DE2338973C3 - Monoazo pigments, process for their production and their use - Google Patents

Description

2. The monoii / opigment of the formula Cl

COCH,
// V _N; , _N _ _C |, -CONH ^ / VNH-

ΙΓ ^[

c = o

NHCOCH,

3. The monoazo pigment of the formula

9 COCH.,

(^ S) -N = NC-H CONH- / Y ^NHv ^ / k A Nl-K

1 I.

NHCOCH, Cl

4. The monoazo pigment of the formula

COCH,

C = O

35

40

45

N-NCIICONH

ι iT ^CM - <
Ci-L /

NHCOCH,

c-o

NH '

NHx

C = O

5. The monoazo pigment of the formula
COCH ₁

\ / NH \

C = O

NH

N = N-CH-CONH

-CH,

^C1 VL

NHCO- / V Cl

6. Process for the production of monoazo pigments according to claim I. characterized in that that one diazotized aromatic amines of the general formula

X,

ZCONH-Il

wherein the group —NHCOZ is in the meta or para position to the amino group, with coupling components of the general formula

CH ₁ COCH ₂ CONH

NH

C = O

55 wherein R, X ₁ , X ₂ and Z have the meaning given in claim I, couples.

7. Process for coloring or printing lacquers, lacquer images, solutions and products Acetyl cellulose, natural or synthetic resins, polystyrene, polyolefins. Polyacrylic compounds, Polyvinyl compounds, polyesters, rubber, casein or silicone resins, as well as paper or textile fibers made from cellulose, cellulose ethers, cellulose esters, polyamides or polyurethanes, characterized in that monoazo pigments according to Claim I are used.

The present invention relates to valuable monoa / opigments of the general formula

X,

ZCONH—

COCH, Y-N- = N-CHCONH γ NH

C = O

X ₂ R

in R. X ₁ and X _{2 are} identical or different and represent a hydrogen atom, a chlorine atom or a bio atom.

Methyl- · ethyl-. Methoxy or ethoxy group and Z is the methyl or ethyl group or a phenyl group, the one or two chlorine or bromine atoms. Have methyl or methoxy groups as substituents can., and in which the group - NHCOZ is in the meta or para position to the azo group.

Compared to such next comparable components from DT-OS 18 08 017, which also has an acylamino group and an additional methyl group in the benzimidazolyl ring, the pigments according to the invention are distinguished by better resistance to bleeding out.

The invention also relates to a process for the production of the abovementioned azo pigments. at which one diazotized aromatic amines dei general formula

^x v.

wherein the group NHCOZ in meta- or para-Stcllimg to the amino group, with coupling components of the general formula

CH ₁ COCH ₁ CONIi

. NU

: [C-O

'NII

wherein R, X ₁ . X _: and Z have the meaning given above, couples.

The diazo component !! are used amines for the most part already known and or can be produced by known methods, for example by Nitriding and then reducing an appropriately substituted acylaminobenzene of the general formula

X,

NHCO /.

where Χ ,. Xi and Z have the meaning given above own. As a diazo component !! can be used for example:

3-amino-aeetanilide.

4-chloro-3-amino-acctanilide.

4.6-dichloro-3-anlino-acetanilide.

4-Broni-3-amino-acctanilide.

4,6-dibromo-3-amino-acelanilld, 4-chloro-6-methyl-3-ate: iino-acetanilide.

4-bromo- (S-methyl-3-amine-aeetanilide.

(vChlor-.Vamino-acelanilid.

6-meth \ l-3-amino-acetaniid.

4-ethyl-3-amino-acctanilide.

4. (S-Dimethyl-3-amino-acet aiii lid.

4-ethoxy-3-aiiiino-acetanilide, 3-amino-propionaiilide.

4-chloro-3-amino-propionaniid.

4-chloro-6-meth \ l-3-aniino-piopionanilide.

4-Methoxv-3-amino-pI '^ lplonanilide.

3-benzoylaniino aniline.

3- (2'-chloro-benzoylamino) aniline.

3- (4'-chloro-3'-methyl-benzoylamino! -Aniline.

45

50

55

60

65 3- (2 ', 4'-dichloro-benzoylamino) -aniline, 3- (2', 5'-dibromo-benzoylamino) -uniline.

