In this work, we developed a novel, practical dyeing-like approach using dichloro-s-triazine-based functional compounds to introduce antimicrobial and biofilm-controlling functions onto cellulosic fibers. Sodium 4-(4,6-dichloro-1,3,5-triazinylamino)-benzenesulfonate (a dichloro-s-triazine based colorless reactive “dye”) was synthesized via the reaction between cyanuric chloride and sodium sulfanilate. The colorless reactive dye, as well as a commercial reactive blue 4, were covalently attached to cellulosic fibers at room temperature (reactive dyeing) by reacting one chloride on the dye with the hydroxyl groups on cellulose. The resultant cellulosic fibers were then hydrolyzed under alkaline conditions to transform the remaining chloride into hydroxyl groups to achieve potent antimicrobial and biofilm-controlling effects against Staphylococcus epidermidis (Gram-positive bacteria), Escherichia coli (Gram-negative bacteria), and Candida albicans (yeast). The minimum inhibition concentration and zone of inhibition tests using model compounds suggested that the antimicrobial activities could be caused by the phenol-like hydroxyl groups on the triazine rings. The antimicrobial mechanism investigations indicated that the phenol-like structures on the dyed cellulosic fibers led to microbial lysis and leakage of intracellular components. Furthermore, the reactive dyed cellulosic fibers showed excellent biocompatibility toward mammalian cells. Our strategy provided a practical antimicrobial modification technology for a wide range of related applications.

Cyanuric chloride-based reactive dyeing treatment of cellulosic fibers with antimicrobial functions

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.