CS195317B2 - Process for preparing dyes reactive with fibres - Google Patents

Abstract

Fibre-reactive dyes of formula <IMAGE> wherein D is the radical of an organic dye containing sulpho groups, R1, R2 and R3 independently of one another are hydrogen or alkyl having 1 to 4 carbon atoms, B is an alkylene or arylene radical and A is an optionally substituted amino group are prepared by condensing an organic dye, containing sulpho groups, of formula <IMAGE> 2,4,6-trichloro-1,3,5-triazine, an alkylenediamine or arylenediamine of formula <IMAGE> 2,4,6-trifluoro-1,3,5-triazine and a compound of formula H-A (8> to give a fibre-reactive dye of formula (1) or, if D is the radical of an azo dye containing sulpho groups, starting, not from an organic dye of formula (4) containing sulpho groups, but instead from the corresponding diazo component and coupling component and the other above-mentioned starting materials. The dyes prepared are distinguished by high reactivity and are particularly suitable for dyeing cotton by the exhaustion dyeing method.

Description

The present invention relates to fiber-reactive dyes of the formula I

D-N-C 1 -C -N-B-NR 10 O 2 b Ϊ, b wherein D is a radical of an organic dye containing sulfo groups, R 1, R 2 and R 3 independently of one another are hydrogen or alkyl of 1 to 4 carbon atoms,

Is a C 2 -C 6 alkylene or phenyl radical which may be substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, carboxyl, sulfo or halogen, naphthyl radical which may be substituted sulfo or a diphenylurea, diphenyloxetane, stilbene or diphenylethane residue which may be substituted by a sulfo group; and

A is amino, hydroxylamino, hydrazino which may be substituted by phenyl or sulfophenyl, C 1 -C 4 alkylamino which may be substituted by hydroxyl, such as chlorine or phenyl, N, N-C 1 -C 4 alkyl-alkylamino, which may be substituted with hydroxyl, Alkoxyalkylamino having 1 to 4 carbon atoms and alkyl y.alkoxylu, ^{cyclohexylamino,;} morpholino, piperidino, piperazino, N-alkyl-N-phenylanyl having 1 to about 2 carbon atoms in alkyl, N-sulfomethyl-N-thenylamino, phenylamino, which may be substituted with C 1 -C 4 alkyl, C 1 alkoxy up to 4 carbon atoms, halogen, sulfo, sulfomethyl or carboxy, naphthylamino which may be substituted by sulfo, C1-C6 alkoxy, C1-C4alkoxy in each of -alkoxy or C1-C4alkylthio; carbon atoms.

Particularly, the radical D is a sulfo-containing dye, namely monoazo or polyazoan dyes, metalcoin-complex series, formazan series, anthraquinone series, phthalocyanine series, stilbene series, oxazine series, dioxazine series, dioxenyl series, triphenylmethane series, nitro radicals or azac series. . For R 1, R 2, R 5 as C 1 -C 4 alkyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl are suitable.

The radical V is an alkylene radical having 2 to 6 carbon atoms or, in particular, a benzene, naphthalene, diphenyl or stilbene radical. The arylene radical V may contain further substituents, for example alkyls such as methyl, ethyl and propyl, alkoxy groups such as methoxy and ethoxy, carboxy and sulfo groups and halogen atoms such as fluorine, chlorine and bromine. Suitable for the residue A are, for example, amino groups -NH2, hydroxylamino, hydrazino, phenylhydrazino, sulfophenylhydrazino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, n-3-methoxyethylamino, diethyl, • a group, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, β-chloroethylamino, β-hydroxyethylamino, γ-hydroxypropylamino, benzylamino, cyclohexylamino, morpholino, piperidino, piperazino and in particular aromatic amino groups, such as aromatic amine; , toluidino, xylidino, chloroanilino, anisidino, phenetidino, 2-, 3- and 4-sulfoanilino, 2,5 disulfoanilino, sulfomethylanilino, N-sulfomethylanilino, 3- and 4-carboxyphenylamino, 2-carboxyphenylamino, 2-carboxy -carboxy-4-sulfophenylamino groups α, 4-sulfo-1-naphthylamino, 3,6-disulfo-1-naphthylamino, 3,6,8-trisulfo-1-naphthylamino and 4,6,8-trisulfo-1-naphthylamino; such as alkoxy, methoxy, ethoxy, propyloxy, isopropyloxy, butyl oxy, (S-methoxyethoxy), (3-ethoxyethoxy, γ-methoxypropoxy, γ-ethoxypropoxy, alkyl, β-propoxypropoxy), γ-propoxypropoxy).

Preferred are reactive dyes of formula I wherein D is a sulfo group-containing organic dye residue, R1, R2 and R5 are hydrogen atoms, W is an arylene residue containing at least one sulfo group, and A is amino.

The amino group in A here and in the following description not only refers to the N-group, but also a substituted amino group, for example methylamino, diethylamino, β-hydroxyethylamino, phenylamino, sulfophenylamino, naphthylamino or also cyclic amino, for example piperidino or morpholino.

In particular, the present invention relates to reactive dyes of the formula I wherein D is a sulfo-containing azo dye, R 1, R 2 and R 3 are hydrogen, W is a phenylene radical containing one or two sulfo groups and A is an amino group.

Of the reactive dyes of the formula I which contain a sulfo-containing azo dye residue, those dyes of particular interest are those wherein D is the sulfo-containing azo dye residue of the H-acid and J-acid series; R 1, R 2 and R 3 are independently hydrogen or alkyl; 1 to 4 carbon atoms, V is a sulfophenylene residue and A is an amino group.

An important group is the reactive dyes of formula II.

wherein Di is the remainder of the diazo component of the benzene or naphthalene series and A is an amino group.

Preferred dyes of formula II are reactive dyes of formula III

Since the dyes of formula I contain two cleavable halogen atoms Cl and F, they are twice reactive with the fibers.

By fiber reactive compounds is meant those compounds which can react with the cellulose hydroxyl groups or the amino groups of natural or synthetic polyamides to form a covalent chemical bond.

The process for preparing the reactive dyes of the formula I is characterized in that in any order simultaneously or in individual steps an organic dye containing sulfo groups or dye components of the formula IV is condensed together: •; D — NH. (IV),

R1. · Where D and Ri are as defined above,

2,4,8-trichloro-1,3,5-triazine of formula V

. an alkylenediamine or arylenediamine of Formula VI

NH — B — NH

I I

R2 R6 (VI), wherein R2, R3 and В are as defined above,

2,4,6-Trifluoro-1,3,5-triazine of formula VII | II, and a compound of formula VIII

H — A. . . (VIII), wherein A is as defined above:.

Since the individual process steps can be carried out in different order, or partially also simultaneously, different process variants are possible.

. The starting materials used for each partial reaction are derived from formula (I). The reaction is carried out in successive stages, the order of the individual condensations between the individual reaction components of formulas IV to VIII being freely selectable.

Preferred compounds of formulas IV to VIII are those wherein D is a sulfo-containing organic dye residue, R1, R2 and R3 are hydrogen atoms, W is an arylene residue containing at least one sulfo group, and A is amino.

