CS207800B2 - Method of preparation of the reactive dyes - Google Patents

Abstract

The invention relates to novel reactive dyes of the formula <IMAGE> wherein the phenyl radical A may be substituted by C1-4-alkyl, C1-4-alkoxy, halogen, nitro, carboxyl and sulpho, and Z is an optionally substituted amino group. They are suitable for dyeing and printing materials such as silk, leather and wool, and especially for dyeing and printing cellulose-containing materials.

Description

The invention. - refers to - reactive dyes - of formula I,

wherein - the phenyl moiety - A may be - substituted with - methyl, - methoxy, chlorine, carboxy - and - sulfo - and

Z - is - NH2 -, - C1 -C6 alkylamino, - optionally substituted by chlorine, - cyano, - hydroxy, alkoxy - having 1 to 4 carbon atoms, carboxy, sulfo or sulfate, N N-dialkylamino having 1 to 6 carbon atoms in each alkyl, optionally substituted by hydroxy, benzylamino, phenethylamino, cyclohexylamino, N-alkyl-N-phenylamino having 1 to 2 carbon atoms in the alkyl group, N-sulfomethyl-N-phenylamino, phenylamino optionally substituted with 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen atom, nitro group, hydroxy group, acetylamino group, ureido group, carbamoyl group, sulfamoyl group, trifluoromethyl group, sulfonyl group, sulfonyl group, sulfonyl group, sulfonyl group , naphthylamino, optionally substituted by hydroxy, sulfo or nitro, furylamino, thiophenylamino, pyrazolylamine others, pyridylamino, pyrimidylamino, quinolylamino, benzimidazolylamino, benzthiazolylamino, benzoxazolylamino, morpholino, piperidino or piperazino.

The bridging member "NH", which connects the benzoyl moiety with the aminofluoro-s-triazine moiety, is bonded in the meta-position or para-position to the "CO" group.

Examples of amino groups Z in formula I include:

-NH2, methylamiriogroup, ...... ......

ethylamino, propylamino, isopropylamino, butylamino, hexylamino, β-methoxyethylamino, χ-methoxypropylamino, β-ethoxyethylamino, NN-dimethylamino, · ......

N, N-diethylamino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, p-chloroethylamino, ε-cyanethylamino, γ-cyanopropyl, mini, β-carboxyethylaminoO, sulfomethylamino, β-sulfo , N, N < 3 &gt; -hydroxyethylamino, [omega] -hydroxypropylamino, benzylamino, cyclohexylamino, morpholino, piperidino, plperazino, and in particular aromatic amino groups such as phenylamino, toluidino, xylidino, fentinoidino, cenetino, cenetino,

2-, '3- and' 4-s. Sulfoan linogroup,

2.5- disulfxanilinoxy _J sulfomethylanilino, N-sulfomethylanilino,

3- and 4-carbxxdfenylamino group,

2-kaxbox5-5-sulfophepalamo,

2-carboxy-4-sulfophenylamino,

4-sulfox-1,1-naphlylamine oxy group,

3.6-disulfo-1-naphthyloxy group,

3,6,8-trisulfo-1-paftdlamiphogroups · · у ..........

У, 6 _; 8-thiazol-1-ylphthlylamino.

Advantageous . they are in particular reactive dyes of the formula II

Wm

wherein Z is as defined above.

Preferred are reactive dyes of formula (II) wherein Z is -NHy, C1-4 alkyl, N, N-dialkyl of 1 to 4 carbon atoms in each of the alkyls, thypolymino groups, NN-diethanolamine groups , β-sulfoethoxylamine, phenylamino optionally substituted by chlorine, methyl, methyl, ethoxy, carboxy, sulfo, acetylamino, ureido and hydroxy, pyphtylamiposyl, N optionally substituted sulfo, N-substituted-N, N-phenylamino or morpholino.

· Preferred are in particular reactive dyes of the formula II wherein Z is a group fendlamipχ ^ι, · optionally substituted by chloro, methyl, methyl-oxyl etboxylem, karboxdskuρinxu and sulfo.

