Synthesis and dyeing properties of new disazo disperse dyes for polyester and nylon fabrics

Diazotized aryl amines were coupled with two stenhouse salt namely, N-(5-phenylamino-penta-4-ol-2,4-diene-1-ylidene)anilines hydrochloride [S₁ (RH) or S₂ (ROH)] to furnish two series of disazo disperse dyes (S₁D_1–10 and S₂D_1–10). The structure of all the dyes was established by estimating number of azo groups, elemental analysis and spectral studies (IR, ¹H-NMR, UV/Visible). The structure–property relationship was discussed by using electronic absorption spectra of the dyes. These dyes were applied to polyester and nylon fabrics as disperse dyes by using temperature exhaust dyeing method. The relevant dyeing characteristics, such as dyeability on fabrics, wash-fastness and light-fastness were evaluated. Fabrics dyed with these dyes furnished generally deep and bright intense hues ranging from light yellow to orange to reddish brown. The color fastness of the dyed fabric was assessed by determining wash-fastness and light-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.     

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.     

Measurement and correlation of solubilities of C.I. Disperse Red 73, C.I. Disperse Yellow 119 and their mixture in supercritical carbon dioxide

The solubilities of disperse dyes and their mixture in supercritical carbon dioxide are important to the fundamental research and development of supercritical fluid dyeing (SFD). The solubilities of Disperse Red 73, Disperse Yellow 119 and their mixture in supercritical carbon dioxide were measured in the temperature range from 343 to 383 K and pressures from 12 to 28 MPa by a static-recirculation method. The results show that over the entire range of experimental conditions in the binary (Disperse Red 73 + CO₂ and Disperse Yellow 119 + CO₂) and ternary (Disperse Red 73 + Disperse Yellow 119 + CO₂) systems, the solubilities increased with increasing pressure and temperature and were clearly affected by the molecular polarity of the dyes. A co-solvent effect and a competing dissolution effect existing in the ternary system led to the increase and decrease in the solubilities of Disperse Yellow 119 and Disperse Red 73, respectively. The solubility data of the two dyes and their mixture were correlated with two empirical models—the Chrastil and the Mendez-Santiago/Teja (MT) model.     

Synthesis and characterization of reactive dyes based on 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid

A series of new quinazolinone based mono azo reactive dyes (D_1–10) have been prepared by subsequent diazotization of 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid (C) and coupling with various 4-chloro anilino cyanurated coupling components. These dyes give purple, red, orange and yellow color shades. All the reactive dyes were characterized by their percentage yield, UV–Vis spectroscopy, elemental analysis, IR spectroscopy, ¹H NMR spectroscopy and dyeing performance on silk, wool and cotton fibres. The percentage dye bath exhaustion on different fibres has been found to be reasonably good and acceptable. The dyed fibres show moderate to very good light fastness and good to excellent washing and rubbing fastness.     

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.     

Polyelectrolyte complexes. V. Solid‐state properties of some polycation/azo dye complexes controlled by the dye structure

The solid‐state properties of some polycation/azo dye complexes according to the dye structure were studied in this work. One polycation contained about 95 mol % N,N‐dimethyl‐2‐hydroxypropyleneammonium chloride units in the backbone (PCA₅), and eight azo dyes, different in either the number of sulfonic groups or their distribution, were used as opposite components. The selected azo dyes were as Crystal Scarlet, Congo Red, Crocein Scarlet MOO, Ponceau SS, Amaranth, Ponceau S, Direct Blue 1, and Direct Red 80. Information on the compensation degree of the oppositely charges was obtained by the elemental analysis of the solid‐state polycation/dye complexes (the experimental contents of chlorine, nitrogen, and sulfur were compared with the calculated values). Differential scanning calorimetry was employed to probe the strength of the intermolecular interactions in the PCA₅/dye complexes. Wide‐angle X‐ray diffraction was used to assess the supramolecular order of the solid‐state complexes. The physical properties of the PCA₅/azo dye complexes (the complex stoichiometry, glass‐transition temperature, decomposition temperature, and degree of supramolecular order) were influenced mainly by the dye structure but also by the polycation concentration and the presence of NaCl. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 264–272, 2003     

Synthesis of Some New Thiazolo[3,2‐a]pyrimidine Derivatives and Their Applications as Disperse Dyes

A series of novel thiazolo[3,2‐a]pyrimidine derivatives were synthesized by using β‐ketoanilides 1a–c as starting materials and as key intermediates for preparation of new pyrimidinecompounds 3a–e and fused heterocyclic pyrimidine derivatives 5a–c . The new compounds were transformed to disperse dyes 6a,b and 7 . The chemical structures were elucidated by spectroscopic and elemental analyses and found to be in good agreement with the proposed structures. The versatility of compounds 6a,b and 7 for textile dyeing as disperse dyes was reported. The synthesized dyes were applied to polyester fabrics by using high temperature dyeing method at 120°C. The dye uptake expressed as color strength (k/s) of the dyed samples has been measured. Moreover, the color strength was examined in detail. In addition, the position of color in CIELAB coordinates (L*, a*, b*, h, and C*) was assessed. The color fastness of the dyed samples gave excellent results for washing and rubbing; however, the light fastness was moderate. Raman spectra of dyed samples unequivocally excluded ring dyeing and found to match with the proposed structures.     

