Vinylogous Urethane Vitrimers |
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Authors: | Wim Denissen Guadalupe Rivero Renaud Nicolaÿ Ludwik Leibler Johan M Winne Filip E Du Prez |
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Institution: | 1. Department of Organic and Macromolecular Chemistry, Polymer Chemistry Research Group and Laboratory for Organic Synthesis, Ghent University, Ghent, Belgium;2. Instituto de Investigaciones en Ciencia y Tecnología de Materiales (INTEMA), Universidad Nacional de Mar del Plata, Mar del Plata, Argentina;3. Matière Molle et Chimie, UMR 7167 CNRS‐ESPCI, ESPCI ParisTech, Paris, France |
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Abstract: | Vitrimers are a new class of polymeric materials with very attractive properties, since they can be reworked to any shape while being at the same time permanently cross‐linked. As an alternative to the use of transesterification chemistry, we explore catalyst‐free transamination of vinylogous urethanes as an exchange reaction for vitrimers. First, a kinetic study on model compounds reveals the occurrence of transamination of vinylogous urethanes in a good temperature window without side reactions. Next, poly(vinylogous urethane) networks with a storage modulus of ≈2.4 GPa and a glass transition temperature above 80 °C are prepared by bulk polymerization of cyclohexane dimethanol bisacetoacetate, m‐xylylene diamine, and tris(2‐aminoethyl)amine. The vitrimer nature of these networks is examined by solubility, stress‐relaxation, and creep experiments. Relaxation times as short as 85 s at 170 °C are observed without making use of any catalyst. In addition, the networks are recyclable up to four times by consecutive grinding/compression molding cycles without significant mechanical or chemical degradation. |
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Keywords: | covalent adaptable networks enaminone exchangeable bonds vinylogous urethane vitrimers |
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