Abstract
Four new phenylated aromatic diamines, 1,4-bis(4-amino-3,5-diphenylphenyl)benzene (1a), 1,3-bis(4-amino-3,5-diphenylphenyl)benzene (1b), 1,4-bis(4-aminophenyl)-2,3,5-triphenylbenzene (2a), and 1,4-bis(4-aminophenyl)-2,3,5,6-tetraphenylbenzene (2b) were synthesized and polymerized with terephthaloyl chloride (TPC) and isophthaloyl chloride (IPC). All the polyamides showed high thermal stability with 5% weight-loss temperatures in the range of 466–524°C in air or nitrogen, and no melting peak below their decomposition temperatures. The polymers containing m-catenation had glass transition temperatures in the range of 275–349°C, and were soluble in N-methyl-2-pyrrolidone (NMP). The rigid rod-like polyamides consisting all para-oriented linkages showed no clear glass transition. In the rod-like polymers, polymer 2a/TPC showed good solubility in NMP, and preliminary optical microscope observation for the 20% solution showed an anisotropic property.
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M. Kakimoto, M. Yoneyama, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 26, 149 (1988).
S. S. Mohite, N. N. Maldar, and C. S. Marvel, J. Polym. Sci., Polym. Chem. Ed., 26, 2777 (1988).
F. Akutsu, K. Matsuo, K. Naruchi, and M. Miura, Polym. Commun., 30, 182 (1989).
Y. Oishi, S. Harada, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 27, 3393 (1989).
A. E. Lozano, J. G. de la Campa, and J. de Abajo, Makromol. Chem., Rapid Commun., 11, 471 (1990).
Y. Oishi, H. Takado, M. Yoneyama, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 28, 1763 (1990).
J. Lin, Y. Yuki, H. Kunisada, and S. Kondo, J. Appl. Polym. Sci., 40, 2113 (1990).
M. Xie, Y. Oishi, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 55 (1991).
H. Jeong, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 767 (1991).
G. Liou, Y. Oishi, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 995 (1991).
J. Y. Jadhav, W. R. Krigbaum, and J. Preston, Macromolecules, 21, 538 (1988).
J. Y. Jadhav and W. R. Krigbaum, J. Polym. Sci., Polym. Chem. Ed., 27, 1175 (1989).
W. Hatke, H. Schmidt, and W. Heitz, J. Polym. Sci., Polym. Chem. Ed., 29, 1387 (1991).
W. Hatke, H. Land, H. Schmidt, and W. Heitz, Makromol. Chem., Rapid Commun., 12, 235 (1991).
F. W. Harris and Y. Sakaguchi, Proc. Polym. Mater. Sci. Eng., 60, 187 (1989).
S. V. Krivun and G. N. Dorofeenko, Khim. Getero. Soedi., 2, 656 (1966).
W. Foerst, “Newer Method of Preparative Organic Chemistry,” Vol. III, Academic Press, New York, 1964, p 415.
H. Saikachi and Y. Taniguchi, Yakugaku Zasshi, 88, 1054 (1968).
E. C. Horning, Ed., “Org. Synth.,” Coll. Vol. 3, John Wiley & Sons, New York, 1955, p 806.
L. F. Fieser, “Organic Experiments,” 2nd ed, Heath, D. C., Co., Lexington, MA, 1968, p 297.
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Sakaguchi, Y., Harris, F. Synthesis and Characterization of Aromatic Polyamides Derived from New Phenylated Aromatic Diamines. Polym J 24, 1147–1154 (1992). https://doi.org/10.1295/polymj.24.1147
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DOI: https://doi.org/10.1295/polymj.24.1147
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