Abstract
A series of new asymmetric biphenyl dianhydrides, 2-phenoxy(o-methylphenoxy, m-methylphenoxy, and p-methylphenoxy)-4,4,5,5-biphenyltetracarboxylic dianhydrides, was readily synthesized using a five-step route. A new symmetric biphenyl dianhydride, 2,2-di(o-methylphenoxy)-4,4,5,5-biphenyltetracarboxylic dianhydride, was also synthesized using the similar procedure. The polyimides were prepared from such new dianhydrides and commercial diamines by high-temperature one-step polymerization. The asymmetric and symmetric substituent solubility and thermal property relationships of the resulting polyimides were investigated. Interestingly, the thermally reversible sol-gel transitions were observed for the polymer solutions of the polyimides derived from those asymmetric dianhydrides and 1,4-phenylenediamine (p-PDA). Unexpectedly, the polyimides derived from asymmetric dianhydrides did not show better organosolubility than those of the homologous polyimides derived from symmetric dianhydrides. The structures of the substituents (phenoxy, o-methylphenoxy, m-methylphenoxy and p-methylphenoxy) have a significant effect on both the solubility and the thermal properties of these polyimides. The polyimides derived from asymmetric dianhydrides show enhanced thermal properties relative to the symmetric dianhydridesderived polyimides. These results can be attributed to their different degrees of molecular packing revealed by wideangle X-ray diffraction measurements.
Similar content being viewed by others
References
M. K. Ghosh and K. L. Mittal, Eds., Polyimides: Fundamentals, and Applications, Marcel Dekker, New York, 1996.
C. E. Sroog, J. Polym. Sci. Macromol. Rev., 11, 161 (1976).
F. W. Harris, Polyimides, D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother, Eds., Chapman and Hall, New York, 1990.
