On the basis of the
reaction of 5,5-dimethylhydantoin potassium
salt with dibrominated alkane, a series of hydantoin derivatives in
which two hydantoin rings are bridged by an alkyl chain with different
length (C2, C6, C8, and C12) were synthesized. Upon chlorination,
these compounds were transformed into hydantoin-based N-halamines. The structures of these samples were fully characterized
with 1H NMR, FT-IR, UV/vis, thermal analyses, and iodometric
titration. The antibacterial activity of these N-halamines
was assessed with 4 × 109 CFU/mL of Gram-negative Escherichia coli under different chlorine concentrations
and over different periods of contact time. It was found that the
antibacterial properties and the releasing characteristics of the
active chlorine of the hydantoin-based N-halamines
changed obviously with increased alkyl chain length, and the factors
influencing the antibacterial efficacy were discussed in terms of
water solubility, steric effect, electron-donating effect, and action
mechanism.