Abstract
A kinetic study on enaryloxynitriles via nucleophilic vinylic substitution reactions of various phenol derivatives with 1-chloro-1-phenyl-2,2-dicyanoethene was conducted in the presence of 1,4-diazabicyclo[2,2,2]octane (DABCO). The reaction was applied to solution polymerization of diphenol and diamine derivatives with p-bis(1-chloro-2,2-dicyanovinyl)benzene, which gave various poly(enamino-enaryloxynitriles) with moderate molecular weights in good yields. Thermal properties such as thermal curing and thermal stability were examined by differential scanning calorimetry and thermogravimetric analysis. The poly(enamino-enaryloxynitriles) showed similar curing to typical polyenaminonitriles and polyenaryloxynitriles.
Similar content being viewed by others
Article PDF
References
L. Pauling, J. Am. Chem. Soc., 54, 3570 (1932).
K. Friedrich, Angew. Chem. Int. Ed., 6, 959 (1967).
K. Wallenfels, K. Friedrich, J. Rieser, W. Ertel, and H. K. Thieme, Angew. Chem. Int. Ed., 15, 261 (1976).
Z. Rappoport and B. Avramovitch, J. Org. Chem., 47, 1397 (1982).
Z. Rappoport and A. J. Topol, J. Chem. Soc., Perkin Trans. 2, 863 (1975).
Z. Rappoport and R. Ta-shma, J. Chem. Soc. Sect. B, 1461 (1971).
Z. Rappoport and R. Ta-shma, J. Chem. Soc. Sect. B, 871 (1971).
Z. Rappoport and A. J. Topol, J. Chem. Soc., Perkin Trans. 2, 1823 (1972).
A. D. Josey, C. L. Dickinson, K. C. Dewhirst, and B. C. Mckusick, J. Org. Chem., 32, 1941 (1967).
C. L. Dickinson, D. W. Wiely, and B. C. Mckusick, J. Am. Chem. Soc., 82, 6132 (1967).
M. S. Gong and H. K. Hall, Macromolecules, 20, 1464 (1987).
D. R. Robello and J. A. Moore, Macromolecules, 22, 1094 (1989).
M. S. Gong, S. T. Kim, and H. S. Moon, Makromol, Chem. Rapid Commun., 12, 591 (1991).
H. G. Cho, S. H. Choi, and M. S. Gong, Macromolecules, 26, 6654 (1993).
H. S. Moon, J. S. Kim, C. B. Kim, and M. S. Gong, Polym. J., 25, 193 (1993).
J. C. Shin, T. M. Kim, and M. S. Gong, Macromolecules, 28, 2212 (1995).
J. H. Ha, C. Kim, and M. S. Gong, Polym. J., 27, 536 (1995).
S. H. Moon, S. G. Kim, T. M. Kim, and M. S. Gong, Bull. Korean Chem. Soc., 15, 901 (1994).
S. G. Kim, Y. K. Han, and M. S. Gong, Bull. Korean Chem. Soc., 16, 326 (1995).
N. Kim and M. S. Gong, Bull. Korean Chem. Soc., 21, 1111 (2000).
A. C. Griffin and S. J. Havens, J. Polym. Sci., Part B: Polym. Phys. Ed., 19, 951 (1981).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Noh, AS., Geum, NR. & Gong, MS. New Method for Preparation of Poly(enamino-enaryloxynitriles) and Thermal Properties. Polym J 33, 150–155 (2001). https://doi.org/10.1295/polymj.33.150
Issue Date:
DOI: https://doi.org/10.1295/polymj.33.150
Keywords
This article is cited by
-
Preparation of polyesteramides based on aliphatic amine-containing phenol derivatives via interfacial polymerization
Macromolecular Research (2003)