Terephthalic dihydrazide was obtained through aminolytic depolymerisation of polyester bottle waste by using hydrazine hydrate. It was further reacted with 4-aminobenzoic acid in the presence of polyphosphoric acid to obtain a cyclic compound, 4,4′-[5,5′-(1,4)-phenylene)bis(1,3,4-oxadiazole-5,2-diyl)dianiline, having a heterocyclic moiety. Diazotisation of this compound followed by coupling with various N,N-disubstituted anilines afford a series of novel disazo disperse dyes. The structures of these synthesised dyes were confirmed by elemental analysis and Fourier Transform–infrared, proton nuclear magnetic resonance and mass spectroscopy. Ultraviolet–visible spectra of these azo dyes in different polar solvents showed considerable variation in the wavelength of maximum absorbance (λmax). Application of these dyes on polyester and nylon fabrics using high-temperature dyeing methods gave brilliant yellowish red hues with fair to moderate light fastness and very good to excellent wash fastness and sublimation fastness.