CS208117B2 - Method of making the reactive dyes - Google Patents

Abstract

The invention provides reactive dyes of the formula <IMAGE> wherein D is the radical of an organic dye which contains sulfo groups, R1 is hydrogen or C1-C4 alkyl, R2 is hydrogen, methyl or ethyl, X is a radical of the formula -SO2CH2CH2@, -SO2CH=CH2, -SO2CH2CH2OSO3H, -SO2CH2CH2OPO3H or -N(R3)SO2CH2CH2OSO3H, and R3 is hydrogen, methyl or ethyl, and the benzene or naphthalene radical can contain further substituents in addition to X.

Description

(54) A method for producing reactive dyes

The present invention relates to reactive dyes of the formula I

(I) in which:

D stands for a dye of a series of mono- or polyazo-dyes, metal-containing azo-dye complexes, anthraquinone dyes, phtaoccyenin dyes, formazan dyes, azomethionic dyes, nitroaryl dyes, dioxazine dyes, phenazine dyes or sulfosulfone dyes

R 1 is hydrogen or C 1 -C 4 alkyl,

R ₂ represents hydrogen, methyl or ethyl,

X is a radical of formula -SOgCHgCHgCl, -SOgCH ⁼ CHg5 -SgCHiCHgOSO3H, -SOpCHgCH-ΟΡΟ-, Η or

-N (R ₃ ) SO ₈ CH ₂ CH ₂ OSO ₃ H a

R 3 is hydrogen, methyl or ethyl, and the benzene or naphthalene ring may contain, in addition to X, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen such as fluorine, chlorine and bromine, nitro, hydroxy, carboxy and a sulfo group.

In the reactive dyes of the formula I, the radical D is in particular a dye residue of mono- or polyazo, metalocomppexazo series, aetraquinone series, [alpha] -alkylene, formazan series, azomethine series , nitroaryl series, dioxesin series, phenazine series or stibbene series

Preferred are reactive dyes of the formula I in which D represents a residue -or disazo dyes.

The substituent R, in formula I, as a C1-C4 alkyl group, is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl. '

If the moiety bonded via the bridged Clen -N (Rg) to the tri min ring is a nOTthalene moiety, the moiety may be bonded to the beta position.

The remainder of the organic dye D in formula I containing sulphocycles ¹ may contain, in addition to one or more suito groups, further substituents, such as C 1 -C 4 alkyl groups such as methyl, ethyl, propyl, isopropyl and butyl, 1-alkoxy groups. up to 4 carbon atoms such as methyl, ethoxy, propoxy, isopropoxy and butoxy, acylamino β of 1 to 6 carbon atoms such as acetyl amino, propionylamino and benzoylamino, halogen such as fluorine, chlorine and bromine, nitrostapine, cyano, cyano carbanol, ureido, hydroxy, carboxy and sulf methyl.

The benzene or naphthalene radical in the formula I may contain, for example, the following substituents in addition to X: for example: C1 -C4 alkyl, halogen such as fluorine, chlorine and bromine, nitro, hydroxy, carboxy and salt.

Preferred are reactive dyes of the formula I in which R @ 1 is hydrogen, methyl or ethyl and R @ 8 and R @ 8 are each hydrogen.

which means

Reactive dyes of the general formula II form an important group

OH

F (II)

A benzene or benzene radical having cis 1 or 2, n number 0 or 1 and n number 0 or 1, wherein the benzene or naphthalene radical A and the benzene radical B may contain an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 halogen, such as fluorine, chlorine and bromine, nitro, hydroxy, carboxy. and sulfo, and

X is as defined in Formula I.

Other substituents in the benzene or naphthalene residue A and in the benzene residue B are the same substituents mentioned above as possible substituents in illustrating formula I in residue D.

If residue D and / or A contains co-exchange groups such as hydroxy, carboxy, amine and sulfo, the heavy metal reactive dyes of formulas I and II are also suitable.

A valuable reactive dye group characterized by formula II is a reactive dye of formula III

The preparation of the reactive dyes of the formula I as well as their metal complexes consists in condensing 2,4,6-trifluoro-s-triazine of the formula IV

(IV) an organic dye containing sulfo groups of formula V

D-NH wherein

D and R, are as defined above, or pre-sell an organic dye of formula V, containing a sulfo group and an amine of formula VI

(VI) in which:

Rg and X have the above meaning, in any order to the reactive dye of formula I, and in the case of deserts of dye preforms, these are converted to the desired final dyes of formula I, whereupon the reactive dyes obtained are optionally treated with heavy kpv agents.

As the organic dyes of formula (V) which contain a sulfo group, the dyes in which D is a dye residue of a series of mono- or polyazo dyes, metal-containing azo dyes, anthraquinone dyes, phthaocyaniin dyes, foazenene dyes, azomethionic dyes, nitroary dioxazine dyes, phenazine dyes or stibean dyes.

Preferably, sulfo-containing organic dyes of the formula V are used as starting materials in which D is a mono- or disazo dye residue.

Since the individual reaction steps mentioned above may be carried out in different order, optionally partially or simultaneously, different process variants are possible.

In general, the reaction is carried out in a step-wise manner, wherein the order of the simple reactions between the individual reactants of formulas IV, V and VI can be arbitrarily arbitrary.

The important process variants for the preparation of the reactive dyes of the formula I are that they are:

1. 2,4,6-trifluoro-s-triazine of formula IV is condensed with an organic dye of formula V containing sulfo groups and the primary condensation product is condensed with a β amine of formula VI,

2. The 2,4,6-trifluoro-s-triazine of formula IV is condensed with an amine of formula VI and the primary condensation product is condensed with an organic dye of formula V containing a sulfo group.

According to one variation of the above process, reactive dyes of formula I wherein D is a sulfo group-containing organic dye residue consisting of two or more than two components can be produced by condensing a dye component of formula V containing a group - NH-, 2,4,6-trifluoro-s-triazine of formula IV-1 and aminobenzene of formula VI, and at any stage of the process, reacting with the remaining component (s) of the dye of formula V to form a reactive dye of formula I.

Examples of such organic dyes which consist of two or more than two components are: monoazo dyes, disazo dyes, trisazo dyes, tetrazo dyes, complex metal-dyes, formazan dyes and atomethine dyes.

The above-described process variation is particularly important for the production of reactive dyes of formula I in which D is a sulfo group containing azo dye residue. In this residue, the part of the azo dye to which the s-triazine residue is bound can be either a diazo-loading residue or a coupling component residue. This gives two variants of the above-described process variation.

One of these two variants is to condense a diazo component containing the -NH- group,

I «1

The 2,4,6-trifluoro-s-triazine of the formula IV, the obtained condensation product, is diazotized and coupled to the coupling component, before or after it is reacted with the amine of the formula VI.

The second variant is that the coupling component which contains the -NH- group,

1 ^B t is condensed with a 2,4,6-trifluoro-s-triazine of formula IV and the diazotized diazo component is coupled to the condensation product thus obtained, before or after reaction with an amine of formula VI.

According to this variant of the preparation, reactive dyes of the formula I can be prepared which contain 2 reactive s-triazine residues, in that the diazo component containing the group -NH-,

I ^R i is condensed with 2,4,6-trifluoro-s-triazine of formula IV, further the coupling component containing the -NH- group is condensed with 2,4,6-trifluoro-ss-triazine of formula IV, the condensation product of diazo components is diazotized and coupled to the condensation product of the coupling component and before or after the reaction with amine VI is carried out.

Reactive dyes of formula I containing two or more than two reactive s-triazine residues can also be prepared by condensing sulfo groups containing an organic dye of formula V, which in residue D contains further -NH- groups, with a corresponding amount of 2, 4.65

-trifluoro-s-triazine of formula IV, so that two or more s-trlazine residues are introduced into the dye molecule.

A preferred embodiment of the process for the preparation of reactive dyes of formula I consists in using sulfo groups containing organic dyes of formula V in which D is a mono- or disazo dye residue, or in that the diazo components and / or the coupling components contain the group -N (R) H, condensed with 2,4,6-trifluoro-s-rrazine of formula IV, and then or thereafter with an amine of formula VI, the preparation of the dye is completed by coupling with the other component (s) with other monn- optionally disazo dyes. ·

A further preferred embodiment is that the organic dye of formula (V) containing a sulfo group in which R 1 is hydrogen, methyl or ethyl and amines of formula (VI) in which R ₂ and R 3 are hydrogen are used as training substances,

Preferred reactive dyes of formula II are prepared by reacting the diazotized amino compound of formula VII a-nh ₂ (m) coupling component of formula VIII in any order by compilation and condensation in any order

HIM

2,4,6-s-Trifluoro-s-trizilr 'of formula IV and an amine of formula IX

X (IX) to form a reactive dye of formula II.

The most preferred process variants for the production of reactive dyes of the formula II are that they are:

1. a diazotized amino compound of formula VII couples with a coupling component of formula VIII to form an amino compound of formula X

OH

(X) this is condensed with 2,4,6-1,13,3,3,5,5-azine of formula IV and the obtained primary condensation prodlet is condensed with an amine of formula IX to form a reactive dye of formula II, or

2. the coupling component of formula VIII is condensed with 2,4,6-trifluoro-1,3,5-triazine of formula IV, the primary condensation product obtained is condensed with an amine of formula IX and the resulting secondary product is coupled with a diazotized amino compound of formula VII to reactive or a dye of the formula II;

3. The coupling component of formula 8 is condensed with a 2,4,6-trifluoro-1,3,5-triazine of formula IV, the diazotized eunino compound of formula VII is coupled to the obtained primary condensation product and the obtained azo compound is condensed with an amine of formula IX to form a reactive dyes of formula II.

If the finished reactive dyes of formula (I) and / or of formula (II) contain complexing groups, they can be reacted additionally with 8 heavy metal leaching agents.

An especially valuable reactive dye of the formula III is preferably produced according to process variant 2 above, by condensing 1-amino-8-hydroxynaphthalene-3,6-dieulfonic acid with 8 cyanuric chloride, the primary condensation product being condensed with 1-aminobenzene-3. -beta-sulfetoethylsulfone and diazotized 2-aminonaphthalene-1,5-disulfonic acid is coupled to the secondary condensation product obtained.

The starting materials for the preparation of the reactive dyes of the formula I include:

a) 2,4,6-Trifluoro-s-triazine (cyenurfluoride) of formula IV

b) sulfo groups containing organic dyes of formula V

Monoazo compounds of formula XI

in which

D ₁ represents at most a bicyclic aryl radical which does not contain azo- and -NHR-groups, R ₁ represents hydrogen or an alkyl group of β 1 to 4 carbon atoms and the -NHR 4 group is preferably attached at the 5, 6, 7 or 8 position of the naphthalene nucleus and which may contain a sulfo group at the 5 or 6 position of the naphthalene core.

D ₁ may in this case be a residue of a naphthalene or benzene series, free of azo substitution, for example a stilbene, diphenyl, benzthiazolylphenyl or diphenylamine residue. This group also includes related dyes in which the -NHR- group, instead of being bound to the naphthalene nucleus, is bound to a benzoylamino or aniline group bound at the 5, 6,7 or 8 position of the naphthalene nucleus.

Particularly valuable starting dyes are dyes in which the sulfonated phenyl or naphthyl radical is, in particular those containing an -SO4H group in the ortho position to the azo group, the phenyl radical may be further substituted, for example by halogen atoms such as chlorine, alkyl radicals, such as methyl, acylamino, such as acetylamino, and alkoxy, such as methoxy.

2. The disazo compounds of formula XI wherein the radical is an azobenzene series, an azonephthalene series or a phenylazonaphthalene series and a naphthalene nucleus is substituted with an -NHR 4 - group, and optionally a sulfonic acid, as in class 1.

3. Monoazo compounds of formula XII

(XII)

Němž in which

D is at most a bicyclic aryl radical as described in class 1, and preferably a disulfonaphthyl or stibbene radical,. as defined above, and the benzene ring may contain other substituents such as halogen atoms or alkyl radicals, alkoxy radicals, carboxylic acid radicals, ureido radicals and acylamino radicals.

4. Mono and diazo compounds of formula XIII

H-N-D.-N = N-K (XII)

I ¹

Ri in which

Dj is an arylene radical, such as an azobenzene, azonaphthalene or phenylazonaphthalene radical, or preferably a most preferably bicyclic arylene radical of the benzene or naphthalene series, and

K represents a naphtholsulfonic acid residue or a residue of an enolized or olizable ketomethylene compound (such as acetoacetarylide or 5-pyrazolone) having a hydroxyl group ortho-to the azo group, and

R @ 1 is preferably a benzene series radical which contains a sulfo group.

