DE541943C - Process for the preparation of Kuepen dyes - Google Patents

Description

Process for the preparation of vat dyes In the patent 504 o 16 and in the additional patent 507 34 [¢ it was shown that new, very valuable vat dyes are obtained if benzanthronyl-i-aminoanthraquinones, which contain at least one acylamino group in their molecule, are acidic Treated condensing agents.

Insofar as they can be derived from (2-benzanthronyl-) i-aminoanthraquinone, these dyes can be converted into the basic structure of this series of dyes by replacing the acylamino group with hydrogen, which is a vat dye that turns dark green from a reddish-blue vat and has the following constitution: It has now been found that this dye and its derivatives can be obtained in a very simple manner if 2- (Bz-initrobenzanthronyl-) i-aminoanthraquinone or its derivatives are heated to a higher temperature in the presence or absence of solvents. The nitro group is split off with the formation of nitrous gases. So you get z. B. from your 2- (Bz-i-nitrobenzanthronyl-) iaminoanthraquinone, which can easily be prepared by condensation from Bz-i-nitro-2-chlorobenzanthrone and i-aminoanthraquinone, by heating to a higher temperature in a very pure state the basic body of this series of dyes, which in the example q. of additional patent 50734q. is described. Example ii Part 2- (Bz-i-nitrobenzanthronyl-) i-aminoanthraquinone (obtainable, for example, from Bz-i-nitro-2-chlorobenzanthrone and i-aminoanthraquinone in nitrobenzene at about zoo to 2 = 0 °) is given with = Heated 50 parts of nitrobenzene to the boil for several hours. The dye separates out in small crystals during the heating process, which, after the melt has cooled to 100 °, are sucked off and washed with warm nitrobenzene and alcohol. The new dye is thus obtained in shiny steel-blue needles which dissolve in concentrated sulfuric acid with a blue color and dye the vegetable fibers in very genuine dark green tones from a reddish blue vat. Instead of nitrobenzene, other suitable organic compounds, such as. B. nitronaphthalene; Naphthalene, benzophenone, etc., are used as solvents.

Example 2 3 parts of 2- (Bz-i-nitrobenzanthronyl-) i-aminoanthraquinone are heated in the lead bath for some time to 3oo to 33o °. Nitrous vapors develop and the red-brown condensation product takes on a greenish-black color. By Dissolving from sulfuric acid, the dye can be brought into dough form. He is right in its properties the same as the dye of Example i.

Example 3 In 80 parts of 2-nitro-1,4-dichlorobenzene at 100 ° x Part 2- (Bz-i-nitro-7-chlorobenzanthronyl-) i-aminoanthraquinone (available e.g. from Bz-initro-2, 7-dichlorobenzanthrone with 1 mol. i-aminoanthraquinone) and heated to the boil for about = hour. The initially red color of the solution goes gradually over brown olive into an intense green. After the melt has cooled 80 parts of nitrobenzene are added to 100 °, suctioned off at 50 ° and, as usual, worked up. The dyestuff, which contains chlorine, is thus obtained in very good yield in the form of a crystalline, dark green powder that is concentrated in Sulfuric acid with a blue color dissolves and from the violet-tinged blue vat the vegetable Dyes fiber in very real dark green tones.

A similar dye is obtained if, instead of the one in the example, mentioned condensation product the 2- (Bz-i-nitro-6-chlorobenzanthronyl-) i-aminoanthraquinone heated to a higher temperature.

Example 4 α-Nitronaphthalene melted in 100 parts is used in about 100 ° 5 parts of the condensation product from 1 mol. Bz-i-nitro-2-chlorobenzanthrone and i mol. i, 6-diaminoanthraquinone entered and heated to boiling. The first The red-brown solution color of the melt gradually becomes an intense emerald green. the The reaction is over as soon as the intensity of the green solution color no longer increases, which is the case after a short time. After the melt has cooled to ioo ° the same amount of cold nitrobenzene is added and the product is suctioned off at about 60 ° and washes with nitrobenzene and alcohol. The new dye is obtained as a black powder that dissolves in concentrated sulfuric acid with a blue color solves. Pouring the sulfuric acid solution into water gives a gray-blue color Dough that dyes the vegetable fibers in gray-blue tones from a blue vat.

Similar dyes can be obtained if one is in place. of abovementioned condensation product those from Bz-i-nitro-2-chlorobenzanthrone or Bz-i-nitro-2,6 or 2,7-dichlorobenzanthrone with another suitable diaminoanthraquinone heated to a higher temperature. Example 5 Naphthalene melted in 500 parts at about 100 parts 2- (Bz-i-nitrobenzanthronyl) i-amino-4-benzoylaminoanthraquinone (obtainable e.g. by condensation of 1 mol. Bzi-nitro-2-chlorobenzanthrone with i Mol. = -Amino-4-benzoylaminoanthraquinone) entered and boiled for a few hours heated. As soon as the dye formation has ended, the melt is left at 100 ° cool, diluted with 5oo parts of warm o-dichlorberizole, suctioned off at 80 ° and washes with warm o-dichlorobenzene until the filtrate turns pale green expire. The dye obtained is a small-crystalline, greenish-black powder, which dissolves in concentrated sulfuric acid with purple-red color and from blue Küpe dyes the vegetable fiber in beautiful olive green tones.

If, in place of the above-mentioned condensation product, one uses in which the individual components either by i-amino-5-benzoylarninoanthraquinone or are replaced by Bz-initro-2, 6- or 2, 7-dichlorobenzanthrone, is obtained one similar dyes.

Claims (1)

PATENT CLAIM: Further development of the method according to patent 504 o16, characterized in that 2- (Bz-i-nitrobenzanthronyl) i-aminoanthraquinones heated to a higher temperature in the presence or absence of solvents.