Synthesis and antimicrobial applications of 5,5′-ethylenebis[5-methyl-3-(3-triethoxysilylpropyl)hydantoin]

A novel, durable, long lasting, N-halamine siloxane monomer precursor, 5,5′-ethylenebis[5-methyl-3-(3-triethoxysilylpropyl)hydantoin] has been prepared and characterized by 1H-NMR and FTIR for the purpose of functionalizing the surfaces of various materials. In this work, the precursor N-halamine moiety was attached by siloxane covalent bonding to surfaces of cotton fibers. Simulated laundering tests indicated that the chlorinated N-halamine structure could survive many repeated home launderings. The materials were rendered biocidal after exposure to oxidative halogen solutions, i.e. dilute household bleach. Once chlorinated, these materials were biocidal against Staphylococcus aureus and Escherichia coli. Upon loss of the halogen from either long-term use or consumption by the microbes on the surfaces, they could be simply recharged by further exposure to dilute bleach to regain biocidal activity.