Synhesis of piperazine based polyimide in the presence of ionic liquids

Synhesis of piperazine based polyimide in the presence of ionic liquids

Ionic liquids derived from imidazolium, pyridinium, and alkylammonium salts were investigated not only as catalysts but also as solvents in polymerization of 1,4-bis(3-aminopropyl) piperazine. Results were compared with the conventional polymerizations in N-methylpyrrolidone (NMP). The catalyst has not only a detectable influence on polymer solubility, but also the degrees of polymerization are notably higher. They are even greater than the values obtained by conventional 2-stage polymerization in organic liquids. Ionic liquids based on imidazolium salts seem preferable over pyridinium and alkylammonium salts due to the higher degree of polydispersity of the polyimides obtained. The glass transition temperatures and thermal stabilities were higher for polyimide synthesized in ionic liquids than conventional polyimides prepared in aprotic solvents.

___

  • 1. J.S. Moulthrop, R.P. Swatloski, G. Moyna and R.D. Rogers, Chem. Commun. 1557-1559 (2005).
  • 2. H.M. Luo, S. Dai, P.V. Bonnesen, A.C. Buchanan, J.D. Holbrey, N.J. Bridges and R.D. Rogers, Anal. Chem. 76, 3078-3083 (2004).
  • 3. J.H. Li, Y.F. Shen, Y.J. Zhang and Y. Liu, Chem. Commun. 360-362 (2005).
  • 4. (a) Z.Y. Li, H.T. Liu, Y. Liu, P. He and J.H. Li, J . Phys. Chem. B. 108, 17512-17518 (2004). (b) Y. Liu, M.J. Wang, Z.Y. Li, H.T. Liu, P. He and J.H. Li, Langmuir 21, 1618-1622 (2005). (c) M.C. Buzzeo, C. Hardacre and R.G. Compton, Anal. Chem. 76, 4583-4588 (2004).
  • 5. (a) S. Park and R. Kazlauskas, Curr. Opin. Biotechnol. 14, 432-437 (2003). (b) M.F. Machadoand J.M. Saraiva, Biotechnol. Lett. 27, 1233-1239 (2005). (c) W.Y. Lou, M.H. Zong and H. Wu, Biocatal. Biotransform. 22, 171-176 (2004). (d) F. Zhao, X.E. Wu, M.K. Wang, Y. Liu, L.X. Gao and S. Dong, J. Anal. Chem. 76, 4960-4967 (2004). (e) Y. Liu, M. Wang, J. Li, P. He, H.T. Liu and J.H. Li, Chem. Commun. 1778-1780 (2005).
  • 6. H. Huang, N.F. Hu, Y.H. Zeng and G. Zhou, Anal. Biochem. 308, 141-151 (2002).
  • 7. R.D. Rogers, K.R. Seddon “Ionic Liquids Industrial Applications to Green Chemistry”, ACS Symposium Series 818, American Chemical Society, Washington, DC, 2002.
  • 8. R.D. Rogers, K.R. Seddon, P. Kubisa, “Ionic Liquids as Green Solvents”, ACS Symposium Series 856, American Chemical Society, Washington, DC, 2003.
  • 9. V. Strehmel, A. Laschewsky, H. Kraudelt, H. Wetzel, E. Gornitz, In ACS Symposium Series 913; R.D. Rogers, C.S. Brazel, Eds.; American Chemical Society, Washington, DC, pp 17-36, 2005.
  • 10. P. Kubisa, Prog. Polym. Sci. 29, 3-12 (2004).
  • 11. D.A. Canelas and J.M. DeSimone, Adv. Polym. Sci. 133, 103-140 (1997).
  • 12. H. Zhang, L. Bu. M. Li, K. Hong, A.E. Visser, R.D. Rogers and J.W. Mays, ACS Symposium Series 818; R.D. Rogers, K.R. Seddon, Eds.; American Chemical Society: Washington, DC; pp 114-123, 2002.
  • 13. (a) M.G. Benton and C.S. Brazel, ACS Symposium Series 818; R.D. Rogers, K.R. Seddon, Eds.; American Chemical Society: Washington, DC; pp 125-133, 2002. (b) K. Hong, H. Zhang, J.W. Mays, A.E. Visser, C.S. Brazel, J.D. Holbrey, W.M. Reichert and R. Rogers, Chem. Commun. 1368-1369 (2002). (c) H. Zhang, K. Ho ng, J.W. Mays, Macromolecules 35, 5738-5741 (2002).
  • 14. S. Harrison, S.R. Mackenzie and D.M. Haddleton, Chem. Commun. 2850-2851 (2002).
  • 15. S. Harrison, S.R. Mackenzie, D.M. Haddleton, Macromolecules 36, 5072-5075 (2003).
  • 16. S. Perrier, T.P. Davis, A.J. Carmichael and D.M. Haddleton, Eur. Polym. J. 39, 417-422 (2003).
  • 17. T. Biedron and P. Kubisa, Macromol. Rapid Commun. 22, 1237-1242 (2001).
  • 18. T. Biedron and P. Kubisa, J. Polym. Sci., Polym. Chem. Ed. 40, 2799-2809 (2002).
  • 19. T. Biedron and P. Kubisa, Polym. Int. 52, 1584-1588 (2003).
  • 20. H. Ma, X. Wan, X. Chen and Q.F. Zhou, J. Polym. Sci., Polym. Chem. Ed. 41, 143-151 (2003).
  • 21. H. Ma, X. Wan, X. Chen and Q.F. Zhou, Polymer 36, 5072-5075 (2003).
  • 22. R. Vijayaraghavan and D.R. MacFarlane, Aust. J . Chem. 57, 129-133 (2004).
  • 23. S. Ding, M. Rodosz and Y. Shen, Macromolecules 38, 5921-5928 (2005).
  • 24. T. Biedron and P. Kubisa, J. Polym. Sci., Part A Polym. Chem. 43, 3454-3459 (2005).
  • 25. K.H. Shaughnessy, M.A. Klingshirn, S.J. P’Pool, J.D. Holbrey and R.D. Rogers, ACS Symp. Ser. 856, 300-313 (2003).
  • 26. M.F. Pinheiro, R.S. Mauler and R.F. de Souza, Macromol. Rapid Commun. 22, 425-428 (2001).
  • 27. R. Vijayaraghavan and D.R. MacFarlane, Chem. Commun. 700-701 (2004).
  • 28. T. Biedron and P. Kubisa, J. Polym. Sci., Part A Polym. Chem. 42, 3230-3235 (2004).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Synthesis of Piperazine Based Polyimide in the Presence of Ionic Liquids

