DE123693C - - Google Patents

Description

PATENT OFFICE.

JVl 123693 CLASS 12 ο.

As in patent 116200 and its supplementary patent 116201 was shown, among other things, Urea containing free hydroxyl groups are respectively. Thiourea sulfonic acids der Naphthalene series obtained respectively by the action of phosgene. Thiophosgene on amidonaphthol sulfonic acids, in which the hydroxyl and amido groups are not in ortho or peri position to each other. The substances produced by this process have a symmetrical constitution, they have two identical amidonaphtol residues due to the carbonyl respectively Thiocarbonyl group combined into one molecule.

In the further course of the investigations on this subject we have now succeeded in also to get unsymmetrical ureas with free hydroxyl groups where two various amidonaphtol residues are linked to form a urea molecule.

These new, valuable bodies can be produced by making a mixture of the same Molecules of two different amidonaphthol sulfonic acids, in which hydroxyl and Amido group are not in ortho- or peri-position to one another, in the presence of one Hydrochloric acid binding substance of the action of phosgene respectively. Thiophosgene subjects. That mixed urea sulfonic acids and not mixtures of such substances are formed, It follows from this that when the solutions of the products obtained are fractionated with common salt, the individual fractions always show exactly the same properties and that those resulting from these individual fractions, the dyes provided all have exactly the same nuances and other characteristic features, exhibit.

The process for making the mixed urea sulfonic acids is entirely that of Main patent analog.

Examples.
I.

A mixture of 12 kg ß _t - amido -a ₃ ^ naphtol-ß ₄ -sulfonic acid and 12 kg ß _x - amido-a ₄ -naphtol-ßg-sulfonic acid is calcined with the addition of a solution of 25 kg. Soda was dissolved in approx. 200 l of water and phosgene was introduced in a weak stream at ordinary temperature with thorough stirring. The reaction is ended when

*) Former additional patent 116201.

an acidified sample gives no more precipitate and no longer absorbs nitrite. The mixed urea sulfonic acid is salted out with common salt, filtered off, pressed, and dried and ground.

The substance thus obtained turns a gray, slightly in water and diluted mineral acids soluble powder. The aqueous alkaline solution thereof, in contrast to the Starting materials no fluorescence. In acidic solution, the compound does not take off Nitrite, it combines with diazo compounds to form dyes, the unheated cotton able to stain directly.

The constitution belongs to the new substance:

OH

NH-CO-NH

OH

II.

To a calc with the addition of 25 kg. Soda-made solution of a mixture of 12 kg ß ₁ -amido-a ₃ -naphthol-ß ₄ -sulfonic acid and i2kgßj-amido-a ₄ -naphthol-ß ₃ -sulfonic acid in approx kg of thiophosgene allowed to flow in very gradually. The reaction is over when an acidified sample no longer absorbs nitrite. It is then acidified with hydrochloric acid and the new thiourine SO, H.

Sulphonic acid is salted out with table salt, filtered off and pressed. For further cleaning it is brought back into solution with cold water, filtered, and removed from the filtrate separated again with common salt, filtered, pressed and dried. The substance thus obtained is an almost white powder that is easily soluble in water and diluted acids. Alkaline aqueous. Solutions of the acid have no fluorescence. The connection has the constitution:

Oi?

NH CS - NH

OH

III.

In a mixture of 12 kg of ß _x -amido-a ₃ -naphthol-ß ₄ -sulfonic acid and 12 kg of Ct ₁ -arm'do-a ₃ -naphthol-ß ₄ -sulfonic acid with the addition of 25 kg of calc. Soda-made solution containing 200 to 300 liters of liquid is introduced into phosgene with thorough stirring in a slow stream until an acidified sample gives no more precipitate and no more nitrite

SO, H

NH S O, H.

records. Table salt is then added to near saturation, whereby the Urea sulfonic acid separates. The same is sucked off, pressed and dried. she will thus obtained as a gray powder which is easily soluble in water, dilute acids and alkalis is. Aqueous and alkaline solutions of the new acid show no fluorescence. In sour Solution, the compound does not absorb nitrite. She has the constitution:

O, H

OH

In a completely analogous manner, the corresponding mixed thiourea sulfonic acid turns out to be light gray Powder obtained if, instead of phosgene, thiophosgene is added to the mixture of the same

OH.

Molecules of the two amidonaphthol sulfonic acids mentioned has an effect.

The new compounds are to be used for the preparation of azo dyes.

Claims (1)

Patent claim: Modification of the methods of representation protected by patents π 6200 and 116201 from. ureas containing free hydroxyl groups respectively. Thioureas of the naphthalene series, consisting in the fact that one Obtaining unsymmetrical urea and Naphthalene series thiourea sulfonic acids in place of the amidonaphthol sulfonic acids used according to the main patent Mixture of two of these substances in molecular proportions in the presence a hydrochloric acid binding substance subjected to the action of phosgene or thiophosgene.