2-chloro-5-benzoylamino-aniline, 2-chloro-5- (4-chloro-benzoyiamino (-aniline, 2-chloro-5- (2 ', 5'-dichloro-benzoylamino) -aniline.

2-chloro-5- (4'-methoxy-benzoylamino) -aniline, 2.4-dichloro-5-benzoylamino-aniline, 2,4-dichlo! -5- (2 ', 4'-dichloro-benzoylamino) -

aniline,
2,4-dichloro-5- (4'-chloro-2'-methyl-benzoylamino) -aniline,

2,4-dichloro-5- (4'-bromo-benzoylamino) aniline. 2-ChIOr ^ mCtIIyI-S-benzoylamino-aniline. 2-chloro-4-methyl-5- (2'-chloro-benzoylamino) -

aniline,
2-chloro-4-met!; Yl-5- (3'-chloro-benzoylamino) -

aniline,
2-chloro-4-me (hyJ-5- (2'.5'-dichloro-benzoy) -amino) -aniline,

2-bromo-5-benzoylamino-aniline. 2-brorn-5- (2 ', 4'-dichloro-benzoylamino) -aniline. 2-methyl-5-benzoylamino-aniline, 2-methyl-5- (4'-chlorobenzoyiamino) aniline. 2-methyl-5- (2'.5'-dichloro-benzoylami, io) -aniline. 4-methyl-5- (2'.4'-dichloro-benzoylamino) aniline. 4-methyl-5- (4'-chloro-2'-methoxy-benzoylamino) -aniline,

2-melhoxy-5-benzoylamino-aniline, 2-methoxy-5- (2'-chloro-benzoylamino) -aniline. 2-methoxy-5- (4'-chloro-3'-methyl-benzo \ l-

amino) -aniline,
4-aminoacetanilide,
2-chloro-4-amino-acetanilide. i-chloro- ^ amino-acetanilide. 2,5-dichloro-4-amino-acetanilide, 2,6-dichloro-4-amino-acctanilide. 2-Bi om-4-amino-acetanilide. 2-chloro-5-methyl-4-amino-acetanilide. 5-Cl ^ lor-2-methyl-4-amino-acetanilide. 2-meth> l-4-amino-acetanilide. S-McthyM-amino-acctanilide. 2-methoxy-4-amino-acelanilide, 2-methoxy-5-methyl-4-amino-acetanilide. 2.5-dimethoxy-4-amino-acctanilide, 2.5-dichloro-4-amino-propionanilide, 4-benzoylamino-aniline.
4- (2 ', 5'-dichloro-benzoylamino) -aniline. 4- (4'-Bromo-benzoylamino) aniline. 2-chloro-4-benzoy! Amino-aniline. 3-chloro-4- (4'-chloro-3'-methyl-benzoylamino) -aniline,

2.5-dichloro-4-benzoylaI nino-aniline. 2.5-dichloro-4- (4'-chloro-2'-methoxy-benzoyl-

amino) -aniline,
2-chloro-5-methyl-4- (2 ', 4'-dichloro-benzoylamino) -aniline.

5-chloro-2-methyl-4-benzoylamillo-aniline. 5-chloro-2-methyl-4- (4'-chloro-2'-methoxybenzoylamino) -a niline.
2.?-Dimethoxy-4-(4'-chlor-benzoylamino|-

aniline.
2-ChIOr-S-HiCt h \ l-4- (2'.3'.4'-lriehlorben / oylamino) -aniline.

The Vi hindrances used as coupling components are largely known and can na known processes are produced, bcbeispielsw ei by reaction of an S-amino-benzimidazolone η

Diketones. Suitable coupling components are:

S-acetoaeetylamino-benzimidazolone,

ö-chloro-S-acetoacetylaminobenzimidazolone.

T-chloro-S-acetoacetylamino-benzimidazolone,

o-bromo-S-acetoacetylamino-benzimidazolone,

T-bromo-S-acetoacetylamino-benzimidazoion,

o-methyl-S-acetoacetylamino-benzimidazolone.

T-methyl-S-acetoacetylamino-benzimidazolone.