Synthesis of new reactive dyes containing commercial UV-absorbers with enhanced simultaneous dyeing and anti-UV properties for cotton fabric

Two new reactive anti-UV dyes were synthesized based on two commercial UV-absorbers, ethyl 4-aminobenzoate for dye 1 and 4-aminobenzophenone for dye 2, which were incorporated in a structure modified from commercial reactive dye CI Reactive Red 198 (dye 3). Optimum exhaustion and total fixation values were achieved at 80 ​g/l sodium sulphate for dye 1 and 60 ​g/l sodium sulphate for dye 2, 20 ​g/l sodium carbonate at 70 ​°C for dye 1 and 80 ​°C for dye 2 and 60 ​min fixation time for both dyes. The two new reactive dyes exhibited higher dyeing properties and UPF values than the commercial reactive dye over all the dye concentrations studied. The new reactive dye 1 achieved the highest exhaustion, total fixation and UPF values. The fastness properties obtained for all the dyeings ranges from good to excellent.     

Anthraquinone and Azo Dyes in Dyeing Processes of PET Films and PET Knitted Fabrics Using Supercritical CO2 Medium

Summary: Dyeing processes using supercritical fluid present advantages over the conventional dyeing process using aqueous medium. Previous works from our group on polymeric fibers such as N,N-dimethylacrylamide (DMAAm) modified poly(ethylene terephthalate), PET, showed higher sorption of disperse dyes in supercritical medium. Furthermore, recent studies showed that the association of UV radiation and DMAAm treatment leads to a better incorporation of dyes in modified PET soaked in aqueous medium. In this work, modified and non-modified PET knitted fabrics (KF) were dyed in supercritical CO₂ medium. Azo and anthraquinone dyes were used in order to compare the extent of incorporated dye in PET films and PET KF in supercritical CO₂. The dyeing process variables were studied by factorial design and by a response surface methodology (RSM) technique. The anthraquinone dye presented a better incorporation in PET than the azo dye. The UV light exposure and the dyeing times inputs showed positive main effects in the incorporation of dyes in PET films and PET KF. From the RSM data, DMAAm and UV light modified PET KF presented 7.43 mg of incorporated azo dye by g of PET if the optimized dyeing conditions, time: 135 min and pressure: 212 bar would be used. In the respective optimized dyeing conditions for the anthraquinone dye, time 150 min and pressure 229 bar, the incorporated dye would be 22.9 mg of dye by g of PET.     

Stability of Dye Dispersions in the Presence of Various Surface Active Agents and Additives

Disperse dyes are hardly soluble in water. They are usually milled in the presence of large amounts of dispersing agents in the dye industry. The type and amount of these materials can affect the disperse ability of dyes in aqueous media. In this article, stability of prepared dye dispersions in the presence of various surface active agents and additives were investigated. In this respect, various dispersing agents such as Irgasol DAM, Asutol 644, Dispertane MF, and Irgasol P800 were used to prepare dye dispersions in milling stage. Furthermore, the formulations of dye dispersions were obtained by adding β-cyclodextrin, urea, and wetting agent. The dye dispersion quality was determined by its filtering property, turbidity, and centrifuging method. The obtained results proved the stability of dispersion containing of Irgasol DAM, wetting agent, and β-cyclodextrin as dispersing auxiliaries in dyeing process of disperse dye on polyester fabrics in high temperature method was the highest as compared to other dispersions. From the experimental results, it was found out that stability of prepared dispersions was improved by the presence of β-cyclodextrin. Also, utilization of β-cyclodextrin in formulations of dye dispersions caused to increasing of stability of dispersion in the dyeing of polyester fabrics.     

高效液相色谱-电喷雾串联质谱法快速分离鉴定纺织品中的9种致癌染料

采用高效液相色谱-电喷雾串联四极杆质谱(HPLC-ESI-MS/MS)在选择反应监测(SRM)模式下分离鉴定纺织品中禁用的9种致癌染料。用甲醇超声同时提取天然纤维和化学纤维上的染料,以5 mmol/L乙酸铵和乙腈为流动相在C18柱上于前段洗脱酸性红26、直接蓝6、直接黑38和直接红28(采用电喷雾质谱负离子模式检测),于后段洗脱碱性红9、碱性紫14、分散蓝1、分散橙11和分散黄3(采用电喷雾质谱正离子模式检测),实现了对不同种类纤维织品中分属4类性质不同染料的一次提取和一次分析检测。通过比较试样与标样的色谱保留时间和质谱图中子离子的相对丰度比,可准确鉴别纺织品中的致癌染料。     

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     

Dye fixation and decolourization of vinyl sulphone reactive dyes by using dicyanidiamide fixer in the presence of ferric chloride

A synthetic polymer was synthesized and used for the improvement of dyeing properties as well as decolorization of textile waste water. Two dyes were selected having anthraquinone based Remazol Blue R and azo based Remazol Red RB. It was observed that the synthetic polymer can be used as fixer for the fixation of dye by crosslinking between dye and fibre, which not only improves the dyeing properties but also helpful to coagulate the colour after dyeing. By single point method the concentrations of synthetic polymer were calculated in residual after dyeing. It was examined that the residual synthetic polymer is helpful in colour removal efficiency by coagulation of polymer with dye to form heavy molecules which settle down and decolorization occurred. Colour removal efficiency was found dependents on pH, concentration of synthetic polymer and inorganic coagulant.     

