A new N-halamine precursor, 3-(2,3-dihydroxypropyl)-7,7,9,9-tetramethyl- 1,3,8-triazaspiro[4.5]decane-2,4-dione (TTDD diol), was synthesized and bonded onto cotton fabrics. Fabrics with variable amounts of chlorine loading were prepared by using several concentrations of TTDD diol. A second N-halamine precursor, 3-(3-triethoxysilylpropyl)-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (TTDD siloxane), was also synthesized and bound to cotton for comparison purposes. The coated cotton fabrics contained two types of N-Cl moieties after chlorination of the amine and amide groups. Swatches with variable chlorine loadings were challenged with Staphylococcus aureus and Escherichia coli O157:H7 as a function of contact time. The biocidal test results showed that the chlorine loadings and surface hydrophobicities influenced the antimicrobial efficacies. The chlorinated swatches have also been employed to oxidize the simulant of chemical mustard to the less toxic sulfoxide derivative. (C) 2009 Elsevier Ltd. All rights reserved.