DE82774C - - Google Patents

Description

IMPERIAL

PATENTAM

In the patent specification no. 40893 is shown first, to a diazo compound DAF Dioxynaphtalinsulfosäuren, specially that of Dioxynaphtalindisulfosäure which is obtained by heating naphthalene with strong fuming sulfuric acid at about 150 ⁰ and following it, fusing the Naphtalintetrasulfosäure thus formed, besides having 1 Mol. And to combine with 2 moles of diazo compounds.

The preparation of analogous dyes from 2 mol. Diazo compound and 1 mol. Ci ₁ a ₄ -dioxynaphthalene-ß ₂ ß ₃ -disulfonic acid is described in patent no. Similar dyes are obtained from the α, α ₄ -dioxynaphthalene monosulfonic acid S by the method of addendum - patent no.

The method of the above patent no. 40893 results in disazo dyes which for that reason alone have less value than they represent mixtures of dyes, since they are them underlying dioxynaphthalene disulfonic acid according to the more recent investigations from a Mixtures of two isomeric acids consists.

According to the method of the above-mentioned patents no. 59161 respectively. 73170 won Dyes produce different nuances on ordinary wool than on chromed wool, and their whale fastness, of which the patent specifications in question do not mention anything, is both relatively small on ordinary as well as chromed wool.

It has now been found that the β, β, -dioxynaphthalene-βg-monosulfonic acid is likewise has the ability to react with 2 moles of the same diazo compound or with 1 mole each. to combine two different diazo compounds, whereby dyes are formed, which the dyes of Patent Nos. 59161 and 73170 are superior in that they have the same, and mainly deliver brown nuances and meet all requirements with regard to their mill fastness suffice.

Because of these properties, the new dyes are of general use capable, especially when it comes to the production of real dyeings and a Subsequent chromizing is necessary, since, as already mentioned, in the latter case the original nuance is not changed.

These new dyes, which are obtained either from 2 moles of the same diazo compound or from 1 mole each of two different diazo compounds, can advantageously be carried out by adding 2 moles of a diazo compound to 1 mole. _2- dioxynaphthalene-β ₃ -monosulphonic acid is expediently allowed to act in an alkaline solution, or 1 mol of the last-mentioned acid is first coupled with 1 mol of a diazo compound, preferably in a weakly acetic acid solution, and, after making it alkaline, 1 mol of another diazo compound for the action get there. It is precisely these latter so-called mixed disazo dyes that are of particular technical importance according to the investigations made. ,

Examples:

I. Dye from 2 mol. Aniline + 1 mol. P ₁ ßo -dioxynaphthalene-ßg-monosulfo-

acid.

The diazobenzene solution obtained from 18.6 kg of aniline is run into an alkaline solution of 27 kg of the sodium salt of β, β, - dioxynaphthalene - β ₃ -monosulfonic acid. The sparingly soluble dye precipitates out immediately.

He dyes chrome-stained wool in mill-proof brown-black to black nuances.

If, in the above examples, the homologous or is used instead of aniline analogous amines of the benzene or naphthalene series result in similar dyes. Man can also allow the diazo products of two different amines to act, with brown, brown-black ones as well until black dyes are obtained.

The Use of Diazo Compounds of Substituted Amines of the Benzene and Naphthalene Series is described in Examples II to VII below.

II. Dye from the same molecules ρ - sulfanilic acid, p-nitroaniline -) - ß ₁ ß ₀ -dioxynaphthalene-ß ₃ -monosulfonic acid.

The obtained from 17.3 kg of ρ-sulfanilic acid The diazo compound is dissolved in a solution of 27 kg of the sodium salt acidified with acetic acid the ßj ßo-dioxynaphthalene-ßg-monosulfonic acid registered. After the coupling is completed, it is made alkaline and then one off 13.8 kg of p-nitroaniline shown diazonitrobenzene solution were added. The dye falls and is isolated by known methods.