Particularly valuable reactive dyes of this preferred group of dyes are the reactive dyes of formulas III, IV and XIII.

Λ

NH-c-C-NH

I »

NN ^S C ^Z i

SA ₃ H (XIII)

The process for the preparation of the reactive dyes of the formula I is characterized in that the coupling component of the formula V is reacted together in any order.

wherein A is as defined above, the ^{diazocomponent of} formula VI is ^σ - ₂ co

(VI)

2,4,6-trifluoro-s-triazine VII and an amine VIII

H-Z, (VIII) wherein Z is as defined above.

The reactive dyes of formula II can be prepared by reacting a coupling component of the formula in any order

IX

Ί

ОН

(X) a diazotized diazo component of formula X

2,4,6-trifluoro-s-triazine of formula VII and amine of formula VIII.

A preferred embodiment is characterized in that the amine of formula (VIII) is ammonia, (C1-C4) alkylamine, (C1-C4) N-dialkylamine in each of the alkyls, ethanolamine, Ν, di-diethanolamine, taurine, phenylamine optionally substituted with chloro, methyl, methoxy, ethoxy, carboxy, sulfo, acetylamino, ureido and hydroxy, naphthylamine, optionally substituted with sulfo, N-methyl-N-phenylamine, N-ethyl-N-phenylamine or morpholine.

In particular, the amine of the formula VIII used is a phenylamine optionally substituted by chlorine, methyl, methoxy, ethoxy, carboxy and sulfo.

Since the individual reaction steps mentioned above, namely diazotization, coupling and condensation, can be carried out in different order, possibly also partially simultaneously, different process variants are possible. The starting materials used for each partial reaction are derived from formula I. Usually, the reaction is carried out in a stepwise sequence, the order of the individual reactions among the individual reaction components of formulas V, VI, VII and VIII being freely selectable.

Important process variants are characterized by:

1} The coupling component of formula V is coupled with a diazotized diazo component of formula VI, the obtained monoazo compound is condensed with 2,4,6-trifluoro-s-triazine of formula VII and the primary condensation product is condensed with an amine of formula VIII.

The last two reaction steps may also be carried out in reverse order, whereby 2,4,6-trifluoro-s-triazine is first condensed with an amine of formula VIIIa. The primary condensation product obtained is condensed with the above monoazo compound.

2) The diazocomponent of formula VI is condensed with 2,4,6-trifluoro-s-triazine of formula VII, the primary condensation product is condensed with the amine of formula VIII, the secondary condensation product obtained is diazotized and coupled to the coupling component of formula V.

Also in this process variant, the condensation with an amine of the formula VIII can be carried out as the last reaction step as mentioned under 1).

A preferred method for preparing a reactive dye of formula III is characterized in that diazotized 1-amino-4-acetylaminobenzene-2-sulfonic acid and coupled with 1-hydroxy-7-phenylaminonaphthalene-3,6-disulfonic acid, the acetyl group is cleaved by saponification, the resulting intermediate of formula XI

is condensed with cyanurfluoride and the obtained primary condensation product is condensed with o-toluidine.

A preferred method for preparing a reactive dye of formula IV is characterized by diazotizing 1-amino-4-acetylaminobenzene-2-sulfonic acid and coupling it with 1-hydroxy-7- (3'-sulfophenylamino) naphthalene-3-sulfonic acid, the acetyl group is cleaved by saponification, the resulting intermediate of formula XII

is condensed with cyanurfluoride and the obtained primary condensation product is condensed with o-toluidine.

A preferred process for preparing a reactive dye of the formula XIII is characterized in that it comprises:

4-a: minotoluene-3-sulfonic acid condenses with cyanurfluoride, the primary condensation product is condensed with p-phenylenediamine sulfonic acid, the resulting intermediate of formula XIV is diazotized and coupled with 1-hydroxy-7- (3'-sulfophenylamine-o) - naphthalene-3-sulfonic acid.

