DE1419883A1 - Process for the preparation of water-soluble reactive disazo dyes - Google Patents

Description

Basel (Switzerland) gases 1292 / A

Process for the preparation of water-soluble reactive Di.ga.zo = dyes.

The present invention relates to a process for the preparation of metallizable reactive disazo dyes of the formula ^x

yH _x -HNR ₂ -NN - / AY (l)

and their chromium or cobalt complex compounds, in which R is a radical of the benzene, diphenyl or naphthalene series , R _{2 is} a radical of the benzene or naphthalene series which is coupled twice in ortho-position to hydroxy and / or optionally monosubstituted amino groups, χ one to the Substituents that enable metal complex formation,

a £ hydrogen or at least a remainder of the Porael

Shark
-NC-, where Hai is chlorine or bromine

Group and the ",

other y_ one at least one radical of the formula -N «C-, in which Hai

stands for chlorine or bromine, containing groups mean * and in which R ₁ , R ₂ and the nucleus A together the number of solubilizing groups necessary for water solubility and optionally

BAD contain further substituents.

809803/0228

® :? » '>: a \ v J', fer · rt? · 11 U ^ gq « ^; nausii dyes ai'fe btri? te.hfc
in, the «um * 1? ά k« 7.ί .- ^ bI ^ r H-aihenfoXge I ifol de.?> £ ·? .asove ^ bond from eln & nj aromatic Λ'ηί, η dsr Be ng ι ,. '· -, oiphönyl- or
Naphthalinreih® and 1 MoI der- tU &KovsrfrirKhmg; from üin & sR in orthoi; filling to the Ainirxog ^ app " sin * to ^ etallkcsiplKX training enabling"

«Xitaaltep.den und gftg'iJ3'Tiit ^li jafa.Us wa :. tBi'sub l with 1 W ^ I iiiie ^ aRai kupp hmfc i'ähi gs tBllnW'X zu HfdTi ^ ij; - \ sa; i / or3rr »^ ■ ^^ • χ ^ ϋϊΐ.ι n Aiiiinogrupp» in e; .vl ·:;! &. "!. fcen:? * Napbfchalirai'eih® kupp« ". i; ^ t * <iid den? - ,: 'iie., t; i.-n« \ i, d · .-! · .Iiind ^ stÄiiS ei: ip τ <ι <· ₃ wähi'ej. '. Cl, missdastenä

cu-t * benzene

implementation

^ rx remainder of the formula

Ha.l

Hal fir chlorine "or bromine rt ^ ht d: te" ur WasserlUsll ^ hk ^ äv, necessary "Αιγαία of the groups must contain, wfti-.u-erAd odw after the structure in substance odsj * after the structure awf <? Sv fiber ; nlt ^ in ^ m ohromotier kob & i ^ donating means fc

One can proceed in such a way that ν, αιι I Hol ύ & τ öia "r: - / ürbitidur» g aua an arcane animal

^y l " ^R l

where R dia the above meaning b * s.lts? t, and χ, hydrogen or a hydroxy ούνν In

809803/0228

, together

0RK3INAL

U19883

üi * erfühx'bai ^: i> n substituents or one directly or via -Ο-, -S-, -KK- or -N- (optionally substituted

Alkyl) bonded group, which at least one radical

Hai of the formula _M contains I, where Hai stands for OhIor or

Bromine stands, mean

with 1 mole of a monoazo which may contain chromium or cobalt connection of the formula

c.

- H «N- (AJ CHI)

clutch,

wherein χ, R ₂ and A have the meanings given above and y_2 is hydrogen or a hydroxyl or thiol group, a

into an optionally monosubstituted amino group transferable substituents or a-directly via -0-, -S-, -NH- or -N- (optionally substituted alkyl) bonded, at least

Shark a radical of the formula "1, in which Hai stands for chlorine or bromine

stands, containing group means,

where at least one of the radicals χ. or y_ ₂ must be different from hydrogen, and the disazo dyes obtained which must contain at least the number of solubilizing groups necessary for water solubility, if v ^ .and / or ^ g for a hydroxyl or thiol group or a substituent which can be converted into an optionally monosubstituted amino group stands, optionally after conversion of the substituent or substituents £, < and / or y_ _{P is converted} into an amino group, with a compound, &

Hal

which contains at least two radicals of the formula _M |, in which

Hai means chlorine or bromine during or after building in

Substance or treated with a chromium or cobalt releasing agent after the build-up on the paser.