5. Mono or diazo compounds of formula XIV ϋ, -Ν = - Κ - 1ΗΗ, (XIV) in which:

D | means the rest of the types defined above for D, in classes 1 and 2 and

K 1 represents an enolizable ketomethylene derivative (such as acetoacetarylide or 5-pyrazolone) with an -OH group in the ortho position to the azo group.

6. Complexing the compound with metals, for example, dyes of formulas XI to XIX with copper, chromium and cobalt, wherein K and K are as defined above, and a meesisable group (e.g., hydroxyl, lower alkoxy, or carboxylic acid residue) is present in the ortho- position to the -azo group in the remainder

Class 1:

a-ann-oo-1-yddoox-2- (2'-sulfophenylaz-naphthalene-3-suioonic acid),

6- mm thylamino-1-hydroxy-4-amino-1-hydroxybutyl-10-sulfonic acid 10-amino-1-hydroxy-4 - (- &lt; / RTI &gt; disulfonic acid,

8-chloro-1H-droxy-2- (4'-chloro-1-sulfobonylazo) oaftaeen-3,5-disulonic acid,

7-amine to --- 25'-disulfoaen-lase) -1-h-drtoynoatalbo-3-sulfooic acid, 7-bethoxyl-oxo-2- (2'-sulfonylbenzo) -1-h-oxo-olaalene -3-sulfonic acid,

7-Methyl-apinot-2 - (('- ρ-buto-2'-sulphophol-lase) -1-hydroxy) -natalen-3-sulaonic acid

8- (3'-Aminobenzoylamino) -1-hydroxy-2- (2'-sulphobenzoate) naphthalene-3,6-disuccinic acid, α-amino-1-h-drooy-2, -'- eztoaOtalene- 1 'зЗ ^^ б - ^^ ааиЮопс ^ acid, 8-amino-1-h-dimethoxy-2, -'- ether-tert-1' ^^ '- ^ виЮтс ^ acid, ε-amino-Уydtoy-2, 2 '' eztnaatelbo-1 ', 3,5'-trisulonic acid,

6-bis-apinol-1-hydroxy-2, -'-ezotoeeaeen-1,3,5,5-trisulonic acid,

7-Apino-1-hydroxy-2, -'-aztoalteleo-1 'Z' -pyridine acid,.

8-Amino-1-h-dimethoxy-2- (4'-methyl-2'-sulaoabol-lez) oeltaleo-3,6-disulphonic acid; and

6-Amino-1-h-hydroxy-2- (-'-sulaoaenazilaz) ethyl-3,5-disulfonic acid.

and

Class 2:

8-amino-1-hydroxy-2- [4 '- (2' '-sulfophenylezo) -2'-methoxy-5'-methylphenylazo] naphthalene-3,6-disulfonic acid,

8-amino-1-hydroxy-2- [4 '- (4''-methoxyphenylazo) -2'-carboxyphenylazo] naphthalone-3,6-disulfonic acid,

8-amino-1-hydroxy-2- [4 '- (2' * -hydroxy-3 * *, 6 '' -disulfo-1 * * -naphthyllazo) -2'-carboxyphenylazo-naphthalene-3,6-disulfonic acid,

4,4-bis- (8-amino-1 '' - hydroxy-3 '', 6 '' - disulfo-2 '' - naphthylazo) -3,3'-dimethoxydiphenyl, and

6-amino-1-hydroxy-2- [42''-sulfophenylazo) -2'-methoxy-5'-methylphenylazo] naphthalene-3,5-disulfonic acid.

Class 3:

2- (4'-amino-2'-methylphenylazo) naphthalene-4,8-disulfonic acid,

2- (4'-amino-2'-acetylaminophenylazo) naphthalene-5,7-disulfonic acid,

4-nitro-4 '- (4' '- methylaminophenylazo) stilbene-2,2'-disulfonic acid,

4-nitro-4 '- (4-amino-2' '- methyl-5' '- methoxyphenylazo) stilbene-2,2'-disulfonic acid; 4-amino-4 '- (4''-methoxyphenylazo) stilbene-2,2'-disulfonic acid and 4-amino-2-methylazobenzene-2', 5'-disulfonic acid.

Class 4:

1- (2 ', 5'-dichloro-4'-sulfophenyl) -3-methyl-4- (3' * -amino-6''-sulfophenylazo) -5-pyrazolone, - (4 ^{z '} sulfophenyl) -3 —Carboxy-4- (4 ' -amino-2 ' -sulphophenylazo) -5-pyrazolone, - (2 ' -methyl-5 ' -sulphophenyl) -3-methyl-4- (4 ' -amino-2) 'Sulfophenylazo) -5-pyrezolone

1- (2'-Sulfophenyl) -3-methyl-4- (3 '' - amino-6 '' - sulfophenylazo) -5-pyrazolone,

4-amino-4 '- (3' '- methyl-1''-phenyl-4''-pyrazol-5-yylazo) stilbene-2,2'-disulfonic acid, 4-amino-4' - (2 ' '-hydroxy-3' ', 6' '- disulfo-1' '- naphthylazo) stilbene-2,2'-disulfonic acid, 8-acetylemino-1-hydroxy-2- (3'-amino-6'-sulfophenylazo) ) Naphthalone-3,6-disulfonic acid

7- (3 ^of -sulfophenylamino) -1-hydroxy-2- (4-amino-2'-carboxyphenylazo) naphthalene-3-sulfonic acid,

8-Phenylamino-1-hydroxy-2- (4'-amino-2'-sulfophenylazo) naphthalene-3,6-disulfonic acid and 6-acetylamino-1-hydroxy-2- (3'-amino-6 sulfophenylazo) naphthalene -3-sulfonic acid.

Class 5:

- (3'-aminophenyl) -3-methyl-4- (2,5-disulfophenylazo) -5-pyrazolone,

1- (3'-eminophenyl) -3-carboxy-4- (2''-carboxy-4''-sulfophenylazo) -5-pyrazolone,

4-amino-4 '- [3' '- methyl-4- (2 *, 5'-disulfophenylazo) -1' '- pyrazol-5' - onyl] stilbene-2,2 '- disulfonic acid and

1- (3-aminophenyl) -3-carboxy-4- [4- (2 ', 5'-disulfophenylazo) -2'-methoxy-5''-methylphenylazo] -5-pyrazolone.

Class 6:

Cu-complex of 8-amino-1-hydroxy-2- (2'-hydroxy-5'-sulfophenylazo) naphthalene-3,6-disulfonic acid,

Cu-complex-6-amino-1-hydroxy-2- (2'-hydroxy-5'-sulfophenylazo) naphthalene-3-sulfonic acid, Cu-complex 6-amino-1-hydroxy-2- (2'-hydroxy -5'-sulfophenylazo) naphthalene-5-disulfonic acid,

Cu-complex-8-amino-1-hydroxy-2- (2'-hydroxy-3'-chloro-5'-sulfophenylazo) naphthalene-3,6-disulfonic acid,

6-methylamino-1-hydroxy-2- (2'-carboxy-5'-sulfophenylazo) -naphthalene-3-sulfonic acid Cu complex,

8-Amino-1-hydroxy-2- [4 '- (2-sulfophenylazo) -2'-methoxy-5'-methylphenylazo] naphthalene-3,6-disulfonic acid Cu complex,

6-Amino-1-hydroxy-2- [4 * * - (2 * *, 5'-disulfophenylazo) -2'-methoxy-5'-methylphenylazo] naphthalene-3,5-disulfonic acid Cu complex,

Cu-complex 1- (3'-amino-4'-sulfophenyl) -3-methyl-4- [4 ** - (2 *, 5 ** '-disulfophenylazo) -2 * * -methoxy-5 *' - methylphenylazo] -5-pyrazolone,

Cu-complex 7- (4'-amino-3'-sulfoanilino) -1-hydroxy-2- [4- (2 *, 5'-dinulfophenylazo) -2''-methoxy-5''-methylphenylazolnaphthalene-3- sulfonic acids,

Cu-complex of 6- (4'-amino-3'-sulfoanilino) -1-hydroxy-2- (2'-carboxyphenylazo) naphthalene-3-sulfonic acid,

1: 2-Cr-7-amino-6'-nitro-1,2'-dihydroxy-2,1'-azonaphthalene-3,4'-disulfonic acid complex,

1: 2-Cr-6-amino-1-hydroxy-2- (2'-carboxyphenylazo) naphthalene-3-sulfonic acid complex,

1: 2-Cr-8-amino-1-hydroxy-2- (4'-nitro-2'-hydroxyphenylazo) naphthalene-3,6-disulfonic acid complex,

1: 2-Co-complex of 6- (4'-amino-3sulfoanilino) -1-hydroxy-2- (5'-chloro-2'-hydroxy-phenylazo) -naphthalene-3-sulfonic acid,

1: 2-Cr-complex of 1- (3'-amino-4'-sulfophenyl) -3-methyl-4- (2 ** -hydroxy-sulfo-1'-naphthylazo) -5-pyrazolone and

1: 2-chromium complex of 7- (4'-sulfoanilino) -1-hydroxy-2- ^(4-amino-9 * 2 * '- karboxyfenylazo) naphthalene-3-sulfonic acid.

Particularly important azo dyes which can be used for the production of reactive dyes of the formula I are azo dyes of the formulas XV, XVI and XVII

(XVII) in which:

K is a benzene, naphthalene or heterocyclic series coupling moiety, ⁿ acyl means a low molecular weight aliphatic acyl radical containing up to 3 carbon atoms or an aromatic radical containing up to 8 carbon atoms, and

R] has the meaning given in formula I as well as complex azo dyes with metals of the formulas XVIII and XIX

(вОзН ^ -з (XVIII))

in which

R 1 and acyl have the meanings given above in illustrating formulas XV, XVI and XVII and Не means copper, chromium or copper.

Class 7:

Anthraquinone derivatives which contain a group of the formula -NH1R, in which R8 is as defined above, on an alkyl-amino or arylamino-amino group, which itself binds in the alpha position of the anthraquinone core, in particular of formula XX

nh-z-nhh, wherein the anthraquinone core may contain an additional sulfonyl group at the 5-, 6-, 7- or 8-position and Z * represents an o-ring member, which is preferably a divalent benzene moiety, for example phenylene, diphenylene or * 4 -ntiCt: an or azobenzene residue.

Preferably, Z 'should contain one sulfo group per benzene ring present.

Examples

2-Amino-2'-amino-2,3'-disulphonic acid and corresponding 2,3 ', 5-, 2,3', 6- and 3 ', 7'-C8nanoic acids Aminoaniline-2,3'-di8ui: Con () acid and the corresponding -2,3'-5-triionic acid,

- jminoc4- [4 * j (0 * jnamioojnnyjazo) 1on-Lino] wtrachinone-2,2 * *, S-trisufonic acid, jjoinoc4- [4 * n0) iodo-β-benzoxyaniliniletrachinone-2,5-disulfonic acid, n-amino-1'-N-amino-aniline-anthra-hin-3-ene-3-tri-sulfonic acid and cdpio-2, 4-dufonic acid,

-amino-4- [4- (4 '' - joinoinnyl) -nifrorolantrichloro-2,3'-trifluorophosphoric acid,

1-iodo-4- (4-anthylcino) 8-aminoCeno 2 -trachinone-2,3 * -difluoroic acid - and the like-2, 5'-5'-thiocyclonic acid,

-nm.uty4- (4 [-n-1'-phenynoantacin-n-Cnetrotrachinone-2,3 '- dihydro-4'-acid),

- (4-Methyl-isoquinolin-2-ynoquinolin-2-yl) phonquinone-2-8Ulfonic acid,

- (4 * -aminoanilino) anthraquinone-2,3 * -disulfonic acid and

-aclio 4- (0O-amine! O * 2 of _my thoiyanllinoiaoilrachinon-0,3'_disuffonové kysdina.

Class 8:

Phthalocyanine derivatives of formula XXI

(XXI) about

Pc is the nucleus of phthalocia-i-u, preferably copper phthalocyanine, ω is Uydrxy and / or omino,

Z 'is a bridging member, preferably an aliphatic, cycloaliphatic or aromatic bridging moiety; in each case 1, 2 or 3 and may be the same or different, provided that n + m is not a sentence! 'than 4.

