New azo Schiff base disperse dyes were synthesized based on the chromene moiety through a condensation reaction of resorcinol, malononitrile, and 4-chlorobenzaldehyde in ethanol, yielding 2-amino-4-(4-chlorophenyl)-7-hydroxy-4H-chromene-3-carbonitrile, which contains a free amino group. The produced chromene primary amine can react to form new Schiff bases when they interact with vanillin as an aldehyde and ninhydrin as a ketone. Next, we diazotized 2-chloro-para-nitro aniline and coupled it with our recently produced Schiff bases to obtain novel azo disperse dyes. The structures were validated using 1 HNMR, mass spectrometry (MS), and Fourier Transform Infrared Spectroscopy (FTIR). Our recently developed azo disperse dyes assessed all color attributes and antimicrobial activity against Staphylococcus aureus ATCC 6538-P the gram-positive bacteria, Escherichia coli ATCC 25933 as the gram-negative bacteria, Candida albicans ATCC 10231 as yeast, and the filamentous fungus Aspergillus niger NRRL-A326 on nylon and polyester textiles. The K/S values of the dyed samples were measured, and the results indicated that the investigated dyes imparted excellent color fastness properties. The dyed samples exhibited strong resistance to fading when exposed to light, washing, rubbing, and perspiration.