This Is AuburnElectronic Theses and Dissertations

Synthesis and Application of Novel Biocidal Materials




Zhu, Changyun

Type of Degree



Chemistry and Biochemistry


For this study, a new N-halamine, 1-(2, 3-epoxypropyl)-6-methyluracil, was synthesized and was coated onto cotton fabric. The treated cotton was then activated by chlorination using Clorox bleach. The cotton swatches were found to deactivate E.coli in 1 min contact time and S. aureus in 5 min contact time and retained their biocidal activity even after 50 washing cycles. The chlorine lost was easily recovered in recharging in household bleach. This reaction is very efficient, and the reaction solution can be used directly in the finishing bath in the manufacturing process. The potential applications of this biocidal cotton fabric include use in hospitals as bed sheets and clothes for patients. This type of cotton can also be used in antimicrobial masks to stop Gram negative and Gram positive bacteria. Another new N-halamine monomer, N-allyl-6-methylpyrimidine, was also synthesized and was copolymerized with commercial vinyl acetate (VAC) to form a copolymer VAC-co- N-allyl-6-methylpyrimidine useful for film coating. A series of VAC-co-N-halamine copolymers, VAC-co-3-(3’-allyl-5’-methylhydatoinyl)acetanilide, VAC-co-5-methyl-5-(3’-propenyl)hydantoin, VAC-co-3-allyl-6,6-dimethyl-1,3,5-triazinane-2,4-dione, and VAC-co-5,5-dimethylhydantoin-1-ylmethylene acrylate were also synthesized. Those films had biocidal activity after treatment with Clorox bleach. The surface coated copolymer contained 2.0×1017 to 9.0×1017Cl+ atoms/cm2. The films produced in this research were able to kill both Gram-positive and Gram-negative bacteria. Those polymers have many potential applications in medical devices, hygienic materials, and in the food-processing industry.