Considerable work has been done in our laboratories to produce antimicrobial materials using halamines, primarily chloramines. Chloramines have a substantial history in cottons, much of it negative. Chloramines were undesirable, unstable reaction products of chlorine bleach and early permanent press resins. If the chloramine structure is carefully selected they become more stable and the adverse effects are replaced by desirable antimicrobial properties.

We will briefly review the previous work to produce antimicrobial cotton and then describe the recent progress. Monomer and polymer of the compound 3-(3-triethoxysilylpropyl)-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione have been prepared and bonded to the surface cotton. Treatment with dilute sodium hypochlorite solutions renders cotton antimicrobial. The oxidative chlorine immobilized on the cotton is stable for extended periods and can be regenerated upon eventual loss by further exposure to dilute chlorine bleaching solutions. The treated coton is biocidal against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli O157:H7. The new siloxane is superior to previous N-halamine siloxane technology in that the N-halamine moiety contains two nitrogen binding sites for chlorine, one of which is a very stable hindered amine site.