DE2338973A1 - NEW MONOAZO PIGMENTS AND METHODS FOR THEIR PRODUCTION - Google Patents

Description

The present invention relates to new, valuable monoazo pigments the general formula

ZCOIffi-i

pOCH ₃

H-R-CHC ONH-

; c = o

wherein R, X _x and X _{2 are} identical or different and represent a hydrogen atom, a chlorine or bromine atom, a methyl, ethyl, methoxy or ethoxy group, Z represents a methyl or ethyl group or a phenyl radical which is one or two May have chlorine or bromine atoms, methyl or methoxy groups as substituents and in which the group - HHCOZ is in meta or para position to the azo group.

The invention also relates to a method for production above-mentioned azo pigments, in which one diazotized aromatic amines of general formula

ZCOIiH

wor-in the group - NHUOZ in meta- or para-position to the amino group

'509810/1069

stands, with coupling components of the general formula

CH ₃ COCH ₂ CONH-

JC = O

in which R, X ₁ , X ₂ and Z have the meanings given above, couples.

Most of the amines used as diazo components are already known and / or can be produced by known methods, for example by nitriding and then reducing a correspondingly substituted acylaminobenzene of the formula

where X ₁ , X ₂ and Z have the meaning given above. As a diazo component !! can be used for example:

3-amino-acetanilide 4-chloro-3-amino-acetanilide 4i6-dichloro-3-amino-acetanilide 4-Bromo-3-amino-acetanilide 4,6-l) ibromo-3-amino-acetanilide 4-chloro-6-methyl-3-amino-acetanilide 4-bromo-6-methyl-3-amino-acetanilide 6-chloro-3-amino-acetanilide 6-methyl-3-amino-acetanilide 4-ethyl-3-amino-acetanilide 4 »ii-dimethoxy - ^ - ainino-acetanilide 4-Ethoiy-3-amino-acetanilide 3-Amino-propionanilide 4-chloro-3-aminopropionanilide 4-chloro-6-methyl-3-aminopropionanilide 4-methoxy-3-aminopropionanilide 3-benzoylamino-aniline 3- (2'-chloro-benzoylamino) aniline 3_ (4 "_Chlor-3'-ynethyl-benzoylamino) -aniline

509810 / 10G9

5- (2 ', 4'-dichloro-benzoylainino) -aniline 5- (2 ^r , 5 ^t -di ^ rom-benzoylamino) -aniline 2-chloro-5-benzoylamino-aniline 2-chloro-5- (4 '-chloro-benzoylaiaino) -aniline 2-chloro-5- (2', 5'-dichloro-benzoylamino) -aniline 2-chloro-5- (4'-methoxy-benzoylamino) -aniline 2,4-dichloro-5 -benzoylamino-aniJin 2 _f 4-Mchlor-5- (2 ', 4 * -dichlor-benzoy! amino) -aniline 2 _t 4-dichloro-5- (4 ^l -chloro-2 ^l -methyl-benzoylaiaino) -aniline 2,4-dichloro-5- (4'-bromo-benzoy! Amino) -aniline 2-chloro-4-methyl-5-benzoylamino-aniline 2-chloro-4-diethyl-5- (2 ^! -Chlor- benzoylamino) aniline 2-chloro-4-iaethyl-5- (3'-chloro-benzoylamino) -aniline 2-chloro-4-methyl-5- (2 ', 5'-dichloro-benzoylamino) -aniline 2-bromo -5-benzoylamino-aniline 2-bromo-5- (2 ·, 4'-dichloro-benzoylamino) -aniline 2-methyl-5-benzoylamino-aniline 2-methyl-5- (4'-chloro-benzoylamino) -aniline 2-methyl-5- (2, 5'-dichloro-benzoylamino) -aniline 4-methyl-5- (2 ', 4'-dichloro-benzoylamino) -aniline 4-methyl-5- (4'-chloro- 2'-methoxy-benzoylamino) -aniline 2-methoxy-5-benzoylamino-aiiiline 2-methoxy-5- (2'-chloro-benzoylamino) -anili n 2-Methoxy-5- {4'-chloro-3 ^l -niethyl-benzoylaiaino) -aniline 4-aminoacetanilide

