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Copolymers of a novel amphiphilic methacrylate monomer based on the hydroxyl group: copolymerization kinetics, thermal properties, biological activity, and swelling behavior

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Abstract

In this work, in a first step, a novel methacrylate monomer, 2-(4-hydroxyanilino)-2-oxoethyl-2-methylprop-2-enoate (HAOEME), was synthesized containing a phenolic hydroxyl group in the side branch. Then, the copolymers of this monomer were obtained by a free radical solution polymerization method with glycidyl methacrylate (GMA), a commercial monomer, at 65 °C in 1,4-dioxane solvent. The structural characterization of the synthesized monomers and copolymers was carried out using Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (1H NMR), and 13C NMR techniques. Based on the monomer reactivity ratios obtained, the HAOEME monomer was found to be more reactive than GMA. The thermogravimetric analysis results showed that the thermal resistance of copolymers increased with an increase in the number of HAOEME units in the copolymer. It was also observed that the Tg value of copolymers increased with an increase of the molar fraction of HAOEMA units in the copolymer. The thermal degradation activation energy values of the polymers were determined using approaches including the Kissinger and Ozawa methods. The result of the biological activity studies revealed that the copolymers show moderate activity against different bacterial and fungal species. The swelling properties of the polymers were investigated using water. The variations in the swelling percentages were examined according to time and temperature parameters.

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Acknowledgements

This study is supported by Afyon Kocatepe University Scientific Research Projects Coordination Unit. Project Number 14-FENB-26. The author is grateful to Dr. Zeki GÜRLER for the study of biological behavior.

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  1. Department of Chemistry, Faculty of Science and Arts, University of Afyon Kocatepe, Afyonkarahisar, Turkey

    İbrahim Erol & Murat Özer

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  1. İbrahim Erol
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Correspondence to İbrahim Erol.

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Erol, İ., Özer, M. Copolymers of a novel amphiphilic methacrylate monomer based on the hydroxyl group: copolymerization kinetics, thermal properties, biological activity, and swelling behavior. J Polym Res 28, 372 (2021). https://doi.org/10.1007/s10965-021-02712-w

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