Novel Disperse Dyes Based on Enaminones: Synthesis, Dyeing Performance on Polyester Fabrics, and Potential Biological Activities.

1-(3-aryl)-3-(dimethylamino)prop-2-en-1-one (enaminones) derivatives and the diazonium salt of para-chloroaniline were used to synthesize several novel disperse azo dyes with high yield and the use of an environmentally friendly approach. At 100 and 130 °C, we dyed polyester fabrics using the new synthesized disperse dyes. At various temperatures, the dyed fabrics' color intensity was assessed. The results we obtained showed that dyeing utilizing a high temperature method at 130 °C was enhanced than dyeing utilizing a low temperature method at 100 °C. Reusing dye baths once or twice was a way to achieve two goals at the same time. The first was obtaining a dyed product at no cost, and the second was a way to treat the wastewater of dyeing bath effluents and reuse it again. Good results were obtained for the fastness characteristics of polyester dyed with disperse dyes. When the disperse dyes were tested against certain types of microbes and cancer cells, they demonstrated good and encouraging findings for the potential to be used as antioxidants and antimicrobial agents.

A Holistic Review of 3-Dimethylamino-1-Arylpropenones Based Disperse Dyes for Dyeing Polyester Fabrics: Synthesis, Characterization, and Antimicrobial Activities.

The enaminone compounds 3-Dimethylamino-1-arylpropenones produced in this review was synthesized by reacting para-methylacetophenone and para-nitroacetophenone with dimethylformamide dimethyl acetal. In this review article, we discuss how to create novel disperse colors by reacting enaminone derivatives 3a and 3b with phenyldiazonium salt. The highly productive procedure of creating new disperse dyes was followed by the process of dyeing polyester fabrics at temperatures between 70 and 130 °C. As a result, the colours' resistance to light, rubbing, perspiration, and washing fastness was assessed. In an effort to show the additional value of these dyes, the expected biological activity of the synthetic dyes against fungus, yeast, and Gram-positive and Gram-negative bacteria was also assessed. We have applied zinc oxide nanoparticles for polyester fabrics treatment to impact them a self-cleaning quality, increase their light fastness, enhance their antibacterial efficacy, and enhance UV protection as part of our ongoing strategy to obtain polyester fabrics with newly acquired specifications.

Sensitization to textile dyes in Spain: Epidemiological situation (2019-2022).

BACKGROUND: Current frequency and features for positivity to textile dye mix (TDM) in Spain are unknown. OBJECTIVES: To study the frequency, clinical features and simultaneous positivity between TDM, para-phenylenediamine (PPD) and specific disperse dyes. MATERIALS AND METHODS: We analysed all consecutive patients patch-tested with TDM from the Spanish Contact Dermatitis Registry (REIDAC), from 1 January 2019 to 31 December 2022. Within this group, we studied all selected patients patch-tested with a textile dye series. RESULTS: Out of 6128 patients analysed, 3.3% were positive to the TDM and in 34% of them, the sensitization was considered currently relevant. TDM positivity was associated with working as a hairdresser/beautician and scalp, neck/trunk and arm/forearm dermatitis. From TDM-positive patients, 57% were positive to PPD. One hundred and sixty-four patients were patch-tested with the textile dye series. Disperse Orange 3 was the most frequent positive dye (16%). One of every six cases positive to any dye from the textile dye series would have been missed if patch-tested with the TDM alone. CONCLUSIONS: Positivity to TDM is common in Spain and often associated with PPD sensitization. TDM is a valuable marker of disperse dyes allergy that should be part of the Spanish and European standard series.

Investigating sensitization activity of azobenzene disperse dyes via the Direct Peptide Reactivity Assay (DPRA).

Azobenzene disperse dyes are the fastest-growing category of commercial dyestuffs and have been found in indoor house dust and in children's polyester apparel. Azobenzene disperse dyes are implicated as potentially allergenic; however, little experimental data is available on allergenicity of these dyes. Here, we examine the binding of azobenzene disperse dyes to nucleophilic peptide residues as a proxy for their potential reactivity as electrophilic allergenic sensitizers. The Direct Peptide Reactivity Assay (DPRA) was utilized via both a spectrophotometric method and a high-performance liquid chromatography (HPLC) method. We tested dyes purified from commercial dyestuffs as well as several known transformation products. All dyes were found to react with nucleophilic peptides in a dose-dependent manner with pseudo-first order kinetics (rate constants as high as 0.04 h-1). Rates of binding reactivity were also found to correlate to electrophilic properties of dyes as measured by Hammett constants and electrophilicity indices. Reactivities of polyester shirt extracts were also tested for DPRA activity and the shirt extracts with high measured abundances of azobenzene disperse dyes were observed to induce greater peptide reactivity. Results suggest that azobenzene disperse dyes may function as immune sensitizers, and that clothing containing these dyes may pose risks for skin sensitization.

