Synthesis 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.
Synthesis 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.
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- J.S. Moulthrop, R.P. Swatloski, G. Moyna and R.D. Rogers, Chem. Commun. 1557-1559 (2005).
- H.M. Luo, S. Dai, P.V. Bonnesen, A.C. Buchanan, J.D. Holbrey, N.J. Bridges and R.D. Rogers, Anal. Chem. , 3078-3083 (2004).
- J.H. Li, Y.F. Shen, Y.J. Zhang and Y. Liu, Chem. Commun. 360-362 (2005).
- (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).
- (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).
- H. Huang, N.F. Hu, Y.H. Zeng and G. Zhou, Anal. Biochem. 308, 141-151 (2002).
- R.D. Rogers, K.R. Seddon “Ionic Liquids Industrial Applications to Green Chemistry”, ACS Sympo- sium Series 818, American Chemical Society, Washington, DC, 2002.
- R.D. Rogers, K.R. Seddon, P. Kubisa, “Ionic Liquids as Green Solvents”, ACS Symposium Series 856, American Chemical Society, Washington, DC, 2003.
- 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.
- P. Kubisa, Prog. Polym. Sci. 29, 3-12 (2004).
- D.A. Canelas and J.M. DeSimone, Adv. Polym. Sci. 133, 103-140 (1997).
- 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.
- (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).
- S. Harrison, S.R. Mackenzie and D.M. Haddleton, Chem. Commun. 2850-2851 (2002).
- S. Harrison, S.R. Mackenzie, D.M. Haddleton, Macromolecules 36, 5072-5075 (2003).
- S. Perrier, T.P. Davis, A.J. Carmichael and D.M. Haddleton, Eur. Polym. J. 39, 417-422 (2003).
- T. Biedron and P. Kubisa, Macromol. Rapid Commun. 22, 1237-1242 (2001).
- T. Biedron and P. Kubisa, J. Polym. Sci., Polym. Chem. Ed. 40, 2799-2809 (2002).
- T. Biedron and P. Kubisa, Polym. Int. 52, 1584-1588 (2003).
- H. Ma, X. Wan, X. Chen and Q.F. Zhou, J. Polym. Sci., Polym. Chem. Ed. 41, 143-151 (2003).
- H. Ma, X. Wan, X. Chen and Q.F. Zhou, Polymer 36, 5072-5075 (2003).
- R. Vijayaraghavan and D.R. MacFarlane, Aust. J . Chem. 57, 129-133 (2004).
- S. Ding, M. Rodosz and Y. Shen, Macromolecules 38, 5921-5928 (2005).
- T. Biedron and P. Kubisa, J. Polym. Sci., Part A Polym. Chem. 43, 3454-3459 (2005).
- K.H. Shaughnessy, M.A. Klingshirn, S.J. P’Pool, J.D. Holbrey and R.D. Rogers, ACS Symp. Ser. 856, 313 (2003).
- M.F. Pinheiro, R.S. Mauler and R.F. de Souza, Macromol. Rapid Commun. 22, 425-428 (2001).
- R. Vijayaraghavan and D.R. MacFarlane, Chem. Commun. 700-701 (2004).
- T. Biedron and P. Kubisa, J. Polym. Sci., Part A Polym. Chem. 42, 3230-3235 (2004).
- R. Vijayaraghavan and D.R. MacFarlane, Chem. Commun. 1149-1151 (2005).
- H. Uyama, T. Takamoto and S. Kobayashi, Polym. J. Jpn. 34, 94-96 (2002).
- E. Naudin, H.A. Ho, S. Branchaud, L. Breau and D. Belanger, J . Phys. Chem. B 106, 10585-10593 (2002).
- P. Wasserscheid, C.M. Gordon, C. Hilgers, M.J. Muldoon and I.R. Dunkin, Chem. Commun. 1186-1187 (2001).
- J.M. Pringle, M. Forsyth, D.R. MacFarlane, K. Wagner, S.B. Hall and D.L. Officer, Polymer 46, 2047-2058 (2005).
- Y.S. Vygodskii, E.I. Lozinskaya, A.S. Shaplov, K.A. Lyssenko, M.Y. Antipin and Y.G. Urman, Polymer 45, 5045 (2004).
- E.I. Lozinskaya, A.S. Shaplov and Y.S. Vygodskii, Eur. Polym. J. 40, 2065-2075 (2004).
- H. Zhang, K. Hong, M. Jablonsky and J.W. Mays, Chem. Commun. 1356-1357 (2003).
- L. Chen, Y.M. Zhang and H.P. Wang, Macromol. Symp. 216, 9-16 (2004).
- G.Z. Wu, Y.D. Liu and D.W. Lpong, Macromol. Rapid Commun. 26, 57-61 (2005).