Naphthoquinone disperse dyes and their dyeing application to polyethylene terephthalate fabrics

Examination of natural quinone dyes and their dyeing properties exist in the literature. However, disperse dyeing of synthetic quinone dyes on textile materials and examination of these properties are quite rare. In this study, the derivatives of new N-,O-heteroatom-substituted-1,4-naphthoquinone dyes were synthesized with the reactions between 2,3-dichloro-1,4-naphthoquinone with some aromatic and aliphatic N-nucleophiles according to Michael addition mechanism and the exact structure of dyes were specified by using various spectroscopic methods (FT-IR, 1H NMR, 13C NMR, MS, and UV/Vis.) and microanalyses. In the second step of this work, the polyethylene terephthalate fabrics were dyed with these newly synthesized disperse dyes. Dyeing performances such as dye exhaustion (%), color, and color fastness (to washing, alkaline perspiration, acidic perspiration, water, seawater, wet rub, dry rub, sublimation, and light fastness) properties of these dyes on PET fiber fabrics were investigated and compared. The highest color yield (K/S) by 12.33 was obtained with dye compound 10 at a dyeing depth of 3% owf and displayed better dyeing performance than the other dyes studied. In conclusion, PET fibers dyed with dye 2-4-(4-Chlorofenoxyaniline)-3-chloro-1,4-naphthoquinone (dye compound 10) displayed the highest dye exhaustion (%) values, the highest color yields, and excellent washing, perspiration (alkaline and acidic), water and seawater and rub (dry and wet) fastness values with no staining whatsoever.