DE3318230A1 - Disazo pigment dye - Google Patents

Abstract

The compound of the formula <IMAGE> in particular the beta -crystal modification, is outstandingly suitable as a pigment dye. The invention also relates to the preparation of the compound by diazotisation and coupling and to the preparation of the beta -modification by heating the alpha -crystal form in dimethylformamide.

Description

DISAZO PIGTENT COLOR

It has been found that the compound of the formula I In particular, the β-crystal form of this compound is excellently suited as a pigment dye, especially for coloring paints and varnishes of all kinds, for pigment printing and for mass coloring viscose.

The α-crystal modification of the compound of formula I, marked by two lines in the X-ray diffraction diagram (Cu-Kal radiation) at lattice spacings 8.75 A (weak, diffuse line) and 3.29 (medium, diffuse line) are obtained by coupling 2 nmoles of diazotized 2,4-dichloroaniline with n mols of 2-methoxy-1,4-bis (acetoacetylamino) benzene.

This reaction is carried out analogously to known processes.

The h-modification, which is more valuable in terms of coloration, characterized by the following lines in the X-ray diffraction diagram (Cu-Kα1 radiation) at gitter distances Line d (Å) I (intensity 1 8.5 v w d 2 7.5 v w d 3 3.88 w d 4 3.7 v w d 5 3.5 v w d 6 3.28 m 7 3.16 v w d (vwd = very weak, diffuse, wd = weak, diffuse, m = medium strength) is obtained by cooking the more than half the time a-modification in an organic solvent, e.g. ethanol, a glycol ether, Acetic acid, benzene, nitrobenzene, toluene, formamide or a dialkylformamide, in particular in dimethylformamide. In general, the compound is boiled for about 1 hour on the reflux condenser, filtered at a temperature above 10OGOC, preferably around 1200C, washes the pigment first with dimethylformamide and then with water.

The crystal modification obtained in this way is after this treatment already in a form suitable for pigment purposes, conditioning is not more needed. The α-crystal modification is generally less true than the α-modification.

Unless otherwise stated, in the examples the meanings are parts Parts by weight and the percentages are percentages by weight. The temperatures are in degrees Celsius specified.

B e i s p i e 1 1 (production of the a-todification) A mixture from 32.4 grams of 2,4-dichloroaniline, 185 ml of water and 85 ml of 30 percent hydrochloric acid is heated to 90 ° and (about 30 minutes) stirred at this temperature until a clear solution is obtained. It is cooled to room temperature, with the hydrochloride precipitates out as a gray precipitate. The mixture is stirred for about 12 hours, 60 grams of ice are added and, In the course of 5 minutes, 52 ml of 4N sodium nitrite solution below level too, with the Temperature is kept at O-D °. The precipitate slowly dissolves with stirring on, it is stirred for 1 hour while cooling to 0-5 ", always an excess must be detectable on HNO2.

This excess is finally mixed with about 5 ml of 14-amidosulfonic acid destroyed. After adding 2 grams of filter earth (Hyflo-Supercel), it is clarified.

30.4 grams of 1> 4-bis (acetoacetylamino) -2-methoxyphenylene will be dissolved in 250 ml of water and 70 ml of approx. 30 percent sodium hydroxide solution, with 2 Grams of filter earth (Hyflo-Supercel) added, filtered clear, to a solution of 250 ml of water, 45 ml of glacial acetic acid and 6 ml of a commercially available wetting agent and added cooled to 0-5 °. In this solution is now also in the course of 6 to 7 hours to 0-5 ° cooled solution of the diazonium salt was added dropwise with stirring and the resulting The mixture was stirred for a further 12 hours without further cooling. The failed pigment is filtered off, washed with 3 liters of hot water (70 ") and at approx. 70" in Vacuum dried and falls as a yellow powder.

B e i s p i e 1 2 (production of the?> Modification) 65 parts of the Pigments obtained according to Example 1 are distributed in 500 parts of dimethylformamide and refluxed for 1 hour.

It is filtered after cooling to 1200, washed first with a little dimethylformamide, then with water and dry the pigment under vacuum. For further use the pigment is ground in a pin mill.

In 1/9 standard depth, colored as a varnish, are the colorimetric Values: Chroma (c) = 53.0 Hue (H) 59.3.

Example 3 4 parts of the pigment according to Example 2 are combined with 96 parts a mixture of 50 parts of a 60 percent solution of coconut aldehyde melamine resin with ~ 32 »fat content in xylene, 30 parts of a 50 percent tlelamine resin solution in Butanoyl, 10 parts of xylene and 10 parts of ethylene glycol monoethyl ether intimate The resulting dispersion is sprayed onto aluminum sheet, 30 minutes left to air dry and then 30 min.

baked in at 1200. A yellow film with a very good result is obtained in this way Resistance to light and weather.

Claims (1)

DISAZO - PIGMENT DYE P atent claims 1. The compound of the formula I 2. The 5-modification of the compound of formula I according to claim 1, characterized by the following lines in the X-ray diffraction diagram (Cu-Kα1 radiation) at lattice spacings line d (Å) I (intensity) 1 8.5 vwd 2 7 , 5 vwd 3 3.88 wd 4 3.7 vwd 5 3.5 vwd 6 3.28 m 7 3.16 vwd (vwd = very weak and diffuse, wd = weak and diffuse, m = medium) 3. Procedure for Preparation of the compound of formula 1 according to claim 1, characterized in that diazotized 2,4-dichloroaniline is coupled with 2-methoxy-1,4-bis (aceto-acetylamino) benzene. 4. Process for the preparation of the ß-modification of the compound of Formula I according to claim 2, characterized in that one according to claim 3 cooked compound in dimethylformamide for more than half an hour. 5. Use of the compound of the formula I, in particular the ß-modification, according to claim 2, as a pigment dye, for coloring paints and varnishes of all kinds, for pigment printing and for dyeing viscose. 6. Those colored with the pigment of the formula I according to claim 1 Materials.