CH633309A5 - Reactive dyes, their preparation and use - Google Patents

Description

The invention relates to reactive dyes of the form

(S03H) 0-1

—N = N - <7 ^ J) —NH CO ° 3H (SOjH) ^

\

11 - NIU

* N \

c c-z

• o-l N N

1

F

(1)

wherein the phenyl radical A can be substituted by Ci_4-alkyl, Ci_4-alkoxy, halogen, nitro, carboxy and sulfo, and Z is an optionally substituted amino group.

Possible substituents on the phenyl radical A are: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, fluorine, chlorine, bromine, nitro, carboxy and sulfo.

The -NH bridge member, which connects the benzoyl residue with the amino-fluoro-s-triazine residue, is bound to the -CO group in the meta or para position.

Suitable amino groups Z are: -NH2, alkylamino, N, N-dialkylamino, cycloalkylamino, N, N-dicyclo-alkylamino, aralkylamino, arylamino groups, mixed substituted amino groups, such as N-alkyl-N- cyclohexylamino and N-alkyl-N-arylamino groups, furthermore amino groups which contain heterocyclic radicals which may have further fused-on carbocyclic rings, and amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring which optionally contains further heteroatoms .

The alkyl radicals mentioned above can be straight-chain or branched, low molecular weight or higher molecular weight; alkyl radicals having 1 to 6 carbon atoms are preferred; cyclohexyl, aralkyl and aryl radicals are in particular cyclohexyl, benzyl, phenethyl, phenyl and naphthyl radicals; heterocyclic residues are especially furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole residues; and as amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring, preference is given to residues of six-membered N-heterocyclic compounds which may contain nitrogen, oxygen and sulfur as further heteroatoms. > 5 The above-mentioned alkyl, cycloalkyl, aralkyl and aryl radicals, the heterocyclic radicals and the N-heterocyclic rings can be further substituted, for. B. by: halogen, such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C ^ alkyl, C ^ alkoxy, acylamino groups such as 20 acetylamino, amino groups such as -NH2, methylamino and ethylamino, ureido , Hydroxy, carboxy, sulfomethyl and sulfo.

Examples of the amino radical Z in formula (1) are: -NH2, methylamino, ethylamino, propylamino, isopropylamino, butylamino, hexylamino, β-methoxyethylamino, 25 y-methoxypropylamino, β-ethoxyethylamino, N, N-dimethyl- amino, N, N-diethylamino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, ß-chloroethylamino, ß-cyanoethylamino, y-cyano-propylamino, ß-carboxyethylamino, sulfomethylamino, ß-sul-foäthylamino, ß-hydroethylamino, N, N-di-ß-hydroethyl-30 amino, γ-hydroxypropylamino, benzylamino, cyclohexyla-mino, morpholino, piperidino, piperazino, and especially aromatic amino groups such as phenylamino, toluidino, xylidino, chloroanilino, Anisidino, phenetidino, 2-, 3- and 4-sulfoanilino, 2,5-disulfoanilino, sulfomethylanilino, N-sulfomethylani-35 lino, 3- and 4-carboxyphenylamino, 2-carboxy-5-sulfophenyla-mino, 2- Carboxy-4-sulfophenylamino, 4-sulfonaphthyl- (l) -amino, 3,6-disulfonaphthyl- (l) -amino, 3,6,8-trisulfonaphthyl- (l) -amino and 4,6,8-trisulfonaphthyl- (l) -amino.

Reactive dyes of the formula (1) in which the phenyl radical A can be substituted by carboxy or sulfo and Z is as defined under formula (1) are preferred.

Reactive dyes of the formula are particularly preferred

CO

(SO3I1),

<S ° 3H> 0-1

(2)

wherein Z is an optionally substituted amino group. nylamino, N-ethyl-N-phenylamino or morpholino.

Preferred are reactive dyes of the formula (2), in which Z 55 Preferred are in particular reactive dyes of the formula -NH2, Ci-4-alkylamino, N, N-Di-C1.4-alkylamino, ethanolamino, (2), in which Z is phenylamino, through chlorine, methyl, methoxy,

N, N-diethanolamino, β-sulfoethylamino, phenylamino, which can be substituted for ethoxy, carboxy and sulfo.

by chlorine, methyl, methoxy, ethoxy, carboxy, sulfo, acety- Valuable representatives of this preferred class are the lamino, ureido and hydroxy can be substituted, naphthyl reactive dyes of the formulas amino, which can be substituted by sulfo, N-methyl-N -phe- 60

N = N-M-NH-C SO-, H / N

^ C '

I.