The phytoocynyl dye derivatives which may be used as starting materials are preferably metal-containing flasks, such as plasticizing agents, which contain at least one sulfhydryl group and at least one sulfo group of the formula: NHIR, wherein R 1 has from above. this meaning.

R'ONHR group or -NHR ^ may be bonded to benzene rings f taicc; on "(lnooéUo core directly through MEBO dvojvozmý bridge, for example through mmstek ofemyien-, CO-fenylan-, OSO ₂ -phenylene, oNHOenylen OS-feiyLeh - oOofeiyleh-, OCH ₂ O-fee-tension member, _OCH2 0o0eimrlen, _-CH2 ofemylemo, OSH O ^ <^ i ^) ^ 1 ^ l ^ i ^ - oSOpCCH-ffenyen-, oS0 ₂ 0R- ffenym-, OCH ₂ -, OSO ₂ NR arylan-, ONR-COofehlleh-, district-oso-ofe-Leu-, oSOoO-FFE-Leu-OCH ₂ 0R "FFE-Leu-OCH ₂ lffl-CC- Oenylene-, SO2NRoolkile--, oCHOR-alkklene-, oCOOR-phen-len-, oCOOR-arylene-, oSO4- or oCO2- _?

In the above double bonds, R is hydrogen, alkyl or cycloalkyl, and arilm is a bivalent aromatic, optionally with, for example, a halogen, alkyl or alkoxy substituted radical in which the terminal bonds are optionally bonded to the same or different nucleus, and alkyln- a double-chain radical containing optionally hateo atoms, such as nitrogen in the chain, for example the radical -CH2CH3-NH-CH3Cr2.

Examples of too-biotrans-aromatic radicals referred to as orileh include: an arietic nucleus, for example, a benzene nucleus, a ο ^ οΐβ-β nucleus, a ocrolidium nucleus. and a cobalt core, which may contain additional substituents, and radicals of formula XXII &apos;

wherein the benzene rings may contain additional substituents and op-- means m-2-methyl, for example oCH = CH-, oN4-, oSo, oOo, oSO4-, oM0 = N-, oN = N-, oNH -CO-NH-CO-ICH-, o-CHoCHgO- or

(ШП).

Examples

3- (3'-amino-4'-sulfophenyl) 8-sulfamoyl-amine-phthalocyanine-tri-3-8-sulfonic acid, di-4- (3'-amino-4'-sulfophenyl) sulfamoyl-amine-phthalocyenine-di -4-sulfonic acid,

3- (3'-Aminophenyl sulfamoyl) -3-sulfamoyl-meth-phthalocyanine-di-3-sulfonic acid, having phthalocyenine-4-N- (4-amino-3-8 sulfophenyl) sulfonamido-4 *, 4 ** , 4 *** - trisulfonic acid, cobalt-phthalocyanine-4,4 * -di-N- (4'-amino-4'-sulfophenyl) carboxamido-4 * *, 4 * * '- dicarboxylic acid and copper-4 - (4'-amino-3 ^- sulphobenzoyl) phthalocyanine.

Mixtures of phthalocyanine may also be used. Thus, a mixture of approximately equal parts of [alpha] 3-phthalocyanine-N- (4-amino-3-sulfophenyl) sulfonamidotrisulfonic acid and [beta] 3-phthalocyanine-di-K- (4-amino-3-sulfophenyl) ) sulfonamidodisulfonic acids.

Class 9:

Nitro dyes of the general formula XXIV

Z I

OgN-D-N-Q (XXIV) wherein

D represents a naphthalene or benzene ring which may be substituted for a longer period of time, the nitrogen atom N is in the ortho position to the nitro group,

Z is hydrogen or an optionally substituted hydrocarbon radical; and

Q is hydrogen or an organic radical bonded to a nitrogen atom by a carbon atom, and wherein

Q and Z are not both hydrogen, and the residue Q can be bound not to the residue Z when Z is a hydrocarbon residue, or to the residue

D in the ortho position to the nitrogen atom N to form a heterocyclic ring and containing at least one group of formula -NHR 4, wherein R _{1 is} as defined above; in particular nitro color XXV

V-NH-B-NHR. (XXV)

I 'no ₂ in which

V and V are monocyclic eryl nuclei and the nitro group in the remainder of V is bonded in the ortho position to the NH group.

Example

4-amino-2'-nitrodiphenylamino-3,4'-disulfonic acid.

Class 10:

Complexes of formazan dyes with metals of general formula XXVI

'NH

(η = 1 or 2) (XXVI) in which

Q represents an organic residue, a nitro group or a cyano group,

А а В means diazo components of the benzene, naphthalene or heterocyclic series,

Y 1 and Y ₂ represent a substituent capable of complex bonding with a heavy metal and bonded at the o-position to the azo group and

R1 is as defined above.

In particular, the radical Q is a benzene radical, such as a phenyl radical or a sulphenyl radical, or a low molecular weight alkyl radical, such as a methyl radical, a low molecular weight alkanoyl radical, a low molecular weight, preferably 1 to 4 carbon atoms containing alkoxycarbonyl, benzoyl or heterocyclic radicals; are preferably phenyl radicals substituted with sulfo, sulfonamido or alkylsulfonyl groups.

As substituents Y and Y @ ₂ are in particular hydroxyl groups and carboxyl groups. Suitable heavy metals are copper, chromium, cobalt and nickel.

Examples

Cu complex of 2-carboxy-2'-hydroxy ^{of the} 3 ' -amino-1,3,5-trifenylformazfcn-4 ^from 5 '* »* 3 * ~ tetraacetic acid

Cu complex of 2 ', 2'dihydroxy-3'-amino-5 * -methylsulfonyl-1,3, 5-trifenylformazan-3 ^/ * 5 * ', 4' ⁹ '-trisulfonové acid

Cu 'complex of 2'-carboxy-4'-amino-2' '- hydroxy-1,3,5-triphenylformazan-3' ', 5', 2 '' - trisulfonic acid,

2'-hydroxy-2'-carboxy-4'-amino-1,3,5-triphenylformazan-4 *, 4'-disulfonic acid Cu complex,

Cu complex of 2 *, 2 * '-dihydroxy-5' '-amino-1,5-diphenyl-3-methylformazan-5', 3 '' - disulfonic acid,

Cu complex of 2 *, 2 ** - dihydroxy-5'-amino-1,3,5-triphenylformazan-3 ', 3,5 ** - trisulfonic acid,

Cu-complex of 2'-carboxy-3'-amino-2 '' -hydroxy-3 * - (1''-phenyl-3 '* * * -methylpyrazole-5 ^from * *' -onyl-4 * * -azo -1,3,5-triphenylformazan-3 ^Z , 5,2,5-tetrasulfonic acid a

2 ', 2' '- Dicarboxy-1,5-diphenyl-3- (m-aminobenzoyl) formazan-4', 4 '- disulfonic acid Ni-complex.

The following diazo components and coupling components are particularly suitable for the production of the preferred reactive dyes of the formula I in which D is an azo dye residue:

200117

Diazo components:

aminobenzene,

1-amino-2-, -3- or -4-methylbenzene,

1-amino-2-, -3- or -4-methoxybenzene,

1-amino-2-, -3- or 4-chlorobenzene,

1-amino-2,5-dichlorobenzene,

1-amino-2,5-dichlorobenzene,

1-amino-3-methyl-.alpha.-methoxybenzene,

1-Amino-2-methoxy-4-nitrobenzene

4-aminodiphenyl,

-aminobenzene-2,3-or 4-carboxylic acid,

2-aminodiphenyl ether,

1-aminobenzene-2-, -3- or 4-sulfonamide,

N-methylamide, N-ethylamide, Ν, Ν-dimethylamide or Ν, Ν-diethylamide 1-aminobenzene-2-, -4-sulfonic acid, dehydrothio-p-toluidine sulfonic acid,

1-amino-3-trifluoromethyl-6-sulfonic acid,

1-amino-3- or -4-nitrobenzene,

1-amino-3- or -4-acetylaminobenzene,

1-aminobenzene-2-, -3- or -4-sulfonic acid,

1-aminobenzene-2,4- and -2,5-disulfonic acid,

1-amino-4-methylbenzene-2-sulfonic acid,

1-amino-3-methylbenzene-6-sulfonic acid,

1-amino-6-methylbenzene-3- or -4-sulfonic acid,

1-amino-2-carboxybenzene-4-sulfonic acid,

1-amino-4-carboxybenzene-2-sulfonic acid,

1-amino-4- or -5-chlorobenzene-2-sulfonic acid,

1-amino-6-chlorobenzene-3- or -4-sulfonic acid,

1-amino-3,4-dichlorobenzene-6-sulfonic acid,

1-amino-2,5-dichlorobenzene-6-sulfonic acid,

1-amino-2,5-dichlorobenzene-4-sulfonic acid,

1-amino-4-methyl-5-chlorobenzene-2-sulfonic acid, 1-amino-5-methyl-4-chlorobenzene-2-sulfonic acid,

1-amino-4- or -5-methoxybenzene-2-sulfonic acid

1-amino-6-methoxybenzene-3- or -4-sulfonic acid, 1-amino-6-ethoxybenzene-3- or -4-sulfonic acid,

1-amino-2,4-dimethoxybenzene-6-sulfonic acid,

-emino-2,5-dimethoxybenzene-4-sulfonic acid, 1-amino-3-acetylaminobenzene-6-sulfonic acid,

1-Amino-4-acetylaminobenzene-2-sulfonic acid

-amino-3-acetylamino-4-methylbenzene-6-sulfonic acid,

2-amino-1-methylbenzene-3,5-disulfonic acid,

1-amino-4-methoxybenzene-2,5-disulfonic acid,

1,4-dlaminobenzene-2,5-disulfonic acid,

1-amino-3- or -4-nitrobenzene-6-sulfonic acid,

1- aminonaphthalene,

2-aminonaphthalene,

1-aminonaphthalene-2-, -4-, -5-, -6-, -7- or -8-sulfonic acid,

2-aminonaphthalene-3,6- or -5,7-disulfonic acid,

1-aminonaphthalene-3,6- or -5,7-disulfonic acid,

2-aminonaphthalene-1,5--1,7-, -3,6-, -5,7-, -4,8- or -6,8-disulfonic acid,

-aminonaphthalene-2,5 »7-trisulfonic acid,

2-aminonaphthalene-1,5,7-, -3,6,8- or -4,6,8-trisulfonic acid,

1-hydroxy-2-aminobenzene-4-sulfonic acid,

1-hydroxy-2-eminobenzene-5-sulfonic acid,

-3- or

1-hydroxy-2-aminobenzene-4,6-disulfonic acid,

1-hydroxy-2-amino-4-acetylatninobenzene-6-sulfonic acid,

1-hydroxy-2-amino-6-acetylaminobenzene-4-sulfonic acid, 1-hydroxy-2-amino-4-chlorobenzene-5-sulfonic acid,

1-hydroxy-2-amino-4-methylsulfonylbenzene,

1-amino-2-hydroxy-6-nitrina-phthalene-4-sulfonic acid,

2-amino-1-hydroxynaphthalene-4,8-disulfonic acid,

4-aminoazobenzene-3,4'-disulfonic acid,

3- methoxy-4-amino-6-methylazobenzen-2 * 4 ^of disulfonic acid and

3-methoxy-4-amino-6-methylazobenzene-2 ', 5'-disulfonic acid.

