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UNITED STATES PATENT of FICE Patented July 28, 1953 2,647,113 UNITED STATES PATENT of FICE 2,647,113 AZO DYESTUFF Robert Elaintz, and Georges Mingasson, Paris, France, assigners to Compagnie Francaise des Matierescorporation Colorantes, of France Saint-Denis, France, a No Drawiag. Application April 4, 1951, Serial No. 29,317. In France August 24, 1945: Seetion. 1, Public Law 690, August 8, 1946 Patent expires August 24, 1965. 3 Claims. (C. 260 - 9) 2 The present application is a continuation-in 2,6 - amino - 4 hyaroxy - 3 - thiophenol and part of our patent, application. Serial Number ailino-4-hydroxy-3-inaethyl-2-thiophenol. 743,420, filed April 14, 1947. Said ortho-aminophenols are new conapounds, Our invention relates to metallizable azo-dye Ehey may be obtained; for example, by treating Stuffs. 5 chloro-nitrophenols in which the chlorine: atom Cne object of Our in Veration is to provide azo is in para position and the hydroxy group in or dyestuffs which are soluble in sodium sulfide and thoposition with respect to, the nitro group with are of great inaportance for dyeing cellulosic fi a soluble: salt. of hydrosulfuric acid or by reduc bres. ing; ortho-nitrophenols substitued by a sulfo Another object of the invention is to provide O chloride group: Inetallizable azo-dyestuffs, which, after being, ap The dyestuffs prepared according to our inven plied on cellulosic fibres, in a sulfide bath are tion are soluble in sodium sulfide and the so capable of acquiring remarkable fastnesses when obtained solutions are capable of dyeing, cellulosic treated with combinations, of heavy metals such fibres; the resulting dyeings, acquire remarkable aS COpper. fastiesses when, the dyed cellulosic fibres are According to our invention a benzenic ortho treated with compounds of heavy metals-such as: aninophenol Substituted on the benzenic nucleus Copper, for example. - - - - by a mercapto, group.is, diazotized and the so ob The following are: non-limitative examples: il tained diazor-compound, is coupled with a cour lustrating. Our invention. In said examples the pling component containing an hydroxy group, 20 parts are parts by weight, except where other coupling. in a-position adjacent. that of said hy wise indicated. droxy group, the coupling component, and the Eacample 1 diazo-compound having. no. Solublilizing groups 40 parts sodium salt of chloro-3-nitro-6-phenol other than hydroxy groups. are heated for a period of 7" hours so that the The so. obtained azo-dyestuffs have the follow 25 condensed liquid flows back, with 400 parts water ing general formula: and 125 parts crystallized sodium sulfide. The HS-A-N-N-B Solution, red-brown at first, takes, on a slight greenish-brown hue. After cooling, a carbon di in which A. represents; a benzenic nucleus. Substi oxide flow is caused to pass through..the solution tuted by a hydroxy group in ortho position. With and 5 parts sodium acetate are added, as well as respect to the azo-group, and B is the radical of hydrochloric acid until the solution becomes acid a coupling Component containing an hydroxy group, coupling in, a position adjacent that of towardsA light litmus. yellow, amino-4-hydroxy-3-thibphierol- said: hydroxy group,.A. and B. containing no Sol precipitate is. obtained, which is soluble in acids ubilizing groups. other' than hydroxyl groupS. 35 and alkalies and alters rather readily in the press The benzenic nucleuS represented by. A may, ence of air. contain other substituents beside: the. --OH and Eacample 2 -SH groups, except, however, as; above stated, it must not contain: groups which confert Solubil A mixture of 40' parts dichloro-3-4-nitro-6- ity in water, nor groupS. which may be:reduced in: 40 phenoli. 33 parts of 30% soda, lye, 16: parts of the dyeing sodium sulfide: bath; permissible sub crystallized sodium sulfide and 600 parts of water stituents comprise; more; particularly, alkyl are boiled for 7 hours in ari. apparatus provided groups-and-halogenatoms. with. a. reflux, cooling device;. After cooling, 10. The diazotization and coupling are: carried out parts: Sodiumiacetate, are added: and thenhydro in the usual manner. It is sometimes of advan 45 chloric acid' until thie: Solution. becomes acids to. tage to accelerate the coupling reaction by adding. litmus. The restilting precipitate is filtered, a Solvent. Such as:pyridin. washed: with water. and readissolved in dilutethyer When using, the: current, coupling compounds. drochilbric acid; after filtrationii, the solution: is it is possible to obtain a very extended range: of again. precipitated by means of an addition, of: hues with, the same diaZO. Thus, with amino-4- 50 Sodium. acetate. The: properties of thie resultirig hydroxy-3-thiophenol, or, with one of the deriva chilbro-6-amino-4-hyidroxy-3-thiophenol; a reisima. tives. of said, compound, chlorinated in positions. ilar to those of the Substance: prepared; accord 6, or, 2-6, colours are. obtained, such as yellow, ing to Example 1 garnet red; black, etc. The starting. Substance, which has a, meltih.g The ortho-aminophenols- the benzenic-nucleus, point of 82-82.5°C..is...prepaired by causing dilute of which is substituted by a mercapto group, whichi, SOda to act. upon trichloro-3,4,5-dinititja.12i. may be used, for carrying out the present. inven benzene. tions are, for example, amino-4-hydroxy-3-thio Eacample 3 phenol; amino-3-hydroxy-4-thiophenol, . chloro 8 parts of trichloro-2-3-4-nitro-6-phenol are: 6 - amino - 4 - hydroxy - 3 - thiophenol, dichloro 60 dissolved in 200 parts of water and 4.5 parts of 2,647,118 4 30% soda, .lye. After adding3 8 parts of crystal diazotization is dissolved in 125 parts of water lized sodium sulfide, the Solution is boiled for and 25 parts of 20 Bé. hydrochloric acid and a few minutes. Dichloro-2-6-nitro-4-hydroxy-3- diazotized with the above mentioned quantity thiophenol is then precipitated by means of an of sodium nitrite in 20% solution. The obtained addition of hydrochloric acid. The resulting suspension of diazo-compound is poured into a compound, recrystallized from alcohol, melts at solution containing 16 parts of hydroxy-2-naph 103° C. 12 parts of said compound are dissolved thalene, 14 parts of 38 Bé. Soda-lye and 100 parts in 200 parts of water and 14 parts of 35%, Soda, of Water. After an addition of hydrochloric acid lye, and Sodium hydrosulfite is then added at the precipitated dyestuff is filtered, washed and low temperature, while stirring, until the Solution O dried. Its characteristics are given in Table II is discoloured, while maintaining the alkaline pH at the end of the present specification. of the medium. By addition of acetic acid, di The chloro-6-amino-4-hydroxy-3-thiophenol chloro - 2 - 6 - amino - 4 - hydroxy - 3 - thio used for this preparation was obtained accord phenol precipitates, which can be recrystallized ing to the procedure of Example 2. from methyl alcohol. 5 Eacample 8 Eacample 4 A solution of amino-3-hydroxy-4-thiophenol 11 parts of amino-4-hydroxy-3-thiophenol ob prepared as stated hereinafter is diazotized at a tained according to the method described in Ex temperature of 0-5 C. with 62.5 parts by volume ample are dissolved in 17 parts of 31% hydro 20 of a solution containing 280 grams of Sodium chloric acid and 250 parts of water. The ob nitrite per litre. A diaZO-compound is precipi tained solution is cooled down to 5° C. and is tated, which is filtered and washed with water. added to a solution of 3.5 parts of Sodium nitrite A quantity of Said moist precipitate contain in 30 parts of water. The resulting liquid, which ing 8.85 parts of dry product is added in portions contains an orange-brown precipitate of diazo to a Solution containing 8 parts of hydroxy-2- compound, is poured into a solution containing naphthalene, 2.3 parts of sodium hydroxide and 7.2 parts of beta-naphthol, 200 parts of water 60 parts of Water. The whole is then Stirred and 12 parts of 35% soda, lye. When the cou for 3 hours at room temperature and for One pling is ended, the solution is neutralized with hour at 40° C. After a rest of 12 hours, 30 parts hydrochloric acid and a dyestuff precipitates. 30 by volume of a saturated Solution of sodium chlo Said dyestuff is filtered, washed and dried. It ride are added, the temperature is brought to forms a bluish-black powder, yielding at room 90° C., and the dyestuff obtained is filtered after temperature a blue solution in a Sodium sulfide cooling and Washed With Water. solution. The addition of 50 parts of pyridine The characteristics of the so obtained dyestuff to the beta-naphthol solution considerably speeds 35 are given in Table IV at the end of the present up the coupling. Specification. Eacample 5 The solution of amino-3-hydroxy-4-thiophenol used is obtained by mixing little by little 95 parts The amino-4-hydroxy-3-thiophenol obtained, of nitro-3-hydroxy-4-benzene sulfochloride and as stated in Example 1, from 195 parts of the 40 150 parts of zinc powder in 440 parts by volume Sodium salt of chloro-3-nitr0-6-phenol is im of 22 Bé, hydrochloric acid, without exceeding pasted in 640 parts of water and dissolved by the temperature of 50° C. The whole is brought addition of 1150 parts of 20° Bé, hydrochloric acid. to a boil and 50 parts of zinc powder and 30 parts The obtained solution is cooled down to 5° C. and by volume of hydrochloric acid are further added.
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