T-ethyl-S-acetoacetylamino-benzimidazolone.

T-methoxy-S-acetoacetylamino-benzimidazolone, T-ethoxy-S-acetoacetylamino-benzimidazolone.

The coupling reaction takes place in a known manner, for example in an aqueous medium, if appropriate in the presence of nonionic, anionic or cationic dispersants and / or organic solvents. The coupling can also be carried out in organic solvents.

It is often used to achieve optimal color strength and a particularly favorable crystal structure expedient to heat the coupling mixture for some time, for example to boil or under Bringing pressure to temperatures above 100 ° C., if appropriate in the presence of organic solvents such as dichlorobenzene or dimethylformamide or from resin soap. Particularly pure and real colors are obtained with the pigments according to the invention if they are obtained as a moist press cake after coupling or as a dried powder after treatment with organic solvents such as pyridine. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone. Alcohols, glycol, glycol monomethyl ether, Glacial acetic acid, chlorobenzene. Dichlorobenzene or nitrobenzene at boiling temperature or under pressure subjected at elevated temperature or followed by grinding of the pigments with the addition of grinding aids. In some cases, the transformation into a particularly favorable crystal structure also succeeds Heating with water for boiling or at higher temperatures under pressure, if necessary with addition of dispersants and optionally with the addition of organic solvents, for example of the type mentioned above. The pigments can also be used in the presence of carrier substances, which are suitable for the production of white lacquer are coupled pasture.

The new pigments are suitable for the production of printing inks, lacquer paints and emulsion paints, for coloring rubber, plastics and natural or synthetic resins. The new Pigments are also suitable for pigment printing on substrates, especially textile fiber materials or other sheet-like structures, such as Paper. The pigments can also be used for other purposes, e.g. B. in feinverteiller form for Dyeing of rayon from rayon or cellulose ethers or esters, polyamides, polyurethanes. Polyglycol terephthalates odur polyacrylonitrile can be used in spinning pulp or for dyeing paper.

The new pigments can be easily processed in the media mentioned. The colorations are very wise good light, weather and migration fastness and are against the effects of heat and the influence of Chemicals e.g. B. solvents, resistant.

The pigments according to the invention are distinguished in particular by their excellent fastness properties the following:

Cl

COCH,

// \ μ v nirnvn ./\/ΝΗ '

V ⁷ NH

C = O

NHCOCH,

Cl

COCH,

yV-N = N-CHCONH- / Y ^NH 'V_ _n

NHCOCH.,

COCH,
N = N-CHCONII- /

γ Cl

NH

C = O

ci-Λ.

/ V__ _CH

Il ^{L 11} J

V ^{/ X} NH-

NHCOCH.,

COCH,

N = N-CHCONH- / / ^Nh '"> _ _n

NH

CH,

NHCO-

> ■■ Cl

example 1

21.9 g of 4,6 - dichloro - 3 - amino - acclanilid become with K) OmI glacial acetic acid and 30 ml of 31% hydrochloric acid Stirred for 2 hours at room temperature and then at 0 to 5 C with 21 ml of 5N sodium nitrite solution diazotized. The mixture is left to stir for 30 minutes and the excess nitrite is destroyed with sulfamic acid and clarifies.

24.4 g of 5-acetoacetylamino-benzimidazolone are dissolved in a mixture of 50O ml of water, 27 ml of 33% strength sodium hydroxide solution and 5 ml of a 10% strength aqueous solution of the reaction product of 1 mol of slearyl alcohol and 20 mol of ethylene oxide. The coupling component is precipitated at 15 to 20 ° C. by collapsing 17.5 ml of glacial acetic acid. The diazonium salt solution is then slowly run into the suspension of the coupling component at 20 ° C. The pH value is increased to about 6 by simultaneous addition of about 365 ml of 5N sodium hydroxide solution , 3. After the coupling has ended, the mixture is heated to 95 ° C. and kept at this temperature for 30 minutes. It is then filtered off, washed and dried.