A preferred method of carrying out the process for preparing the reactive dyes of the formula I is characterized in that it is as follows: starting compounds of formulas IV-VIII will use compounds wherein D is a sulfo-containing azo dye residue, R 1, R 2 and R 5 are hydrogen atoms, W is a phenylene residue containing one or two sulfo groups, and A is an amino group.

In particular: compounds of the formulas IV to VIII are used as starting compounds of the formulas IV to VIII, wherein D is the azo dye residue containing sulfo groups of a series of H-acids or J-acids; Ri, ^R2 and R3 are independently hydrogen atoms or alkyl groups having from · 1 to 4 carbon atoms, В is a sulfophenyl radical and A is amino.

According to one variation of the above-described process, reactive dyes of formula I wherein D is. a sulfo group-containing organic dye residue composed of two or more than two components may be prepared by reacting components with the remainder D, which together contain at least one sulfo group, one of which contains an NHR 1 group, wherein R 1 has a as defined in formula (I), 2,4,6-trichloro-1,3,5-triazine. Formula V or alkylenediamine arylendiamin of 'vozrce.VI wherein R2, Rs а В are as defined in formula ¹ of the formula I,

2,4,6-trifluoro-1,3,5-triazine of formula VII and a compound of formula VIII, wherein A is as defined in general formula I, to give. reactive dyes. I.

Examples of organic dyes composed of two or more than two components are: multazo dyes, disazo dyes. trisazo dyes, - triazazo dyes, metal-complex dyes, formazan d.

. The above-described variation of the process is of particular importance for the preparation of the reactive dyes of the general formula I, wherein. D is. azo dye residue containing: sulfo groups. In these dyes, the portion of the azo dye residue to which the chloro-s-triazine residue is directly bound can be either the diazo component or the coupling component. Thereby, two variants of the above described are possible: variations of the method. Both of these process variants for preparing reactive dyes of the general formula. I, wherein D is a sulfo group-containing azo dye residue, is characterized in that it is:. .

( ^a ) a diazizable aromatic diamine containing an HNR 1 group; wherein R 1 is as defined for Formula I, a coupling component, wherein the diazable aromatic diamine and the coupling component together comprise at least one sulfo group,

2,4,6-triichloro: R, 3,5-triazine of formula V, alkylenediamine or arylendiamine of formula VI, wherein R2, R5 and V are as defined for formula I, 2,4,6-trifluoro-1,3, 5-triazine of formula VII and a compound of formula VIII, wherein A is as defined for formula I, are left; react together

7.

azqtací ,. by coupling, and by condensation. to form a reactive dye of formula (I); _·:. ,

(b) coupling component; which it contains. 'HNR 1', wherein R 1 'is as defined above. in the general formula. A diazotable aromatic amine, wherein the coupling component and the diazotable aromatic amine together contain at least one sulfo group, namely, 5-tichloro-5-thiazine of formula (V), alkylenediamine or arylendiamine of formula (VI) wherein: . R 2, R 5 and B are as defined for formula (I); . 2,4,6-riflurrtl, 3, S-triazine of formula VII and a compound of formula VIII wherein A is as defined for formula I are reacted together by diazotization, coupling and condensation to form a reactive · Dyes of the general formula I.

A preferred method for carrying out both process variants a) and b) is characterized in that the starting compounds are used. a diazotizable aromatic diamine comprising an HNR 1 group wherein R 1 is a hydrogen atom, a coupling component, wherein the diazotable diamine and the coupling component together contain at least one sulfo group, 2,4,6- trichloro-1,3,5-triazine of formula V; an arylendiamine of formula VI wherein R 2 and R 5 are hydrogen atoms and B is a phenylene moiety containing. exceed 'diva one or sulfo, 2,4,6-tri- fluoro-1,3 _l 5-triazine of formula VII and · a compound of formula VIII wherein A is amtnoskupina ·, or ·' compounds are used as starting coupling component, wherein the coupling component and the diazotable aromatic amine contain together at least one sulfo group, 2,4,6-trichloro-1, wherein the coupling component and the diazotable aromatic amine contain at least one sulfo group , 3,5-triazine of formula V, an arylendiamine of formula VI where R 2 and R 3 are atoms. Hydrogen A &quot; B &quot; is a phenylene residue containing one or two sulfo groups, 2,4,6-trifluoro-T, 3,5-triazine of formula VII and a compound of formula VIII wherein A is amino. ..

A further preferred embodiment consists in using H-acids or 'J-acids containing HNR 1' as the starting compounds, wherein R 1 is hydrogen or alkyl of 1 to 4 atoms. carbon, diazotizable aromatic amine, 2,4,6-a-1,1,5-1,3,5-1г-1β of formula V, an arylendiamine of formula VI, wherein R2 and R3 are independently hydrogen or alkyl of 1 to 4 carbon atoms and B is a sulfophenylene radical, 2,4,6- (1,3,5-triazine) of formula (VII) and a compound of formula (VIII) wherein A is amino .

The above-described variants a) and b) for the preparation of reactive dyes of the general formula I, wherein D is a sulfo-group-containing azo dye residue, comprising individually several embodiments, for example:

1. The amine-containing coupling component is condensed with cyanuric chloride, the primary condensation product obtained is condensed with alkylenediamine or arylendiamine, the secondary condensation product is coupled with a diazocomponent, and the obtained azo compound is condensed with cyanurchloride and thus obtained. · The condensation product will eventually. condenses with · amine.

2. Proceed according to paragraph 1 to. in the preparation of the azo compound. Further, the cyanuric chloride is condensed with an amine (alcohol or alkyl mercaptan) and the resulting primary condensation product is condensed with the above azo compound.

3. Proceed according to paragraph 1 until the secondary · condensation product of cyanuric chloride, a coupling component containing an amino group and an alkylenediamine · or · arylenediamine, is · condensed with cyanuric chloride, the resulting condensation product is condensed again with an amine , and the finally obtained condensation product is coupled to a diazo component.

4. The amine-containing coupling component is condensed with cyanuric chloride, the primary condensation product is coupled with a diazo component and the azo compound is condensed with an alkylenediamine or an arylendiamine. The resulting condensation product is condensed with cyanurofluoride and the condensation product is condensed with an amine.

5. The diazompomenta is coupled with the coupling component. The azo compound thus prepared, which contains an amino group in the remainder of the coupling component, is condensed with cyanuric chloride and the primary condensation product is further condensed with an alkylenediamine or an arylendiamine. The secondary condensation product obtained is condensed with cyanurfluoride and the resulting condensation product is condensed with an amine.

Instead of the condensation of the secondary condensation product of the cyanurtortoride azo compound and alkylenediamine or of the arylendiamine with cyanurfluoride and then with the amine (alcohol, phenol, alkylmercaptan or arylmercaptan), the primary condensation product from cyanurfluoride and (alcohol or alkyl mercaptan) and condensed with the above secondary condensation product of a cyanuric chloride and a compound and an alkylenediamine or an arylendiamine.

