Synthesis of thermoplastic–thermosetting merged polyimides by use of the Diels–Alder reaction

Synthesis of thermoplastic–thermosetting merged polyimides by use of the Diels–Alder reaction Novel thermoplastic–thermosetting merged polyimides (PIs) have been developed by Diels–Alder (DA) intermolecular reaction of the bisfuran 2,5-bis(furan-2-ylmethylcarbamoyl)terephthalic acid A with a series of bismaleimides, viz., m,m′-dimethyl p,p′-dimaleimidobiphenyl (B 1 ), m,m′-dimethoxy p,p′-dimaleimidobiphenyl (B 2 ), 1,1′-bis(4-maleimidophenyl)cyclohexane (B 3 ), and 2,2′-bis-[4-(4-maleimidephenoxy)phenyl]propane (B 4 ). The intermediate DA adducts obtained, C 1–4 , were aromatized and imidized (i.e. cyclized) through the carboxyl and amide groups to afford thermoplastic–thermosetting merged PIs D 1–4 . Bisfuran A was prepared by condensation of pyromellitic dianhydride with furan-2-ylmethanamine and duly characterized. Synthesized DA adducts and PIs were characterized by use of elemental analysis, spectral features, number average molecular weight, degree of polymerization, and thermal analysis. To facilitate the correct structure assignment and to verify the identities of the DA adducts and PIs, a model compound 4 was prepared in a similar way from phthalic anhydride and furan-2-ylmethanamine. FT-IR spectral features of PIs D 1–4 were compared with those of model compound 4 and found to be identical. Glass fiber-reinforced composites GFRC 1–4 were prepared from this system and characterized by chemical, mechanical, and electrical analysis. All the composites had good mechanical, electrical, and thermal properties and good resistance to organic solvents and mineral acids. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Synthesis of thermoplastic–thermosetting merged polyimides by use of the Diels–Alder reaction

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Publisher
Springer Netherlands
Copyright
Copyright © 2013 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-013-1389-4
Publisher site
See Article on Publisher Site

Abstract

Novel thermoplastic–thermosetting merged polyimides (PIs) have been developed by Diels–Alder (DA) intermolecular reaction of the bisfuran 2,5-bis(furan-2-ylmethylcarbamoyl)terephthalic acid A with a series of bismaleimides, viz., m,m′-dimethyl p,p′-dimaleimidobiphenyl (B 1 ), m,m′-dimethoxy p,p′-dimaleimidobiphenyl (B 2 ), 1,1′-bis(4-maleimidophenyl)cyclohexane (B 3 ), and 2,2′-bis-[4-(4-maleimidephenoxy)phenyl]propane (B 4 ). The intermediate DA adducts obtained, C 1–4 , were aromatized and imidized (i.e. cyclized) through the carboxyl and amide groups to afford thermoplastic–thermosetting merged PIs D 1–4 . Bisfuran A was prepared by condensation of pyromellitic dianhydride with furan-2-ylmethanamine and duly characterized. Synthesized DA adducts and PIs were characterized by use of elemental analysis, spectral features, number average molecular weight, degree of polymerization, and thermal analysis. To facilitate the correct structure assignment and to verify the identities of the DA adducts and PIs, a model compound 4 was prepared in a similar way from phthalic anhydride and furan-2-ylmethanamine. FT-IR spectral features of PIs D 1–4 were compared with those of model compound 4 and found to be identical. Glass fiber-reinforced composites GFRC 1–4 were prepared from this system and characterized by chemical, mechanical, and electrical analysis. All the composites had good mechanical, electrical, and thermal properties and good resistance to organic solvents and mineral acids.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Sep 22, 2013

References

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