42 g of the dry Pigmcntpiilvers are with 450 ml of dimethylformamide refluxed for 1 hour. After cooling to 50 ° C., it is suctioned off.

washed with whiskey, dried and ground. The thus obtained monoazo pigment of the formula

(Ί

OC )

corn,

NN CU CONII

NH _x

C = O

NH

NHCOCH,

shows when working in a lacquer, in a printing ink, in polyvinyl chloride or in a spinning mass Cl very pure, orange-yellow colorations from an excellent J

Light and migration protection. 15 / y \

B is ρ ic I 2 \ J

18.5 g of 4 - chloro - 3 - amino - acetanilide willow with

100 ml glacial acetic acid and 25 ml concentrated hydrochloric acid NIlCOCH,

Stirred for 2 hours at room temperature and then at 0 to 10 C with 20.5ml of 5N sodium nitrile solution diazotized. The mixture is stirred for 30 minutes and the excess nitrite is destroyed with sulfamic acid and clarifies. The diazonium salt is then dissolved at room temperature gradually zi; a suspension of 28.1 g of 7-Clilor-5 - Add acetoacetylamino-benzimidazolone in 350 ml of pyridine. When the feed is complete Stirred for 1 hour and then filtered off. washed with water and dried at 60 ° C. 48 g of the dry pigment powder are refluxed with 580 ml of glacial acetic acid for 1 hour. To Cooling to 50 ° C. is filtered off with suction, washed with water, dried and ground Monoazo pigment of the formula

COCH,
= N-CH-CONH-Z

C = O

results when incorporated into a printing ink, in polyvinyl chloride, in a varnish or a spinning must have very pure, greenish yellow colorations of excellent quality Lightfastness and immaculate migration fastness.

Example 3

19.9 g of 2-chloro-5-methyl-4-amino-acetanilide are stirred in 80 ml of 5N hydrochloric acid for about 1 hour. It is then diluted to about 250 ml with ice water and slowly diazotized at 0 to 5 ° C riii; 20.5 ml of 511 sodium nitrite solution. Leave for 30 minutes stir, destroy the excess nitrite with sulfamic acid and clear.

23.5 g of 5 - acetoacetylamino - bcnzimidazolon are in 300 m! Slurried 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 over the course of 2 hours at 10 to 15 ° C. to a mixture of 100 ml of 4N sodium acela (solution, 20 ml of glacial acetic acid and 10 ml of an 10% strength aqueous solution of the reaction product of 1 mol After coupling is complete, the pigment ^{suspension is heated for 1 hour to 90 °} C. The pigment is filtered off with suction while hot, washed salt-free with water, dried at 60 ° C. and the ground product is stirred in 300 ml of dimethylformamide 6O ⁰ C is suction filtered, the pigment washed with methanol, dried and ground.

The thus obtained monoazo pigment of the formula

CH ₃ CONH

COCH ₃

= N-CH-CONH-ZV ^NHx

C = O

NH '

results when incorporated into an alkyd melamine resin clear lacquer and then applying the pigmented lacquer on test cards over black and white Background after 30 minutes of baking at! 40 'C bright orange colorations of high transparency, perfect fastness to overcoating and excellent lightfastness.

Example 4

33.0 g of 5-chloro-2-methyl-4- (2'.4'-dichlorobenzoylimino) aniline are introduced into 100 ml of 5N hydrochloric acid at 80 ° C. with stirring. After 10 minutes, cool it is reduced to room temperature and the suspension is then left to stir overnight. The next morning * is diluted with ice water to about 250 ml and at 5 ° C with 20.5 ml of 5N sodium nitrite solution made to measure : diazotized after consumption. The mixture is left to stir for 30 minutes, the excess nitrite is destroyed with amido ; ulfonic acid and clarifies.

27.0 g of 7-chloro-5-acetoacetylamino-benzimidizolone are suspended in 300 ml of water and dissolved by adding 15 ml of 33% strength sodium hydroxide solution. The clarified alkaline solution is added dropwise at the same time as the diazonium salt solution at 10 to 15 C with stirring over the course of an hour to a mixture of 2 (X) 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 from 1 mole of stearyl alcohol and 20 moles of ethylene oxide. After the coupling has ended, the pigment suspension is heated to 90 to 95 ° C. for 1 hour. The pigment is suctioned off while hot. washes salt-free with water, dries at 60 ° C. and stirs the ground orange-brown product in 500 ml of glacial acetic acid. The suspension is heated to 100 ° C. with stirring, the color gradually changing to yellow. After heating for 3 hours, the yellow pigment is filtered off with suction. washes

509 686/322

acid-free with methanol, dries and grinds. The pigment of the formula thus obtained

Cl

Cl -

CONH

COCII.,

- CH - CONII--

C O

results when incorporated into polyvinyl chloride, in one Varnish, a printing ink or a spinning mass are pure yellow colorations of perfect migration and excellent lightfastness.