The starting compounds for the preparation of the reactive dyes of the formula I are, for example, the following compounds:

a] coupling components of the formula V 1-Hydroxy-7-phenylamino-phthalene-3-sulfonic acid, 1-hydroxy-7-aenylamino-moniteite-3,6-disulfonic acid, 1-hydroxy-7- (3'-sulfen-phenylamino) - naphthalene-3-sulfonic acid, 1-hydroxy-7- (4'-sulfophenylamino) -naphthalene-4-sulfonic acid, 1-hydroxy-7- (4'-carbonyloxyphenylamino) -naphthalene-α-sulfonic acid, 1-hyd trans-7- (4'-Methylphenylamino) -naphthalene-3,6-disulfonic acid, 1-hydroxy-7 '- [4'-methoxyphenylamino) -naphthalene-3,6-disulfonic acid.

b) diazo components of formula VI

1,4-diaminobenzene-2-sulfonic acid, N-diaminobenzene-2-disulfonic acid,

1,4-diaminobenzene-2,6-diisulfonic acid.

In many cases, it is expedient not to use diaminobenzenesulfonic acid alone as a diazocomposite, but instead amine-acylamine-banzansulfonic acid, for example 4-acetylaminolin-2-sulfonic acid, from which, after coupling, the acetyl group is cleaved by saponification before being saponified. In addition, a nitroamino compound, for example 4-nitroamino-2-sulfonic acid, can also be used as the diazo component of formula VI, and after coupling, the nitro group is reduced to the amino group by treatment with sodium sulfide or sodium hydrate. Diazocomponents of formula VI containing 3‘- or 4‘-aminobenzoylamino can be prepared by acylation of diaminobenzanesulfonic acid with 3‘- or 4‘-nitrobenzoyl halide, for example 4-nitrobenzone chloride, and then reduction of the nitro group to the amino group. Other diabetic VI formulas are:

1-Amino-4-acetylaminobenzane-2-sulfonic acid (saponification), 1-amino-4-nitrobenzene-2-sulphonic acid [reduction], 1-amino-4- (4'-aminobenznylamino) -benzene-2,5 1-amino-4- (4'-nitrobenzoylamino) -benzene-4-sulfonic acid (reduction), -disulfonic acid, 1-amino-4- (3'-aminobenzoylamino) -benzene = 5-amino-4-sulfonic acid

1-Amino-4- (3'-nitro-benzoylamino) -benzene-2-sulfonic acid (reduction).

c) 2,4,6-trifluoro-s-triazine of formula VII (cyanurofluoride)

(d) amines of Formula VIII ammonia, methylamine, dimethylamine, ethylamine, diethylamine, propylamine, isopropylamine, butylamine, dibutylamine, isobutylamine, sec-butylamine, tert-butylamine, hexylamine, methoxyxyethylamine, ethylene amine, quinine amine, methylene amine, methylamine, ^ι methylamine, hndroxyprnpnlamin, aminoethanesulfonic acid, ^and the LS-J- látoethylamin, benzylamine, cnklnhaxylamin, aniline, o-, m- and p-toluidine, 2,3-, 2,4-, 2,5-, 2,6- 3,4- and 3,5-dimethnlanine, o-, m- and p-chloroaniline, N-methylaniline, N-ethylaniline,

3- or 4-acetylaminoaniline, o-, m- and p-nitroaniline, o-, m- and p-min-o-oenol,

2-Methyl-4-nitroaniline

2-Ethyl-5-nitroanone,

2,5-dimthoxy aniline,

3-Methyl-4-nitroaniline

2-nitro-4-methylaniline,

3-nitro-4-methylanene, o-, m- and β-anisidine, o-, m- and β-lenetidine,

2-mlthoxy-5-mlthianin,

2-Athoxine-5-methoxyaniline

4-bromoaniline,

3-aminobenzamine,

4-aminnphenylsullamide,

3-tri-luormlthaian,

3- and 4-aminophenyl urea,

1- diesel laminate,

2-naphthylamine, 2-amino-1-hydroxynaphthalene, 1-amino-4-hydroxynaphthalene, 1-amino-8-hydroxynaphthalene, 1-amino-2-hydroxynaphthalene, 1-amino-7-hydroxynaphthalene, orthanilic acid, methanoic acid , sulfanilic acid, aniline-2,4-disulfonic acid, aniline-2,5-disulfonic acid, aniline-3,5-disulfonic acid, anthranilic acid, m- and p-aminobenzoic acid,

