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。     

Triazine dye binding of human alpha-fetoprotein and albumin

Column chromatography was used to investigate the interaction of human alpha-fetoprotein and albumin with different immobilized dyes. Binding of alpha-fetoprotein to the dye conjugates was studied at pH 7.0. Between 56 and 93% of the total alpha-fetoprotein applied to the column was recovered in the break-through fractions of the respective runs. Of all the dyes, Cibacron Blue F3G-A adsorbs alpha-fetoprotein most strongly. This interaction clearly depends on the degree of dye substitution of the gel. A relatively weak interaction exists between alpha-fetoprotein and immobilized Procion Red HE-3B. This is used in the purification of alpha-fetoprotein by negative chromatography resulting in a 16.6-fold enrichment of this protein. Human albumin binds tightly to immobilized Cibacron Blue F3G-A as well as to Cibacron Brilliant Blue FBR-P and shows a lower affinity to Procion Blue MX-R. Procion Red dyes, which are structurally different from Cibacron Blue F3G-A are also capable of interacting with serum albumin. The results obtained are discussed in terms of the present theoretical conceptions about dye-protein interactions.     

A plant dye from Lawsonia inermis for protein staining after polyacrylamide gel electrophoresis.

A reddish-brown dye was isolated from the leaves of Lawsonia inermis by extraction with calcium hydroxide (pH 11-12). A 3.6% crude extract in ethanol/water, 1:1 v/v, was used for direct staining, without fixation, of bovine serum albumin, casein and human serum proteins, following polyacrylamide gel electrophoresis in cylindrical gels. After staining for 30 min the gels were destained for 1/2-2 h with 7% acetic acid at 60 degrees C. Protein staining with Amido Black 10B and Coomassie Brilliant Blue R-250, according to standard protocols, required destaining for 24 h and more to obtain a comparably cleared background. Staining with the plant dye and Coomassie Brilliant Blue had a similar overall staining sensitivity but some minor components of human serum showed different staining characteristics with each of the two dyes. Staining with the plant dye excels over standard staining by speed and simplicity.     

Comparison of Chemometric and Chromatographic Methods to Obtain Kinetic Parameters for Textile Dyes during a Biodegradation Process

The concentrations of three industrial-grade textile dyes were determined in a mixture after degradation by the fungus Ganoderma sp, by using the methods of UV-Vis spectrophotometry associated with Partial Least Squares regression and HPLC and comparing the results obtained from both methods. Using the concentrations calculated from the two methods, a kinetic study of the biodegradation mediated by the fungus was performed. The rate constants and the activation energies for this transformation were obtained for each dye in the mixture. The concentration of Remazol Blue R ESP could be determined by the HPLC method, and the value obtained was comparable with the result using the Partial Least Squares regression method. The Partial Least Squares regression method offers advantages over the HPLC method for the quantification of dyes in textile effluents, as it provides the kinetic parameters of the biodegradation reaction.     

In Silico and in Vitro Physicochemical Screening of Rigidoporus sp. Crude Laccase-assisted Decolorization of Synthetic Dyes—Approaches for a Cost-effective Enzyme-based Remediation Methodology

The objective of this paper is to compare in silico data with wet lab physicochemical properties of crude laccase enzyme isolated from Rigidoporus sp. using wheat bran as solid substrate support towards dye decolorization. Molecular docking analysis of selected nine textile and non-textile dyes were performed using laccase from Rigidoporus lignosus as reference protein. Enzyme-based remediation methodology using crude enzyme enriched from solid state fermentation was applied to screen the effect of four influencing variables such as pH, temperature, dye concentration, and incubation time toward dye decolorization. The extracellular crude enzyme decolorized 69.8 % Acid Blue 113, 45.07 % Reactive Blue 19, 36.61 % Reactive Orange 122, 30.55 % Acid Red 88, 24.59 % Direct Blue 14, 18.48 % Reactive Black B, 16.49 % Reactive Blue RGB, and 11.66 % Acid Blue 9 at 100 mg/l dye concentration at their optimal pH at room temperature under static and dark conditions after 1 h of incubation without addition of any externally added mediators. Our wet lab studies approach, barring other factors, validate in silico for screening and ranking textile dyes based on their proximity to the T1 site. We are reporting for the first time a combinatorial approach involving in silico methods and wet lab-based crude laccase-mediated dye decolorization without any external mediators.     

