Abstract
A new phenylated diamine, bis(4-amino-2-biphenyl)ether, was synthesized in five steps starting from 3-chloro-4-fluoronitrobenzene. New aromatic polyimides having phenyl groups at the 2- and 2′-positions of the diphenyl ether moiety were prepared from this diamine and various tetracarboxylic dianhydrides by the conventional two-step procedure that included ring-opening polymerization in NMP and subsequent thermal cyclic dehydration. The polyimides were characterized by differential scanning calorimetry (DSC), thermogravimetry, and dynamic mechanical analysis (DMA). Typical polyimides showed excellent thermal stability, and had glass transition temperature (Tg) above 250 °C. As for the series of polyimides prepared from tetracarboxylic anhydrides having linear phenylene moiety, the introduction of phenyl group at the 2- and 2′-positions of phenyl ether improved thermal and thermo-mechanical properties as well as the solubility of polymers.
Similar content being viewed by others
Article PDF
References
P. E. Cassidy, “Thermally Stable Polymer,” Marcel Dekker, New York, 1980, chapt. 4.
K. L. Mittal, “Polyimides: Synthesis, Characterization, and Applications,” Plenum Press, New York, 1984.
M. I. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Lauias, “Polyimides: Thermally Stable Polymer,” Consultants Bureau, A Division of Plenum Publishing Co., New York, 1987.
C. Feger, M. M. Khojasteh, and J. M. MacGrath, “Polyimides: Materials, Chemistry and Characterization,” Elsevier, Amsterdam, 1989.
M. I. Bessonov and V. A. Zubkov, “Polyamic acid and Polyimides: Synthesis and Transformation and Structure.” CRC Press, Boca Raton, FL, 1993.
C. Feger, M. M. Khojasteh, and S. E. Molis, “Polyimides: Trends in Materials and Applications,” Society of Plastic Engineers, Mid Hudson Section, New York, 1996.
M. K. Ghosh and K. L. Mittal, Polyimides: “Fundamentals and Applications,” Marcel Dekker, New York, N.Y., 1996.
P. M. Hergenrother, Polym. J., 19, 73 (1987).
I. Mita, Kinouzairyou, 1, 1 (1981).
M. Hasegawa, N. Sensui, Y. Shindo, and R. Yokota, Macromolecules, 32, 387 (1999).
St. A. K. Clair and St. T. L. Clair, Polym. Mater. Sci. Eng., 51, 62 (1984).
St. A. K. Clair, St. T. L. Clair, W. S. Slemp, and K. S. Ezzel, Proc. 2nd Int. Conf. on Polyimides, Elleville, NY, 333 (1985).
St. A. K. Clair and W. S. Slemp, SAMPE J., 21, 28 (1985).
St. A. K. Clair and St. T. L. Clair, Polym. Mater. Sci. Eng., 55, 396 (1986).
St. A. K. Clair, St. T. L. Clair, and W. P. Winfree, Polym. Mater. Sci. Eng., 55, 396 (1986).
A. Morikawa, Polym. J., 32, 275 (2000).
A. Morikawa and Y. Hosoya, Polym. J., 34, 544 (2002).
A. Morikawa and K. Ono, Polym. J., 32, 948 (2000).
A. Morikawa and K. Ono, High Perform. Polym., 13, S73 (2001).
T. Oh-e, N. Miyaura, and A. Suzuki, Synlett, 221 (1990).
M. Hasegawa, M. Kochi, I. Mita, and R. Yokota, Eur. Polym. J., 25, 349 (1989).
M. Hasegawa and K. Horie, Prog. Polym. Sci., 26, 259 (2001).
Y. Imai, N. N. Maldar, and M. Kakimoto, J. Polym. Sci., Polym. Chem. Ed., 22, 2189 (1984).
H.-J. Jeong, A. Kobayashi, M. Kakimoto, and Y. Imai, Polym. J., 26, 373 (1994).
H.-J. Jeong, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 39 (1991).
H.-J. Jeong, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 1691 (1991).
Y. Ohishi, M. Ishida, M. Kakimoto, Y. Imai, and T. Kurosaki, J. Polym. Sci., Polym. Chem. Ed., 30, 1027 (1992).
I. K. Spiliopoulos and J. A. Microyannidis, Macromolecules, 31, 1236 (1998).
I. K. Spiliopoulos and J. A. Microyannidis, Macromolecules, 31, 515 (1998).
A. Morikawa and T. Hatakeyama, Polym. J., 31, 66 (1999).
Y. Imai, High Perform. Polym., 7, 337 (1995).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Morikawa, A., Furukawa, Ta. & Moriyama, Y. Synthesis and Characterization of Novel Aromatic Polyimides from Bis(4-amino-2-biphenyl)ether and Aromatic Tetracarboxylic Dianhydrides. Polym J 37, 759–766 (2005). https://doi.org/10.1295/polymj.37.759
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.37.759
Keywords
This article is cited by
-
Synthesis and characterization of novel aromatic polyimides from Z-type sexiphenyltetracarboxylic dianhydride and aromatic diamines
Polymer Journal (2014)
-
Novel phenylethynyl-terminated PMDA-type polyimides based on KAPTON backbone structures derived from 2-phenyl-4,4′-diaminodiphenyl ether
Polymer Journal (2012)
-
Dynamic tensile properties of a novel Kapton-type asymmetric polyimide derived from 2-phenyl-4,4′-diaminodiphenyl ether
Polymer Journal (2011)