DE248655C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

- M 248655 CLASS 22 b. GROUP

Addition to patent 17506g from January 10, 1905. *)

Patented in the German Empire on July 9, 1910. Longest duration: January 9, 1920.

The preparation of arylaminoanthraquinones from aminoanthraquinones and halobenzenes is protected by the main patent. In the two additions 215294, class 22 b, and 230409, class 22 b, vat-coloring arylaminoanthraquinones are also described, which are obtained by condensation of 2 mol. Of an aminoanthraquinone with 1 mol. Dihalobenzene or dihalodiphenyl.
It has now been found that vat dyes are also obtained if bodies which represent a linkage of two halobenzene radicals by O, S or NH are condensed with 2 moles of an aminoanthraquinone.

Example 1.

A mixture of 10 parts of dibromodiphenyl ether (by bromination of diphenyl ether, according to Annalen 15g, p. 210, can be displayed), 17 parts of alpha-aminoanthraquinone, 20 parts of dehydrated sodium acetate and 1 part of copper chloride is boiled in 170 parts of nitrobenzene for 8 hours with stirring. The reaction product separates out when the melt cools, it is isolated by suction and one after the other washed with nitrobenzene, alcohol and hot water.

This gives red-brown crystals that dissolve in higher-boiling organic solvents, like nitrobenzene, pyridine, dissolve fairly easily with cherry-red color when heated. Their solution in concentrated sulfuric acid is pale yellow-green in color; upon addition of Formaldehyde turns them 'intense blue. The red-brown colored hydrosulfite vat becomes Cotton dyed in strong bluish red tones.

Example 2.

10 parts of p-p-dichlorodiphenyl sulfide (shown from thioaniline by exchanging the amino groups for chlorine) with 18 parts α-Aminoanthraquinone, 20 parts of sodium acetate and ι part of copper chloride in 180 parts of nitrobenzene Heated to the boil for 10 hours while stirring. Isolation of the condensation product takes place analogously to Example 1. It is brown-red crystals, which are in Dissolve nitrobenzene as well as in pyridine with a dark red color. Your almost colorless solution in concentrated sulfuric acid turns an intense blue when formaldehyde is added.

With alkaline hydrosulfite, the compound provides a red-brown vat from which strong blue-red nuances are obtained on cotton.

The reaction proceeds in a completely analogous manner when using other aminoanttirachinone derivatives.

If one condenses z. B. the halogen compounds of the above examples with 2 mol. I-Ben-

*) Earlier additional patents: 215294 and 230409.

Claims (1)

zoylamino-4-aininoanthraquinone is obtained Vat dyes, which give strong blue colors on cotton. Example 3. A mixture of 10 parts of p-p-dibromodiphenylamine, 16 parts of α-aminoanthraquinone, 15 parts of dehydrated sodium acetate and ι part of copper acetate is mixed with 130 parts of nitrobenzene Boiled for 6 hours while stirring. The reaction product isolated analogously to Example 1 dissolves in concentrated sulfuric acid with a pale green color. Upon addition of Formaldehyde turns the solution deep blue. Dissolves in boiling aniline, nitrobenzene, pyridine the connection turns out fairly easily with reddish-purple color. From the red-brown cold Hydrosulfite vat gives violet dyeings on cotton. Example 4. 25 parts of 2 x 7-dibromoxanthone [Journ. Chem. Soc. 43, p. 193 (Perkin), Annalen 254, p. 284 (Graebe)], 30 parts of a-aminoanthraquinone, 20 parts of sodium acetate and 1 part of copper carbonate are boiled in 500 parts of nitrobenzene for 2 hours with stirring. That after cooling off The suctioned product is washed with alcohol and hydrochloric acid-containing water and dried. It is a dark red powder that turns into a green solution in concentrated sulfuric acid there, which when poured in water yields burgundy flakes. From alkaline Hydrosulfite vat is dyed cotton in burgundy shades. Pat τ claim: Modification of the method of representation protected by patent 175069, class 12 of arylaminoanthraquinones and their derivatives, consisting in that one halobenzene derivatives of the form Hal. • C ₆ H ₄ . X. C ₆ H ₄ - Hal.
or Hal.
Shark. _X 0 . Shark
Whale. (X = O ₁ S or NH; Y = any radical with two free valences on one atom, e.g. CO, NH) condensed with 2 mol. Aminoanthraquinones or their derivatives.