DE450819C - Process for the production of chromium-containing azo dyes - Google Patents

Description

Process for the production of chromium-containing azo dyes. It was found that new dyes are obtained if o-oxydiazo compounds are used with barbituric acid or their N-alkyl, N-aralkyl, N-aryl derivatives. The mordant dyes thus obtained dye wool from an acid bath in yellow to red and brown tones, which through Chromium plating in walk, potting and very lightfast, yellow to brown and red Pass over the colorations.

The main value of the new products is that they, with chromium-releasing Treated means, pass into new, acidic dyes, which on wool from acidic Create bath levels and real, yellow to orange, brown and red tones.

The barbituric acids in question here can be prepared quite generally by the action of urea or monoalkyl, monoaralkyl or monoaryl ureas on malonic acid esters. Example i. 233 parts of 4-sulfo-2-amino-i-phenol-6-carboxylic acid are, as usual, diazotized and added to a mixture of 134 parts of barbituric acid, 133 parts of 30 percent sodium hydroxide solution, 170 parts of soda and 1500 parts of water. The clutch works immediately; stir for a while to complete them. The dye formed is then filtered off. When dried, it forms an orange powder, dissolves in water with the addition of soda solution with a yellow-orange color and dyes wool from an acid bath in yellow tones, which become brown-yellow and real when chromium-plating. Example 2. 232 parts of 4-sulfo-2-amino-i-phenol-6-carboxylic acid are diazotized as usual and added to a solution of 160 parts of ethyl barbituric acid and 250 parts of soda in 2,000 parts of water. The mixture is stirred for a few hours. The dye formed is then filtered. When dried, it is an orange powder that dissolves in water with an orange color when soda solution is added and dyes wool from acid baths in yellow tones, which turn brown-orange when chromium-plating.

Example 3.

224 parts of q-chloro-2-aminophenol-5-sulfonic acid are, as usual, diacid and added to a solution of 230 parts of benzylbarbituric acid, 140 parts of 30 percent sodium hydroxide solution, 2,000 parts of water and 10o parts of soda. After a while, the formation of the dye has ended. The dye is then precipitated, filtered and dried. It forms a brown powder and dyes wool from an acid bath in yellow-brown tones, which become brick-red after chrome-plating.

Example 4.

224 parts of 4-chloro-2-amino-i-phenol-5-sulfonic acid are, as usual, diazotized and introduced into a solution of 214 parts of phenylbarbituric acid, 135 parts of 30 percent sodium hydroxide solution and 100 parts of soda in 2,000 parts of water. The dye starts to form immediately and after some stirring the diazo compound has disappeared. The dye formed is then, as usual, salted out, filtered and dried. It forms a red-brown powder, dissolves in water with the addition of soda solution with an orange color and dyes wool from acid baths in yellow tones, which turn orange when chromium-plating.

Example 5.

154 parts of 4-nitro-2-aminophenol are, as usual, diazotized and converted into a solution containing 203 parts of diphenylene-4-4'-dibarbituric acid (from ethyl malonate and urea from 1 mole. Benzidine and 2 moles of potassium cyanate) and 25o parts Soda, added to 2,000 parts of water. The dye, which forms very quickly, is filtered and dried. It forms a brown powder, dissolves in a dilute soda solution with a yellow color and dyes wool from an acid bath in orange tones, which change to brown when chromium plating.

Example 6.

32.8 parts of the dye from 2-aminoiphenol-4-sulfonic acid and barbituric acid are dissolved in 65o parts of boiling water and with a chromium formate solution accordingly i5.2 parts of Cr203 were added. It is refluxed for several hours and evaporated partially and wins the new chromium compound in the usual way. This forms a yellow-orange powder, dissolves in water with an orange-yellow color and dyes wool from an acid bath in real orange-brown tones.

Example 7.

A chromite solution is prepared in a known manner containing, per 100 parts by volume, 12.3 parts of Cr20g, 28 parts of caustic potash and 10 parts of glycerol, and 32.8 parts of the dye from 2-amino-i-phenol-4-sulfonic acid and Barbituric acid and refluxed for 10 hours. . The reaction mixture is then diluted with about 20 parts of water, separated from the excess chromium hydroxide, neutralized with mineral acid, and the new chromium-containing dye formed is obtained by evaporation or sifting. It is an orange-brown powder, dissolves in water with an orange-yellow color and stains wool from acidic baths to brown-orange.

Example B.

37.2 parts of the dye from 4-sulfo-2-amino-i-phenol6-carboxylic acid and barbituric acid are dissolved in 600 parts of water with a chromium formate solution 15.2 parts of Cr203 were added and the mixture was refluxed for a long time. The reaction mass is then partially evaporated and the dye formed is isolated in a known manner.- It is an orange-brown powder that dissolves in water with yellow-orange color and dyes wool from acid baths real orange.

Example g.

43.8 parts of the dye from 4-chloro-2-amino-i-phenol-5-sulfonic acid andbarbituric acid are dissolved in 8oo parts of a fluorochrome solution corresponding to 15.2 parts Cr203 dissolved and refluxed for a long time. The chromium-containing one formed Dye is obtained by sighting or evaporation. He puts an orange-brown Powder constitutes, dissolves in water with a yellow-orange color and dyes wool from acid Take a real orange bath.

Similarly, yellow to red and brown, chromium-containing Dyes from other o-oxyazo dyes, which differ from those in question here Derive barbituric acids.

The table above outlines the main characteristics of some products that can be manufactured according to the present process are specified.

Claims (1)

PATENT CLAIM: Process for the production of chromium-containing azo dyes, characterized in that o-oxydiazo compounds with barbituric acid or their N-alkyl, N-aralkyl, N-aryl derivatives and the mordant dyes thus obtained treated with chromium-releasing agents.