Coupling components:

phenol,

1-hydroxy-3- or -4-methylbenzene,

1-hydroxybenzene-4-sulfonic acid,

1-hydroxynaphthalene,

2-hydroxynaphthene,

2-hydroxynaphthalene-6- or -7-sulfonic acid,

2-hydroxynaphthalene-3,6- or -6,8-disulfonic acid,

1-hydroxynaphthalene-4-sulfonic acid,

1-hydroxynaphthalene-4,6- or -4,7-disulfonic acid,

1-Amino-3-methylbenzene

1-Amino-2-methoxy-5-methylbenzene

1-amino-2,5-dimethylbenzene,

3-aminophenylmoCoviny,

1-amino-3-acetylaminobenzene,

1-amino-3-hydroxyacetylaminobenzene,

1,3-diaminobenzene-4-sulfonic acid,

1-aminonaphthalene-6- or -8-sulfonic acid,

-amino-2-methoxynaphthalene-6-sulfonic acid,

2-aminonaphthalene-5,7-di sulfonic acid,

1-amino-8-hydroxynaphthalene-6-sulfonic acid,

1-amino-8-hydroxynaphthalene-2,4-disulfonic acid,

2-hydroxy-3-aminonaphthalene-5,7-disulfonic acid,

1-amino-8-hydroxynaphthalene-2,4,6-trl sulfonic acid,

1-hydroxy-8-acetylaminonaphthalene-3-sulfonic acid,

1-benzoylamino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid,

2-Benzoylamino-5-hydroxynaphthalene-7-sulfonic acid

2-Amino-5-hydroxynaphthalene-7-sulfonic acid,

2-methyl- or 2-ethylamino-5-hydroxynaphthalene-7-sulfonic acid,

2- (N-acetyl-N-methylamino) -5-hydroxynaphthalene-7-sulfonic acid,

2-ac ethylamino-5-hydroxynaphthalene-7-sulfonic acid,

2-amino-5-hydroxynaphthalene-1,7-disulfonic acid,

2-amino-8-hydroxynaphthalene-6-sulfonic acid,

2-methyl- or -ethylamino-8-hydroxynaphthalene-6-sulfonic acid,

2- (N-ac ethyl-N-methylamino) -8-hydroxynaphthalene-6-sulfonic acid,

2-Asylamino-8-hydroxynaphthalene-6-sulfonic acid,

2-amino-8-hydroxynaphthalene-3,6-disulfonic acid,

2-acetylamino-8-hydroxynaphthalene-3,6-disulfonic acid,

1-amino-5-hydroxynaphthalene-7-sulfonic acid,

1-amino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-acetylamino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1- (4'-aminobenzoylamino) -8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, - (4'-nitrobenzoylamino) -8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1- (3 ^s -aminobenzoylamino -8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1- (3'-nitrobenzoylamino) -8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid,

2- (4'-amino-1'-sulfophenylmino-5-hydroxyriaphthalene-4-sulfonic acid),

3-methylppyazol-4-one,

1-Lenil-3-methyl-5-pyrazolone

1- (4'-sulOoeenyl) --- metyil pirazoloo 5-1- (4 ^/ -sulflfenyl) lyaaool-5-ene --- aarЪoxylové acid,

1- (3'-Aminophenyl) -1-methyl-5-pyrazolone;

1- (2 *, 5 * -Disulphenol-4-yl) -3-methyl-5-pyrroleolone,

1- (2'-Methyl-4'-sulfonoyl) -) pyrazole-3-nitroic acid,

- (4 *, 8'-disulphonyl onl- [2 'D-1-methylthi] -pirazolone,

1- (5 ', 7'-Disulfonyl-E2 *]) -3-methyl-5-py (aeolone,

1- (2 *, 5) -dichloro-44'-sulfophelyl) -3-ethyl-5ppJazazole,

3- lminokklboneУ-4-methyl-6-hydroxypropyl-2-oe,

1-Ethyl-3-cyano- or 3-chloro-4-methyl) -6-oxypyridin-2-one;

-ethyl-3-sulpholin-4-methyl-6-hydroxy-piperidin-2-one,

2.4.6- triemino-3-klleppyidia,

2- (3'-sulfolinolylimino) -4,6, -diloino-3-klanpy (idi-,

2- (2'-Oxyoxyethoxy) -3-clin-4-methyl-6-aminopyridine,

2.6-blSi (2'-УyУdrxpetУyllllino) oЗ-ky8lle-m-methylpyriid,

1-Ethyl-3-carbodoyl-4-methyl-6-hydroxypropyl-2-one,

1-ethyl-3-sulfomethyl-methyl-cablamoyl-6-yydroxypyrid-2-one, N-acetoacetyl amine,

· (N-acetolcetylaino) -2-oethoxyoxobenzene-5-sulfonic acid, --УydroxylУinol-2-oe,

1-amino-8-Уyldrxχl77 (fonnlllo) nel0alen-3,6-disulfonic kyselina.a 1-amino-8-L-Уylгoxy 74'-suSlofθnelazo) neltalee 3 _J 6-disulfonic acid,

-1о1по 8-Ьу (1гохХ177) 2 ', 5'-diзuLLfofeelllzo) _nlOtllee-3> 6-dSsu0fenová acid.

vAmines of formula VI

1-Aminobenzene-2-, -3- or -4-betylsulfonyl;

1-Aminobenzene-e-beta-phospholloetylsulone,

- liine-4-methylbenzee-e- ^b -te-sulphonylbutylsulone,

1-Amino-eneen-3-betal-УУlrrtУylsulOon,

1-loino-4-methylbibz-e-b-tetlulfoltolylsulfonic acid, L-a (ei-obenzene-4-betl-sulfatoethylsulfene-2-sulfenoic acid),

-aoin-ben-en-e-bete-sulfulfolylsulphonine-2-sulfonic acid,

1-Aminobenzene - betalSsUL0ltoetУllsulOon-2,4-disulfonic acid,

(1) llinene-10-ethylene-4-beta 'SuS0ltoetУllsullo-,

^amino-2, 5-di-thtxχlenzee-e-te --- lulflltethylsuSfon,

--- -liinobenzen Bethlehem-ssl0ltoettylsuSfon-) ² -klrboxylová acid

-aoinoOen-en-5-betalSuSphatoethylsulfon-2-carboxylic acid,

- lmi-o-2-ethoxybenzene-4-beta-sullltoltУllsuLLloe,

1-amine --- chtorbeneen-44betalSuSphatoethyylsullon,

1- lmineo - øotУtxylУbleele-b-tltsulfllootУylsulOon,

2- aιoinebeftaleb-8-belalSuS0atoltУllsullo-,

2-liinobaftyl-8-beta-sullltolttylsullob-6-sullobic acid,

-aoino-2,5-dioothoxyl-en-4-'-in-lsulfonate, 1-lmino-2-yl: 1-aminobenzene-4-butylsulphonic acid, 1-amino-2,5-diltonoxen-1-en- betl-sulpholoethylsulfon, 1-loino-2-benzoylene-e-ta-8-photoetylsullon,

1-aino-2-bгooOeneen --- vin-lsulOon,

1-Aminoben-en-5-vinylsulphon-2,4-disulfonic acid,

1- (1-methyl-2,4-disulphonic acid), (1-methyl-2,4-disulphonic acid),

1-Amino-ben-en-5-beta-chlorophenylsulfon-2,4-disulfonic acid,

2-Amino-n-: 10alene-8-bela-OosOatoltolylsulfone-6-sulfonic acid,

2-aminonaphthalene-8-vinylsulfone-6-sulfonic acid,

- imino-2-methoxy-5-methyl-b thylbenzeno4 _e taichlooethylsuUloio,

2-Aminophthole-4-4-ethyl: lato-ethylsulfone, 1-bromo-benzoyl-3- or -4-vinylsulfone,

14-amino-2-hydroxy-o-o-ene-0-bbbutylcarbonyl-1-amino-1-olenesulfon-2-sulfonic acid,. 3 '(N - minayУ-β-1-sulfaloethyllulfonylbenzoyl) -1-benzylbenzene,

3- (N-Ethyl-1'-sulfalonthylsullyl-aza) -1-amisobenzene

3-aac-a ^ i ^ ^ IBH 1.Oi ^ t ^ U ^ UO-i ^^^ y ^ * and Mn ^ ^e ^ iC ^ r ^ <^ * ^ mnaoei ^ (^ t ^ enzen.

In the preparation of the preferred dye-based dye-based reactants of the formula I, wherein the D-residue is a sulfo group-containing isobacteria, in particular a mono- or di-dye, carrying a diisobenzoyl, a diisulfonic acid-containing mineral is present. of the solution at low temperature, the dome is carried out at the pH of the acid, at the pH of the solution.

2,4,6-Trifluoro-acetazine of formula (IV) and a dye of formula (V) containing a silane group or, optionally, dye precursors of formula (V) containing sulpho-groups containing the group -N (R 1) H, and imiols of formula (VI) it is preferably carried out in an aqueous solution or suspension, at both low temperature and ulib. the acidic, non-saturated, even pH-lowering of the final binder of formula I remained as fluorine as it was cleaved. residue.

Preferably, the hydrogen fluoride that is released in the condensation is continuously eluted by the addition of aqueous metal hydroxides, metal carbonates, or metal carbohydrates,

If a dye of the formula (I) in which the D isobutyl radical is present by reictivizing the sulfonic acid, the ortho-position to the isocyanate-containing groups, e.g. A compound of the formula I with metals, in which the compounds obtained according to the invention which are present in the ortho-ortho-position for the isogroup of the climate-forming group are referred to before or after the addition of 2. 4,6-Trifluoride of formula IV in relation to p. δiziěly, i0lStУulíiíoi. metal.

Of particular importance are the complexes of the isobutants of formula (I) with the polymer. In addition to the shi t mentioned in the context of the dealkystemic meth, the oxidative sludge mmdd is also used for the preparation of complex compounds with oid.

The dyes of formula (I) are fiber-stiff because they contain fluorine in the rest of the s-tris.

Wavelike-reactive compounds are understood to mean tics which allow for a reaction with hydroxyl groups of cellulose or iminosirapine of naturally occurring polyimides to form spheres of chemical viscosities.

ПеШНуи! birvivi of formula I are new. These birvivi are characterized by high reictivity and coloring and good constancy of ootari. good stability to the world. These dyes have a good fixation capability for a longer time with a high degree of dyeing and a remarkably high color intensity.

In particular, the good tearing power of the red isobutants of the formula I, in particular of the dyes of the formula II, must be avoided by the use of cotton yarn.

.Reeittvoí. The fibers are suitable for dyeing and printing a wide variety of materials, such as silk, leather, wool, superpolyioid fibers, and superiolefin fibers, in particular all of the 1615 fibrous structures that absorb cellulose, such as cellulosic, cellulosic, cellulosic, and cellulose fibers. and especially cotton. These dyes are suitable for both drawing processes and dyeing processes by impregnating the goods to be dyed with aqueous, and optionally also salt-containing dye solutions, and dyes, after treatment with alkali or in the presence of alkali, optionally with heat, fixují.

These dyes are suitable. however, they are also suitable for printing fibers containing d2, such as blended fabrics containing wool, silk or wool.

It is advisable to subject the dyed and tiked articles to a thoroughly cold and hot water, optionally with the addition of dispersing and diffusing non-fixed proportions. The preparation of the monoalcohol compounds as the mmelproducts is not described in all cases in the following examples, since the remaining compounds are readily prepared on the basis of the above.

In the following examples, the parts are intended to be monotonous and temperatures are given in degrees Ccesium.

Example 1

24.5 parts of dye formula

breaks in 400. parts of water to neutral solution. This solution is cooled by the addition of ice at 0 to 5 ° C and 7.1 parts of 2,4,6-trifluoro-1,3,5-triazine are added dropwise at this temperature over 15 minutes, while 2 N sodium hydroxide solution is added simultaneously. maintains the pH of the reaction mixture at 5 to 6.

As soon as the presence of a base substance is no longer detectable, add

14.8 parts of 1-amine-linen-3-bia-8,11-phatoethylsulfone. The pH is maintained between 6 and 6.5 while the hydrogen fluoride released is blunt with 2 N sodium hydroxide solution and the temperature is raised to 20 ° C.

After completion of the reaction, the resulting reactive dye is salted out by addition of sodium chloride, filtered, washed and dried under vacuum. This dye is a yellow powder and dyes cotton and regenerated cellulose in bright, yellow shades.

Dyes with similar properties are obtained when the amino-flavoring agents listed in column 2 of the table below are condensed with equivalent portions of 2,4,6-trifluoro-1,3,5-triazine and simultaneously or thereafter. with the amines listed in column 3 as in Example I.

