DE2158806A1 - New disazo pigments and processes for their production - Google Patents

Description

CIBA-GEIGY AG, CH-4002 Basel

Dr. P. 7- -. Ttrln ε · 'η. - Dr. E. Assmann Dr.R. Küsr .: "v - r - L- ·; -?!. Piiya.R. ISü

Patent attorneys Z I 0 O O U D

8 monks 2, ßröuhousstraßo 4 / III

Case 3-7275 / =

Germany

New disaso pigments and processes for their production

The subject of Swiss patent specification No. 448.330 is a process for the preparation of water-insoluble substances Disazo dye, which consists in the fact that one amines of the formula

(1) H ₂ NR-CF ₅ I.

wherein R is a benzene radical, R _{1 is} an alkyl, alkoxyalkyl, phenoxyalkyl, cycloalkyl, aralkyl or aryl radical and X is an oxygen or sulfur atom and in which the group XR-. is in the ortho or para position to the amino group, with a dihalide of a dicarboxylic acid of the formula

CH, CH, -

co ·? ■ co

. (2) HOOC-B-N = N-CH-CONH-A-NHCO-CH-N = N-B-COOh

209 825/1091

where A and B are arylene radicals, condensed in a molar ratio of 2: 1.

After this procedure receives. one water-insoluble pigments, 'which are characterized by high light and migration fastness.

In pursuing this inventive concept, it has now been found that disazo pigments of similar good fastness properties of the formula

CH ^ CH,:

CO CO - XR ₁

A-NHCO-B-N = N-CH CH-N = N-B-CONH ^ f

ⁿ 2 j CONH-A-NHCO

\ j Ji η vC

arrives, wherein A and B are arylene radicals, FL is an alkyl, alkoxyalkyl, phenoxyalkyl, cycloalkyl, aralkyl or aryl radical, X a Sulfur or, in particular, a 0 atom, Rp is the group XR or mean a chlorine atom when a) a dihalide of a dicarboxylic acid of the formula

COCH, COCH ^ H00C-BN = N-CH0CNH-A-NHC0CH-N = NB-C00H

with an aminobenzene of the formula

209825/1091

FiΛ

ts) Η, Η

CF,

condensed in a molar ratio of 1: 2, or

b) the diazo compound of an amine of the formula

-NHCC-B-NH ₂

CP

with a diacetoacetyl-arylenediamine of the formula

(7) H ₃ CCOCH ₂ CONH-A-NHCOCH ₂ -COCh

couples in a molar ratio of 2: 1.

Since the dyes according to the invention are pigments, water-solubilizing groups are in particular acidic, water-solubilizing groups, such as sulfonic acid or carboxylic acid groups, of course locked out.

Disazo pigments of the formula are of particular interest

209825/1 091

_ it _

(T) P

(8th)

A-HNCO

CF,

where X, and Y, hydrogen or halogen atoms are alkyl or alkoxy groups, Y is a hydrogen or halogen atom, an alkyl, alkoxy or carbalkoxy group and ρ is the number 1 or 2, Rl has the meaning given and R- , represents a chlorine atom or the group OR ₁ .

The dicarboxylic acids of the formula (4) are conveniently obtained by coupling the diazo compound of a monocarboxylic acid of the formula

HOOC-B-NH ₂

in which B preferably denotes a benzene radical, with a diacetoacetyl-arylenediamine of the formula (7) in the molar ratio

209825/1091

2: Ij, where the arylene radical A in the formula (7) is preferred a. Phenylene radical and in particular a radical of the formula

means, in which X, and Y, hydrogen or halogen atoms, Mean alkyl or alkoxy groups.

The diacetoacetyl-arylendiamines of the formula (7) are obtained in a simple manner by the action of diketene or acetoacetic ester on aromatic diamines, such as 1,4-diaminobenzene,
I, j5-diaminobenzene,
l ^ -Diamino- ¹ ! -methylbenzene,!, jS-diamino- ^ - methoxybenzene, 1, jS-diamino- ^ - chlorobenzene, ■ 1,3-diamino-2,5-dichlorobenzene, 1,4-diamino-2 -chlorobenzene _i;