F

s "NH ^ P

CH3

(3)

5

633309

and n = n

° 3n S03H

c c

I II

n n rn-f)

3rd

(4)

The process for the preparation of reactive dyes of the formula (1) is characterized in that a coupling component of the formula h2n \ j_v "nh" (^ o3H) 1_2

20th

(5)

(so3h) 0.

a diazotized diazo component of the formula

H2N - \ L / _NH C0

(s03h) 1_2

2,4,6-trifluoro-s-triazine of the formula

* nn f - c c - f i M

n n ^ C /

and an amine of the formula

H-Z

implemented with each other in any order.

A coupling component of the formula (5) is preferably used, in which the phenyl radical A can be substituted by carboxy or sulfo. 55

The reactive dyes of the formula (2) are prepared by using a coupling component of the formula nh

(fo h) so3h

(3H) 0-1 (S / 03H) 0_1 is a diazotized diazo component of the formula

2,4,6-trifluoro-s-triazine of the formula (7) and an amine of the formula (8) are reacted with one another in any order.

A preferred embodiment is characterized in that the amine of the formula (8) is ammonia, C] .4-25 alkylamine, N, N-di-Ci_4-alkylamine, ethanolamine, N, N-diethanolamine, taurine, phenylamine, which can be substituted by chlorine, methyl, methoxy, ethoxy, carboxy, sulfo, acetylamino, ureido and hydroxy, naphthylamine which can be substituted by sulfo, N-methyl-N-phenylamine, N-ethyl-N-phe-30 nylamine or morpholine used.

In particular, the amine of the formula (8) used is phenylamine, which can be substituted by chlorine, methyl, methoxy, ethoxy, carboxy and sulfo.

Since the individual above-mentioned process steps, namely diazotization, coupling and condensation, can be carried out in different (6) different order, possibly partially also simultaneously, different process variants are possible. The starting materials to be used for each partial reaction result from formula (1). In general, the reaction is carried out step by step, the order of the simple reactions between the (7) individual reaction components of the formulas (5), (6), (7) and (8) being freely selectable.

The most important process variants are characterized by the fact that one

1. Coupling a coupling component of the formula (5) with a dia-zotiert diazo component of the formula (6), the resulting monoazo compound with 2,4,6-trifluoro-s-triazine of the formula (7) condensed and the primary condensation product with

(8) 50 an amine of formula (8) condensed.

The last two reaction steps can also be carried out in reverse order by first condensing the 2,4,6-trifluoro-s-triazine with an amine of the formula (8) and condensing the primary condensation product obtained with the above-mentioned monoazo compound.

2. a diazo component of the formula (6) is condensed with 2,4,6-trifluoro-s-triazine of the formula (7), the primary condensation product is condensed with an amine of the formula (8), the secondary condensation product obtained is diazotized and on a

60 coupling component of formula (5) couples.

In this production variant too, the condensation with the amine of the formula (8) can be carried out as under 1 as the last reaction step.

The preferred mode of preparation of reactive dye 65 of formula (3) is characterized in that 1,4-diaminobenzene-2-sulfonic acid is diazotized and coupled to l-hydroxy-7-phenylamino-naphthalene-3,6-disulfonic acid, the resulting intermediate compound of the formula

(9)

1

633309

6

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

The preferred method of preparing the reactive dye of the formula (4) is characterized in that 1,4-diamino

(11)

nobenzol-2-sulfonic acid diazo and coupled to l-hydroxy-7- (3'-sulfo-phenylamino) -naphthalene-3-sulfonic acid, the resulting intermediate compound of the formula

(12)

condensed with cyanuric fluoride and the resulting primary condensation product was condensed with o-toluidine.

The following may be mentioned as starting compounds for the preparation of the reactive dyes of the formula (1):

25th

30th

a) Coupling components of the formula (5) l-hydroxy-7-phenylamino-naphthalene-3-sulfonic acid, l-hydroxy-7-phenylamino-naphthalene-3,6-disulfonic acid, l-hydroxy-7- (3'-sulfophenylamino) -naphthalene-3-sulfonic acid, 1 -hydroxy-7- (4 '-sulfophenylamino) -naphthalene-3-sulfonic acid, l-hydroxy-7- (4'-carboxyphenylamino) -naphthalene-3-sulfonic acid, 1 -hydroxy -7- (4'-methylphenylamino) -naphthalene-3,6-disulfonic acid, l-hydroxy-7- (4'-methoxyphenylamino) -naphthalene-3,6-disulfonic acid.

