Abstract
Phenyl, 2-naphthyl(2-Np-MA), 1-naphthyl(1-Np-MA), 9-fluorenyl, 5,6,7, 8-tetrahydro-1-naphthyl, cyclohexyl(CH-MA), cyclopentyl(CP-MA), and decahydro-2-naphthyl(D-MA) methacrylates were polymerized in bulk, benzene, and n-hexane by radical initiators. The polymers were converted into poly (methyl methacrylate)(PMMA) by hydrolysis followed by methylation. The tacticities of the polymers were studied by comparing the IR and NMR spectra of the derived PMMA’s. The polymers containing aromatic substituents were more isotactic than conventional PMMA, and especially poly(2-Np-MA) prepared in n-hexane and poly(1-Np-MA)’s were considerably isotactic. On the other hand, tacticities of poly(CH-MA)’s, poly(CP-MA)’s, and poly(D-MA)’s were nearly the same as those of conventional PMMA. These results suggest that aromatic rings of the methacrylates seem to promote the formation of isotactic sequence and this effect is enhanced with naphthyl groups, but the aliphatic rings have little effect on such stereoregulation.
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H. Watanabe, Kogyo Kagaku Zasshi (J. Chem. Soc. Japan, Ind. Chem. Sect.), 64, 1851 (1961).
H. Watanabe, Y. Kato, and A. Nishioka, Kogyo Kagaku Zasshi, 65, 273 (1962).
T. G. Fox and H. W. Scheneko, Polymer, 3, 575 (1962).
I. Sakurada, Y. Sakaguchi, and G. Ohara, Kobunshi Kagaku (Chem. High Polymers, Japan), 19, 704 (1962).
I. Sakurada, Y. Sakaguchi, J. Nishino, and T. Iwagaki, Kobunshi Kagaku, 20, 456 (1963).
G. Schroder, Makromol. Chem., 97, 232 (1966).
A. Yamada, M. Yanagita, S. Arano, and H. Sekimura, Kogyo Kagaku Zasshi (J. Chem. Soc. Japan, Ind. Chem. Sect.), 73, 2352 (1970).
K. Matsuzaki, A. Ishida, N. Tateno, T. Asakura, A. Hasegawa, and M. Tameda, Kogyo Kagaku Zasshi (J. Chem. Soc. Japan, Ind. Chem. Sect.), 68, 852 (1965).
K. Yokota and Y. Ishii, J. Polym. Sci., Part B, 3, 771 (1965).
K. Yokota and Y. Ishii, Kogyo Kagaku Zasshi (J. Chem. Soc. Japan, Ind. Chem. Sect.), 69, 1053 (1966).
K. J. Liu, J. S. Lignowski, and R. Ulman, Makromol. Chem., 105, 8 (1967).
H. Imai, T. Makimoto, and T. Tsuruta, Kogyo Kagaku Zasshi (J. Chem. Soc. Japan, Ind. Chem. Sect.), 68, 1947 (1965).
H. Yuki, K. Hatada, T. Ninomi, and Y. Kikuchi, Polym. J., 1, 36 (1970).
H. Yuki, K. Hatada, Y. Kikuchi, and T. Ninomi, J. Polym. Sci., Part B, 6, 753 (1968).
S. Patai, M. Bentor, and M. E. Reichmann, J. Am. Chem. Soc., 74, 845 (1952).
E. M. Filachione, J. H. Lengel, and W. P. Ratchford, J. Am. Chem. Soc., 72, 840 (1950).
“Yuki Kagobutsu Gosei-ho”, Vol. 11, Yuki Gosei Kagaku Kyokai Ed., Giho-do, Tokyo, 1968, pp 18 and 93.
C. E. Rehberg and W. A. Faucette, J. Am. Chem. Soc., 72, 4307 (1950).
J. Lai and R. Green, J. Org. Chem., 20, 397 (1955).
A. Weissberger and E. S. Proskauer, “Organic Solvents” 2nd ed, Interscience Publishers Inc., New York N.Y., 1955.
“Organic Syntheses,” Collective, Vol. 2, J. Wiley Publishers, New York, N.Y., 1943, pp 165 and 461.
A. Katchalsky and H. Eisenberg, J. Polym. Sci., 6, 145 (1951).
F. A. Bovey and G. V. D. Tiers, J. Polym. Sci., 44, 173 (1960).
U. Baumann, H. Schreiber, and K. Tessmar, Makromol. Chem., 36, 81 (1960).
J. Furukawa, T. Tsuruta, S. Nakayama, A. Kawasaki, and G. Wasai, Kogyo Kagaku Zasshi (J. Chem. Soc., Japan, Chem. Ind. Sect.), 64, 591 (1961).
M. Szwarc, Chem. Ind. (London), 1589 (1958).
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Nishino, J., Nakahata, H. & Sakaguchi, Y. Stereoregularities of Ring-containing Polymethacrylates Obtained by Radical Polymerization. Polym J 2, 555–559 (1971). https://doi.org/10.1295/polymj.2.555
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DOI: https://doi.org/10.1295/polymj.2.555
Keywords
- Stereoregularity
- Radical Polymerization
- Poly(phenyl methacrylate)
- Poly(2-naphthyl methacrylate)
- Poly(1-naphthyl methacrylate)
- Poly(5, 6, 7, 8-tetrahydro-1-naphthyl methacrylate)
- Poly(cyclohexyl methacrylate)
- Poly (cyclopenthyl methacrylate)
- Poly(decahydro-2-naphthyl methacrylate)
- Poly(methyl methacrylate)
- IR
- NMR