2-chloro-4-amino-acetanilide 3-chloro-4-amino-acetanilide 2,5-Bichlor-4-aiaino-acetanilide 2,6-dichloro-4-amino-acetanilide 2-Bromo-4-amino-acetanilide, 2-chloro-5-methyl-4-amino-acetanilide 5-chloro-2-iaethyl-4-a-diino-acetanilide 2-methyl-4-amino-acetanilide 5-methyl-4-amino-acetanilide, 2-methoxy-4-amino-acetanilide 2-Hethoxy-5-methyl-4-amino-acetanilide 2,5-Dimethoxy-4-amino-acetanilide 2,5-dichloro-4-aminopropionanilide

50981 071069

^ -Benzoylamiuc-aniline.

4- {2 ', 5'-Mulilor-bensoy! Amino) -aniline 4- (4'-Broia-beiizoyla] Bino) -aiiiiin 2-chloro-4-beii55oylainino ~ 8nilirA 3-0hlor-4- (4 ^! - chlor-3 '-ethyl-tun2oyla: riino) -aniline 2,5-jDichlor ~ 4 ~ l> ei? .zoylaEin.G-aiiilIn 2,5-35ichlor ~ -4- (4 ^l -cl ¹ lor-2' -aiethozy-benaoylaiaino) -aiiilin 2-Chlsx * -5 " ^IQe ti ^{; i} yl-4 ~ {2 ' i 4'-dichloro-usnzoylaninoj-aniline 5-chloro-2-methyl-4-ben7-oylaiaino-aniline 5 -Chlor »2-ynethyl-4- (4 '-chlor-2 ^! -Mo thcxy-benzoylamino) -aniline 2,5-bimetlioxy-4- (4 ^l -chlcr-berizoylamino) -aniline

-4- (2 ³ _s ' 3 ", M-trichlorobenzoj'lamino) aniline

The compounds used as coupling components are for the most part known and can be prepared by known processes, for example by reacting a J-Äixio-benziiaidaaolone with diketene. As ge-r. suitable coupling components are mentioned?

5-acetoacetylainino-benziinidazolone 6-chloro-5-acetcacetylase: i2o ~ bensi23idazolon 7-chloro-5-acetoacetylamino-bensiIίiidazolon 6-Broia-5-acetoacetylair! Ino-ben2iLiidasoloa

6-Methyl-5-aeetoacetylaniino-bensiißiäa3olone 7-methyl-5-acetoacetylaIίlino-benEiraidazolon 7-Aethyl-5-acetoacetylaπίino-bpn! ^ IElidazolon 7-methoxy-5-acetoacetylaInino-benκimidazolon 7 ~ ethoxy ~ 5-acetoacetylaiaino-bensimidazolone

The coupling reaction takes place in a known manner, for example in an aqueous one Medium, optionally in the presence of non-ionogenic, anion-active or cationic dispersants and / or organic solvents. The coupling can also be carried out in organic solvents.

To achieve the optimal color strength and a particularly favorable one Crystal structure, it is often appropriate to the coupling mixture some Time to heat, for example to boil or to bring to temperatures above 100 ° under pressure, if necessary in the presence of organic solvents such as dichlorobenzene, or Diinethylfoi'raania or from resin soap. Bcson-

509810/1069

the pure and real colorations are obtained with pigments that are perfectly suited to the invention, if, after coupling, they are used as a moist press cake or as a dried powder, after treatment with organic solvents such as Pyridine, dimethylformamide, dimethyl sulfoxide, H-methy! Pyrrolidone »alcohols, Glycol, glycol monomethyl ether, glacial acetic acid, chlorobenzene, dicilorbensol or Nitrobenaol at boiling temperature or under pressure at elevated temperature

w irf t ^ —Oil ^ r ^ /
^ / h MaKTung the pigments with the addition of Mahlhilfsisiiteiii -

closes. In some cases, the Uefaerführung example of the type mentioned above is possible in a particularly favorable crystal structure by heating with water sum cooking or to higher temperatures under pressure, optionally with Zusats of dispersing agents and optionally with the addition% ^r on organic solvents. The pigments can also are coupled in the presence of carrier substances that are suitable for Parblaek production.

