DE75469C - Process for the preparation of disazo dyes from / Jj-Amido-aj-naphtol - ^ - sulfonic acid - Google Patents

Description

IMPERIAL

PATENT OFFICE.

The amidonaphthols and their sulfonic acids have recently gained increased interest in the preparation of azo dyes. Sulphonic acids of these, namely the ftj a ₄ - (1 × 8-) and the β, a ₄ (2. × 8 or 1 ×. 7-) compounds have been found to be suitable for the preparation of valuable dyes.

The ßj a ₄ -amidonaphtol
OH

NH

In the form of its ß _B - sulfonic acid (patent no. 53076) when combined with benzidine etc. it leads to deep black colorants, the "diamine black" (patent no. 55648).

On the other hand, derived from the Ct ₁ ct ₄ amidonaphtol

OH NH

of Patent No. 55404 two different sulfonic acids from which both with diphenyl bases more or less blue substantive dyes deliver. They are inherently dull in tone, while their benzoyl derivatives are of a bright blue shade (see patents No. 54662 and No. 63064, also that Patent No. 62289).

Other sulfonic acids of Ct ₁ a ₄ amidonaphthol can also be used for the preparation of azo dyes, according to more recent patents.

It has now been shown that, in addition to these compounds, the as yet unknown P ₁ ctg-amidonaphtol is another

NH

OH

is added and, in the form of its ß ₄ -sulfonic acid, forms an excellent starting material for the preparation of substantive dyes, which differ in their properties from those described above, and in some cases very advantageously. The above-mentioned P ₁ -amido -Ot ₃ -naphthol-β ₄ -sulfonic acid can be converted into dyes in an alkaline solution of 2 molecules each with 1 molecule of the tetrazo compounds of diamidocarbazole, diamidodiphenylene ketoxime, tolidine and analogous diphenyl bases, without benzoylation being necessary from beautiful violet-red to blue nuances, which are of outstanding value due to these nuances themselves, as well as due to an unusual color intensity and excellent washing and lightfastness, and which moreover show perfect acid resistance.

Even those with the help of acet-p-phenylenediamine representable azo dyes of the type

can be converted into valuable nouns with the amidonaphthol monosulfonic acid mentioned Combine dyes, of which first which one may be described differs from the azo dye produced from acet-p-phenylenediamine and "-! - naphthol-aj-sulfonic acid derives.

The listed excellent properties of the new amidonaphthol sulfonic acid The theory could not foresee the resulting dyes, as it is in this class of the body does not yet have laws, and there are many amidonaphthol sulfo acids are not at all capable of association with diazo compounds.

From the _{disazo dyes already presented from P 1} a ₄ - and H ₁ a ₄ -amidonaphthol monosulfonic acid, the corresponding ones of the present patent differ as follows:

Diamido
carbazole Diamido
diphenylene
ketoxime Combina
Tolidine tion with:
Benzidine Dianisidine p-phenylene
diamine + O ₁ ¹
Naphtol-a ₂ -
sulfonic acid P ₁ a ₄ -Amidonaphtol-ß ₃ -
sulfonic acid
(Patent No. 55648) - - blue black black black blue - a _x a ₄ - amidonaphtol - a ₃ -
and a ₂ -sulfonic acid (see
Patents No. 54662 and
No. 63074) - - dull blue dull blue dull blue - Benzoyl derivatives of ^ a ₄ -
Amidonaphtol-a ₃ -sulfo-
acid (Patents No. 54662
and no.57394) - blue blue
(in ätzalk violet blue
alic bath green blue
e colored) - Benzoyl derivative of A ₁ a ₄ -
Amidonaphtol - a ₂ - sulfo-
acid (Patent No. 63074) - - - blue - - P ₁ Ct ₃ - Amidonaphtol - P ₄ -
sulfonic acid (present
Patent) purple brown violet red-violet violet red blue blue.

The β, -amido - « ₃ - naphthol - β _i - sulfonic acid is represented in such a way that at temperatures of about 160 to 180 ° C. that naphthylamine disulfonic acid is fused with alkalis which by further sulfonation of the P ₁ -naphthylamine ag- sulfonic acid is formed and described by Armstrong and Wynne (Proc. Chem. Soc. 1890, p. 128) and recognized as βj: a ₃ : β ₄ (2: 5: 7) acid. The action of the alkali very probably _{replaces the sulfo group in the ct 3} position with hydroxyl, according to which the amidonaphthol sulfonic acid shown has the constitutional formula

HO »S

NH "

OH

is attributable.

The representation of the dyes is illustrated by the following examples:

I. Dye from 1 Molecule Diamidocarbazole and 2 MolecUlen Amidonaphtholsulfonic Acid.

19.7 kg diamidocarbazole are in the form of the sulfuric acid salt according to the regulation of Patent No. 46438 converted to the tetrazo compound; the solution obtained runs into a completely alkaline solution of 48 kg of amidonaphthol sulfonic acid with stirring flow in. The combination is finished after a short time; they boil, salt out, filter, and praise and dries.

Used to represent the dyes from the other diphenyl bases given above instead of 19.7 kg of diamidocarbazole, the equimolecular amounts of those bases.

The coloring properties of the dyes, which are all easily soluble in water, result from the above compilation.

II. Dye from ι Molecül p-amidobenzolazo-a, -naphtol-aj-monosulfonic acid and ι Molecül Amidonaphthol sulfonic acid.

The according to the measure of Example I. in Patent No. 42814 from 15 kg of acetyl-ρ phenylenediamine and 25 kg of aj-naphtol-aa-monosulfosaurem Soda and subsequent saponification of the amidoazo bodies (p-amidobenzene-azo-a-naphthol sulfonic acid) is, as already described, diazotized with 7 kg of sodium nitrite to form a cold solution of 24 kg of amidonaphthol sulfonic acid and 100 kg of calcined soda in 1000 liters of water were added. After standing for a while, it is boiled, salted out, filtered, prefilled and dried.

Claims (2)

Patent Claims: 1. Process for the preparation of disazo dyes from ßj-amido -ctg-naphtol-ß ^ sulfonic acid, consisting in the fact that one either a) ι Molecule of the tetrazo compounds of the paradiamines used to represent substantive azo dyes to 2 Molecule ßj - amido - α ₃ - naphtholß ₄ sulfonic acid, or b) Molecule of the diazo compound of an amidobenzene - azo dyes of the formula NH " .N = N-X on ι Molecül of the amidonaphthol sulfonic acid mentioned
works in an alkaline solution. 2. The use of a) Diamidocarbazole, diamidodiphenylene ketoxime, tolidine, benzidine and dianisidine in which by claim ia), as well as that of b) amidobenzene - azo - Ct ₁ - naphthol- α ₂ sulfonic acid in the process protected by claim 1 b).