Naphthalene-based azo dyes: Synthesis, characterization and dyeing performance on polyester fibers (original) (raw)
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Novel naphthalimide based azo disperse dyes for dyeing of polyester fabrics
series of monoazo disperse dyes based on naphthalimide was synthesized using N-alkylcarboxylic acid-1,8-naphthalimide as diazo component and N,N-diethylaniline derivatives as a coupling components. 4-amino-N-ethanoic (propanoic) acid-1,8-naphthalimide was synthesized from 4-nitro-1,8-naphthalic anhydride by imidation and subsequent reduction reactions. These compounds were diazotized and further coupled to substituted N, N-diethylaniline to produce dyes which give red to violet hues on polyester fabrics. The prepared dyes and their corresponding intermediates were characterized by elemental analysis, DSC, FTIR, 1 HNMR and UV-Vis spectroscopic techniques. The dyed polyester fabrics showed moderate light fastnesses, very good to excellent washing, rubbing and sublimation fastnesses.
Journal of The Serbian Chemical Society, 2020
A series of monoazo disperse dyes were synthesized by coupling diazotized 4-amino- N -dodecyl-1,8-naphthalimide with N,N -dialkyl anilines and naphthol derivatives. The synthesized intermediates and the dyes were characterized using FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis (CHN). Visible absorption spectra of the dyes were examined in solvents of different polarities. The electronic absorption spectra cover a wavelength ( λ max) range of 515–535 nm in DMF at uniformly absorption intensity between 1.59–3.00×104 L mol-1 cm-1. The dyes gave deep and bright intense hues of light violet, maroon, pink and neon red on polyester fabrics. The dyes generally showed good washing and perspiration rating but poor to moderate light fastness properties on woven polyester fabric and could be recommended for commercial outlets.
Journal of the Textile Institute, 2014
A series of novel mono azo-naphthalimide dyes containing butyric acid group are applied on the wool-polyester blend fabrics in a one-bath, single-stage dyeing method. Results showed that the dyes containing N-ethyl-n-(2-hydroxyethyl)-aniline, N,N-diethylaniline, and N,N-diethyl-m-toluidine demonstrated reasonably good buildup (K/S > 8). The spectrophotometric data indicated that the hues of dyed fabrics were red to bluish red. The color characteristics data of dyed fabrics showed that the wavelength of the maximum absorption of dyed samples depends on various substitutions on coupling components in dye molecules. The consequence of significant operating parameters such as pH, time, and temperature reaction in the dyeing process was evaluated. Fastness properties of dyed fabric such as washing, rubbing, and perspiration were acceptable (3-5). The consumptions of energy, chemicals, water, and time of dyeing process were reduced by utilizing these dyes. The results of this study support the potential production of new environmentally friendly dyes for coloration of wool-polyester blend fabrics.
Coloration Technology, 2008
The dyeing of polyester-cotton blends with new alkali-hydrolysable azo disperse dyes based on N-ester-1,8-naphthalimide was investigated. Polyester-cotton blend fabrics were dyed using both one-and two-bath methods. Dyes 3 and 4 offered lower colour yield on polyester using the one-bath method. For the rest of the dyes, employing either the one-or two-bath method resulted in a similar colour yield on polyester fabric. The results for fastness properties and colour yield of the dyeings showed that the dyes were suitable for dyeing polyester-cotton blends using the one-bath method. The kinetic study of hydrolysis of the dyes in alkali media obeyed the pseudo first-order reaction rate.
