Bio-Based Aromatic Polyesters Reversibly Crosslinked via the Diels–Alder Reaction

Diphenolic acid is functionalized with furfuryl amine and subsequently incorporated in a (partly) bio-based polyester through interfacial polycondensation with terepthalic chloride. The furan groups present in the resulting polyester are able to form a thermoreversible covalent network with differen...

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Bibliographic Details
Published in:Applied sciences Vol. 12; no. 5; p. 2461
Main Authors: Beljaars, Martijn, Heeres, Hero J., Broekhuis, Antonius A., Picchioni, Francesco
Format: Journal Article
Language:English
Published: Basel MDPI AG 01.03.2022
Subjects:
Acids
bio-based
bismaleimide
Bisphenol A
Carbon footprint
Chemicals
furan
Hydrocarbons
Phenols
polyester
Polymerization
Recycling
Renewable resources
short-chain
thermoreversibility
ISSN:2076-3417, 2076-3417
Online Access:Get full text
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Summary:Diphenolic acid is functionalized with furfuryl amine and subsequently incorporated in a (partly) bio-based polyester through interfacial polycondensation with terepthalic chloride. The furan groups present in the resulting polyester are able to form a thermoreversible covalent network with different bismaleimide moieties via the Diels–Alder (DA) reaction. Our analysis of the polymer network by 1H-NMR clearly shows the formation of both possible stereoisomers (endo and exo) from the Diels–Alder coordination of furan and maleimide. Furthermore, it was found that these isomers can be reversibly interchanged at temperatures below the reported retro Diels–Alder reaction temperature, a phenomenon often claimed but, until present, never directly observed, for thermally reversible polymeric systems. Finally, a proof of principle for reversibility and recyclability is shown.
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ISSN:2076-3417
2076-3417
DOI:10.3390/app12052461