4-aminophenylmethanesulfonic acid, aniline-N-methanesulfonic acid, 2-aminotoluene-4-sulfonic acid, 2-aminoitoluene-5-sulfonic acid, p-aminosalicylic acid, 1-amino-4-carboxybenzene-3-sulfonic acid, / 1-amino-2-carbonylbenzene-5-sulfonic acid, 1-amino-5-carbonylbenzene-2-sulfonic acid,

1-naphthylamine-2-, -3-, -4-, -5-, -6-, -7- and -8-

-sulfonic acid,

2-naphthylamine-1-, -3-, -4-, -5-, -6-, -7- and -8-

-sulfonic acid,

1-naphthylamine-2,4-, -2,5-, -2,7-, -2,8-, -3,5-,

-3,6-, -3,7-, -3,8-, -4,6-, -4,7-, -4,8- and -5,8-disulfonic acid,

2-naphthylamine-1,5-, -1,6-, -1,7-, -3,6-, -3,7-,

-4,7-, -4,8-, -5,7- and -6,8-disulfonic acid

1-naphthylamine-2,4,6-, -2,4,7-, -2,5,7-, -3,5,7-,

-3,6,8- and -4,6,8-trisulfonic acid,

2-naphthylamine-1,3,7-, -1,5,7-, -3, 5,7-, -3,6,7-,

-3,6,8- and -4,6,8-trisulfonic acid,

2-, 3- and 4-aminopyridine, 2-aminobenzthiazole,

5-, 6- and 8-aminoquinoline, 2-aminopyrimidine, morpholine, piperidine and piperazine.

Diaziation of diazincents is - usually - carried out by treatment with nitrous acid in an aqueous solution containing mineral - acid at a lower temperature, coupling - with coupling - components is carried out at a slightly acidic, neutral to slightly alkaline pH.

The condensation of 2,4,6-rifluoro-s-triazine of formula VII and diazo components of formula - VI and self-compounds of formula VIII - is preferably carried out in an aqueous solution or suspension at a lower temperature and at a slightly acidic, neutral to slightly alkaline pH. The process according to claim 1, wherein at least one fluorine atom remains in the finished reactive dye of formula I as a leaving group. Preferably, the hydrogen fluoride released during the condensation is continuously neutralized by the addition of an aqueous solution of an alkali hydroxide, carbonate or bicarbonate.

The reactive dyes of the formula I can be isolated and processed into useful dry dye preparations. The isolation is preferably carried out at the lowest possible temperature by salting out and filtration. Optionally, the filtered dye may be dried by the addition of cuvées and / or buffering agents, for example by adding a mixture of equal parts of primary and secondary sodium phosphate. Preferably, the drying is carried out at a temperature which is not too high and at a reduced pressure. In certain cases, the - dry - dye - preparations - can be prepared directly - by spray drying - whole. mixtures - formed - in the preparation of the dye, i.e. without intermediate-dye.

The dyes - of the general formula I - are reactive with the fibers, since they contain a cleavable in the s-triazine residue. fluorine atom.

S-fiber reactive compounds are those compounds which can react with the - hydroxy groups - of cellulose or with the amino groups of natural fibers. or synthetic polyamides to form a covalent chemical bond.

The reactive dyes of the general formula I are novel. They are characterized by high reactivity and provide - coloring - with good - stability to moisture and light. In particular, it is noteworthy that these dyes have good solubility and electrolytic solubility at good dye withdrawal and high fixation properties, and that unfixed dye fractions can be easily removed. - Coloring is etchable.

