DE214658C - - Google Patents

Description

IMPERIAL

CLASS "22 0. GROUP 1.

in Basel ; ;

It has been found that that of 2-amino-5-naphthol-7-sulfonic acid derived p-amino-. phenyl-2-azimino-5-naphthol-7-sulfonic acid der formula

Ci _n i? _B.

-N-

N = N

-OH -SO ₃ H

■ Ν Η.

when coupling with diazo compounds, azo dyes yields which the valuable property own directly unstained cotton

15. to be colored in yellow-red to blue-red shades. As a result of the heteronuclear amino group present in the dye molecule, these dyes can be used both in substance and also diazotize further on the fiber and into one by coupling with azo components transfer a new range of azo dyes. Which in 'such a way on the fiber through Combination with non-sulfated components, such as. B. ß-naphtol produced colorations are characterized by good wash fastness and clear nuances.

The starting material, p-aminophenyl-2-azimino-5-naphthol-7-sulfonic acid, which has not been described anywhere so far is represented as follows:

104 parts of 2: 5: 7 naphthylamine disulfonic acid (neutral sodium salt) are used in about 600 parts Hot water dissolved, then 40 parts of sodium hydroxide solution (30 percent), 40 parts of crystallized Sodium acetate and 60 parts of 2: 4-Dinitro-ichlorbenzol added and the mixture during Heated under reflux for 8 hours. In order to terminate the condensation one then sets Gradually add 16 parts of soda and cook for another hour. You let it cool down and isolates the precipitated sodium salt of dinitrophenyl - 2 - naphthylamine-5: 7-disulfonic acid by filtering and pressing ..

70.5 parts of the dinitrophenylic acid thus prepared are then mixed with 120 parts of alcohol stir well, after which you add a solution to the pulp, ... possibly with external cooling of 60 parts of crystallized sodium sulfur and 13.2 parts of chlorammonium in 30 parts Lets water run in. The mixture is then heated to about 50 ° for as long as until an acidified sample no longer shows a yellow color when treated with nitrite, but instead provides a slightly reddish colored solution of the azimide. It is then allowed to cool, whereby the disodium salt of p-nitro-o-aminophenyl-2-n'aphtylamine-5: 7-disulfonic acid crystallized in the form of red-colored leaflets.

The sodium salt of the separated by filtration or pressing from the mother liquor Nitroaminophenyl acid is redissolved in water, mixed with sulfuric acid and ■ after and after so much sodium nitrite is added that iodine potash starch paper shows a lasting reaction. The solution of the 'nitroazimino compound thus obtained is then used in a known manner

reduced by boiling with iron filings and from the solution freed from iron by means of soda the aminophenyl - 2 - aziminonaphthalene - 5: 7 - disulfonic acid is acidified. It forms gray Needles and can be diazotized smoothly,

. . whereby a "colorless diazo compound" which is rather sparingly soluble in water is formed.

For the purpose of conversion into p-aminophenyl-2-azimino-5-naphthol-7-sulfonic acid 150 parts of aminophenylaziminonaphthalene disulfonic acid together with 150 parts of water and 300 parts of caustic potash in an autoclave heated to 180 to igo ° for 2 to 4 hours. the end the melt dissolved in water becomes p-aminophenyl - 2 - azimino -5 - naphthol-7 - sulfonic acid deposited by acidification using hydrochloric acid. It forms a gray, crystalline, Powder that is only sparingly soluble in water and, with: nitrous acid, also provides one sparingly soluble diazo compound, which when added to soda solution with itself couples to form a poorly soluble burgundy dye.

The conversion of the p-aminophenyl-2-azi-

«5 mino-5-naphthol-7-sulfonic acid in dyes explained by the following examples:

■ ■■ · Example r. ■ ·

■ 12.1 kg of m-xylidine are obtained using 7 kg of sodium nitrite and 30 kg of hydrochloric acid are diazotized in a known manner. The diazo solution is poured into a soda-alkaline, cooled solution of 36 kg of p-aminophenyl

. Pour in 2-azimino-5-naphthol-7-sulfonic acid, and dye formation occurs immediately. To The mixture is warmed up with some stirring, the dye possibly after adding a little salt filtered off, pressed and dried. He dyes unheated cotton in blue-red shades,

.40 which when diazotized on the fiber and subsequent coupling with ß-naphtol in clear Scarlet shades of good washfastness pass over.

