Novel regenerable N‐halamine polymeric biocides. I. Synthesis, characterization, and antibacterial activity of hydantoin‐containing polymers

Two novel cyclic‐amine monomers, i.e., 3‐allyl‐5,5‐dimethylhydantoin (ADMH) and 7,8‐benzo‐3 allyl‐1,3‐diazasprio[4.5]decane‐2,4‐dione (BADDD) were synthesized with good yields by reacting allyl bromide with 5,5‐dimethylhydantoin (DMH) and 7,8‐benzo‐1,3‐diazasprio[4.5]decane‐2,4‐dione (BDDD), respectively. The synthesized monomers were characterized by FTIR and 1 H‐NMR spectra, and copolymerized with acrylonitrile (AN), vinyl acetate (VAC), and methyl methacrylate (MMA) in a small monomer ratio of ADMH and BDDD, respectively. The copolymers were characterized by FTIR, 1 H‐NMR, and DSC studies. The N‐halamine derivatives of the corresponding copolymers were found to exhibit high antibacterial activities against Escherichia coli, and the antibacterial properties were durable and regenerable.