Fabric Treated with Antimicrobial N-Halamine Epoxides

• Published in: Industrial & engineering chemistry research 2007-09, Vol.46 (20), p.6425-6429
• Main Authors: Liang, Jie, Chen, Yongjun, Ren, Xuehong, Wu, Rong, Barnes, Kevin, Worley, S. D, Broughton, R. M, Cho, Unchin, Kocer, Hasan, Huang, T. S
• Format: Article
• Language: English
• Subjects: Applied sciences; Chemical engineering; Escherichia coli; Exact sciences and technology; Staphylococcus aureus
• ISSN: 0888-5885; 1520-5045
• DOI: 10.1021/ie0707568

A series of new N-halamine epoxide precursors, 3-glycidyl-5,5-dialkylhydantoins (GH's), has been synthesized by a very facile and economic method. Cellulose surfaces can be treated with GH's and rendered biocidal by exposure to halogen solutions after curing the treated material. The biocidal efficacy tests showed that the chlorinated treated cellulose surfaces were antimicrobial with contact times required for 6−7 log reductions of Staphylococcus aureus and Escherichia coli O157:H7 of 5−30 min. It was found in simulated washing tests that celluloses, such as cotton swatches, treated with 3-glycidyl-5,5-dimethylhydantoin were quite stable and could survive more than the equivalent of 50 repeated home launderings with very little loss. Upon loss of the biocidal property due to long-term use, the treated surfaces could be recharged by further exposure to dilute bleach to regain antimicrobial activity. In addition, since only water was used as a solvent for the synthesis of GH's at room temperature, the reaction solution could be directly used as a treatment solution. Stability tests showed that the reaction solutions were relatively stable at room temperature and more stable at 5 °C over a period of at least 30 d. Preliminary experiments have shown that polyester swatches can also be treated with GH's and be rendered biocidal upon treatment with household bleach. The entire process should be economical for commercial application.