Bülent ALICI, Süleyman Köytepe And Turgay SEÇKİN

The direct electrochemical synthesis of Ti(II), Fe(II), Cd(II), Sn(II), and Pb(II) complexes with N, N'-bis(salicylidene)-o-phenylenediamine

Bing ZHANG, Jianning LIU, Bowan WU, Kejun ZHANG, Shenli HU

Synhesis of piperazine based polyimide in the presence of ionic liquids

Turgay SEÇKİN, Bülent ALICI, Süleyman KÖYTEPE

The Effect of Ionic Electrolytes and pH on the Zeta Potential of Fine Coal Particles

Kemal DOYMUŞ

Synthesis of New 5-Aryl Pyrido [3´, 2´: 4, 5] Thieno [2, 3-e] [1, 2, 3, 4] Tetrazolo [1, 5-c}] Pyrimidine Derivatives

Abolghasem DAVOODNIA, Mehdi BAKAVOLI, Mahsan BASHASH

The Direct Electrochemical Synthesis of Ti(II), Fe(II), Cd(II), Sn(II), and Pb(II) Complexes with N, N´-Bis(Salicylidene)-o-Phenylenediamine

Jianning LIU, Bing ZHANG, Bowan WU, Kejun ZHANG, Shenli HU

Preconcentration of Trace Elements on Amberlite XAD-4 Resin Functionalised with 1,2-bis (o-aminophenylthio) Ethane and Their Determination by FAAS in Environmental Samples

Ömer DALMAN, Volkan Numan BULUT

Synthesis of the Amide Derivatives of 3-[1-(3-Pyridazinyl)-5-phenyl-1H-pyrazole-3-yl]propanoic Acids as Potential Analgesic Compounds

Erden BANOĞLU, Murat ŞÜKÜROĞLU, Burcu Çalişkan ERGÜN

Synthesis and characterization of $NiFe_2O_4$ nano-octahedrons by EDTA-assisted hydrothermal method

Harun BAYRAKDAR, Abdulhadi BAYKAL, Nermin KASAPOĞLU, Muhammet S. TOPRAK, Yüksel KÖSEOĞLU

Dinuclear Molybdenum Tetracarbonyl Complexes of Tetradentate Nitrogen Ligands and Intermolecular Hydrogen Bonding in the Crystal Structure of N,N´-bis-[1-(pyridin-2-yl)ethylidene]-ethane-1,2-diamine

Ayfer MENTEŞ, Seda SEZEK, M. Emre HANHAN