There have been several attempts to prepare polymers with anti-microbial properties by doping with various N-halamines. Cyclic N-halamines commonly known as hydantoins are an important class of anti-microbials due to their stability, rechargeability, broad spectrum anti-microbial activity and the ability to prevent resistance to the organisms. Polymerizable hydantoins are usually synthesized by tethering vinyl moieties to 5,5,-dialkyl hydantoin sacrificing the imide hydrogen in the molecule thereby restricting the halogen capture only to the amide nitrogen that results in compromised anti-bacterial activity. In order to increase the activity of the anti-microbial polymer, we have synthesized a new vinyl hydantoin monomer, (Z)-5-(4-((3-methylbuta-1,3-dien-2-yl)oxy)benzylidene)imidazolidine-2,4-dione (MBID) where both the imide and amide hydrogens are available for halogen capture. This new monomer was copolymerized with methyl methacrylate, by free radical polymerization to prepare the anti-bacterial polymer. For water purification, the anti-microbial activity of hydantoin polymers is strongly dependent on the surface area and hence their anti-microbial activity can be increased when these polymers are fabricated into microspheres or nanoparticles. Microspheres with a smooth and a rough were synthesized by dispersion polymerization of MBID with methyl methacrylate. The oxidative chlorine content of the copolymer microspheres ranged from 1.5 to 2.45 %. In order to demonstrate the water purification potential of these microspheres, a column packed with smooth or rough microspheres was challenged with water containing E. coli. The microspheres with a rough surface exhibited 6 log kill (total kill) of the bacteria within 20 minutes of exposure with at 15 mg/mL whereas those with the smooth surface required a load of 25 mg/mL to effect total kill.

Novel hydantoin based polymeric microspheres for water purification

256th National Meeting (2018)

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