Synthesis and Characterization of Antibacterial and Temperature Responsive Methacrylamide Polymers

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Abstract

A new methacrylamide monomer (MAMP) containing a pyridine moiety was synthesized by reacting methacrylic anhydride and 3-(aminomethyl) pyridine. The monomer was homopolymerized in 1,4-dioxane and copolymerized with N-isopropyl acrylamide in DMF at two different compositions using AIBN as an initiator. The pyridine groups of the homopolymer and copolymers were reacted with various bromoalkanes containing 12, 14, and 16 carbon alkyl chains to obtain the polymers with pendant pyridinium groups. The monomer and polymers were characterized by elemental analysis, NMR, FTIR, SEC, TGA, and DSC. The neutral and quaternized copolymers with low MAMP content were water-soluble and showed temperature-responsive behavior in aqueous solutions. The lower critical solution temperatures (LCSTs) of these polymers varied between the temperatures of 25 and 42 °C. The LCST of quaternized copolymers were higher than that of the neutral copolymer because they were more hydrophilic. The LCST of the quaternized copolymers decreased with an increase in the alkyl chain length on the pyridinium group because the copolymers became more hydrophobic this way. The antibacterial activities of water-soluble copolymers were investigated against Staphylococcus aureus and Escherichia coli using the broth dilution and spread plate methods, whereas the water-insoluble polymers were tested for the antibacterial activity against the same types of bacteria using the shaking flask method. The quaternized water-soluble copolymers showed excellent antibacterial activities against both types of bacteria, whereas the neutral polymers and quaternized water-insoluble homopolymers and copolymers were not active.

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