Table 1

number aminobarvlvo amine color shade on cotton 1 2-aminonaphthalene-1,5-disulfonic acid j 1-amino-3-acetylaminobenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 2 2-aminonaphthalene-1,5-disulfonic acid - * 3-aminophenyl urea 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 3 2-aminonaphthalene-1,5-disulfonic acid ~ * 1-amino-3-hydroxyacetylaminobenzene 1-Aminobenzene-3-beta-phosphatoethylsulfone reddish yellow 4 2-Aminonaphthalene-5,7-disulfonic acid - * 1-Amino-3-acetylaminobenzene 1-Aminobenzene-2-beta-sulfatoethylsulfone reddish yellow 5 2-aminonaphthalene-5,7-disulfonic acid - * 3-aminophenyl urea 1-Aminobenzene-4-beta-sulfoethylsulfone reddish yellow 6 2-aminonaphthalene-4,8-disulfonic acid 1-Amino-3-methylbenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone yellow 7 2-aminonaphthalene-4,8-disulfonic acid - * 1-Amino-3-acetylamino-benzene 1-Aminobenzene-3-beta-sulfatoethylsulfone yellow 8 2-Aminonaphthalene-3,6-disulfonic acid 1-Amino-3-acetylaminobenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 9 2-aminonaphthalene-3,6-disulfonic acid - ^R3- aminofenylmočovina 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 10 2-aminonaphthalene-6,8-disulfonic acid? 1-Amino-3-acetylaminobenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 11 2-aminonaphthalene-6,8-disulfonic acid 1-Amino-2-methoxynaphthalene-6-sulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone Reddish yellow 12 2-aminonaphthalene-3,6,8-trisulfonic acid 1-Amino-3-acetylaminobenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 13 2-aminonaphthalene-3,6,8-trisulfonic acid → 3-aminophenyl urea 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 14 2-aminonaphthalene-3,6,8-tri sulfonic acid? 1-Amino-3-methylbenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 15 Dec 2-aminonaphthalene-4,6,8-trisulfonic acid - » 1-Amino-3-methylbenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone Reddish yellow 16 2-aminonaphthalene-4,6,8-trisulfonic acid? 1-Amino-3-acetylaminobenzene 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 17 1-Aminobenzene-2,5-disulfonic acid - » 1-Aminonaphthalene-6-sulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish yellow 18 1-Aminobenzene-2,5-disulfonic acid - * 1-Aminonaphthalene-6-sulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish brown 19 Dec 1-aminonaphthalene-2,5,7-trisulfonic acid - » 1-aminonaphthalene-6-sulfonic acid -> 1-Aminonaphthalene-8-sulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone violet brown

continued table

number anínobarvivo amine color shade on cotton 20 May 1-aminonartalene-2 _> 5,7-trisulfonic acid -> 1-pyrrino-2,5-dimethylbenzene -> 1-aninonartalene-6-sulfonic acid 1-aminobenzene-3-beta-sulfatoethane t June ^ brown 21 4-Riaazobenoena-3,4 * -disutonic acid - * 1-Amino-naphthalea-6-sulfonic acid 4-aminobenzene-3-. -beta-sulfatoethane buff 22nd 1>4-diaminobenzene-2> 5-disulphonic: 0onová acid -> 1-ethyl-3SS _U tnoiethyl 4-iethyl-6-hydroxy-2-on-5-carboxamide 1-Acido-4-οο1Ηε1benzene-3-be ta-sul- yellow 23 1-Amino-3-acetyl-amino-benzo-a-sulfonic acid - » 1-ethyl-3-butoxyethyl-4-methyl-6-hydroxypyrid-2-one-5-carboxamide 1-aminobenzene-3-beta-sulfatoethylsulfone yellow 24 1-Rmino-3-acetylroinnobenzene-6-sulfonic acid - »1-Ethyl-1H-1-aminocarbonal-4-ol-halo-b-hydroxypyid-2-one 1-aminobenzene-s-buta-atoethane yellow 25 1-pyrrolidin-3-roltylamino-benzyl-6-sulfonic acid 1- (2,5 &apos; -dichloro-4-sulphophenyl) --- olylplrazol-5-one 1-aminobenzene-3-beta-sulfatoethylsulfone yellow 26 1 -aoinoneЗ-acetylroinnobenzene-6-sulfonic acid -> 1- (2> 5 * -Disulfonyl-zinc-pentylpyrazol-5-oa) 1-aminnbenzbn-3 ^^ а-еиПа ^ eth; ^ lsu ^ 11 ^ c ^ a yellow 27 Mar: 1-aoinaoЗ-acetylaoinobenzene-6-sulfonic acid - * 1- (4-Sultotenyl) -3-carboxypyrazol-5-one 1-aminobenzene-3-yl-3-piperidinylsulfone yellow 28 1-Amino-α-Acetylaminobenzylsulfonic acid —J 1- (2-methyl-4-sulf: toflayl-з3-rabboxlplazolazol-5-one ^ О <3 ^ пёп1) 1-Aminobenzene-3-beta-sulfatoethane yellow 29 1-Amino-3-Amino-benzoene-6-sulfonic acid - » 1- (4 *, 8-disultonophthyl-L2 ']) - 3-methylpyrazol-5-one (saponification) 1-Aminobenzene-3- (4-methyl) -sulfone yellow 30 1-a (ninanblazine-2,55-di-sulfonic acid) 1- (3 &apos; -aoinotenyl) -3-methylpyrazol-5-one (from ^ Cd ^) 1-aminobenzin-3-ylmethyl-4-methylsulfone yellow 31 1-Amino-blazine-2,55-disultonic acid; 2-Acetylamino-5-hydroxylartalla-7-sulfonic acid (zinc). 1-Aminobenzene-3-ylbenzyl sulfone orange 32 1-rnboblazlaz2sulfonic acid 2-Amino-hexylarthene-1 H -disutonic acid 1-aminobenzene-3-beta-sulfatoethylsulfone orange 33 2-Aminonaphthalene-1,5-disulfonic acid -> 2-Acetylamino-5-hydroxy-oxartaline-7-sulnonic acid 1-aminobenzene-3-tert-sulfatoethylsulfone orange 34 2 ~ _l 6,8-atninonoftaaLlo- trisutnonove acid - »2 c-e-5-butylamino-7-hydroxJУlartalen sufnonová acid (zmOddenění) 1-aminobenzene-3-beta-sulfatoithylsulfone orange 35 2-a [ninnnaftaalln115 _J 77-trisutnonic acid ->1'-acetyl-4-hydroxy-5-hydroxy] -naphthalla-7-sulfonic acid (reddening) 1-aminobenzene-3-beta- orange 36 1-amino-4-methoxylbenzene-2> 5-disulonic acid- Chinese --------> 2-amino-5-hyddonJyartalln ~ 7- -sulfonic acid 1-aminobenzene-3-methyl-4-methylsulfone šaalatový 37 1-Rmino-4-motoxybblLazla- _2S ulfonic acid -? 2-Amino-5-pyrrolidinyl-7-sulfonic acid 1-aminobenzene-3-yl-4-methyl-ethylene Scarlet 38 1-aminobenzoyl-22-ulphonicone cyanide -> 1- (4'-Nitrobenznylamino) -8-hydroxynatallala-3-di-6-dionic acid (reduction) 1-aminobenzene-3- • beta-sulfatoethylsulfone red

.208117 Continued table No. Amino dye amine color shade on cotton

1-Aminobenzene-2,5-disulfonic acid →

- (3-nitrobenzoylamino) -8-hydroxynaphthalene-4,6-disulfonic acid (reduction)

2-amino-5-aminomethylnaphthalene-1-sulfonic acid -------> 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid

2-aminonaphthalene-1,5-disulfonic acid →

1- (4'-Nitrobenzoylamino) -8-hydroxynaphthalene-3,6-disulfonic acid (reduction)

1-hydroxy-2-aminobenzene-4-sulfonic acid— *

2-Amino-5-hydroxynaphthalene-7-sulfatonic acid (Cu complex)

1-Hydroxy-2-aminobenzene-4,6-disulfonic acid - 2-Amino-5-hydroxy-naphthalene-7-sulfonic acid (Cu complex)

1-hydroxy-2-aminobenzene-4,6-disulfonic acid -> 2-ethylamino-5-hydroxynaphthalene-7-sulfonic acid (Cu complex)

1-hydroxy-2-aminobenzene-4,6-disulfonic acid? 2-Amino-8-hydroxynaphthalene-3,6-disulfonic acid (Cu complex)

1-hydroxy-2-aminobenzene-4,6-disulfonic acid- »1-amino-8-hydroxynaphthalene-3,6-disulfonic acid (Cu-complex)

1-Hydroxy-2-aminobenzene-4,6-disulfonic acid— *

1-Amino-8-hydroxynaphthalene-4,6-disulfonic acid (Cu complex)

1-hydroxy-2-amino-4-acetylaminobenzene-6-sulfonic acid -> 1-amino-8-hydroxynaphthalene-2,4-disulfonic acid (Cu complex)

1-hydroxy-2-amino-6-acetylaminobenzene-4-sulfonic acid -----> 1-amino-8-hydroxynaphthalene-2,4-disulfonic acid, saponification (Cu complex)

1-amino-2-hydroxy-6-nitronaphthalene-4-sulfonic acid ---- »1-amino-8-hydroxynaphthalene-2,4-disulfonic acid, reduction (Cu-complex)

1-amino-2-hydroxy-6-nitronaphthalene-4-sulfonic acid - »1-amino-8-hydroxynaphthalene-2,4,6-trisulfonic acid, reduction (Cu-complex)

2-Amino-1-hydroxynaphthalene-4,8-disulfonic acid - 1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid (Cu complex)

2-aminonaphthalene-4,8-disulfonic acid ->

2-hydroxy-3-aminonaphthalene-5,7-dlsulfonic acid (oxidative introduction of copper)

3 ~ 'methoxy-4-amino-6-methylazobenzen-2 * 5-disulfonic acid ^from -? 2-methylamino-5-hydroxynaphthalene-7-sulfonic acid (copper demethylation feed)

3-Methoxy-4-amino-6-methylazobenzene-2 *, 4'-disulfonic acid -> 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid · (copper demethylation feed)

1-amino-3-acetylaminobenzene-6-sulfonic acid -> 1-amino-8-hydroxy-7- (4'-sulfophenylazo) -naphthalene-3,6-disulfonic acid (saponification)

1-Aminobenzene-3-beta-sulfatoethylsulfone red 1-Aminobenzene-3-beta-sulfatoethylsulfone red 1-Aminobenzene-3-beta-sulfatoethylsulfone red 1-Aminobenzene-3- [beta] -beta-sulfatoethylsulfonyl ruby 1-Aminobenzene-3-beta-chloroethylsulfone ruby 1-amino-4-methoxybenzene-3-tert-sulfetoethylsulfone ruby 1-Aminobenzene-3-beta-sulfatoethiylsulfone ruby 1-amino benzene-3-beta-sulfatoethylsulfone violet 1-Aminobenzene-3-beta-sulfatoethylsulfone violet 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 1-aminobenzene-3-tert-sulfatoethylsulfone blue 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 1-Aminobenzene-3-beta-sulfatoethylsulfone navy blue 1-Aminobenzene-3-beta-sulfatoethylsulfone navy blue 1-Aminobenzene-3-beta-sulfatoethylsulfone navy blue

1-amino-4- (3'-amino-2 *, 4 ', 6'-trimethylphenylamino) anthraquinone-2,5'-disulfonic acid

