Synthesis and characterization of high wash fastness novel azo reactive dyes incorporating aromatic bridged diamines

A new series of azo reactive dyes containing free chlorine atoms have been synthesized. The synthetic methodology involves the diazotization of 4′4-diamino diphenylamine-2-sulfonic acid (2) followed by azo coupling with 1-amino-8-naphthol-3,6-disulfonic acid (3) in alkaline medium to yield intermediate dye (4). Condensation of the latter with 1,3,5-trichlorotriazine afforded the cyanurated dye (5). A number of novel bis aromatic diamines (1a-j) were separately synthesized as bridging groups and were coupled with cyanurated dye (5) at room temperature to provide the target dyes designated as S1-S10 containing triazine and linker in a single molecule. The structures of newly synthesized compounds were confirmed by analytical data and spectroscopic techniques. The synthesized dyes were applied on cotton fibers to assess their light fastness, wash fastness and rubbing fastness and were found to possess medium to high fastness values in different dyes.