DE500175C - Process for the production of azo dyes - Google Patents

Description

Process for the preparation of azo dyes Few aromatic Amines give as diazo components by coupling with aryl amides of 2-oxynaphthalene-3-carboxylic acid Azo dyes of excellent lye boiling fastness with good light fastness at the same time.

It has now been found that the i-amino halogenated in the 6-position - 3 # 4 - dimethylbenzene dyes that meet the above requirements fully and with good lye boiling fastness a particularly excellent one Have lightfastness.

The 6-chloro-i-amino-3 # 4-dimethylbenzene is already from C 1 a u s (J. pr. 46, 11, 34) has been prepared by rearrangement of the 6-chloro-3 # 4-dimethylphenylmethylketoxime into the corresponding acetyl chloroxylide and saponifying this acetyl compound. It can be more easily obtained by chlorinating the acetyl compound or salts of the i-amino-3 # 4-dimethylbenzene or by replacing the amino group in the i-amino - 3 # 4 - dimethyl-6-nitrobenzene by chlorine and reduction of the nitro group.

The diazo compound of the base mentioned, coupled with 2-oxynaphthalene-3-carboxylic acid 5-chloro-2-methoxy-i-anilide or the 2-methoxy-i-anilide or the 2 # 5-dimetb; oxyi-anilide gives azo dyes from lively, neutral red to bluish red tones of particularly good lye boiling fastness and lightfastness. Examples e.g. The cotton fiber is made in a known manner with the following Treated primer solution: 4.5 parts by weight of 2 # 3-oxynaphthoic acid-4'-methoxy- i'-anilid, 9 parts by volume Türk1SChYOtÖl 5%, 9 parts by volume caustic soda 34 ° B6, 4.5 parts by volume of 3% formaldehyde are made up to 100 parts by volume with water. It is developed with the following diazo solution: 1.56 parts by weight of i-amino-3 # 4-dimethyl-6-chlorobenzene are dissolved with 2.6 parts by volume of hydrochloric acid 22'B6 and 0.72 parts by weight in water Sodium nitrite diazotized with ice cooling. After the diazotization is complete with 2 parts by weight of sodium acetate blunted, 2o parts by weight of table salt added and topped up to 11. The color, washed and soaped at the boil, is lively bluish red with very good fastness properties.

2. The cotton fiber is in the usual way with the following primer solution padded: 6 parts by weight of 2 # 3-oxynaphthoic acid-2'-methoxy-i'-anilide, 12 parts by volume Turkish red oil 5%, 12 parts by volume caustic soda 34 ° B6, 6 parts by volume formaldehyde 3 percent are made up to i 1. It will be compared to the one given in example i Diazolcsung developed. The dye, washed and soaped at the boil, is lively; very caustic scarlet red. 3. The cotton fiber will impregnated in a known manner with the following primer solution: 4.5 parts by weight 2 # 3-Oxynaphtho, esic acid-5'-chloro-2'-methoxy-i'-anilide, 9 parts by volume Turkish red oil 5 percent, 9 parts by volume caustic soda 34 ° Bz and 4.5 parts by volume formaldehyde 3 percent are padded to i 1. It is with the diazo solution given in Example i developed. The washed and soaped at the boil the color has a lively bluish cast Red is of excellent lye boiling fastness and particularly good light fastness.

4. The cotton fiber is applied in a known manner with the following primer solution treated: 4.5 parts by weight of 2 # 3-Oxynaphthoes, acid-4'-chloro-2'-methoxy-i'-anaide, 9 room parts Turkish red oil 5%, 9 room parts caustic soda 34 ° B6 and 4.5 room parts 3% formaldehyde is made up to 11. It is with the example i specified diazo solution developed. The washed and soaped at the boil dye represents a vivid bluish red with very good fastness properties.

5. The cotton fiber is in the usual way with the following primer solution padded: 4.5 parts by weight 2 # 3-oxyiiaphthoic acid-2 '# 5'-dimethoxy-il-aniiid, 9 parts by volume Turkish red oil 5%, 11.25 parts by volume caustic soda 34'B6 and 4.5 Parts of formaldehyde are made up to i l. The development happens with the diazo solution given in example i. The soaped color at the boil is lively bluish red of; good fastness properties.

6. The cotton fiber is in a known manner with the following primer solution padded: 12 parts by weight of 2,3-oxynaphthoic acid (3-naphthylamide, 36 parts by volume of sodium hydroxide solution 34 ° B6, 24 parts by volume of Turkish red oil 5 percent, 500 parts by volume of hot water made up to 1 liter with water. The development takes place with the in example i specified diazo solution. The soapy color is a vivid red of excellent fastness to chlorine and alkali and good fastness to light.

Claims (1)

PATPNTANSPRUCIi: Process for the preparation of azo dyes, thereby characterized in that i-amino-3 # 4-dimethylbenzene halogenated in the 6-position diazotized and coupled with an arylamide of 2-oxynaphthalene-3-carboxylic acid.