Abstract
p-Fluoromethylstyrene (p-FMS) was prepared by means of a halogen—halogen interconversion reaction of p-chloromethylstyrene with potassium fluoride in the presence of a phase-transfer catalyst. As p-FMS is increasingly purified, it becomes less stable and undergoes the polycondensation of benzylic-type fluoromethyl groups. However, p-FMS was stable when traces of a basic solvent were added to it. Thus, in the presence of a small amount of acetonitrile, the homopolymerization of the monomer and the copolymerization with styrene (St) were carried out at 60°C using α,α′-azobisisobutyronitrile as an initiator. The radical copolymerization of p-FMS with methyl methacrylate (MMA) takes place without any polycondensation even in the absence of a basic solvent, owing to the weak basicity of MMA itself. Monomer reactivity ratios of p-FMS (MA) with St and MMA (MB) are rA=1.3, rB=0.44 and rA=0.84, rB=0.30, respectively. The polymers obtained were found to be stable both in solid state and in basic solvents.
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J. Brandrup and E. H. Immergut, “Polymer Handbook” 2nd Edition, John Wiley & Sons, New York, N.Y., 1975, p II-344.
R. Asami, M. Gyi, M. Takaki, and K. Shinohara, to be published.
D. Landini, F. Montanari, and F. Rolla, Synthesis, 428 (1974).
C. M. Starks, J. Am. Chem. Soc., 93, 195 (1971).
J. Dockx, Synthesis, 441 (1973).
J. Bernstein, J. S. Roth, and W. T. Miller, J. Am. Chem. Soc., 70, 2310 (1948).
M. Takaki, R. Asami, and S. Kawakami, Polym. Prepr., Jpn., 26, No. 1, 176 (1977).
J. Brandrup and E. H. Immergut, “Polymer Handbook” 2nd Edition, John Wiley & Sons, New York, N.Y., 1975, p II-67.
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Asami, R., Gyi, M., Takaki, M. et al. Preparation and Polymerization of p-Fluoromethylstyrene. Polym J 10, 301–306 (1978). https://doi.org/10.1295/polymj.10.301
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DOI: https://doi.org/10.1295/polymj.10.301