Synthesis of monoazo disperse dyes derived from N-(1-phthalimidyl)-naphthalimides and their dyeing properties on polyester fabrics

PurposeThis paper aims to synthesize a novel series of monoazo disperse dyes based on N-(1-phthalimidyl)-naphthalimides by coupling with substitute anilines, naphthylamines and naphthol derivatives. Design/methodology/approachThe purification of the intermediates and the dyes was carried out by recrystallization. The structures of the synthesized intermediates and the dyes were elucidated by spectroscopic techniques. The absorption maxima, molar extinction coefficient and halochromic properties of the dyes were determined spectrophotometrically using solvents of different polarity. FindingsThe dyes were applied on polyester using a high-temperature high-pressure dyeing machine, and the dyeing performance parameters such as colour build-up on fabrics, wash fastness, perspiration fastness and light fastness were evaluated. The colour build-up was found to be very good and the wash fastness (4-5) and perspiration fastness (4-5) were excellent, whereas the light fastness was found to vary from moderate to very good (3-6). Research limitations/implicationsIt is not possible to investigate the structure of the synthesized dyes by nuclear magnetic resonance spectroscopic analysis due to the low solubility of dyes in deuterated solvents. Originality/valueA novel method for the synthesis of a new category of monoazo disperse dyes based on N-(1-phthalimidyl)-naphthalimides was developed. These dyestuffs could be used in textile printing of polyester fabrics.