The reactive dyes of the formula I are suitable for - dyeing and printing a wide variety of materials, such as silk, - leather, wool, superpolyamide fibers and superpolyurethanes, in particular for dyeing cellulose-containing fibrous materials such as flax, cellulose, regenerated -cellulose - and, above all, cotton. They are also suitable for dyeing by drawing but also for flaring, whereby the material is impregnated with an aqueous and - optionally salt-containing dye solution - and the dye is treated after alkaline treatment or in the presence of alkali, - optionally - -heat fixes.

The dyes are also suitable for printing, in particular on cotton, but also for printing nitrogen-containing fibers, for example, wool, silk or blended fabrics containing wool.

It is recommended - dyeing - and - prints - thoroughly - - rinsing - with cold and hot water, possibly with the addition of dispersing agents and agents, which facilitate diffusion of the non-fixed proportions - dyes.

In the following examples, the preparation of monoazo intermediates is not described in all cases, but can be carried out without further explanation from the above description.

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

Example 1

To the ice-cooled neutral solution 5.94 parts of the dye of formula XII

in 200 parts of water, a solution of 1.0 part of cyanurfluoride in 3 parts of toluene was added dropwise over 5 minutes while the pH of the reaction mixture was maintained between 6 and 7, while 1 N sodium hydroxide solution was added dropwise. of o-toluidine, warmed to 30-35 ° C and the pH of the solution was maintained between 7 and 8 by dropwise addition of 1 N sodium hydroxide solution. After completion of the reaction, the aminofluorotriazine dye was salted out by adding 5% by volume sodium chloride and filtered. The dye paste was thoroughly mixed with a saturated aqueous solution of 1 part secondary sodium phosphate and dried under vacuum at 40-50 ° C.

The dye thus obtained dyes cotton to reddish-brown shades.

If equivalent amounts of the amines listed below are used instead of o-toluidine, similar dyes are obtained.

Example Amines ammonia methylamine ethanolamine diethanolamine with cyanuric chloride and o-toluidine according to the data in Example 1 gives a dye which dyes cotton to violet-brown shades.

Example 28

Example taurine

Amines n-butylamine aniline

N-methylaniline N-ethylaniline m-toluidine p-toluidine m-chloroaniline p-chloroaniline o-anisidine p-aniisidine p-phenetidine p-aminobenzoic acid aniline-3-sulfonic acid

4-aminoacetanilide

3-aminophenyl urea

4-aminophenylurea diethylamine morphelin 2-naphthylamine-6-sulfonic acid

4-Aminosalicylic acid

Example 27

Reaction of 5.94 parts of dye XI

with cyanuric chloride and o-toluidine according to the data in Example 1, a dye is obtained which dyes the cotton to brown shades.

Starting from an isomer of formula

Reaction of 6.74 parts of dye of formula

Sat ₃ h

a similar dye is obtained.

Example 29

To an ice-cooled solution of 19.35 parts of 4- (4'-aminobenzoylamino) -1-amino-207800 benzene-2,5-disulfonic acid in 300 parts of water was added dropwise a solution of 5.0 parts of cyanurfluoride in 7 parts of toluene over 5-10 minutes and The pH of the reaction mixture was maintained between 6 and 7 by concurrent dropwise addition of 1 N sodium hydroxide solution. After complete acylation of the amino group, the solution of the primary condensation product was mixed with a neutral solution of 8.65 parts · methanilic acid in 30 parts water. The pH of the monofluorotriazine compound is cooled to 0-5 [deg.] And diazotized by the addition of 25 parts of 2 N sodium nitrite solution and 15 parts of 10 N hydrochloric acid. The diazo compound thus obtained is added to a neutral solution of 19.75 parts of 1-hydroxy-7-phenylaminonaphthalene-3,6-disulfonic acid in 200 parts of water to which 33 parts of sodium bicarbonate are added prior to coupling.

The resulting dye is salted out with 10% by volume sodium chloride. and filtered. After mixing with a concentrated aqueous solution of 2 parts of secondary sodium phosphate, the dye paste is dried at 45 ° C.

The dye thus obtained dyes cotton to brown shades.

When 1-hydroxy-7- (3 '- $ иИоТепу1атто) naphthalene-3 • sullonic acid is used as the coupling component, a similar dye is obtained.

