DE2317532C2 - Monoazoplgment, process for its manufacture and its use - Google Patents

Description

2. Process for the production of the monoazo · pigment according to claim 1 by coupling diazotized ρ - nitroaniline to 5 - acetoacetylaminobenzimidazolone and subsequent thermal treatment at temperatures of 80 to 150 ° C.

3. Use of the pigment according to claim 1 for coloring or printing plastics, natural and synthetic resins, rubber, paper, viscose silk, cellulose esters or alder, Polyolefins, polyurethanes, polyacrylonitrile or polyglycol terephthalates and for production of printing inks, lacquer paints or dispersion paints.

The invention relates to a monoazo pigment / formula

COCH ₃
N = N-CH-CONH-

NH

CO

NO,

also a process for its preparation, in which p-nitroaniline is diazotized in a known manner. on 5-Acctoacetylamino-benzimidazolon couples and the crude pigment obtained by thermal aftertreatment brings into the desired pigment form, lowie the use of the monoazo pigment.

The preparation of the pigment can be carried out in such a way that the solution of the di-itzo compound with the coupling component present in the form of a fine dispersion in a weakly acidic medium combined or that the alkaline solution of the coupling component to the submitted, by adding sodium acetate lien pH-wide 5 to 6 solution of the diazo component lets flow. Another possibility for implementing the coupling is that The solutions of the diazo and coupling components together to form a sodium acetate-acetic acid buffer mixture lets flow.

In all of these procedures, the presence of cationic, anionic or nonionic Surface-active compounds may be beneficial. To produce the optimal pigment form with regard to Grain softness, color strength, hiding power and processability in paints and plastics must the pigment according to the invention can be subjected to a thermal aftertreatment. Here can the aqueous pigment suspension in water at temperatures from 80 to 150 ° C, d. H. possibly under Pressure or preferably in the presence of organic solvents such as alcohols, lower carboxylic acids, Carboxylic acid alkyl esters !!. Aromatics, chlorinated aromatics, aprotic solvents such as Dimethylformamide. P ^ ethylsulfox.d Pyr, d, n at

Temperatures between 80 and 180 C can be treated. The mixed organic Solvent also in pure 1-form or in mixtures with one another on the dried untreated Act pigment.

ίο The azo pigment according to the invention is an orange one Powder that is completely insoluble in common solvents. ,,. ,,., ..,, ■ "

It is characterized by high color strength, brilliant hue, excellent opacity as well as particularly

good light and weather fastness. It applies here next comparable azo pigments, which are produced with the same coupling component, but as a diazo component üem p-nitroaniline next vf - Connections included. So that's inventiveness

Pigment corresponding pigments with 3-Niiranilin. "M-Dinitraniline. 4-Chloroaniline, 4-Methylaniline or 4-methoxyaniline as a diazo component in light and weather resistance superior. The azo pigments described in German patent specification 1 227 5i! 5

with 2-chloroaniline, 2-methylaniline and 2-metho \\ - Aniline as a diazo component is the pigment according to the invention in light and weather law, the pigment With 2-nitroaniline as a diazo component, it is superior in terms of coverage and brilliance of the color shade.

The new azo pigment can be used for a wide variety of pigment applications, for example for the production of printing inks, for the preparation of lacquer paints and emulsion paints or for coloring rubber. Plastics.

natural and synthetic resins. The pigment is also suitable for pigment printing on a Substrate, in particular a textile fiber, as well as on other sheet-like structures, such as for example Paper. The pigment can also be used for other

applications, e.g. B. for dyeing rayon rayon or cellulose ethers or esters, of Polyolefins. Polyamides, polyurethanes. Pohgl> col- • erephthalates or polyacrylonitrile can be used in the spinning pulp or for dyeing paper.

Example I.

i3.8 g (0.1 mol) p-nitroaniline are dissolved in XO ml Stirring 5N hydrochloric acid. It is cooled to 0 to 5 ° C. with ice and diazotized by adding 20 ml of 5N sodium nitrite runs under the surface. Then kieselguhr is added, the mixture is stirred for 10 minutes and then filtered.

70 g of 35% strength 5-acetoacetylaminobenzimidazolone were dissolved in 2 (X) ml of water and 25 ml of 33% strength sodium hydroxide solution Dissolved at 22 C and then clarified with animal charcoal.

The mixture is placed in 5 (X) ml of water. 25 g

Phosphoric acid, 30 ml of 33% sodium hydroxide solution and

10 ml of a 10% aqueous solution of a Stearylaikoholoxäthylates (with 20 ethylene oxide) as a buffer.

At 22 ° C, the diazo solution and the solution of the coupling component flow simultaneously to form the buffer solution. It is heated to 95 ° C., stirred for 1 hour at this temperature, then suction filtered and washed.
150 g of moist press cake are mixed with 140 g of

butanol and 200 ml of water and kept in a closed vessel 1V for ₂ to 1 hour at 125 ° C. After the isobutanol has been driven off with steam and filtered off, it is obtained after drying

an orange-red pigment with excellent light- and weather fastness, high coverage and good Flow and high gloss in the stoving varnish.

B e i s ρ i e I 2

27.6 g (0.2 mol) of p-nitroaniline are used in the im Example I indicated manner diazotized. Diazo solution and azo components flow simultaneously into a Na acetate / glacial acetic acid buffer of the following composition: 1000 ml of water, 82 g of sodium acetate, 20 ml of glacial acetic acid "° and 10 ml of a 10% aqueous solution of a Stearylalkoholoxäthylates with 20 ethylene oxide. It is heated to 95 ° C and kept at this temperature for 1 hour, then suction filtered and washed with water washed.

The moist press cake, which contains about 25% pigment, is made according to the information in Example 1 finished with isobutanol. The mixture is subjected to steam distillation and is obtained after drying, an orange-red pigment with the properties described in Example 1.

Example 3

11.8 ü p-nitroaniline are diazotized and with a Solution of 24 g S-acetoacetylaminobenzimidazolone * 5

15 in 200 ml of water and 24 ml of 33% sodium hydroxide solution by placing both solutions at about 20 ° C. in a buffer of 500 ml of water, 40 g of sodium acetate, 10 ml of glacial acetic acid and 10 ml of a 10% aqueous solution of an emulsifier, which was obtained from stearyl alcohol by reaction with 20 mol of ethylene oxide is allowed to flow in. The mixture is stirred for 1 hour, heated to 95 ° C., kept at this temperature for 1 hour and filtered off with suction.

125 g of moist press cake were heated with the addition of 200 ml of water under pressure for ¹ _{l for 2} to 1 hour at 125 ° C., filtered off with suction and washed with water.

After drying, an orange-red pigment with very good fastness properties is obtained.

Example 4

125 g of press cake (about 20%) are stirred with 96% by weight of o-dichlorobenzene and 100 ml of water and added to 125 C in a closed vessel heated for 1 hour. The pigment emulsion is then blown in freed of steam from o-dichlorobenzene. Obtained after filtering off, washing and drying an orange-red pigment of the same nature as described in Example 1 is used.

Claims (1)

Patent claims:
I. Monoazo pigment of the formula
CH ₃ CO N = N-CH-CONH NO,