Reversible crosslinking in cellulose. VII. Memory effect of the crosslinking medium in the dyeing of crosslinked cotton

Cellulose β-mercaptoethylaminocarboxylate made from unmercerized cotton was partially oxidized in various solvents of different swelling power followed by treatment with excess methyl iodide to yield partially disulfide-crosslinked cotton samples of about the same degrees of crosslinking containing sulfonium groups of about the same contents. The effect of the solvent in crosslinking on the equilibrium and kinetics of dyeing with three dyes (Orange II, Direct Scarlet B, and Direct Sky Blue A) of different molecular size was investigated. The 1:1 ionic bonding was observed at equilibrium between sulfonic acid groups in dye molecules and sulfonium groups in modified cottons in cases of Orange II and Direct Scarlet B. The equilibrium uptake of the largest dye, Direct Sky Blue A, was much influenced by the solvent used in crosslinking; the higher the degree of swelling in crosslinking, the larger the equilibrium uptake. The diffusion rate of Direct Scarlet B was much affected by the solvent used; the higher the degree of swelling, the higher the diffusion rate. The pore structure of the crosslinked cotton was discussed. The crosslinked cotton seemed to have a “memory” of the state at the time of crosslinking and to have a tendency to come back close to that state when placed in a dye bath.     

Rapid spectrophotometric method to resolve ternary mixtures of Tartrazine, Quinoline Yellow and Patent Blue V in commercial products

A very simple spectrophotometric method is described for resolving ternary mixtures of the food dyes Tartrazine (E-102), Quinoline Yellow (E-104) and Patent Blue V (E-131) by using the second derivative of the spectra with measurements at zero-crossing wavelengths. Calibration graphs are linear up to 20.0 mg/L of Tartrazine, up to 20.0 mg/L of Quinoline Yellow and up to 6.4 mg/L of Patent Blue V. Repeatability and reproducibility studies (with the Students’s and F tests) were achieved for two series of nine standards for each dye showing no significant differences at the 95% confidence level. Detection limits of 0.0526, 0.0164 and 0.0034 mg/L were obtained for Tartrazine, Quinoline Yellow and Patent Blue V, respectively. This method was used for determining synthetic mixtures of these colorants in different ratios and it was successfully applied to four commercial products without previous separation step. The results found in commercial products were compared with those obtained by an HPLC method and very similar values were found for both methods. Received: 28 December / Revised: 26 May 1999 / Accepted: 31 May 1999     

Solid-phase extraction and simultaneous determination of trace amounts of sulphonated and azo sulphonated dyes using microemulsion-modified-zeolite and multivariate calibration

A simple and rapid analytical method for the determination of trace levels of five sulphonated and azo sulphonated reactive dyes: Cibacron Reactive Blue 2 (C-Blue, trisulphonated dye), Cibacron Reactive Red 4 (C-Red, tetrasulphonated azo dye), Cibacron Reactive Yellow 2 (C-Yellow, trisulphonated azo dye), Levafix Brilliant Red E-4BA (L-Red, trisulphonated dye), and Levafix Brilliant Blue E-4BA (L-Blue, disulphonated dye) in water is presented. Initially, the dyes were preconcentrated from 250 ml of water samples with solid-phase extraction using natural zeolite sample previously modified with a microemulsion. The modified zeolite exhibited an excellent extraction for the dyes from solution. The parameters that influence quantitative recovery of reactive dyes like amount of extractant, volume of dye solution, pH, ionic strength, and extraction-elution flow rate were varied and optimized. After elution of the adsorbed dyes, the concentration of dyes was determined spectrophotometrically with the aid of principle component regression (PCR) method without separation of dyes. The results obtained from PCR method were comparable to those obtained from HPLC method confirming the effectiveness of the proposed method. With the aid of SPE by M-zeolite, the concentration of dyes could be reproducibly detected over the range 25-200 ppb for C-Yellow and L-Blue and from 50 to 250 ppb for C-Blue, C-Red, and L-Red. The multivariate detection limits of dyes were found to be 15 ppb for C-Yellow and L-Blue and 25 ppb for C-Blue, C-Red, and L-Red dyes. The proposed chemometric method gave recoveries from 85.4 to 115.3% and R.S.D. from 1.0 to 14.5% for determination of the five dyes without any prior separation for solutes.     

