Synthesis of some 4-arylazo-3-hydroxythiophene disperse dyes for dyeing polyester fabrics

A series of novel 4-arylazo-3-hydroxythiophene disperse dyes was synthesized by heterocyclization of ethyl 2-arylhydrazono-2-phenylthiocarbamoyl acetates with a variety of α-halogenated reagents. The structures of the synthesized dyes were confirmed by UV-Vis, IR, ¹H NMR, and MS spectroscopic techniques and elemental analysis. The dyes were applied to conventional polyester fabric by high temperature exhaust dyeing. These dyes were found to give orange to reddish-violet shades with very good depth, levelness, and brightness on polyester fabric. The dyed fabric showed moderate to good light fastness and very good fastness to washing and perspiration. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed. Correspondence: Ehab Abdel-Latif, Department of Chemistry, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt     

Substituted 5-Antipyrinylazo-4-phenyl-2-aminothiazoles as Disperse Dyes for Dyeing Polyester Fabrics

Summary. A series of some new substituted 5-antipyrinylazo-4-phenyl-2-aminothiazole disperse dyes was synthesized by diazocoupling of 4-antipyrinyldiazonium chloride with aminothiazole derivatives. The synthesized dyes were characterized by UV-Vis absorption, IR, ¹H NMR, and MS spectroscopy. The dyes gave orange to reddish-violet shades with very good depth and levelness when applied to polyester fabrics as disperse dyes and their fastness properties were evaluated on polyester fibers. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed.     

Substituted 5-Antipyrinylazo-4-phenyl-2-aminothiazoles as Disperse Dyes for Dyeing Polyester Fabrics

A series of some new substituted 5-antipyrinylazo-4-phenyl-2-aminothiazole disperse dyes was synthesized by diazocoupling of 4-antipyrinyldiazonium chloride with aminothiazole derivatives. The synthesized dyes were characterized by UV-Vis absorption, IR, ¹H NMR, and MS spectroscopy. The dyes gave orange to reddish-violet shades with very good depth and levelness when applied to polyester fabrics as disperse dyes and their fastness properties were evaluated on polyester fibers. Also the position of color in CIELAB coordinates (L^*, a^*, b^*, H^*, and C^*) was assessed.     

Synthesis,characterization and dyeing performance of new bisazo–bisazomethine disperse dyes

New bisazo–bisazomethine disperse dyes were prepared by the coupling of diazotized solutions of various aromatic amines with 2,2′-{methylenebis[4,1-phenylenenitrilomethylylidene]}diphenol (Schiff base). Schiff base (SB) was prepared by the condensation of 2-hydroxybenzaldehyde with 4,4′-diaminodiphenylmethane (DDM). The resultant dyes were characterized by elemental analysis, IR and ¹H NMR spectral studies. The UV–visible absorption spectral data were investigated in dimethylformamide (DMF) and are discussed in terms of structure property relationship. The dyes when applied on polyester fabric, gave golden yellow to reddish brown shades having fairly good to good light fastness, very good to excellent washing, perspiration and sublimation fastness and good to very good rubbing fastness properties.     

Synthesis and dyeing properties of some new monoazo disperse dyes derived from 2-amino-4-(2′,4′-dichlorophenyl)-1,3 thiazole

Ten new monoazo disperse dyes (4a–j) have been synthesized by coupling of diazotized 2-amino-4-(2′,4′-dichlorophenyl)-1,3 thiazole (2) with various N-alkyl derivatives of substituted aniline (3a–j) and their dyeing performance on polyester fiber has been assessed. These dyes are characterized by elemental analysis, UV–vis spectra, IR and NMR spectroscopy. The absorption maxima (λ_max) were recorded in DMF and were found to be in the range of 530–600 nm. The dyed polyester fabric showed fair to very good light fastness and very good to excellent washing and rubbing fastness properties with superior depth and levelness.     