Example 30

To an ice-cooled, neutral solution of 26.8 parts of 1,4-phenylenedio-mm-2,5-disulfonic acid in 300 parts of water, 14 parts of cyanuric chloride are added dropwise over 10 minutes, with simultaneous addition. 2 N sodium hydroxide solution maintains pH at 6 to 6.5. To the difluorotriazine compound is then added a neutral solution of 18 parts of methanilic acid in 60 parts of water, the temperature of the reaction mixture is allowed to rise to room temperature and the pH is maintained at 6.5 to 7 with 2N sodium hydroxide solution.

The reaction mixture was ice-cooled to 0 ° C and diazoitized with 35 parts of 10 N hydrochloric acid and 25 parts of 4 N. sodium nitrite solution. Coupling with 39.5 parts of 1-hydroxy-7- (3 &apos; -sulfenylene lamino) -naphthalene-3-sulfonic acid in the presence of sodium bicarbonate yields a dye which, upon isolation, dyes cotton to brown shades.

Example 31

To an ice-cooled neutral solution of 18.72 parts of 4-aminotoluene-3-uulonic acid in 300 parts of water, 10 parts of cyanurfluoride are added dropwise over 10 minutes while maintaining a pH of between 6 and 7 by simultaneous addition of 1 N sodium hydroxide solution.

The clear primary condensation product solution is then added to the ice-cooled neutral solution for about 10 minutes

1β

18.8 parts of p-phenylenediaminosulfonic acid in 150 parts of water and simultaneously dropwise addition of 1 N sodium hydroxide solution maintain the pH between 6 and 7.

After the condensation is complete, the solution obtained is mixed with 100 parts ice, 25 parts 4 N. sodium nitrite solution and 25 parts of 10 N hydrochloric acid. The diazo compound thus obtained is poured into a neutral suspension of 39.5 parts of m-sulphophenyl-γ-acid in 200 parts of water, to which 40 parts of sodium bicarbonate are added before coupling.

After coupling, the dye is salted out with 10% by volume sodium chloride and filtered. The dye paste is well mixed with the saturated paste. solution of 5 parts of secondary sodium phosphate and dried under vacuum at 40 to 50 degrees C.

The dye thus obtained dyes cotton to brown shades.

Example 32

To an ice-cooled neutral solution of 8.65 parts of ortanilic acid in 200 parts of water, 5 parts of cyanurfluoride are added dropwise over 10 minutes, while 1N solution is added simultaneously. The sodium condensation product thus obtained is poured onto an ice-cooled neutral suspension of 15.35 parts of 1-amino-4- (3'-amino-benzoylamino) -benzene-2-sulfonic acid in 100 parts. The pH of the second condensation is maintained at 7 to 8 by dropwise addition of water and 1N sodium hydroxide solution dropwise. Diazotization is then carried out by adding 50 parts of ice, 12.5 parts of 4 N sodium nitrite solution and 12.5 parts of 10 N hydrochloric acid. The diazo compound obtained is poured into a neutral suspension of 19.75 parts of m-sulfophenyl-γ-acid in 100 parts of water, to which 10 parts of sodium bicarbonate are added before coupling.

After coupling, the precipitated dye is filtered off, well mixed with a saturated aqueous solution of 2.5 parts of secondary sodium phosphate and dried under vacuum at 40-50 ° C.

The dye obtained dyes cotton to brown shades.

Dyeing Procedure I parts of the dye prepared according to Example 1 were dissolved in 100 parts of water with the addition of 0.5 parts of sodium m-nitrobenzenilonate. The obtained solution is impregnated with a cotton fabric by taking up 75% of its weight and then drying.

The fabric is then impregnated with a 20 ° C warm solution containing 5 g of sodium hydroxide and 300 g of sodium chloride per liter, squeezed to 75% weight gain and steamed at 100 to 101 ° C for 30 seconds, rinsed , soap for 1/4 hour in a 0.3% boiling solution of non-ionic detergent, rinse and dry.