Dynamics of nonionic surfactant-rich phase separation and recovery of dyes

Cloud point separation of selected dyes was studied. The use of dyes made possible observation of the dynamics of surfactant-rich phase separation by color video. The pictures were interpreted by means of ImageC software and degrees of whiteness were calculated. It was found that separation was slow and equilibrium was not achieved even after a period of more than 10 h. The separated surfactant-rich phase had a heterogeneous structure. The globules of the surfactant-rich phase were also observed in the micellar aqueous phase. The surfactant concentration could be as high as one or two orders of magnitude above the expected cmc values and was not decreased to critical micelle concentration by centrifugation. The presence of sodium chloride was important and improved separation. Separation of dyes was in the range 73-98% and depended upon the surfactant, the temperature, the electrolyte content, and the dye. In each system considered, appropriate conditions had to be selected to obtain high recovery of the dye. The presence of the electrolyte was the most important parameter and it improved the separation of dyes. However, addition of the electrolyte could also account for precipitation of the dyes, as observed for the systems containing Direct Pink. The best recoveries were observed for Direct Yellow and oxyethylated nonylphenol (98% at 55 degrees C in the presence of NaCl). Centrifugation gave recoveries similar to those for prolonged heating but it shortened the time of phase separation.     

Macro-Reticular Ion Exchange Resins for Recovery of Direct Dyes from Spent Dyeing and Soaping Liquors

Dyes are a major class of organic pollutants that are well-known for their harmful impact on aquatic life and humans. Several new strategies for removing colours from industrial and residential effluents have recently emerged, with adsorption being the best option. The current study looked at the recovery of direct dyes from aqueous streams for reuse using macro-reticular ion exchange resins (IERs). The investigation includes dyeing single jersey cotton grey textiles with direct dyes from the Isma dye Company in Kafr El Dawar, Egypt. After centrifuging and separating the supernatant liquid, solutions from thirteen different dyes, produced at an average concentration between the wasted and soaping liquor concentrations, were calculated spectrophotometrically from the first dyeing trials. Kinetic data were well fitted with pseudo-second-order rate kinetics. The amounts of dye retained by the anion exchangers increased with a rise in temperature in the case of Strong Base Resin (SBR) and vice versa for Weak Base Resin (WBR). Batch adsorption experiments with SBR and WBR were conducted for each dye, and both Freundlich and Langmuir isotherms were constructed. It was found that adsorption obeyed both isotherms, that monolayer adsorption took place, and that the dye molecular weight, structure, and solubility, as well as the type of anionic resin used, had varying effects on the extent of absorption. The monolayer sorption capacities Q₀ determined from the Langmuir isotherm model for the strongly and weakly basic anion exchangers were found to be 537.6 and 692 mg/g for Direct Yellow RL, respectively. As a result, Yellow RL exhibited the greatest adsorption on both SBR and WBR. Orange GRLL, Blue 3B, and Congo Red, on the other hand, were the poorest colours absorbed by the IERs, whereas Blue RL demonstrated good adsorption by SBR and accelerated adsorption by WBR. Most of the dyes may be recovered and reused in this manner.     

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.     

Investigation of near-infrared laser dye albumin complexes

Near-infrared (NIR) spectroscopy is used to investigate the properties of the NIR laser dye albumin complexes. The binding sites on albumins are probed using four structurally very similar NIR laser dyes, the DTTCI, DOTCI, DTDCI and DODCI. The pronounced differences observed in the NIR spectra of these dyes indicate that specific binding may occur since differences in the microenvironment of the binding area does not alone explain these changes. The DTTCI complexes with albumins showed a significant decrease in the NIR absorption while the other three dyes did not. These results suggest that the presence of the S heteroatoms as well as their distance from each other are determining factors in the observed specific binding. Dissimilarities in the NIR spectra of different albumin complexes indicate a difference in the structure of the microenvironment surrounding the NIR laser dye binding sites.     