But you can also proceed in such a way that one mole of the diazo compound from an aminobenzene of the formula

where x, y ~ and A have the meanings given above, with 1 mole of a monoazo compound of the formula

y _x - R ₁ - N - N - R ₂ - H

clutch,

wherein ^ ₁ , R ₁ and R _{2 have} the meanings given above,

and the disazo dyes obtained of at least those for water solubility must contain the necessary number of solubilizing groups, treated further in the manner just described.

The metallic reactive dyes obtainable by both embodiments of the process or their cobalt or chromium complex compounds correspond to formula (I) in the metal-free state. The substituents that the radicals A, R ₁ and R_ ^ may contain by definition are the sulfonic acid group,

=> an optionally substituted alkylsulfonyl group and a ο

sulfonic acid amide group optionally substituted on the nitrogen atom (Amide, methylamide, ethylamide, dimethylamide, diethylamide,

2-Hydroxyäthylaraid, Di- {2-hydroxyäthyl) -amid, 2- or 3-Hydroxypropylamid, 3-Methoxypropylamid, 3- or 4-Methoxybutylamid, 2-Aethoxyäthylamld, Phenylamid, 2-, 3- or ^ -Methyl -, - Methoxy-, Ethoxy or chlorophenylamide, N-methyl-N-phenylamide, N-2-hydroxyethyl-N-phenylamide, behzylamide, cyclohexylamide) or also: Halogen atoms (chlorine, bromine atoms), lower alkyl or alkoxy groups (methyl, methoxy, ethoxy), nitro groups and acylamino groups (acetyl, propionyl, benzoyl, carbomethoxy, carbethoxyamino groups). ·

Hai As compounds which contain at least two radicals of the formula -N »C- contain, in which Hai means chlorine or bromine, come e.g. in Consider the heterocyclic compounds listed below, tetrameric chlorine or bromoyane, cyanuric chloride, cyanuric bromide, primary condensation products of a cyanuric halide the composition

Hal- C C-z I η N N

Hal where Hal is chlorine or bromine,

and ζ the optionally further substituted radical of a primary or secondary aliphatic, alicyclic, aromatic or heterocyclic amine, an aliphatic, alicyclic, aromatic or heterocyclic hydroxy or thiol compound, but in particular the radical of aniline, its alkyl and sulfonic acid or carboxylic acid derivatives, of lower

809803/0228

- 6 -Mono- and PiaIkylarainen sow! «Then mean the remainder of ammonia,

also 2,4,6-friohlorpyriraidin and a ^ ö and their derivatives, which carry, for example, the following substituents in the 5-position Methyl, ethyl, optionally substituted on the nitrogen atom

Carboxylic acid or sulfonic acid amides Carboxylic acid methyl or ethyl Chlorvinyi,

ester, acyl, e.g. benzoyl, alkenyl, e.g. allyl, »substituted alkyl, e.g. 2-ketopropyl, carboxymethyl, chloro- or Bromomethyl as well as a methylene group between two pyrimidine nuclei, 2,4,5,6-tetrachloro- or -Tetrabromopyrimidine, 2,6-Diehlor- or -dibromopyriinidine-4-carboxylic acid ethyl ester, 2,4,5-trichloropyrimidine, which may be substituted on the nitrogen atom 4- or 5-carboxamide or * »sulfonic acid amide derivatives of 2,6-dichloro- or dibromopyrimidine, 2,5,6-trichloro-4-methylpyrimidine, S ^ -Dichlor-S-chloromethyl-o-methylpyrimldine and 2,6-dichloro-4-trlcblormethylpyrimldin.