1,4-diamino-2-bromobenzene, 1,4-diamino-2-cyanobenzene, 1,4-diamino-2,5-dichlorobenzene, 1,4-diamino-2-methylbenzene,!, ^ - Diamiho - ^ - trifluoromethylbenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2-methoxybenzene, 1,4-diamino-2,5-dimethoxybenzene, 1, ty-diamino - ^ - chloro-5-methylbenzene, l, 4-diamino-2-chloro-5-methoxybenzene,

209825/1091

l, 4-diamino-2-chloro-5-ethoxybenzene, 1,4-diamino-2,5-diethoxybenzene, 1,3-diamino-4,6-dimethoxybenzene, 1,> -Diamino-2,6-dlmefchylbenzol, 2,8-diamino earring, 4,11-diaminofluoranthene, 2,6- or 1,5-diaminonaphthalenes.

The compounds of the formula (7) are diazotized with aromatic aminocarboxylic acids, preferably aminobenzenecarboxylic acids and in particular those of the formula

COOH

coupled, in which Y is a hydrogen or halogen atom, an alkyl, alkoxy or CarbaIkoxygruppe and ρ is the number 1 or 2. The following aminocarboxylic acids may be mentioned as examples:
3-aminobenzoic acid,
4-aminobenzoic acid,
3-chloro-4-aminobenzoic acid _J ^ -chloro - ^ - aminobenzoic acid, 4-bromo-3-aminobenzoic acid, ^ -fluoro-J-aminobenzoic acid, 2,4-dichloro-5-aminobenzoic acid, 3-methyl-4-aminobenzoic acid, 4-methyl- ^ xaminobenzoic acid, 2,4-dimethy1-5-aminobenzoic acid,

209825/1091

- 1 -

4-methoxy-3-aminobenzoic acid
5-nitro-4-aminobenzoic acid
3-Amino-terephthalic acid monoethyl ester 3-Amino-terephthalic acid monoethyl ester.

The azodicarboxylic acids of formula (4) are with agents which are capable of converting carboxylic acids into their halides, e.g. the bromides or chlorides, for example with phosphorus halides, e.g. phosphorus trichloride, phosphorus pentachloride or oxychloride, but especially thionyl chloride. Treatment with such acid-halogenating agents becomes appropriate in inert organic solvents such as chlorobenzenes, e.g. mono- or dichlorobenzene, toluene, xylene, benzene or nitrobenzene. When using thionyl chloride as an acid-chlorinating agent, it proves to be advantageous to work in the presence of dialkylformamides, especially dimethylformamide.

When preparing the carboxylic acid halides, it is generally expedient to use those prepared in an aqueous medium To dry azo compounds first or to free them azeotropically from water by boiling in an organic solvent. These Azeotropic drying can, if desired, be carried out immediately before the Treatment with acid-halogenating agents can be carried out.

The dicarboxylic acid halides obtainable in this way are reacted with aminobenzenes of the formula (5).

Examples are:
2-methoxy-4-chloro-5-trifluoromethylaniline,

209825/1091

2,4-dimethoxy-5-trifluoromethylaniline, 2,4-diethoxy-5-trifluoromethylaniline, 2,4-di-n-propoxy-5-trifluoromethylaniline, 2,4-diisopropoxy-5-trifluoromethylaniline, 2,4-dicyclohexyloxy-5-trifluoromethylaniline, 2,4-diphenoxy-5-trifluoromethylaniline, 2,4-di- (o-methylphenoxy) -5-trifluoromethylaniline, 2,4-di- (p-methylphenoxy) -5-trifluoromethylaniline, 2,4-di- (p-methoxyphenoxy) -5-trifluoromethylaniline, 2,4-di- (o-chlorophenoxy) -5-trifluoromethylaniline, 2,4-di- (p-chlorophenoxy) -5-trifluoromethylaniline,