The new pigments are suitable for the production of printing inks, lacquer paints and emulsion paints, and for coloring rubber, plastics and natural or synthetic resins. The new pigments are also suitable for pigment printing on substrates, in particular sextile fiber materials or other sheet-like structures, such as paper, for example. The pigments can .vmgszwecke, s "B _f or esters in finely divided form for the dyeing of rayon viscose or cellulose ethers, polyamides, polyurethanes, polyglycol or polyacrylonitrile are used in the textile pulp or dyeing of paper for other Anweiic>.

The new pigments are easy to process in ate mentioned media. The dyeings have very good light, weather and migration fastness properties and are resistant to the action of heat and the action of chemicals, for example solvents.

The inventive products are distinguished by their excellent fastness properties Pigments in particular from the following;

- N = Ii-CHCONH-r ^ ~ VNH ~ \ _{c = 0}

509810/1069

= N-CHC ONH-

CH ₃

NHCOCH ₃

93

N = H-CHC ONH

⁰¹ NHCO

Example 1:

21.9 S 4fß-dichloro-1-araino-apetanilide are stirred with 100 ml of glacial acetic acid and JO ml of T & XM & SXiSäöaGX 31% hydrochloric acid for 2 hours at room temperature and then diazotized at 0-5 ° with 21 ml of 5 ml of sodium nitrite solution. You can stir for JO minutes, destroy the excess nitrite with Auiidosulfonsäure and clarify *

2414 g 5-A ^ce ^ ^oace 'fcylaraino-'benzimidazolon be in a Mischung- of 500 ml water, 2. ¹ ml of 53 J jSiger sodium hydroxide solution and 5 ml of a 10 ^ aqueous

r h

Solution of the reaction product from 1 pint of steayl alcohol and 20 mol of ethylene oxide solved. At 15-20 ° the coupling component is collapsed by 17 »5 ml of glacial acetic acid precipitated. The diazonium salt solution is then added at 20 ° slowly run in to the suspension of the coupling component. Of the The pH value is increased by the simultaneous addition of approx. 3 ^ 5 ral 5N sodium hydroxide solution held about 6.3. After the coupling has ended, the mixture is heated to 95 ° and held at 30 ° Minutes at this temperature. It is then filtered off, washed and dried.

42 g of the dry pigment powder are boiled IAIT 450 ^m l of dimethylformamide reflux for 1 hour. After cooling to 50 °, it is suctioned off, with

Water washed, dried and ground. The monoasopigant obtained from the formula 509810/1069

338973

IUICOCH ₃

shows during incorporation ie a varnish in one! ink in polyvinyl chloride, or in a Spinnm ~ se very pure _f orangegolbe FarbuBgen before excellent light and MigrationDechtheit *

Example 2:.

101 5 £ ί 4 ~ C.hlor-3-arjino-acetanilide werder. with 100 αΐ glacial acetic acid and 25 ml concentrated hydrochloric acid for 2 hours at room temperature and then sotized at 0-10 ° with 20.5 ΙΙ 5n ratri ^ mnitrite solution. You let stir for 50 minutes, destroyed the Kitritüberseiraß with Amidosulf on acid and clarifies. The Eiason ammonium salt solution is then gradually added to a suspension of 28.1 g of 7-chloro-5-acetylamino-benzimidazolone in 550 ml of pyridine. After the addition has ended, the mixture is stirred for a further 1 hour and then filtered off, washed with water and dried at 60 °. / j8 g of the dry pigment powder are refluxed with 5GC ml of glacial acetic acid for 1 hour. After cooling to 50 °, it is filtered off with suction, washed with water, dried and ground. The honoazo pigment of the formula obtained in this way

COCH ₃
π- I ₁ = H-CH-COHI- ^ V ' ^1ΓΗχ _{0 = ι0}

HHCOCH ₃ Cl;

results in incorporation in a printing ink, in polyvinyl chloride, in one Lacquer oier one layer> was very pure, greenish-yellow colorations of excellent color Lightfastness and immaculate migration fastness.