The introduction of a cyanide residue is best done in aqueous Medium at about 0 ° C and in the case of a weakly acidic reaction, e.g. at pH values between j5 and 5 The cyanuric halide is used as such in solid form or in an organic Solvent dissolved, e.g. in acetone. For the primary condensation products of a cyanuric halide, nan chooses one best Temperature from 30 ° to 60 ° C and a pH value from 4 to 6, while, for the di-, TrI- and tetrahalopyrimidines temperatures

between 40 ° and 100 «c most suitable» Ind.

BAD ORiGlNAL <

809803/0228

With regard to the water vapor volatility of individual halopyrimidines, it is advisable to work in vessels which may be equipped with a reflux condenser. The reaction is conducted in such a way that only one halogen atom reacts with an exchangeable hydrogen atom. The reaction is carried out in a weakly alkaline, neutral to weakly acidic medium, but preferably within the pH range from 9 to 3. To neutralize the one equivalent of hydrogen halide that is formed, either an acid-binding agent, such as sodium acetate, is added to the reaction solution at the beginning, or sodium or potassium carbonate or potassium carbonate in solid, powdered form or as a concentrated aqueous solution is added in small portions during the reaction. Aqueous solutions of sodium or potassium hydroxide are also suitable as neutralizing agents. "The addition of small amounts of a wetting agent or emulsifier to the reaction mixture can accelerate the reaction. The coupling of the diazo compounds from the amines of the formulas XI and XV with the azo components is carried out in an acidic, neutral or alkaline medium at temperatures of 0 ° - 30 ° C .

The conversion of the monoazo compounds or the disazo dyes into their chromium or cobalt complex compounds is advantageous in aqueous solution or in an organic medium, for example in formamide, or in the concentrated aqueous solution an alkali metal salt of a low molecular weight aliphatic monocarboxylic acid. You leave it on with advantage

80980 3/0228

B -

two molecules of monoazo compound or disazo dye one less than 2, but at least one atom of metal containing amount of one act as a metal donor.

Suitable compounds of chromium are e.g. Chromifluorld, Chrotnisulfat, Chromiformiatp Chromiacetat, potassium chromisulfate or Ammonium chromisulfate. The chromates, e.g. sodium or Kaliumchroraat or »bich ^ omat, are suitable in excellent catfish for metallization.

It is advantageous to work in a strongly alkaline medium, with optionally reducing substances can be added.

Cobalt formate, cobaltoacetate, for example, serve as cobalt compounds and cobalt sulphate. Will the metallization in the concentrated made aqueous solution of an alkali metal salt of a low molecular weight aliphatic monocarboxylic acid, water-insoluble metal compounds can also be used, for example Cobalt hydroxide and cobalt carbonate.

The metallization in aqueous or is particularly advantageous carried out alkaline medium, the metal compounds are added in the presence of those compounds which the metals in Keep a complex bond in a caustic alkaline medium, such as tartaric acid, citric acid and lactic acid.

BATH ORIGINAL 809803/0223

The metal complex compounds obtained are optionally after pouring the organic metallization solutions into brine, deposited from an aqueous medium by adding salt, then filtered off, optionally washed and then dried,

The metal-containing azo dyes obtained are uniform metal complex compounds in which essentially one atom of metal is bonded to two molecules of disazo dye. The metal complex compounds are so-called Is2 complexes, in which one molecule Disazo dye with about 0.3-0.7 atoms of metal is linked.

The new reactive dyes containing chromium or cobalt are suitable for padding or printing wool, silk, leather, synthetic polyamide fibers and fibers made from natural or regenerated cellulose in brown tones.

The obtained, optionally an alkaline Mach treatment Padding and prints that are subjected to elevated temperatures and subsequently soaped have good light, khifa, washing,

Walk, sweat, rubbing and alkali fastness properties.

free dyes are obtained padding and printing Metallized fibers and then have very good light and wet * authenticity.

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

809803/0228

example 1

22.4 parts of S-amino - ^ - chloro-1-hyäroxybenzol-ö-sulfonic acid become stirred in 90 parts of water with 15 parts of 30 # strength hydrochloric acid and at 0-5 ° with a solution of 7 parts of sodium nitrite in 25 parts Water diazotized. The diazo suspension is left at one temperature from 0-5 ° su a solution of 11 parts of 1,3-dihydroxybenzene and 22 parts of sodium carbonate in 100 parts of water fHessen. To After three hours of stirring, the coupling is complete. The dye is completely precipitated by adding sodium chloride, then filtered off and washed with sodium chloride solution.

The filter cake is suspended in 150 parts of water at 70 °. A solution of 16 parts of cobalt sulfate in 40 parts of water is added dropwise at 70-75 ° over the course of half an hour. A dilute sodium carbonate solution is added dropwise at the same time to keep the pH between 5.0 and 6.0. After the cobalt sulfate solution has been added, the solution is stirred for a further 1 hour at 70 °. The cobalt complex compound is precipitated by adding sodium chloride, then filtered off and washed with sodium chloride solution. 36.8 parts of l-amino-3- [2 ^β , 5 ^β 6 »-trichloropyrimidyl-i ^ ·) -amino-] benzene-6-sulfonic acid are dissolved in 320 parts of water at 60 °. 25 parts of 30% hydrochloric acid are added to the solution, which has been cooled to 5 ° by the addition of bis, and a solution of 7 parts of sodium nitrite in 25 parts of water is then added over the course of 30 minutes. The diazo suspension obtained is used to dissolve the cobalt complex compound described above in

809803/0228

300 parts of water were added over the course of 15 minutes at a temperature of 0-5 °. The pH of the coupling compound is kept at 8.0-8.5 by sprinkling in sodium carbonate. After three hours of stirring, the coupling has ended. The cobalt complex of the disazo dye is completely precipitated by adding sodium chloride, then filtered off and washed with sodium chloride solution. The dye, dried in a vacuum, is a dark powder that you! ' dissolves in water with dvinice! brown paint. Mercerized Baumwoilsatin ι is printed with the printing paste of the following composition fciner

30 parts of the dye obtained as described above

100 parts of urea, 372 parts of water, 450 parts of its 3-strength sodium hydroxide bond 15 parts of sodium 1-nitrobenzene-3-sulfonic acid 33 parts of sodium carbonate

1000 parts

The dried textile material is at 102-104 for 10-15 minutes steamed and then rinsed cold and warm. After the boiling Soaps followed by renewed rinsing and drying give a brown print of good wet and light fastness.

> Example 2

b ©

23.4 parts of 2-amino-4-nitro-1-hydroxybenzene-6-sulfonic acid are in g

80 parts of water mixed with 15 parts of 30 # hydrochloric acid and §

at 0-5 ° with a solution of 7 parts of sodium nitrite in 25 parts

Water dlazotiert. The diazo solution is made Congo-neutral with sodium carbonate and then added at a temperature of 0-5 ° to a solution of 22 parts of 1,3-dihydroxybenzene and kk parts of sodium carbonate in 200 parts of water. The coupling is complete after stirring. The dye is completely precipitated by adding sodium chloride, then filtered off and washed with sodium chloride solution until no more 1,3-dihydroxybenzene can be detected in the filtrate.

The filter cake is stirred in 200 parts of water at 90 °. 30 parts of crystallized sodium acetate and 30 parts of crystallized chromium potassium sulfate are added to the dye suspension, and this mixture is refluxed for 12 hours. The chromium complex compound is precipitated by adding sodium chloride, then filtered off and washed with sodium chloride solution 39.2 parts of 1-amino-3- [2 ¹ .5 ^ ö'-trichloropyriraidyl- ( ¹ M) -amino-] benzene-6-sulfonic acid sodium are dissolved in 320 parts of water. 25 parts of 3O strength hydrochloric acid are added to the solution, which has been cooled to 5 ° by the addition of ice, and then a solution of 7 parts of sodium nitrite in 25 parts of water over the course of 30 minutes. The resulting diazo suspension is added to the solution of the above-described chromium complex compound in 400 parts of water over the course of 15 minutes at a temperature of 0-5 °. By sprinkling in sodium carbonate, the pH of the coupling is kept at 8.0-8.5. After stirring for one hour, the coupling is complete. By adding sodium chloride, the chromium complex compound of the disazo color

809803/0228

Etoffee completely precipitated, then filtered off and washed with sodium chloride solution. The dye, dried in vacuo, provides a dark powder that * dissolves in water with dark brown Color dissolves.

BaurawolJsretonne is printed with a printing paste of the following composition:

30 parts of the dye obtained according to the above information,

100 parts urea,

372 parts of water '. .

Λ50 parts of a 3 # sodium alginate thickener. 15 parts of sodium l-nitrobenzene-3-sulfonic acid 33 parts sodium carbonate ...

1000 parts.

The dried textile material is at 102-104 ° for 10-15 minutes steamed and then peeled cold and warm. After the boiling Soaps with subsequent rinsing and drying are obtained a reddish brown print of good wet and light skin.

B e 1 β ρ le I 3 39.2 part l-amino-3-

BenzoX-6-sulfonic acid N & trium are in 320 parts fc & aeer of 60 ° reports. 25

Part 30% hydrochloric acid and then a solution within 30 minutes

/ on 7 Tsilen sodium nitrate in 25 parts of water. 2u of this suspension

8P9803 / 0228

thalin-T-a slurry of 24 parts of 2-amino-5 ^ droxyjftaphj - ^^^

Suifonsfture in 200 parts of water and adjusts the pH of the Coupling mass by adding sodium acetate solution to 3 * 5 After stirring for twelve hours at a temperature of 10, the Clutch finished. By adding sodium chloride, the coloring » substance completely precipitated, then filtered off and washed with sodium chloride solution.

The filter cake is stirred in 350 parts of water and washed through Addition of sodium carbonate adjusted to a pH of 8.5. A diazo solution prepared according to Example 2 is left in addition from 23 * 4 parts of 2-amino-4-nitro-1-hydroxybenzene-6-eulCone acid add dropwise, the pH of the couplings »βse by adding Sodium carbonate solution is maintained at 8.5-9.0. After stirring for twelve hours, the disazo dye is acidified with Hydrochloric acid precipitated> filtered and washed with sodium chloride solution ", The filter cake is suspended in 400 parts of water at 70 ° and a pH of 5.0. Within half an hour you leave at 70-75 ° tine solution of 16 parts of cobalt sulfate in 40 parts Add water dropwise. By simultaneous dropwise addition of a diluted Sodium carbonate ItJβUTg the pH is kept between 5.0 and 6.0. After adding the cobalt sulphate solution, 1 hour at Stirred at 70 °. The ifoba it complex connection is part by adding Sodium chloride precipitated, then filtered off and washed old sodium chlorite solution. The dyestuff, dried in vacuo, ceases dark powder, which in water is dark brown in color, solves. /> ·

Spun rayon nArd with a printing paste of the following composition printed:

30 parts of the dye obtained according to the above information,

200 parts of urea

272 parts of water

450 parts of a typical sodium alginate thickener 15 parts of hydrobenzene-3-3ulphonic acid sodium

33 parts of sodium carbonate

1000 parts.

The dried textile is for 1 minute be.L 200 ° or Exposed to dry heat for 10 hours at 120 °. Connect; it is rinsed hot and cold and soaped at the boil. Wake up again Rinsing and drying gives a brown print of good wet and light fastness.

Example ¹ !

A neutral solution of 23 parts of 3-acetylamlnobenzoi-6-sulfonic acid in 200 parts of water and 13 parts of 3% sodium hydroxide solution is mixed with a solution of 7 parts of oat cream nitrite in 25 parts of water and takes 30 minutes at 0-5 ° to 25 parts of 30 # hydrochloric acid and 100 parts of ice water were added dropwise. This dlazo suspension is added at 5 ° to a suspension of 3 * 1.1 parts

809803/0228

of the monoazo dyes obtained according to the information in the first paragraph of Example 2 in 2030 parts of water, the pH of the coupling substance being kept at 8.5 ~ 9 * 0 by adding sodium carbonate. After eight hours of stirring at 5-10 ° the coupling is complete. The disazo dye is completely precipitated by adding sodium chloride, then filtered off and divided with Matrlucsehloridlöfmng, the filter cake is divided into 400 parts :? 5; iigön Na1; riuffihydroxyülösung praised for 1 hour at 15 ° , Dureh Siugabo of sodium chloride wire dt.

The cow cows wix * d in 400 '!' Rushing water outpandiorc and na ^ h kobaitiert and oiled according to the information provided by Beiopiels 1.

The cobalt complex compound thus obtained is dissolved in 300 parts of water and treated with 18.3 parts of cyanuric chloride at a temperature of 0 °. The pH of the reaction mixture is kept at between 3.0 and 4.0 by dropwise addition of a dilute sodium carbonate solution. After stirring for three hours at 0 °, the condensation is ended. The dye is precipitated and a'ofilted by adding sodium chloride. The dye, dried in a vacuum, is a dark powder that dissolves in water with a brown color. For Vigoureux printing, the cotton is printed with a printing paste of the following composition:

809803/0228

30 great uco dye obtained according to the above information, 200 parts urea, 565 parts water,

200 parts of 3 # 3g sodium alginate thickener 5 parts of a highly sulfonated castor oil

1000 parts.

The steaming time is twice 45 minutes with intermediate cooling.

BATH ORIGINAL 809803/0228

The following table contains additional chromium or cobalt-containing reactive dyes, which according to the information available to the _co Examples 1 to 4 Bind.

(j) Kr. diazo component 1 coupling component diazo component 2 reactive system metal

IO

* O

1,3-diamlnobenzene 6-sulfonic acid

do. do.

do. do.

do. do.

do.

1,3-dihydroxybenzene

do.

do.

do.

2-Amino-1-hydroxy-2,4,5,6-tetrabenzene-4-sulfonchlorpyrlmldln acid

2-amino-4-chloro-1-hydroxybenzene-6-sulfonic acid

benzene-4-sulfonic acid

2,4,6-trichloropyrimidine

do.

2-Amlno-6-nitro-1- 2,4,5,6-Tetra hydroxybenzene-4-chloropyrlmldln sulfonic acid

do.

do.

Cr

Cr

Co

Ccr

Cr

nuance

rotstleh brown

red tint: brown

do. 2 = amino = 6 = nitro-l-
hydroxybenzene ° 4-
sulfonic acid do. Cr do. do. do. do. Co do. do. 2 = amino-4-nitro-
l ~ eulfonic acid-6- do. Co do. do. 2-amino-1-hydroxy
benzene-4,6-disulfone
acid Cyanuric chloride Co
0 / £ 08,608. do.

CO OO OO

"r. Diasoicomponents

1 , 3 ~ Dlaininoben2ol β-gsulionic acid

"So,

20th

ixaph1ifc &

ao.

do,

do,

Coupling component «! Diazo component 2 reactive system metal Nuanes

σο.

do.

do.

do,

ao.

ao,

do.

ZO:

Amino-1-hydroxysol'-4 , ό-disul-

2,4,6-Tribromopyrlmidln

chlorpyrimidln

ao.

S-ÄKino-I-hydroxybensol ^ -sulfon-

do.

"" Amino-I-hydroxy-2,4-Bi <
h ^ tnzol "^» iäwlf onsSure {5? * -hydroxy) -

äthyjLamlno-l, 3 »5 ·

-hydroxyboniiol-ö-

do.

S-Asnino-S-chloro-
1 ° hy rir o: c; ^f b sr.z ο 1 - **

do.

Size Red Brown Or rotβfei Brown Go brew:?. Brown

- · Cr

2,4,6-trichloro
pyritaidin

Co

bromopyrimidine
do.

£ = v ml r ο ~ '? · - · Λ.! ^ λ *
"hy dr o ;; yb onso
sulfonic acid

üthy lamino-1, .3 * 5-ti ⁱ iazin.-2 ■ -eulfon sSure-

pyrirnidine

rotati brown

brown do.

brown cr do.

"lVNiowo ave

No.

24

Diazo component 1 coupling component diazo component 2 reactive «system metal Nuancs

Γ: 7

28

2,6 -Diamino-naph
thalin-4,8-disul
fonic acid

do.

ύο.

diphenyl-3
acid

do.

do.

do.
ύο.

do,

1,3-dihydroxybenzene

do.

do. do.

do.

do"

ac.

dti,

2-amino-4-nitro-

l ~ hydroxybenzene-6

sulfonic acid

2- amino-6-nlt ro-1-hydroxybenzene-4

do.

2 ~ amino-1-hydroxy

benzene «-4,6-dlsul-

fonic acid

00.

2-amino «4-chior-

l-hydroxybenzene-6-

sulfonic acid

S-amino ^ S-chlorine
1-hydroxybenzene
4-sulfonic acid

do.

2,4,5,6-tetra
chlorpyrimidln Co Brown 1VN19IÜ0 ava Cyanuric bromide Co Brown 2,4,6-trichloro Cr rotisU
Brown

2,4-chloro-6-Co

carboxymethylamlno-1,3,5-

trlaain

2,4 * "dichloro-6-Cr phenylamino-1,3,5-trialn-3 ¹ -sulfonic acid

2,4-dichloro-5-chloromethyl-6-methylpyrlmidine

Cyanuric chloride Go

S, 4-DIbPOm-O-Co

phonylatalno-1.3 * 5 * "
triasin * 4 ^J -sulf on acid

2,4-Dichior-O-Cr

phenylamino-1,3 * 5-triazine-2 " -carboxylic acid

Brown

rotsti brown

Brown

red s ti

8220 / ε08608

No. Diazo component 1 Coupling component Diazo component

reactive system metal nuance

4.4 ^a diamino-1, I ^s - 1,3-Bihydroxyberiaol

dlphenyl-3-sulfone

acid

do.

do.

do.

do.

do.

2-Amlno-4-nltro-

l-hydroxybenzene-6

sulfonic acid 2,5,6-trichloro-Cr 4-methylpyrlmldln

do. 2,4,6-trichloro Co pyrlmldln 2 ~ Aralno-6-nitro- l- = hydroxybenzene-4- do. Co sulfonic acid do. Cyanuric chloride Cr

su'i folic acid

38 1-aminobenzenesulfons £ urs

39 1,3 -BiaaiiKO likewiseI -

do.

do. 2,6-DiamondIno ~ l "hy °
aroxybenaol-ii -
sul sulfonic acid

do. 2i4,5,6-tetrachloro-Cr pyrlmldln

do.

do.

UO.

äo Co

1-amino »3-hydroxy-
benzene 2-amino-l-hydroxy
benzene-4-sulfone
acid 2,4-chloro-b-di-
(ß-hydroxySthyl) -
amlno-1,3,5-trlazln Co do. 2.4 "6-Trlchlor-
pyrlmidln _: Cr do. 1-hydroxybenzene-6-
Sulfonic acid 2,4,5,0-Te'cra-
brompyrlmidln Oo do. do. do. Cr άο. 2-Amlno-4-chloro-l- do. Cr fonic acid

brown do.

rcristJ

No. diazo component

1,3-Dlamlnobenzene 6-sulfonic acid

do.

do. do. do. do. do. do. do.

