Disperse Orange dyes

Dichloroanthraquinone [82-46-2] (46) is an important iatermediate for vat dyes and disperse blue dyes. Examples are Cl Vat Violet 13 [4424-87-7] (170), Cl Vat Orange 15 [2379-78-4] (154), and Cl Disperse Blue 56 [31810-89-6] (11). 1,5-DichloroantliraquiQone is prepared by the reaction of anthraquiQone-l,5-disulfonic acid with NaClO iu hot hydrochloric acid solution. Alternative methods from 1,5-dinitroanthraquiaone (49) by reaction of chlorine at high temperature ia the presence of phthaUc anhydride have been proposed (66). 

A study of the degradation of two azo disperse dyes. Disperse Orange 5 [6232-56-0] (1) Cl 11100) and Disperse Red 5 [3769-57-1] Cl 11215) showed reduction of the azo linkage into aromatic amines and further dealkylation to -phenylene-diamine [106-50-3] (2) (255). 

Figure 7.7. Numerically, azo dyes form by far the most important chemical class of disperse dyes. Azo disperse dyes may be classified into four broad groupings. The most numerous are the aminoazobenzenes which provide important orange, red, violet and blue disperse dyes. They are exemplified by C. I. Disperse Orange 25 (157), C. I. Disperse Red 90 (158) and C. I. Disperse Blue 165 (159). A comparison of these three aminoazobenzene dyes provides an illustration of the bathochromic shift...

Figure 12.8 Overall dependence of observed parameters in dyeing with Cl Disperse Orange 21 in the presence of a mixture of three agents [89], The value within each symbol represents a percentage of the maximal effect (= 100%) for that factor...

An inverse relation between the efficiency of decolorization and the dye concentration has frequently been observed. This fact can be ascribed to several factors, the main of which can be considered the toxicity of the dyes at higher concentrations [41, 45, 51-53]. With Reactive Red 3B-A, concentrations from 100 to 2,000 ppm were tested with C. bifermentans [5]. At concentrations less than 200 ppm, 90% decolorization within 12 h was observed, while at very high dye concentration (>1,000 ppm), the decolorization rate decreased. Khalid et al. [54] observed an inverse relationship between the velocity of the decolorization reaction and the dye concentrations between 100 and 500 mg L 1 azo dye (Reactive Black 5, Direct Red 81, Acid Red 88, and Disperse Orange 3) by Shewanella putrefaciens. A decrease in decolorization percentage at a Acid Black 210 initial concentration growing from 100 to 400 ppm was also observed with V. harveyi, but the decrease was low [44]. 

The ability to use azo dyes as sole energy and carbon source by bacteria to be able to reduce the azo bond aerobically by a cometabolic way has been reported [2,4]. A mixture of four structurally different dyes (Acid Red 88, Reactive Black 5, Direct Red 81, and Disperse Orange 3) was used as sole source of carbon and nitrogen to select six strains of bacteria tested for the ability to decolorize the dyes individually or in mixtures a S. putrefaciens strain was identified as the most efficient [45]. 

Two bacterial Shewanella species, S. putrefaciens and S. oneidensis, previously selected on the basis of their ability to degrade azo dyes, were also tested in saline medium at different salt concentrations of up to 10% to evaluate their potential to decolorize four structurally different azo dyes Reactive Black 5, Direct Red 81, Acid Red 88, and Disperse Orange 3. Full decolorization was reached at salt concentrations up to 6% the decolorization velocity was inversely related to salt concentration. The rate of decolorization was increased by yeast extract and a calcium source, while was decreased by glucose and by a nitrogen source [54]. 

The relative rates of diffusion of Cl Disperse Orange 3 on nylon, acetate and polyester indicated in Table 3.14 are reasonably consistent with those measured independently in the early days of polyester dyeing [113], as shown in Table 3.15. These figures, for three disperse... 

The widespread adoption of high-temperature dyeing methods has also allowed the use of simple disazo structures, such as Cl Disperse Orange 13 (4.89) and Cl Disperse Orange 29 (4.90), as economic dyes giving chiefly yellow and orange hues. The latter dye is known to exist in the syn conformation in the crystal [95] the unsubstituted parent dye prefers the anti conformation. A few monoazo and disazo disperse dyes have absorption bands in the near infrared [96]. 

TLC separation of the components of black dye commercial product (BDCP) was performed on silica layers. The chemical structures of the dye components are shown in Fig. 3.17. Dyes were extracted from the effluent of the dye processing plant, from the untreated river water and from the drinking water treatment plant. The organic extracts were further concentrated and purified using a copolymer of styrene divinyl benzene. The mobile phase for TLC separation consisted of toluene-ethyl acetate (8 1, v/v). The Rp values of dye components were 0.43 (C. I. Disperse Violet 93), 0.48 (C. I. Disperse Orange 37) and 0.59 (C. I. Disperse Blue 373), respectively. 