At ppicl J > \

19t9 C i ^> ~ Ch3or-5-ynethyl-4'-ainino-acetanilide are dissolved in 00 ml of hydrochloric acid

509810/1069.

stirred for about 1 hour. Then you dilute with ice water to about 25O ml and diazotized slowly at 0-5 ° with 20.5 nil 5N sodium nitrate solution. The mixture is stirred for 30 minutes and the excess nitrite is destroyed with sulfamic acid and clarifies.

2315 g of IJ-acetoacetylamino-benzimidazolone are suspended in 300 ml of water and dissolved by adding 75 ml of 2N sodium hydroxide solution. The clarified alkaline solution is added dropwise at the same time as the diazonium salt solution in the course of 2 hours at IO-I5 ⁰ to a mixture of 100 al 4N sodium acetate solution, 20 ml of glacial acetic acid and 10 ml of a 10% aqueous solution of the reaction product of 1 mol of stearyl alcohol and 20 Moles of ethylene oxide. After the coupling has ended, the pigment suspension is heated to 90 ° for 1 hour. The pigment is filtered off with suction while hot, washed salt-free with water, dried at 60 ° and the ground product is stirred in 300 ml of dimethylformamide. After heating to 60 ° for 10 minutes, the pigment is filtered off with suction, washed with methanol, dried and ground.
The monoazo pigment of the formula obtained in this way

9 ₃
CH ₃ C ONH - // \\ - N = N-CH-C ONH- iS ^ V NHv

NH

When incorporated into an alkyd-melamine resin clear lacquer and subsequent application of the pigmented lacquer on test cards over a black and white background, after 30 minutes of stoving at I40 ⁰ results in bright orange colorations of high transparency, perfect fastness to overcoating and excellent lightfastness.

Example 4:

33, Og 2-chloro-5-methyl-4- (2 ^l , 4'-dichlorobenzoylamino) aniline are introduced into 100 ml of 5N hydrochloric acid at 80 ° with stirring. After 10 minutes, the mixture is cooled to room temperature and the suspension is then left to stir overnight. The next morning, it is diluted to about 250 ml with ice water and diazotized at 5 ° with 20.5 ml of 5N sodium nitrite solution according to consumption. The mixture is left to stir for 30 minutes and the excess nitrite is destroyed with it

509810/1069

Amidosulfenic acid and clarifies.

27j0 g of 7-chloro-5-acetoacetylamino-benziH ¹ idazolone are suspended in 300 ml of water and dissolved by adding 15 ml of 33% sodium hydroxide solution. The clarified alkaline solution is added dropwise at the same time as the diazonium salt solution at IO-I5 ⁰ with stirring over the course of one hour to a mixture of 200 ml of water, 25 g of orthophosphoric acid, 30 ml of 33% sodium hydroxide solution and 10 ml of a 10% solution of the Reaction product of 1 mole of stearyl alcohol and 20 moles of ethylene oxide. After the coupling has ended, the pigment suspension is heated to 90 ° -95 ° for one hour. The pigment is filtered off with suction while hot, washed salt-free with water, dried at 60 ° and the ground orange-brown product is stirred in 500-liter glacial acetic acid. The suspension is heated to 100 ° with stirring, the color gradually changing to yellow. After three hours of heating, the yellow pigment is filtered off with suction, washed acid-free with methanol, dried and ground. The pigment of the formula obtained

C = O

When incorporated into polyvinyl chloride, a varnish, a printing ink or a spinning mass, it produces pure ^x yellow colorations with perfect migration and excellent lightfastness.

