DE1000546B - Process for the preparation of copper-containing disazo dyes - Google Patents

Description

Process for the production of copper-containing disazo dyes The subject of patent application S q.3051 IV b / 22 a, addendum to patent 904 228, is a process for the production of copper-containing disazo dyes, which consists in adding one mole of the symmetrical urea of the 2-amino-5- oxynaphthalene-7-sulfonic acid in any order, on the one hand, with one mole of the diazo compound from an aminobenzene of the composition wherein B denotes hydrogen or methyl and W denotes an aliphatic or carbocyclic hydrocarbon radical, and on the other hand with 1 mol of the diazo compound from an aminobenzenesulfonic acid amide derivative of the composition wherein X is hydrogen or methyl, Y is hydrogen or alkyl and Z is hydrogen, alkyl, phenyl or substituted phenyl, couples and treats the disazo dye obtained with a copper donor.

It has now been found that valuable copper-containing disazo dyes are also available obtained when the aminobenzenesulfonic acid amide derivative is obtained in the above-mentioned process the composition (II) is replaced by an amine of the composition b - R - N H2 (IV), wherein b is oxy, methoxy or carboxy and R is a radical of the benzene series, in which the substituent b and the N Hz group are in the ortho position to one another and which by water-solubilizing groups customary in azo dyes may be substituted, where, if b is oxy or methoxy, the sulfonic acid amide group and the sulfonic acid amide groups substituted on the nitrogen atom by alkyl or aryl groups with exception of.

The new process is therefore characterized in that one mole of the symmetrical urea of 2-amino-5-oxynaphthalene-7-sulfonic acid is mixed with one mole of the diazo compound from an aminobenzene of the composition in any order in which B and W have the meanings given above, and on the other hand with 1 mole of the diazo compound from an amine of the composition bR-NH2 (IV) where b and R have the meanings given above, couples and treats the disazo dye obtained with a copper donor.

As water-solubilizing groups customary in azo dyes, which be contained as further substituents in the compound of the composition (IV) are, especially noteworthy, the sulfonic acid and the alkyl and arylsulfonyl groups and, if b denotes the carboxy group, the sulfonic acid amide group and the sulfonic acid amide groups substituted on the nitrogen atom by alkyl or aryl.

The dyes are made using the same methods as they are described in the '904,228 patent. Compared to those known from this patent However, the dyes according to the invention have copper-containing disazo dyes The advantage is that they have a better absorption capacity on both cotton and viscose own.

The new copper-containing disazo dyes have good solubility very good drawability for cotton and fibers made from regenerated cellulose and dye these textiles in lively bordeaux shades of very good lightfastness.

In the metal-free state, they correspond to the composition wherein b, B, R and W have the meanings given above.

The following examples illustrate the invention. The parts mean parts by weight. Example i 13.7 parts of i-aminobenzene-2-carboxylic acid are mixed in 80o parts of water and 23 parts of concentrated hydrochloric acid. The slurry, cooled to 0 to 5 °, is mixed with 6.9 parts of sodium nitrite. The suspension of the diazo compound obtained is added to a solution of 54.8 parts of the symmetrical urea of sodium 2-amino-5-oxynaphthalene-7-sulfonic acid, 16.8 parts of sodium bicarbonate and 300 parts of water. When the monoazo compound has formed, the reaction product is mixed with 26.5 parts of anhydrous sodium carbonate and then with the diazo suspension of 18.7 parts of i-amino-2-oxy-5-methylsulfonylbenzene. The finely divided disazo dye formed is first brought into solution at 80 ° to 85 ° by adding 160 parts of water and 7.4 parts of concentrated sodium hydroxide solution to the coupling compound and then separated out again from the solution using sodium chloride, filtered off and dried. For cleaning, the disazo dye can optionally be redissolved from hot water.