P. M. Hergenrother and S. J. Havens, Macromolecules, 27, 4659 (1994).
C. P. Yang and W. T. Chen, Macromolecules, 26, 4865 (1993).
A. S. Hay and W. G. Kim, Macromolecules, 26, 5275 (1993).
S. Trofimenko and B. C. Auman, Macromolecules, 27, 1136 (1994).
J. A. Mikroyannidis, Macromolecules, 28, 5177 (1995).
M. H. Yi, W. X. Huang, M. Y. Jin, and K. Y. Choi, Macromolecules, 30, 5606 (1997).
J. A. Mikroyannidis, and I. K. Spiliopoulos, Macromolecules, 31, 1236 (1998).
D. Ayala, A. E. Lozano, J. D. Abajo, and J. G. De la Campa, J. Polym. Sci. Part A: Polym. Chem., 37, 805 (1999).
S. Z. D. Cheng, F. E. Arnold, A. Q. Zhang, S. L. C. Hsu, and F. W. Harris, Macromolecules, 24, 5856 (1991).
T. Matsuura, N. Yamada, S. Nishi, and Y. Hasuda, Macromolecules, 26, 419 (1993).
H. S. Kim, Y. H. Kim, S. K. Ahn, and S. K. Kwon, Macromolecules, 36, 2327 (2003).
S. H. Lin, F. M. Li, S. Z. D. Cheng, and F. W. Harris, Macromolecules, 31, 2080 (1998).
F. W. Harris, S. H. Lin, F. M. Li, and S. Z. D. Cheng, Polymer, 37, 5049 (1996).
D. J. Liaw, B. Y. Liaw, and M. Q. Jeng, Polymer, 39, 1597 (1998).
D. J. Liaw, F. C. Chang, M. K. Leung, M. Y. Chou, and K. Muellen, Macromolecules, 38, 4024 (2005).
T. Matsuura, Y. Hasuda, S. Nishi, and N. Yamada, Macromolecules, 24, 5001 (1991).
T. Matsuura, M. Ishizawa, Y. Hasuda, and S. Nishi, Macromolecules, 25, 3540 (1992).
D. J. Liaw, P. N. Hsu, W. H. Chen, and S. L. Lin, Macromolecules, 35, 4669 (2002).
D. J. Liaw, B. Y. Liaw, P. N. Hsu, and C. Y. Hwang, Chem. Mater., 13, 1811 (2001).
D. J. Liaw and B. Y. Liaw, Macromol. Chem. Phys., 199, 1473 (1998).
W. M. Li, S. H. Li, Q. Y. Zhang, and S. B. Zhang, Macromolecules, 40, 8205 (2007).
Z. Y. Wang and Y. Qi, Macromolecules, 28, 4207 (1995).
M. Yamada, M. Kusama, T. Matsumoto, and T. Kurosaki, Macromolecules, 26, 4961 (1993).
M. Kusama, T. Matsumoto, and T. Kurosaki, Macromolecules, 27, 1117 (1994).
T. Matsumoto and T. Kurosaki, Macromolecules, 30, 993 (1997).
J. G. Liu, M. H. He, H. W. Zhou, Z. G. Qian, F. S. Wang, and S. Y. Yang, J. Polym. Sci. Part A: Polym. Chem., 40, 110 (2002).
H. Seino, A. Mochizuki, and M. Ueda, J. Polym. Sci. Part A: Polym. Chem., 37, 3584 (1999).
F. M. Li, J. J. Ge, P. S. Honigfort, S. Fang, J. C. Chen, F. W. Harris, and S. Z. D. Cheng, Polymer, 40, 4987 (1999).
F. M. Li, J. J. Ge, P. S. Honigfort, S. Fang, J. C. Chen, F. W. Harris, and S. Z. D Cheng, Polymer, 40, 4571 (1999).
Z. M. Qiu and S. B. Zhang, Polymer, 46, 1693 (2005).
I. S Chung and S. Y. Kim, Macromolecules, 33, 3190 (2000).
H. B. Zheng and Z. Y. Wang, Macromolecules, 33, 4310 (2000).
H. Yagci and L. J. Mathias, Polymer, 39, 3779 (1998).
C. P. Yang, Y. Y. Su, and K. L. Wu, J. Polym. Sci. Part A: Polym. Chem., 42, 5424 (2004).
D. J. Liaw and B. Y. Liaw, J. Polym. Sci. Part A: Polym. Chem., 35, 1527 (1997).
C. L. Gao, X. E. Wu, G. H. Lv, M. X. Ding, and L. X. Gao, Macromolecules, 37, 2754 (2004).
Y. T. Chern and J. Y. Tsai, Macromolecules, 41, 9556 (2008).
M. Hasegawa, N. Sensui, Y. Shindo, and R. Yokota, Macromolecules, 32, 387 (1999).
T. Kyu, J. C. Yang, S. Z. D. Cheng, S. L. C. Hsu, and F. W. Harris, Macromolecules, 27, 1861 (1994).
W. Risse and D. Y. Sogah, Macromolecules, 23, 4029 (1990).
R. E. Dickerson, H. B. Gray, M. Y. Darensbourg, and D. J. Darensbourg, in Chemical Principles, 4th ed., Benjamin Cummings, Menlo Park, 1984, p 565.
J. C. Coburn and M. T. Pottiger, in Polyimides: Fundamentals and Applications, M. K. Ghosh and K. L. Mittal, Eds., Marcel Dekker, New York, 1996, p 207.
X. Y. Liu, L. H. Guo, and Y. Gu, Polymer, 46, 11949 (2005).
Y. H. Kim, H. S. Kim, and S. K. Kwon, Macromolecules, 38, 7950 (2005).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Zeng, K., Guo, Q., Gao, S. et al. Studies on organosoluble polyimides based on a series of new asymmetric and symmetric dianhydrides: Structure/solubility and thermal property relationships. Macromol. Res. 20, 10–20 (2012). https://doi.org/10.1007/s13233-012-0007-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13233-012-0007-4