If, in the above example, ^{the equivalent amount of 5-acetoacetylamino-benzimidazolone is used instead of% r} on benzimidazolone, a reddish-yellow pigment is obtained which, after being incorporated in a printing ink, a varnish, in polyvinyl chloride or in a spinning dope, has reddish-yellow colorations with a similar gives good fastness properties.

The following table contains a number of other process equipment that can be used Components as well as the color tones of the graphic prints of the difazo pigments produced from them in substance:

INSPECTED 509810/1069

Diazo component

- yo -

-10-

ICuppIong & component

3-Amino-acetanilide 5-Acetoacetylamino-benzimidazolone yellow

4-chloro-3-aminoacetanilide

7-chloro-5-acetoacetylamino- greenish yellow

benzimidazolone

5-acetoacetylamino-benzimidazolone greenish yellow

7-Bromo-5-acetoacetylamino-benzimide greenish yellow

azolone

amino-acetanilide ⁿ

4 »6-dichloro-3-amino-6-methyl-5-acetoacetylamino-benzene - reddish yellow acetanilide imidazoion

ⁿ 7-Meth.o3cy-5-acetoacetyla.mino- reddish yellow

benzimidazolone

J- S-Acetoacetylamino-benziinidazolone reddish yellow

6-chloro-5-acetoacetylamino-benz - reddish yellow

imidazoion

5-acetoacetylamino-benzimidazolone reddish yellow

6-chloro-5-acetoacetylamino-benz -.- · reddish yellow

imidazoion

S-acetoacetylamino-benzimidazolone yellow

y-chloro ^ -acetoacetylamino-benz. - greenish yellow

imidazoion

5-acetoacetylamino-benzimidazolone reddish yellow

6-bromo-5-acetoacetylamino-benz. - reddish yellow

imidazoion

amino-acetanilide

6-methyl-3-aminoacetanilide

4 »6-dimethoxy-3-amino-acetanilide

4,6-dichloro-3-amino-7-Cb.lor-5-acetoacetylamino-benz - yellow propionanilide imidazoion

ⁿ 7-Methyl-5-acetoacetylamino-benz - reddish yellow

imidazoion

3-Benzoylamino-aniline 7-chloro-5-acetoacetylamino-benz - greenish yellow

imidazoion

"6-Bromo-5-acetoacetylamino-benz - greenish yellow

imidazoion

3- (2, 4'-dichlorobene-7-ethoxy-5-acetoacetylamino-benz - reddish yellow zoyl-amino) -aniline imidazoion

" 6-Kethyl-5-acetoacotylamino-benz - reddish yellow

imidazoion

2-chloro-5- (2'-chloro-5-acetoacetylaminobenzimidazolone yellow benzoyl-amino) -aniline

"6-chloro-5-acetoacetylamino-benzi-" yellow

iiidazolone

2-chloro-5- (2; 4'-dichloro-5-acetoacetylamino-benzimidazolone reddish

benzoylamino) aniline

yellow

509810/1069

7-chloro-5-acetoacetylamino-benz-yellow

imidazoion

Diazo component

Coupling component

hue

2,4-dichloro-5- (4 '- 5-acetoacetylamino-benzimidazolone chloro-3 · methylbenzoylamino) aniline

