Synthesis and characterization of isocoumarin derivative polymer

In current study, 3-acetyl isocoumarin compound was synthesized by the solvent-free reaction of 2-carboxybenzaldehyde and mono-chloroacetone in the present of TEA. This compound was converted to 3-(2-bromo acetyl) isocoumarin compound via its bromination in the present of glacial acetic acid. Then, a new isocoumarin derived monomer 2-(isocoumarin-3-yl)-2-oxoethyl methacrylate monomer was synthesized by the reaction of that compound with sodium methacrylate under the appropriate conditions. Spectral characterizations were accomplished with FT-IR, 1H-NMR and 13C-NMR techniques. By the free radical polymerization of monomer, poly(2-(isocoumarin-3-yl)-2-oxoethyl methacrylate) polymer was synthesized. The glass transition temperature of polymer was found to be 161.69 oC by DSC technique. Thermal behaviors and decomposition mechanism of isocoumarin derived polymer was investigated by TGA method in detail. Thermal degradation activation energy of polymer was calculated as 136.12 kJ/mol and 134.83 kJ/mol by Flynn-Wall-Ozawa and Kissinger methods, respectively. Thermal degradation mechanism of polymer was followed with a deceleration type one dimensional diffusion mechanism (D1) at the optimum heating rate of 5 °C/min.