In an analogous manner, dyes are represented using others Diazo compounds; for example, diazobenzene, o-diazotoluene provide dyes which when developing with S-Naphtol more yellowish tinge Produce tones as the xylidine dye; β-diazonaphthalene provides a burgundy red,; P-aminoacetanilide a blue red etc.

Instead of monodiazo bodies, tetrazo compounds can also be used as a combination

■ use and here either with two identical molecules aminoarylazimino-5-naphthol-7-sulfonic acid combine or else for the purpose of obtaining mixed tetrazo dyes by coupling ι mol. of the tetrazo compound with

> only ι mol. of the aminoarylaziminonaphthol sulfonic acid initially represent an intermediate and then this with any azo component continue to couple.

Example 2.

ii, 4 parts of m - azoxyaniline will be roughly 300 parts of water with the addition of 30 parts of hydrochloric acid dissolved and 7 parts of nitrite diazotized. The tetrazo solution is added to the soda-alkaline solution of 36 parts of aminophenylazimino-5-naphthol-7-sulfonic acid run in, whereby the dye is precipitated directly. It dyes unheated cotton orange Nuances.

Used instead of azoxyaniline Azoxytoluidine, azoxyanisidine, the result is products with a considerably more bluish tinge. With tetrazodiphenyl and its homologues are obtained from violet to blue dyes.

Example 3.

11.4 parts of azoxyaniline are tetrazotized and first with 16 parts of 2: 5-aminonaphtol-i: 7-disulfonic acid combined in an alkaline solution to form an intermediate. By adding an alkaline soda solution of 18 parts aminophenyl - azimino - 5 - naph.tol - 7 - sulfonic acid it is then converted into the mixed tetrazo dye. He dyes cotton red in direct dyeing and dyeing developed with β-naphtol, and the latter dyeing is distinguished by its excellent washfastness the end.

Mixed tetrazo dyes are represented in an analogous manner, if in place any of 2: 5-aminonaphthol-i: 7-disulfonic acid other azo components can be used, e.g. B. α- and ß-naphthol sulfonic acids, aminonaphthol sulfonic acids or their in the amino. ' group aeydilated derivatives etc.

100 Example 4.

25.5 kg of that obtained according to Example 1. Monoazo dyes are dissolved in 500 l of water, 3.5 parts of nitrite are added and followed by addition diazotized by 15 kg of hydrochloric acid. When the diazotization is complete, it is allowed to pour into a soda-alkaline Pour in solution of 23 kg i: 4-naphthol sulfonic acid, warm after stirring for a while and salt out the dye. It dyes unheated cotton directly in clear blue-red Tones. ·

Instead of 1: 4-naphthol sulfonic acid, any other azo components can also be used, such as. B. α- or ß-naphthol mono- 'and -polysulfonic acids, chloronaphthol sulfonic acids, aminonaphthol sulfonic acids and their derivatives aeydilierte in the amino group, whereby depending on the nature of the component used yellowish or bluish tinted products result. · <■■■'. - '■ ■ ■. ■■■■■ · '·> ■■■ iao

Likewise, instead of the monoazo dyes mentioned in Example 4 from xylidine other azo dyes, which can be prepared according to Examples 1 to 3, for further diazotization and coupling be subjected to azo components.

The dyes obtainable according to Example 4 can also be represented in the manner that the aminophenylaziminonaphthol sulfonic acid is first diazotized, then with a Azo component couples and the resulting monoazo dye subsequently with a diazo compound combined.

Claims (1)

Patent claim: Process for the preparation of substantive azo dyes, consisting in that one p-aminophenyl-a-azimino-s-naphtol ^ - sulfonic acid combined with diazo or tetrazo compounds and the resulting dyes either in substance or on the fiber is further diazotized and coupled with azo components or to that of diazotized ρ - aminophenyl - 2 - azimino - 5-naphthol-7-sulfonic acid produced monoazo dyes act a diazo compound »5 leaves. BERLIN. PRINTED IN THE REICHSDRUCKEREI.