"7-Bromo-5-acetoacetylamino-benz -

imidazolone

2 ₁ 4-dichloro-5- (4'- 7-chloro-5-acetoacetylamino-benz-

br ombenzoy lamino) aniline

2-bromo-5-benzoylamino-aniline

imidazolone

7-Methy1-5-ac et oac etylamino-benz -

imidazolone

reddish yellow

yellow yellow

yellow

5-aeetoacetylamino-benzimidazolone yellow

7-chloro-5-acetoacetylamino-benz -

imidazolone

2-chloro-4-methyl-5-S-acetoacetylamino-benzimidazolone

(2 ', 5'-dichlorobenzoyl-

amino) aniline

greenish yellow

reddish yellow

7-methoxy-5-acetoacetylamino-benz - reddish yellow

imidazolone

2-methyl-5- (2 ', 4 * - 5-A ^ce toaeetylamino-benzimidazolone

dichloro-benzoylamino) -aniline

¹¹ 6-methyl-5- & eetoacetylamino-benz -

imidazolone

4-methyl-5- (4Lchlor-5-acetoacetylaiaino-benzimidazolone

2-methoxybenzoylaminoaniline

"ö-chloro-S-acetoacetylamino-benz .-

imidazolone

2-methoxy-5- (4'-chloro-5 - ^ - cetoacetylamino-benzimidazolone 3'-methyl-benzoy1-amino) aniline

ⁿ ■ 7-chloro-5-acetoacetylamino-benz -

imidazolone

4-aaino-acetanilide

2-chloro-4-aminoacetanilide

5-acetoacetylamino-benzimidazolone

7-chloro-5-acetoacetylamino-benz -

imidazolone

5-acetoacetylamino-benzimidazolone

7-methyl-5-acetoaeetylamino-benz -

imidazolone

yellow

reddish yellow reddish yellow

yellow reddish yellow

greenish yellow

reddish yellow yellow

yellow yellow

509810/1069

Diazo component

Coupling component

hue

3-chloro-4-aminoacetanilide

S-acetoacetylamino-benzimidazolone

ö-chlorine ^ -acetoacetylainino-benz-

imidazolone

2, S-Tue
acetanilide

2-chloro-5-methyl-4-amino-acetanilide

imidazolone S-acetoacetylamino-benzimidazolone

reddish yellow greenish yellow reddish yellow yellow

T-chloro-S-acetylamino-benzimidazolone yellow 5-acetoacetylamino-benzimidazolone reddish yellow

T-chloro-J-acetoacetylamino-benz-

imidazolone

¹¹ 'T-methyl-S-acetoacetylamino-benz-

imidazolone

2-methoxy-5-methyl-S-acetoacetylamino-benzimidazolone 4-amino-acetanilide

"o-Methyl-S-acetoacetylamino-benz-

imidazolone

2,5-dimethoxy-4-amino-acetanilide

S-acetoacetylamino-benzimidazolone

7-BΓom-5-acetoacetylamino-benz-

imidazolone

greenish yellow

yellow reddish yellow reddish yellow orange reddish yellow

2,5-dichloro-4-amino-5-acetoacetylamino-benzimidazolone yellow propionanilide

"o-chloro - ^ - acetoacetylamino-benzimide-yellow

azolone

5-acetoacetylamino-benzimidazolone

4-benzoylaminoaniline

reddish yellow

ö-bromo-S-acetoacetylamino-benzimide-

azolone

4- (4'-chlorobenzoyl-S-acetoacetylamino-benzimidazoloii amino) aniline

yellow yellow

7-chloro-5-acetoacetylaInino-benzilnide yellow

azolone

4- (2 ', 4'-DiChIOr-

benzoyl-amino) -aniline

5-chloro-4- (4'-benzoylamino) aniline

5-acetoacetylamino-benzimidazolone

y-ethoxy-S-acetoacetylamino-benz-

imidazolone

^ -Acetoacetylamino-benzimidazolone

yellow

reddish yellow yellow

T-chloro ^ -aeetoacetylamino-benzimide-yellow

azolone

509810/1069

Diaz o component coupling component

hue

3-chloro-4- (4'-chlorobenzoylamino) aniline

3-chloro-4- (2'4'-dichlopbenzoylamino; -aniline

3-chloro-4- (4'-chloro-3 '-methyl-benzoy! Amino) -aniline

2,5-dichloro-4- (4'-chlou-2 ' -methoxy-benzoylamino ^ aniline

3-Bromo-4- (4-chlorobenzoylamino) aniline

2-Chloro-5-inethyl-4 <4 ^f chloro benz oylamino) aniline

2-chloro-5-methyl-4- (2 ', 4 ^! -Dichlorobenzoylamino) aniline

5-chloro-2-methyl-4- (4'-chlorobenzoylamino) aniline

5-chloro-2-methyl-4- (4'-bromobenz oylamino) aniline

2-methoxy-4- (4'-bromob enz oylamino) eni 1 in 6-methyl-5-acetoacetylaminobenzimidazolone

