DE396519C - Process for the preparation of water-insoluble azo dyes - Google Patents

Description

Process for the preparation of water-insoluble azo dyes. In Patent 256999 and a number of others describe dyes which by combining unsulfurized diazo compounds with 2-3-oxynaphtho-esic acid arylides arise and for the production of real lacquers and valuable dyes on fibers can serve.

It has now been found that new dyes of particular good properties are achieved if any D.iazo compounds are used with the arylides the 2 - 3-oxynaphthioic acid which is halogen-substituted in the 6-position or its .. im Aryli @ drest still otherwise substituted descendants.

The nuances of the dyes thus obtained are compared to those of the corresponding combinations of patent 256999 surprisingly strongly to blue postponed. The present dyes show new, other good fastness properties also a remarkable resistance to sodium peroxide bleach.

The new dyes can be used to represent pigments and to Generate washfast dyeings on the fiber.

Examples of diazo components that can be used in the process are: Aniline, its homologues and substitution products, such as taluidines, anisidines, chlorine and nitroanilines, chloro- and nitrotoluidines, chloro- and nitroanisiekne, also naphthylainine, aminoanthrachitione, Aminoazo bodies, dianiino bases, etc.

All arylides of 6-halo-2-3-oxynaphthoic acid can be used as azo components Find use, such as. B. the anilides, toluidides, anisidides and their in the arylide radical chlorine and nitro substituted derivatives, naphthalides, etc.

The 6-halogen - 2, - 3 - oxynaphthoic acids, which have not yet been used for the production of dyes: can, for. B. be prepared by the method of patent 293897 from 6-halo-2 # 3-oxynaphthoic acid and arylamines.

The 6-halo-2 - 3-oxynaphthoic acids can be obtained analogously to the process for the preparation of 6-bromo-2-naphthol from F ranzen and S täu 1y 1e, Journal of Practical Chemistry, New Series, Volume 103, 368 will. If you put z. If, for example, the 6-bromo-2-3-oxynaphthoic acid obtained in this way, which crystallizes from glacial acetic acid in yellowish leaflets with a melting point of 260 to 2.61 '(uncorrupted), with aniline, 6-bromo-2-3 is formed -Oxynaphthoic anilide, which crystallizes from pyridin and water in colorless, fine, shiny flakes that melt at 273 ° (uncorrupted). It dissolves easily in pyridine and in heat in glacial acetic acid, it is less soluble in toluene and alcohol.

The 6-bromo-2 -3-oxynaphthoic acid-o-anisidide obtained in a corresponding manner shows the melting point 185 to 186 ° (uncorrected) from glacial acetic acid, and the 6-bromo-2-3-oxynaphtho, esic acid p-anisidide crystallizes out Aniline clen m.p. 29 ° to 292 ° (uncorr.). The 6-Brozn-2 - 3-Oxynaphthoyl-5 = chlor-i - 2-toluiidiine melts from glacial acetic acid recrystallized at 257 to 258 ° (uncorrupted), the 6-Bromo-2, -3-Oxynaphthoe- acid-a-naphthalide from glacial acetic acid at 237 bis 238 ° (uncorrected) and the corresponding ß-naph- thalid at 286 to 288 ° (uncorr.). Example i. Well cooked and dried tree wollgarn is with a solution of log 6-Bromo-2-3-oxynaphthoic anilide, 15 cc Caustic soda 34 ° Be and 2o cc Turkish red oil Impregnated in the liter, thoroughly wound down and, without z, i drying, in one with acetate blunted diazo solution, which 3.4 g 4 - Nitro- i - 2 - anisidine (OCH3: NHZ: NO, --- 1: 2: 4). Per liter contains, develops, washes and soaped. This gives clear, bluish red coloring Lungs of very good authenticity, sheep- th. In the same way, 5-N itro-i - 2- anisidine in Bordeaux, 5-nitro-i-2-toluidine Bordeaux red, 4-Nitro-i - 2-tol, lidin a blue- tinged red, 4-chloro-i - 3-tolitid ili a crowd laugh red, 4-chloro-i - 2-toll1 in a bluish tinge Red, dianisidine a blue. Example 2. Cotton yarn is used as in example i a solution of 10 g 6-Bron-2 - 3-Uxyllapli- thoesiitire-ß-naphtllalid, 15 cc sodium hydroxide solution 34 Be and 20 cc Turkish red oil per liter in impregnated, thoroughly wound and, without too to dry, in a blunted with acetate th diazo solution, which 3,4- 4-N itro-i # 2- anisidine (OCH .;: N H ..: NO ;; = i: 2: .j) im Liter contains, developed and, as usual, finished made. A clear, bluish red color is obtained very good fastness properties. The new dyes can also through Imprint of a diazo solution on green Goods according to the usual, Ari = eitsweise as well are produced in the nitrosa printing process the. With other 6-halo-2 - 3-Oxyiiaphtlioe- Acid arylidene can be used in the be done in the same way. So z. B. the combinations: 4-nitro-i. 2-anisidine with 6-bromo-2 # 3-oxy- naphthoic acid-o-anisidid .............. a red, 4-chloro-i. 2-toluidine with 6-bromo-2 - 3-oxy- naphthoic acid p-anididide. . . . . . . . . . . . . a bluish red, 4-nitro-i - 2-anisidine with 6-bromo-2 - 3-oxy- naphthoyl-5-chloro-i. 2-toluidine ......... a strong bluish red, 5-nitro-i. 2-anisidine with 6-bromo-2. 3-oxy naphthoy1-5-chloro-i. 2-toluidine. . . . . . . . a deep blue bordeaux, 5-chloro-i. 2-toluidine with 6-broin-2. 3-oxy naphthoyl-5-chloro-i. 2-toluidine. . . . . . . . a deep bluish red, 5-nitro-i. 2-anisidine with 6-bromo-2. 3-oxy naphthoic acid-a-naphthalide. . . . . ... . . . a blue garnet, 5-nitro-i. 2-anisidine with 6-bromo-2. 3-oxy naphthoic acid, 3-naphthalide. . . . . . . . . . . a bluish Bordeaux, 5-Clilor-i. 2-toluidine with 6-bromo-2 - 3-oxy- naphthoic acid 3-naphthalide. . . . . . . . . . . a strong bluish red.

Claims (1)

PATENT CLAIM: Process for the representation of water insoluble azo dyes, that any diazo compounds are coupled with the arylides of the 2 - 3-oxyi, apl, tlioic acid which is halogen-substituted in the 6-position.