6. The amine (alcohol or alkyl mercaptan) is condensed with cyanurofluoride the primary condensation product is condensed with alkylenediamine or arylendiamine and the resulting secondary condensation product is condensed with cyanuric chloride. Furthermore, by coupling the palladocomponent with the coupling component, an azo compound is prepared which contains the amino group in the remainder of the diazo component or in the remainder of the coupling component The azo compound is condensed with the intermediate described above.

This procedure is generally applicable, ie also for dyes of all other classes, using any

Mrw® .йьйймЖ - šUfšMPWr. - where the bawivói OsaU is. aminoskuMňú.,

4. (Шфё! That according to § 6 to dt> for the preparation of the intermediate from / amine · (alkanol or alkyl mercaptan), cyanurfluoride, alkylenediamine or arylendiamine and cyanuric chloride, this intermediate is condensed with the / co-coupling component which contains an amino group and couples with a condensation product containing a diazocomponent.

8. Proceed according to /. 6 to dio preparation of the secondary condensation product from an amine (alcohol or alkyl mercaptan), cyanurofluoride and an alkylenediamine or arylenediamine. In addition, an azo compound containing an amino group in the remainder of the diazo component or in the remainder of the coupling component is prepared by coupling the diazo component with the coupling component and the azo compound is condensed with cyanuric chloride. The primary condensation product thus formed is condensed. with the above-described secondary. kobduMační · 'business'.,.'

Also.' -this · postip ·· -. In general, it can be used, and can be arbitrarily matched. The sulfo group containing an amino group with cyanuric chloride and the resulting primary condensation product is condensed with a secondary condensation product of an amine (alcohol or alkylpiperptan), a cyanurofluoride and an alkylenediamine or an arylendiapine.

Following the ninth PE .podle.oidštavice · · 6 to UO (preparation of secondary 'Kon ^ d ^ e ^ r ^ 2 ^ ic ^ fi ^^ ^i} of the product · · amine (or alcohol · • -ňlkylmerkapíá-' nu) and cyanuric fluoride 'alkylenediamines or arylendiaminu. Furthermore condensed cyanuric chloride with a coupling component which contains an amino group, the resulting primary condensation product is condensed with the stated amount' undiluted secondary condenser. produktem- and coupled ^with! last resulting kon • deeiwŘní® product of diazocomponents.

IQ. It proceeds according to paragraph 6 until preparation of the intermediate from amine (alcohol or alkyl mercaptan), cyanurofluoride, alkylenediamine or arylendiamine and 'cyanur0111' (01¾), this intermediate is unilaterally condensed with a diazo component which, in addition to the amino group contains an additional amino group, the resulting condensation product is diasterelated and coupled with the coupling component.

According to the procedure of paragraph I, reactive dyes of the general formula II are obtained by condensing 2,4,6-trichloo-1,3,5-triazine of the formula V with an H-acid of the formula IX

and phenylenediamine sulfonic acid of formula X

the resulting secondary condensation product of formula XI,

with ul coupled with a diazotized amine of> MZOrĎ.Xll;

(XIU, where

Di-j® residue of diazocomponent,. the benzene or naphthalene series obtained by the azo compound of formula XIII

where.

As defined above, 'condenses with: -' 2,4,6-trifluoro-1,3,5-triazine - formulas

VII 'and' the obtained 'condensation' product are condensed with a compound of formula VIII wherein A is an amino group to form a reactive dye of formula II.

wherein Di and A are as defined above.

Valuable reactive dyes of formula III are obtained analogously by condensing 2,4,6-trichloro-1,3,5-triazine of formula V with the H-acid of formula IX obtained. -. the primary condensation product is - condensed with a phenylenediamine-aminoullonic acid of formula X, - the obtained secondary condensation product is coupled with a diazotized aminobenzenesullonic acid of formula XIV; · · '·. Wi

SC ^ H .....

the resulting azo compound is condensed with 2,4,6-trilluoro-1,3,5-triazine in the form of VII.a and the residue is condensed with amino benzene. -lonic acid - of formula XIV). to form a reactive dye of the formula. . .- - ·. <· '. . '··. ·

As starting materials for the preparation of the reactive dyes of the formula I, the following may be mentioned:

(a) organic dyes containing compounds of the formula IV.

Monoazo compounds of formula XV

where

Di is at most a dicyclic aryl radical not containing -azosups and -NHR, R is hydrogen or alkyl, and the -NHR is bonded to the naltalene ring, preferably at the 5, 6, 7 or 8 position, and which may contain a sullo group at position 5 or 6 of the naltalene core.

D 1 may be a residue of a naltalene or benzene series which contains no azo substituents, for example a stilbene residue, a dilenyl residue, a benzthlazolyllenyl residue or a dilenylamine residue. Also useful in this class are dyes which - - - NHR - are bonded to the naltalene nucleus at the benzoylamino or anilino group which is bonded to the naltalene at the 5, 6, 7 or 8 position.

Particularly valuable are the starting dyes in which - D 1 is sullonated lenyl or naphthyl, particularly where the SO 2 H group is in the O-position, to the bond; the -lenyl moiety may be further substituted, for example, by halogen atoms such as chlorine, alkyls such as methyl, acylamino, such as acetylamino, and alkoxy groups such as methoxy.

2. Disazo compounds of formula XV, wherein Di is a residue of an azobenzene, azonaltalene or lenylazonaltalene series and the naltalene nucleus may be substituted with a -NHR- and optionally a sullo group as in class 1.

3. Monoazo compounds of formula XVI

D, -nO ~ NHR _(X in,

1 · 9 3: 3'Γ7 where -у. ·. ·· .... ·:. . ·.

Di is at most d-cyclic. aryl residue described in class · 1. a .s. advantage . a disulfonaphthyl- or N-stilbene radical, R 1 is an atom ^; hydrogen or alkyl and the benzene nucleus may contain additional substituents such as. are halogen atoms or alkyls, alkoxy groups. carboxyls, ureido-α-acylamino groups.

4. Monoazo compounds. or a disazo compound of the formula. XVII.

H — N — Di — N = N — K

.... 1 · • '' R ·· ': ·. · '·.

(XVII) where.

Di is an arylene residue, as is. Yippee . the rest-azobenzene, azonaphthalene. or phenylazpnaphthalene series; or p. advantage. a dicyclic arylene residue of benzene or naphthalene. and K is the naphtholsulfonic acid residue - or. the remainder of the enolized or enollable ketomethylene compound (such as acetacetyl acetyl or 5-pyrazolone). with OH. an o-position to, an azo group, and a. R is. hydrogen or alkyl. Di is preferably a residue. benzene. - which contains. sulfo. .

5. Monoazo or disazo compounds of Formula XVIII

Di - N = N - Ki - NHR '(XVIII),

Di is the residue listed above for Di. in class 1 and 2 and Ki is the enolyzable ketomethylene moiety. compounds (such as acetoacetarylide or 5-ipprazolone) with an OH group. in the o-position to the azo group.

6. Metal-complex compounds, for example copper, chromium complexes. and cobalt, dyes of the above formulas XV to XVIII, wherein Di, K and Ki are as defined above and at the o-position to the azo group in Di is. further. a metalisable group (e.g., hydroxyl, low molecular weight alkoxy or carboxyl).

