Novel methacrylate copolymers with fluorine containing: Synthesis, characterization, reactivity ratios, thermal properties and biological activity

New methacrylate based monomers 2-(4-benzoylphenoxy)-2-oxoethyl-2-methylacrylate (BOEMA), 2-(4-acetylphenoxy)-2-oxoethyl-2-methylacrylate (AOEMA), and 2-[(4-fluorophenyl)amino]-2-oxoethyl-2-methylacrylate (FPAMA), were synthesized first time. The free-radical-initiated copolymerization of AOEMA and BOEMA with FPAMA were carried out in 1,4-dioxane solution at 65 °C using 2,2′-azobisisobutyronitrile (AIBN) as an initiator with different monomer-to-monomer ratios in the feed. The monomers and copolymers were characterized by FTIR, 1H NMR and 13C NMR spectral studies. The copolymer compositions were evaluated by nitrogen content in polymers. The reactivity ratios of the monomers were determined by the application of Fineman–Ross and Kelen–Tudos methods. The analysis of reactivity ratios revealed that BOEMA and AOEMA are less reactive than FPAMA, and copolymers formed are statistically in nature. The molecular weights (M¯w and M¯n) and polydispersity index of the polymers were determined using gel permeation chromatography. Thermogravimetric analysis of the polymers reveals that the thermal stability of the copolymers increases with an increase in the mole fraction of FPAMA in the copolymers. Glass transition temperatures of the copolymers were found to decrease with an increase in the mole fraction of FPAMA in the copolymers. The prepared homo and copolymers were tested for their antimicrobial activity against bacteria, fungi and yeast.

Graphical abstractNovel methacraylate monomer with the side chain fluorine was synthesized and copolymerized with other new methacrylate monomers having pendant ketone. Figure optionsDownload full-size imageDownload as PowerPoint slide