Various 4-arylazoaminophenols (AAPs) and 4-arylazoaminobenzene (AAB) have been synthesized via diazo-coupling reactions. The resulting monoazo dyes were polycondensed with formaldehyde in the presence of aqueous oxalic acid. The resulting poly (4-arylazoaminophenol-formaldehyde)s (PAAP-F)s and poly (4-arylazoaminobenzene-formaldehyde) (PAAB-F) were characterized by yield, melting point, color, solubility, viscosimetry, 1H-NMR, Visible and IR Spectroscopy. Their dyeing performance on nylon and polyester was assessed. The dyeing on nylon and polyester had yellow and orange shades with moderate to good light and wash fastness. Polymerizations of the monomeric dyes on dyed nylon and polyester have also been carried out. The dyeing properties of the monomeric and polymeric dyes were compared with the dyes polymerized on nylon and polyester and the fastness properties were found to increase on polymerization and even better with the ones polymerized on Nylon and Polyester.