Engineering of super bactericidal cotton using pyridinium/di-N-chloramine siloxane with intensified synergism

Tuning the ratio of complementary biocidal groups in a composite unit is proved to be a tactic to better minimize their weaknesses to realize higher synergism. A silane with precursors of one pyridinium and two N-chloramine sites, 6-(pyridin-4-yl)-3-(3-(trimethoxysilyl)propyl)-1,3,5-triazinane-2,4-dione, was synthesized, hydrolyzed and dehydrocondensed into a silicone modifier on cotton cellulose. Specially, isonicotinaldehyde was ammonolyzed with biuret to produce 6-(pyridin-4-yl)-1,3,5-triazinane-2,4-dione that subsequently reacted with (γ-chloropropyl)trimethoxysilane to synthesize the silane through nucleophilic substitution. The modifier on cotton was quaternized and chlorinated to transform the one pyridine and two amide N–H structures in each unit of the silicone to pyridinium and N-chloramine counterparts. The cationic pyridinium increases the hydrophilicity of the unit and draws anionic bacteria to its two adjacent highly fatal N-chloramine sites, achieving a faster contact-killing rate than not only monofunctionality but also basic synergistic integration of one cationic center and one N-chloramine. This phenomenon is therefore referred to as “intensified synergism” and provides crucial information for the design of more powerful biocides. The pyridinium/di-N-chloramine silicone coating exhibited extraordinary durability towards UV irradiation, washing cycles and long-term storage due to the good UV resistance and chemical inertness of pyridinium and silicone backbone.

Graphic abstract