DE274082C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

- M 274082 CLASS 22 «. GROUP

FARBENFABRIKEN vorm. FRIEDR. BAYER & CO.

in LEVERKUSEN b. COLOGNE.

Process for the preparation of azo dyes.

Addendum to patent 274081.

Patented in the German Empire on March 12, 1913. Longest duration: March 11, 1928.

A process for the preparation of azo dyes is protected by the main patent, which consists in the fact that one diazo compounds, diazoazo compounds, tetrazo compounds or intermediates of tetrazo compounds and a molecule of an azo dye component with substituted in the amino group by sulfo-o-oxycarboxylic acid radicals Aminonaphthols and their sulfonic acids

ίο couples.

It has now been found that, instead of the components mentioned, the through Condensation of the sulfochloride of 2-naphtholecarboxylic acid with ammonia, amines, phenols, Aminophenols, aminonaphthols and their sulfonic acids, carboxylic acids or their derivatives obtainable bodies from which the Carboxyl group can be split off, can use. These connections can before or after cleavage of the carboxyl group with one or two molecules of diazo compound be coupled. If one uses for coupling the compounds that make up the carboxyl group has not yet been split off, this happens during the coupling with the diazo compound.

Example 1.
"300 parts of 2-naphthol-6-sulfophenol ester

are dissolved with 40 parts of sodium hydrate and water, and excess soda is added. The diazo compound from 173 parts of o-sulfanilic acid is added with stirring. Most of the dye formed separates out and is filtered off. It forms dried a yellow-red powder and produces a clear orange on wool that is extremely fast to boiling.

Instead of the phenol ester, this coupling can also be carried out in a completely analogous manner use the homologues of the phenolic ester, also the naphthol esters, the sulfonic acids and Substitution products of these compounds, while on the other hand all possible Can introduce diazo compounds.

Example 2.
299 parts of 2-naphthol-6-sulfanilide

HO-

SO ₉ -NH-

45

55

are dissolved with 40 parts of sodium hydrate and water and the solution is still soda Excess added. The 203-part diazo compound is added to this solution Add 2-anisidine-4-sulfonic acid with stirring. After the coupling is complete, the Salt out the dye and filter off. When dried, it forms a brownish-red powder and produces a clear yellowish red on wool, which is differentiated from the 2-naphthol-

6-sulfonic acid is characterized by its very good millfastness.

One can, of course, instead of the condensation product of 2-naphthol-i-carboxyl-6-sulfochloride with aniline also the condensation products with other amines, such as naphthylamine, the homologues and substitution products of aniline, e.g. B. toluidine, methylaniline, sulfanilic acid, etc. as coupling components use Avie one on the other hand also the most varied of diazo compounds, diazoazo compounds, tetrazo compounds or intermediates of tetrazo compounds and a molecule of an azo dye component can use.

Example 3.
To 359 parts of 2-naphthol-6-sulfsalicylamide,

HO

^ -SO ₉ -NH-

COOH

-OH,

which are dissolved in excess soda, the diazo compound is released with stirring 223 parts of i-naphthylamine-4-sulfonic acid. To When the coupling is complete, the dye is salted out and filtered off. He produces on wool a red that turns into a bluish red with very good whale fastness when it is re-chromed transforms.

Similar dyes with the same good properties can be obtained if the condensation products of 2-naphtholecarboxyl-o-sulfochloride with other amino-oxycarboxylic acids, e.g. B. with the aminocresotinic acids or with derivatives thereof, e.g. B. the 5-sulfo-3-amino-6-oxybenzoic acid used as coupling components, or the condensation products with other aminophenols, e.g. B. with 4-chloro-2-aminophenol-6-sulfonic acid. On the other hand, you can of course all possible diazo compounds, z. B. diazo compounds, tetrazo compounds, etc.

use.

Example 4.

To 525 parts of the condensation product with i-amino-8-naphthol-3 · 6-disulfonic acid

HO-i

^L SO ₂ - NH OH

HO ₃ S- ¹

^L. SO, H

Dissolved with excess soda, the aniline obtained from 186 parts (2 molecules) is left Flow diazo solution. After the formation of the dye is complete, it is salted out, filtered off and dried. The dye gives wool a clear, yellowish scarlet color of good light, Sulfur and milled fastness. Similar dyes are obtained by replacing 1-amino-8-naphtol-3 · 6-disulfonic acid by the i-amino-8-naphthol ~ 4 · 6-disulfonic acid, while against the condensation products with 2-amino-5-naphthol-7-sulfonic acid are significantly more yellow in color give. Instead of the aminonaphthol sulfonic acids listed here, others can also be used Use aminonaphthol sulfonic acids, also condensation products with the aminonaphthols itself, e.g. B. with the i-amino-7-naphtol.

Claims (1)

Patent claim: Embodiment of the method for representation protected by the main patent of azo dyes, consisting in the fact that here the 2-naphthol-i-carboxylic acid by condensation of the sulfochloride with ammonia, amines, phenols, aminophenols, aminonaphthols and theirs Sulfonic acids or carboxylic acids or other derivatives available condensation products before or after the cleavage Carboxyl group used as the azo dye component.