35

b) diazo components of the formula (6)

1,4-diaminobenzene-2-sulfonic acid, 1,4-diaminobenzene-2,5-disulfonic acid, 1,4-diaminobenzene-2,6-disulfonic acid; in some cases it is advantageous not to use diaminobenzenesulfonic acid itself as the diazo component, but instead to use an amino-acylamino-benzenesulfonic acid, e.g. B. the 4-acetyl-amino-aniline-2-sulfonic acid, from which, after coupling, the acetyl group is split off by saponification before condensing further. Furthermore, as a diazo component of the formula (6), a nitroamino compound, e.g. B. 45 4-nitro-aniline-2-sulfonic acid, use and reduce the nitro group after coupling with sodium sulfate or sodium sulfate to the amino group. The diazo components of formula (6) which contain a 4'-aminobenzoylamino group are prepared by acylation of a diaminobenzene-50 sulfonic acid with a 4'-amino (or nitro) benzoyl halide, e.g. B. 4-nitro-benzoyl chloride, and optionally, subsequent reduction of the nitro group to the amino group. Further diazo components of the formula (6): l-amino-4-acetylamino-benzene-2-sulfonic acid (saponified), l-amino-4-nitrobenzene-2-sulfonic acid 55 (reduced), l-amino-4- ( 4'-aminobenzoylamino) benzene

2,5-disulfonic acid, l-amino-4- (3'-aminobenzoylamino) -benzoI-2,5-disulfonic acid, l-amino-4- (4'-nitrobenzoylamino) -benzene-2-sulfonic acid (reduced), l-amino -4- (3'-nitrobenzoylamino) -benzene-2-sulfonic acid (reduced). 60

c) 2,4,6-trifluoro-s-triazine of the formula (7) (cyanuric fluoride)

d) amines of the formula (8)

Ammonia, methylamine, dimethylamine, ethylamine, diethylamine, propylamine, isopropylamine, butylamine, dibutylamine, iso-65-butylamine, sec-butylamine, tert-butylamine, hexylamine, methoxyethylamine, ethoxyethylamine, methoxypropylamine, chloroethylamine, hydroxyamine , Dihydroxyethylamine, hydroxy

propylamine, aminoethanesulfonic acid, ß-sulfatoethylamine, benzylamine, cyclohexylamine, aniline, o-, m- and p-toluidine, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- and 3,5-dimethylaniline, o-, m- and p-chloroaniline, N-methylaniline, N-ethylaniline, 3- or 4-acetylaminoaniline, o-, m- and p-nitroaniline, o-, m- and p- Aminophenol, 2-methyl-4-nitroaniline, 2-methyl-5-nitroaniline, 2,5-dimethoxyaniline, 3-methyl-4-nitroaniline, 2-nitro-4-methylaniline, 3-nitro-4-methylaniline, o- , m- and p-anisidine, o-, m- and p-phenetidine, 2-methoxy-5-methylaniline, 2-ethoxy-5-methoxyaniline, 4-bromoaniline, 3-amino-benzamine, 4-aminophenylsulfamide, 3-trifluoromethylaniline, 3-and 4-aminophenylurea, 1-naphthylamine, 2-naphthylamine, 2-amino-l-hydroxy-naphthalene, l-amino4-hydroxy-naphthalene, l-amino-8-hydroxy-naphthalene , l-amino-2-hydroxy-naphthalene, l-amino-7-hydroxy-naphthalene, orthanilic acid, metanilic 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 acid, 4-aminophenylmethanesulfonic acid, ani-lin-N-methanesulfonic acid, 2-aminotoluene4-sulfonic acid, 2-aminotoluene-5-sulfonic acid, p-aminosalicylic acid, l-amino-4-car-boxy-benzene-3-sulfonic acid, l-amino-2-carboxy-benzene-5-sulfonic acid, l-amino-5-carboxy-benzene-2-sulfonic acid, 1-naphthyla-min-2-, -3-, -4-, -5- , -6-, -7- and -8-sulfonic acid, 2-naphthylamine-l-, -3-, -4-, -5-, -6-, -7- and -8-sulfonic acid, l-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-l, 5-, -1,6-, -1,7-, -3,6- , -3,7-, 4,7 - 4,8-, -5,7-and -6,8-disulfonic acid, l-naphthylamine-2,4,6-, -2,4,7-, -2 , 5,7-, -3,5,7-, -3,6,8- and 4,6,8-trisulfonic acid, 2-naphthylamine-l, 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-aminobenzothiazole, 5-, 6- and 8-aminoquinoline, 2-aminopyrimidine, morpholine, piperidine and piperazine.

The diazotization of the diazo components is generally carried out by the action of nitrous acid in aqueous-mineral-acid solution at low temperature, and the coupling to the coupling components at weakly acidic, neutral to weakly alkaline pH values.

The condensation of the 2,4,6-trifluoro-s-triazine of the formula (7) with the diazo components of the formula (6) and the amino compounds of the formula (8) are preferably carried out in aqueous solution or suspension, at low temperature and at weakly acidic, neutral to weakly alkaline pH, so that at least one fluorine atom remains as a removable residue in the finished reactive dye of the formula (1). The hydrogen fluoride liberated during the condensation is advantageously continuously neutralized by adding aqueous alkali metal hydroxides, carbonates or bicarbonates.

The reactive dyes of the formula (1) can be isolated and processed into usable, dry dyeing preparations. The isolation is preferably carried out at the lowest possible temperatures by salting out and filtering. The filtered

7

633309

Dyes can optionally after adding coupage agents and / or buffering agents, eg. B. after adding a mixture of equal parts of mono- and disodium phosphate; drying is preferably carried out at temperatures which are not too high and under reduced pressure. 5 In certain cases, the dry preparations according to the invention can be dried directly by atomization drying of the entire preparation mixture, ie. H. Manufacture without intermediate insulation of the dyes.

The dyes of the formula (1) are fiber-reactive since they contain a releasable fluorine atom in the io s-triazine radical.

Fiber-reactive compounds are to be understood as those which are able to react with the hydroxyl groups of cellulose or with the amino groups of natural or synthetic polyamides with the formation of covalent chemical bonds.

The reactive dyes of formula (1) are new. They are characterized by high reactivity and they result in dyeings with good wet and light fastness. It should be particularly emphasized that the dyes have good solubility and electrolyte solubility with good extraction properties and high dye fixation, and that the non-fixed portions can be removed easily. The colors are etchable.

The reactive dyes of the formula (1) are suitable for dyeing and printing a wide variety of materials, such as silk, leather, wool, superpolyamide fibers and superpolyamide urethanes, but in particular fibrous materials containing cellulose

Structure such as linen, cellulose, regenerated cellulose and especially cotton. They are suitable both for the exhaust process and for dyeing according to the pad dyeing process, according to which the goods are impregnated with aqueous and, if appropriate, also salt-containing dye solutions, and the dyes are fixed after an alkali treatment or in the presence of alkali, if appropriate with the action of heat.

They are also suitable for printing, especially on cotton, but also for printing nitrogen-containing fibers, e.g. of blended fabrics containing wool, silk or wool. It is advisable to subject the dyeings and prints to a thorough rinsing with cold and hot water, if appropriate with the addition of a dispersing agent and promoting the diffusion of the unfixed portions.

The production of the monoazo intermediate compounds is not described in all cases in the following exemplary embodiments, but it is readily apparent from what has been said above.

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

example 1

To an ice-cold, neutral solution of 5.94 parts of the dye of the formula nh,

(12)

In 200 parts of water, a solution of 1.0 part of cyanuric fluoride in 3 parts of toluene is added dropwise in the course of 5 minutes and the pH of the reaction mixture is kept between 6 and 7 by simultaneous dropwise addition of 1N sodium hydroxide solution. After complete acylation to the amino group, the solution of the difluorotriazine dye is mixed with 1.07 parts of o-toluidine, heated to 30 to 35 ° and the pH of the solution is kept between 7 and 8 by dropwise addition of 1N sodium hydroxide solution. After the reaction has taken place, the aminofluorotriazine dye Add 5% by volume of salted salt and filtered off. The dye paste is intimately mixed with a saturated aqueous solution of 1.0 part of disodium hydrogen phosphate and dried in vacuo at 40 to 50 °.

The dye thus obtained dyes cotton in shades of reddish brown.