Disperse Dyes Based on 5‐Arylazo‐thiazol‐2‐ylcarbamoyl‐thiophenes: Synthesis,Antimicrobial Activity and Their Application on Polyester

A series of novel 5‐arylazo‐thiazol‐2‐ylcarbamoyl‐thiophene derivatives was synthesized, and their chemical structures were secured by elemental and spectroscopic analyses. Their versatility for pharmaceutical purposes and textile dyeing as disperse dyes were reported. The synthesized dyes were applied to polyester fabrics by using high temperature dyeing method at 130°C. The dyed polyester fabrics displayed very good washing and perspiration fastness and moderate light fastness. Finally, the synthesized compounds showed biological activities against Bacillus subtilis, Staphylococcus aureus (Gram positive bacteria), Escherichia coli, and Pseudomonas aeruginosa (Gram‐negative bacteria), while no effect had been reported against fungi. The minimum inhibitory concentration of the most active compound was evaluated.     

Application of newly synthesized bisazo dichloro-s-triazinyl reactive dyes bearing 1,3,4-oxadiazole molecule

Novel bisazo dichloro-s-triazinyl (DCT) reactive dyes (5a–h) containing 1,3,4-oxadiazole molecule as a tetrazo component were synthesized and applied on silk, wool and cotton fibers by exhaust dyeing method. The structures of these dyes were confirmed by UV–vis, FT-IR, ¹H and ¹³C NMR and elemental analyses. The exhaustion, fixation and fastness properties of the dyed fabric were assessed and the results demonstrated that these dyes showed moderate to very good light and good to excellent washing and rubbing fastness properties. The colorimetric data (L¹, a¹, b¹, C¹, H¹, K/S) of these dyes have also been studied in detail.     

杂环-双氰乙基系列分散染料的合成、表征及染色性能

以4个杂环芳香胺为重氮组分, 3个N,N-二氰乙基芳香胺为偶合组分, 经重氮化、 偶合反应合成了12个杂环-双氰乙基系列偶氮物; 采用紫外-可见吸收光谱、 红外光谱及核磁共振氢谱等对其结构进行了表征; 还考察了它们在涤纶织物、 乙酰化杉改性木粉和氰乙基化改性木粉上的染色性能. 结果表明, 12个偶氮物为目标产物, 在N,N-二甲基甲酰胺(DMF)中的最大可见吸收波长为417～621 nm, 摩尔吸光系数均大于10⁴. 这些化合物染色涤纶织物的色光分属黄色、 红色、 紫红色和蓝色系列, 并具有高水洗牢度和高日晒牢度; 染色乙酰化木粉和氰乙基木粉的色光和水洗牢度与染色涤纶织物相近. 这12个分散染料具有色谱范围广、 色泽鲜艳、 高发色强度和高牢度等特点, 可用于多种纤维的染色.     

Disperse dyes derived from 2-amino-5-mercapto-1,3,4-thiadiazole

Some novel heterocyclic monoazo dyes based on 2-amino-5-mercapto-1,3,4-thiadizole have been synthesized by coupling with various N-phenylacrylamide derivatives. The dyeing performance of these dyes was assessed on polyester fabrics. IR and visible spectra of the dyes were examined. The percentage dye bath exhaustion, fixation, and various fastness properties of the dyes were also determined. These dyes were found to give brownish-orange to reddish-pink shades on dyeing with good depth, levelness, and brightness on fabric. The dyed fabric showed a good to excellent fastness to washing, rubbing, perspiration, and sublimation.     

Synthesis and Application of Some Alkali‐Clearable Azo Disperse Dyes Based on Naphthalimide Derivatives

A series of naphthalimide‐based alkali‐clearable azo disperse dyes containing a fluorosulfonyl group was synthesized. 4‐Fluorosulfonylaniline, 4‐fluorosulfonyl‐2‐nitroaniline and 6‐chloro‐4‐fluorosulfonyl‐2‐nitroaniline as the diazo components were prepared from N‐acetylsulfanilyl chloride and were subsequently coupled with 4‐hydroxy‐N‐3‐methoxypropyl‐1, 8‐naphthalimide. The synthesized dyes and their intermediates were characterized by the use of DSC, FTIR, ¹H NMR, ¹³C NMR, Mass spectroscopy and UV‐visible spectroscopic techniques. Spectrophotometric investigations of prepared dyes in different solvents were carried out in order to obtain their absorption maxima, molar extinction coefficients and solvatochromic effects. The obtained dyes were applied to polyester fabric by the HT method and exhibited good leveling, wash and sublimation fastnesses and moderate light fastness. The synthesized dyes showed that incorporated fluorosulfonyl group to these dyes can be converted to the dyes containing a water soluble sulfonate group in the relatively mild alkaline conditions.     