It dyes chrome-stained wool really brown.

III. Dye from the same Molecule η O ₁ -Naphthylamine-α ₂ -monosulfonic acid, a- Naphthylamine -f- ß, ß ₂ -Dioxynaphthalene-

ß ₃ -monosulfonic acid.

22 kg of naphthoic acid are diazotized in a known manner. The resulting diazo compound is coupled in acetic acid solution with 27 kg of ß, ß ₂ -dioxynaphthalene-ß ₃ -monosulfosaurem sodium. After making the mixture alkaline, a diazonaphthalene solution obtained from 14.3 kg of a-naphthylamine is added.

The disazo dye precipitates out as a black precipitate and is filtered off and Drying isolated.

The dyestuff thus obtained dyes ordinary and chromed wool in green, millfast Tones while the above is composed of 1 mole of naphthylamine sulfonic acid and 1 mole of dioxynaphthalene sulfonic acid Intermediate product preserved on chrome-stained wool, brown-violet, in the Walke provides nuances changing to yellow-brown.

.. IV dye from every 1 mole of p-amidophenol, aniline, and S ₁ ß ₂ - Dioxynaphtalin-ß _ä -monosulfosäure.

10.9 kg of p-amidophenol are diazotized in the usual way with 7 kg of sodium nitrite, and the diazo compound thus obtained is added to an aqueous solution of 26.2 kg of the sodium _{salt of β, β 2} -dioxynaphthalene-β ₃ -monosulfonic acid mixed with acetic acid. The coupling, which begins immediately, is over after a while. It is now made alkaline by means of soda or sodium hydroxide solution and a solution of diazobenzene chloride prepared from 9.3 kg of aniline is added. As soon as the formation of the dye is complete, the dye is completely precipitated by means of common salt and isolated in a known manner by filtering, pressing, and drying.

The same produces red-brown tones on chrome-stained wool.

V. Dye composed of 1 mol each of o-anisidine, ßj - naphthylamine - ß ₄ - monosulfonic acid and ßj ß, - dioxynaphthalene - ß ₃ - monosulfonic acid.

The diazoanisole solution prepared from 12.3 kg of o-anisidine is added to an aqueous solution of 26.2 kg of βj β ₂ -dioxynaphthalene-β ₃ -monosulfonic acid soda to which acetic acid has been added. As soon as the coupling is complete, the mixture is made alkaline by adding soda or sodium hydroxide solution and the _{diazo compound obtained by diazotizing 22.3 kg of β-naphthylamine-β 4} -monosulfonic acid is then added.

The dye is isolated by salting out, filtering off, pressing, and drying. Same dyes chromed wool gray-black.

VI. Dye from the same molecules amidoazobenzene monosulfonic acid, m-nitroaniline and ß, ß. ₂ -dioxynaphthalene-8 ₃ -

monosulfonic acid.

The diazoazobenzene monosulphonic acid prepared from 29.9 kg of amidoazobenzene monosulphonic acid is allowed to run into a solution of 26.2 kg of βj β _o -dioxynaphthalene-β ₈ -monosulphonic acid sodium. The coupling is completed in a short time. After making it alkaline by means of soda or sodium hydroxide solution, a solution of m-diazonitrobenzene made from 13.8 kg of m-nitroaniline is added.

The finished dye is salted out, filtered off, pressed and dried.

On chrome-stained wool, it delivers reddish brown nuances.

VII. Dye from the same molecules of p-amidophenol disulfo acid,

p-nitroaniline and ßj ß ₂ -dioxynaphthalene-

ß ₃ -monosulfonic acid.

31.5 kg of p-amidophenol disulfonic acid are diazotized with 7 kg of nitrite and the solution of diazophenol disulfonic acid thus obtained is converted into a solution of 26.2 kg of β, β mixed with acetic acid. ₂ -dioxynaphtalinmonosulfosaurem soda registered. As soon as the coupling is complete, it is made alkaline and then the solution of p-diazonitrobenzene corresponding to 13.8 kg of p-nitroaniline is added. The dye formation is completed in a short time. The dye is isolated by salting out, filtering off, pressing, and drying.