Examples·

In class 1:

α-amtao-1-hydroxy-2- (2‘-sulfophenylazo) -naphthalene-3-sulfonic acid,

6-mlthalamino-1-hydroxy-2- (4‘-acetyla · ml.no-2‘-sulfophenrlazo) -naphthalene-3-

-sulfonic acid, α-amino-1-hydroxy-2- (2'-sulfophenylazo) -naphthaler-3,6: -disulfonic acid; - ..

8-Amino-1-lyoxoxr-2- (4‘-chloro-2‘-ol)

-sulfo-phenollazol-11a-alpha-3,5-cdisulfonic acid. 'acid, ’·, ··

7mm.in2-2- (R) - disulfophenylazo) -1-. . -droxynaphthalene-3-sulfonic acid,

7- mlth71amin2-2- (2‘-sulphenyenylazo) -1-

-hydroxyinaphthalene-4-sulfonic acid, γ-methylamino-4- (4‘-methoxy-2‘-sulfo-).

phenol-17-yl-1-hydroxynaphthalene-3-sulfonic acid,. . - ..

8- (3 &apos; -7 &apos; -IN-benzoylamino) -1-hydroxy-.

-2- ⁽² -šulfofenylazo) -nffaatrn 3,6-Pisulfonová acid ;.

7-amino-1'-trans-2,2,2'-azone-7'-thiophen-Γ, 3,5 ', 6-tetrasulphonic acid, 8-amino-1-lyloxy oxy- ⁴ -azoriaphthalene-14,4-trisulfonic acid. acid,.

7-Amino-1,1'-dimethyl-2,2,2'-azonaphthalene-Γ, 3,5‘-trisulfonic acid;

6- mttlr17min.o-1-lydroxy-2,2‘-7zon7fta- ..

only Γ, 3,5 ‘.-risulfonic acid,

7-Amino-1-hydroxy-4-azonaphthalene-

-T, 3-disulfone. acid. ..

8-Amino-1-hydroxy-2- ( ⁴ -hydroxy-B4):.

6-Amino-naphthalm 3, 6-cis-sulfonic acid, 6-a ^. Mino-1-hydroxy-2- (4'-hydroxy-4-carbonyloxyphenylazo) -naphthalene-3,5-disulfonic acid. _:: in class: 2 :,

8-Amino-1-hydroxy-2- [4'- (2'-sulfophenylazo) -2'-methoxy-5'-methylphenylazo] -naphthalene-S-disulfonic acid 8-amino-1-heroin-2- [4 '- (4'-Methoxylenyl-17zo) -2'-carbonylphenylazone-7-phthalene-3,6-disulfonic acid,. .

8-Amiiro-1-hydroxy-2- [4 '- (2' -hydroxy-3 ', 6' - disulfo-1'-naphthalene) -2'-carboxyphenyl-azo-naphthalene-β-disulfonic acid acid,. ,

4,4 ' -bis- (8 ' -7mino-1 &apos; -hydroxy-3 &apos;, 6 &apos; -disulfo-2 &apos; -naltrlazo) -3,3 &apos; -dimethoxydiltnyl and 6 &apos; [4 '- (2 "-sulfof phenylazo) -2' - '5'-methoxy-méthrll ^| enrl7zo] -naltaltri-3,5-disullonová acid class 3:.,

2- (4‘-Amino-2‘-methylenenylazo-naphthalene-4,8-disulfonic acid),

2- (4‘-amino-2--acetylaminophenylazo) -.....

4-nitro-4'- (4'-methylaminophenyl) -2-nitro-5,7-disullonic acid, 4-nitro-4'- (4'-7imino- 2'-methil-5'-imethoxy-phenylazo) istilbene-2,2'-disulfonic acid, 4-amino-4 '- (4'-methoxylenrza-stilbene-2,2'-disullonic acid), 4-amino-12'-methylazobenzene2', 5 Disulfoic acid, in class 4:

1- (2 ‘, 5‘-dichloro-4‘-sulfophenyl) --- methyl

-4- 'razolone,

1- (4'-Sulfonylphenyl) -4- (4'-amino-2'-sulfophenyl) -5-pyrazole,

1- (2'-Methyl-1,5'-oxo)

- (4 "-aminb 2 ~ ^'J súlf0fenylazpJ S-pyrazolone,

1- (г'-аайо етау ^! .Beta.-methyl-D- (3 '-amift0: -6' - ^ 5 ^t sulfoTeHyiazoj U5 ^ * AA / OW, 4-amino-4 '(3 "' - methyl -l '''phenyl' - 4 ^<, '' pyrazol-5 '-one lazo) -5ШЬеп-2,2'- disulfonic acid,

4-Amino-4 (2'-hydroxy-3 '', 6 '' - disulfol '' - naphthylazo) -stilbene-2,2'-disulfonyl-4'-acetylamtation-1-hydroxy-2 '- ( Sodium-S * -sulfonylphenylazole-Thiattaien-S.E.

7- (3 ' -sulfophenylamino) -1-trans-2- (4 &apos; -amino-2 &apos; -kaloxythienyl) naphthalene-3-sulfonic acid;

84-phenylaitroph-1-hydroxy-2 '- (4''ЩЩ1ПО-2'-cй1- phenyenylazo) -naphthalene-5'-aisulphonic acid, N-acetylamino-4'-hydroxy-6'-amino-2'-sulfonophenyloxy 'íiattaltal ^ ^ -3 -3 kyselina kyselina kyselina kyselina kyselina kyselina kyselina, in class 5:

1- (3‘-aminophenyl) -3-methyl-4- (2‘, 5‘-longphenylphenylazo) -5-pyrazolone,

1- (3'-amlnof) -3-carboxy-4- (2'-k &j>carboxy-4'-sulfophenylazo.) - 5-pyrazolone, 4-amlttó M3 ^ ^ ^ yM THAT ⁴ 4 ^^ " · -Disulf ofenylazo) -1 * '> рута ^ р1-5 “-onyl] -stilbene-žMlsůifQWůá kу $ ейпа, <1- (3'-anftphthiophenyl) -3Nka ^ bóWťi': - [4 ' и (к '*'; ^ й18ййо5 £ е® ^ г0,) у;

-2 ‘^. Те.1Ьоху-5 *‘ - те1ЬуЙе ^ ур у azo] -5-pychinone, in class 8:

inědirs complex of _{3-amino-X-hydrpk.y:} 2- (2'-5'-říydroxy. s'CiitPřen'ylažo) -naphthalene-3,6 d.išulfonovůu..kyselíhpii ^j,. Copper complex with 6-amino-1-hydroxy-2-

- (2'-hydroxy-5'-sulfof phenylazo) naphthalene-3-sulfonic acid, copper complex of 6-L-aminp-hydrpxy-2- ^{(2'-hydroxy-5-naphthalen} -sulfůřenylazoj - ^, W Disulfonic acid.