Synthesis and Characterization of Novel Monoazo Naphthalimide Disperse Dyes Containing Carboxylic Acid Group with High Heat Fastness Properties

A group of novel monoazo disperse dyes containing carboxylic acid‐1,8‐naphthalimide group has been synthesized. All intermediates and dyes were purified by recrystalization and the column chromatography method. The purified products were characterized by ¹H NMR, ¹³C NMR, FTIR, DSC, UV‐VIS and Elemental Analysis. Spectrophotometric investigations of the synthesized dyes in different solvents were carried out in order to obtain their absorption maxima, molar extinction coefficients and solvatochromic effects. The absorption maxima of the synthesized dyes in acetone varied (513‐549 nm) and the molar extinction coefficient was (17405‐38939 l/mol cm). By changing the media from chloroform to DMF, the solvatochromism effect for all dyes increased. Dispersion of the synthesized dyes was prepared in water containing dispersing agent and applied to polyester fabrics. The dyed fabrics showed that all of the synthesized dyes were suitable for coloring polyester fibers, producing deep red to bluish red with very good fastness properties.     

Disperse dyes based on 2-aminothiazole derivatives for cellulose triacetate fabric

A range of azo disperse dyes was prepared by coupling diazotized 2-amino-4-(p-nitrophenyl)-5-nitrothiazole with various substituted arylamines. Spectral properties in the infrared and visible range of the dyes obtained were investigated. All the dyes, when applied on cellulose triacetate fabric as 2% shade, showed fairly good to very good light fastness and very good to excellent fastness to washing, perspiration, rubbing and sublimation. All the dyes gave a wide range of reddish brown to indigo shades with very good depth and levelness on fabric. The purity of dyes was checked by thin layer chromatography. The percentage dyebath exhaustion and fixation on fabric was reasonably good and acceptable.     

Synthesis of Novel Azo Dyes Containing the Thiophene Moiety

A series of disperse dyes have been synthesized by diazotation of 2-aminothiophene derivative and coupling with various N-arylmaleimides. The dyes were characterized by IR spectral studies, visible absorption spectra, and elemental analysis. The dyeing performance of these dyes was assessed on nylon fabric. These dyes were found to give yellowish brown to reddish violet shades on dyeing with very good depth, levelness, and brightness on fabric. The percentage dyebath exhaustion and fixation on fabric was found to be very good. The dyed fabric showed poor light fastness and good to excellent fastness to washing, rubbing, perspiration, and sublimation.     

Partial least-squares modelling of dye fastness to light

Several physicochemical properties (¹³C-n.m.r., spectrophotometric, chromatographic, calorimetric) were measured for a series of 38 azo dyes in order to test the existence of relationships between one or more of these data sets and the fastness of the dyes on polyester fabric. The partial least-squares method was applied; it had previously proved useful in establishing structure/property relationships for the same dyes. It is shown that ¹³C-n.m.r. data can be used successfully to predict dye fastness to light. These data are quickly and cheaply obtained with small amounts of compound.     

Synthesis and Application of Disperse Dyes Based on 2-Aminothiazole Derivatives

A series of novel monoazo disperse dyes based on 2-amino-5-nitro-4-(p-nitrophenyl)thiazole were prepared using various N,N-dialkylaniline derivatives as the coupling components. The spectral properties in the IR and visible range of the dyes were investigated. The dyeing performance of these dyes was assessed on nylon fabric. These dyes were found to give a wide range of color shades from reddish brown to indigo with excellent brightness, levelness, and depth on nylon fabric. The dyed fabric showed fairly good light fastness, good to excellent fastness to wash and perspiration, and excellent fastness to sublimation. The dyebath exhaustion and fixation of the dyes on nylon were found to be very good and acceptable.     

