Abstract
N,N-Diphenylacrylamide (DPAA) was polymerized with anionic and radical initiators in toluene and tetrahydrofuran. The tacticity of the obtained polymers (poly(DPAA)) was unable to be determined directly by NMR spectroscopy. Therefore, poly(DPAA) was carefully converted to poly(acrylic acid) by solvolysis in a mixture of concentrated sulfuric acid and methanol (60:40; by volume) at 90°C for 24 hours, followed by methylation with diazomethane. Under suitable conditions, the transformation was performed without change (racemization) of tacticity of the polymers. Diad tacticity of the derived poly(methyl acrylate) was determined by 1H NMR spectroscopy. Anionic polymerization using butyllithium in toluene afforded a polymer rich in meso diad (m=0.95), and that in tetrahydrofuran racemo diad (r=0.66). Radical polymerization in toluene afforded a polymer with the highest racemo diad content (r=0.85).
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
D. V. Badami, Polymer, 1, 273 (1960).
K. Butler, P. R. Thomas, and G. J. Tyler, J. Polym. Sci., 48, 357 (1960).
Y. Okamoto, M. Adachi, H. Shohi, and Y. Yuki, Polym. J., 13, 175 (1981).
Y. Okamoto, H. Hayashida, and K. Hatada, Polym. J., 21, 543 (1989).
Huynh-Ba-Gia and J. E. McGrath, Polym. Bull., 2, 837 (1980).
S. S. Huang and J. E. McGrath, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 24, 138 (1983).
X. Xie and T. Hogen-Esch, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 33, 241 (1992).
K. Kobayashi, T. Ishizone, A. Hirao, S. Nakahama, and M. Kobayashi, Polym. Prep., Jpn. (Engl. Ed.), 44, 563 (1995).
K. Matsuzaki, T. Uryu, A. Ishida, T. Ohki, and M. Takeuchi, J. Polym. Sci., A-1, 5, 2167 (1967).
T. J. Bessell and R. J. Young, J. Polym. Sci., Polym. Lett. Ed., 12, 635 (1974).
T. Nakano, Y. Okamoto, and K. Hatada, J. Am. Chem. Soc., 114, 1318 (1992).
N. A. Porter, T. R. Allen, and R. A. Breyer, J. Am. Chem. Soc., 114, 7676 (1992).
Poly(MA) was obtained by anionic polymerization of methyl acrylate (MA) using n-BuLi as an initiator in toluene at −78°C for 24 hours, [MA]/[BuLi]=20. Degree of polymerization=296; M w/M n=4.92.
H. Yuki and K. Hatada, Adv. Polym. Sci., 31, 1 (1979).
K. Matsuzaki, T. Uryu, T. Kanai, K. Hosonuma, T. Matsubara, H. Tachikawa, M. Yamada, and S. Okuzono, Makromol. Chem., 178, 11 (1977).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shiohara, K., Habaue, S. & Okamoto, Y. Stereospecific Polymerization of N,N-Diphenylacrylamide. Polym J 28, 682–685 (1996). https://doi.org/10.1295/polymj.28.682
Issue date:
DOI: https://doi.org/10.1295/polymj.28.682
Keywords
This article is cited by
-
Functional Acrylate Polymer Synthesis: Postpolymerization Modification Approach
Macromolecular Research (2022)
