Thermoplastic-Thermosetting Merged Polyimides Derived from Furan-Maleimide

Authors

  • Yogesh S. Patel Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Gujarat (388120), India
  • Hasmukh S. Patel Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Gujarat (388120), India

DOI:

https://doi.org/10.6000/1929-5995.2012.01.02.3

Keywords:

Diels-Alder reaction, bisfuran, bismaleimide, polyimide

Abstract

Novel thermoplastic-thermosetting merged polyimide system has been developed via Diels-Alder intermolecular reaction of bisfuran A namely, 2,5-bis(furan-2-ylmethyl carbamoyl)terephthalic acid with a series of bismaleimides B1-3 containing aliphatic chain in the backbone. The intermediate Furan - maleimide Diels-Alder adducts C1-3 were aromatized and imidized (i.e. cyclized) through carboxylic and amide groups to afford thermoplastic-thermosetting merged polyimides D1-3. Synthesized polyimides were characterized by elemental analysis, spectral features, number average molecular weight (Mn) and thermal analysis. Bulk polymerization was also carried out. Proof of structures was based mainly on a comparison of infrared spectra of polyimides with those of the corresponding model compound 4 prepared from 2-(furan-2-ylmethylcarbamoyl) benzoic acid in the similar way. FTIR spectral features of polyimides D1-3 were quite identical with the model compound 4. The ‘in situ’ void - free glass fiber reinforced composites GFRC1-3 were prepared and characterized by mechanical, electrical and chemical properties. The ‘in situ’ produced polyimides show good adhesion to glass fibers. All the composites depicted good mechanical and electrical properties and good resistance to organic solvents and mineral acids.

References

Adadie MJM, Sillion B. Polyimides and other High-Temperature Polymers, Elsevier Science Publishers, Amsterdam 1991.

Ghosh MK, Mittal KL. Polyimides–fundamentals and applications. New York: Marcel Dekker 1996.

Tesoro GC, Sastri VR. Synthesis of siloxane-containing bis(furans) and polymerization with bis (ma1eimides). Ind Eng Chem Prod Res Dev 1986; 25(3): 444-48. http://dx.doi.org/10.1021/i300023a013 DOI: https://doi.org/10.1021/i300023a013

Gaina C, Ursache O, Gaina V, Buruiana E, Ionita D. Investigation on the thermal properties of new thermo-reversible networks based on poly(vinyl furfural) and multi functional maleimide compounds. Express Polym Lett 2012; 6(2): 129-41. DOI: https://doi.org/10.3144/expresspolymlett.2012.14

Patel DG, Graham KR, Reynolds JR. A Diels–Alder crosslinkable host polymer for improved PLED performance: the impact on solution processed doped device and multilayer device performance. J Mater Chem 2012; 22: 3004-14. http://dx.doi.org/10.1039/c2jm14591j DOI: https://doi.org/10.1039/c2jm14591j

Sanyal A. Diels–Alder cycloaddition– cycloreversion: a powerful combo in materials design. Macromol Chem Phys 2010; 211: 1417-25. http://dx.doi.org/10.1002/macp.201000108 DOI: https://doi.org/10.1002/macp.201000108

Peterson AM, Jensen RE, Palmese GR. Thermoreversible and remendable glass–polymer interface for fiber-reinforced composites. Compos Sci Technol 2011; 71: 586-92. http://dx.doi.org/10.1016/j.compscitech.2010.11.022 DOI: https://doi.org/10.1016/j.compscitech.2010.11.022

Liu YL, Chen YW. Thermally reversible cross-linked polyamides with high toughness and self-repairing ability from maleimide and furan-functionalized aromatic polyamides. Macromol Chem Phys 2007; 208: 224-32. http://dx.doi.org/10.1002/macp.200600445 DOI: https://doi.org/10.1002/macp.200600445

Gandini A. The furan / maleimide Diels-Alder reaction: A versatile click–unclick tool in macro molecular synthesis. Prog Polym Sci 2012; in press. http://dx.doi.org/10.1016/j.progpolymsci.2012.04.002 DOI: https://doi.org/10.1016/j.progpolymsci.2012.04.002

Gandini A, Coelho D, Silvestre AJD. Reversible click chemistry at the service of macromolecular materials. Polym Chem 2011; 2: 1713-19. http://dx.doi.org/10.1039/c1py00125f DOI: https://doi.org/10.1039/c1py00125f

Prabhu KG, Patel HS. Modified polyimides based on epoxy resin (Part 2). Int J Polym Mater 2001; 50: 93-107. http://dx.doi.org/10.1080/00914030108035093 DOI: https://doi.org/10.1080/00914030108035093

Patel HS, Patel VC. Polyimides containing s-triazine ring, Eur Polym J 2001; 37: 2263-71. http://dx.doi.org/10.1016/S0014-3057(01)00107-0 DOI: https://doi.org/10.1016/S0014-3057(01)00107-0

Patel HS, Patel SR. Novel polyimide system based on nitro displacement/Diels-Alder reactions. Int J Polym Mater 2007; 56: 1-12. http://dx.doi.org/10.1080/00914030600692588 DOI: https://doi.org/10.1080/00914030600692588

Patel HS, Patel BP, Patel DB. Synthesis characterization and glass reinforcement of poly (ester amido imide)s. Int J Polym Mater 2009; 58: 625-35. http://dx.doi.org/10.1080/00914030903081547 DOI: https://doi.org/10.1080/00914030903081547

Patel HS, Patel JA. Synthesis, characterization and glass reinforcement of poly (amido-imide)s part-3. Polym Plast Technol Eng 2009; 48: 102-09. http://dx.doi.org/10.1080/03602550802539924 DOI: https://doi.org/10.1080/03602550802539924

Patel HS, Patel BP, Patel DB. Synthesis, characterization and material application of poly (ester-oxysilane-imide)s having epoxy residues. Polym Plast Technol Eng 2010; 49: 394-99. http://dx.doi.org/10.1080/03602550903532158 DOI: https://doi.org/10.1080/03602550903532158

Patel BP, Patel HS, Patel DB. Glass reinforcement of epoxy resin based Poly (urethane-imide-ester)s. Int J Plast Technol 2011; 15(2): 163-73. http://dx.doi.org/10.1007/s12588-012-9021-9 DOI: https://doi.org/10.1007/s12588-012-9021-9

Patel HS, Patel SR, Dixit BC. Novel semi-interpenetrating polyimide network based on acryl end capped oligoimides. J Polym Res 2006; 13: 461-67. http://dx.doi.org/10.1007/s10965-006-9067-5 DOI: https://doi.org/10.1007/s10965-006-9067-5

Patel YS, Patel HS, Srinivasulu B. Synthesis, spectral, magnetic, thermal and biological aspects of pyromellitic dianhydride based co-ordination polymers. Int J Plast Technol 2012; in press. http://dx.doi.org/10.1007/s12588-012-9035-3 DOI: https://doi.org/10.1007/s12588-012-9035-3

Belina K. Thermal stability of aliphatic polyimides. J Thermal Anal 1997; 50: 655-63. http://dx.doi.org/10.1007/BF01979037 DOI: https://doi.org/10.1007/BF01979037

Silverstein RM, Webste FX. Spectrometric Identification of Organic Compounds, 6th ed. John Wiley & Sons: New York 2004.

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Published

2013-01-10

How to Cite

Patel, Y. S., & Patel, H. S. (2013). Thermoplastic-Thermosetting Merged Polyimides Derived from Furan-Maleimide . Journal of Research Updates in Polymer Science, 1(2), 75–83. https://doi.org/10.6000/1929-5995.2012.01.02.3

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