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The Copolymerization of Vinylhydroquinone and Acrylonitrile by Tri-n-butylborane

Vinylhydroquinone (VHQ) was found to copolymerize with acrylonitrile (AN) by tri-n-butylborane (Bu3B) in cyclohexanone at 35°C under nitrogen atmosphere. IR-, UV-, and NMR-spectral studies revealed that VHQ copolymerized in terms of vinyl polymerization. Monomer reactivity ratios for VHQ (M1) and AN (M2) were r1=0.46 and r2=0.02. Q and e values were also calculated; Q1=1.9 and e=–1.0. These r and e values, which are similar to those for styrene (St), and other data suggest that VHQ behaves like St rather than as an inhibitor in the Bu3B-initiated copolymerization. No homopolymerization occurred under the same conditions either under a nitrogen atmosphere or in the presence of oxygen. The reaction mechanism is also discussed.