Synthesis, homopolymerization and properties of p-aminopyridine methacrylate

Abstract

For the first time, p-aminopyridine methacrylate was synthesized by a reaction between p-aminopyridine and methacryloyl chloride. IR and NMR spectroscopy сonfirmed the obtained compound structure. Radical homopolymerization of synthesized p-aminopyridine methacrylate was carried out either in bulk or in benzene solution (initiator – AIBN). The study of radical polymerization regularities of p-aminopyridine methacrylate discovered no side reactions and induction period of the reported process under the created conditions with a maximum yield of 92%. It was found that p-aminopyridine methacrylate is a more reactive monomer in radical polymerization as compared to methyl methacrylate. The structure of the obtained monomer and polymer was investigated by IR and NMR spectroscopy. Based on these data, the polymerization proceeds by a double bond, with substituents in the side macro chain remaining unreacted. The study of the synthesized monomer polymerization in the bulk indicated the presence of the gel effect. The autoacceleration begins at ~25% monomer conversion during the polymerization process, which agrees with the literature data. It was discovered that the polymerization of p-aminopyridine methacrylate proceeds at a rate higher than that of methyl methacrylate. This observation is likely to be connected with the substituent contribution to the electronic state of the entire monomer molecule. Hence, the electron density of the vinyl group changes and the growing radical becomes stabilized with the substituent –M-effect. The polymer synthesized possesses high antimicrobial properties.