Superhydrophobic Functionalization of Cotton Fabric via Reactive Dye Chemistry and a Thiol–ene Click Reaction

Abstract

A straightforward method for imparting superhydrophobic character to cotton textiles using methods based in textile processing and organic synthesis was developed. Cotton fabric was first treated with a common dye anchor, cyanuric chloride, which was subsequently reacted with cysteamine to yield a thiol function on the surface. Thiol–ene click chemistry was employed to attach alkyl chains to render the surface hydrophobic. Effects of temperature and reaction time on the click reaction step were investigated to optimize the process, and a water contact angle exceeding 150° was obtained after reaction at 100 °C and 60 min. Furthermore, it was shown that both AIBN and hydrogen peroxide are effective initiators for the click reaction. The efficacy of the resulting textile in separating hydrocarbons from water was demonstrated. This straightforward preparation of a superhydrophobic textile is most promising in that it is accomplished without incorporating perfluorinated functional groups or nanoparticles.