DE659095C - Process for the preparation of Kuepen dyes - Google Patents

Description

Process for the preparation of vat dyes It has been found that vat dyes of various shades with very good fastness properties can be obtained if the 4 ₧ 5-naphthoylene-2 '₧ 3'-quinoxaline peridicarboxylic acid or its anhydride is of the following form: and their derivatives and substitution products with compounds of the type RN H2, where R is hydrogen or the remainder of a hydrocarbon, such as. B. an aliphatic, alicyclic or aromatic hydrocarbon, or with aliphatic I ₧ 2-diamines, orthodiamines, I ₧ 8-naphthylenediamines and similar compounds are condensed.

Instead of the orthodiamines, orthonitroamines can also be used and after condensation has taken place, the compounds thus obtained are reduced, with in addition to the reduction, ring closure to the imidazole derivatives also takes place.

The vat dyes of yellow, brown, red, green etc. nuances have very good fastness properties. Examples I. 38 parts by weight of 7 '- (6') - chloro-4 ₧ 5-naphthoylene - 2 ₧ 3 '- quinoxaline peridicarboxylic acid anhydride (e.g. obtainable from the compounds mentioned in patent 6_58 203) "- are heated to a gentle boil for about ten hours with q, oo parts by weight of pyridine and 100 parts by weight of aniline. The dye formed is filtered off with suction while hot and washed with alcohol and water. Created It dissolves in concentrated sulfuric acid or hydrochloric acid with a red color and dyes cotton from a yellow-red vat in yellow tones.

The condensation products with other aromatic ones produce similar color shades and aliphatic amines.

2. 8 parts by weight of 7-chloronaphthoylene quinoxaline peridicarboxylic acid anhydride are mixed with 4 parts by weight of hydrochloric acid I ₧ 2-ethylene 3. 38 parts by weight of 7'-chloronaphthoylene quinoxaline peridicarboxylic acid anhydride are suspended as finely as possible in 400 parts by weight of glacial acetic acid and heated to boiling with II parts by weight of o-phenylenediamine for 5 hours. The dye formed is suctioned off hot, after drying it is a yellow microcrystalline powder and has the following constitution: diamine and the calculated amount of soda are heated to boiling in nitrobenzene. After 7 hours, the mixture is left to cool, filtered off with suction and washed with alcohol and then with water. The dye obtained is a brown powder which dissolves in concentrated acids with a red color and dyes cotton from a yellow-red vat yellow-brown. Its constitution is presumably the following, washed neutral with water and dried. It represents a red powder. which dissolves yellow-red in concentrated sulfuric acid and dyes cotton from yellow-red vat in a strong brick red with very good fastness properties. The following formulas are suitable for the constitution of the dye; a mixture of these two may also be possible. 4 7 parts by weight of 7'-chloronaphthoylenequinoxaline peridicarboxylic acid are heated to 170 to 180 ° for 2 to 3 hours with the calculated amount of 1-chloro-3 ₧ 4-diaminobenzene and 70 parts by volume of nitrobenzene. After it has cooled down, the dye is suctioned off and washed with alcohol. It dyes a red on cotton which is very similar to that described in Example 3.

5. 7'-chloronaphthoylene quinoxalinedicarboxylic acid anhydride, condensed with I-ethoxy-3 ₧ 4-diaminobenzene in the procedure of Example 3, results in a dye which, from a yellow-red vat of cotton, stains a very strong red-brown color and should have the following constitution: 6. 70 parts by weight of 7'-chloronapthoylenequinoxalinedicarboxylic acid are suspended in 150 parts by weight of glacial acetic acid with 50 parts by weight of sulfuric acid I ₧ 2-diaminonaphthalene and heated to 110 °. In the course of I hour, II parts by weight of soda are added in small proportions. The temperature is held at II o ° for a further 3 to 4 hours. The dye formed has the following constitution: is suctioned off hot and washed neutral with water. It dissolves in conc. Sulfuric acid olive-colored and dyes cotton from a yellow-red vat a bluish brown.

7. 38 parts by weight of 7'-chloronaphthoylenequinoxalinedicarboxylic acid are mixed with 25 parts by weight of sulfuric acid I. 8-diaminonaphthalene in 400 parts by weight of pyridine heated to II o ° for 10 hours. The reaction mass is filtered off with suction at 70 ° and washed twice with alcohol and water. The lyetried dye or isomer is an almost black powder that dissolves in concentrated sulfuric acid to a yellow-brown color and dyes cotton from a red vat olive-green. 8. 35 parts by weight of naphthoylene quinoxaline dicarboxylic acid or its anhydride are heated to boiling for a few hours with II parts by weight of o-phenylenediamine and 350 parts by weight of glacial acetic acid. The dye formed is filtered off with suction while hot, washed with hot glacial acetic acid and then with water and dried. It represents a red powder which dyes cotton in red tones; its constitution is as follows or isomer.

9. 40 parts by weight of 7 '- (6') - Äthoxynaphthoylenenchinoxalindicarbonsäure are in glacial acetic acid with 17 parts by weight of I-ethoxy-3 ₧ 4-diaminobenzene, as indicated in lead example 8, condensed and worked up. The dye or isomer dyes cotton a clear brown-red.

I0. 6 '₧ 7' - dichloronaphthoylene quinoxalinedicarboxylic acid results in a dye that condenses with I ₧ 2-dichloro-3 ₧ 4-diaminobenzene in the manner described, which dyes cotton very real red-brown and has the following constitution:

Claims (1)

PATENT CLAIM: Process for the preparation of vat dyes, characterized in that the 4 ₧ 5-naphthoylene-2 '₧ 3'-quinoxaline peridicarboxylic acid or its anhydride of the following formula: or their derivatives or substitution products with compounds of the R-NH2 type, where R denotes hydrogen or the residue of a hydrocarbon, or with allphatic I ₧ 2-diamines, orthodiamimes, I ₧ 8-naphthylenediamines or similar compounds or with orthonitroamines and that the with Use of orthonitroamiaxes can be reduced: