DE1544453A1 - Process for the production of disazo pigments - Google Patents

Description

CIBA AKTIENGESELLSCHAFT, BASEL (SWITZERLAND)

Case 5585 / E Germany

Process for the production of disazo pigments

In the German patent specification 1 15O I65

(Case 3782) is the production of yellow disazo pigments by condensation of a dihalide of a diacid the formula

COCH, COCH, 1 3 ι 3 (1) HOOC-B-N = N-CH-CONH-A-NHCOCH-N = N-B-COOH,

wherein A and B represent aryl radicals, described with 2 mol of a primary monoamine. This method delivers a lot pure products with excellent pigment properties

0098U / 0726

15AAA53

however, the disadvantage that it has to be carried out in an organic solvent. On the other hand, in the US Patent 3,112,303 is the unilateral coupling of the 4,4-Bisacetoacetylamino ^t-3,3 -dimethy] _diphenyls with the diazo compound of the ^3-A mino-4-methoxy-benzanilides described. According to this method, in which the solution of the diazo compound is added to an acetic acid suspension of the coupling component in the presence of a dispersant, it is not possible to obtain disazo dyes even if 2 mol or more of the diazo compound is allowed to act on 1 mol of the coupling component.

It has now been found that disazo pigments of the formula

R _1x COCK, COCH ₃ R ₁ (2) / NX-BN = N-CH-CONH-A-NH-COCH-N = NB-XNv

P 'M *

R ₂ R ₂

obtained in good yield and purity if a) the aqueous-alkaline solution of a bisacetoacetyl compound the formula

(3) CH ₃ COCH ₂ CONH-A-NHCOCH ₂ COCH ₃ gradually de ^ to the solution of the amine of zoverbindung

0098U / 0726 bathroom

formula

(4) ^ ₂

R ₂

adds, where in the given formulas A and B arylene radicals, R, and Rp are hydrogen atoms, alkyl groups or aryl radicals mean, and in which the radicals R. and Rp also together with the nitrogen atom can form a heterocyclic ring, and X is a -CO- or -SOp group, or b) an acidic solution of the diazonium salt of the amine of the formula (4) with an alkaline solution of the coupling component of formula (3) continuously combined in a mixing nozzle, the coupling process at p "values should run between 3 and 6.

In the diazo components of the formula (4) to be used according to the process, B is preferably a benzene residue. Amines of the formula are of particular interest

(5)

wherein V is a hydrogen or halogen atom, an alkoxy or carbalkoxy group, X ,, Y and Z are hydrogen or Mean halogen atoms, alkyl, alkoxy, phenoxy, nitro, trifluoromethyl, cyano or carbalkoxy groups.

0098U / 0726 © ad

The following amines may be mentioned as examples:

3-aminobenzoic anilide,
4-aminobenzoic anilide,
4-chloro-3-aminobenzoic acid anilide, 4-chloro-3-aminobenzoic acid-3'-chloroanilide, 4-chloro-3-aminobenzoic acid-2 ', 5'-dichloroanilide, 4-chloro-3-aminobenzoic acid-2'-chloro 5'-trifluoromethylanilide, 4-chloro-3-aminobenzoic acid-3'-trifluoromethylanilide, 4-chloro-3-aminobenzceic acid-J ', 5'-bis-trifluoromethylanilide, 4-chloro-3-aminobenzoic acid-2 ¹ , 4 ', 5'-trichloranilid, 2 _i 4 ~ dichloro-3-aminobenzoic acid-2,5-dichloroanilide, 2, 4-dichloro-3-aminobenzoic acid ^3-f -trifluormethylanilid, 2,4-dichloro-3-aminobenzoic acid 3 '-chloranilide, 4-chloro-3-aminobenzoic acid-2'-methyl-3'-chloroanilide, 4-chloro-3-aminobenzoic acid-2'-methyl-5 ¹ -chloranilide, 5-amino-4-methoxy-2- chlorobenzoic acid 3'-trifluoromethylanilide, 4-methyl-3-aminobenzoic acid-2 ^f , 5'-dichloroanilide, 4-methyl-3-aminobenzoic acid 3'-trifluoromethylanilide, 4-methoxy-3-aminobenzoic acid-3'-chloroanilide, 4 -Methoxy-3-aminobenzoic acid-2 ', 5'-dichloroanilide, 4-methoxy-3-aminobenzoic acid-2', 4 ', 5'-trichloroanilide, 4-methoxy-3-aminobenzoic acid-3'-trifluoromethylanilide, 4-methoxy -3 -aminobenzoic acid-3 ^! , 5'-bis-trifluoromethylanilide, 4-methoxy-3-aminobenzoic acid-2'-chloro-5'-trifluoromethylanilide,

0098U / 0726

BAD ORfGINAL

4-Methoxy-3-aminobenzoic acid-2 ' , 5'-dimethoxy-4'-chloranilide, 4-methoxy-3-aminobenzoic acid-2', 5'-dimethyl-4'-chloroanilide, 3-amino-4-carbomethoxybenzoic acid anilide _J. 4-methoxy-3-aminobenzoic acid-α-naphthylamide _> 4-methoxy-3-aminobenzoic acid-ß-naphthylamide, 4-methoxy-3-aminobenzoic acid- (5 ' , 8'-dichloro) -a-naphthyIamide, l-aminobenzene- 4-sulfonic acid anilide,

1- ! I -4- Il (p-chloroanilide) -2- dd -4- ¹¹ (p-chloroanilide) xvbenzo] 1- dd -4- dd (o-chloroanilide) -2- dd -4- ¹¹ (2 ', 5'-dichloroanilide) L-4-sulfonic acid anilide. 1- It -4- It (p-methylanilide) -2- It -4- "(m-trifluoroanilide) H _4- It (o-methylanillide) -2,5-dichlorobenzene-4-sulfonic acid anilide _J 1- Il -4- ti (p-methoxyanilide) -2-methoxybenzene-4-sulfonic acid anilide _ί 1- Il -4- ti (o- ") -2.5- 1- Il -4- It (2 ^l , 5'-dichloroanilide) -dimetho 1- Il -4- dd (2 ', 4', 5'-trichloroanilide) 1- It -4- ti (m-trifluoromethylaniiid) 1- It -4- It (2 ¹ -chloro-5'-trifluoromethylanilide) 1- It -4- It (2 ', 4'-dimethylanilide) l-Amino-2-chlorobenzene-4-sulfonic acid anilide 1- " 1- " 1- " 1- " 1- " 1- "

0098U / 0726

154U53

l-amino-2,5-dimethoxybenzene-4-sulfonic acid (o-chloroanilide)

1- [I. -2 , 5- 1- It -2 , 5- Il -2 VJl 1- It -2 , 5- 1- It -2. , 5- 1- Il -2 .5- 1- ti -2. Ul 1- It -2, Ul 1- It ρ .5- l-l Il -2 _; Ul 1- dd -2, , 5- It -2, 1- Il -2, , 5- 1- It -2, 5- 1- It -2, 5- 1- dd ρ Ul 1- ir -2, 5- 1- It -2, 5-t 1- dd -2, 5- 1- dd -2, 5- 1- Il -2, 1- dd -2,

-4- Il (P- ") -4- H (m- ") -4- Il (2 ', 5'-dichloroanilide) _4- Il (2 ^l , 4 ', 5'-trichloro-
anilide) -4- ! I (rn-trifluoromethyl-
anilide) -4- Il (2'-chloro-5'-trifluoro-
methylanilide) -4- Il (o-methylanilide) -4- ti (p-methylanilide) -4- It (m- ") -4- It (2 ', 4'-dimethyl anllide) .4- Il (o-methoxyanilide) -4- Il methylamide _4- It dimethylamide -4- It ethylamide -4- Il dlethylamide -4- Il n-butylamide -4- Il di-n-butylamide

^^ - dimethoxybenzene ^ -sulfonic acid piperidide,

-4- " -morpholide,

^ - " -anilide,

-4- " (p-chloroanilide)

-4- "(2 ', 5'-dichloroanilide)

009814/0726

154AA53

l-Amino-2,5-diethoxybenzene-4-sulfonic acid (m-trifluoromethyl-

anilide)

1- "^ -methylbenzene ^ -sulphonic acid anilide,

1_ "-2,5-diraethyl-4-" ",

1_ "-a-methoxybenzene-S-" "*

1- · "-2-" -5- "diethylanilide,

1- "-2,4 ~ dimethoxybenzene-5-sulfonic acid anilide,

1- "^ -methylbenzene ^ -sulphonic acid anilide,

1- "^, Jl-dimethylbenzene-S-" "

1- "-naphthalene-4-sulfonic acid anilide.

The bisacetoacetyl compounds of the formula (3) to be used as coupling components contain as Arylene radical preferably one of the formula

or

where X. is a hydrogen or halogen atom, an alkyl or alkoxy group, Y is a hydrogen or halogen atom, an alkyl * or alkoxy or trifluoromethyl group and Y _{2 is} a hydrogen or halogen atom, an alkyl or alkoxy group.

0098U / 0726

BATH

These compounds are obtained in a simple manner by the action of diketene or acetoacetic ester on aromatic diamines, such as 1,4-diaminobenzene,
1 i 3-diaminobenzene,
1,3-diamino-4-methylbenzene, 1,3-diamino-4-methoxybenzene, 1,3-diamino-4-chlorobenzene, 1,4-diamino-2-chlorobenzene, 1,4-diamino-4-bronibf-naol , l-a ^ -diamino ^ -dichlov ^'1 -nzol, l, 4-diamino-2-Chloi-5-methylbenzene, 1,4-diamino-2 ~ methyl benzene, 1, 4-diamino-2,5-dimethylbenzene , l ^ -Diamino ^ -methyl-S-methoxybenzene, 1,4-diamino-2-methoxybenzene, 1,4-diamino-2,5-dimethoxybenzene, 1,4-diamino-2,5-diethoxybenzene, 1,3 -Diamino-4,6-dimethylbenzene, 1,3-diamino-2,6-dimethylbenzene, 4,4'-diaminodiphenyl, 3,3'-dichloro-4,4'-diaminodiphenyl, 3,3'-dimethyl-4 , 4'-diaminodiphenyl, 3,3'-dimethoxy-4,4'-diaminodiphenyl, 3,3 ' , 5,5'-tetrachloro-4,4'-diaminodiphenyl,

0 0 9 8 U / 0 7 2 6 ^ßAD

3,3'-dichloro-5,5'-dimethyl-4,4-diaminodiphenyl, 2,8-diaminochryses,

4,11-diaminofluoranthene,

2,6- or 1,5-diaminonaphthalene.

Coupling takes place through gradual addition

the aqueous-alkaline solution of the coupling component to the acidic solution of the diazonium salt instead. The for Solution of the coupling component to be used Alkalihydroxydmange is expediently dimensioned so that it is necessary for the neutralization of the coupling from the diazonium salt released mineral acid is sufficient. The coupling is expedient at a p n value of 3 to 6, preferably carried out between 4.5 and 5. The p "value is advantageously adjusted by adding a buffer. The salts, especially alkali salts, are used as buffers formic acid, phosphoric acid or, in particular, acetic acid. The alkaline solution of the The coupling component suitably contains a wetting agent, dispersing agent or emulsifying agent, for example an aralkyl sulfonate, such as dodecylbenzenesulfonate or the sodium salt of 1,1'-naphthylmethanesulfonic acid, polycondensation products of alkylene oxides, such as the product of the action of ethylene oxide on p-tert.-octylphenol, and also alkyl esters of sulforicinoleates, for example n-3utylsulforicinoleate. The dispersion of the coupling component

0098U / 0726 bad origin: ■ ·

- ίο -

can also advantageously contain protective colloids, for example methyl 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, dichlorobenzenes or nitrobenzene, as well as aliphatic halogenated hydrocarbons, such as, for example, hydrocarbon tetrachloride or trichlorethylene, furthermore water-miscible organic solvents such as acetone, methyl ethyl ketone, methanol, ethanol or isopropanol.

The coupling can also advantageously be carried out in such a way that an acidic solution of the diazonium salt is continuously combined with an alkaline solution of the coupling component in a mixing nozzle, the components being coupled immediately. It must be ensured that the diazo component and the coupling component are present in equimolecular amounts in the mixing nozzle, it being found to be advantageous to use a small excess of the coupling component. The easiest way to do this is to check the p "value of the liquid in the mixing nozzle, with a p" range of 4 to 4.5 being maintained with advantage . A strong turbulence between the two solutions must also be ensured in the mixing nozzle. The resulting dye dispersion is flowing through the mixing nozzle

0098U / 0726 bathroom

removed and the dye separated by filtration.

The disazo pigments obtained can be isolated by filtering off. To achieve softer grain Pigments, it is advantageous to dry the filter cake with organic solvents such as chlorobenzene, Treat xylene, ο-dichlorobenzene or nitrobenzene with heat. One arrives at the same result, if you remove the water from the moist filter cake by azeotropic distillation with one of the solvents mentioned removed.

The disazo pigments obtained are characterized by good spreadability and high color strength and can be used to color high molecular weight organic products in bulk. You are according to German Patent 1,150,165 available pigments Equal in every respect.

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

BAD ORSGiKAL 0098U / 0726

154A453

- 32 -

example 1

24.2 parts of 4-methoxy-3-aminobenzoic acid phenylamide are stirred in 200 parts of water with 30 parts of concentrated hydrochloric acid for one hour, then cooled to 0 ° and diazotized at 0 ° to 5 ° with 25 parts of 4N sodium nitrite solution. Small amounts of impurities are filtered off from the diazo solution and adjusted to a volume of 600 parts and a temperature of 0. The excess of nitrous acid present is destroyed by adding small amounts of sulfamic acid, then the solution is made crystalline by adding 30 parts. Sodium acetate _{adjusted to p u} 4.

Ii

On the other hand, 19 parts of 3,3'-dimethyl-4,4'-bis-acetoacetylaminodiphenyl are dissolved in 400 parts of water at 40 to 45 ° with 30 parts of 30 # strength sodium hydroxide solution, clarified by filtration with 0.2 part of decolorizing carbon and, after the addition of 2 Parts of n-butyl sulforicinoleate were added dropwise to the diazo solution with thorough stirring. The coupling takes about an hour and the temperature of the mixture rises to 15 to 20 ° during this time. After the end of the dropwise addition, only traces of diazo compound can be detected in the mixture, which disappear completely after brief heating to 30 to 35 °. Then heated in about one hour to 80 to 85 °, filtered hot and wash the

0098U / 0726

154U53

. Salt-free filter residue with hot water. After this Drying at 95 ° to 100 ° in vacuo gives 44.5 parts of a yellow pigment dye with a fairly hard color Texture. The pigment obtained is stirred in 800 parts of ο-dichlorobenzene and heated to 140 bis for 3 to 4 hours l45 °. After this time all coarse and hard particles have disappeared and you can see them under the microscope uniform, regular, fine yellow needles. Man lets cool to 100 °, filtered, rinsed with hot dichlorobenzene and washes the dichlorobenzene with cold Methyl alcohol. After drying, 44 parts of a loose yellow powder are obtained, which is found in plastics and paint media can be distributed well. The dyeings in PVC show very good migration and lightfastness.

If the diazo compound of this example is coupled to a fine suspension of the Bisacetoacetic arylide at 35 to 40 °, only half of the diazo compound is taken up. The second clutch cannot be forced even by increasing the temperature. The monoazo dye obtained is in contrast to the disazo pigment clearly soluble in hot nitrobenzene and can be recrystallized from this solvent. The coloring of this pigment in PVC shows insufficient migration and poor lightfastness.

009814/0726

Example 2

126 parts of 4-chloro-3-aminobenzoic acid (3'-trifluoromethylanilide) are dissolved in 50 parts of warm glacial acetic acid, while stirring in a solution of 250 parts of 30 # strength hydrochloric acid and 10 parts of the sodium salt of N-benzyl-μ-heptadecyl benzimidazole disulfonic acid in 100 parts of ice water is allowed to run in, then diazotized at 0 to 5 ° with 120 parts of 4N sodium nitrite solution and clarified by filtration.

On the other hand, 65 parts of 1,4-diacetoaoetylamino-2-chloro-5-methylbenzene are dissolved in a mixture of 230 parts of 30 # strength sodium hydroxide solution and 2000 parts of ice water. The two solutions, if necessary after dilution with water, are fed continuously to a mixing nozzle, the components being coupled immediately. By regulating the supply of the solutions, it is ensured that the p "value in the mixing nozzle is between 4.5 and 5 * 5. The temperature should be around 30 °. This setting can be regulated by adding water to the component solutions. The resulting pigment suspension is filtered off and the pilter residue is washed out; then the latter is mixed with 1,800 parts of ο-dichlorobenzene, heated to 100 ° and filtered hot. The pilter residue is first with ethylene glycol monoethyl ether and then with methanol

00981A / 0726 bad original

154U53

and water and dried in vacuo at 70 °. The dye obtained in good yield stains PVC in yellow tones of very good light and migration fastness.

In the table below, further dyes are described by coupling the diazotized Bases of column I can be obtained with the bisacetoacetic arylides of the diamines of column II. Column III there the hue of the PVC film colored with 0.2 # of these pigments at.

0098U / 0726

154U53

No Diazo component Bisacetoacetic arylide des
Diamins nuance
in PVC 1 4-chloro-3-amino-
benzoic acid-o-
methylanilide 2,5-E> ichlor-l, 4-
phenylenediamine greenish
yellow 2 dd 2-chloro-1,4-phenylene
diamine greenish
yellow 3 It 2-chloro-5-methyl-1,4
phenylenediamine neutral
yellow 4th !! 2,5-dimethyl-1,4
phenylenediamine yellow 5 ti 2-methyl-5-methoxy
phenylenediamine reddish
yellow 6th dd 2, 5-dimethoxy-l, 4-
phenylenediamine reddish
yellow 7th dd 2,5-Dlethoxy-1,4
phenylenediamine yellowish
orange 8th 4-chloro-3-amino ~
benzoic acid 3'-
chloro-2'-methyl-
anilide p-phenylenediamine greenish
yellow 9 dd 2,5-dichloro-1,4
phenylenediamine greenish
yellow 10 dd 2-chloro-5-methyl-1,4
phenylenediamine greenish
yellow 11 4-chloro-3-amino-
benzoic acid-5'-
chloro-2'-methyl-
anilide 2,5-dichloro-1,4
phenylenediamine neutral
yellow 12th dd 2,5-dimethyl-1,4
phenylenediamine reddish
yellow 13th 4-chloro-3-amino-
benzoic acid-2'-
chloro-5'-trifluoro-
methylanilide 2,5-dimethyl
1,4-phenylenediamine reddish
yellow 0098 4/0726

15Λ4Α53

•No. Diazo component Bisaoeto acetic arylide
of diamine nuance
I. 14th 4-chloro-3-amlno-
benzoic acid-2'-
chloro-5'-trifluoro-
methylanilide 4,6-chloro-1,3
phenylenediamine greenish
yellow 15th 3-amino-4-carbo-
methoxybenzoic acid
anilide 2-chloro-5-methyl-
1,4-phenylenediamine neutral
yellow 16 2,5-dimethoxy-4-
amino benzenesulfone
acid anilide Il greenish
yellow 17th dd . 2,5-dichloro-1,4
phenylenediamine greenish
yellow 18th Il 3,3'-dimethyl-4,4'-
diaminodiphenyl neutral
yellow 19th 2,5-dimethoxy-4-
aminobenzenesulfone
acid diethylamide 2,5-dichloro-1,4
phenylenediamine
■ greenish
yellow 20th l-amino-2,5-
dimethoxybenzene-4-
sulfonic anilide 1,4-phenylenediamine greenish
yellow 21 » 2-chloro-l, 4- '
phenylenediamine greenish
yellow 22nd ir 2,5-Dlchlor-l, 4-
phenylenediamine greenish
yellow 23 ti 2,5-dimethyl-1,4
phenylenediamine yellow 24 ti 2,5-dimethoxy-1,4
phenylenediamine reddish
yellow 25th It 2-methyl-5-methoxy
1,4-phenylenediamine reddish
yellow 26th ti 2,5-diethoxy-1,4
phenylenediamine reddish
yellow

noneu / 0726

15U453

No. Diazo component 0098 U Bisacetoacetic arylide
of diamine nuance 27 l-amino-2,5-
dimethoxybenzene-4-
sulfonic anilide 2,4-dichloro-1,5
phenylenediamine greenish
yellow 28 It 4,4'-diaminodiphenyl yellow 29 H 3,3'-dimethyl-4,4'-
diaminodiphenyl yellow 30th Il 3,3'-dichloro-4,4'-
diaminodiphenyl greenish
yellow 31 It 3,3'-dimethoxy-4,4 ^r -
diaminodiphenyl reddish
yellow 32 It 2,2'-dichloro-5,5'-
dimethyl-4,4'-
diaminodiphenyl greenish
yellow 33 It 1,5-diamino-naphthalene yellow 34 Il 1,4-naphthylenediamine reddish
yellow 35 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-o-chlorine-
anilide 3,3'-dimethyl-4,4'-
diaminodiphenyl yellow 36 ti 2-chloro-5-methyl-1,4-
phenylenediamine greenish
yellow 37 dd 2,5-dimethyl-1,4
phenylenediamine greenish
yellow 38 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-p-
chloranilide 3,3'-dimethyl-4,4'-
diaminodiphenyl yellow 39 It 1,4-phenylenediamine greenish
yellow 40 ti 2-chloro-5-methyl-1,4
phenylenediamine greenish
yellow / 0 7 2 6

15U453

No. Diazo component Bisacetoacetic arylide
of diamine nuance 41 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-2 ', 5'-
dichloroanilide 3,3'-dimethyl-4,4'-
diamino.diphenyl horrific
yellow 42 11 1,4-phenylenediamine greenish
yellow 43 Il 2-methyl-5-chloro-1,4
phenylenediamine greenish
yellow 44 1-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-2 ', 4', 5'-
trichloroanilide 3,3'-dimethyl-4 _J 4 ^l -
diaminodiphenyl yellow 45 11 2-chlorine-l, 4-
phenylenediamine greenish
yellow 46 I! 2-trifluoromethyl-1,4
pheny1endi amine greenish
yellow 47 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-m-
trifluoromethylanilide 3,3'-dimethyl-4,4 ^! -
diaminodiphenyl yellow 48 I! 2-methyl-5-chloro-1,4
phenylenediamine greenish j
Yellow Ί 49 I! 2,5-dimethyl-1,4
phenylenediamine green tichia
Yellow Ί 50 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-2 ¹ , 5'-
dichloro-4'-tri-
fluoromethylanilide 1,4-phenylenediamine greenish
Yellow Ι 51 II 2,5-dichloro-1,4
phenylenediamine grünstichii
yellow 52 11 2-chloro-5-methyl-1,4
phenylenediamine grünstichii
yellow

0098U / 0726

15U453

No. Diazo component Bisacetoacetic arylide
of diamine 0726 nuance 53 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-o-methyl-
anilide 2-methyl-lj 4-phenylene-
diamine greenish
yellow 54 t! 2-chloro-5-methyl-1 _J 4-
phenylenediamine greenish
yellow 55 It 2,5-dichloro-1,4
phenylenediamine greenish
yellow 56 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-2 ', V-
dimethylanilide 4,4'-diaminodiphenyl yellow 57 If 3,3 ^r -diraethyl-4,4'-
diaminodiphenyl yellow 58 t! 2-chloro-5-methyl-
1,4-phenylenediamine greenish
yellow 59 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-o-
methoxyanilide 3,3'-dimethyl-4,4'-
diaminodiphenyl yellow 60 Il 1,4-phenylenediamine greenish
yellow 61 It 2,5-DiChIOr-I ^ -
phenylenediamine greenish
yellow 62 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid-n-
butylamide 4,4'-diaminodiphenyl yellow 63 3,3'-dimethyl-4,4'-
diaminodiphenyl yellow 64 l-amino-2,5-
dimethoxybenzene-4-
sulfonic acid
dibutylamide I! yellow 0098U / ¹

BATH ORIGINAL

154U53

No I. Diazo component Bisacetoacetic arylide
of the diamond 0726 nuance 65 l-amino-2,5-dimethoxy-
benzene-4-sulfonic acid
dibutylamide 1,5-diaminonaphthalene yellow 66 l-amino-2,5-dimethoxy-
benzene-4-sulfonic acid
morpholide 3,3'-dimethyl diamino
diphenyl yellow 61 11 1,4-phenylenediamine greenish
yellow 68 dd 2-methyl-5-chloro-1,4
phenylenediamine dd dd 69 l-amino-2,5-dimethoxy-
benzene-4-sulfonic acid
piperidide 3,3'-dimethyl-4,4'-
diaminodiphenyl yellow 70 l-amino-2,5-diethoxy
4-benzenesulfonic acid
anilide 1,4-phenylenediamine yellow 71 It 4,4'-diaminodiphenyl yellow 72 l-amino-2,5-dimethyl-
benzene-4-sulfonic acid
anilide ti greenish
yellow 73 It 3,3'-dimethyl-4,4'-
diaminodiphenyl greenish
yellow 74 dd 1,4-phenylenediamine greenish
yellow 75 l-amino-2,4-dimethoxy-
benzene-5-sulfonic acid
anilide dd yellow 76 dd 4,4'-diaminodiphenyl yellow 77 dd 2-chloro-5-methyl-1,4-
phenylenediamine greenish
yellow 78 dd 2,5-dichloro-1,4
phenylenediamine greenish
yellow 79 dd 1,5-naphthylenediamine yellow 80 1-amino-2-methoxy-
benzene-5-sulfonic acid
diethyl amide Il greenish
yellow 0098U /

15U453

Diazo component bisacetoacetic arylide
of diamine

Nuarce

l-Amino-2-methoxybenzene-5-sulfonic acid diethylamide 1,4-phenylenediamine

2-chloro-1,4-phenylenediamine

2,5-dimethyl-1,4-phenylenediamine

2-chloro-5-methyl-1,4-phenylenediamine

3, y -dimethyl- * A '- diaminodiphenyl

1,5-naphthylenediamine

greenish yellow

greenish yellow

greenish yellow

greenish yellow

yellow

yellow

0098U / 0726

BAD OHiQlNAL

Claims (1)

Claims »
1. Process for the production of disazo pigments the formula . COCHt: COCH ^ R _lX I ⁵ I ³ / R ₁ (2) ^X ^ NX-BN = N-CH-CONH-A-NH-COCH-N = NB-XN C ^X R ₂ ^ \ R ₂ characterized in that a) the aqueous-alkaline solution of the bisacetoacetyl compound of the formula (3) CH COCH ₂ CONH-A-NHCOCH ₂ COCh, gradually to dissolve the diazo compound of the amine of the formula (4) ^ NX-B-NH ₅ ,
^R 2 adds, where in the given formulas A and B arylene radicals, R, and Rp hydrogen atoms, alkyl or aryl groups mean, and in which the radicals R, and Rp also together with the nitrogen atom can form a heterocyclic ring, and X is a -CO- or -SOp group, cder b) a acidic solution of the diazonium salt of the amine of the formula (4) with an alkaline solution of the coupling component of formula (3) continuously combined in a mixing nozzle, the coupling process at p. Values BAD 0RK31NAL 00981A / 0726 154U53 should run between 3 and 6. 2. The method according to claim 1, characterized in that that you can get the diazo compounds of amines of the formula wherein V is a hydrogen or halogen atom, an alkoxy or carbalkoxy group, X, Y and Z hydrogen or halogen atoms, alkyl, alkoxy, phenoxy, nitro, trifluoromethyl, Mean cyano or carbalkoxy groups are used. 3 · Process according to claims 1 and 2, characterized in that a coupling component of the formula given, in which A is a radical of the formula ? 2 Ϊ2 T2 or ^Y l means, wherein X _{2 is} a hydrogen or halogen atom, a 0098U / 0726 154U53 Alkyl or alkoxy group, Y, a hydrogen or halogen atom, an alkyl or alkoxy or trifluoromethyl group and Yp is a hydrogen or halogen atom, an alkyl or alkoxy group. 4. The method according to claims 1-3, characterized in that that the coupling is set to a p ^ value of 4-5.5 performs. 5 · Process according to claims 1 to 4, characterized in that the coupling in the presence of a Buffer. 6. The method according to claims 1 to 5, characterized in that the coupling is carried out in the presence of a dispersant. 7. The method according to claims 1 to 6, characterized in that the disazo pigments obtained treated with an organic solvent before drying. BATHROOM OFTIQINAL 0098U / 0726