DE2844597A1 - METHOD FOR THE PRODUCTION OF AZO COLORS CONTAINING COPPER - Google Patents

Description

-κ- j

BAIER AKTIENGESELLSCHAFT

Central area

Patents, trademarks and licenses

5090 Leverkusen, Bayerwerk

Process for the production of copper-containing azo dyes

The invention relates to a process for the preparation of dyes of the general formula i!

0 Cu

in the

S is hydrogen, an acetyl, benzoyl or an optionally further substituted phenyl radical, η 1 or 2 and
X denote the azo and / or azoxy bridge,

characterized in that compounds of the general formula II

OH CH ₃ O

RHM ¹

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030017/02 9 3

II

284459?

in which E and η have the meaning given above, with a copper-releasing Treated Kittel and thereby in compounds of the general formula III

III

in the R and η the o. a. Have meaning, transferred and then reduced as usual.

Particularly valuable dyes of the general formula IV

IV

in which R _{1 stands} for 3-SO ₃ H, 4-SO ₃ H, I-COOH or 4-COOH and X has the meaning given above, compounds of the general formula V are obtained

SO ₅ H

in which R _{1 has} the meaning given above, treated with copper-releasing agents and thereby converted into compounds of the general formula VI

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VI

030017/02 9 3

in the R ₁ the ο. a. Has meaning, transferred and then reduced as usual.

The treatment of compounds of general formula II with copper-yielding agents is preferably carried out in the presence of 0.5-10 wt. Fo ammonia.

Compounds of general formula II are, for. B. those, as they are known in a manner from 5- ^ itro-2-aminoanisole by diazotization and coupling on compounds of the general formula VII, in which R and η the o. a. Have meaning, receive,

(HO ₃ S) _n

such as B. on l-hydroxy-e-aminonaphthalene ^ jo-disulfonic acid, l-hydroxy-8-aoetylaminonaphthalene-3,6-disulphonic acid, 4-hydroxy-7-aminonaphthalene-2-sulphonic acid, 4 ~ hydroxoxy-7-acetylaminonaphthalene-2-sulfonic acid, -4-hydroxy-7-benzoylaminonaphthalene-2-sulfonic acid, 4-hydroxy-7-phenylaminonaphthalene-2-sulfonic acid, 4-hydroxy-6-aminonaphthalene-2-sulfonic acid, 4-hydroxy-6-acetylaminonaphthalene-2-sulfonic acid, 4-hydroxy-6-benzoylaminonaphthalene-2-sulfonic acid, 4-hydroxy-6-phenylaminonaphthalene-2-sulfonic acid, 4 ~ hydroxy-6- (3'-carboxyphenylamino) -naphthalene-2-sulfonic acid, 4 ~ Hydroxy-6- (4'-carboxyphenylamino) -naphthalene-2-sulfonic acid, 4 ~ hydroxy-6- (3'-sulfophenylamino) -naphthalene-2-sulfonic acid, 4-Hydroxy-6- (4'-sulfophenylamino) -naphthalene-2-sulfonic acid.

Surprisingly, the method according to the invention is more economical than one of the methods described in German patents 636 358 or 694 9 & 5 or in German Auslegeschrift 15 44 559.

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0 30017/0293

In the following examples, "parts" mean parts by weight, "Percentages" are percentages by weight and the temperature data are degrees Celsius.

Example 1:

41> 7 parts of nitroazo compound 3- (4'-nitro-2'-methoxyphenylazo-) 4-hydroxy-6- (3 "-sulfophenylamino-) naphthalene-2-sulfonic acid are suspended in 600 parts ¥ ater at 8O ⁰ C heated and mixed with a solution of 20 parts of copper (II) sulfate peniahydrate in 50 parts of water and 50 parts of an aqueous ammonia solution containing 25 percent ammonia The mixture is heated to 95 ~ 98 ^ C and stirred for four hours at this temperature After the reaction has ended, the product is precipitated and isolated by adding 200 parts of sodium chloride A solution of 10 parts of glucose in 50 parts of water is then added over the course of five minutes, followed immediately by the addition of 150 parts of sodium chloride to precipitate and isolate the dye t. After drying, 37.6 parts of a black-blue powder are obtained which dyes cotton in blue-gray shades.

Example 2;

The same dye is obtained if instead of 41 »7 parts of the nitroazo compound from Example 1, the equivalent amount of the kro-2-aminoanisole in the coupling of diazotized 5-Ni " 4-Hydroxy-6- (3'-sulfophenylamino) -naphthalene-2-sulfonic acid obtained Suspension and 40 parts of copper (II) sulfate pentahydrate used.

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Claims (2)

Claims l. Procedure formula I: for the production of dyes of the general 0 - Cu 0, EM- (HO ₅ S) ΪΓ = Έ - (O in the E is hydrogen, an acetyl, benzoyl or an optionally further substituted phenyl radical η 1 or 2 and
X denote the azo and / or azoxy bridge, characterized in that compounds of the general formula BHET- in the E and η the ο. a. Have meaning with a copper-emitting Treated agents and thereby in compounds of the general formula EHN- in which E and η have the above meaning, transferred and this then reduced as usual. Le A 19 232 030017/0293 ORIGINAL INSPECTED / ti 2. A process for the preparation of dyes according to claim. 1 of the general formula 0 in which E _{1 stands} for 3-SO ₃ H, 4-SO ₃ H, 3-COOH or 4-COOH and Σ has the meaning given above, characterized in that compounds of the general formula CH ₃ 0 SO ₃ H in which E _{1 has} the above meaning, treated with copper-releasing agents and thereby in compounds of the general formula in which E _{1 has} the above meaning, transferred and then reduced as usual. 3 · A process for the production -of dyes of the general formula I according to claims 1 and 2, characterized in that the treatment with copper-yielding agents in the presence of 0.5 -. 10 percent fo ammonia is performed. Le A 19 252 0300 1 7/0293