Synthesis of Some Novel Biologically Active Disperse Dyes Derived from 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile as Coupling Component and Their Colour Assessment on Polyester Fabrics

A series of novel azo-disperse dyes containing alkylhydrazonopyridinone structures were synthesized. 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitrile (8) is synthesized by one-pot synthesis using ethyl cyanoacetate, propylamine, and ethyl acetoacetate. Compound 8 is then coupled with aromatic and heteroaromatic diazonium salts to afford the corresponding aryl- and heteroaryl-4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitriles 12a,b and 13a-c. Structural assignments to the dyes were made using NMR spectroscopic methods. A high temperature dyeing method was employed to apply these dyes to polyester fabrics. Most of the dyed fabrics tested displayed very good light fastness levels and good wash fastness. Finally, the biological activity of the prepared dyes against Gram positive bacteria and Gram negative bacteria were evaluated.     

Synthesis of 2-Azobenzo[b]thiophene Derivatives and Their Application on Nylon Fibre

A series of novel monoazo disperse dyes derived from the coupling of diazotized 2-aminobenzo[b]thiophene derivatives with N-arylmaleimides is described. The monoazo disperse dyes applied to nylon fabric and their dyeing performance has been assessed. These dyes have been found to give light yellow to reddish pink color shades with very good depth and levelness on nylon fabric. The dyed fabric shows moderate light fastness and excellent washing, rubbing, perspiration, and sublimation fastness. The percentage dyebath exhaustion on nylon fabric has been found to be good and acceptable.     

Synthesis and dyeing performance of some novel thiazole azo disperse dyes

The synthesis of some novel monoazo disperse dyes derived from 5-acetyl-2-amino-4-methylthiazole using various N-alkyl derivatives of aniline and their dyeing performance as disperse dyes have been assessed on cellulose triacetate fabric. The spectral properties of these dyes were also measured. The dyed fabric show good light fastness, very good rubbing, perspiration, washing fastness and excellent sublimation fastness. These dyes have been found to give bright yellow to maroon color shade with very good depth and levelness on fabric. The dyebath exhaustion and fixation on fabric has been found to be very good.     

Characterization,DFT calculations and dyeing performance on polyester fabrics of some azo disperse dyes containing pyrazole ring

A number of azo pyrazole derivatives and novel Schiff bases derived from azo diamino pyrazole were synthesized. These included 4-(2-arylhydrazono)-4H-pyrazole-3,5-diamines and N³,N⁵-dibenzylidene-4-(2-arylhydrazono)-4H-pyrazole-3,5-diamines. The chemical structures of the novel azo dyes were determined using UV–visible, IR, ¹H NMR, and ¹³C NMR spectroscopy. Dyeing process and tautomerism of the aforementioned azo compounds were predicted using DFT calculations. The electronic absorption spectra in methanol were observed and compared to those computed using B3LYP/6-31G(d,p). The dyeing performance of the produced disperse dyes was examined on polyester. The degree of exhaustion and the fastness properties of the dyed samples in terms of washing, perspiration, scorch, and light fastness were assessed. Moreover, the reflectance and color strength of the synthesized dyes were measured and discussed.     

Synthesis and application of disazo reactive dyes derived from sulfatoethylsulfone pyrazolo[1,5-a]pyrimidine derivatives

Two models of heterocyclic reactive dyes based on disazo pyrazoloprymidine derivatives and possessing a sulfatoethylsulfone reactive group were synthesized and characterized by elemental analysis, IR and ¹H NMR spectroscopy. The dyes were applied to cotton, wool and silk fabrics. Effects of varying dyeing conditions were investigated. The results assessed for the exhaust dyeing methods on the different fabrics indicate that these reactive dyes showed high exhaustion and fixation values. The dyed fabrics also showed very good light fastness and good to excellent washing, rubbing and perspiration fastness.