Dimethyl meta-isopropenyl benzyl isocyanate (TMI®) is a bifunctional monomer with an unsaturation and an isocyanate group. Bulk copolymerizations of TMI with styrene, methyl methacrylate, and n-butyl acrylate were investigated. Polymerizations were carried out to low conversions in sealed test tubes at 70℃. The copolymer composition was determined using Fourier transform infrared (FTIR) spectroscopy. The data were analyzed using the terminal, as well as restricted penultimate, model of copolymerization. The method of Kelen-Tudos was used to calculate the reactivity ratios according to the terminal model. A nonlinear regression analysis was also carried out. Low reactivity ratio values for TMI were obtained for the copolymerizations with styrene and methyl methacrylate as a result of the inability of TMI to undergo homopolymerization. The value was higher for the copolymerization with n-butyl acrylate. Composition diagrams were generated, and the range of TMI concentration in the monomer charge for the preferential incorporation of TMI in the copolymer was identified.