Abstract
The conditions for the Knoevenagel synthesis of 2-cyanoacrylates containing double and triple bonds in the alkoxycarbonyl group have been studied. It was found that the esters are formed in 10–70 % yields by the condensation of the respective cyanoacetates with formaldehyde in the 1∶1 ratio in the presence of piperidine, followed by the pyrolysis of the oligomers formedin vacuo at 170–200 °C in the presence ofpara-toluenesulfonic acid. The compounds synthesized readily undergo polymerization at room temperature and can be used as the basis for thermostable rapidly polymerizing adhesives.
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References
L. M. Pritykin, D. A. Kardashov, and V. L. Vakula,Monomernye klei [Monomeric Glues], Khimiya, Moscow, 1988, 78 (in Russian).
Lee Henry,Cyanoacrylate resins. The Instant adhesives.A Moznograph of their application and technology, Pasadena Technology Press, Los Angeles, California, 1986, 241.
V. S. Etlis, N. N. Trofimov, L. M. Degtyareva, A. B. Davydov, and A. Ya. Yakimova,Zh. Prikl. Khim., 1972, 222 [J. Appl. Chem. USSR, 1972 (Engl. Transl.)].
USSR Pat. Appl. 696013,Byull. izobret., 1979, No. 41, 96 (in Russian).
L. A. Yanovskaya, S. S. Yufit, and V. F. Kucherov,Khimiya atsetalei [The Chemistry of Acetals], Nauka, Moscow, 1975, 53 (in Russian).
M. Pawlowa, C. Konstantinow, P. Nowakow, and W. Kabaiwanow,Plaste und Kautschuk, 1982,29, 452.
E. Nishi,J. Adges. Soc. Japan, 1972,8, 89.
T. A. Protsailo, R. G. Makitra, and I. D. Polyanskii,Reaktsionnaya sposobnost' organicheskikh soedinenii [Reactivity of Organic Compounds], 1978,15, 598-02 1, 79 (in Russian).
T. I. Guseva, Yu. P. Kvachev, K. A. Mager, G. L. Slonimskii, and Yu. G. Gololobov,Sb. doki II Vsesoyuz. nauchno-tekhnicheskoi konf. “Adgezionnye soedineniya v mashinostroenii” [2nd All-Union Scientific and Technical Conference “Adhesive Compounds in Mechanical Engineering], RPI, Riga, 1989, 150 (in Russian).
T. I. Guseva, N. G. Senchenya, K. A. Mager, and Yu. G. Gololobov,Plastich, massy [Plastics], 1991, 11 (in Russian).
USSR Pat. Appl. 1502578,Byull. izobret., 1989, No. 31, 136.
T. I. Guseva, N. G. Senchenya, I. R. Gol'ding, K. A. Mager, and Yu. G. Gololobov,Izv. Akad. Nauk, Ser. Khim., 1993, 523 [Russ. Chem. Bull, 1993,42, 478 (Engl. Transl.)].
Formaldehyde, Ed. J. Frederic Walker, American Chemical Society Monograph Series, New-York, 1953.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 646–649, April, 1994.
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Guseva, T.I., Senchenya, N.G., Mager, K.A. et al. Synthesis of functionally substituted 2-cyanoacrylates. Russ Chem Bull 43, 595–598 (1994). https://doi.org/10.1007/BF00699831
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DOI: https://doi.org/10.1007/BF00699831