2017
This present work aims to investigate dyeing performance of some new azo disperse dyes belonging to diazotization of 1, 4-bis (2-amino-1, 3, 4-thiadiazolyl) benzene and coupling with different amines as to comparing and contrasting depth obtained of shade and levelness. Some new dyes, such, has been examined, and assessed. The study was concerned mainly with dye uptake, behavior and efficiency. Color measurements, kinetics and thermodynamic parameters were involved. Conventional dyeing, was considered as control for obtained results. © 2017 Elixir All rights reserved. Elixir Appl. Chem. 106 (2017) 46546-46551 Applied Chemistry Available online at www.elixirpublishers.com (Elixir International Journal) Tele: 00201155011735 E-mail address: dr_ali055@yahoo.com © 2017 Elixir All rights reserved M. S. Aboul-Fetouh et al./ Elixir Appl. Chem. 106 (2017) 46546-46551 46547 supplied by Egyptian Turkish Co. (Cairo, Egypt) and 2 g/L of Na2CO3 at 50 °C for 30 min to remove waxes and impurities, ...
Open Journal of Applied Sciences, 2012
The synthesis of a series of 3-(p-substituted phenylazo)-6-pyridone dyes which is suitable for the dyeing of polyester fabrics, is described. Visible absorption spectra of the dyes were examined in various solvents and the compounds in solution exhibited hydrazone-common anion equilibrium. The electronic absorption spectra cover a λ max range of 404-464 nm in DMF at uniformly high absorption intensity between 5.33 × 10 4-8.55 × 10 4 l•mol-1 •cm-1 and gave bright intense hues of yellow to orange on polyester fabrics. The colour parameters of the dyed fabrics were measured and the dyes have excellent exhaustion between 72%-79% for polyester fabrics, more intense and of very good fastness properties on polyester fabrics. The remarkable degree of levelness and brightness after washing is indicative of good penetration and excellent affinity of these dyes for the polyester fabric.
Middle East Journal of Applied Sciences, 2018
Excellent color fastness and dyeing properties were exhibited when fibers dyeing treating by these azo polymeric dyes. Further on, to gain insight the mode of action of the synthetic compounds as antibacterial agents, docking studies were performed for the synthetic compounds in order to evaluate their activity as anti-bacterial agents. Virtual screening of all the compounds was performed against 2 bacterial proteins (DNA gyrase subunit B, and penicillin binding protein 1a) that are known targets for some antibiotics. The fastness properties of dyed polyester, wool and its blend such as washing, rubbing, light and perspiration are study.
Monoazo disperse dyes were synthesized from 4-aminobenzaldehyde and 4amino -3nitrobenzaldehyde as diazo components. The Diazonium solutions from both components were coupled to various coupling components such as 1-naphthol, 2-naphthol, resorcinol, phloroglucinol and phenol to produce series of dyes with hydroxyl group(s). The physical characteristics of the dyes such as melting point, molecular weight, yield and colour were studied. The dyes were characterized using Ultraviolet, Infrared and Gas chromatography -mass spectrometry. The Infrared Spectroscopy confirmed the presence of the functional groups in the intermediates and dyes. The observed functional groups are O-H, N-H, N=N, C=C of aromatic, C=O and C-H. The functional groups absorbed at frequencies consistent with literatures. The mass spectroscopy revealed that the molecular ion peaks were consistent with the molecular mass of the proposed structures while some daughter ions and base peaks were observed based on some fragmentation patterns. The mass
Journal of the Serbian Chemical Society, 2010
Novel acid mono azo and mordent acid mono azo dyes were synthesis by the coupling of diazonium salt solution of different aromatic amines with 2-hydroxy-4-methoxybenzophenone. The resulting dyes were characterized by spectral techniques, i.e., elemental analysis, IR, 1H-NMR and UV-visible spectroscopy. The dyeing performance of all the dyes was evaluated on wool and silk fabrics. The dyeing of chrome pre-treated wool and silk fabrics showed better hues on mordented fabrics. Dyeing of wool and silk fabrics resulted in pinkish blue to red shades with very good depth and levelness. The dyed fabrics showed excellent to very good light, washing, perspiration, sublimation and rubbing fastness. The results of antibacterial studies of chrome pre-treated fabrics revealed that the toxicity of mordented dyes against E. coli, S. aureus, S. typhi, B. subtilis bacteria was fairly good.