The same creates gray-tinged brown nuances on chrome-stained wool.

In a manner analogous to that described in the preceding examples, the other dyes are obtained if, instead of the diazo compounds used there, 2 moles of the same diazo compounds or 1 mole each of two different diazo compounds from substituted amines, such as amidophenols, amidophenol ethers, amidoazo compounds of benzene - and naphthalene series respectively. from sulfo- or carboxylic acids of amines of the benzene or naphthalene series and the same combined with ι mol. ß, ß ₂ -dioxynaphthalene-ß ₃ -monosulfonic acid.

The following table summarizes those nuances which are typical Representatives of the disazo dyes obtainable by the above process on chrome-stained Wool can be produced in weaker colors.

2 moles. Diazot. aniline Brown black 2 moles. Diazot. p-nitroaniline Brown ι Mol. diazot. Aniline and)
ι - - p-amidosalicylic acid) blue black ι Mol. diazot. m-amidobenzoic acid and)
ι - - p-toluidine J. Brown black ι Mol. diazot. "p-sulfanilic acid and)
1 - - p-nitroaniline j Brown ι Mol. diazot. a ₁ -naphthylamine-a ₂ -nionosulfonic acid and)
ι - - a-naphthylamine ■ J green ι Mol. diazot. ß ^ naphthylamine-ßrj-monosulfonic acid and)
ι - - ß-naphthylamine J greenish black ι Mol. diazot. p-amidophenol and)
ι - - Aniline J. red-brown ι Mol. diazot. o-anisidine and)
ι - - ß ₁ -naphtylamine-ß ₄ -monosulfonic acid J grey black ι Mol. diazot. Amidoazobenzene monosulfonic acid and)
ι - - m-nitroaniline) reddish brown ι Mol. diazot. p-amidophenol disulfonic acid and)
Vi- - p-nitroaniline \ grayish brown.

If more concentrated dyebaths are used, brown-black, green-black to pure black nuances.

The nuances created by means of these new dyes are due to their authenticity especially excellent against fulling and against alkalis.

Claims (1)

Patent Claims: i. Process for the preparation of milled and alkali-proof disazo dyes for wool from ßj ß ₂ - dioxynaphthalene - ß ₃ - monosulfonic acid, consisting therein; DAF to 2 mol. of the same diazo compound or per 1 mol. of two different diazo compounds with 1 mol. of the above ßj ß ₂ -Dioxynaphtalin-ß combinirt ₃ -monosulfosäure, wherein the BEZW of amines, Amidophenolen, Amidophenoläthern, Amidoazoverbindungen the benzene or Naphtalinreihe. the diazo products which can be prepared from sulfo or carboxylic acids of these components are used. The particular embodiments of the method protected by claim 1 L.
using ι mol. ß _; ß "-Dioxy- -monosulfonic acid and \
g) ι mol. diazot. ßj-naphthylamine-ßg- naphthalene-ß. diazot. Aniline, monosulfonic acid and a) 2 moles p-nitroaniline, I. ß-naphthylamine, b) 2 Aniline and h) ι p-amidophenol and c) ι p-amidosalicylic acid, I. Aniline, I. m-amidobenzoic acid i) ι o-anisidine and d) ι and I. ßj-naphthylamine-ß ₄ - p-toluidine, monosulfonic acid, I. p-sulfanilic acid and k) ι Amidoazobenzene mono e) ι - p-nitroaniline, sulfonic acid and I. aj-naphthylamine - ^ - I. m-nitroaniline and f) I - monosulfonic acid and 1) .- p-amidophenol disulfo a, -naphtylamine, acid and I. 1 p-nitroaniline. BERLIN. PRINTED IN THE REICHSDRUCKEREI.