Acid Yellow dyes

A Figure 7.11 Acid yellow dye, also called naphthol yellow. This is a nitroso dye. 

Many patients who respond to aspirin with asthma, rhinitis and urticaria are also sensitive to other analgesic anti-inflammatory drugs. Cross-sensitivity has been demonstrated with indomethacin, mefenamic acid, flufenamic acid, phenylbutazone, paracetamol, fenoprofen and ibuprofen (37, 39, 40C, 44C 4gc 55C 566 57R) Furthermore, cross-sensitivity may also occur with widely used food additives and colourings such as benzoic acid and the acidic yellow dye tartrazine (46 ", 47, 57, 58 ). In Holland tartrazine is used in the colouring of at least 79 pharmaceutical formulations including antibiotics and even preparations... 

The reducing action of sulphurous acid and sulphites in solution leads to their use as mild bleaching agents (for example magenta and some natural dyes, such as indigo, and the yellow dye in wool and straw are bleached). They are also used as a preservative for fruit and other foodstuffs for this reason. Other uses are to remove chlorine from fabrics after bleaching and in photography. 

Various methods of home-dyeing cotton and wool materials using natural dyes made from hulls of butternut, hickory nut, pecan, eastern black walnut, and Knglish walnut have been described (149). As far back as during the Civil War, butternut hulls have been used to furnish the yellow dye for uniforms of the Confederate troops. More recent attempts have been made to manufacture yellow and brown dyes from filbert shells on a commercial scale. The hulls are treated with copper sulfate and concentrated nitric acid to produce a yellow color, with ferrous sulfate to produce oHve-green, or with ammonia to produce mby-red (150) (see Dyes AND DYE INTERMEDIATES Dyes, natural). 

This mixture is known as Quinoline Yellow A [8003-22-3] (Cl 47000) and is most widely used with polyester fibers (109). Upon sulfonation, the water-soluble Quinoline Yellow S or Acid Yellow 3 [8004-92-0] (Cl 47005) is obtained. This dye is used with wool and its aluminum salt as a pigment. Foron Yellow SE-3GL (Cl Disperse Yellow 64) is the 3-hydroxy-4-bromo derivative. Several other quinoline dyes are commercially available and find apphcations as biological stains and analytical reagents (110). 

Of these dyes, Acid Yellow 151 (37) still has the greatest market among the yellows. As reported by USITC, production had increased to 1989 tons in 1985 from 706 tons in 1975. It is produced by coupling diazotized 2-amino-l-phenol-4-sulfonamide to acetoacetanilide followed by metallizing with cobalt to obtain a 1 2 cobalt complex. Acid Orange 24 (38), which is sulfanilic acid coupled to resorcinol to which diazotized mixed xyUdines have been coupled, is an unsymmetrical primary diasazo dye with a bihinctional coupling component. 

The Cl name for a dye is derived from the appHcation class to which the dye belongs, the color or hue of the dye, and a sequential number, eg. Cl Acid Yellow 3, Cl Acid Red 266, Cl Basic Blue 41, and Cl Vat Black 7. A five digit Cl number is assigned to a dye when its chemical stmcture has been made known by the manufacturer. The following example illustrates these points, where CA indicates Chemicalj bstracts and Cl Colourindex. 

The work with Cl Acid Yellow 129 used only unilamellar vesicles. The liposomes again suppressed exhaustion but increased dye-fibre bonding, leading to better fastness properties. It is claimed that liposomes can be used to control the rate of exhaustion. 

The yellow ink jet dyes (and pigments) are metal-free azo dyes, such as Cl Direct Yellow 132 and Cl Acid Yellow 23 (Tartrazine).48,49 Most of the magentas are azo dyes derived from H-acid (l-amino-8-naphthol-3,6-disulfonic acid), such as (62), and xanthenes, such as Cl Acid Red 52 and Cl Acid Red 289.48,49 Where high lightfastness is a requirement, a copper complex azo dye, Cl Reactive Red 23 (63), is used. However, such dyes are dull (see Section 9.12.3.2). Nickel complex PAQ dyes, such as (22), are claimed to be brighter and to have similar high lightfastness... 

