Abstract
We report the preparation of a new novolac having formyl groups by the addition-condensation of 2,4,6-trimethoxy-benzaldehyde (1) and 1,3,5-trimethoxybenzene (2) with formaldehyde. In the case of the polymerization of 1 and formaldehyde, polymerization did not occur; however, the polymerization of 1, 2 and formaldehyde proceeded to give polymer 3 (Mn 4200, Mw/Mn 1.2). The FT-IR, 1H NMR and 13C NMR spectra of 3 showed that it had phenylene-methylene units on the polymer backbone and the formyl groups of 1 remained without side reactions. To evaluate its ability as a reactive polymer, the imination of 3 with 1,5-diaminopentane was carried out to obtain an organo-insoluble gel (5), which had the network structure of 3 and a pentamethylene unit via the imine moiety. The temperature at 5% loss in weight (Td5, 335 °C) of 5 slightly decreased compared to that of 3 (351 °C). This result indicates that polymer 3 can be utilized as a reactive polymer, and form a thermostable gel via the imine moiety.
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References
A. Knop and L. A. Pilato, “Phenolic Resins,” Springer-verlag, Berlin, 1985.
G. Konishi, J. Syn. Org. Chem. Jpn., 66, 705 (2008).
T. Takeichi, T. Kawauchi, and T. Agag, Polym. J., 40, 1121 (2008).
J. Cui, Y. Yan, J. Liu, and Q. Wu, Polym. J., 40, 1067 (2008).
B. S. Kaith and S. Kalia, Polym. J., 39, 1319 (2007).
G. Pan, Z. Du, C. Zhang, C. Li, X. Yang, and H. Li, Polym. J., 39, 478 (2007).
K. Suzuki, H. Matsumoto, M. Minagawa, M. Kimura, and A. Tanioka, Polym. J., 39, 1128 (2007).
T. Nemoto, I. Amir, and G. Konishi, Polym. J., 41, 338 (2009).
M. Ukaji, M. Takamura, K. Shirai, W. Gang, T. Yamauchi, and N. Tsubokawa, Polym. J., 40, 607 (2008).
F. Helfferich, “Ion Exchange,” NewYork, McGraw Hill, 1962.
J. Kadota, T. Fukuoka, H. Uyama, K. Hasegawa, and S. Kobayashi, Macromol. Rapid Commun., 25, 441 (2004).
H. C. Y. Koh, J. Dai, E. Tan, and W. Liang, J. Appl. Polym. Sci., 101, 1775 (2006).
B. A. Adams and E. L. Holmes, J. Soc. Chem. Ind., 54, 1 (1935).
J. M. J. Fréchet, G. D. Darling, S. Itsuno, P. Z. Lu, M. V. de Meftahi, and W. A. Rolls, Pure Appl. Chem., 60, 353 (1988).
N. N. Ghosh, B. Kiskan, and Y. Yagci, Prog. Polym. Sci., 32, 1344 (2007).
H. Ritter and R. Sperber, Macromolecules, 27, 5919 (1994).
T. F. Scott, A. D. Schneider, W. D. Cook, and C. N. Bowman, Science, 308, 1615 (2005).
M. A. Tasdelen, V. Kumbaraci, N. Talinli, and Y. Yagci, Macromolecules, 40, 4406 (2007).
S. Sugawara, M. Tomoi, and T. Oyama, Polym. J., 39, 129 (2007).
K. Tsuchiya, Y. Shibasaki, and M. Ueda, Polym. J., 39, 442 (2007).
T. Nishikubo, H. Kudo, and H. Nomura, Polym. J., 40, 310 (2008).
K. Mizoguchi and M. Ueda, Polym. J., 40, 645 (2008).
N. Matsumi and Y. Chujo, Polym. J., 40, 77 (2008).
R. B. Merrifield, J. Am. Chem. Soc., 85, 2149 (1963).
P. Hodge, Chem. Soc. Rev., 26, 417 (1997).
B. Yan and H. C. Gremlich, J. Chromatogr., B: Biomed. Sci. Appl., 725, 91 (1999).
V. Strehmel, B. Strehmel, F. Karl, G. Muller, and M. Fedtke, Angew. Makromol. Chem., 200, 125 (1992).
D.-M. Shin, N. Ozeki, Y. Nakamoto, and G. Konishi, Macromol. Res., 14, 255 (2006).
T. Kimura, Y. Nakamoto, and G. Konishi, Polym. J., 38, 606 (2006).
T. Nemoto, T. Ueno, M. Nishi, D.-M. Shin, Y. Nakamoto, and G. Konishi, Polym. J., 38, 1278 (2006).
J. Jeerupan, G. Konishi, T. Nemoto, D. M. Shin, and Y. Nakamoto, Polym. J., 39, 762 (2007).
A. Kobayashi and G. Konishi, Polym. J., 40, 590 (2008).
T. Nemoto and G. Konishi, Polym. J., 40, 651 (2008).
T. Nemoto, G. Konishi, T. Arai, and T. Takata, Polym. J., 40, 622 (2008).
N. Sreenivasachary and J. M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 102, 5938 (2005).
T. Takata and H. Otsuka, J. Syn. Org. Chem. Jpn., 64, 194 (2006).
L. Piazzi, F. Belluti, A. Bisi, S. Gobbi, S. Rizzo, M. Bartolini, V. Andrisano, M. Recanatini, and A. Rampa, Bioorg. Med. Chem., 15, 575 (2007).
Y. Chujo, K. Sada, and T. Saegusa, Macromolecules, 23, 2636 (1990).
Y. Chujo, K. Sada, and T. Saegusa, Macromolecules, 26, 6315 (1993).
Y. Chujo, K. Sada, and T. Saegusa, Macromolecules, 26, 6320 (1993).
P. Cordier, F. Tournilhac, C. Soulie-Ziakovic, and L. Leibler, Nature (London), 451, 977 (2008).
T. Nemoto, I. Amir, and G. Konishi, Polym. J., 41, 395 (2009).
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Nemoto, T., Amir, I. & Konishi, Gi. Synthesis of a Formyl Group-Containing Reactive Novolac. Polym J 41, 389–394 (2009). https://doi.org/10.1295/polymj.PJ2008316
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DOI: https://doi.org/10.1295/polymj.PJ2008316
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