Reactions of cotton or diethylaminoethyl cotton with 1‐chloro‐2,3‐epithiopropane

Sulfhydryl groups have been introduced into cotton and into diethylaminoethyl (DEAE)‐cotton by reaction with neat 1‐chloro‐2,3‐epithiopropane or alcoholic solutions of the thiirane. Reactions at room temperature have been compared with those at higher temperatures, and fabric properties obtained with various S/Cl ratios have been compared. The effects of additional external base catalysis on these reactions have been studied. Fabric properties resulting from cotton–1‐chloro‐2,3‐epithiopropane or DEAE‐cotton–1‐chloro‐2,3‐epithiopropane reactions have been compared with properties obtained with the corresponding reactions of cotton or DEAE‐cotton with epichlorohydrin. Sulfhydryl groups have also been introduced into cotton and DEAE‐cotton by the in situ formation of 1‐chloro‐2,3‐epithiopropane in the fabric as a result of the reaction of the oxygen analog with a thiourea or a thiocyanate. These in situ reactions have been carried out in the absence and presence of solvent and external base catalysts. Attempts to vary the wet and conditioned (dry) recovery angles by oxidation of sulfhydryl groups and by reduction of disulfide groups met with little success. Smaller improvement in wrinkle recovery properties imparted by the thiirane than by epichlorohydrin at a given add‐on has been explained on the basis of greater tendency of the thiirane to open abnormally in neutral or slightly acidic conditions and thus the greater tendency of the thiirane to form polymers rather than to crosslink cotton. Tendency of the oxirane to open normally and therefore act difunctionally results in finished fabrics with low chlorine contents, a high degree of crosslinking, and little polymer formation.