Dyeing of multiple types of fabrics with a single reactive azo disperse dye

Three novel reactive azo disperse dyes were prepared using 7-acetamide-4-hydroxy-2-naphthalene sodium sulphate as the precursor. The structure of the dyes has the combined characteristics of reactive, disperse, and cationic dyes. Under alkaline conditions (pH 9), the dyes can be applied to cotton, silk, wool, and nylon. Under neutral conditions, they can be used to dye polyester. Under acidic conditions (pH 4.5), they can colour acrylic fabric after conversion of the tertiary amine group to the quaternary ammonium cation. The colour-fastness of the dyed fabrics were also evaluated.     

Synthesis,characterization, and dyeing performance of some azo thienopyridine and thienopyrimidine dyes based on wool and nylon

A string of novel heterocyclic mono azo dyes were synthesized and their utilization in dyeing different fabrics as wool and nylon were discussed. Thienopyridine azo dyes 4 and 6 were prepared by reaction of chloro acetamidederivative 2 with diamino compounds to yield 3 and 5 , followed by reaction with NaNO₂/HCl and coupling with nucleophilic reagent. One-pot reaction of chloro acetamide 2 with ammonium thiocyanat in solvent ethanol gave the unexpected thienopyrimidine derivative 7 , which contain two active sites, the former is primary amine that was able to form diazonium salt that coupled with N,N-dimethylaniline, resorcinol, and/or self-coupling to afford the azo dyes 8-10 , and the latter is active methylene group that underwent coupling with different diazonium salts to give the azo thienopyrimidine derivative dye 11-15 . The dyeing performance of these azo dyes had been investigated in terms of their dyeing behavior and fastness properties on different fabrics. Results showed that the color strength (K/S) values, as well as, washing, rubbing, and resistance to acid, alkali and light showed high efficiency of these heterocyclic mono azo dyes to dye wool rather than nylon fibers.     

Surface modification by self-assembled polycation/azo dye multilayers

The formation and stability of some polycation/azo dye multilayers by the alternate adsorption of one polycation of integral type having 95 mol% of N,N-dimethyl-2-hydroxypropyleneammonium chloride repeat units (PCA₅) and four multicharged azo dyes: Crocein Scralet MOO (CSMOO), Ponceau SS (PSS), Direct Blue 1 (DB 1) and Direct Red 80 (DR 80) are discussed in this paper. The dyes were different either by the number of sulfonic groups (PSS, DB 1 and DR 80) or by their position (CSMOO and PSS). The multilayer growth, when PCA₅ was adsorbed from 0.2 M Na₂SO₄ aqueous solution, was followed by UV-Vis spectroscopy and by electrokinetic measurements. Solid state polycation/azo dye complexes were also prepared to get qualitative information on the charge compensation in the multilayers.     

Removal of Disperse Dyes from Water Using Surfactant Treated Alumina

An alumina surface was modified by adsorption of an anionic surfactant, sodium dodecyl sulfate (SDS). Typical S‐shaped isotherm of surfactant on alumina was observed. The adsorption of Disperse Red‐11, Disperse Blue‐26 and Disperse Red‐156 on alumina and surfactant treated alumina has been investigated. The enhancement in adsorption of these disperse dyes on surfactant treated alumina is observed, which may be attributed to their solubilization in surfactant aggregates formed at the solid/liquid interface. The effect of pH on adsorption has been studied. The adsorption is greatly influenced by pH of the medium. The applicability of the Langmuir model and the Dual‐Mode sorption model (DSM) were tested for equilibrium data.     

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.     

Synthesis,characterization, and properties of antibacterial dye based on chitosan

A new low-molecular-weight antibacterial dye was obtained by reaction of Reactive Blue 19 and chitosan previously hydrolyzed with H₂O₂. The compounds were characterized by Fourier-transform infrared spectroscopy, ¹³C solid-state nuclear magnetic resonance, X-ray photoelectron spectroscopy, X-ray diffraction analysis, and antibacterial, solubility, and dyeing performance tests including color difference and fastness. The results show that chitosan dyes were generated with covalent bonds between carbon and nitrogen atoms via reaction of alkene group of dye and primary amine group of chitosan. According to solubility tests, the solubility of the chitosan dye was controlled by the molecular weight of chitosan. In addition, compared with Reactive Blue 19, the antibacterial property of the chitosan dye was increased against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Besides, chitosan dye demonstrated better lightfastness and waterfastness than the original dye. Therefore, chitosan dye provides a new perspective for improving decorative and antimicrobial properties of wood products.