CH347918A - Process for the production of vat dyes of the acedianthron series - Google Patents

Description

  

      Process for the production of vat dyes of the acedianthron series The present invention relates to a process for the production of new dyes of the acedianthron series, which probably have the general formula
EMI0001.0006
    in which R is a five- or six-membered ring, in particular a benzene ring.

      The method according to the invention is characterized in that compounds of the general formula
EMI0001.0010
    treated with agents that bring about the ring closure to the ace- dianthrone.



  The compounds of the formula (2) used as starting materials for the present process can be obtained by condensation of the anchors of the formula
EMI0002.0001
    or carboxylic acids of the formula
EMI0002.0003
    with glyoxal or a glyoxal releasing agent such as glyoxal sulfate. The anthrone of formula (4) can either by reducing the corresponding anthraquinone with naszierendem What 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 solvent such as nitrobenzene, tetrachloroethane,

      in the presence of an acid anhydride, such as P205 or acetic anhydride, or acid chloride and / or sulfuric acid.



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



  While red-brown colorations are obtained with other derivatives of the acedianthrone, the colorations of the dyes obtained according to the process are surprisingly distinguished by very popular black-brown shades.



  Compared to the dye obtainable according to Example 3 of British Patent No. 551622, the dye obtained according to the method show the advantage of a significantly better drawability on cotton.



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



  <I> Example </I> 5 parts of bis- (1 ', 2'-benz-anthronylidene-10) are added to a solution of 60 parts of nitrobenzene, 5 parts of sulfuric acid at 96% per year and 13 parts of acetic anhydride ) Ethane, obtained by condensation of 2 moles of 1,2-benzanthrone-9 with 1 mole of glyoxal sulfate in glacial acetic acid. The mixture is heated to 100 within 11/2 hours, then cooled to 20, filtered and the filter material 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 tones and is excellently suited for printing on cotton or rayon.



  The bis (1 ', 2'-benzanthronylidene-10) -ethane used as the starting material can also be obtained by heating 2-benzylnaphthalene-2'-carboxylic acid with glyoxal sulfate in glacial acetic acid.



  The dye obtained can be dyed or printed according to the following rules. 1 part of the dye obtained in accordance with paragraph 1 is vat in 100 parts of water with the addition of 4 parts by volume of 30% 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% sodium hydroxide solution and 2 parts of sodium hydrosulfite in 2000 parts of water.

   In the dye bath 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 colored in violet-brown shades of excellent fastness properties.



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

 

Claims (1)

PATENT CLAIM Process for the production of vat dyes of the acedianthrone series, characterized in that compounds of the general formulas EMI0003.0001 wherein R means a five- or six-membered ring, treated with agents which cause the ring closure to the acedianthrone. SUBClaims 1. Process according to patent claim, characterized in that compounds of the given formulas are used as the starting point in which R is a benzene radical. 2. Process according to patent claim, characterized in that the compound of formula (1) is heated with concentrated sulfuric acid and acetanhydride in an organic solvent.