5-acetoacetylamino-benzimide

azolone

ö-bromo ^ -acetoacetylaminobenzimidazolone

5-acetoacetylamino-benzimide

azolone

Y-methoxy-S-acetoacetylaminobenzimidazolone

5-acetoacetylamino-benzimide

azolone

7-chloro-5-aeetoaeetylaminobenzimidazolone

5-acetoacetylamino-benzimide

azolone

o-methyl-S-acetoacetylaminobenzimidazolone

5-acetoacetylaniino-benzimide

azolone

7-BroIn-5-acetoacetylamino-benz-

imidazoloxx

T-chloro-S-acetoacetylaminobenzimidazolone

o-methyl-S-acetoacetylaminobenzimidazolone

5-acetoacetylamino-benzimide

azolone

benzimidazolone

5-acetoacetylamino-benzimide

azolone

ö-chloro-S-acetoacetylamino-bena-

imidazolone

5-acetoacetylamino-benzimide

azolone

Y-chloro-S-acetoacetylamino-bena-

imidazolone

yellow yellow yellow yellow

reddish yellow yellow

yellow yellow yellow reddish yellow

yellow yellow

yellow yellow

yellow yellow

yellow

reddish yellow yellow

509810/1069

Diazo component coupling component

hue

4-ethyl-3-amino-acetanilide

4-ethoxy-3-amino-acetanilide

2,5-diethoxy-4-aniinoacetanilide

5-acetoacetylamino-benzimidazolone

5-acetoacetylamino-benzimidazolone

5-acetoacetylamino-benzimidazolone

reddish yellow

orange

/ 15

509810/1069

Claims (1)

HOE 73 / F Fat exhausted 1.) IToiioaaopigmente of the general formula _JN = N-CH-CONH— R. wherein Ii, X ₁ and X _{2 are} identical or different and represent a hydrogen atom, a chlorine or bromine atom, a methyl, ethyl, methoxy or ethoxy group, Z is a methyl or ethyl group or a phenyl radical which is a or can have two chlorine or bromine atoms, methyl or methoxy groups as substituents and v; orin the group -NHCO2 is in the meta or para position to the azo group. 2.) The monoazo pigment of the formula - ', Cl 5 ·) The monoaso pigment of the formula Cl 90CH ₃ B- ^ \ nr / N = N-CHC0iiH-r < ^:? "^ _r ^/ ^ \ _Λ U P ^{= 0} 4.) Bas monoazo pigment of the formula 9OCH ₃ 1Ϊ-Ν -CHC ONH — i ^ V ^ \ ¹ "^ C = O if 509810/1069 5 ·) The monoazo pigment of the formula COCH ₃
= N-CH-CONH egg NHCO— // \ V_C1 6.) Process for the production of monoazo pigments according to claim 1, characterized in that one diazotized aromatic amines of the general formula ZCONH in which the group -NHCOZ is in the meta- or para-position to the amino group, with coupling components of the general formula CH ₃ COCH ₂ CONH- wherein R, X ₁ , X ₂ and Z tie have the meanings given above, couples. 7) Process for dyeing or printing lacquers, lacquer images, solutions and products made from acetyl cellulose, natural resins or synthetic resins, polystyrene, polyolefins, polyacrylic compounds, polyvinyl compounds, polyesters, rubber, casein or silicone resins, as well as paper or textile fibers from GfcilluBlose, cellulose ethers, Celluloseesv-cv? n _t polyamides or polyurethanes, characterized in that Honoazcpigmente used claim. 1 509810/1069