1-Aminobenzene-3-beta-sulfato-blue continued table

number Amino dye amine color shade on cotton 58 1-amino-4- (2 *, 6'-dimethyl-3'-aminomethylphenylamino) anthraquinone-2,5-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish blue 59 1-Amino-4- (4'-methyl-2'-aminomethylphenylamino) -1-anthraquinone-2,6-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone Reddish blue 60 1-amino-4- (5'-aminophenylamino) anthraquinone-2,2,4'-trisulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 61 1-Amino-4- (4'-aminophenylamino) anthraquinone-2,3'-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 62 1-amino-4- (4'-aminophenylamino) enthraquinone-2,2'-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethyleulfone blue 63 1-Amino-4- (3'-aminophenylamino) anthraquinone-2,4-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 64 1-Amino-4- (2'-methyl-3'-aminophenylamino) anthraquinone-2,5-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 65 1-Amino-4- (2'-methyl-3H-aminophenylamino) anthraquinone-2,6,5-trisulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish blue 66 1-amino-4- (5-aminomethylphenylamino) anthraquinone-2,2,4-trisulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish blue 67 1-Amino-4- (4'-aminocyclohexylamino) anthraquinone-2,6-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone reddish blue 68 1-Amino-4- (4'-aminocyclohexylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 69 1-Amino-4- (3'-amino-4'-methylcyclohexylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 70 1-Amino-4- (3'-amino-2'-methylcyclohexylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 71 1-Amino-4- (4'-amino-3'-methylcyclohexylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 72 1-Amino-4- (4'-aminomethylcyclohexylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 73 1-Amino-4- (3'-aminomethylcyclohexylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulphate thylsulphon-2,4-disulphonic acid blue

continued table

number aminobarVivo amine color shade on cotton 74 1-amino-4- (2 ^of -aminoethylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 75 1-Amino-4- (2'-methylaminoethylamino) -anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfone-2-sulfonic acid blue 76 1-Amino-4- (3'-amino-1-propylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfetoethylsulfone-2-sulfonic acid blue 77 1-Amino-4- (3'-methylamino-1-propylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfonic acid blue 78 1-Amino-4- (4'-amino-1-butylamino) anthraquinone-2-sulfonic acid 1-Aminobenzene-5-beta-sulfatoethylsulfonic acid blue 79 N- (2-carboxy-4-sulfophenyl) -N '- (2'-hydroxy-3'-amino-5'-sulfophenyl) -ms-phenylformazane (Cu complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 80 N- (2-carboxy-5-sulfophenyl) -N '- (2'-hydroxy-3-amino-5 sulfophenyl) -ms-phenylformazan 1-Aminobenzene-3'-beta-sulfatoethylsulfone blue 81 N- (2-carboxy-4-sulfophenyl) -N * - (2'-hydroxy-3'-amino-5-sulfophenyl) -ms- (2-chloro-5-sulfophenyl) formazan (Cu-complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 82 N- (2-carboxy-4-aminophenyl) -N * - (2'-hydroxy-3 *, 5'-disulfophenyl) -ms- (3-sulfophenyl) formazan (Cu-complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 83 N- (2-carboxy-5-sulfophenyl) -N '- (2'-hydroxy-3 *, 5' ') -disulfophenyl) -ms- (3-aminophenyl) formazan (Cu-complex) 1-Aminobenzene-3'-beta-sulfatoethylsulfone greenish blue 84 N- (2-hydroxy-3-amino-5-sulfophenyl) -N '- (2'-hydroxy-4'-sulfophenyl) -ms- (2-sulfophenyl) formazan (Cu-complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone navy blue 85 N- (2-hydroxy-5-sulfophenyl) -N '- (2'-hydroxy-3', 5'-disulfophenyl) -ms- (4''-aminophenyl) formazan (Cu-complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 86 N- (2-hydroxy-5-amino-3-sulfophenyl) -N '- (2', 5-disulfophenyl) -ms-phenylformazan (Cu complex) 1-Aminobenzene-3'-beta-sulfatoethylsulfone blue 87 N- (2-hydroxy-%, 6-disulfophenyl) -N * - (2 *, 4'-disulfophenyl) -ms- (3-aminophenyl) formazan (Cu complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 88 N- (2-hydroxy-4-sulfulfenyl) -N * - (4-amino-2 * -sulfophenyl) -ms- (4'-chloro-3-sulfophenyl) formazan (Cu-complex) 1-Aminobenzene-3-beta-sulfatoethylsulfone blue 89 CuPc- (3) _ - (SO ₃ H) ₂ - SO ₂ NH ₂ __ / ^NH 2 - SO ₂ NH— 1-Aminobenzene-3-beta-sulfatoethylsulfone turquoise blue

Continuation of table number shade of cotton amine dye amine

NiPc- (2)

- · (БОзН) ₂ --so ₂ nh ₂ --so ₂ nh1-eminobenzene-3-beta-sulfatoethylsulfone turquoise blue

CuPc- (3) (SO 4 H 3)

- SO ₂ NH ₂

1-Aminobenzene-3-beta-sulfatoethylsulfone turquoise blue

CuPc- (2)

CuPc- (2)

CuPc- (3)

CuPc- (3)

NiPc- (3)

CuPc- (2)

CuPc- (2)

SO ₂ MH-H ^^ ^nh 2 (SO ₃ H) 2 _} 7 "H (SO ₂ NH) _{1> 3} ^x nh ₂

1-Aminobenzene-3-beta-sulfatoethylsulfone turquoise blue

-— / SO ₃ H

- \ n ₂ nh

- (with ₂ nh

1-Aminobenzene-3-beta-eulfatoethylsulfone turquoise blue

1-Aminobenzene-3-beta-sulfatoethylsulfone turquoise blue

--- (SO ₃ H) ₂

- with ₂ nh ₂

--SO ₂ NH - (SO ₃ H] 3 / H ^H 2 Sat ₂ nh - / / ^SO 3 ^H ) 2.5 (SO ₂ NHCH ₂ CH ₂ NH ₂ Ii _{) 5} (SO ₃ H) ₂ Sat ₂ nh ₂

1-Aminobenzene-3-beta-sulfatoethylsulfone

1-Aminobenzene-3-beta-sulfatoethylsulfone

1-Aminobenzene-3-beta-sulfatoethylsulfone

1-aminobenzene-3-beta-sulfato-ethylsulfone turquoise blue turquoise blue turquoise blue turquoise blue

SO ₂ NHCH ₂ CH ₂ NH ₂

Example 2

To a neutral solution of 30.5 parts · aminoazobarviva trojsoché salts obtained by coupling diazotized 2-aninoiaftaaie-3,6,8-trisullonové acid amide with 3-aiinifenyliiČovinou · environment lefové lctlv ^s acid ⁰⁰ in 5 parts of water to ^{give p} s ^p s teplotč ²⁰ ° C for ^{22 d} ILU ^^ - di-fluoro-6- (4--betr ^from sulfaloethylsulfooylfeoylrilno) -8-triroíou while old age: yM · adding 2 N NaOH pH was kept at 6 to 6.5 .

Condensation is continued until the substance. The resulting dye of the formula can no longer be shown chrommrogrvrically the initiality of the initial

F with high sodium chloride, washed, washed and dried in vacuo. This dye stains the cellulosic materials in very stable reddish-yellow shades.

Dyes of similar proportions are obtained in an analogous manner to that described above for the reactions shown in column 2 of the following table with the primary condensation products of 2,4,6- [1,1'-1,3,5-triamine] and amine which are listed in column 3 as follows:.

Table 2 number aminobbivo condensation product of tr1ljoortiiozanj color shade on cotton

2-amino-1,5-disulfonic acid

------- 1-Amino-3-methylbenzene

2-amino-1,5-disulfonic acid

-------- ^ 1 - ^ o ^ mr ^ c ^ '^; - 3- ^ m ^ liyy-6- ^ m ^ thoxy benzene

2-amino-amino-5- _> 7-disulfonic acid

--- »1-amino-3-methyl bromine

2-Rmolo-amino-4- _> 8-uisulfonic acid —-------> N-methylaminoarnonium

2-rinolorole-4,8-uisulfonic acid

------> 1-N-rthylamin-3-ylbenzene

2-pyrrolidino-3,6,8-trilobloylic acid-- · Ι ^ α ^^^^ θη

2,5-Triazol-2-enoic acid 1-amino-3-methyl-1H-amino-3-methyl-6-methoxy

1 -riino 3 - rcetyli! Linobrnorn-6-carbamic acid sulaonová ---- »1-amide-3-rthyl suj1lmmrhyУ- 4 - methyl-6-hydrlx _{<ypyridin-2-yn-5-krralxyllvé} acid ( oιínmddrnOno 1

1-Aminlnraenzene-4-benzoyl-2-sulfonyl-2-sulfonic acid yellow 1- (2-sulfonic acid) -butan-5-yl-2-sulfonic acid reddish yellow 1-Aminobenzene-1-yl-1-amino-2-sulfonic acid reddish yellow 1-Aminobenzene-S-be-8-methyl-2-sulfonic acid yellow 1-aminobenzene-4-tetramethylsulfonyl-2-carboxylic acid yellow 1-Aminobenzene-5-betylsilylmethylsulphine-2-quartalic acid reddish yellow 1 -rm1nlιarnorn- “2 - ^ - ae- 1 onu reddish yellow Of 1-amino-2-methoxyaenooro-4-barium-sulfonylmethylsulfone yellow

Continuation of the table number

1-Amino-acetylaminobenzene-6-sulfonic acid -----> 1-ethyl-3-aminocarbonyl-4-methyl-

1-Amino-3-acetylaminobenzene-6-sulfonic acid -----> 1- (4'-sulfophenyl) -3-methyl-pyrazol-5-one (saponification)

1-Amino-3-acetylaminobenzene-6-sulfonic acid -----> 1- (5,7-Disulfonaphth-2-yl) -3-

-methylpyrazol-5-one (softening)

1-Aminobenzene-2,4-disulfonic acid - 2-acetylemino-5-hydroxynaphthalene-7-sulfonic acid (saponification)

2-Aminonaphthalene-1,5-di-sulfonic acid 2-Acetylamino-5-hydroxy-naphthalene-7-sulfonic acid (saponification)

1-Aminomethoxybenzene-2-sulfonic acid -> 2-amino-5-hydroxynaphthalene-7-sulfonic acid

2-aminonaphthalene-1,5-disulfonic acid ->

2-ac ethylamino-8-hydroxynaphthalene-6-sulfonic acid (saponification)

1-Aminobenzene-2,4-disulfonic acid - *

1- (4-nitrobenzoylamino) -8-hydroxynaphthalene-3,6-disulfonic acid (reduction)

2-aminonaphthalene-1,5-disulfonic acid— *

1- (4'-nitrobenzoylamino) -8-hydroxynaphthalene-4,6-disulfonic acid (reduction)

1-hydroxy-2-aminobenzene-4,6-disulfonic acid ----- * 2-amino-8-hydroxynaphthalene-6-sulfonic acid (Cu-complex)

1-hydroxy-2-aminobenzene-5-sulfonic acid - 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid (Cu complex)

1-amino-2-hydroxy-6-nitronaphthalene-4-sulfonic acid ------> 1-amino-8-hydroxynaphthalene-2,4-aisulfonic acid (Cu-complex)

1-hydroxy-2-amino-4-acetylaminobenzene-6-sulfonic acid -------> 1-amino-8-hydroxynaphthalene-2,4,6-trisulfonic acid (saponification, Cukomplex)

2-amino-1-methylbenzene-3,5-disulfonic acid ------ »1-amino-2-methoxy-5-methylbenzene

2-amino-5-hydroxynaphthalene-7-sulfonic acid (demethylation of copper)

1-amino-3-acetylaminobenzene-6-sulfonic acid -----> 1-amino-8-hydroxy-7- (phenylazo) naphthalene-Z-6-disulfonic acid (saponification)

1-amino-3-acetylaminobenzene-6-sulfonic acid ------ 1-amino-8-hydroxy-7- (2 *, 5-disulfophenylazo) naphthalene-3,6-disulfonic acid

condensation product from trifluorotriazine color shade on cotton 1-aminobenzene-4-beta-sulfatoethylsulfone yellow 1-aminobenzene-4-beta-sulfatoethylsulfone yellow 1-amino-2-chlorobenzene-4-beta-sulfatoethylsulfone yellow 1-amino-2-methoxybenzene-5-beta-sulfatoethylsulfone orange 1-amino-2-methoxybenzene-5-beta-sulfatoethylsulfone orange 1-Aminobenzene-5-beta-sulfatoethylsulfon-2,4-disulfonic acid scarlet 1-Aminobenzene-4-beta-sulfatoethylsulfone-2-sulfonic acid yellowish red 1-Aminobenzene-4-beta-sulfatoethylsulfone-2-sulfonic acid red 1-Aminobenzene-5-beta-sulfatoethylsulfone-2-sulfonic acid red 1-aminobenzene-2-beta-sulfatoethylsulfone ruby 1-aminobenzene-4-beta-sulfatoethylsulfone violet 1-Aminobenzene-5-beta-sulfatoethylsulfone-2,4-disulfonic acid blue 1-Aminobenzene-4-beta-sulfattoethyl sulfone blue

1-Aminobenzene-5-beta-sulfatoethylsulfone-2-sulfonic acid navy blue 1-Aminobenzene-5-beta-sulfatoethyl8-sulfonic acid navy blue 1-amino-2,5-dimethoxybenzene-4-beta-sulfoethyl sulfone navy blue

Example 3 parts of 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid are dissolved in 400 parts of water to a neutral solution.

The reaction solution is adjusted to pH 4.5 and 7.0 parts of 2,4,6-trifluoro-1,3,5-triazine are added dropwise with good stirring at 0-3 ° C.