2,4-di- (p-bromophenoxy) -5-trifluoromethyl aniline,

2,4-di- (2 ^f , 4'-dichlorophenoxy) -5-trifluoromethylaniline, 2,4-di- (cc-naphthoxy) -5-trifluoromethylaniline, 2,4-di- (β-naphthoxy) -5 -trifluoromethylaniline, 2,4-di- (p-diphenyloxy) -5-trifluoromethylaniline, 2,4-di- (2 ', 4', 5'-trichlorophenoxy) -5-trifluoromethylaniline, 2,4-di- ( 2 '., JJ ¹ , 4' ,, 5 ¹ J 6 '-pentachlorophenoxy) -5-trifluoromethylaniline 2,4-di- (p. Tert-amylphenoxy) -5-trifluoromethylaniline, 2,4-diphenylmercapto- 5-trifluoromethylaniline, 2-ß-naphthoxy-4-chloro-5-trifluoromethylaniline, 2-phenoxy-4-chloro-5-trifluoromethylaniline, 2- (4'-chlorophenoxy) -4-chloro-5-trifluoromethylaniline, 2- ( 4'-methylphenoxy) -4-chloro-5-trifluoromethylaniline, 2- (4'-methoxyphenoxy) -4-chloro-5-trifluoromethylaniline, 2- (p. Tert.-amylphenoxy) -4-chloro-5-trifluoromethylaniline,

2- (2 ¹ , 4 ^f , 5'-trichlorophenoxy) -4-chloro-5-trifluoromethylaniline. 2- (j3-phenoxyethoxy) -4-chloro-5- trifluoromethylaniline 2,4-di- (j3-ethoxy-ethoxy) -5-trifluoromethylaniline

2098 2 5/1091

The condensation between the carboxylic acid halides of the type mentioned at the outset and the amines is expediently carried out in an anhydrous medium. Under this condition, it generally takes place surprisingly easily even at temperatures which are in the boiling range of normal organic solvents, such as toluene, monochlorobenzene, dichlorobenzene, trichlorobenzene and nitrobenzene. To accelerate the reaction it is generally advisable, an acid binding agent, etc. such as anhydrous sodium acetate or pyridine to use. The dyes obtained are partly crystalline and partly amorphous and are mostly obtained in very good yield and in a pure state. It is advisable to first remove the acid chlorides obtained from the carboxylic acids. In some cases, however, a deposition of the acid chlorides can be dispensed with without damage and the condensation can take place immediately after the preparation of the carboxylic acid chlorides. . ™

According to embodiment b) of the invention Process is the diazo compound of an amine of the formula (6) with a diacetoacetylarylenediamine of the formula (7) in 2: 1 mole ratio coupled. Diazo compounds are preferably used of amines of the formula

- NHCO

2 0 9 8 2 5/1 09 1

where R ,, R ", Xj Y and ρ have the meaning given.

The coupling takes place preferably in a weakly acidic medium, expediently in the presence of conventional ones Coupling promoting means. In particular, dispersants may be mentioned as coupling promoting agents, for example Aralkyl sulfonates, such as dodecylbenzenesulfonate or 1,1'-dinaphthylmethane-2,2'-disulfonic acid or polycondensation products of alkylene oxides. The dispersion of the coupling component can also advantageously be protective colloids, for example Methy! Cellulose, or smaller amounts of inert ones, in water contain sparingly soluble or insoluble organic solvents, for example optionally halogenated or nitrated aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene or nitrobenzene, as well as aliphatic halogenated hydrocarbons, such as hydrocarbon tetrachloride or trichlorethylene, also with water miscible organic solvents such as acetone, methyl ethyl ketone, Methanol, ethanol or isopropanol.

The coupling can also be carried out advantageously in such a way that an acidic solution of the diazonium salt is used continuously combined with an alkaline solution of the coupling component in a mixing nozzle, with an immediate coupling of the components takes place. Care must be taken that the diazo component and the coupling component are in equ! Quantities are present in the mixing nozzle, whereby it is

209-82 5/109 1

geous proves to use a slight excess of the diazo component. The easiest way to do this is to check the p "value of the liquid in the mixing nozzle. A strong turbulence between the two solutions must also be ensured in the mixing nozzle. The resulting dye dispersion is continuously withdrawn from the mixing nozzle and the dye is separated off by filtration. It has proven to be advantageous to post-treat the pigments obtained by the coupling route with an organic solvent, preferably boiling above 100.degree. Particularly suitable are benzenes substituted by halogen atoms, alkyl or nitro groups, such as xylenes, chlorobenzene, o-dichlorobenzene or nitrobenzene and pyridine bases such as pyridine, piceline or quinoline, and ketones such as cyclohexanone, ethers such as ethylene glycol monomethyl or monoethyl ether, Amides, such as dimethylformamide or N-methylpyrrolidone, and sulfoxone.