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

40

45

example

Amines

55

ammonia

Mehylamine

Ethanolamine

Diethanolamine

Taurine

example

Amines

7

n-butylamine

8th

aniline

9

N-methylaniline

10th

N-ethylaniline

11

m-toluidine

12th

p-toluidine

13

m-chloroaniline

14

p-chloroaniline

15

o-anisidine

16

p-anisidine

17th

p-phenetidine

18th

p-aminobenzoic acid

19th

Aniline-3-sulfonic acid

20th

4-aminoacetanilide

21st

3-aminophenylurea

22

4-aminophenylurea

23

Diethylamine

24th

Morpholine

25th

2-naphthylamine-6-sulfonic acid

26

4-aminosalicylic acid

60 Example 27

By reacting 5.94 parts of the dye of the formula

(11)

633309

8th

With cyanfluoride and o-toluidine according to the information in Example 1, a dye is obtained which dyes cotton in violet tones of brown.

Example 28

By reacting 6.74 parts of the dye of the formula

SOoH

Vi

'/ V HH-N = N - \ _) - M2

H03S '"SO ^ H S03H

with cyanuric fluoride and o-toluidine as described in Example 1, a dye is obtained which dyes cotton in brown tones.

A similar dye is obtained when the isomer of the formula

OH

is assumed.

30th

Example 29

To an ice-cold solution of 19.35 parts of 4- (4'-aminobenzoylamino) -l-aminobenzene-2,5-disulfonic acid in 300 parts of water, a solution of 5.0 parts of 35 cyanuric fluoride is let in in 5 to 10 minutes 7 parts of toluene are added dropwise and the pH of the reaction mixture is kept between 6 and 7 by the simultaneous addition of 1N sodium hydroxide solution.

After complete acylation of the one amino group, the solution of the primary condensation product 40 is mixed with a neutral solution of 8.65 parts of metanilic acid in 30 parts of water, heated to 30 to 35 ° and the pH of the solution is maintained by dropwise addition of 1N sodium hydroxide solution between 7 and 8. The solution of the monofluorotriazine compound is cooled to 0 to 5 ° and diazotized by adding 25 parts of 45 parts of 2N sodium nitrite solution and 15 parts of 10N hydrochloric acid. The diazo compound thus obtained is then poured into a neutral solution of 19.75 parts of l-hydroxy-7-phenylamino-naphthalene-3,6-disulfonic acid in 200 parts of water, to which 33 parts of sodium bicarbonate were added before the coupling. 50

The dye formed is salted out with 10% by volume of sodium chloride and filtered off. After mixing with a concentrated, aqueous solution of 2 parts of disodium hydrogen phosphate, the dye paste is dried in vacuo at 45 °.

The dye thus obtained dyes cotton in brown tones.

A similar dye is obtained when the coupling component used is l-hydroxy-7- (3'-sulfophenylamino) -naphtha-lin-3-sulfonic acid.

Example 30

14 parts of cyanuric fluoride are added dropwise to an ice-cold, neutral solution of 26.8 parts of 1,4-phenylenediamine-2,5-disulfonic acid in 300 parts of water, the pH being added by simultaneous addition of 2N sodium hydroxide solution 6 to 6.5 is held. For the difluorotriazine compound, a neutral solution of 18 parts of metanilic acid in 60 parts of water is then added, the temperature of the reaction mixture is allowed to rise to room temperature and the pH is kept at 6.5 to 7 with 2N sodium hydroxide solution,

The mixture is cooled to 0 ° with ice and diazotized with 35 parts of 10N hydrochloric acid and 25 parts of 4N sodium nitrite solution. When coupling to 39.5 parts of l-hydroxy-7- (3'-suffophenylamino) -naphtha-lin-3-sulfonic acid in the presence of sodium bicarbonate, a dye is formed which, after isolation, dyes cotton in brown tones.

Dyeing Instructions I

2 parts of the dye obtained in Example 1 are dissolved in 100 parts of water with the addition of 0.5 part of sodium m-nitrobenzenesulfonate. A cotton fabric is impregnated with the solution obtained so that it increases by 75% of its weight, and then dried.

Then the fabric is impregnated with a 20 ° warm solution containing 5 grams of sodium hydroxide and 300 grams of sodium chloride per liter, squeezed to 75% weight gain, the dye is dampened for 30 seconds at 100 to 101 °, rinsed, soaped in for a quarter of an hour a 0.3% boiling solution of an ion-free detergent, rinses and dries.

Staining instructions II

2 parts of the dye obtainable according to Example 1 are dissolved in 100 parts of water.

The solution is added to 1900 parts of cold water, 60 parts of sodium chloride are added and 100 parts of a cotton fabric are added to this dye bath.