The prescription for dyeing parts of the dye prepared according to Example 1 were dissolved in ~ 100 parts of water. The solution was added to 1900 parts cold water and 60 parts sodium chloride was added. 100 parts of cotton fabric were added to this dye bath.

The temperature is raised to 40 DEG C. and after 30 minutes 40 parts of soda ash and 60 parts of sodium chloride are added. The temperature is maintained at 40 ° C for 30 minutes, rinsed and the dye is soaped for 15 minutes in a 0.3% boiling solution of non-ionic detergent, rinsed and dried.

Claims (6)

Process for preparing reactive dyes. of formula (I) wherein the phenyl moiety A may be substituted with methyl, methoxy, chloro, carboxy, and sulfo; and Z is -NH 2, C 1 -C 6 alkylamino, optionally substituted with chlorine, cyano, hydroxy, C 1 -C 4 alkoxy, carboxy, sulfo, or sulfate, N, N-idialkylamino of 1 to 6 carbon atoms in each alkyl, optionally substituted with hydroxy, benzylamino, phenethylamino, cyclohexylamino, N-alkyl-N-phenylamino, C 1 -C 2 alkyl, N-sulfomethyl-N-phenylamino, phenylamino optionally substituted with C 1 -C 4 alkyl carbon, C 1 -C 4 alkoxy, halogen, nitro, hydroxy, acetylamino, urido, carbamoyl, sulfamoyl, trifluoromethyl, carboxy, sulfo and sulfomethyl, naphthylamino, optionally substituted hydroxy, nitro, thio, sulfo, thio, ,. pyridylamino pyrimjdylaminóskupína, chinolylaminoskupina, benzimidazolylaminoskupina, benzthiazolylaml · noskuoina, bez.oxazolylammGskupina, mortolinoskupina, piperidiioskupina or OLP ^e razinoskupina, wherein together in any order, let react the coupling component of the formula V wherein A is as defined above ... diazotovaná diazokomponenta. of formula VI, (VI) H 2,4,6-trifluoro-s-triazine of formula VII and amine of formula VIII. 2. A process according to claim 1, wherein the copol is reacted in any order with a coupling component of formula IX, (IX) a diazotized diazo component of formula X, (R) -Riazine of formula (VII) and an amine of formula (VII); Hz I 'II IN F, (VII) (VIII) where Z is as defined above. 3. A process according to claim 2, wherein the amine of formula (VIII) is ammonia, (C1-C4) alkylamine, (C1-C4) alkylamino (C1-C4) alkylamine; alkyl, ethanolamine, N, N-diethanolamine, taurine, phenylamine, optionally substituted with chloro, methyl, methoxy, ethoxy, carboxy, sulfo, acetylamino, ureido or hydroxy, naphthylamine, optionally substituted with sulfo, N-methyl, N-ethyl-N-phenylamine or morpholine. A process according to claim 3 for the preparation of a reactive dye of formula III, characterized in that 1-amino-4-acetylaminobenzene-2-sulfonic acid is diazotized and coupled with 1-hydroxy-7-phenylaminonaphthalene-3,6-disulfonic acid, acetyl After saponification, the resulting intermediate of formula XI is condensed with cyanurfluoride and the obtained primary condensation product is condensed with o-toluidine. 5. A process according to claim 3 for the preparation of a reactive dye of formula IV, characterized in that 1-amino-4-acetylaminobenzene-2-sulfonic acid is diazotized and coupled with 1-hydroxy-7- (3'-sulfophenylamino) -naphthalene-3. -sulfonic acid, the acetyl group is cleaved by saponification, the resulting intermediate of formula XII is condensed with cyanurfluoride and the resulting 6. The method of item 3 for preparing a repressive condensation product. The compound of formula XIII is reacted with o-toluidine. characterized in that 4-aminotoluene-3-sulfonic acid is condensed with cyanurfluoride, the primary condensation product is condensed with p-phenylenediamine sulfonic acid, the resulting intermediate of formula XIV is diazotized and coupled with 1-hydroxy-7- (3'-sulfophenylamino) 1-Naphthalene-3-sulfonic acid.