Synthesis and characterization of new azo compounds linked to 1,8-naphthalimide as new fluorescent dispersed dyes for cotton fibers

Abstract

New Azo compounds containing of 1,8-naphthalimide moiety had been synthesized from 1,8-naphthalic anhydride by reaction with p-phenylenediamine or benzidine to give 1,8-naphthalimide derivatives [1 or 2], which converted into its diazonium salt derivatives that undergo to coupling reaction with different substituted phenol in alkaline media to produce azo compounds derivatives [3-6]. The prepared compounds had been characterized by measuring some of physical properties (melting point), FTIR, 1HNMR and 13CNMR. Also, absorption spectra (UV-Vis spectrophotometry), fluorescence spectra (Fluorescence spectrophotometry) and quantum yield of prepared azo dyes [3-6] had been studied in four different solvents of different polarities (EtOH, dioxane, CHCl3 and DMSO). Also, the photo stability of the dyes [3-6] was studied by exposing to the ultraviolet light at room temperature for three hours. Thermal stability of dyes (3 & 4) was studied by TGA/DTG. The prepared dyes [3-6] were used for the dyeing of raw cotton dyeing at high temperatures and studying their fastness properties such as washing fastness using standard soap (SDS) and rubbing fastness (wet and dry) under controlled conditions of pressure, speed and moisture.