An evaluation of the dyeing behavior of sol–gel silica doped with direct dyes

A new dyeing process of sol–gel silica doped with direct dyes is investigated for improving color strength (K/S value) and dyeing fastness. Cotton fabrics are dyed in this direct dye silica solution. The results indicate that the K/S value of C.I. Direct Blue 86 and C.I. Direct Red 23 are enhanced by 12.8% and 16.8%, respectively. For C.I. Direct Blue 86, the washing staining fastness is improved by half a grade, and the rubbing fastness and the washing change fastness are enhanced by one grade, respectively. Compared to the fabric fixed with fixing reagent MMF-1, the K/S value is improved by about 23.7% and the wet rubbing fastness and washing change fastness are enhanced by half a grade. The formation of uniform continuous layers on the fiber surface dyed with direct dye silica solution is revealed by video microscope, and the calculated sol–gel weight gain on the fabric is 4.6%.     

Degradation of textile dyes mediated by plant peroxidases

The peroxidase enzyme from the plants Ipomea palmata (1.003 IU/g of leaf) and Saccharum spontaneum (3.6 IU/g of leaf) can be used as an alternative to the commercial source of horseradish and soybean peroxidase enzyme for the decolorization of textile dyes, mainly azo dyes. Eight textiles dyes currently used by the industry and seven other dyes were selected for decolorization studies at 25–200 mg/L levels using these plant enzymes. The enzymes were purified prior to use by ammonium sulfate precipitation, and ion exchange and gel permeation chromatographic techniques. Peroxidase of S. spontaneum leaf (specific activity of 0.23 IU/mg) could completely degrade Supranol Green and Procion Green HE-4BD (100%) dyes within 1 h, whereas Direct Blue, Procion Brilliant Blue H-7G and Chrysoidine were degraded >70% in 1 h. Peroxidase of Ipomea (I. palmata leaf; specific activity of 0.827 U/mg) degraded 50 mg/L of the dyes Methyl Orange (26%), Crystal Violet (36%), and Supranol Green (68%) in 2–4 h and Brilliant Green 54%), Direct Blue (15%), and Chrysoidine (44%) at the 25 mg/L level in 1 to 2 h of treatment. The Saccharum peroxidase was immobilized on a hydrophobic matrix. Four textile dyes, Procion Navy Blue HER, Procion Brilliant Blue H-7G, Procion Green HE-4BD, and Supranol Green, at an initial concentration of 50 mg/L were completely degraded within 8 h by the enzyme immobilized on the modified polyethylene matrix. The immobilized enzyme was used in a batch reactor for the degradation of Procion Green HE-4BD and the reusability was studied for 15 cycles, and the halflife was found to be 60 h.     

Comparison of dye (oxazine and thiazine) materials as a photosensitizer for use in photogalvanic cells based on molecular interaction with sodium dodecyl sulphate by spectral study

The photochemistry of dye is playing a significant role for understanding the mechanism of electron transfer reactions in photoelectrochemical devices such as photogalvanic cells, DSSC, semiconductor photo-catalysis, photoconductors, etc. Oxazines (Brilliant Cresyl Blue and Nile Blue O) and thiazines (Azur A, Azur B, Azur C, Methylene Blue and Toluidine Blue O) dyes have been used widely as a photosensitizer with and without surfactants in the photogalvanic cells for solar power conversion and storage. Since, the stability and solubility of photosensitizers (dyes) are increased in the presence of surfactant and these properties lead to enhance the electrical output of the photogalvanic cells. Therefore, here we have studied the extent of interaction of different dyes with sodium dodecyl sulphate (SDS), find out the order of stability of dye–SDS on the basis of magnitudes of shifting in λ_max of dye monomer and try to correlate order of dye–SDS interaction with already reported electrical output data of photogalvanic cells. Brilliant Cresyl Blue, Nile Blue O, Azur A and TB O have shown red shifting while Azur B, Azur C and MB have shown blue shifting in their λ_max value with SDS, which indicates formation of dye–surfactant complex. But, the extent of formation of complex for different dyes with SDS was different due to change in their alkyl groups. Dyes with red shifting have greater stability in excited state as well as higher electrical output data of the cell than dye with blue shifting. On the basis of both red and blue shifting, order of stability of dyes–SDS complex was found as: Brilliant Cresyl Blue?>?Toluidine Blue O?>?Azur A?>?Nile Blue?>?Azur B?>?Methylene Blue?>?Azur C. The order of electrical output values of these dyes in photogalvanic cells have also been supported by literature data in the presence of SDS. Hence, the dye–surfactant complex which would have greater stability in excited state might be more useful for improvement of conversion efficiency and storage capacity of photogalvanic cells in the future.     

