4,4 -Diaminostilbene-2,2 -disulfonic

It is possible to tailor dyes, by use of the stepwise reactivity of the chlorine atoms in cyanuric chloride (B-59MI11200), to a variety of applications. For example, in structure (16), two molecules of cyanuric chloride may be reacted with one molecule of a suitable diamine, such as 4,4 -diaminostilbene-2,2 -disulfonic acid, at 0-5 °C and then the subsequent bis-dichlorotriazinyl product condensed with two molecules of an azo dye with a primary amino group at 35-40 °C. The resultant dyes are applied very efficiently to cellulosic fibres at 85-90 °C with very little dye remaining in the dyebath. The same molecule may also be prepared by condensation of the dye with cyanuric chloride at 0-5 °C and then with the diamine at higher temperature. Dyes more suitable for printing application may be prepared by condensation of a dye-amino group with cyanuric chloride followed by a diamine and then a further molecule of cyanuric chloride. The various applications are manifested in the various ranges of ICI s Procion dyes. 

Bis-substitution of stilbene produces stronger fluorescence and the bis-triazine derivatives of diaminostilbenes have proved to be the most successful brighteners for cellulosics, in particular, and polyamides (60MI11200). The variety of substitution permutations in (90) is almost endless and many primary and secondary homocyclic and heterocyclic amines, thiols and phenols have been used. Synthesis of such compounds is straightforward and utilizes the convenient selectivity to substitution of cyanuric chloride. 4,4 -Diaminostilbene-2,2 -disulfonic acid condenses readily at 0-5 °C with cyanuric chloride, under slightly acidic conditions. In this case cyanuric chloride behaves as a monofunctional acid chloride and, although some by-products are unavoidable, two molecules of cyanuric chloride condense... 

C. I. Direct Yellow 12, 24895 [2870-32-8] 4,4 -Diaminostilbene-2,2 -disulfonic acid is bis-diazotized with an aqueous solution of sodium nitrite at 5°C. Next, phenol is dissolved in water, and sodium hydroxide solution and soda are added. To this solution is added the above bis-diazotized solution. Then, more 30 % sodium hydroxide solution is added. On the following morning, the solution is heated to 70 °C, and after addition of 30 % hydrochloric acid, the dye is salted out with rock salt. The damp press cake, ethanol, soda, 30 % sodium hydroxide solution, and ethyl chloride are kept in a closed stirrer vessel for 24 h at 100 °C (5 - 5.5 bar). The mixture is then cooled to 70 °C and transferred at its own pressure to a distilling vessel, from which the ethanol is distilled. After being cooled to 80 ° C, the mixture is suction filtered and dried at 100 °C. 

Walther obtained the first direct dyes by self-condensation of 4-nitrotoluene-2-sulfonic acid. So-called Sun Yellow is a mixture of different components, depending on the concentration of sodium hydroxide, the temperature, and the duration of the reaction. Oxidation of the intermediate dye and subsequent reduction with iron and hydrochloric acid gives 4,4 diaminostilbene-2,2 -disulfonic acid, which is used for fluorescent whitening agents and azo dyes. The shades are mostly yellow to red. The structure of Direct Yellow 11, 40000 [65150-80-3] (13 is one of the main components) probably contains a mixture of stilbene, azo, and/or azoxy groups. 

With the l,3,5-triazin-2-yl derivatives of 4,4 -diaminostilbene-2,2 -disulfonic acid proposed by B. Wendt in 1940 [25], optical brighteners came into full-scale industrial use. In 1941, 4,4 -bis (4-anilino-6-hydroxy-l,3,5-triazin-2-yl)aminoJstil-bene-2,2 -disulfonic acid disodium salt was introduced commercially under the trade name Blankophor B (3) [1264-32-0],... 

Triazinyl derivatives of 4,4 -diaminostilbene-2,2 -disulfonic acid have been available since 1941 and remain the most important class of optical brighteners in terms of quantity. Some 75 derivatives have been put on the market [1], In the textile industry, they find use in brightening cotton, regenerated cellulosic fibers, and polyamides. They can also be included in detergent formulations and used to brighten paper, either in the pulp or in the coating. 

The starting compound for all triazinylaminostilbenes is 4,4 -dinitrostilbene-2,2 -disulfonic acid [128-42-7], which is obtained by oxidizing 4-nitrotoluene-2-sulfonic acid with aqueous sodium hypochlorite in the presence of sodium hydroxide or, more recently, by atmospheric oxidation in an aqueous ammoniacal medium [39], The Bechamps reduction using iron filings etched with hydrochloric acid yields 4,4 -diaminostilbene-2,2 -disulfonic acid [81-11-8] (DAS). 

Sorensen M, Frimmel FH. Photochemical degradation of hydrophilic xenobiotics in the UV/H202 process influence of nitrate on the degradation rate of EDTA, 2-amino-1-naphthalenesulfonate, diphenyl-4-sulfonate and 4,4 -diaminostilbene-2,2 -disulfonate. Water Res 1997 31 2885-2891. 

