DE537233C - Process for the preparation of azo dyes - Google Patents

Description

Process for the preparation of azo dyes It has been found that valuable azo dyes can be obtained when using o-oxy diazo compounds on the nitrogen-substituted oxyquinolone derivatives and the reaction components is chosen so that the coupling product contains at least one sulfonic acid group.

The new dyes deliver on metal-stained animal fibers Dyeings of very good fastness properties. Likewise, through follow-up treatment the dyeing on unheated fibers, for example with bichromate, is excellent get real colorations. Finally, it is also easy to make metal complex compounds to produce in substance, which are valuable dyes, which are in particular characterized by a very good affinity for animal fibers and also frequently the corresponding dyes made using 2 # 4-dioxyquinoline surpass. Another technically important advantage of the metal complex compounds of the new dyes is generally very good in organic solubility Solvents, which is why they are used, for example, to dye nitrocellulose lacquers can use, including those made using 2 # 4-Dioxyquinoline Dyes are generally unsuitable because of their poor solubility.

By changing the o-oxydiazo compound on the one hand and the substituents On the other hand, the color tone can be determined on the nitrogen or in the benzene nucleus of the oxyquinolone affect the resulting dyes.

Example 1 The diazo solution prepared in the usual way is left from 22.3 parts of 4-chloro-2-aminophenol-6-sulfonic acid in zoo parts of water at about 1o ° in a solution of z3.7 parts of N-phenyl-4-oxy-2 = quinolone in 33o parts of water, Run in 11.7 parts of 35 percent sodium hydroxide solution and 6o parts of soda and stir until for the disappearance of the diazo reaction at 10 to 15 '. The dye is then in The heat is deposited by adding salt, suctioned off and dried. The dye is a brownish-purple powder that dissolves in water with a purple color. Acidification changes the color to orange. Be on chrome-stained wool burgundy coloration preserved. The same color is obtained by chroming the orange color on rustic stained wool. Will the product in the with .red color soluble complex chromium compound, for example by heating with chromium formate solution, transferred, it dyes unheated wool in a very real blue-tinged red.

EXAMPLE 2 The diazo solution prepared in the usual way of 2.3 parts of 4-nitro-2-aminophenol-6-sulfonic acid in 20 parts of water is left at about 10 ° in a solution of 1.9 parts of N-Ätliyl-, t-. Oxy-2-quinolone (made from N ethylanthranilic acid and acetic anhydride, FP265 °) pour in 25 parts of water, 417 parts of 3 5 percent sodium hydroxide solution and 6 parts of soda and stir at about 10 to 15 ° until no more diazo compound can be detected. The dye is then filtered off with suction and dried. It is obtained as a red-brown powder with a green sheen, which dissolves in water with a red color that changes to orange on acidification. The dyeing on unstained wool is bluish-tinged red and changes to a slightly more yellowish red with excellent fastness properties as a result of post-chrome plating. EXAMPLE 3 The diazo solution of 20 parts of picric acid prepared in the usual way is left at 10 to 15 ° in a solution of 25.5 parts of Bz - sulfo-N-methyl-4-oxy-2: quinolone (prepared by brief treatment of N- methy1-4-oxy-2-quinolone with 23% oleum) in zoo parts of water, - the 25 parts of soda. are added, run in with stirring. After the formation of the dyestuff has ended, the dyestuff is precipitated by weak acidification and salting out with potassium chloride, filtered off with suction and dried. It then represents a dark brown powder that dissolves in water, dilute acids, and dilute alkali with a brown color. Wool is dyed brown. Chromium plating gives a very real reddish brown.

Example 4 The diazo solution from 25 Part of i-amino-2-.oxynaphthalene-4-sulEonic acid is stirred at 10 to 20 ° in a solution of i 7.5 parts of N-methyl-4-oxy-2 = quinolone in i5o parts of 20 percent strength Caustic soda entered. After the formation of color has ended, the mixture becomes minerally acidic made and the dye formed is sucked off. After drying, it makes a brown one Powder that dissolves in water with an orange color, which changes when soda is added Turns purple. Wool is dyed reddish brown. Chromium plating gives a very real violet.

Example 5 is allowed to the diazo solution in the usual manner from 22.3 parts of 4-illustrated Clilor-2-aininophenol-6-sulfonic acid in water at about 2oo parts io ° my solution of 27 parts of N, '2'-methoxyphenyl) 4 -oxy-2-quinolone in 33o parts of water, 11.7 parts of 35 percent sodium hydroxide solution and 6o parts of soda run in and stir at 10 to 15 ° until the diazo reaction disappears. [The N- (2'-methoxyphenyl-) 4-oxy-2 = chüiolon is obtained by heating N- (2'-methoxyphenyl) anthranilic acid with 21/2 times the amount of acetic anhydride at boiling temperature for one hour.] By adding 10% Table salt is used to cause the dye to deposit. After drying, it is a red-brown powder with which bordeaux-red colorations are obtained on chrome-stained wool. The same color is obtained by coloring to full and re-chrome plating. The dye can be converted into the complex chromium compound in the following way: The dye obtained from 22.3 parts of 4-chloro-2-, aminophenol-6-sulfonic acid in the manner described above is made into a paste with about 700 parts of water, with a Solution of 2 parts of chromium oxide in 150 parts of 3% formic acid and heated in the autoclave for 3 hours to 120 °. After cooling, the dye is deposited by adding the same volume of a 25% saline solution. The coloring to Volle gives a bluish red very good fastness properties.

The free acid of the chromium complex dye is also excellent for dyeing commercially available nitrocellulose lacquers. Main receives strong, bluish-tinged red Dyeings of very good lightfastness.

Claims (1)

PATANT AN SPRUCH Process for the preparation of azo dyes and their metal complex compounds, characterized in that o-oxydiazo compounds are coupled with oxychiliolones which are substituted on the nitrogen and which may optionally be further substituted in the benzene nucleus, and the reaction components are chosen so that the coupling product is at least contains a sulfonic acid group, whereupon the azo dyes formed are optionally converted into their metal complex compounds.