The aftertreatment is preferably carried out by heating the pigment in the solvent to 100 to 150 ° C., with in many cases a coarsening of the grain occurs, which has a favorable effect on the lightfastness and migration fastness of the material obtained Pigments.

The new dyes are valuable yellow pigments, which are characterized by an unusually high lightfastness distinguish. They can be used for a wide variety of pigment applications, e.g. in finely divided form for Coloring of cellulose ethers and esters or of super polyamides

209825/1091

respectively Super-polyurethanes or polyesters in the spinning pulp, as well as for the production of colored lacquers or lacquer formers, solutions and products made of acetyl cellulose, nitrocellulose, natural resins or synthetic resins, such as polymerization resins or condensation resins, e.g. aminoplasts, alkyd resins !!, Phenoplasts, polyolefins, such as polystyrene, polyvinyl chloride, Polyethylene, polypropylene, polyacrylonitrile, rubber, casein, silicone and silicone resins. They can also be beneficial Use in the manufacture of colored pencils, cosmetic preparations or laminating plates.

Compared to the dyes of the German patent specification 1 ISO 165 (Case 3782) are characterized by those according to the invention Dyes are characterized by better lightfastness.

In the examples below, the parts mean, unless otherwise stated, parts by weight, the Percentages by weight and temperatures are given in degrees Celsius.

209825/1091

Example 1.

68.4 parts of the dry dye from 2 moles of diazotized 4-chloro-j5-aminobenzoic acid and 1 mole of 2,5-bisacetoacetylamino-1,4-dichlorobenzene are stirred in 1000 parts of o-dichlorobenzene with 5 parts of dimethylformamide and heated to 95-100. Let in 10 to 15 minutes Add 52.8 parts of thionyl chloride and then heat f

2 hours at 105 to 110 °. After the hydrochloric acid evolution Has subsided, it is allowed to cool to 40, the dye carboxylic acid chloride formed is filtered off with suction and washed with 500 Share cold o-dichlorobenzene.

An amount of the o-dichlorobenzene-moist product corresponding to 5 * 6 parts of dry acid chloride is added to 100 parts of o-dichlorobenzene. 0.05 parts of thionyl chloride and heated to 95 to 100 and a solution of 6.45 parts of 2, 4-Diparachlorphenoxy-5-trifluormethy! Aniline and 1.0 part of pyridine were added in 50 parts of o-dichlorobenzene. The mixture is then stirred for 12 hours at 140 to 145 °, then allowed to cool to 100 °, filtered and washed with hot o-dichlorobenzene until the piltrate is completely colorless. It is then washed with cold methanol and finally with hot water. After drying, 8.9 parts of a loose, soft pigment are obtained which, when rolled into polyvinyl chloride, have brilliant greenish yellow tones with excellent migration properties

Results in lightfastness. The pigment obtained in this way corresponds to the formula 209825/1091

-U-

I ^J Cl

co I

-N = N-CH-COHnAJ

ι I

Cl Cl

Cl

co

CONH

CK

CP,

Example 2.

8.85 parts of 6 ~ chloro-4-phenoxy -> - (3 ^t -amino-4 ^l -chlorobenzoylamino) -l-trifluoromethylbenzene are stirred in 50 parts of glacial acetic acid with 6.0 parts of hydrochloric acid ^ 0% and by adding 20 parts Ice cooled to -5 °. 5.0 parts of 4N sodium nitrite solution are allowed to flow in while stirring, the temperature being kept at 0 to 2 by adding ice . First a clear, yellowish solution is obtained, from which the diazonium salt partially separates out in crystalline form after some time. Any excess of nitrous acid is destroyed by adding urea and the diazo solution with 10 parts of crystalline. Natriun acetate set to p _H. 4

On the other hand, 5.4 parts of 2-chloro-5-methoxy-1,4-bis-acetoacetylaminobenzene are dissolved in 150 parts of water / water at 40 ° to 45 ° with 6 parts of sodium hydroxide solution, filtered clear with 0.2 part of blood charcoal and after adding 5 parts of n-butyl

209.82 5/109 1

sulforicinoleate was added dropwise to the dialysis solution with thorough stirring. The coupling takes about an hour, and the temperature of the mixture rises to 20 to 25 ° during this time. The diazo compound, which is still clearly detectable after the dropwise addition, disappears completely after brief heating to 30 to 35. The mixture is then heated to 80 to 85 j in one hour, filtered hot and the filter residue is washed salt-free with hot water. After drying at 95 to 100 in vacuo, the dye is obtained in a hard, poorly spreadable texture. The pigment obtained is stirred in 150 parts of nitrobenzene and heated to 140 to 145 ° for 3 to 4 hours. After this time all coarse and hard particles have disappeared, and uniform, regular, fine yellow needles can be seen under the microscope. It is allowed to cool to 100 °, filtered and washed with hot nitrobenzene and then with methanol until the filtrate is completely colorless. After drying, a loose, soft pigment of the formula is obtained

A-NHCO I. 9 ¹

I Λ Γ 1 N = N-A I

CJF, U-N = N-CH-CQNH-A I V?

3 Y U-NHCOCH I I

ci TI ^C0NH lY _P1

OCH ₅ CO V ~ ^C]

CH 2 0 9.8 2 5/1 09 1

that can be easily distributed in plastics and paint media. The colorations in PVC result in brilliant reddish yellow tones with very good migration and lightfastness.

Further pigments are listed in the table below., which are obtainable by one of the processes in Examples 1 to 2. The column I contains the coupling components used acetoacetic arylides underlying diamines., Column II the ones used for the diazo component Aminobenzenecarboxylic acids and column III the amines used as arylide bases, in column IV the shade of a 0 is Color of the pigment specified in PVC,

209.825 / 1 09 1

I. II III IV dd 1. 2., 5-dichloro
1,4-diamino
benzene 4-chloro-3-ami-
no be nz ο es aure - 2,4-di- (p-chlorine-
phenoxy) -5-tri-
fluoromethylani-
lin green
prickly
yellow Tt
• i 2 " Tt dd 2,4-diphenoxy-5-
trifluoromethyl
aniline H dd It dd 2 ₃ 4-di- (p-methoxy-
phenoxy) -5-tri-
fluo2? methylaniline » Tt 4th dd dd 2,4-di- (p-methy1-
phenoxy) -5-tri-
fluoromethylaniline dd 5 It dd 2- (p-chlorophenoxy) - "
4-chloro-5-trifluoro-
methy! aniline j 6th » dd 2-phenoxy-4-chloro
5-trifluorme-)
thylaniline 7th Tt Il 2- (2 ', 4'-DiChIOr- ¹
phenoxy) -4-chloro-;
5-trifluoromethyl- '.
aniline 8th dd dd 2-methoxy-4-chloro
5-trifluorraethyl- [
aniline 9 dd dd 2- (ß-naphthoxy) -
4-chloro-5-fcri-
fluoromethylani
lin

2 09.825 / 1091

II

2, 5-dichloro-ι 4-chloro-3-amino-1,4-diamino-benzoic acid · benzene

2-chloro-5-

methyl-1,4-

diaminobenzoli

diaminobenzene III

2- (4'-methoxyphephenoxy) -4-chloro-5-trifluoromethylaniline

2,4-diphone <- 'xy-5-trifluoromethy1-aniline

2,4-di- (p-chlorophenoxy) - ^ - trifluoromethylaniline

2j 4-di- (p-methoxyphenoxy) -5-trifluoromethyl aniline

2,4-di- (p-methylphenoxy) -5-trifluoromethylaniline

2-phenoxy-4-chloro-5-trifluoromethylaniline

2- (β-naphthoxy) -4-chloro-5-trifluoromethyl lani ILn

2- (2 ', 4', 5'-TrI chloropheno , y) - 4-

hlor-5-tr .f Luormethy lanil.η

2- (p-metho .yphono- " xy) -4-chloro-f3-tri- j f luormethy larii 1 in

2,4-diphenoxy-5 ~

rifluoromethylaniline

2- (p-Chlorophenoxy) - "4-chloro-5-trifluoromethylaniIη j

IV

green-stj chi, yellow.

20 9 82-5 / 109

2-methy3-2,4-diaminobenzene

2.5-1) 3 me thy 1-1,4-diamino- benzene

II

4-chloro-3-aminobenzoic acid

2-methyl-5-methoxy-1,4-diaminobenzene

2,5-diniethoxy-1,4-diamino benzene

1,4-Dlaminobenzene

2,5-diethoxy-1,4-diaminobenzene

2-methyl-5-chloro-1,4-di- aminobenzene

aminobenzoesaui'e III

IV

2,4-Diphenoxy-5 green trifluoromethyl tinged aniline yellow

2-methoxy-4-chloro-5-trifluoromethylaniline

2,4-di- (p-chloro-yellow phenoxy) -5-tri- j fluoromethylaniline

2, 4-diphenoxy-5-trifluoromethylaniline

2-phenoxy-4-chloro red-5-trifluoromethyl- ' pungent aniline 'j yellow

2,4-di- (p -raethy1-'yellow phenoxy) -5-tri-; fluoromethylaniline \

2- (p ~ methoxyphe-; red-

noxy) -4-chloro-5-!

trifluoromethyl yellow aniline

2-methoxy-4-chloro-5-trifluoromethyl-aniline

2,4-diphenoxy-5r trifluoromethyl aniline

2 ₃ 4-di- (4'-chloro-yellow phenoxy) -5-trifluoromethylaniline

reddish yellow

greenish yellow

209825/1091

I. II III IV 33 2-methyl-5-
chlorine-1,4-di-
aminobenzene 2,4-dichloro-5-
aminobenzoic acid 2-phenoxy-4-
chlorine-5-trifluoro-
methy! aniline green
prickly
yellow 34 Il 4-methyl-3-amino
benzoic acid. Il It 35 It Il 2,4-di- (4'-methy1-
phenoxy) -5-tri-
fluoromethy! aniline It 36 y It 4-methoxy-3-
aminobenzoic acid 2, 4-diphenoxy ~ 5-
trifluoromethyl
aniline . ti 37 2-chloro-5-
methoxy-1,4-
diaminobenzene 4-chloro-3-amino-
benzoic acid 2- (p-chloropheno-
xy) -4-chlorine-5-
trifluoromethyl
aniline yellow 38 It I! 2-PhCnOXy - ^ - ChIOr-
5-trifluoromethyl-
aniline It i
t 39 It 2- (2 ', 4' - (31ChIOr-
phenoxy) -4-chlorine-
5-trifluoromethyl-
aniline It 40 π Il 2,4-di- (p-chlorine-
phenoxy) -5-tri-
fluoromethy! aniline It 41 Il Il 2,4-di (p-methyl-
phenoxy) -5-tri-
fluoromethylaniline It 42 Il It 2j 4-diphenoxy-5-
trifluoromethyl
aniline It 43 It Il 2- (a-naphthoxy) -
4-chloro-5-tri-
fluoromethylaniline ti 44 H H 2,4-di- (p-bromophe-
noxy) -5-trifluoro-
methylaniline Il

ο, ι

I. II III IV 2-chloro-5-
methoxy-1,4-
diaminobenzene 4-chloro-j5-amino-
benzoic acid 2,4-Di- (n-Bu-
toxy) -5-tri-
fluoromethyl
aniline yellow 46. 2-methoxy-1,4
diaminobenzene It 2,4-di- (P-chloro
phenoxy) -5-tri-
fluoromethylaniline Red
prickly
yellow 47 It. ti 2-phenoxy-4-chloro
5-trifluoromethyl-
aniline - yellow 48- It It 2 _J 4-di- (p-raethyl-
phenoxy) -5-tri-
fluoromethylaniline dd 49 It dd 2,4-diphenylmer dd raethylaniline 50 It 2- (2 ^ 4'-DiChIOr-
phenoxy) ~ 4-chloro-
5-trifluoromethyl-
aniline dd 51 Il It 2- (p-chlorophenyl-
mercapto) -4-chlorine-
5-trifluoromethyl * -
aniline dd 52 dd It 2- (2 ', 4', 5 ^ TrI-
chlorophenoxy) -4-
chlorine-5-tririuor-
methylaniline dd 53 Il It 2-cyclohexyloxy
4-chloro-5-tri-
fluoromethy! aniline It 54 Il ■ M 2- (p-methoxyphene-
oxy) -4-chlorine-
5-trifluoromethyl-
aniline It