Diaminostilbene-2,2 -disulfonate KrCl + H2O2 hv n.s. 0.01 mmol HPLC Sorensen and Frimmel (1997)... 

Sorensen M, Frimmel F (1997) Photochemical Degradation of Hydrophilic Xenobiotics in the UV/H2O2 Process Influence of Nitrate on the Degradation Rate of EDTA, 2-Amino-l-naphthalenesulfonate, Diphenyl-4-sulfonate and 4,4 -Diaminostilbene-2,2 -disulfonate, Wat. Res. 31 2885-2891. 

Diammonium phosphate 4, 6-Diamidino-2-phenyUndole dihydrochloride 4,4 -Diaminostilbene-2,2 -disulfonic acid N,iV-Diethylaminosulfur trifluoride iV,iV-Dimethylaminosulfur trifluoride Diethylaluminium 2,2,6,6-tetramethylpiperidide... 

Amsol 400, Amsol 500, Amsol 600. See Petroleum distillates, hydrotreated middle Amsol 650, Amsol 3800. See Petroleum distillates, hydrotreated light Amsonic acid. See 4,4 -Diaminostilbene-2,2 -disulfonic acid... 

Cl 37100. See 2-Methyl-4-nitroaniline Cl 37105. See 2-Methyl-5-nitroaniline Cl 37107. See p-Toluidine Cl 37110. See 3-Nitro-p-toluidine Cl 37115. See o-Anisidine hydrochloride Cl 37130. See 2-Methoxy-5-nitroaniline Cl 37225. See Benzidine Cl 37230. See o-Tolidine Cl 37235. See Dianisidine Cl 37240. See N-Phenyl-p-phenylenediamine Cl 37500. See P-Naphthol Cl 40000. See Direct yellow 11 Cl 40002 Cl 40003. See 4,4 -Diaminostilbene-2,2 -disulfonic acid Cl 40645. See Sodium-2-(4-styrvl-3-sulfophenyl)-2H-naphtho-(1,2-d)-triazole Cl 40800... 

Diaminostilbene-2,2 -disulfonic acid 7-Dimethylamino-4-methylcoumarin Disodium 2,2 -(1.2-ethenediyl) bis T5-[r4-[bis (2-hydroxyethyl) aminol-6-(phenylamine)-1,3,5-triazin-2-yl] amino] benzenesulfonate brightener, optical cellulosic blends Stilbene... 

Cl 1-15 pareth-9 Cl 1-15 pareth-12 Cl 3-15 pareth-1 Cl4-15 pareth-12 Decetli-9 Deceth-4 phosphate 4,4 -Diaminostilbene-2,2 -disulfonic acid Disodium ricinoleamido MEA-sulfosuccinate Lauramide DEA Lauramidopropyl PEG-dimonium chloride phosphate... 

Acid black 52 Acid black 58 Acid black 60 Acid blue 15 Acid blue 25 Acid blue 104 Acid blue 113 Acid blue 118 Acid green 20 Acid orange 10 Acid red 13 Acid violet 12 Acid violet 49 Acid yellow 25 Acid yellow 42 Acid yellow 65 Basic blue 6 Basic orange 1 Basic orange 2 Basic red 2 Basic red 12 Basic yellow 2 4,4 -Diaminostilbene-2,2 -disulfonic acid Dianisidine Direct black 38 Direct blue 1 Direct blue 6 Direct brown 2 Direct brown 95 Direct green 1 Direct red 39 p-Rosaniline hydrochloride dye, liq. cryst. displays 1,4,5,8-Tetra-(phenylthio) anthraquinone dye, medicine Fluorescein dye, mfg. 

Acid violet 49 Acid yellow 3 Acid yellow 36 Basic blue 7 Basic orange 1 Basic orange 2 Basic red 1 Basic red 2 Basic red 12 Basic yellow 2 Basic yellow 37 Carbon black D C Orange No. 4 4,4 -Diaminostilbene-2,2 -disulfonic acid Dianisidine Direct black 38 Direct blue 6... 

Decanediol 2-Decyl tetradecanoic acid 4,4 -Diaminostilbene-2,2 -disulfonic acid Dihydroxyethyl cocamine oxide Diisobutyl phthalate Dimethyl hydantoin-formaldehyde polymer Dimethyl hydrogenated tallow amine Dimethyl soyamlne Dodecenylsuccinic anhydride Dodecylhexadecanol Ethoxyethanol acetate Ethylene dioleamide Ethylene glycol Ethylene/VA copolymer 2-Ethylhexyl methacrylate 2-Ethylhexyl oleate 2-Furoic acid... 

Diaminostilbene-2,2 -disulfonic acid 65996-61-4 Cellulose Cellulose fibers CF 1500... 

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