Summary
Hydrosilylation of N-allylimidazole hydrochloride by methyldichlorosilane (MeCl2SiH) under mild conditions leads to a high yield of N-[γ-(methyldichlorosilyl)propyl]imidazole hydrochloride — highly reactive monomer for synthesis of imidazole modified polysiloxanes. This compound was used as the substrate for the generation of new cyclooligosiloxanes with the imidazole group attached through the trimethylene bridge to a siloxane ring. The anionic ring-opening polymerization of these cyclics permits the controlled synthesis of polysiloxanes with imidazole groups pendant to the polymer chain.
Similar content being viewed by others
References
Burger, B.; Kreuzer, F.H. in Silicon in Polymer Synthesis, Kricheldorf, H.R. ed. Springer, Heidelberg 1996, chapter 3, pp 131–137.
Zhou, G.B.; Khan, J.M.; Ishrat, M.; Smid, J. Macromolecules 1993, 26, 2202.
Duplock, S.K.; Matisons, J.G.; Swincer, A.G.; Warren, R.F.O. J. Inorg. and Organometal. Polym. 1991, 1, 361.
Rózga-Wijas, K.; Chojnowski, J.; Zundel, T.; Boileau, S. Macromolecules 1996, 29, 2711.
Crivello, J.V.; Yang, B.; Kim, W.G. J. Polym. Sci. Part A 1995, 33, 2415.
Yu, J.M.; Teyssié, D.; Boileau, S. J.Polym. Sci. Part A, Polym. Chem. 1993, 31, 2373.
Yamada, Y.; Li, Y.; Nakaya, T. Macromolecules 1995, 28, 2590.
Hsiue, G.H.; Chen, Jr-H. Macromolecules 1995, 28, 4366.
Rubinsztajn, S.; Zeldin, M.; Fife, W.K. Macromolecules 1991, 24, 2682.
Rubinsztajn, S.; Zeldin, M.; Fife, W.K. Macromolecules 1990, 23, 4026.
Fife, W.K.; Zeldin, M.; Tian, Ch-X. in Advances in Chemistry series 224, Silicon-Based Polymer Science, ed. Ziegler, J.M.; Fearon, F.W.G., Am. Chem. Soc. Washington DC, 1990, p. 99.
Nemoto, N.; Yotsuya, T.; Aoyagj, S.; Ikeda, K.; Takamiya, N. Polymer Commun. 1990, 31, 65.
Rubinsztajn, S.; Cypryk, M.; Chojnowski, J. J. Organomet. Chem. 1989, 367, 27.
Nemoto, N.; Aizawa, M.; Ueno, Y.; Ikeda, K.; Takamiya, N. Polym. Bull, 1992, 27, 413.
Nemoto, N.; Ishii, H.; Ihara, M.; Ikeda, K.; Takamiya, N. J. Polym. Sci Part A, Polymer Chem. 1994, 32, 2457.
Koyama, N.; Ueno, Y.; Sekiyama, Y.; Ikeda, K.; Sekine, Y. Polymer, 1986, 27, 293.
Nemoto, N.; Ishii, H.; Ueno, Y.; Ikeda, K.; Takamiya, N. Makromol. Chem. 1992, 193, 59.
Nagai, K.; Ueno, Y.; Takiyama, N. Macromol. Chem. Phys. 1995, 196, 1241.
Mazurek, M.; North, A.M.; Pethrick, R.A. Polymer, 1980, 21, 369.
Pouliquen, L.; Coqueret, X.; Morlet-Savary, F.; Fouassier, J.P. Macromolecules 1995, 28, 8028.
Yang, C.Y.; Wnek, G.E. Polymer, 1992, 33, 4191.
Pham-van-cang, C.; Winnik, M.A.; Dorigo, R.; Boileau, S. Europ. Polym. J. 1995, 31, 227.
Chujo, Y.; Mc Grath, J.E. J. Macromol. Sci., J. M. S. Pure Appl. Chem. 1995, A 32, 29.
Abd Majid, W.H.; Richardson, T.; Holder, S.; Lacey, D. Thin Solid Films 1994, 243, 378.
Spinu, M.; Mc Grath, J.E. J. Polym. Sci. Part A, Polym. Chem. 1991, 29, 657.
Zeldin, M.; Granger, E.; Fife, W.K. J. Inorg. Organometal. Polym. 1993, 3, 141.
Lyashenko, G.S.; Nametkin, N.S.; Chernysheva, T.I. Izv. Acad. Nauk SSSR ser. Khim 1969, 2628.
Nametkin, N.S.; Kobrakov, K.I.; Kuzmin, O.V.; Sorokin, G.V. Vysokomol. Soedin Ser. B, 1970, 12, 425.
Bachrach, A.; Zielkha, A. Europ. Polym. J. 1984, 20, 493.
Fortuniak, W. unpublished results.
Torrès, G.; Madec, P. J.; Marechal, E. Makromol. Chem. 1989, 190, 203.
Majoras, I.; Marsalko, T.M.; Kennedy, J.P. J. Polym. Sci. Part A, Polym. Chem. 1996, 34, 1675.
Kaźmierski, K; Chojnowski, J. in preparation.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Fortuniak, W., Chojnowski, J. A route to polysiloxanes with pendant imidazole groups. Polymer Bulletin 38, 371–378 (1997). https://doi.org/10.1007/s002890050062
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s002890050062