Copper complex with 8-amino-1-hydroxy-2-

- (2'-Hydroxy-3'-chloro-5'-sulfophenylazo) 4-naphthyl-3'-hydroxy-2'-hydroxy-2 (2'-hydroxy-2'-hydroxy-2 ') ^ šuttofenylazó) -naphthalene-d-3-naphthalen'sulfottoVOu acid copper complex with s-amino-l-hydroxy-44H z • (2 ^': _{dsulfofenyiazoj?} "2'-5'-methóííý. methylphenol ^phenylazo: Methyl-3,6-dimethylformic acid, copper complex with 6-amino-1-hydroxy-2-

- [4'- (2 ', 5'-disulfophenylazo) -4' - methoxy-5'-methylphenylazolnaphthalene-3,5-disulfonic acid, copper complex with 1- (3'-amino-4'-sulfonylphenyl) -3-methyl-4- [4 '- (2' ', 5' '- disulfenyenylazoj-2'-methoxy-5'-methylphenylazo] -5-pyrazolone, copper complex with 7- (4'-amino- 3'-sulfoanilino) -1-hydroxy-2- [4 '- (2' ', 5' '- disulphenylenyl) -2'-methyl-5'-methylphenylazep'-raththalene-5-sulfonic acid, copper complex with 6- (4-Amino-34-sulfonolino) -1-hydroxy, 2- (3'-carboxy-phenyl) -1-naphthalene-5-sulfonoyl acid, 1: 2-chromium complex with 7-amino-6 '- nitro- The sulfonic acid is used as the hydrohydroxybenzoic acid.

1: 2-chromium complex with 6-amino-1-hydroxy-2- (2'-carboxy-phenylazo-1-naphthalene-2-sulfonic acid),

1: 2-chromium complex of 8-an-inpTl-hydroxy-2- (4 ^{<2'-nitro-phenylazo)} -naítáleů 3,6-disulfonpyo.u acid.

l: 2-cobalt complex of 6- (4'-amipp-3'-sulphonic oanilino) -l-hydroxy-2- (5 ^{"-chloro-2-hydroxyphenyl} phenylazo) -naphthalene-3-tnlen sulfpnpvou acid, L 2-chromium complex with 1- (3'-amino-4'-sulfophenyl-3-methyl-4- (2'-hydroxy-4'-sulfo-1'-naphthylazo) -5-pyrazolone, 1: 2-chromium complex with 7- (4'-sulfoanilino) -1-hydroxy-2- (4''-amino-2'-carboxyphenylazo) -naphthalph-3-sluric acid, 1: 2; (3'-aminophenyl) -3-methyl-4- [4 ' ^, 4'-nitro-2 ^, carboxyphenylazo) -5-pyrazolone.

Especially important azo dyes that can be used in. The preparation of reactive barium compounds of formula I are azo dyes of the formulas

198317 s

fsOjHb-з

К ': ^; (XX), - (^ Оз ^ Ь-з)

(HO _d S) _f . ₃

H; NH-acyl

22.1- (SQ3H) 0-3. . , '·

CH 2; NH-acyl

4;

N - N

(XX1) where K is a residue of a coupling component of a benzene, naphthalene or heterocyclic series, acyl is an aliphatic acyl residue containing up to 3 carbon atoms or an aroma?

tic radical having not more than 8 carbon atoms and R is as defined for formula I uvedený- and metallized azo dyes of formulas. '· · ^· -

(XXI) r

..?. ·

III-O-Cu-O

O ť

γι

Ri

NHq '(or NH-acyl) / (XXIII), wherein R 1 and acyl are as defined in formulas XIX, XX and XXI, and Me is Cu, Cr or Co.

7. Anthraquinone compounds which contain a group of the formula —NHR, wherein R is a hydrogen atom or an alkyl bonded to an alkylamino group or an arylamino group which is itself bound at the α-position of the anthraquinone core, in particular a compound of formula XXIV

NHR key-U

NH-Z-NHR wherein the anthraquinone core may have one additional sulfo group at the 5, 6, 7 or 8 position and Z 'is a bridging member which is preferably a divalent benzene moiety, for example phenylene, diphenylene or 4,4'-stilbene, or azobenzene. Preferably, the substituent Z měl should contain one sulfo group for each benzene ring.

Examples:

1-amino-4- (4'-aminoanilino) anthraquinone-2,3'-disulfonic acid and the corresponding 2,3'-5-, 2,3 ', 6- and 2,3', 7-trisulfonic acid, 1-amino-4- (4'-amino-4'-benzoylaminoanilino) anthraquinone-2,3'-disulfonic acid and the corresponding -2,3 ', 5-trisulfonic acid.

(XXIV), 1-amino-4- [4'- (4''-aminophenylazo-anilino) -anthraquinone-2,2 ', 5-trisulfonic acid, 1-amino-4,4'-amino - (3'-carboxyanilino-anthraquinone-2,5-disulfonic acid, 1-amino-4- (3'-aminoanilino-anthraquinone-2,4 ', 5-trisulfonic acid and the corresponding 2,4'-dlsulfonic acid) acid, 1-amino-4- [4'- (4'-aminophenyl) -anilino] -antraquinone-2,3 ', 5-risulfonic acid, 1-amino-4- (4'-methylamino) -anilinoantra-. quinone-2,3'-disulfonic acid and the corresponding 2,3 ', 5-trisulfonic acid, 1-amino-4- (4'-n-butylamino) anilinoanthraquinone-2,3'-disulfonic acid, 1-amino -4- (4'-methylymino-5-carboxyanilino) anthraquinone-2-sulfonic acid, 1-amino-4- (3 '- / 3-hydroxyethylamino-anilinoanthraquinone-2,5-disulfonic acid),

1- (4‘-Aminoanilino) anthraquinone-2,3‘-disulfonic acid, a.

1-Amino-4- (4 amino-amino-2 methoxy-methoxyaniilno) anthraquinone-2,3 dis-disulfonic acid.

8. Phthalocyanine compounds of the formula .XXV ^ ^β0 2 ^- (χχν)

FC · wherein Fc is a phthalocyanine core, preferably phthalocyanine medium, ω. is -OH. and / or -NH 2, Z ‘is a bridging member, preferably aliphatic,. a cycloaliphatic or aromatic bridge - and n: and m are 1, -2 or -3 and may be the same or different provided that n + m is not more than 4.

