Disperse Blue dyes

Anthraquinone-a,a -disulfonic acids and Related Compounds. Anthraquinone-a,a -disulfonic acids and their derivatives are important intermediates for manufacturing disperse blue dyes (via 1,5-, or 1,8-dihydroxyanthraquinone, or 1,5-dichloroanthraquinone) and vat dyes (via... 

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). 

DihydroxyanthraquiQone (anthranifin) [117-12-4] (47) is an important iatermediate for manufacturiag disperse blue dyes, eg. Cl Disperse Blue 73 (113), and is prepared from anthraquiQone-l,5-disulfonic acid by heating with an aqueous suspension of calcium oxide and magnesium chloride under pressure at 200—250°C (67). Alternative methods have been proposed, ie, direct replacement of the NO2 groups of 1,5-dinitroanthraquiaone (49) (68) or the route via 1,5-dimethoxyanthraquiaone [6448-90-4] (48) and subsequent hydrolysis (69). 

OCjOC -Dinitroanthraquinones and Related Compounds. 1,5- and 1,8-Dinitroanthraquiaone are the key iatermediates for manufacturiag disperse blue dyes via dinitrodihydroxyanthraquiaoae and vat dyes via diaminoanthraquiaones. 1,5-Diaitroanthraquinone [82-35-9] (49) and 1,8-dinitroanthraquinone [129-39-5] (50) are prepared by nitration of anthraquiaone with nitric acid ia sulfuric acid. a,P -Dioitroanthraquiaoaes are also formed ia the reactioa. 

High purity of 1,5-dimethoxyanthraquiaone is required for manufacturiag disperse blue dyes (Cl Disperse Blue 56 (11)). A small amount of unreacted 1,5-dinitroanthraquiaone ia 1,5-dimethoxyanthraquiaoae affects the brightness of the dye and makes it much duller. Improved processes have been reported (84,85). 

Figure 2. Molecular structure of Disperse Red and Disperse Blue dyes.

Figure 7. The dependence of Disperse Blue dye, mark-size on laser exposure time on Mylar and Kodar substrates.

Dichloroanlhraquinonc is an important intermediate for vat dyes and disperse blue dyes. 1.5-Dichloroanlhraquinone is prepared by the reaction of anthraquinone- 1,5-disuifonic acid with NaCIO in hot hydrochloric acid solution. 

Uihydroxyunihraquinone (anthraruhn) is an important intermediate for manufacturing disperse blue dyes and Is prepared from anthraquinnne-... 

Egli, R., The Chemistry of Disperse Blue Dyes, Past and Present, Chapter I, in Colour Chemistry, A.T. Peters and H.S. Freeman, Editors, Elsevier Applied Science, London, 1991. 

Guin JD. Seat-belt dermatitis from Disperse Blue dyes. 

Amyl-o-dimethylaminobenzoic acid induced an immediate photosensitivity response followed by a second, delayed erythema in workers formulating UV-cured inks [16]. On sun exposure, disperse blue dye 35 produced a transient erythema and burning in workers when leaving work [17]. 

Brandao FM, Altermatt C, Pecegueiro M, Pecegueiro M, Bordalo O, Foussereau J (1985) Contact dermatitis to Disperse Blue 106. Contact Dermatitis 13 80-84 Brandao MF, Hausen BM (1987) Cross reaction between Disperse Blue Dyes 106 and 125. Contact Dermatitis 16 289-290 Brandle I, Stampf JL, Foussereau J (1984) Thin-layer chromatography study of organic dye allergens. Contact Dermatitis 10 254-255... 

Another compound of interest is adenine [73-24-5] or 6-aminopurine (53) derived from pheny1a 2oma1ononitri1e (92). The introduction of the dicyanostyryl moiety has led to the industriali2ation of several methine dyes such as the Cl Disperse Yellow [6684-20-4] (54) (93). The Cl Disperse Blue 354 [74239-96-6] (55) also represents a new class of anTinoarylneutrocyariine dyes with a brilliant blue shade (94). The dimer of malononitrile is also used for the synthesis of new dyes (95). 

Blues are the single most important color in the disperse class, both in terms of amounts produced and doUar sales volume. Among all dyes. Disperse Blue 79 (100) (6-bromo-2,4-dinitroaniline [1817-73-8] coupled to 3-bis-(2-acetoxyethyl)-amino-/)-acetophenetidine [20249-05-2]) was the highest volume dye in the late 1980s and continues. As reported in 1985, the United States produced 2872 tons valued at 7.7 million. 

