Abstract
A polyimide from 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA) and 2,4,6-trimethyl-1,3-phenylenediamine (TrMPD), which has less efficient packing of polymer chains and displays very high gas permeability, was methyl-brominated and then phosphorylated by the reaction of -CH2Br with triethyl phosphite. The degree of phosphorylation upto 200% (two phosphonate ester groups per repeating unit) was achieved. Phosphorylation increased the sorption amount of benzene but decreased that of cyclohexane. Phosphorylated polyimide membranes were crosslinked thermally and/or with diamine. The amine-crosslinked membranes with P content of 5.9–8.3 wt% have high performance of pervaporation of benzene-cyclohexane mixtures; for example, specific permeation flux of 10 kg μm m−2 h−1 and separation factor of 15 at 343 K and benzene composition in feed of 50 wt%.
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I. Cabasso, Ind. Eng. Chem. Prod. Res. Dev., 22, 313 (1983).
H. R. Acharya, S. A. Stern, Z. Z. Liu, and I. Cabasso, J. Membr. Sci., 37, 205 (1988).
J. Terada, T. Hohjoh, S. Yoshimasu, M. Ikemi, T. Okano, and I. Shinihara, Polym. J., 14, 347 (1982).
T. Yamaguchi, S. Nakao, and S. Kimura, Macromolecules, 24, 5522 (1991).
T. Yamaguchi, S. Nakao, and S. Kimura, Ind. Eng. Chem. Res., 31, 1914 (1992).
L. Enneking, W. Stephan, and A. Heintz, Ber. Bunsenges. Phys. Chem., 97, 912 (1993).
N. Tanihara, K. Tanaka, H. Kita, and K. Okamoto, J. Membr. Sci., 95, 161 (1994).
H. Ohst, K. Hildebrand, and R. Dhein, Proceedings of 5th International Conference Pervaporation Processes, Chem. Ind., Bakish Mat. Corp., Engelwood, NJ, 1991, p 7.
N. Tanihara, N. Umeo, T. Kawabata, K. Tanaka, H. Kita, and K. Okamoto, J. Membr. Sci., 104, 181 (1995).
J. Hao, K. Tanaka, H, Kita, and K. Okamoto, J. Membr. Sci., 132, 97 (1997).
Y. Kusuki, Maku (Membrane), 21, 276 (1996).
K. Nakagawa, Y. Asakura, S. Nakanishi, H. Hoshino, H. Kouda, and Y. Kusuki, Kobunshi Ronbunshu, 46, 405 (1989).
I. Cabasso and J. Jagur-Grodzinski, J. Appl. Polym. Sci., 18, 1969 (1974).
I. Cabasso and C. N. Tran, J. Appl. Polym. Sci., 23, 2967 (1979).
Y. Hirayama, T. Yoshinaga, Y. Kusuki, K. Ninimiya, T. Sakakibara, and T. Tamari, J. Membr. Sci., 111, 183 (1996).
D. W. Van Krevelen, “Properties of Polymers,” Elsevier, Amsterdam, 1976, p 129.
I. Cabasso, J. J.-Grodzinski, and D. Vofsi, J. Appl. Polym. Sci., 18, 2137 (1974).
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Okamoto, Ki., Ijyuin, T., Fujiwara, S. et al. Synthesis and Characterization of Polyimides with Pendant Phosphonate Ester Groups. Polym J 30, 492–498 (1998). https://doi.org/10.1295/polymj.30.492
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DOI: https://doi.org/10.1295/polymj.30.492