If, in the above example, the equivalent is used instead of V-Chloi-S-aectoacetylamino-benzimidazolone Amount of 5-acetoacetylamino-benzimidazolone, a reddish-tinged yellow pigment is obtained which after One color in a printing ink, a varnish, in polyvinyl chloride or in a spinning mass reddish yellow Dyeings with similarly good fastness properties 15 results.

The following table contains a number of further components that can be used in accordance with the method as well as the color tones of the graphic prints of the diazo pigments produced from them in substance:

Diazo component Coupling ComponMilc

l'arbton

3-amino-acclanilid

the same

4-chloro-3-amino-acetanide

the same

4,6-Diehlor-3-amino-acetanilide desgl.

4-chloro-6-methyl-3-amino-acctanilide desgl.

4-Bromo-f> -methyl-3-amino-acetanilide the same

6-methyl-3-amino-acetanilide desgl.

4,6-dimethoxy-3-amino-aeelanilide desgl.

4,6-dichloro-3-aminopropionanilide desgl.

3-benzovlamino-aniline

the same

3- (2 ', 4'-dichlorobenzoy-amino) -aniline desgl.

2-chloro-5- (2'-chlorobenzoyl-amino) aniline

2-chloro-5- (2 \ 4-dichlorobenzoylamino) aniline

the same

2.4-dichloro-5-l4'-chloro-3-methylbenzoylamino) aniline desgl.

2.4-dichloro-5- (4'-bromobenzoylamino) -aniline desgl.

2-bromo-5-benzoy! Amino-aniline desgl.

2-chloro-4-methyl-5- (2'.5'-dichlorobenzoylamino) aniline the same

S-acetoacctylamino-benzimidazolone

T-chloro-S-aeetoucctylarnino-benzimidazolone S-acetoacelylamino-benzimidazolone

T-bromo-S-acetoacetylamino-benzimidazolone fvMethyl-S-acetoacetylamino-benzimidazolone T-methoxy-S-aeeloacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone

e-chloro-.S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone

o-chloro-S-acetoaeetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone

T-chloro-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone

o-Bromo-S-acetoacelylamino-benzimidazolone T-chloro-S-acetoacetylamino-benzimidazolone T-methyl-S-acetoacetylamino-benzimidazolone T-chloro-S-aceloacetylamino-benzimidazolone o-Bromo-S-acetoacetylamino-benzimidazolone T-ethoxy-S-acetoacetylamino-benzimidazolone o-methylo-acetoacetylamino-benzimidazolone S-acetoacetylaminobenzimidazolone

o-chloro-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone

T-chloro-S-acetoacetylamino-benzimidazoion S-acetoacetylamino-benzimidazolone

T-bromo-S-acetoacetylamino-benzimidazolone T-chloro-S-acetoacetylamino-benzimidazolone

T-methyl-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone
T-chloro-S-acetoacetylamino-benzimidazolori S-acetoacetylamino-benzimidazolone

yellow

greenish yellow

greenish gclb

greenish yellow

reddish yellow

yellowish yellow

reddish yellow

reddish yellow

reddish yellow

reddish yellow

yellow

greenish yellow

yellowish yellow

reddish yellow

yellow

reddish yellow

greenish yellow

greenish yellow

reddish yellow

yellowish yellow

yellow

yellow reddish yellow

yellow reddish yellow

yellow yellow

yellow

yellow

greenish yellow

reddish yellow

T-Methoxy-S-acetoacetylamino-benzimidazolone yellowish yellow

^; γ ^> 4, Sj- ^ , I |; r ^: -5. ^: 3i _r

11th

continuation

Diazo component

2-methyl-5- (2 ', 4'-dichloro-benzoylamino) -aniline the same

4-methyl-5- (4'-chloro-2'-meth () xybcnzoylamin aniline the same

2-methoxy-5- (4'-chloro-3'-methylbenzoylamino) aniline the same

4-amino-acetanilide desgl.

2-chloro-4-aminoacctanilide desgl.

B-ChloM-amino-acetanilide the same

the same

2,5-dichloro-4-amino-acetanilide desgl.

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

the same

2-melhoxy-5-methyl-4-aminoacelanilide the same

2,5-dimethoxy-4-amino-acetanilide desgl.

2,5-dichloro-4-aminopropionanilide desgl.

4-benzoylamino-aniline like.

4- (4-chlorobenzoylaminol aniline the same

4- (2'.4'-dichlorobenzoy-amino) -aniline desgl.

3-chloro-4- (4'-chloro-benzoylamino) -aniline desgl.

3-Chloro-4- (4'-chlorobenzoylamino) -aniline 3-Ch! Or-4- (2 ', 4'-dichlorobenzoylaminol-aniline the same

3-chloro-4- (4'-chloro-3'-methylbenzoylamino) -aniline desgl.

2,5-dichloro-4- (4'-chloro-2'-methoxybenzoylamino) aniline the same

3-bromo-4- (4'-chlorobenzoylamino) -aniline desgl.

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

K iipplungskomponenle l-arblon

S-aeetoacetylamino-benzimidazolone yellow

fvMethyl-S-acetoacctylamino-ben / .imidazolon reddish yellow

S-acetoacelylamino-benzimidazolone reddish yellow

fi-chloro-S-acetoacetylamino-benzimidazolone yellow

S-aceloacelylamino-benzimidazolone reddish yellow

T-chloro-S-acetoacetylamino-benzimidazolon green-tinged

S-acetoacetylamino-benzimidazolone reddish yellow

V-chloro-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone yellow

V-methyl-S-aceloacetylamino-benzimidazolone yellow

S-acetoacelylamino-benzimidazolone reddish yellow

o-chloro-S-acetoacetylamino-benzimidazolone greenish yellow

T-Methoxy-S-aeetoacetylamino-benzimidazolone reddish yellow

S-aceloacetylamino-benzimidazoIon yellow

T-chloro-S-acetylamino-benzimidazolone yellow

S-acetoacelylamino-benzimidazolone reddish yellow

V-chloro-S-acetoacetylamino-benzimidazolone green-tinged

T-methyl-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone reddish yellow

a-Methyl-S-acetoacetylamino-benzimidazolone reddish yellow

S-acetoacetylamino-benzimidazolone orange

T-bromo-S-acetoacetylamino-benzimidazolone reddish yellow

S-aceloacetylamino-benzimidazolone yellow

o-chloro-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone reddish yellow

o-Bromo-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone yellow

T-chloro-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone yellow

T-Ethoxy-S-acetoacetylamino-benzimidazolone reddish yellow

S-acetoacetylamino-benzimidazolone yellow

T-chloro-S-acetoacetylamino-benzimidazolone yellow

ö-Methyl-S-acetoacetylamino-benzimidazolone yellow

.VAeetoacetylamino-benzimidazolone yellow

o-Bromo-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone yellow

y-Methoxy-S-aceloacetylamino-benzimidazolone reddish yellow

S-acetoacetylamino-benzimidazolone yellow

T-chloro-S-acetoacetylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone yellow

o-Methyl-S-acetoacelylamino-benzimidazolone yellow

S-acetoacetylamino-benzimidazolone reddish yellow

T-bromo-S-acetoacetylamino-benzimidazolone yellow

Claims (1)

Claims: 1. Monoazopigniente of the general formula X ₁ Sx wherein R, X ₁ and X _{2 are} identical or different and represent a hydrogen atom, a chlorine or bromine atom, the methyl, ethyl, methoxy or ethoxy group and Z the methyl or ethyl group or a phenyl radical which has one or two chlorine or May have bromine atoms, methyl or methoxy groups as substituents, and in which the group —NHCOZ is in the meta or para position to the azo group.