Silicone nanomicelle dyeing method on polyester fibre: Comparative evaluation of chemical properties,fastness properties,and DFT

Disperse Red 177(9a), Disperse Red 343(9b), Disperse Blue 165(9c), Disperse Blue 165.1(9d), Disperse Blue 366(9e), and Disperse Blue 148(9f) were examined in the solvent. During silicon nanomicelle dyeing, we employed 9(a–f) azo disperse dyes on polyester. On polyester fabric, dye 9(a–f) offers equal washing, light, and rubbing fastness in both the conventional and silicone nanomicelle techniques. The dye can now be transported directly into the fibre core without the use of auxiliary dyes owing to the reduction in the particle size of azo dyes, which is made possible by nanoemulsions superior dispersion. The levelling property of the dispersed dye is enhanced by the dyeing process. When both techniques are applied, the lightfastness properties of all dyes are improved. It provides a very good to outstanding protection factor for textile materials. These 9(a–f) azo disperse dyes have moderate to outstanding photostability, net electrophilicity index, and lightfastness.     

Use of intercalated clays in oxidation of organic dyes

Intercalated materials based on natural montmorillonite and Fe- and mixed Fe/Al-polyhydroxo complex were obtained and their texture properties were studied. The catalytic properties of these materials were examined in the reaction of oxidation of an organic dye, Direct Pure Blue, with hydrogen peroxide in aqueous solutions. The optimal conditions of oxidation of azo dyes in the presence of intercalated clays were determined. In these conditions, a 100% oxidation of dye solutions can be achieved, with the stability of catalysts preserved.     

Why do Congo Red,Evans Blue,and Trypan Blue differ in their complexation properties?

Congo Red, Evans Blue, and Trypan Blue dyes were evaluated in terms of their ability to form supramolecular systems in water solution. A geometric transformation set was defined to construct a supramolecular model system composed of eight dye molecules. The stability of the constructed multimolecular systems was estimated by molecular dynamics using AMBER 4.1 and DISCOVER force fields. The results essentially confirm the tendency toward self‐assembly in each case. However, Congo Red and Evans Blue were found to form stable, continuous, ribbon‐like supramolecular organizations, whereas Trypan Blue self‐assembly appeared defective; some additional deviations from planarity seem to be the main reason for the disturbance in self‐assembling. The extra rotation around the azo bonds in the Trypan Blue molecule is slightly extorted by the close proximity of sulfonic groups. This may also be the direct cause of the observed deviation from symmetry in the molecule of this dye. The results confirm that the self‐assembling capability of the compounds studied correlates with the capacity to complex proteins, supporting the idea that supramolecularity may create specific ligation properties. © 2000 John Wiley & Sons, Inc. J Comput Chem 21: 656–667, 2000     

Rapid spectrophotometric method to resolve ternary mixtures of Tartrazine, Quinoline Yellow and Patent Blue V in commercial products

A very simple spectrophotometric method is described for resolving ternary mixtures of the food dyes Tartrazine (E-102), Quinoline Yellow (E-104) and Patent Blue V (E-131) by using the second derivative of the spectra with measurements at zero-crossing wavelengths. Calibration graphs are linear up to 20.0 mg/L of Tartrazine, up to 20.0 mg/L of Quinoline Yellow and up to 6.4 mg/L of Patent Blue V. Repeatability and reproducibility studies (with the Students’s and F tests) were achieved for two series of nine standards for each dye showing no significant differences at the 95% confidence level. Detection limits of 0.0526, 0.0164 and 0.0034 mg/L were obtained for Tartrazine, Quinoline Yellow and Patent Blue V, respectively. This method was used for determining synthetic mixtures of these colorants in different ratios and it was successfully applied to four commercial products without previous separation step. The results found in commercial products were compared with those obtained by an HPLC method and very similar values were found for both methods.     

Spectrophotometric Determination of Polyacrylamide in Aqueous Solutions Using Cationic Dyes

Spectrophotometry was used to study the interaction of high-molecular polyacrylamide with cationic dyes: Methylene Blue, Acridine Yellow, and Toluidine Blue. Polyacrylamide samples were modified by alkaline hydrolysis. The optimum conditions of the formation of polyacrylamide–cationic dye adducts and their compositions were found. Simple procedures are proposed for the determination of the polymer. The relative standard deviation of the results of the determination of polyacrylamide in aqueous solutions is no higher than 6%.