DE252839C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

V * 252839 CLASS 22b. GROUP

Process for the preparation of anthraquinone derivatives.

Addition to patent 238982 from July 28, 1910. *)

Patented in the German Empire on March 28, 1911. Longest duration: July 27, 1925.

In the patent 238982 a method for the preparation of condensation products is from o-Diaminoanthraquinones with aldehydes described, which as imidazoles of anthraquinone are to be understood:

NH

.N

(ortho)

-> ■ A <

^ NH ₉ .

"NH '

C-R,

A = anthraquinone residue.

It has now been found that one arrives at similarly constituted bodies if one the o-diaminoanthraquinones through the 0-aminooxyanthraquinones or the o-aminoanthraquinone mercaptans replaced. This creates the anthraquinone oxazoles and thiazoles.

H ₀

(ortho)

C-R

φ (ortho) ^ ^A C yC-R.

In patents 62703 and 68649
already described condensation products of ß-aminoalizarin with aliphatic aldehydes

Former additional patent 247246.

ben; however, these still contain the two unchanged hydroxyls of alizarin and therefore have a different constitution.

Anthraquinone thiazoles with a vat-coloring character have already been obtained by other means and in patent specification 229165.

The new bodies should also be used as dyes or as starting materials for Representation of such serve.

Example 1.

ι part i-amino-2 · 4-diox} 'anthraquinone is heated to boiling in 10 parts of benzaldehyde until the initially red colored solution turns yellow has become. It is then allowed to cool, the reaction product crystallizing Form.

The new substance, recrystallized from aniline or quinoline, turns orange Obtain crystal powder, its solution in concentrated sulfuric acid and in pyridine is colored orange. The solution in dilute sodium hydroxide solution is purple; is the sodium salt sparingly soluble in water.

If the dioxyaminoanthraquinone is replaced by the i-amino-2-oxyanthraquinone,

one holds the simple anthra-i · 2-oxazole. It forms yellow crystals, the solution of which in pyridine and concentrated sulfuric acid is yellow.

Example 2.

ι Part i-Oxy-2 · 4-diaminoanthraquinone is in 3 parts of nitrobenzene and 1 part of benzaldehyde with the addition of a few drops of piperidine heated to boiling until the solution, which was initially red in color, has turned yellow-brown. The reaction product crystallizes out on cooling.

Recrystallized from nitrobenzene, it is obtained in the form of brown crystals, whose Solution in concentrated sulfuric acid is initially orange, then green, in pyridine is orange. the vat made with alkaline hydrosulphite produces red dyeings on cotton, which turn orange when hanging in the air. The benzoyl compound of this substance, which turns from nitrobenzene in yellow Needles crystallized and reflected in pyridine as well as in concentrated sulfuric acid with yellow Color dissolves, is also a vat dye, which on cotton has a splendid yellow color of great authenticity.

Example 3.

A solution of 1 part of 1 · 2-dioxy-3-aminoanthraquinone (ß-Aminoalizarin) in 10 parts of nitrobenzene is heated for ₄ hour at 180 ° with 1 part benzaldehyde Z ^1. The reaction product crystallizes out on cooling. It can be recrystallized from nitrobenzene and orange-colored needles are obtained, which give orange solutions in pyridine or in concentrated sulfuric acid and blue-colored solutions in dilute sodium hydroxide solution. The substance does not stain either on the stain or in the vat.

Example 4.

ι part ι · 5 - diamino- 2 · 4 · 6 · 8-tetraoxyanthraquinone are in 10 parts of benzaldehyde with the addition of a drop of piperidine as .45 The condensing agent is heated to the boil until the solution is initially blue-red in color has turned wine red. The condensation product then separates out on cooling. The substance obtained dissolves in Sulfuric acid (66 ° Be.) Orange, in pyridine wine-red. The solution in concentrated sulfuric acid When boric acid is added, it turns an intense green color when heated. The alkali salts of the substance are very poorly soluble.

Example 5.

A solution of 2 · 4-Dioxy-i-aminoanthraquinone in 5 parts of nitrobenzene is 2 parts Paraformaldehyde added and heated to the boil until the initially blue-red Solution has turned reddish yellow. After adding alcohol, it separates when it cools. the Reaction product from, its solution in pyridine yellow-brown, in concentrated sulfuric acid is colored orange.

Example 6.

5 parts of 1 - aminoanthraquinone - 2 - mercaptan are mixed with 50 parts of benzaldehyde and 2 parts Zinc chlorine is heated in a water bath until the melt has turned yellow. After diluting With alcohol, the thiazole separates out in yellow crystals, which are filtered off with suction and washed with alcohol and water. Forms recrystallized from nitrobenzene there are yellow needles, which are found in pyridine as well as in concentrated sulfuric acid with yellow ones Dissolve paint.

Similar products are obtained when using other o-aminooxyanthraquinones or 0 - Aminoanthraquinone mercaptans or their derivatives, as well as other aliphatic or aromatic ones Aldehydes.

Claims (1)

85 patent claim: Modification of protected by Letters Patent 238982 method for the preparation of anthraquinone derivatives, is sawn _go standing, characterized in that the used there o-diaminoanthraquinones replaced here for purposes of illustration of Anthrachinonoxazolen or Anthrachinonthiazolen by o-Aminooxyanthrachinone or o-Aminoanthrachinonmerkäptane.