Use of dihalohydrin precursors of butadiene diepoxide in the chemical modification of cotton cellulose

Dihalohydrin precursors of meso-butadiene diepoxide or d,l-isomers of butadiene diepoxides have been reacted with cotton cellulose. It has been shown that d,l-2,3-dibromo-1,4-butanediol, d,l-2,3-dichloro-1,4-butanediol, meso-2,3-dichloro-1,4-butanediol, and meso-1,4-dichloro-2,3-butanediol, can be added to cotton in small amounts (1–4%) to increase both dry and wet crease resistance of the fabric. Several methods of application were investigated, and two methods for the in situ formation of the butadiene diepoxides in cotton and their subsequent reaction with cellulosic hydroxyls rather than solvolysis have been proposed. Both processes call for the application of the dihalohydrin from an aqueous solution and subsequent treatment of the dried fabric by either of the following: (1) absolute alcoholic solution of NaOH or (2) concentrated aqueous solution of Na4SiO4 saturated with NaCl. With the former, a slow curing of the dehydrohalogenated sample in a sealed polyethylene bag at room temperature or a rapid high temperature cure could be used; with the latter, increased dry and wet crease resistance was obtained only with a rapid high temperature cure. Use of aqueous orthosilicate solutions offers a potential commercial application, since the dihalohydrins are relatively inexpensive and such a process avoids handling of the volatile and relatively toxic butadiene diepoxides. Typical fabric properties obtained with the various methods are included.