisfunctional vinyl sulfonamide cross-linkers enable the synthesis of CANs with tunable properties, as verified through thermomechanical and rheological analysis. The anticipated increased thermal stability of BASA-based CANs was shown by the retention of mechanical and rheological performance over at least five recycling cycles.
Source: ACS Macro Letters
Institution: Ghent University
Language: English
Subfield: Polymers and Plastics
Field: Materials Science
Domain: Physical Sciences
Open Access status: green
Awards: Magnetic resonance equipment for advanced material research: molecular characterisation of solid, soft, homogeneous and heterogeneous matter for the development of advanced functional materials and chemical catalysis, Circular Thermoset Materials: How to exploit Precision Engineered Macromolecules in their Bottom-up Design?, Probing the molecular and nanoscale structure of covalent adaptable networks with solid state NMR and X-Ray techniques for improved material design (RESONANCE), G449221245
OpenAlex ID: W4415749140