Characterizing azobenzene disperse dyes and related compounds in house dust and their correlations with other organic contaminant classes.

Azobenzene disperse dyes are the fastest-growing category of commercial dyestuffs and are implicated in the literature as potentially allergenic. In the indoor environment, these dyes may be shed from various textiles, including clothing and upholstery and accumulate in dust particles potentially leading to exposure in young children who have higher exposure to chemicals associated with dust due to their crawling and mouthing behaviors. Children may be more vulnerable to dye exposure due to their developing immune systems, and therefore, it is critical to characterize azobenzene disperse dyes in children's home environments. Here, we investigate azobenzene disperse dyes and related compounds in house dust samples (n = 124) that were previously analyzed for flame retardants, phthalates, pesticides and per- and polyfluoroalkyl substances (PFAS). High-resolution mass spectrometry was used to support both targeted and suspect screening of dyes in dust. Statistical analyses were conducted to determine if dye concentrations were related to demographic information. Detection frequencies for 12 target dyes ranged from 11% to 89%; of the dyes that were detected in at least 50% of the samples, geometric mean levels ranged from 32.4 to 360 ng/g. Suspect screening analysis identified eight additional high-abundance azobenzene compounds in dust. Some dyes were correlated to numerous flame retardants and several antimicrobials, and statistically higher levels of some dyes were observed in homes of non-Hispanic Black mothers than in homes of non-Hispanic white mothers. To our knowledge, this is the most comprehensive study of azobenzene disperse dyes in house dust to date. Future studies are needed to quantify additional dyes in dust and to examine exposure pathways of dyes in indoor environments where children are concerned.

Reductive metabolism of azo dyes and drugs: Toxicological implications.

Azo compounds are widely distributed synthetic chemicals in the modern world. Their most important applications are as dyes, but, in addition, several azo compounds are used as pharmaceuticals. Ingested azo compounds can be reduced by the action of bacteria in the gut, where the oxygen tension is low, and the development of microbiome science has allowed more precise delineation of the roles of specific bacteria in these processes. Reduction of the azo bond of an azo compound generates two distinct classes of aromatic amine metabolites: the starting material that was used in the synthesis of the azo compound and a product which is formed de novo by metabolism. Reductive metabolism of azo compounds can have toxic consequences, because many aromatic amines are toxic/genotoxic. In this review, we discuss aspects of the development and application of azo compounds in industry and medicine. Current understanding of the toxicology of azo compounds and their metabolites is illustrated with four specific examples - Disperse Dyes used for dyeing textiles; the drugs phenazopyridine and eltrombopag; and the ubiquitous food dye, tartrazine - and knowledge gaps are identified. SUBMISSION TO: FCT VSI: Toxicology of Dyes.

Synthesis of New Monoazo Disperse Dyes for Dyeing Polyester Fabric Using Two Different Dyeing Methods: Demonstration of Their Antibacterial and Anticancer Activities.

3-(dimethylamino)-1-phenylprop-2-en-1-ones were obtained with good yields by reacting dimethylformamide dimethylacetal with different methyl ketones. 3-oxo-3-phenyl-2-(2-phenylhydrazono)propanals disperse dyes were obtained via reacting of 3-(dimethylamino)-1-phenylprop-2-en-1-ones with phenyldiazonium chloride. The novel dyes were used in dyeing polyester fabrics through two different dyeing methods at temperatures of 100 and 130 °C. We found that the color strength when using the dyeing method at 130 °C was better than the dyeing method at 100 °C. The fastness properties of dyed fabrics with these new disperse dyes were studied and gave very good results (except for fastness to light, which gave moderate results). The new dyes were evaluated against some different types of bacteria and cancer, which showed excellent and promising results for the possibility of using these dyes as antibacterial and anticancer agents.

Can Novel Synthetic Disperse Dyes for Polyester Fabric Dyeing Provide Added Value?

