Abstract
New amidine-containing polymers were prepared by the polycondensation of aromatic diamines with bis(imidoyl) chlorides in polar organic solvents in the presence of various catalysts (triethylamine, tributylamine, and pyridine N-oxide). Optimal synthesis conditions, namely, temperature, duration, concentration of monomers and catalyst, and the order of reagent loading, were established. The structure of polyamidines was studied by elemental analysis and IR and NMR spectroscopy. When the polymers were heated to 250°C in vacuum, their molecular masses increased.
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References
J. W. McFarland and H. L. Howes, J. Med. Chem. 13, 109 (1970).
E. A. Glazer, US Patent No. 4,546,113 (1985).
J. N. Ashley, H. J. Barber, A. J. Ewins, et al., J. Chem. Soc. 29, 103 (1942).
R. G. Glushkov, G. A. Modnikova, A. I. L’vov, et al., Khim.-Farm. Zh. 38(8), 16 (2004).
D. J. Speelman and A. J. Virant, US Patent No. 4,839,405 (1989).
V. B. Piskov and V. P. Kasperovich, Zh. Org. Khim. 14, 820 (1978).
D. Walter, R. Fischer, H. Gorls, et al., J. Organomet. Chem. 508, 13 (1996).
D. Abeysekera, K. N. Robertson, T. S. Cameron, and J. A. C. Clyburne, Organometallics 20, 5532 (2001).
F. Böhme, C. Kunert, C. Klinger, and H. Komber, Macromol. Symp., No. 128, 183 (1998).
F. Böhme, C. Klinger, H. Komber, et al., J. Polym. Sci., Part A: Polym. Chem. 36, 932 (1998).
G. S. Gol’din, M. V. Maksakova, and E. P. Volgina, USSR Inventor’s Certificate No. 297 657 (1971).
C. Grundmann and A. Kreutzberger, J. Polym. Sci. 38, 425 (1959).
K. Kurita, Y. Kusayama, and Y. Iwakura, J. Polym. Sci., Part A-1 15, 2163 (1977).
S. Ogata, M. Kakimoto, and Y. Imai, Makromol. Chem., Rapid Commun. 6, 835 (1985).
C. Gerhardt, Annales 108, 214 (1858).
L. M. Litvinenko and G. D. Titskii, Dokl. Akad. Nauk SSSR 177, 127 (1967).
Yu. V. Tonevitskii, D. M. Mognonov, D. B. Sanzhizhapov, et al., Izv. Ross. Akad. Nauk, Ser. Khim., No. 3, 626 (1999).
A. Bernethsen, Annales 184, 353 (1877).
V. M. Savinov and L. B. Sokolov, Vysokomol. Soedin. 7, 772 (1965).
J. Sevcik and F. Grambal, in The Chemistry of Amidines and Imidates, Ed. by S. Patai (Wiley, New York, 1975), p. 603.
O. Bayer, Angew. Chem. 61, 236 (1949).
Ch. Reichardt, Solvents and Solvent Effect in Organic Chemistry (VCH, Weinheim, 1988; Mir, Moscow, 1991).
A. Weissberger, E. Proskauer, J. Riddick, and E. Toops, Organic Solvents. Physical Properties and Methods of Purification (Wiley, New York, 1955; Inostrannaya Literatura, Moscow, 1958).
Ya. S. Vygodskii, Doctoral Dissertation in Chemistry (Moscow, 1980).
E. Ochiai, J. Org. Chem. 18, 534 (1953).
P. W. Morgan, Condensation Polymers: By Interfacial and Solution Methods (Wiley, New York, 1965; Khimiya, Moscow, 1970).
Houben-Weyl, Methoden der organischen Chemie (Georg Thieme, Stuttgart, 1953; Khimiya, Moscow, 1967), Vol. 2.
Yu. P. Kitaev and B. I. Buzykin, Hydrazones (Nauka, Moscow, 1974) [in Russian].
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Original Russian Text © A.V. Toktonov, D.M. Mognonov, Zh.P. Mazurevskaya, S.O. Botoeva, 2006, published in Vysokomolekulyarnye Soedineniya, Ser. A, 2006, Vol. 48, No. 1, pp. 5–15.
This work was supported by the special-purpose federal program “Integration” (state contract 109, direction 1.5/2001) and the Government of the Buryat Republic (direction “New Monomers and Chemical Products,” 2002).
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Toktonov, A.V., Mognonov, D.M., Mazurevskaya, Z.P. et al. Synthesis of polyamidines based on aromatic bis(imidoyl) chlorides in solution. Polym. Sci. Ser. A 48, 1–10 (2006). https://doi.org/10.1134/S0965545X06010019
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DOI: https://doi.org/10.1134/S0965545X06010019