Phthalocyanine series dyes which are used in the process of the present invention. of the invention, are preferably metal phthalocyanines, such as copper phthalocyanines, which - contain at least one water-solubility-causing group, such as a sulfo group, and at least one group of the formula --NHR where -R is - a hydrogen atom or an alkyl, or the groups may be bonded to the benzene rings of the phthalocyanine core directly or via a divalent bridge, for example via bridges such as -phenylene-, -CO-phenylene-, -SO2- phenylene-, -NH-phenylene-, -S-phenylene-, - O-phenylene-, -CH2S-phenylene-, -CH2O-phenylene-,

-CH2-e.nylene-, -SCH2-enylene-, -SO2CH2-phenylene-, -SO2NR1-enylene-, -CH2-, -SO2NRiiarylene-, -NRiC0-phenylene-, -NRiSO2-phenylene-, -SO2O -tenylene-, -CH2NR-phenylene-, -CH2N HC O-thenylene-, -SO2NR1-alkylene-, -CHaNR1-ayylene-, -CONRienylene-, -CONRiarylene-, -SO2-- or -CO-. - - ··

In said divalent bridges means. R 1 is hydrogen, alkyl or cycloalkyl, arene is a divalent aromatic radical, optionally substituted with, for example, a halogen atom, an alkyl- or alkoxy, wherein the terminal bonds may be bonded to the same or different nucleus and the alkylene is a divalent aliphatic radical; the chain - containing heteroatoms such as nitrogen, for example the radical -CH 2 CH 2 -NH-CH 2 CH 2 -. '

Examples of such divalent aromatic residues - Labeled. such as arylenes are: aromatic nuclei, for example benzene nucleus, naphthalene nucleus, acridine nucleus and carbazole nucleus, which may contain additional substituents and radicals of formula XXVI;

СЭ "° ίχχ ^VT) from wherein the benzene ring may comprise - further substituents - and -D is a bridging group such as -CH = CH-, -NH-, -S-, -0-, -SO2-, -Ν0 = Ν-, -N = N- N-, -NH-CO-NH-CO-NH, -O-CH 2 CH 2 -O- or Formula XXVII

N ~ —N

J. У (XXVII),

Examples

3- (3'-aarilno-4'-sulfophenyl) -cyclohexyl-Cuftalocyanine-tri-3-sulfonic acid, di- (4-3'-amino-4'-sulephenyl) - sulfamylCuetalocyanine-di-4-sueonic acid,

3- (3‘-Aminophenyl) amino-3-sulfonylamino-4-amino-4-N- (4-amino-3-sulfonylphenyl) sulfonamide; trisulfonic acid;

Co-phthalocyanine-4,4‘-di-N- (4‘-amino-4‘-sulphenyl) carboxamld-4,, 4 ‘- -dicarboxylic acid and

Cu-4- (4‘-amines-3‘-sulfobenzoyl) -phthalocyanine.

. Mixtures of phthalocyanines may also be used, for example a mixture of approximately equal parts of Cu-phthalocyanine-N- (4-amino-3-sulfophenyl) sulfonamide trisulfonic acid and Cu-phthalocyanine-di-N- (4-amino-3-sulfophene). enyl) -sulfonamide disulfonic acid.

9. Nitrobar of formula XXVIII 'Z | OzN — D — N — Q (XXVIII) wherein D is a naphthalene or benzene ring which may be further substituted, the nitrogen atom N is in the o-position to the nitro group, Z is a hydrogen atom or an optionally substituted hydrocarbon residue and Q is a hydrogen atom or an organic moiety bonded to a nitrogen atom through a carbon atom and wherein Q and Z are not both hydrogen atoms and Q is bonded to Z when Z is a hydrocarbon moiety, or to D at the o-position to the nitrogen atom to form a heterocyclic ring and containing at least one group of formula -NHR, wherein R is hydrogen or alkyl; in particular, nitro-dyes of formula XXIX

V — NH — B — NHR

N02. . (XXIX), where V and V is a monocyclic aryl core and the nitro group in V is in the o-position to the NH-group.

Example d

4-Amino-2'-nitrodiphenylamine-3,4'-disulfonic acid.

9. Metalocomplex Farmazan dye of formula XXX ··· ‘

4 1 -NH

where Q is an organic, nitro or cyano radical, A and V are diazo compounds of the benzene, naphthalene or heterocyclic series and Y 1 and Y 2 are always attached at the o-position to the azo group and are substituents this meaning. In particular, the radical Q is a benzene series radical such as phenyl or sulphophenyl or a low molecular weight alkyl radical such as methyl, a low molecular weight alkoxy group, a low molecular weight, preferably 1 to 4 carbon atom containing carbalkoxy, benzzoyl or heterocyclic radical. phenyl radicals substituted with sulfonamido or alkylsulfonyl. The substituents Y1 and Y2 are, in particular, hydroxy and carboxyskiipines. Suitable heavy metals are copper, chromium, cobalt and nickel.

Examples of copper complex with 2'-carboxy-2'-hydroxy-3'-amino-1,3,5-triphenylformazan-4 ', 5', 3'-trisulfonic acid, copper complex with 2 ', 2'-dihydroxy -3'-amino-5'-теигу15иИопу1-1,3,54г11епу1-3 ", 5", 4 "'- trisulfonic acid, copper complex with 2'-carboxy-4'-amino-2" -hydroxy-1, 3,5-trifenylfOrmazan-3 ", 5", 2 "'- trisulfonic acid copper complex 2 ^<-hydroxy-2" -carboxy-4''- amino <no-l, 3,5-trifenylformazan-4' 4 &apos; -disulfonic acid, copper complex with 2 &apos;, 2 &apos; -dilodoxy-5 &apos; -amino-. -1,5-diphenyl-3-methylformazan-5 *; 3'-disulfonic acid, copper complex with 2 *, 2'-dihydroxy-5'-amino · -1,3,5-triphenylformazan-3 ', 3 ", 5" -trisulfonic acid, copper complex with 2'-carboxy-3'-amino-2 "-hydroxy-3"'(1"-phenyl-3" - methylpyrazol-5 "- onyl-4 "" -Azo) -1,3,5-triphenylformazan-3 ", 5", 2 "", 5 "" - tetrasulphonic acid, 2 ', 2 "-dicarboxy-1,5-diphenyl-1-3-nickel complex (т-ат1поЬепгоу1) -1-methyl-4 ', 4'-disulfonic acid. '

b) 2,4,6-Trichloro-1,3,5-triazine of formula V (cyanuric chloride)

c) Alkylenediamines and arylendlamines of formula VI: ethylenediamine, n-propylenediamine, n-butylenediamine, 1-methyl-n-propylenediamine, n-hexylenediamine,

1.3- diaminobenzetn,

1,4- diaminobenzene,

1,3-diamino-4-chlorobenzene,

1,3-diamino-4-methylbenzene,

1,3-diamino-4-methoxybenzene,

2,6-diaminonaphthalene-4,8-disulfonic acid,

1,4-Diamlnobenzene-2-sulfonic acid

1,4-diaminobenzene-2,5-disulfonic acid, 1,3'-diaminobenzene-4-sulfonic acid, 1,4-diaminobenzene-2-carboxylic acid,

1,3-diamine-benzene-4-carboxylic acid,

1,4-dianlino-2-methylbenzene,

4,4'-2,2-dláminódifenylureidiO ^<-disulf tin acid, 4,4'-dlatoinodifenyloxyethan 2.2%-disulfonic acid, 4,4'-diaminostilbene-2,2'-disulfonic acid, 4,4'- diaminodiphenylethane-2,2'-disulfonic acid.

d) 2,4,6-Trifluoro-l, 3,5-triazine of formula VII (cyanuric fluoride), * ¹ '; · '

e) Compounds of formula VIII

1. Amines:

ammonia, hydroxylamine, hydrazine, phenylhydrazine, sulfophenylhydrazinyl, methylamine, ethylamine, propylamino, isopropylamine, butylamine, .beta.-3-methoxyethylamine, n-methoxypropylamine, N, N-dimethylamine, Ν, Ν-diethylamine _; N-methyl-N-phenylamine, N-ethyl-N-phenylaniine, benzylamine, cyclhoxyxylamine, morpholine. · ..

piperidine, aniline, toluidine, xylldine, chloraniline, anisidine, phenetidine, sulfanilic acid, metanilic acid, aminobenzylsulfonic acid, aniline-hethanesulfonic acid,. m-aminobenzoic acid, p-aminobenzoic acid,

2-amino-4-sulfobenzoic acid,

2-amino-5-sulfobenzoic acid, 1-naphthylamino-4-sulfonic acid.

