Abstract: Functionalizing a fibrous material having a plurality of hydroxyl groups includes reacting the fibrous material with a compound of Formula I: where X is a monovalent counteranion for the quaternary ammonium cation of Formula I and Hal is a halogen atom, to obtain the functionalized fibrous material. Also provided is a functionalized fibrous material prepared by any one of the methods described herein (e.g., a functionalized fiber including a moiety of Formula II: having an odor of free amine below the threshold of detection, or having an odor of free amine with degree of offensiveness of about 3 or less. The functionalized fibrous material may be dyed, and articles of clothing may be made from the dyed functionalized fibrous material.

Abstract: Functionalizing a fibrous material having a plurality of hydroxyl groups includes reacting the fibrous material with a compound of Formula I: where X is a monovalent counteranion for the quaternary ammonium cation of Formula I and Hal is a halogen atom, to obtain the functionalized fibrous material. Also provided is a functionalized fibrous material prepared by any one of the methods described herein (e.g., a functionalized fiber including a moiety of Formula II: having an odor of free amine below the threshold of detection, or having an odor of free amine with degree of offensiveness of about 3 or less. The functionalized fibrous material may be dyed, and articles of clothing may be made from the dyed functionalized fibrous material.

Abstract: The presently disclosed subject matter relates to heterobifunctional reactive dyes comprising nitrogen-containing heterocycles substituted by both halogen and vinyl sulfone moieties. In particular, the presently disclosed subject matter relates to reactive dye compounds comprising two or more halo-substituted, nitrogen-containing heterocycles and an asymmetric bridging group, wherein at least one of the two or more halo-substituted, nitrogen-containing heterocycles further comprises a vinyl sulfone substituent. In some embodiments, the bridging group has a structure based on cysteamine or cysteine. The heterobifunctional reactive dyes have high substrate affinity and can be applied to substrates, such as cotton fibers, under low salt conditions and with reduced dye material waste.