The hydrogen fluoride released is neutralized by the metered addition of 2N sodium hydroxide solution. Once no free 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid was detectable, 10.6 parts of 1-aminobenzene-3-beta-sulfatoethylsulfone in 50 parts water were added.

The temperature is allowed to rise to 20 to 25 ° C and the pH of the reaction solution is maintained at 4 to 4.5. Upon completion of the condensation, the dye intermediate is coupled at 0-10 ° C with 15 parts of diazotized 2-aminonaphthalene-1,5-disulfonated acid. At a final pH of 6.5 to 7, the dye of the formula is used

saline, filtered, washed and dried in vacuo. This dye is obtained in the form of a dark red powder and dyes cotton and regenerated cellulose in bluish red tones with good wet fastness, good abrasion fastness and good light fastness.

Diazo components whose coupling energy is sufficient for coupling in the range of 4 to 5.5 can be coupled to the primary condensation product of the coupling component and 2,4,6-trifluoro-1,3,5-triazine, followed by the final step reaction with an amine.

The following Table 3 contains additional dyes obtained by reacting 2,4,6-trifluoro-1,3,5-triazine with the coupling components listed in column 2, then with the amines listed in column 3, and finally coupling with the diazo components listed in column 4 .

Table 3

number coupling component amine diazosložka color shade for fun 1 1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid 1-Aminobenzene-3-beta-sulfatoethylsulfone 1-Aminobenzene-2-sulfonic acid Red 2 1-Amino-8-hydroxynaphthalene-4,6-disulfonic acid 1-Aminobenzene-3-beta-phosphatoethylsulfone 1-Aminobenzene-2-sulfonic acid red 3 1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid 2-aminonaphthalene-8-beta-sulfatoethylsulfone 1-Amino-4-carboxybenzene-2-sulfonic acid red 4 1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid 1-Aminobenzene-4-beta-sulfatoethylsulfone 1-Amino-4-methylbenzene-2-sulfonic acid red

Continuation of the table Number Coupling Amine Diazo component Color shade on cotton

1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid

1-Aminobenzene-3-beta-sulfatoethylsulfone

1-Aminobenzene-2,5-disulfonic acid red

1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid

2-Aminonaphthalen-8-beta-sulfatoethylsulfon-6-sulfonic acid

2-Aminonaphthalene-1-sulfonic acid red

1-Amino-8-hydroxynaphthalene-4,6-disulfonic acid

1-Aminobenzene-3-beta-sulfaethylthio sulfone

2-aminonaphthalene-1,5-disulfonic acid

Red

1-Amino-8-hydroxynaphthalene-6-sulfonic acid

1-Aminobenzene-3-beta-sulfathenethylsulfone

2-Aminonaphthalene-1,5,7-trisulfonic acid to

Example 1 a d 4

26.8 parts of 1,4-diaminobenzene-2,5-disulfonic acid are dissolved in 250 parts of water with the addition of sodium hydroxide to a neutral solution.

After addition of 2.8 g of medium sodium phosphate, 13.6 parts of 2,4,6-trifluoro-1,3,5-triazine are added dropwise at 0 ° C over 5 minutes while maintaining the pH of the reaction mixture by adding 2 N hydroxide solution. sodium at 6.

After completion of the condensation, a solution of 28 parts of 1-aminobenzophen-3-beta-sulfatoethylsulfone in 100 parts of water is added and the pH is maintained at 6.5 by dropwise addition of 2 N sodium hydroxide solution.

The temperature is gradually raised to 20 ° C. 7 parts of solid sodium nitrite are then added and after complete dissolution, the reaction mixture is poured into a mixture of 25 parts by volume of 10 N hydrochloric acid and 100 parts of crushed ice.

The now neutralized solution of 1-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyrld-2-one-5-carboxylic acid amide in 100 parts of water is poured into the diazotization solution so obtained, the pH is adjusted to 6.5 and at this pH the reaction mixture was stirred _(until coupling is complete.

Addition of sodium chloride to the reaction mixture precipitates the dye of the formula

SO ₂ CH ₂ CH ₂ OSO ₃ H and then isolated. After drying and grinding, an orange dye powder is obtained which dyes cotton from the water bath in intense color, slightly reddish yellow shades.

If, after completion of the condensation of 2,4,6-trifluoro-1,3,5-triazine with 1,4-diaminobenzene-2,5-disulfonic acid, the amine listed above is used instead of 1-aminobenzene-3-beta-sulfatoethylenesulfone in the following Table 4, instead of the 1-ethyl-3-sulfomethyl-4-methyl-6-hydraxypyrid-2-one-5-carboxylic acid amide of said coupling components, then other valuable dyes are obtained which give these shades on cellulose fibers.

Dyes with similar properties but with more hypo-enormous shades on cellulose fibers are obtained when 1,3-diaminobenzene-4,6-disulfonic acid is used in place of 1,4-diaminobenzene-2,5-disulfonic acid.

Table 4 number amine coupling component color shade on cotton

1 1-Aminobenzene-3-beta-sulfatoethylsulfone 1- (4 ' -sulfonyl) -1-3-methyl r-ol of 5-one yellow 2 1-Aminobenzene-3-beta-sulfatoethylsulfone 1- (2 ', 5'-dichloro-4 ^from -sulfofenyl) -3-methylpyrazole-5-one Yellow 3 1-Aminobenzene-3-beta-phosphatoethylsulfone 1- (2 ', 5'-dichloro-4'-sulfophenyl) -3-methylpyrazol-5-one yellow 4 1-Aminobenzene-3-beta-sulfatoethylsulfone 1- (4 ^Z, 8'-disulfonaphth-2'-yl) -3-methylpyrazole-5-one reddish yellow 5 1-Aminobenzene-3-beta-sulfatoethylsulfone 1-ethyl-3-aminocarbonyl-4-methyl-6-hydroxypyrid-2-one reddish yellow 6 1-Aminobenzene-3-beta-sulfatoethylsulfone 4-Amino-3,5-disulfoacetacetic anhydride Yellow 7 1-Aminobenzene-3-beta-chloroethylsulfone 1-hydroxynaphthalene-4-sulfonic acid bluish red 8 3- (N-methyl-beta-sulfatoethylsulfonylamino) -1-aminobenzene 1-hydroxynaphthalene-4,6-disulfonic acid red 9 1-Aminobenzene-3-beta-sulfatoethylsulfonic acid 2-hydroxynaphthalene-6-sulfonic acid red 10 3- (N-ethyl-beta-sulfatoethylsulfonylamino) -1-aminobenzene 2-hydroxynaphthalene-3,6-disulfonic acid red 11 1-Aminobenzene-3-beta-sulfatoethylsulfone 2-Acetylamino-5-hydroxynaphthalene-7-sulfonic acid scarlet 12 1-Aminobenzene-3-beta-sulfatoethylsulfone 1-Asylamino-5-hydroxynaphthalene-7-sulfonic acid red 13 1-Aminobenzene-3-beta-sulfatoethylsulfone 1-ac ethylamino-8-hydroxynaphthalene-3,6-disulfonic acid bluish red 14 1-Aminobenzene-3-beta-sulfatoethylsulfone 1-Benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid red

color shade on cotton continuation table

Number amine coupling component

15 Dec 1-Aminonaphthalene-4-beta-sulfatoethyl sulfone 1-Benzoylamino-8-hydroxynaphthalene-4, 6-disulfonic acid red 16 1-Aminobenzene-3-beta-sulfonylphenyl sulfone 2-ac ethylamino-8-hydroxynaphthalene-6-sulfonic acid red

1-Aminobenzene-3-beta-sulfatoethylsulfone

reddish blue

1-Aminobenzene-3-beta-sulfatoethylsulfone

blue

1-Aminobenzene-3-beta-sulfatoethylsulfone

red

1-Aminobenzene-3-beta-sulfatoethylsulfone

Scarlet

21 3-beta-sulfatoethylsulfonylamino-1-aminobenzene 1-hydroxynaphthalene-4,6-disulfonic acid red

Example 5

51.5 parts of aminophenylnaphthriazole of formula

is dissolved in 900 parts of water at pH 5. 13.6 parts of 2,4,6-trifluoro-1,3,5-triazine are added dropwise at 0 ° C and the pH is kept constant by the addition of 2 N sodium hydroxide solution. .

After completion of the reaction, a solution of 7 parts of sodium nitrite in 50 parts of water was added to the reaction mixture, and the reaction mixture was poured into a mixture of 25 parts by volume of 10 N hydrochloric acid and 100 parts of crushed ice.

After one hour, excess nitrous acid, if any, is decomposed by addition of amidosulfonic acid. 25.4 parts of 1- (4'-sulfophenyl) -3-methylpyrazol-5-one are added to the diazo suspension thus obtained and the pH is maintained at 5 by the addition of 2N sodium hydroxide solution.

After coupling, 28 parts of 1-eminobenzene-3-beta-sulfatoethylsulfone in 100 parts of water were added. The pH is maintained at 6.5 and the temperature is allowed to slowly rise to 20 ° C.

After completion of the reaction, the dye of the formula is isolated by salting out and filtering

NH

HO ₃ SOCH ₂ CH ₂ O ₂ S

This dye is, after drying, a yellow-orange powder which dissolves in water to a yellow color solution and dyes cotton in yellow tints.

In an analogous manner to that described in Example 5, the dyes listed in Table 5 are obtained when the compounds of column 2 are diazotized after treatment with the reactive component and reacted with the coupling component of column 3 and then condensed with an amine which is shown in column 4.

color shade on cotton

Table 5 Number Diazo Component Coupling Amine Component

1- (2'-chlorophenyl) -1-methylpyrazol-5-one

1- (4'-Sulfophenyl) -3-carboxypyrazol-5-one

1- (2'-Methyl-4-sulfophenyl) -3-methylpyrazol-5-one

1- (2 ', 5'-Dichloro-4-sulfophenyl) -3-methylpyrazol-5-one - (6'-chloro-3-sulfophenyl) -3-methylpyrazol-5-one

1- (3'-sulfamoylphenyl) -3-methylpyrazol-5-one

1-Aminobenzene-3-beta-phosphatoethylsulfone yellow

1-Aminobenzene-3-beta-sulfatoethylsulfone Yellow

1-Aminobenzene-3-beta-sulfatoethylsulfone yellow

1-Aminobenzene-3-beta-sulfatoethylsulfone yellow

1-Aminobenzene-3-beta-sulfatoethylsulfone yellow

1-aminobenzene-3-beta-sulfatoethylsulfone yellow continued table

Number diazo component coupling component amine color shade 'on cotton

1- (2'-chloro-4-sulfophenyl) -3-methylpyrazol-5-one

1- (6-sulfonaphth-2-yl) -3-methylpyrazol-5-one

1- (3'-Sulfophenyl) -3-ethyl-5-aminopyrazole barbituric acid

2-hydroxy-4-carboxypyrid-6-one

1-Ethyl-3-aminocarbonyl-4-methyl-6-hydroxypyrid-2-one

1-Aminobenzene-3-beta-sulfatoethylsulfone yellow

1-Aminobenzene-3-beta-sulfatoethylsulfone yellow

-aminobenzane-3-beta-sulfatoethylsulfone yellow

1-Aminobenzene-3-beta-8-sulfa- yellow toethylsulfone

1-Aminobenzene-3-beta-sulfatoethylsulfone yellow

1-aminobenzene-3-beta-sulfatoethylsulfone yellow continued table

number diazosložka, coupling component amine color shade on cotton 13 2-amino-5-amino-ethyl-phthalene-1-sulfonic acid 1- (4-O-4-methyl-4-methylpiperazin-5-one) 1-amiaobeazea- tltoethylsuls fon yellow 14 2-amino-5-aminooethanaphthaline-15-sulfonic acid 1-Ethyl-3-sulfamethyl-4-methyl-2-hydroxyhydroxypyridyls-2-carboxylic amide 1-Amino-benzoan-3-t-bis-sulsteto-ethylsulfone yellow 15 Dec ^{2-AMIA-5-α-aminomeahyla>} tllea-1s "sulfonic kyBělini 1-Beazoyf amino-8-hydroxy-yiaf tefea-4, dsdisultosic acid 1-liabnazea-З-НеН ^ аtoethyleulfone red 16 2-Amino-5-amino-thylaaphthalene-1-sulfonic acid 1-acetylamino-8-hydroxybutyl-3,6-di-pulse. phonic acid- 1-Aminobenzoyl ethylsuls fon red

EXAMPLE 6 28.1 parts of 1-amino-benzene-4-beta-sulfatoethyl8-fluorone are dissolved in 200 parts of water at pH 5. 3.5striazine and adding 2 N solution. Sodium hydroxide must ensure that the pH value does not exceed 5 ·

After completion of the condensation, a solution of 21 parts of 1,3sdiaminobenzene-4-sulfonic acid sodium salt is added to the mono-mono-solvate solution obtained. Condensation is carried out at pH 5 until the presence of the diamine is no longer detectable and the temperature is allowed to rise to 20 ° C.