2. Alcohols methanol, ethanol, propanol, isopropanol, butanol, pentanol, hexanol, β-methoxyethanol, β-ethoxyethanol,

3. Alkylmercaptans methylmercaptan, ethylmercaptan.

Diazotatable aromatic amines and coupling compounds which can be used in the above-described variations of processes a) and b) for preparing the reactive dyes of formula I wherein D is a sulfo group-containing azo dye residue include:

Diazokomponenty:

aniline, o-, p- and p-toluidines, o-, m- and p-anisidines, o-, m- and p-chloroanilines,

2,5-dichloroaniline, α- and N-naphthylamine,

2.5- dimethylaniline,

5-nitro-2-a ^; mÍňoanispl,

4-aminodiphenyl, aniline-2,3- and 4-carboxylic acid,

2-aininodiphenylether,

2-, 3- or 4-aminobenzenesulfonamide, or -sulfomonomethyl- or -ethylamides or sulfonidimethyl- or -sulfondiethylamides, dehydrothio-p-toluidine monosulfonic acid or dehydrothi0- p -toluidine sulfonic acid, anilin-2-, -3- and -4- sulfonic acid, aniline-2,5-disulfonic acid,

2,4-dimethylaniline-6-sulfonic acid,

3-amine.obenaptrifluoride-4-sulfonic acid,

4-chloro-5-methylaniline-2-sulfonic acid.

acid,

5-chloro-4-methylaniline-2-sulfonic acid,

3-acetylaminoaniline-6-sulfonic acid,

4-Acetylaminoaniline-2-sulfonic acid, 4-chloroaniline-2-sulfonic acid, S.alpha.-dichloroaniline-4-sulfonic acid alcohol, 4-methylaniline-2-sulfanoic acid,

3-methylaniline-6-sulfonic acid;

2,4-dimethoxyaniline-6-sulfonic acid,

4-Methoxyaniline-2-sulfonic acid, and 5-methoxyaniline-2-sulfonic acid,. N, S-dichloro-amino-α-sulfonic acid, 2-naphthylamine-4,8- and -6,8-disulphonic acid, 1-naphthylamine-2-, -4-, -5-, -6- or -7-monosulfonic acid,

1-naphthylamine-3,6-disulfonic acid,

2-naphthylamine-3,6- and -5,7-disulfonic acid ,,

2-naphthylamino-3,6,8-trisulfonic acid 4-m- and p-nitroaniline, 4-nitroaniline-2-sulfonic acid,

3-nitro-6-sulphonic acid,

1.88.81: 7 and with m- or β-aminoacetanilide and 4-amibi-β-acetylaminotoluene-5-sulfonic acid.

Coupling Components:

Phenol-4'-sulfonic acid, 3-naphthol, -

2-Naphthol, · .... ·

6- or -7-sullic acid,. 2-Naphthyl-3,6- or -6,8-disulfonic acid, 1-naphthol-4-sulfonic acid, 1-phenyl-3-methyl-5-pyrazole-1- (4'-sulfophenyl) ) -3-Methyl-5-pyrazolone, 1- (tert-dichloro-4-sulfophenyl) -3-methyl-5-oxo-5-carboxylic acid,

3-Aminocarbonyl-4-methyl-6-hydroxymethyl

-2-: pyridine,

1-ethyl-S-cyanco or -?

-hydroxy-2-pyridone, roxЬЬ ^ ^ЦЦЦЦЦ М М М М М М М М:::::.

2,4,67-triamino-3-cyano-pyridine,

2- (3‘-sulf of enylamino-N, N -diamino) -

-cyanopyridine,. ...

2- (2'-hydroxyethylamino) -3-cyano-4-methyl-6-aminoipyridine,

2,6-bis (4-hydroxyethylylamino) -3-cyano-4-methylpyridine-1,2-benzoylamino-5-naphthol-7-sulfonic acid, 1-benzoylamino-8-naphthoyl-1, 6 or -4,6 -disulfonic acid, phenol, p-cresol, acetoanilide and acetoacet-2-m-methoxyamino-5-sulfonic acid,

1- (4'-sulfophenyl) -5-pyrazolo-3-k arboxylic acid, k-methyl-4-pyrrizolone,

4-hydroxy-2-quinolone, h-acetylamino-1-naphthyl-3-sulfonic acid,

And ^2-, mlnOnaftαlen-5,7-dlsulfoeová acid, l-naphthol-4,6- or -4,7-disulfonic acid.

Condensation of 2,4,6-Ig-chloro-1,3,5-thiazolines of formula V and 2,4,6-Ig-fluoro-1,3,5-trlazines of formula VII with a dye containing sulfo groups of formula IV, alkylenediamines or The arylendlamines of the formula VI and the amines of the formula VIII, optionally with diazotizable or couplingable HNR 1 -containing components, are preferably carried out in aqueous solution or suspension at low temperature and at slightly acidic, neutral to slightly alkaline pH. Preferably, the hydrogen fluoride released during condensation is continuously neutralized by the addition of an aqueous solution of an alkali hydroxide, carbonate or bicarbonate. The diazotization of the diazo-detectable amino-containing intermediate is generally carried out by treatment with nitrous acid in an aqueous mineral acid solution at a lower temperature and the coupling is carried out at a slightly acidic, neutral to slightly alkaline pH.

'Baryiva-obeopého' · '-carrier I se .... characterized by high reactivity. ^:: '

The dyes of the present invention are suitable for dyeing and printing a wide variety of materials; such as cotton, leather, wool, super polyamide fibers and superpolyurethanes, but especially cellulosic fibrous structure materials such as flax, pulp, regenerated cellulose, and especially cotton. The dye is suitable for dyeing both in a pull-out and in a foulard-in process in which the material is impregnated. aqueous dye solution or solution. A dye, optionally containing salts, and a dye is fixed after the alkaline treatment or in the presence of alkalis, possibly by the action of heat. · '· .... ·.

The dyes are also suitable for "printing", especially on cotton, as well as for "printing" nitrogen-containing fibers. - for example, wool, silk, and blended fabrics containing wool.

It is recommended that the dyeing and printing be thoroughly rinsed with cold and hot water, possibly with the addition of dispersing agents that facilitate diffusion of non-fixed dye fractions.