Fig. 3.38.The IUPAC names of Sudan azo dyes are as follows Sudan 1 = 1— [(2,4-dimethylphenyl)azo]-2-naphtalenol Sudan II = l-(phenylazo)-2-naphtol Sudan III = l-(4-phenylazophenylazo)-2-naphtol Sudan IV = o-tolyazo-o-tolyazo-beta-naphtol and Disperse Orange 13 = 4-[4-(phenylazo)-l-naphtylazo]-phenol. Azo dyes were separated in an ODS column (250 x 2.1 mm i.d. particle size 5 /xm) at 35°C. The isocratic mobile phase consisted of 0.1 per cent formic acid in methanol-0.1 per cent formic acid in water (97 3, v/v). The flow rate was 200 /xl/min. MS conditions were nebulizing and desolvation gas were nitrogen at the flow rates of 50 and 5551/h, respectively electrospray voltage, 3.0 kV cone voltage 25 V source temperature, 110°C desolvation temperature, 110°C. Azo dyes were extracted from the samples by homogenizing 1 g of sample with 10 ml of acetone, then the suspension was centrifuged and an aliquot of 3 ml of supernatant was mixed with 1 ml of deionized water, filtered and used for analysis. LC-ESI-MS/Ms SRM traces of standards and spiked samples are listed in Fig. 3.39. It was found that the detection and quantitation limits depended on both the chemical structure of the dye and the character of the accompanying matrix. LOD and LOQ values in chilli tomato sauce...

Fig. 3.38. Chemical structures of the azo dyes investigated and of the internal standard Disperse orange 13. Reprinted with permission from F. Calbiani el al. [115].

The main aromatic amines used as diazo components are substituted anilines or naphthylamines and the coupling components substituted iV-aUcylanilines, phenols, naphthylamines and naphthols. Heteroaromatic diazo and coupling components are widely used in commercial azo dyestuffs. The main heterocyclic conpling components are pyrazalones (2.6) and, especially, pyridones (2.8). These are nsed to prodnce bright yellow and orange monoazo dyes, such as Cl Acid Yellow 72 (2.7) and Cl Disperse Orange 139 (2.9). ... 

With regard to heterocyclic compounds as coupling components, the importance of the formerly widespread pyrazolone-, aminopyrazole-, and 4-hydroxy -quinolone-based yellow azo dyes has greatly diminished with the advent of the tinctorially superior and therefore more economical pyridone azo dyes. Only a few examples have survived and then only for special applications such as for dyeing of acetate fibers. Examples are C.I. Disperse Orange 56 and C.I. Disperse Yellow5. (for structure, see Section 3.2.5). 

Dyes. In dyeing PES-wool mixtures, disperse dyes are used for the PES component, and acid or metal-complex dyes for the wool. Disperse dyes can soil wool to a great extent. Since they produce poorly fast dyeings on wool, the dyes selected must stain wool as slightly as possible or must be easily removable by a washing step, which may be reductive if necessary. Frequently used dyes are C.I. Disperse Yellow 23, 54, 64 C.I. Disperse Orange 30, 33 C.I. Disperse Red 50, 60, 73, 91, 167, 179 and C.I. DisperseBlue 56, 73, 87. Premixed dyes consisting of disperse and wool dyes are occasionally available. 

FOOD YELLOW 3 C.I. FOOD YELLOW 3, DISODIUM SALT CILEFA ORANGE S DISODIUM SALT of 1-p-SULPHOPHENYLAZO-2-NAPHTHOL-6-SULPHONIC ACID DISPERSED ORANGE 11348 DISPERSED YELLOW 12116 DOLKWAL SUNSET YELLOW DYE FDC YELLOW LAKE 6 DYE FD C YELLOW LAKE 6... 

If they are ingested, dyes and particularly those that have an azo group can be metabolized by the intestinal microflora or by the liver enzymes. So, their effects can occur in organs responsible for metabolism or elimination, like the liver and urinary tract. Skin metabolism may also be responsible for the transformation of dyes, for example, those from colored textiles that can leach from the fabric and migrate to the skin. For example Disperse Orange 3 is degraded to p-phenylenediamine (PPD) and nitro-aniline in the skin (Figure 1). Direct Blue 14 (Cl 23850), after azo reduction, converts to the aromatic amine o-toluidine and other amines when incubated with cultures of Staphylococcus aureus. 

Disperse Orange 76 (Figure 13) is often positive and was thought to be one of the main causes of dye allergy in men, together with Disperse Blue 3 (an anthraquinone dye). 

FIGURE 10 The solubility of C. I. Disperse Orange 30 dye in supercritical carbon dioxide as a function of pressure. Lines are calculated with Peng-Robinson equation of state (Equation 12). (From Baek, J.-K., Kim, S., Lee, G.-S., and Shim, J.-J., Korean J. Chem. Eng., 21(1), 230-235, 2004.)... 

Product composition Dye mixture - Acid Blue 298, Acid Red 182, Direct Blue 218, Disperse Orange 25, Disperse Yellow 3, Direct Yellow 11. 

OTHER COMMENTS o-anisidine is used as an intermediate in the manufacture of azo dyes and in the production of Solvent Red 1 used to prepare guaiacol via diazotization and hydrolysis p-anisidine is used in the manufacture of azo dyes and as a chemical intermediate for Vat Red 29, Disperse Orange 15, and Azoic Coupling Component 13. 

Preparation of micrometer-sized microspheres of poly(styrene-co-butyl methacrylate) by dispersion polymerization in the presence of dyes such as Nigrosin, Sudan red 7B, Sudan black B, rhodamine B base, ethyl eosin, phenolphthalein. Disperse orange 13, and Disperse blue [87]. 

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