To convert it into the copper complex compound, the isolated disazo dye is dissolved at 80 ° to 85 ° in 480 ° parts of water and 35.5 parts of 25% ammonia. 54.4 parts of crystallized sodium acetate are then added to the dye solution and a solution of 50 parts of crystallized copper sulfate in 50 ° parts of water is added to it at 80 ° to 85 ° over the course of 30 minutes. The coppering compound is stirred for a further 60 minutes at the same temperature, then the deposited, copper-containing disazo dye is filtered off and dried in vacuo at 0 °. It pulls very well on cotton and fibers made from regenerated cellulose and dyes these textiles in lively bordeaux shades of very good lightfastness.

The identical dye is obtained by first using the monoazo compound from one mole of diazotized i-amino-2-oxy-5-methylsulfonylbenzene and one mole of the symmetrical one Urea from α-amino-5-oxynaphthalene-7-sulfonic acid, then this combined with i mole of diazotized i-aminobenzene-2-carboxylic acid and the resulting Subjected to disazo dye of the copper university.

The identical copper-containing dye is also obtained when the i-amino-2-oxy-5-methylsulfonylbenzene by the i-amino-2-methoxy-5-methylsulfonyl-benzene replaced and the disazo dye obtained subjected to the demethylating copper uni.

The copper plating methods used here are the same as those in the patent application S 43051 IVb / 22a are described.

In the example above, the ratio of the two is used Diazo components i: i. If this ratio is chosen differently from i: i, then more yellowish or more bluish tones are obtained.

The table below lists further disazo dyes which are obtained by coupling 1 mol of the symmetrical urea of 2-amino-5-oxynaphthalene-7-sulfonic acid with 1 mol of the diazo component (III) and 1 mol of the diazo component (IV). The amino compounds on which the latter two are based are listed in the table to identify the new disazo dyes, as are the shades of the dyeings obtained with the copper complex compounds on cotton. Hue of In-staining of the game diazo component (III) diazo component (IV) containing copper Disazo dye on cotton 2 i-Amino-2-oxy-5-methylsulfonylbenzene i-Amino-2-oxy-5-methylsulfonylbenzene Lebhaftbordo 3 like. I-Amino-2-oxybenzene-5-sulfonic acid like. 4 like. I-Amino-2-methoxybenzene-5-sulfonic acid like. i-Amino-2-oxy-3-chloro-benzene-5-sulfonic acid desgl. 6 i-Amino-2-oxy-4-methylsulfonylbenzene i-Amino-2-oxybenzene-5-sulfonic acid desgl. 7 i-Amino-2-oxy-5-phenylsulfonylbenzene i-Amino-2-methoxybenzene-5-sulfonic acid desgl. 8 i-Amino-2-methoxy-5-phenylsulfonylbenzene like. Hue of In-staining of the game diazo component (III) diazo component (IV) containing copper Disazo dye on cotton 9 i-Amino-2-oxy-5-ethylsulfonylbenzene i-Amino-2-oxybenzene-5-sulfonic acid desgl. io i-Amino-2-oxy-5-methylsulfonylbenzene i-Amino-2-carboxybenzene-4-sulfonic acid amide desgl. 11 the same. I-Amino-2-carboxybenzene-q.-sulfonic acid- methylamide like 12 the same. I-Amino-2-carboxybenzene-q.-sulfonic acid- phenylamide like

Claims (1)

PATENT CLAIM: Further development of the process for the production of copper-containing disazo dyes according to patent application S 43051 IVb / 22a, characterized in that one mole of the symmetrical urea of 2-amino-5-oxynaphthalene-7-sulfonic acid is mixed with one mole of the diazo compound in any order from an aminobenzene of the composition where B is hydrogen or methyl and W is an aliphatic or carbocyclic hydrocarbon radical, and on the other hand with i mol of the diazo compound from an amine of the composition bR-NH2, where b is oxy, methoxy or carboxy and R is a radical of the benzene series in which the substituent b and the N HZ group are in the ortho position to one another and which can be further substituted by the water-solubilizing group customary in azo dyes, with the exception, if b is oxy or methoxy, the sulfonic acid amide group and the sulfonic acid amide groups substituted on the nitrogen atom by alkyl or aryl groups , couples and treated the disazo dye obtained with a copper donor. Publications considered: German Patent No. 90q.228.