In this review, we present preparation methods for a series of new disperse dyes that we have synthesized over the past thirteen years in an environmentally safe and economical way using innovative methods, conventional methods, or using microwave technology as a safe and uniform method of heating. The results showed that in many of the synthetic reactions we carried out, the use of the microwave strategy provides us with the product in minutes and with higher productivity compared to the conventional methods. This strategy provides or may dispense with the use of harmful organic solvents. As an environmentally friendly approach, we used microwave technology in dyeing polyester fabrics at 130 degrees Celsius, and then, we also introduced ultrasound technology in dyeing polyester fabrics at 80 degrees Celsius as an alternative to dyeing methods at the boiling point of water. Here, the goal was not only to save energy, but also to obtain a color depth higher than the color depth that can be obtained by traditional dyeing methods. It is worth noting that obtaining a higher color depth and using less energy means that the amount of dye remaining in the dyeing bath is less, which facilitates the processing of dyeing baths and therefore does not cause harm to the environment. It is necessary after obtaining dyed polyester fabrics to show their fastness properties, so we explained that these dyes have high fastness properties. The next thought was to use nano-metal oxides to treat polyester fabrics in order to provide these fabrics with important properties. Therefore, we present the strategy for treating polyester fabrics with titanium dioxide nano-particles (TiO2 NPs) or zinc oxide nano-particles (ZnO NPs) in order to enhance their anti-microbial properties, increase their UV protection, increase their light fastness, and enhance their self-cleaning properties. We reviewed the biological activity of all of the newly prepared dyes and showed that most of these dyes possess strong biological activity.

Preparation of nano disperse dyes using sulfomethylated lignin: Effects of sulfonic group contents.

The molecular simulation software was firstly applied to analyze the adsorption of sulfomethylated lignin (SAL) on dye surfaces. Then, SALs with different sulfonic group contents were prepared and characterized by FTIR, NMR, EA and GPC measurements using alkali lignin (AL) as raw materials and sodium sulfite as sulfonating agents. Next, SAL1.53 was determined to the optimum dispersant by TSI, particle size and thermal storage stability measurements, which had the smallest particle size of 173 nm and highest stability, comparable to the commercial Reax 85A lignin dispersant and basically satisfying the requirement of nano disperse dyes used in the digital printing technology. QCM, AFM and zeta potential results indicated that as the sulfonic group content of SAL increased, the adsorption mass, rigidity of the adsorbed layer, adsorption force and absolute zeta potential value all showed a gradually increasing tendency due to an enhanced hydrophilicity, and thus a decreased intermolecular agglomeration and an increased molecular chain stretching degree. A maximum was observed for SAL1.53. This research not only provided a novel approach to the preparation of high-performance lignin dispersants for nano disperse dyes, but also would broaden the high value-added industrial applications of biomass lignin into the digital printing and dyeing field.

Determination of disperse dyes on polyester fibers by UHPLC-Orbitrap MS.

The determination of fiber dyes is important in forensic investigations. Although a variety of fiber dyes detection methods have been established, the sensitive and accurate determination of trace fiber dyes remains a challenge due to the possible interferences caused by complex environmental matrix and various fiber additives. Orbitrap mass spectrometry (Orbitrap MS) is a type of high-resolution mass spectrometry with high qualitative accuracy and detection sensitivity which highly meet the identification requirements of fiber dyes in real cases. However, the application of Orbitrap MS in fiber dye analysis is limited. In this regard, this study used polyester fiber, which is the most commonly-found fiber in forensic cases, as a model and established a UHPLC-Orbitrap MS method to analyze disperse dyes on polyester fibers. Using the optimized UHPLC-Orbitrap MS method, nine disperse dyes were accurately identified and well separated, and the limits of detection ranged between 0.1 ng/mL and 5.0 ng/mL. The developed method was applied to analyze actual fiber samples, and dyes from single fibers of 1 mm in length could be accurately detected. The established method is sensitive, accurate, and demonstrates good application prospects.

Exclusion of Disperse Orange 3 is possible from the textile dye mix present in the Swedish baseline patch test series. A study by the Swedish Contact Dermatitis Research Group.