Coupling component t Diazo component 2 responsive system metal Nuanc 1-amino-3-hydroxy
benzene 1,3-diamino benzene 2-amino-l-hydroxy
benzene-4-sulfoh-
acid-N-3-methoxy-
propylamide 2,4,5-trichloro
pyrimidine Cr. rotst
Brown do.- do. do. 2,4-chloro-6-N-
methyl-N-ethyl- • Co do. do. triazine-2 * -sul-
fons & ure do. 2-amino-4-nltro-l-
hydroxybenzene-6-
eulfonic acid _ 2 * ^ * 5 » 6-tetrachlor
pyrimldin - Cr Brown do. 2-Aralno-6-nitro-
l-hydroxybenzene-4-
sulfonic acid do. Cr do. 2-amino-5-hydroxy
naphthalene-7-8ul-
fonic acid 2-amino-4-chloro
1-hydroxybenzene-6-
sulfonic cure Cyanuric chloride - Cr do. do. 2-amino-6-chloro
1-hydroxybenzene
4-sulfonic acid 2,4,5,6-tetra
bromopyrimidln Cr do. 2-amino-1-hydroxy
benzene-4-sulfone
acid 2,4,6-trichloro
pyrimldin Cr do. S-amino ^ -nltro-l-
hydroxybenzene-6-
sulfonic acid do. Cr
cc viole
Sting
Brown 2-amino-6-nitro-
1-hydroxybenzene-4- 2,4,5,6-tetra-
ohlorpyrlmidln -Co rotst
Brown

sulfonic acid

No. diazo component 1 coupling component diazo component 2 reactive system metal nuance

53

55

57

58

59

1,3-Dlaminobenzene 6-sulfonic acid

do.

2-Araino-5-hydroxynaphthalln-7-By?. -fonic acid

do.

1,4-Dlaminobenzene-1,3-dihydroxybenzene 2-sulfonic acid

1,3-diamlnobenzene 6-sulfonic acid

do.

do.

3-amino-l- (hydroxy methyl) benzene

do.

do.

do.

do.

2-amino-4-chloro-l-
hydroxybenzene-6-
sulfonic acid 2, ^, 5,6-tetrachloro
pyrimidine Co rotstlch
Brown 2-AmInO-O-ChIor-
l-hydroxybenzene-4-
sulfonic acid 2,4,6-trichloropy-
rlmldin Co do. 2-amlno-4-chloro-
1-hydroxybenzene-6-
sulfonic acid 2,4,6-trichloropy-
rimidin Co Brown 2-Amlno-6-acetyl-
amlno-1-hydroxy-
benzene-4-sulfonic & ure do. Co do;

2-amino-6-methyl l-hydroxybenzene-4 sulfonic acid

do.

2-amino-1-hydroxybenzene-4,6-disulfonic acid

2,4,5,6-tetrachloro-copyrlraldine

2,4-dichloro-5-chloromethyl-6-methylpyrimldine

2,4,6-irlchlorpyrimldln

Co

Co

Claims (1)

Claim Process for the preparation of "water-soluble, reactive disazo dyes, characterized in that one in any Sequence 1 mole of the diazo compound from an aromatic Amine of the benzene, diphenyl or naphthalene series and 1 mole of the diazo compound from a group in the ortho position to the amino group which enables metal complex formation containing and optionally further substituted aminobenzene with 1 mole of two coupling-free carbon atoms in the ortho position to hydroxy and / or optionally monosubstituted amino groups containing azo component of Benzene or naphthalene series, and the obtained disazo Dye containing at least one before, during or after the Shark Settlement introduced, at least one residue of the formula -N «* C ~, wherein Hal is chlorine or bromine, containing group and must contain at least the number of solubilizing groups necessary for water solubility, during or after the build-up Treated in substance or after the build-up on the Paser with a chromium or cobalt releasing agent. The patent attorney: 809803/0228