The temperature is increased to 40 °, 40 parts of calcined soda and another 60 parts of sodium chloride being added after 30 minutes. The temperature is kept at 40 ° for 30 minutes, rinsed and the soap is then soaped for 15 minutes in a 0.3% boiling solution of an ion-free detergent, rinsed and dried.

G

Claims (12)

633309 1 II N N ^ C ' CH, 1 11 N N I. F , N, C - Nile CH. \ /} \\ NH - C C - NH - (f 1-1 c c-z I 11 N N "* c" t F (1) wherein the phenyl radical A by Cj_4-alkyl, C ^ alkoxy, halogen, radical A may be substituted by carboxy or sulfo, and Z Nitro, carboxy and sulfo can be substituted, and Z is the meaning given in claim 1. optionally substituted amino group. 3. reactive dyes according to claim 2, of formula 2. reactive dyes according to claim 1, wherein the phenyl 2,4,6-trifluoro-s-triazine of the formula (2) wherein Z is an optionally substituted amino group. amino, which can be substituted by sulfo, N-methyl-N-phe- 2nd PATENT CLAIMS 1. Reactive dyes of the formula (3) characterized in that 1,4-diaminobenzene-2-sulfone-3,6-disulfonic acid is coupled, the resulting intermediate acid is diazotized and on l-hydroxy-7-phenylamino-naphthalene of the formula 3rd 3rd 633309 and an amine of the formula c c - f ! II n n I. f H-Z a diazotized diazo component of the formula (3) (4) (4) 4. Reactive dyes according to claim 3, wherein Z is -NH2, nylamino, N-ethyl-N-phenylamino or morpholino. Ci_4-alkylamino, N.N-Di-Cj ^ -alkylamino, ethanolamino, 30 5. Reactive dyes according to claim 4, wherein Z is phenyl N, N-diethanolamino, ß-sulfatoethylamino, phenylamino, the amino which can be substituted by chlorine, methyl, methoxy, ethoxy, carboxy by chlorine, methyl, methoxy, ethoxy, carboxy, sulfo, acety- and sulfo. lamino, ureido and hydroxy may be substituted, naphthyl (5) 65 (S03H) l-2 (eh. SO, H (S03H) 0-1 -NH j- H'O-l (6) 6. The reactive dye according to claim 5, the formula "NH £ 7 ^ - nh (S03H) 0-1 (S03H) 0.1 03H 0h nh - c f n * Nx C. ff n * c ' I. f nh - (7) • co nh- H (so3h) 1_2 0-1 (10) 7. The reactive dye according to claim 5, the formula OH -N = N C. (8th) implemented with each other in any order. io 2,4,6-trifluoro-s-triazine of the formula (7) and an amine of the formula (8) are reacted with one another in any order. 8. A process for the preparation of reactive dyes of the form a diazotized diazo component of the formula mei (1), according to claim 1, characterized in that a coupling component of the formula 60 r — v / h2 Ü AVS — NH 9. The method according to claim 8, characterized in. 11. The method according to claim 10, characterized in that a coupling component of the formula (5), in which net that ammonia, C 1 -C 4 -alkyl or the amine of the formula (8) Phenyl radical A can be substituted by carboxy or sulfo, amine, NN-di-C 1-4 alkylamine, ethanolamine, N, N-diethanolamine, can be used. 15 taurine, phenylamine caused by chlorine, methyl, methoxy, ethoxy, 10. The method according to claim 9, characterized in that carboxy, sulfo, acetylamino, ureido and hydroxy can be substituted, naphthylamine, which can be substituted by sulfo, N-methyl-N-phenylamine, N-ethyl-N-phenylamine or morpho- lin used. 12. The method according to claim 11, characterized in that the amine of the formula (8) is phenylamine, which can be substituted by (9) chlorine, methyl, methoxy, ethoxy, carboxy and sulfo. 13. The method according to claim 12 for the preparation of the 25 reactive dye of the formula that a coupling component of the formula oh (11) condensed with cyanuric fluoride and the resulting primary condensate with o-toluidine. Reactive dye of the formula 0h / N ^ —N = n - (/ —nh - c c - nh - // I II n n ^ c / I. f characterized in that 1,4-diaminobenzene-2-sulfononaphthalene-3-sulfonic acid is coupled, the intermediate acid formed is diazotized and on l-hydroxy-7- (3'-sulfophenylamino) compound of the formula 011 011 NH -h CO -, S03H (S03H) 1_2 -NH (12) condensed with cyanuric fluoride and the primary condensation product obtained is condensed with o-toluidine. 633309 mei