Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization

Novel thermoplastic-thermosetting merged polyimide system has been developed via Diels–Alder intermolecular polymerization of bisfuran namely, 2,5-bis(furan-2-ylmethylcarbamoyl) terephthalic acid A with a series of bismaleimides B1–4. Thus obtained intermediate Diels–Alder adducts C1–4 were aromatiz...

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Main Authors: Yogesh S. Patel, Hasmukh S. Patel
Format: Article
Language:English
Published: Elsevier 2017-02-01
Series:Arabian Journal of Chemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S1878535213000993
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author Yogesh S. Patel
Hasmukh S. Patel
author_facet Yogesh S. Patel
Hasmukh S. Patel
author_sort Yogesh S. Patel
collection DOAJ
description Novel thermoplastic-thermosetting merged polyimide system has been developed via Diels–Alder intermolecular polymerization of bisfuran namely, 2,5-bis(furan-2-ylmethylcarbamoyl) terephthalic acid A with a series of bismaleimides B1–4. Thus obtained intermediate Diels–Alder adducts C1–4 were aromatized and imidized (i.e. cyclized) through carboxylic and amide groups to afford thermoplastic-thermosetting merged polyimides D1–4. Bisfuran A was prepared by the condensation of pyromellitic dianhydride with furan-2-ylmethanamine and characterized by elemental, spectral, thermal and LCMS analyses. Synthesized Diels–Alder adducts C1–4 and polyimides D1–4 were characterized by elemental analysis, spectral features, number average molecular weight (Mn‾), degree of polymerization (DP) and thermal analysis. To facilitate the correct structural assessment and to be able to verify the occurrence of the DA adducts and PIs, a model compound 4 was prepared from phthalic anhydride and furan-2-ylmethanamine in a similar way. FTIR spectral features of polyimides D1–4 were compared with model compound 4 and they were found to be quite identical. The ‘in situ' void-free glass fiber reinforced composites GFRC1–4 were prepared from the produced system and characterized by chemical, mechanical and electrical analyses. All the composites showed good mechanical, electrical and thermal properties and good resistance to organic solvents and mineral acids.
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spelling doaj.art-92b7b7f2e3fe48c4abb1398f765192732022-12-22T01:15:37ZengElsevierArabian Journal of Chemistry1878-53522017-02-0110S1S1373S138010.1016/j.arabjc.2013.04.010Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerizationYogesh S. PatelHasmukh S. PatelNovel thermoplastic-thermosetting merged polyimide system has been developed via Diels–Alder intermolecular polymerization of bisfuran namely, 2,5-bis(furan-2-ylmethylcarbamoyl) terephthalic acid A with a series of bismaleimides B1–4. Thus obtained intermediate Diels–Alder adducts C1–4 were aromatized and imidized (i.e. cyclized) through carboxylic and amide groups to afford thermoplastic-thermosetting merged polyimides D1–4. Bisfuran A was prepared by the condensation of pyromellitic dianhydride with furan-2-ylmethanamine and characterized by elemental, spectral, thermal and LCMS analyses. Synthesized Diels–Alder adducts C1–4 and polyimides D1–4 were characterized by elemental analysis, spectral features, number average molecular weight (Mn‾), degree of polymerization (DP) and thermal analysis. To facilitate the correct structural assessment and to be able to verify the occurrence of the DA adducts and PIs, a model compound 4 was prepared from phthalic anhydride and furan-2-ylmethanamine in a similar way. FTIR spectral features of polyimides D1–4 were compared with model compound 4 and they were found to be quite identical. The ‘in situ' void-free glass fiber reinforced composites GFRC1–4 were prepared from the produced system and characterized by chemical, mechanical and electrical analyses. All the composites showed good mechanical, electrical and thermal properties and good resistance to organic solvents and mineral acids.http://www.sciencedirect.com/science/article/pii/S1878535213000993BisfuranBismaleimideDiels–Alder reactionThermoplastic-thermosetting merged polyimideThermal analysis
spellingShingle Yogesh S. Patel
Hasmukh S. Patel
Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization
Arabian Journal of Chemistry
Bisfuran
Bismaleimide
Diels–Alder reaction
Thermoplastic-thermosetting merged polyimide
Thermal analysis
title Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization
title_full Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization
title_fullStr Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization
title_full_unstemmed Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization
title_short Thermoplastic-thermosetting merged polyimides via furan-maleimide Diels–Alder polymerization
title_sort thermoplastic thermosetting merged polyimides via furan maleimide diels alder polymerization
topic Bisfuran
Bismaleimide
Diels–Alder reaction
Thermoplastic-thermosetting merged polyimide
Thermal analysis
url http://www.sciencedirect.com/science/article/pii/S1878535213000993
work_keys_str_mv AT yogeshspatel thermoplasticthermosettingmergedpolyimidesviafuranmaleimidedielsalderpolymerization
AT hasmukhspatel thermoplasticthermosettingmergedpolyimidesviafuranmaleimidedielsalderpolymerization