The basicity of OLOA 1200 has been evidenced by its interaction with the oil-soluble acidic indicator dye, Brom Phenol Magenta E (EK 6810) which is normally yellow but turns blue and then magenta with increasing bacicity. The acidic form has an adsorption peak at 390 nm, the basic at 610 nm, and the isobestic point is at 460 nm. These spectra have be used to determine the concentration of OLOA 1200 in solution for adsorption isotherms. 

The color index (Cl) number, developed by the society of dyers and colorists, is used for dye classification. Once the chemical structure of a dye is known, a fivedigit Cl number is assigned to it. The first word is the dye classification and the second word is the hue or shade of the dye. For example, Cl Acid Yellow 36 (Cl 13065) is a yellow dye of the acid type. Additionally, a dye mixture may consist of several dyes for example, Navy 106 is composed of three reactive azo dyes remazol black B (Reactive Black 5), Remazol Red RB (Reactive Red 198), and Remazol Golden Yellow 3. 

Scheline RR, Nygaard RT, Longberg B (1970) Enzymatic reduction of azo dye, Acid Yellow, by extracts of Streptococcus faecalis, isolated from rat intestine. Food Cosmet Toxicol 8 55-58... 

Catalytic fading of certain mixtures of acid dyes on nylon, wool and their blends is a particularly significant problem of dye selection for carpets [165]. Xenotest ratings as low as 3-4 (much bluer) were found for green shades on nylon containing an azopyrazolone component such as Cl Acid Yellow 19 (3.150), which fades much more rapidly in the presence... 

The hydroxy-nitro dye Naphthol Yellow S (6.233 Cl Acid Yellow 1) was discovered in 1879 by Caro and is still manufactured. It is produced by sulphonation of 1-naphthol to give l-naphthol-2,4,7-trisulphonic acid, followed by replacement of the 2- and 4-sulpho groups in nitric acid medium. Nucleophilic substitution of l-chloro-2,4-dinitrobenzene with 4-aminodiphenylamine-2-sulphonic acid gives Cl Acid Orange 3 (6.234). 

The introduction of sulphonic acid groups into dyes of this kind provides acid dyes suitable for nylon, such as Cl Acid Yellow 199 (6.238). 

P.R.90 is derived from the fluorescein structure (147). Fluorescein is a yellow dye with intensely green fluorescence which was discovered by A.v.Bayer in 1871. It is prepared by heating resorcin and phthalic anhydride with zinc chloride or concentrated sulfuric acid ... 

Thus, RP-HPLC-MS has been employed for the analysis of sulphonated dyes and intermediates. Dyes included in the investigation were Acid yellow 36, Acid blue 40, Acid violet 7, Direct yellow 28, Direct blue 106, Acid yellow 23, Direct green 28, Direct red 79, Direct blue 78 and some metal complex dyes such as Acid orange 142, Acid red 357, Acid Violet 90, Acid yellow 194 and Acid brown 355. RP-HPLC was realized in an ODS column (150 X 3 mm i.d. particle size 7 /.an). The composition of the mobile phase varied according to the chemical structure of the analytes to be separated. For the majority of cases the mobile phase consisted of methanol-5 mM aqueous ammonium acetate (10 90, v/v). Subsituted anthraquinones were separated in similar mobile phases containing 40 per cent methanol. The flow rate was 1 ml/min for UV and 0.6 ml/min for MS detection, respectively. The chemical structure of dye intermediates investigated in this study and their retention times are compiled in Table 3.28. It was found that the method is suitable for the separation of decomposition products and intermediates of dyes but the separation of the original dye molecules was not adequate in this RP-HPLC system [162],... 

Uses Organic synthesis photographic agent manufacture of pesticides, herbicides, explosives, and wood preservatives yellow dyes preparation of picric acid and diaminophenol (photographic developer) indicator analytical reagent for potassium and ammonium ions insecticide. 

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). ... 

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