Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity

In this work, 2-(4-acetyl-2,6-dichloroanilino)-2-oxoethyl-2-methylprop-2-enoate (CFAOMA) monomer was synthesized and characterized. Then, copolymers of this monomer with glycidyl methacrylate (GMA) were synthesized by the free radical polymerization method at 65 °C in the 1,4-dioxane solvent. Structural characterizations of all compounds were carried out using FTIR, 1 H- and 13 C-NMR techniques. The composition of the copolymers was determined by elemental analysis. The monomer reactivity ratios were by calculated Finemann-Ross(FR) and Kelen-Tudos(KT) method. Average monomer reactivity ratio values determined by both methods were found as 0.26 for CFAOMA and 0.36 for GMA. The glass transition temperature (Tg) value of polymers was determined by differential scanning calorimetry (DSC). According to the thermogravimetric analysis (TGA) data, the thermal stability of the poly(CFAOMA) was higher than copolymers. The molecular weights (Mw and Mn) and polydispersity index of the polymers were determined by gel permeation chromatography (GPC). The thermal decomposition activation energy (Ea) values of polymers were determined using the Ozawa and Kissinger methods. The Ea values of the copolymer were found between 111.03 and 134.71 kJ/ mol by the Ozawa method and 134.51–109.24 kJ/mol by the Kissinger method. Besides, the photo-stability of the copolymers was investigated. Finally, the biological activity of polymers was investigated against different types of bacteria and fungi.