Vanillin and vanillyl alcohol are modifi ed into methacrylated derivatives, which are subsequently polymerized by a free-radical process. The rheokinetics of the polymerization are investigated to determine the cure behavior and optimize the polymerization conditions for these two monomers. The effects of both structure and functionalities of the vanillin-based monomers on the thermomechanical properties of the resulting polymers are investigated and discussed. The high cross-linking density of the polymers from methacrylated vanillyl alcohol results in higher storage modulus and glass transition temperature, as well as better thermal resistance, than seen in polymers from methacrylated vanillin. These properties, combined with methacrylated vanillyl alcohol's low viscosity at room temperature, make it a promising bio-based reactive diluent for unsaturated polyester resins and vinyl esters.