BACKGROUND: The textile dye mix (TDM) 6.6% in petrolatum contains Disperse Blue (DB) 35, Disperse Yellow 3, Disperse Orange (DO) 1 and 3, Disperse Red 1 and 17, and DB 106 and 124. The most frequent allergen in TDM-positive patients is DO 3. Around 85% of para-phenylenediamine (PPD)-allergic dermatitis patients have been positive to DO 3. There has been a discussion to exclude DO 3 from TDM 6.6% because of strong simultaneous reactions to TDM and PPD. OBJECTIVES: To study if DO 3 can be excluded from TDM 6.6%. METHODS: Patch tests were performed on 1481 dermatitis patients with TDM 6.6%, TDM 7.0% (without DO 3 but the other disperse dyes at 1.0% each), DO 3 1.0%, and PPD 1.0% pet. RESULTS: Contact allergy to TDM 6.6% was 3.6% and to TDM 7.0% was 3.0%. All 26 DO 3-positive patients were positive to PPD. The 44 patients positive to TDM 7.0% plus the 13 positive to PPD and TDM 6.6% but negative to TDM 7.0% were 57, outnumbering the 53 positive to TDM 6.6%. CONCLUSION: TDM 7.0% can replace TDM 6.6% in the Swedish baseline series, since TDM 7.0% together with PPD 1.0% will detect patients with textile dye allergy.

Preparation of polyether amine-bridged lignosulfonate for utilization as a nano dye dispersant.

The long-term stability of nano disperse dye slurry is a problem in industry. In this work, high molecular-weight polyether amine-bridged lignosulfonates (PEABLs) were prepared to improve the adsorption strength of dispersants on dye surfaces, and thus the stability of nano disperse dyes. Specifically, the molecular simulation software was firstly used to analyze the adsorption of PEABL on dye surfaces. Then, PEABLs with different molecular weights were synthesized and characterized by adjusting the addition of polyether amine. Next, nano disperse dyes were prepared using PEABLs and the optimum grinding conditions were explored and obtained. Finally, PEABL3 was determined to the optimum dispersant, having a smallest particle size (168 nm) and highest stability, comparable to the commercial Reax 85A dispersant and basically satisfying the demand of nano disperse dyes required in digital transfer printing technology. Quartz crystal microbalance (QCM), atomic force microscopy (AFM) and zeta potential results showed as the molecular weight of PEABL increased, the adsorption amount, adsorbed layer rigidity, adsorption force and absolute zeta potential value all firstly increased due to the enhanced hydrophobic interaction, and then decreased due to the formation of complicated three-dimensional network structures caused by the crosslink of lignosulfonate molecules. A maximum was observed for PEABL3.

Development of the Microemulsion Electrokinetic Capillary Chromatography Method for the Analysis of Disperse Dyes Extracted from Polyester Fibers.

The study aimed to develop a method for the separation of dispersed dyes extracted from polyester fibers. Nine commercially available disperse dyes, which were used to dye three polyester fabrics, were tested. Extraction of dyes from 1 cm long threads was carried out in chlorobenzene at 100 °C for 6 h. The separation was performed using microemulsion electrokinetic capillary chromatography (MEEKC) with photodiode array detection. Microemulsion based on a borate buffer with an organic phase of n-octane and butanol and a mixture of surfactants, sodium dodecyl sulphate and sodium cholate, were used. The addition of isopropanol and cyclodextrins to microemulsion resulted in a notable improvement in resolution and selectivity. The content of additives was optimized by using the Doehlert experimental design. Values of the coefficient of variance obtained in the validation process, illustrating the repeatability and intermediate precision of the migration times fit in the range of 0.11-1.24% and 0.58-3.21%, respectively. The developed method was also successfully applied to the differentiation of 28 real samples-polyester threads collected from clothing. The obtained results confirmed that proposed method may be used in the discriminant analysis of polyesters dying by disperse dyes and is promisingly employable in forensic practice.

Facile Synthesis of Novel Disperse Dyes for Dyeing Polyester Fabrics: Demonstrating Their Potential Biological Activities.

Original work showed the composition of the dyes and the antimicrobial/UV protective properties of a series of dyes obtained in our laboratories over the past twelve years in an easy way using microwave technology and their comparisons with conventional methods. The results we obtained clearly indicated that by using the microwave strategy, we were able to synthesize the new disperse dyes in minutes and with a much higher productivity when compared to the traditional methods, which took a much longer time, sometimes up to hours. We also introduced ultrasonic technology in dyeing polyester fabrics at 80 °C for an environmentally friendly approach, which was an alternative to traditional dyeing methods at 100 °C; we obtained a much higher color depth than traditional dyeing methods reaching 102.9%. We presented both the biological activity of the prepared new dyes and the fastness properties and clearly indicated that these dyes possess biological activity and high fastness properties.We presented through the results that when dyeing polyester fabrics with some selected disperse dyes, the color strength of polyester fabrics dyed at high temperatures was greater than the color strength of polyester fabrics dyed at low temperatures by 144%, 186%, 265% and 309%. Finally, we presented that a ZnO or TiO2 NPs post-dyeing treatment of polyester fabrics is promising strategy for producing polyester fabrics possess multifunction like self-cleaning property, high light fastness, antimicrobial and anti-ultraviolet properties.

