Polyimides from 2,5-bis[4-(4-aminophenoxy)benzoyl]furan and their thermal crosslinking reaction

Abstract

Several polyimides were prepared via two-step polycondensation from novel 2,5-furandicarboxylic acid–based diamine, 2,5-bis[4-(4-aminophenoxy)benzoyl]furan, with commercial dianhydrides. The chemical structures of the monomers and polymers were characterized by FT-IR and NMR in detail, respectively. The polyimides exhibited high performances with 5 wt% weight loss temperatures of over 410 oC, glass transition temperatures of over 214 oC, and tensile strengths and Young’s moduli of up to 130 MPa and 3.2 GPa, respectively. The thermal crosslinking mechanism was studied by FT-IR, Raman spectroscopy, and model reaction analysis, which showed the Diels–Alder reaction between the furan group and diphenylethylene group was the main reaction. The crosslinked polyimide films showed improved solvent resistance, and thermal and mechanical properties.

Monomers and Macromolecular Materials from Renewable Resources: State of the Art and Perspectives

“…The investigations have been more active, however, in the exploitation of the bifunctional furan-based monomers that can be prepared from 5-hydroxymethylfurfural, with a focus on 2,5-furan dicarboxylic acid, the sustainable heterocycle counterpart of terephthalic acid that may serve as platform for the preparation, for instance, of polyesters [ 128 ] and polyimides [ 129 ] with considerably reduced environmental impact. This is where poly(ethylene 2,5-furandicarboxylate) (PEF) stands, which is now in process of being scaled up to industrial levels as a (often better) replacement of PET.…”