The product still containing the diazotable aminosapine is now diazotized in an analogous manner to that described in Example 4. 40.5 parts of 1-acetylamino-8-1H-pyrooxyaatalene-3,6-disulfonic acid disodium salt are added to the dnazosfouan solution and then the coupling is carried out at pH 6 to 6.5. By adding potassium chloride · the dye of the formula is precipitated,

SO ₂ CH ₂ CH ₂ OSO ₃ H is isolated and higher. This dye is a red powder that dyes cotton in brilliant red shades.

In a similar way. can be produced diaTŠ dyes according to the invention, when _{2,4,6-trifluoro-1,3-t} 5-triazine in analogy to the - above-described workflow is condensed first with the amine in column 2 uvedenýfa then with diaminobenzenaulfonovou acid which is shown in column 3 of the following table 6.

If the secondary condensation product thus obtained is diazotized and co-sawed with the coupling component in the column: &lt; tb &gt; 4, then reactive dyes are obtained. which dyees cotton in the shades specified in column 5, stable in light and wet.

Ta b ulka '6 number amine diam inobenzenesulfonic acid copying component color shade on cotton 1 1-Aminobenzene-4-beta-eulfatoethylsulfoo 1,3-diamino-benzene-4-sulfonic acid 1- (3'-Sulfenyl) --- methylpyrazol-5-one yellow 2 1-Aminobenzene-4- [beta] -sulfatoethylsulfoa 1,3-diaminobenzene-4-sulfonic acid 1- (3'-Sulloleoyl) -3-methyl-5-amino-pyrazole yellow 3 1-eminobenzene-4-beta-sulfatoethylsulfone 1,3-dieminobenzene-4-sulfonic acid> 1- (2 ', 5'-dichloro-4'-sulfophenyl) -3-methylpiperazin-4-one yellow 4 1-Aminobenzene-4-beta-sulfatoethylsulfoa Ί, 3-diaminobenzene-4-sulfonic acid 1- (5 ', 7'-Disulfonyl-4'-yl) -3-methylpayazol-5-one yellow 5 1-aminobenzene-4-tert-sulfatoethylsulfone 1,3-dieminobenzene-4-sulfonic acid amide 1-et-hyl- ^ 3 ^ - ^ i ^ ^ l ^ t ^ <^ m ^ ^th; ^ L-4'-o--metthrl hydroaqrppyid - ^ - one ^ -carboxylic acid yellow 6 1-Aminobenzene-4-beta-sulfatoethylsulfoa 1,3-diaminobenzene-4-sulfonic acid 2-Aminonaflaaene-6-sulphonic acid orange 7 1-Aminobenzene-4-beta-sulfatoethylsulfone 1,3-diamiaobenzene-4-8 sulfonic acid 1'-aminonaffalene-1,7-disulfonic acid orange 8 1-Aminobenzene-4-beta-sulfatoethylsulfoa 1,3-diaminobenzene-4-8 sulfonic acid 2-N-methoxyl-8-hydroxy] -phenyl-6-sulfonic acid orange 9 1-Aminobenzene-4-beta-sulfatoethylsulfoa 1,3-diamiaobenzea-4-sulfonic acid 2-Hydroxyphthalene-3,6-disulfonic acid scarlet 10 1-Aminobenzene-4-beta-sulfatoethylsulfoa 1,3-diminobenzene-4-sulfonic acid 2-Acyl-amino-5-hydroxy-phenyl-phthalene-7-sulfonic acid orange 11 1-Aminobromo-4-beta-sulfatoethylsulfone 1,3-diaminobenzene-4-sulfonic acid 1-Benzylamino-8-hydroxy-thienyl-3,6-disulfonic acid red 12 1-Aminobenzenesen-4-beta-sulfatoethylsulfone 1,3-diaminobenzene-4-sulfonic acid 1-tert-ethyl-8-hydroxylphenyl-4,6-disulfonic acid red 13 1-Aminobenzene-4-beta-sulfatoethylsulfone 1,4-diamiaobeaza-3-sulfonic acid 1- (2'-Methyl-4 ') sulfonyl) -3-carboxypyrazol-5-one yellow 14 1-Aminobenzene-4-beta-sulfatoethylsulfone 1,4-dieminobenzene-3-sulfonic acid 1- (2'-Chloro-5'-s-3-oxo-5-one) -3-methylpyridine-5-one yellow

The dyeing procedure with 1 part of the dye obtained according to Example 1 was dissolved in 100 parts of water by the addition of 0.5 parts of sodium salt of m-nitrolesulfonic acid.

The obtained rosookra te impregnates the cotton fabric so that its weight increases by 75. % and then ee deletes.

Then ae fabric impregnated with a solution which contains 1 lira, 5g of sodium hydroxide and ³⁰⁰ g of sodium chloride and the temperature is ^ Z fibrillation ² 0 ° C, squeezed to 75% hmoonoosní. přírd ^ ek, then vytervená ttantaa steamed for 3 s ° sekun ^dp temperature of 100-101 ° R breaths is washed for 15 minutes in a 0.3% boiling solution of a non-ionic detergent, rinsed. and dried.

Dye Regulation II.

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

This solution was added to 1900 DILIA cold water PMDA 60 parts of sodium chloride and ^D l of dyeing ^and crops were introduced ¹⁰⁰ says ^profiles cotton fabric.

^ zvýW fence at ⁴⁰ ° C after 3 přičmž ⁰ minutes add ⁴⁰ kalclnovan Dih ^{s y} sod and again ⁶⁰ says ^profiles brine. ^ fence kept at ⁴⁰ ° C for 3 ⁰ Tobu о1пиО setkanina vyoáchá- and then steamed for 15 minutes in a 0.3% boiling solution of a non-ionic detergent, followed vyoáchá and dried.

Claims (13)

SUBJECT OF THE INVENTION A process for the production of reactive binders of the general formula I (I) wherein: D denotes the rest of a series of mono- or polyazo dyes, metal-containing azo-dye complexes, anthraquinone dyes, phthalocyarnine dyes, foazazan dyes, azommthin dyes, nitroaryl dyes, dioxazine dyes, phenazine dyes or stibbin dyes,. containing sulfo groups, R 1 is hydrogen or C 1 -C 4 alkyl, R ₂ represents hydrogen, mm ethyl group or ethyl group, X is a radical of formula -SO ₂ CH ₂ CH ₂ Cl, -SO ₂ CH = CH ₂ , -SO ₂ CH ₂ CH ₂ OSO ₂ H, -вО ₂ СН 2СН ₂ 0РОзН or -N (R ₃ ) SO ₂ CH ₂ CH ₂ OSO ₃ H and \ R @ 1 represents hydrogen, methyl or ethyl, and the benzene or naphtha ring may contain, in addition to X, C1 -C4 alkyl, C1 -C4 alkoxy, halogen such as fluorine, chlorine and bromine, nitro , hydroxy, carboxy, and the like, or metal complexes thereof, characterized in that 2,4,6-trifluoro-s-triazine of formula IV (II) is condensed. F sulfo-containing organic dye of formula V D-NH R in which D and R 6 are as defined above, or a pre-product of an organic dye of formula V containing sulfo groups and an amine of formula VI (VI) wherein " Rg and X are as hereinbefore defined, in any order, to the reactive dye of formula I, and if dye precursors are used, these are converted to the desired dyes of formula I and the reactive dyes obtained are optionally treated with heavy metal reagents. 2. A process according to claim 1, wherein the starting material is a sulfo group containing an organic dye of the formula V in which D is a mono- or disazo dye residue or that the diazo components and / or the coupling components are present. the -NtRpH group, the condensation with the 2,4,6-trifluorotriazium of the formula IV, and then, or after further condensation with the amine of the formula VI, completes the preparation of the dye by curing with each other, optionally with certain mono- or disazo dye components. 3. The process according to claim 2, wherein the starting material is a sulfo group, an organic dye of formula V wherein R @ 1 is hydrogen, methyl or ethyl, and amines of formula VI, wherein R 8 and R 8 are hydrogen atoms. 4. The process according to item 3 ', for the preparation of reactive dyes of the general formula II OH NH wherein the remainder of the benzene or naphthalene residue, number 1 or 2, (II) X n is 0 or 1 and p is 0 or 1, wherein the benzene or naphthalene radical A and the benzene radical B may contain a C 1 -C 4 asylum group, a C 1 -C 4 alkyl group, a halogen such as fluorine, chlorine and bromo, n-tro, hydroxy, diethoxy and sulfo a X - is as defined in formula (I) and is characterized in that the coupling and condensation in the reaction sequence is a reaction of the diazinated amine compound of formula (VII) in mutual reaction A-NH2 (VII) coupling component of formula VIII (VIII) 2,4,6-s-t-triazine of formula IV and amine of formula IX X (IX) to form a reactive dye of formula II. 5. A process according to item 1 - for the preparation of reactive dyes of the general formula I, in which D is a dye residue of a series of mono- or poly-dyes, metal-containing dyes, anthraquinone dyes, phthalocino amine dyes, iotnazane dyes, azomer. Inorganic dyes, nitroaryl dyes, d-oxazin dyes, phenysine (> dyes or stilbene dyes containing sulfo groups), consisting of two or more than two components, characterized in that the dye component of formula V containing the -NH group, in the 2,4,6-t-fluoro-s-triazine of the formula IV and the amine of the formula VI condense and left in the process step; react with another component or alternatively other dye components of formula V to form a reactive dye of formula I. 6. A process according to claim 5, characterized in that condensation product containing the -NH group is condensed with the 2,4,6-trifluoro-8-triazole of formula IV, the obtained condensation product is diazotized and coupled to a coupling reaction. and before or after it is reacted with an amine of formula VI. 7. A method according to claim 5, characterized in that the co-component is:. contains the group -NH, condenses with 2,4,6-trilloor-s-triazine of formula IV and - to the thus obtained R product - the diazotized diazo component is coupled and before or after the reaction with an amine of formula VI. 8. The method of claim 5, displacing in that the diazo component which contains an NH group is condensed with 2,4,6-s-trlfluor triazieem Formula IV, the longer the coupling component, which, ^R 1 contains a -NH condensation of 2,4,6-trifluoro-s-thiizzine of formula IV, and the condensation product of the diazo component is diazotized and the coupling component is coupled to the condensation product and before or after it is coupled. reacts with an amine of formula VI. 9. The process of claim 1, wherein the organic dyes of the formula (V) containing a sulio group and containing in the residue D another group -NH, tondene. with the corresponding ^R roiož- Community and 2,4-trilΊlor ₁ 6-s-triazin formula IV so mooekuly dyes to introduce two or more than two s-triazinoíé residues. 10. A process according to claim 4 for producing a reactive composition of formula II, wherein the diazrtic amino acid of formula VII is blended with a coupling component of formula VIIa to form a compound of formula X (X) which is The 2,4,6-trifluoro-1,3,5-triazine of the formula IV and the primary condensation product obtained with the amine of the formula IX. 11. A process according to claim 4 for the preparation of a dye of the formula II, characterized in that the coupling component of the formula VVII is condensed with the 2,4,6-Ш-ЮЮ-Z, S-triazine of the formula IV. is condensed with an amine of formula IX and the resulting secondary product is coupled with a diazotized amino compound of formula VII. , 12. The process of Claim 4 wherein the dye of formula (II) is a coupling component of formula (VII). is condensed with 2,4,6-triflurr-1, _5-d З trinzieem formula IV to the obtained primary condensation product was coupled hedged diaza-amino compound of formula VII and izoelolUeiiin obtained is condensed with an amine of formula IX. 13. The method of claim 11 for producing the reactive dye of the formula III (III) íyzniiulící in that the one-8-Imiimi Uydrrxyn _ltilni-3> 6-disuldonríé acid condensed with ty1aiurlllrridem, the primary condensation product is condensed with 1- For example, the diazotized 2-O-1-pent-1,5-disulfonic acid is coupled to the secondary condensation product obtained.