Abstract
A chemoselective synthesis of poly(o-hydroxy-amide) as a polybenzoxazole precursor has been developed. The polycondensation was carried out by addition of isophthaloyl dichloride to a solution of 3,3′-dihydroxybenzidine and lithium chloride in N-methylpyrrolidinone and gave the selective N-acylated polymer, poly(o-hydroxy-amide) with an inherent viscosity of 0.7 dLg−1. The structure of the polymer was characterized by IR, 1H, and 13C NMR spectroscopies. The model reaction was studied in detail to demonstrate the feasibility of the chemoselective polyamidation using benzoyl chloride and o-aminophenol.
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R. Rubner, H. Ahne, E. Kuhn, and G. Koloddieg, Photogr. Sci. Eng., 23, 303 (1979).
N. Yoda and H. Hiramoto, J. Macromol. Sci. Chem., A21, 1641 (1984).
T. Omote, “Polyimides,” M. K. Ghosh and K. L. Mittal, Ed., Marcel Dekker, Inc., New York, N.Y., 1996, p 121.
W. M. Moreau and K. N. Chiong, U.S. Patent 4,880,722(1989).
M. G. Moss, R. M. Cuzmar, and T. Brewer, SPIE adv. Resist Technol. Process VI, 1086, 396 (1989).
R. Hayase, K. Takano, Y. Mikogami, and Y. Nakano, J. Electrochem. Sci., 138, 3625 (1991).
R. Hayase, N. Kihara, N, Oyasato, S. Mitake, and M. Oba, J. Appl. Polym. Sci., 51, 1971 (1994).
T. Omote, H. Mochizuki, K. Koseki, and T. Yamaoka, Macromolecules, 23, 4796 (1990).
D. N. Khanna and W. H. Muller, in “Regional Techn. Conf. on Photopolymers, Principle-Process and Materials,” Ellenvile, New York, N.Y., 30, 429 (1988).
M. Ueda, K. Seki, and Y. Imai, Macromolecules, 15, 17 (1982).
T. Kubota and R. Nakanishi, J. Polym. Sci., Polym. Lett., 2, 655 (1965).
M. Bergmann, R. Ulpts, and F. Camacho, Ber., 55B, 2796 (1922).
M. Ueda, T. Morosumi, M. Kakuta, and R. Sato, Polym. J., 22, 733 (1990).
B. Morgenstern and H.-W. Kammer, Trends Polym. Sci., 4, 87 (1996).
C. L. McCormick, P. A. Callais, and B. H. Hutchinson Jr, Macromolecules, 18, 2394 (1985).
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Seino, H., Iguchi, K., Haba, O. et al. Chemoselective Polyamidation of 3,3′-Dihydroxybenzidine. Polym J 31, 822–827 (1999). https://doi.org/10.1295/polymj.31.822
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DOI: https://doi.org/10.1295/polymj.31.822