Polymerization of 2-naphthyl methacrylate in the presence of electron acceptors

The polymerization of 2-naphthyl methacrylate (NM) in toluene in the presence of tetracyanoethylene and picric acid was studied dilatometrically. The overall activation energy for the polymerization was calculated both in the absence and in the presence of electron acceptors. The results (13-7 kcal/ mole for pure NM; 15-1 kcal/mole for NM in the presence of picric acid; 212 kcal/mole for NM in the presence of tetracyanoethylene) show that the influence of the electron acceptor increases with its electron affinity. To explain the kinetics, it was assumed that donor-acceptor interaction of the additives occurs not only with the aromatic ring in the monomer but also with the growing radicals.