Synthesis and reactivity ratios of regioisomeric vinyl‐1,2,3‐triazoles with styrene |
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Authors: | Michael Lartey Martijn Gillissen Brian J Adzima Kenichi Takizawa David R Luebke Hunaid B Nulwala |
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Institution: | 1. National Energy Technology Laboratory, , Pennsylvania, 15129;2. Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, , MB Eindhoven, NL‐5600 The Netherlands;3. Mitsubishi Chemical Group Science and Technology Research Center, , Yokohama, 227–8502 Japan;4. Department of Chemistry, Carnegie Mellon University, , Pittsburgh, Pennsylvania, 15213 |
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Abstract: | The free radical reactivity ratios between styrene and different vinyl‐1,2,3‐triazole regioisomeric monomers in 1,4‐dioxane at 65 °C have been established using nonlinear least square method. The results obtained for the reactivity ratio between regioisomers show exceptionally different polymerization behavior, highlighting the effects of the electronic and steric factors of these regioisomeric monomers. The experimental results highlight the effects of the electronic and sterics on the copolymerization behavior. In case of 1,4‐vinyl‐triazoles, it was found that without the steric effects, the reactivity is very similar to that of styrene and forms random copolymers. However, it was found that 1,5‐vinyl‐triazoles are more reactive than 1,4‐vinyl triazoles. In the case of styrene‐co‐1,4‐vinyl‐1,2,3‐triazoles, the reactivity ratios were calculated to be rstyrene: r1‐octyl‐4‐vinyl‐triazole = 1.97:0.54, rstyrene : r1‐benzyl‐4‐vinyl‐triazole = 1.62:0.50, and rstyrene: r1‐methyl‐4‐vinyl‐triazole = 0.90:0.87. On the other hand, reactivity ratios for styrene‐co‐1,5‐vinyl‐1,2,3‐triazoles were found to be rstyrene: r1‐octyl‐5‐vinyl‐triazole = 0.13:0.66 and rstyrene: r1‐benzyl‐5‐vinyl‐triazole = 0.34:0.49. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51, 3359–3364 |
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Keywords: | click chemistry copolymerization Mayo– Lewis equation nonlinear least squares (NLLS) radical polymerization reactivity ratio vinyl‐1 2 3‐triazole |
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