Novel quat/di-N-halamines silane unit with enhanced synergism polymerized on cellulose for development of superior biocidability

Abstract

A silane unit with enhanced synergism that is realized using one cationic quaternary ammonium salt (QAS) to draw anionic bacteria to two N-halamine functionalities was designed and polymerized on cellulose for superior biocidability. A monomer containing one tertiary amine, one amide N–H, and one imide N–H, was synthesized via alcoholysis of 3-triethoxysilylpropyl succinic anhydride with 2-(dimethylamino)ethan-1-ol and following esterification with 5-(4-hydroxyphenyl)hydantoin. The triethoxysilyl groups of the monomer were hydrolyzed to silanol groups to condense with counterparts in different hydrolyzates and with hydroxyl groups on cellulose to form a polymeric modifier. Each silane unit of the modifier has one QAS and two N-halamine functionalities (quat/di-N-halamines) after quaternization of the tertiary amine and chlorination of the amide and imide hydrogens. The resultant cellulose suppressed (7 logs) both Staphylococcus aureus and Escherichia coli within 3 min, demonstrating an enhanced synergism since the inactivation rate is faster than counterparts decorated with only N-halamine and with synergistic units of one cationic center and one N-halamine. The modifier exhibited promising stability and rechargeability toward washings, UV irradiation, and long-term storage. The proved enhanced synergism from the integration of one cationic center with multiple N-halamines directs the synthesis of more powerful biocides for developing antibacterial polymers.