DE122904C - - Google Patents

Description

IMPERIAL PATENT OFFICE.

JV * 122904 CLASS 22 «.

disulfonic acid.

In the patent specification 116200 a process for the preparation of ureas containing free hydroxyl groups of the naphthalene series is described, which consists in that, inter alia, on ß-amidonaphthol sulfonic acids in which the hydroxyl group is not ortho or meta to the amido group, such as . B. the ß ₁ -amido- «g-naphtholß ₄ -monosulfonic acid, the β j -amido- _{α 4 -naphtholß 3} -sulfonic acid etc., allows phosgene to act under certain conditions.

It has now been found that these ureas are valuable starting materials for preparation a new group of dyes. This is because these bodies are capable of both 1 and 2 mol of diazo compounds to couple while delivering dyes that stand out through their beautiful, for

Dye from: ι mol. Aniline + '

Aniline -f ~

ο -Toluidine +

ρ - toluidine -f-

m-xylidine -f-

ρ - xylidine -f

m-nitraline +

ρ - nitraline +

Acetyl-ρ-phenylenediamine -) -

ρ - phenetidine +

α-naphthylamine +

Amidoazobenzene - | -

ρ-toluidine and

α-naphthylamine

of the intermediate product from tetrazodiphenyl and

Salicylic Acid - [-

Tetrazodiphenyl -f-

Tetrazodiphenyl -f-

2 2 2 2 2 2 2 2 2 2 2
ι

Partly extremely clear, yellow-orange to blue Nuances, as well as characterized by a relatively very high acid fastness. Also own these dyes, especially those obtained with 2 moles of diazo compound, the surprising property, to dye unheated cotton directly.

The coupling with 1 mol. Diazo compound takes place most practically in a weakly acidic solution, that with 1 mol. Most smoothly in a soda-alkaline solution. When coupling with Mol. One and the same or two different diazo components can be used. Instead of 2 moles of a monoazo compound, 1 mole of a tetrazo compound can of course also be used.

In the table below are the nuances of a number of those available through our process Dyes listed:

dyes cotton yellow-orange
orange
red

yellowish red yellowish-red
red
orange
red orange
bluish red bluish red bluish red
bluish red

.0, 0

i-

J3 CL

α, α
co C

.5 '

%% ■

- t G
C <!

o 7 λ "

α «Ω-

U m

. co

"0

red-violet

red

violet

red-blue.

If the urea from the ßj - amido-α ₈ -naphtholß ₄ -sulfonic acid is replaced by the urea from the γ- amidonaphthol sulfonic acid listed above, the result is generally bluish-red to blue dyes.

/ Examples:
'■■'. ' Example i.

A solution of 50.4 kg of carbonyldioxydinaphthylamine disulfonic acid (from βj-amido-Ct ₃ -naphthol-β ₄ -monosulfonic acid) is poured into a weakly acetic acid solution of 50.4 kg of carbonyldioxydinaphthylamine disulfonic acid, with thorough stirring, in the usual manner from 9.3 kg Aniline produced, flowing in. After about 12 hours of stirring, the dye formation has ended. It is now warmed up, made alkaline with the required amount of soda, salted out, pressed and dried. The dye dyes unheated cotton in a weakly alkaline bath yellow-orange.

Example 2.

A diazobenzene chloride solution prepared from 18.6 kg of aniline is gradually added with thorough _{stirring to a solution of 50.4 kg of carbonyldioxydinaphthylamine disulfonic acid (from β x} -amido-ag-naphtholβ _{4 -monosulfonic acid) to which a sufficient amount of soda has been added.} The dye formation occurs immediately. After several hours of stirring, it is heated, salted out, pressed and dried.

The dye gives unheated cotton a clear, reddish tinge of orange.

Example 3.

21.4 kg of p-toluidine are usually diazotized and allowed to flow into a solution of 50.4 kg of carbonyldioxydinaphthylamine _{disulfonic acid (from β x} -amido-α ₄ -naphthol-βg-monosulfonic acid) to which excess soda has been added. After about 12 hours of stirring, it is warmed up, salted out, pressed and dried. The dye stains unheated cotton in clear, bluish red tones.

Example 4.

A diazo solution prepared in the usual way from 10.7 kg of p-toluidine is _{gradually added to a solution of 50.4 kg of carbonyldioxydinaphthylamine disulfonic acid (from βj -amido-α 3} -naphthol-β ₄ -sulfonic acid) to which excess sodium acetate has been added. As soon as the coupling has ended, the mixture is made alkaline with soda and a diazonaphthalene chloride solution prepared from 14.3 kg of α-naphthylamine is gradually run in. The mixture must finally react alkaline. After about 12 hours, the second coupling is also finished. It is warmed up, salted out, pressed and dried. The dye produces a red-violet on unheated cotton.

Example 5. '

A tetrazo solution prepared in the usual way from 18.4 kg of benzidine is stirred into a solution of 50.4 kg of carbonyldioxydinaphthylamine disulfonic acid (from β j - amido - α 3 - naphthol - β ₄ - sulfonic acid) to which excess soda has been added. The formation of the dye begins immediately and ends after stirring for several hours. The dye is then isolated as indicated above. It dyes unheated cotton red-blue.

Claims (1)

Patent claim:
Process for the preparation of orange to blue, unheated cotton azo dyes, which consist in the fact that the ureas described in patent 116200 are prepared from those β-amidonaphthol sulfonic acids which do not contain the amido and hydroxyl groups in ortho or meta positions to one another , with 1 or 2 mol. One and the same diazo compound, or with ι mol. Two different diazo compounds respectively. the equivalent amounts of tetrazo compounds.