Macromolecular Research

The Polymer Society of Korea (한국고분자학회)
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Rapid Formation of Optically Active and Organosoluble Polyamides Containing L-Alaninephthalimide Side Chain via Microwave Irradiation

  • Mallakpour, Shadpour (Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology) ;
  • Rafiee, Zahra (Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology)
  • Published : 2009.11.25
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Abstract

Several aromatic optically active polyamides (PA)s were synthesized from 5-(2-phthalimidiylpropanoylamino)isophthalic acid with various aromatic diamines via direct polycondensation with triphenyl phosphite and pyridine in the presence of calcium chloride and N-methyl-2-pyrrolidone under microwave irradiation and conventional heating conditions. Under the optimized conditions, the reaction mixture was irradiated for 2 min. with a 100% irradiation power (900 W). The resulting polymers were obtained in high yield and moderate inherent viscosity ranging from 0.35 to 0.60 dL/g. All synthesized polymers showed excellent solubility in amide-type solvents. Thermogravimetric analysis revealed a 10% weight loss temperature and char yield at $600^{\circ}C$ in a nitrogen atmosphere of > $350^{\circ}C$ and > 58%, respectively, which suggests that the resulting PAs have good thermal stability.

Keywords

References

  1. P. E. Cassidy, Thermally Stable Polymer, Marcel Dekker, New York, 1980
  2. J. Preston, in Encyclopedia of Polymer Science and Technology, H. F. Mark, N. M. Bikales, C. G. Overberger, and G. Menges, Eds., Wiley-Interscience, New York, 1988
  3. L. Vollbracht, in Comprehensive Polymer Science, G. Allen and J. Bevington, Eds., Pergamon, Wheaton & Co., Exeter, England, 1989
  4. H. H. Yang, Aromatic High-Strength Fibers, Wiley-Interscience, New York, 1989
  5. S. H. Hsiao and Y. H. Chang, Eur. Polym. J., 40, 1749 (2004) https://doi.org/10.1016/j.eurpolymj.2004.04.019
  6. S. H. Hsiao, C. P. Yang, and S. C. Huang, J. Polym. Sci. Part A: Polym. Chem., 42, 2377 (2004) https://doi.org/10.1002/pola.20075
  7. D. J. Liaw, C. C. Huang, and W. H. Chen, Polymer, 47, 2337 (2006) https://doi.org/10.1016/j.polymer.2006.01.028
  8. D. J. Liaw, F. C. Chang, M. K. Leung, M. Y. Chou, and K. Muellen, Macromolecules, 38, 4024 (2005) https://doi.org/10.1021/ma048559x
  9. I. Sava and M. Bruma, Macromol. Symp., 239, 36 (2006) https://doi.org/10.1002/masy.200690107
  10. J. J. Ferreiro, J. G. De La Campa, A. E. Lozano, and J. De Abajo, J. Polym. Sci. Part A: Polym. Chem., 43, 5300 (2005) https://doi.org/10.1002/pola.21000
  11. K. H. Choi and J. C. Jung, Macromol. Mater. Eng., 289, 737 (2004) https://doi.org/10.1002/mame.200300354
  12. S. Mallakpour and Z. Rafiee, Polym. Adv. Technol., 19, 1474 (2008)
  13. R. R. Pal, P. S. Patil, M. M. Salunkhe, N. N. Maldar, and P. P. Wadgaonkar, Polym. Int., 54, 569 (2005) https://doi.org/10.1002/pi.1733
  14. S. H. Hsiao, C. P. Yang, M. H. Chuang, and S. J. Lin, J. Polym. Sci. Part A: Polym. Chem., 37, 4510 (1999) https://doi.org/10.1002/(SICI)1099-0518(19991215)37:24<4510::AID-POLA7>3.0.CO;2-0
  15. S. Mallakpour and E. Kowsari, Polym. Adv. Technol., 16, 466 (2005) https://doi.org/10.1002/pat.603
  16. S. Mallakpour and M. Kolahdoozan, e-Polymer, no.020, 1 (2006)
  17. S. Mallakpour and M. Kolahdoozan, J. Appl. Polym. Sci., 104, 1248 (2007) https://doi.org/10.1002/app.25747
  18. D. J. Liaw, F. C. Chang, J. H. Liu, K. L. Wang, K. Faghihi, S. H. Huang, K. R. Lee, and J. Y. Lai, Polym. Degrad. Stabil., 92, 323 (2007) https://doi.org/10.1016/j.polymdegradstab.2006.10.005
  19. S. Mallakpour and M. Taghavi, Polym. J., 40, 1049 (2008) https://doi.org/10.1295/polymj.PJ2008056
  20. J. M. Kim, B. J. Park, E. J. Chang, S. C. Yi, D. H. Suh, and D. J. Ahn, Macromol. Res., 13, 253 (2005) https://doi.org/10.1007/BF03219060
  21. F. Sanda and T. Endo, Macromol. Chem. Phys., 200, 2651 (1999) https://doi.org/10.1002/(SICI)1521-3935(19991201)200:12<2651::AID-MACP2651>3.0.CO;2-P
  22. R. Katsarava, Macromol. Symp., 199, 419 (2003) https://doi.org/10.1002/masy.200350935
  23. S. Mallakpour and Z. Rafiee, Iran. Polym. J., 17, 907 (2008)
  24. R. Hoogenboom, M. A. M. Leenen, F. Wiesbrock, and U. S. Schubert, Macromol. Rapid Commun., 26, 1773 (2005) https://doi.org/10.1002/marc.200500370
  25. F. Wiesbrock, R. Hoogenboom, and U. S. Schubert, Macromol. Rapid Commun., 25, 1739 (2004) https://doi.org/10.1002/marc.200400313
  26. S. Mallakpour and Z. Rafiee, Polymer, 48, 5530 (2007) https://doi.org/10.1016/j.polymer.2007.07.036
  27. S. Jing, W. Peng, Z. Yingmin, and M. Xiaojuan, Macromol. Res., 14, 659 (2006) https://doi.org/10.1007/BF03218740
  28. S. Mallakpour and Z. Rafiee, Polym. Degrad. Stabil., 93, 753 (2008) https://doi.org/10.1016/j.polymdegradstab.2008.01.028
  29. S. Mallakpour and Z. Rafiee, Polym. J., 39, 1185 (2007) https://doi.org/10.1295/polymj.PJ2007061