Monoazo dyes such as Disperse Blue 11 (102) and Disperse Black 1 (103) are appHed to cellulose acetate as a dispersion and dyed in the usual way, then diazotized in situ and coupled in this instance, to 3-hydroxy-2-naphthoic acid forming the blue and black shades, respectively. 

The synthesis of an anthraquinone dye generally involves a large number of steps. For example. Cl Disperse Red 60 [17418-58-5] (10) (Cl 60756) (a typical disperse red dye) requites five steps starting from anthraquinone, and Cl Disperse Blue 56 [31810-89-6] (11) (Cl 63285) requites six steps. 

World dye manufacturers have already begun to develop new types of dyes that can replace the anthraquinones technically and economically (1). Some successful examples can be found in a2o disperse red and blue dyes. Examples are brilliant red [68353-96-6] and Cl Disperse Blue 165 [41642-51 -7] (Cl 11077). They have come close to the level of anthraquinone reds and blues, respectively, in terms of brightness. In the reactive dye area intensive studies have continued to develop triphenodioxa2ine compounds, eg, (13), which are called new blues, to replace anthraquinone blues. In this representation R designates the substituents having reactive groups (see Dyes, reactive). 

Dihydroxy-4,8-dinitroanthraquiaone [128-91 -6] (54) is an important dye precursor for Cl Disperse Blue 56, and is prepared from... 

Substituted Anthraquinones. Commercially important blue disperse dyes are derived from 1,4,5,8-substituted anthraquiaones. Among them, diaminodihydroxyanthraquiaone derivatives are most important in view of their shades and affinity. Representative examples are Cl Disperse Blue 56 [31810-89-6] (11) Cl 63285) (126), and Cl Disperse Blue 73 (113) (115). Introduction of a halogen atom ortho to the amino group improves affinity and lightfastness. 

Cl Disperse Blue 56 is the most important blue dye for polyester fibers because it has a brilliant shade, excellent lightfastness, and good leveling properties. 

Cl Disperse Blue 73/72222-75-2] Cl 63265) is an example of a dye that was developed to improve sublimation fastness for special use, eg, thermosol dyeing or printing. This dye also has a bright shade, excellent lightfastness and good leveling properties. Cl Disperse Blue 73 (113) is prepared as follows, where R = H or CH,. 

A Substituted-l-Amino-4-hydroxyanthraquinones. These dyes show good affinity and hghtfastness and give violet to blue shades. However, the sublimation fastness is in general not satisfactory. An example is Cl Disperse Blue 72 [81-48-1] (117) (Cl 60725), prepared from leucoquinizarin and -toluidine. 

The fate of one dye that has been thoroughly studied in the a2o dye Disperse Blue 79 [12239-34-8] (6) (Cl 11345) which may be designated 6-bromo-2,4-dinitro-aniline—>3-(Al,A/-diacetoxyethylamino)-4-ethoxyacetanihde (see Azodyes). 

The U.S. International Trade Commission has Hsted the production of Disperse Blue 79 at 2300—4500 t per year in the United States from 1980 through 1984 (261). Thus Disperse Blue 79 is the largest volume dye on the market today (262) the average annual production in the United States from 1983—1985 was approximately 3200 t. 

It has been estimated that during the manufacture of Disperse Blue 79 there would be released the following amounts of dye 4.5—14 t per year at a total of nine sites with an estimated 3—20 kg per day (261). 

E. J. Weber, Fate of Textile Dyes in the Aquatic Environment Degradation of Disperse Blue 79 in Anaerobic Sediment-Water Systems, Environmental Research Laboratory, U.S. EPA, Athens, Ga., Mar. 1988. 

Bismethylaminoanthraquinone (Disperse Blue 14) [2475-44-7] M 266.3, A,max 640 (594)nm. Purified by thin-layer chromatography on silica gel plates, using toluene/acetone (3.1) as eluent. The main band was scraped off and extracted with MeOH. The solvent was evapd and the dye was dried in a drying pistol [Land, McAlpine, Sinclair and Truscott J Chem Soc, Faraday Trans I 72 2091 7976]. 

To find the most efficient selectors in the library, blue and red dye-labeled enantiomeric probe molecules 6 and 7 were prepared by linking pentafluorophenyl esters of L- and D-proline with Disperse Blue 3 and Disperse Red 1, respectively, through an isophthaloyl (shown in structures 6 and 7) or a succinyl moiety. Eor detection, a... 

The structures of a number of neutral and anionic polymethine dyes are illustrated in Figure 6.3. There are many types of neutral poly-methines, utilising a wide range of electron donor and acceptor groups. For example, C. I. Disperse Yellow 99 (114) and C. I. Disperse Blue 354... 

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...

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