DE1104092B - Process for the production of dyes of the acedianthrone series - Google Patents

Description

GERMAN

The present invention relates to new dyes of the acedianthrone series, which are likely to be the general formula

Method of manufacture
of vat dyes
the row of acedianthrones

(i)

correspond, in which R denotes an optionally substituted benzene radical.

These dyes are obtained by using compounds of the general formula

Applicant:
CIBA Aktiengesellschaft, Basel (Switzerland)

Representative: Dipl.-Ing. E. Splanemann, patent attorney, Hamburg 36, Neuer Wall 10

Claimed priority:
Switzerland from October 4, 1956

Dr. Armin Caliezi, Basel (Switzerland),
has been named as the inventor

or carboxylic acids of the formula

or

treated with means that bring about the ring closure to the acedianthron.

The compounds of the formula (2) used as starting materials for the present process can be obtained are made by condensation of the anthrones of the formula

(4)

with glyoxal or a glyoxal releasing agent such as glyoxal sulfate. The anthrone of formula (4) can either by reducing the corresponding anthraquinone with nascent hydrogen or by Treating a compound of formula (5) with a dehydrating agent, such as. B. sulfuric acid or Hydrogen fluoride.

The compound of the formula (3) can be obtained by treating the compound of the formula (2) with alkaline condensing agents, for example with an alkali hydroxide.

The ring closure of the compounds of the formulas (2) or (3) to the acedianthrones can be carried out according to the usual methods by heating with acidic condensing agents such as aluminum chloride, sulfuric acid, chlorosulfonic acid, preferably in the presence of an oxidizing agent such as persulfuric acid, sulfur trioxide, or in an organic Solvents such as nitrobenzene, tetrachloroethane, in the presence of an acid anhydride or acid chloride such as P ₂ O ₅ , or acetic anhydride and / or sulfuric acid.

109 559/483

The compounds of the formula (1) obtained according to the process are valuable vat dyes which are for dyeing a wide variety of materials, especially for dyeing and printing fibers from natural and regenerated cellulose and also as pigments.

While red-brown colorations are obtained with other derivatives of the acedianthrone, the Surprisingly, the colorings of the dyes obtained according to the process are due to the highly valued black-brown Sounds off.

Compared to the dye obtainable according to Example 3 of British Patent 551 622, they show according to the process received the benefit of significantly better drawability on cotton.

In the following example, unless otherwise stated, parts are parts by weight and percentages Percentages by weight and temperatures are given in degrees Celsius.

example

20th

In a solution of 60 parts of nitrobenzene, 5 parts of 96% sulfuric acid and 13 parts of acetic anhydride, 5 parts of bis (l ', 2'-benz-anthronylidene-10) ethane, obtained by condensation of 2 moles of 1,2- Benzanthron-9 with 1 mol of glyoxal sulfate in glacial acetic acid. The mixture is ^{heated to 100 ° for 1 1 1} ₂ hours, then cooled to 20 °, filtered and the filter residue is washed with nitrobenzene, alcohol and water. A black-brown powder is obtained which dyes cotton from an olive-brown vat in real violet-brown shades and is excellently suited for printing on cotton or viscose.

The bis (l ', 2'-benzanthronylidene-10) ethane used as the starting product can also be obtained by heating 2-benzylnaphthalene-2'-carboxylic acid with glyoxal sulfate in Glacial acetic acid can be obtained.

The dye obtained can according to the following rules colored or printed:

1 part of the dye obtained according to paragraph 1 revatted in 100 parts water with the addition of 4 parts by volume of 30 ° / ₀ sodium hydroxide solution with 2 parts of sodium hydrosulfite at 45 °. The stock vat thus obtained is added to a solution of 4 parts by volume of 30 ° / ₀ sodium hydroxide solution and 2 parts of sodium hydrosulfite in 2000 parts of water. In the dyebath thus obtained, 100 parts of cotton are dyed for one hour at 40 to 50 ° with the addition of 10 parts of sodium chloride. The cotton is then squeezed off, oxidized in the air, rinsed, acidified, rinsed again and soaped at the boil. It is dyed in violet-brown shades with excellent fastness properties.

200 parts of the finely divided dye obtained in accordance with paragraph 1 are mixed with 100 parts of water and 600 parts a potash thickening (made from 90 parts of wheat starch, 330 parts of water, 100 parts of glycerin, 140 parts British gum, 170 parts tragacanth gum and 170 parts potash) and 100 parts hydrosulfite mixed into a dough. A cotton cloth is printed with this. After the imprint is at moderate Heat dried and then steamed for 5 to 10 minutes in air-free, "moist" steam at 101 to 103 °, in Rinsed with running water and soaped at the boil. A strong, genuine violet-brown print is obtained.

Claims (3)

PATENT CLAIMS: 1. Process for the production of vat dyes of the Acedianthron series, dadutch marked, that in compounds of the general formulas where R is an optionally substituted benzene radical, by treatment with acidic condensing agents causes the ring closure to the acedianthron in a manner known per se. 2. The method according to claim 1, characterized in that the compound of formula (1) or (2) with concentrated sulfuric acid and acetic anhydride in an organic solvent, preferably Nitrobenzene, heated. 3. The method according to any one of claims 1 and 2, characterized in that one of such compounds of the formula (1), which were obtained by condensation of a compound of formula with glyoxal-releasing agents, one being called glyoxal-releasing agents Agent glyoxal sulfate can use. Considered publications:
British Patent No. 551,622;
U.S. Patent No. 2,108,144. When the application was announced, two coloring tables with explanations were laid out. 109 539/483 3.61