The characterization of disperse dyes in polyester fibers using DART mass spectrometry.

Textile fibers alone are highly prevalent in our environment, and not only are there a wide variety of fibers, but generally, consumer textiles are colored. Given the variety of crime locations where dyes are encountered and the potential circumstances, a rapid, preparation free analysis of samples is highly beneficial. This study has characterized a collection of commercially available textiles dyes by verifying the chemical structure, collecting reference spectra, and developing a method to analyze dyed fibers via Direct Analysis in Real-Time (DART) mass spectrometry. A methodology for direct analysis of pieces of fabric and single thread samples of polyester fibers dyed with disperse dyes was developed. The presence of 31 target dyes on fibers whose structures were previously established via high-resolution mass spectrometry was confirmed. Dyed fabrics containing mixtures of dyes in varying concentrations were also evaluated to determine whether each dye in the composition could be detected. The DART-MS methodology was sensitive and positively characterized disperse dyes in polyester fibers, allowing for blind identification of mixtures with the assistance of a high-resolution mass spectrometry database.

Patch test results to extracts of synthetic garments in textile dye positive patients.

BACKGROUND: Disperse dyes (DDs) are the most prevalent causes of textile-related allergic contact dermatitis and are used for colouring synthetic textile materials based on fibres such as polyester, acrylic, acetate and polyamide. Eight DDs are included in a textile dye mix (TDM) 6.6% petrolatum (pet.) in the European baseline patch test series. OBJECTIVES: The aim of this study was to patch test TDM 6.6% pet. positive individuals with the extracts of synthetic fibre clothes that do not contain any of the pure DDs present in the TDM 6.6% to study the reactivity pattern. METHODS: Seventy-three TDM-positive former patients tested between 2012 and 2017 at the Department of Occupational and Environmental Dermatology in Malmö, Sweden were invited to join the study, 10 participated. Twenty-four textile items (collected in nine countries in Europe, Asia and North America in 2012) were extracted in dichloromethane. The TDM 6.6% was patch tested simultaneously with the 24 textile item preparations in petrolatum made from the extracts. Prior to patch testing the participants filled the 7-question questionnaire regarding possible symptoms from textile exposure. RESULTS: Ten individuals, agreed to join the study. Eight of them reacted to TDM 6.6%. Nine participants reacted to 20 of 24 extracts. One reacted to 19 extracts, another to 14, 3 to 5 extracts, 1 to 4, 1 to 3 extracts and 2 to 2 extracts. One was negative to all tested preparations including TDM 6.6%. The participants mainly reacted to six textile extracts. All controls tested negatively to tested extracts. Four individuals of the 10 TDM-allergic individuals previously had had problems after wearing clothes. Four out of the 10 participants had had atopic eczema in childhood. All women had dyed their hair with permanent hair dyes but none of the males. CONCLUSION: TDM-positive patients react to textile extracts made from synthetic garments, even if they do not contain any of the pure DDs present in TDM 6.6%. More studies are needed to pin-point the culprit haptens in these extracts.

Microwave-Assisted Synthesis of Azo Disperse Dyes for Dyeing Polyester Fabrics: Our Contributions over the Past Decade.

Organic reactions utilizing the microwave strategy have become able to conduct in shorter times, with higher yields, and are compatible with green chemistry protocols. In recent years, microwave technologies as an effective agent in organic synthesis have been successful utilized in textile industries and for the synthesis of dyes, especially disperse dyes. Herein, we present our contributions over the past decade through the use of microwave technology not only in the synthesis of new biologically active organic compounds and disperse dyes, but also the use of this effective, environmentally friendly technology in dyeing polyester fabrics as an alternative to conventional heating methods. We also demonstrate both the fastness properties and biological activities of the newly prepared compounds. In addition, we present the treatment of dyeing baths by reusing them again in the dyeing process, using microwave energy to achieve this goal, and this has environmentally friendly dimensions. Some of the possible utilizations of microwave irradiation have been presented in many different fields of chemistry. We recommend relying on this effective and environmentally safe technology instead of relying on conventional methods that take a lot of time, give low yields, and may have a negative impact on the environment.

