DE1219145B - Process for the production of metal-containing reactive dyes - Google Patents

Description

Process for the preparation of metal-containing reactive dyes It has been found that new metal-containing reactive dyes are obtained if dyes of the general formula are used in which Hal is chlorine or bromine, X is the radicals - N (alkyl) -, - N (aryl) -, -0- or preferably -S-1 A is a divalent radical which includes the group added to an aromatic-isocyclic or aromatic-heterocyclic radical, and h is a small integer, e.g. B. 1 to 4, preferably 2 to 3, and in which the ring B is unsubstituted in at least one o-position to the azo group, by the joint action of copper salts and oxidizing agents in a manner known per se in the copper complex compound of. corresponding o, o'-dihydroxyazo dyes.

The preparation of the starting dyes is described in Belgian patents 611736 and 619,274. The diazo components of the starting dyes are preferably 2-chloro-6-aminobenzothiazole, 2-bromo-6-aminobenzothiazole and their monosulfonic acids.

Examples of coupling components of the starting dyes are 1- or 2-hydroxynaphthalenesulfonic acids capable of coupling in the o-position to the hydroxyl group, which can be further substituted, and called pyrazolone sulfonic acids.

The reaction conditions used in the process according to the invention in the conversion of o-monohydroxyazo dyes into the copper complexes of the corresponding O, o'-Dihydroxyazo dyes are described in German Patent 807,289.

The copper complex compounds obtainable by the present process are ideal for dyeing and printing a wide variety of textile materials, in particular made of cellulosic fibers. However, you can also do so in a known manner decoppered and the resulting metal-free o, o'-dihydroxyazo dyes on the fiber re-metallized or by the action of metal-releasing agents in substance be converted into various metal complex compounds.

The dyes obtained have the general formula in the A a divalent residue that makes up the group added to an aromatic-isocyclic or aromatic-heterocyclic radical, B a divalent radical, which the group added to the remainder of a 2-halobenzimidazole, -benzoxazole or -benzthiazole, means.

Compared to the closest comparable prior art dyes, that is, the starting dyes known from Belgian patent 611736, the dyes obtainable according to the process are distinguished by better lightfastness and hypochlorite bleaching fastness. The parts given in the examples are parts by weight.

Example The solution obtained by coupling the diazo compound from 18.4 parts of 2-chloro-6-aminobenzothiazole dye paste obtainable with 30.4 parts of 1-hydroxynaphthalene-3,6-disulfonic acid is cold in 1500 parts of water with the addition of 40 parts of sodium acetate trihydrate dissolved and the solution filtered. Then add 25 parts of copper sulfate pentahydrate, dissolved in 100 parts of hot water, added, the copper complex of the monohydroxyazo dye as a compound that is sparingly soluble in water precipitates. After adding 360 room parts 10% hydrogen peroxide is stirred at normal temperature for several hours, until no more starting dye can be detected by chromatography. By addition of sodium chloride is the resulting copper complex of the o, o'-dihydroxyazo dye precipitated, washed with dilute sodium chloride solution and at 40 ° C under reduced Print dried. A brown-red powder is obtained which, in water, has a bluish-red tint Color is soluble and on cotton fabric according to those usual for reactive dyes Dyeing process results in Bordo shades of very good fastness properties.

In the same way, the corresponding copper complexes of the o, o'-dihydroxyazo dyes are obtained from starting dyes with the same diazo component and the coupling components given in the table below: Shade of the coloring of the Coupling component containing copper Dihydroxyazo- dye 1-hydroxynaphthalene-3,8-disulfone acid ........................ Bordo 1-hydroxynaphthalene-4,8-disulfone acid ........................ Bordo 2-hydroxynaphthalene-3,6-disulfone acid ........................ Bordo 8-chloro-l-hydroxynaphthalene 3,6-disulfonic acid ............... purple Shade of the coloring of the Coupling component containing copper Dihydroxyazo- dye 8-ethoxy-l-hydroxynaphthalene 3,6-disulfonic acid. . . . . . . . . . . . . . . violet 8-acetylamino-l-hydroxynaphthalene- 3,6-disulfonic acid ............... purple 1- (2,5-disulfophenyl) -3-methyl- pyrazolone- (5) ................. orange brown 1- (5,7-disulfonaphthyl-2) - 3-methylpyrazolone- (5) .......... orange brown

Claims (1)

Claim: Process for the preparation of metal-containing reactive dyes, characterized in that dyes of the general formula in which Hal is chlorine or bromine, X is the radicals - N (alkyl) -, - N (aryl) -, - O - or preferably - S -, A is a divalent radical which includes the group added to an aromatic-isocyclic or aromatic-heterocyclic radical, and n denotes a small integer and in which ring B is unsubstituted in at least one o-position to the azo group, by the joint action of copper salts and oxidizing agents in a manner known per se Copper complex compound of the corresponding o, o'-dihydroxyazo dyes transferred. When the application was announced, two coloring tables with explanations were laid out.