209.825 / 1091

-. 22 -

I. II III IV 55 2-chloro-5-
methoxy-1,4-
diaminobenzene 4-chloro-3-amino-
benzoic acid 2- (ß-phenoxy) -
ethoxy-4-chloro
5-trifluoro
methylaniline yellow 56 2,5 dichloro
1st, 4-diamino
benzene ^ - chlorine - ^ - amino-
benzoic acid 2- (j3 -phenoxy) -
ethoxy-4-chloro
5-trifluoro
methylaniline green- ■
prickly
yellow 57 2,5 dichloro
1,4-diamino
benzene ^ - chlorine - ^ - amino--
benzoic acid 2, 4-Di- (JS-Ae-
thoxy) -ethoxy-
5-trifluoro
methylaniline green
prickly
yellow 58 2, 5-dichloro
1,4-diamino
benzene 3-amino-terere-
phthalic acid-4-
monomethyl ester 2,4-di- (P-chloro
phenoxy) -5-tri-
fluoromethylaniline yellow 59 2-chloro-5-
methyl-1,4
diaminobenzene 3-amino-ters
phthalic acid 4-
monomethyl ester 2., 4-di- (p-chlorine-
phenoxy) -5-tri-
fluoromethylaniline yellow 60 4,6-dichloro
1,5-diamino
benzene ^ -Chlor - ^ - amino-
benzenic acid 2, 4-di- (p-chlorine-
phenoxy) -5-tri-
fluoromethylaniline yellow

209825/1091

Example '6l

65 parts of stabilized polyvinyl chloride, 35 parts of dioctyl phthalate and 0.2 parts of the dye obtained according to Example 1 are stirred together and then rolled back and forth on a two-roll calender for 7 minutes at 140 °. You get a yellow colored film of very good light and migration fastness.

209825/1091

Claims (1)

Claims Disazo pigments of the formula OH CO -NHCO-B-F = IT-CH CH. CO CH-N = N-B-CONH CONH-A-NHCO where A and B are arylene radicals, R is an alkyl, alkoxyalkyl, phenoxyalkyl, cycloalkyl, aralkyl or aryl radical, X is a sulfur or, in particular, an O atom, R _{p is} the group XR, or a chlorine atom. Disazo pigments according to claim 1 of the formula COCH COCH, -N = li-CHCOHN- <r_> -NHCOCH-N = N- CONH ⁵ T HNCO wherein 'R has the meaning given in claim 1, R ^ is a chlorine atom or the group OR > Y is a hydrogen or halogen atom, an alkyl, alkoxy or carbalkoxy group and ρ is the number 1 or 2, X and Y, H - or halogen atoms, Mean alkyl or alkoxy groups. 209825/1091 5- Process for the production of disazo pigments formula OH, XR ₁ CO CO XR ₁ - A-NHGO-B-N = N-CH CH-N = N-B-GONH-A 2 j CONH-A-NHCO j .2 CP ₃ CF ₃ wherein A and B are arylene radicals, R _{1 is} an alkyl, alkoxyalkyl, Phenoxyalkyl, cycloalkyl, aralkyl, or aryl radical, X is Sulfur or, in particular, a 0 atom, Rp is the group XR, or mean a chlorine atom, characterized in that a) a dihalide of a dicarboxylic acid of the formula COCH, COCH, H00C-B-N = N-CH0CNH-A-NHC0CH-N = N-B-C00H with an aminobenzene of the formula a condensed in a molar ratio of 1: 2, or b) the diazo compound of an amine of the formula 2098Z5 / 1091 with a diacetoacetyl-arylenediamine of the formula , H ₃ CCOCH ₂ CONH-A-NHCOCH-COCh ₃ couples in a molar ratio of 2: 1. 4. The method according to claim 3, characterized in that that one of a carboxylic acid halide of the formula cioc starts out, in which Y is a hydrogen or halogen atom, an alkyl, alkoxy or carbalkoxy group and ρ is the number 1 or 2, X, and Y, H or halogen atoms, alkyl or alkoxy groups. 5. Process according to Claims 3 and K, characterized in that one of an aminobenzene of the formula starts out, in which R _{1 and R 3 have} the meaning given in claim 2. 6. Process for pigmenting high molecular weight organic material, characterized by the use of the dyes according to claims 1 to j5 ·. 7 · The pigmented material obtained according to claim 6. 209825/1091