Innovative Development of Batch Dyed 3D Printed Acrylonitrile/Butadiene/Styrene Objects.

According to the great impact of additive technology on the development of modern industry, a lot of research is being done to obtain 3D printed parts with better properties. This research is extremely important because there are no scientific papers in the field of post dyeing of acrylonitrile/butadiene/styrene (ABS) 3D printed parts. The experiment was carried out using disperse dyes on ABS specimens. The obtained coloration of the specimens was in the primary colors (yellow, red, and blue) in the specified dyestuff concentration range and was evaluated using an objective CIELab system. Based on the obtained color parameters, remission values and Kubelka-Munk coefficient, dye mixtures and an ombre effect were performed to obtain patterns in the desired hues. Abrasion resistance of disperse dyed specimens was tested using different abrasive materials over a wide range of fineness to simulate different indoor and outdoor soils and was compared to abrasion resistance of specimens produced from the industrially dyed wire with the master batch. The results show that 3D printed ABS products can be produced in one or more desired shades with satisfactory abrasion resistance. This undoubtedly represents the added value of 3D printed ABS parts and extends their application to the field of creative industries and design, specifically footwear design.

The Effect of DBD Plasma Activation Time on the Dyeability of Woven Polyester Fabric with Disperse Dye.

This study consists of two parts. In the first, the woven polyester fabric, after washing to remove lubricant oils, was treated with the dielectric barrier discharge (DBD) plasma at the short plasma exposure time (from 15 to 90 s). The effect of the plasma exposure time on the activation of the polyester fabric was assessed by the wicking height of the samples. The results show that the wicking height in the warp direction of the plasma-treated samples improved but was virtually unchanged in the weft direction. Meanwhile, although the tensile strength in the warp direction of the fabric was virtually unaffected despite the plasma treatment time up to 90 s, in the weft direction it increased slightly with the plasma treatment time. Scanning Electron Microscope (SEM) images and the X-ray Photoelectron Spectroscopy (XPS) spectra of the samples before and after the plasma treatment were used to explain the nature of these phenomena. Based on the results of the first part, in the second part, two levels of the plasma treatment time (30 and 60 s) were selected to study their effect on the polyester fabric dyeability with disperse dyes. The color strength (K/S) values of the dyed samples were used to evaluate the dyeability of the fabric. The SEM images of the dyed samples also showed the difference in the dyeability between the plasma-treated and untreated samples. A new feature of this study is the DBD plasma treatment condition for polyester fabrics. The first is the use of DBD plasma in air (no addition of gas). Second is the very short plasma treatment time (only 15 to 90 s); this condition will be very favorable for the deployment on an industrial scale.

Characterizing azobenzene disperse dyes in commercial mixtures and children's polyester clothing.

Azobenzene disperse dyes are the fastest-growing class of dyestuffs, yet little is known about dye occurrences, sources, and transformations; azo dyes are also underrepresented in chemical standard catalogs, molecular databases, and mass spectral libraries. Many azo dyes are known to have sensitization, mutagenic, and carcinogenic properties. To fill these knowledge gaps, azo dyes were purified from dyestuffs by Soxhlet extraction and flash chromatography and characterized using ultra-high-performance liquid chromatography (UHPLC) coupled to a high resolution Orbitrap Fusion Lumos mass spectrometer operated in positive electrospray ionization mode, as well as by 1H and 13C NMR. Data were analyzed to identify likely chemical formulas and structures using a weight-of-evidence approach with multiple open-source, in silico computational mass spectrometry tools. Nineteen total azobenzene dyes were detected in dyestuffs via a non-targeted analysis approach; the azobenzene dyes Disperse Blue 79:1, Disperse Blue 183:1, Disperse Orange 44, Disperse Orange 73, Disperse Red 50, Disperse Red 73, and Disperse Red 354 were purified from raw dyestuffs. Samples of children's polyester clothing were then analyzed likewise. In clothing, 21 azobenzene disperse dyes were detected, 12 of which were confirmed and quantified via reference standards. Individual dyes in apparel were quantified at concentrations up to 9230 µg dye/g shirt, with geometric means ranging 7.91-300 µg dye/g shirt. Total dye load in apparel was quantified at up to 11,430 µg dye/g shirt. This research supported the development of reference standards and library mass spectra for azobenzene disperse dyes previously absent from standard and spectral libraries. By analyzing the scope and quantities of azo dyes in children's polyester apparel, this study will facilitate a more robust understanding of sources of these potentially allergenic and mutagenic compounds.