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

Example 1

31.4 parts of 8-amino-1-naphthol-3,6-disuffonic acid are first condensed with 18.5 parts of 2,4,6- &lt; 7 &gt; -chloro-5S-triazine. The resulting primary condensation product is then condensed with 21 parts of 1,4-diaminobenzene-k-sulfonic acid sodium salt and the obtained condensation product is coupled at pH 7-8 with a diazo compound prepared from 17.3 parts of 1-aminobenzene-2-sulfonic acid. 13.6 parts of 2,4,6-1H-fluoro-1 H -triazine are then added dropwise to the resulting red dye solution at 0-5 ° while maintaining the pH at 6.5 at the same time by the addition of 2N sodium hydroxide solution. After completion of the condensation, an aqueous solution is added

19.5 dUu of sodium so-aarninobeneen-S-sulfonic acid, the temperature is raised to 20 ° and the hydrofluoric acid released by condensation is continuously neutralized by dropwise addition of 2 N sodium hydroxide solution. The dye of formula XXXI is isolated from the red solution by addition of sodium chloride

19: 5377:

This dye dyes the cellulose fibers into brilliant red shades that are stable to moisture.

If, in the last condensation, an equivalent amount of 1-aminobenzene-4-sullonic acid or -2-amino-5-sulfobenzoic acid is used instead of 1-aminobenzene-3-sulfonic acid, red dyes with similar dyeing properties are also obtained .

If instead of 8-amino-1-hydroxynalthalene-3,6-disullonic acid, equivalent parts of the compounds listed in column 2 of Table 1 are used, instead of 1,4-diaminobenzene-3-sullonic acid equivalent parts of the compounds listed in column 3 are used, instead of 1-aminobenzene-2-sullonic acid equivalent parts of the compounds listed in the column

Finally, equivalent parts of the compounds listed in column 5 are obtained instead of -1-aminobenzene-3-sullonic acid, dyes having similar dyeing properties are obtained.

Coupling component Diamin Diazocomponent Amin Shade on cotton, d

Ф

Д

Д Д Ф Ф φ > '> > Cm Гч Ф Ф Ф Ю > ω > ω

Д Д Φ Φ N N Д Д Я Φ Φ 1 Д ХЭ r-4 WITH WHAT í-4 >> > » ά Φ ω -M X < + - » Φ > » Φ φ and 44 and . and Φ X> O > cd § CM and 1 CM ά Д G ,G Д ’ <w § 'G ca Д CD я гЧ СЛ t г-1 r4

'> ч '> 4 > > > > Гч Д о о O <5 Ф • Φ > SJ 1 > Ň > O > д с H Д . O CD cú CD what Д ω at řrl Fh Рч ) CJ о O O O ) N

Honor Д cd. Д what Д со Д Д Л СЛ A, φ Ф. >> , ω> » N Я 44 N Д Č Ф 'CD φ 'cd rO > 4Э> 0 p O O O я й Д • нН O • Д ° G Ч-Ч Д Д Я Д я Д 1 гЧ СЛ Λ?

honor Я . Я Д • гЧ 4 ^ ~ Г Ф , Я ю А 'З гЧ Я гН о сл СМ с /) Д * ф φ сл я b -м 44 Д SP >> 44 Д Д й 'ф N 4d ф Д 44 '5' > Q Д> Ф о ч-ч - Я 'Я О § хэ d S о д> § я Д д · S о

CD Ф я Я Я 1 Д- rQ , p . д д 'di Д >> со Д со Д <Ф д 1 Д Ф сл Λ φ. Д сл Д $ 1 д ф ел Φ > 4 φ >> ф S ф >> N Д 44 N Я А- я N Д 44 Φ 'CD CM 1 ф 'Я ф 'Cd Ф 'Я rQ > л ž Л> X) > 0 Q O £ 5 о о О О Д Д Д д я д я я д O • 44 • д °  д ° о and ч-ч G а а д а ч-ч Я Д read S я я д § Я (гЧ СЛ rd *, сл гЧ i - J. СП т-Ч i 1 гЧ сл (

cd Д

'cd>'.

д »'φ гЧ

1 Я t д а Д ф Ф N N д Ф сл Я ф >. ф ХЭ 44 хэ О о Д 'Я д д > G О а я д я • г-Н о- • г- < д «+ Н д со Я о \ гЧ сл Т-Г

talen-6-sulfonic acid sulfonic acid.

CM CO

3D

Example 2

31.4 parts of 8-amino-1-naphthol-3,6-disulfonic acid are condensed with cyanuric chloride at 0 ° and pH 1-2. Aqueous solution of 21 parts of 2,4-diaminobenzenesulphonic acid sodium salt is added to the primary product suspension and condensed at pH 4-5. -5-methylbenzenesulonic acid.

The resulting red dye solution is then added to a suspension of 2-aminobenzenesulphonic acid with 13.5 parts of 2,4,6-trifluoro-1,4-difluoro-1,3,5-triazine prepared by condensation of 17.3 parts of 2-aminobenzenesullonic acid. -1,3,5-triazine at 0 ° and pH 6. The hydrogen fluoride released by condensation is continuously neutralized by the addition of sodium carbonate solution. Upon completion of the condensation, the reaction product is isolated by evaporating water under reduced pressure as a red dye powder. The dye dyes the cellulose fibers into permanent blue-red shades. . '. Dyes of similar dyeing properties are obtained by using the following dilluorotriazinyl compound instead of 2- (2‘-suilolenyil amino) -4,6-dilluoro-1,3,5-triazine for the last condensation step.

C. Dilluorotriazinyl derivative

Parts

2-methoxy-4,6-difluoro-1,3,5-triazine

2-ethoxy-4,6-difluoro-N-trlazine

2- (2'-methylenylamino) -3,6-difluoro-2-methylthio-4,6-difluoro-3,3,5,5-triazine 2- [2'-ethoxyethoxy) -4,6-diiluoro-1,3,5-lriazine 2-iэαpropoxy-4,6-dilluor-l, 3,5-triazin-2-n buty.iamfno-4,6-difluoro-l, 3,5-triazfn 2- (2 ', 5 ^<ldisuilol phenylamino) -4,6-D-fluorine, 3,5-trphazine. .

2-diethylamino-4,6-difluoro-1,3,5-triazine

2- _(2'lm; ethyl 5 ^{<-suilolenylaminojl} LA eldilluor-l, 3,5-triaϊiiIf

2- (2‘-carboxyl-4‘-suilolenylamino) -,

2- (4'-Methyl-1,2 * Sulfonylbenzylamino) -4,6l-difluoro-SR-triazine

2- (2'-Chloro-5 * chloro-11-olenylamino) -4,6-dimethyl-3,5'-triazine

2- (2 ‘, 4‘-disulphenylamino) -4,6-difluoro. -1,3,5-triazine

2'-butoxy-4,6'-difluoro-1,3,5-thiazine

14.7

16.1

22.2

16.3

20.5.

19.1

18.2

36.8

18.8

30.2

33.2

30.2

32.4.

36.8

18.9

Example 3

9.42 parts of 6-amino-11 -naltol-3,5-disulfonic acid are condensed with 5.55 parts of cyanuric chloride. The obtained primary condensation product is condensed with 6.3 parts of M-dlaminobenzene-2-sulfonic acid. To the solution of the resulting condensation product is added

0.05 drops of 4.05 parts of 2,4,6-dimethyl-1,3-triaziline are added dropwise while maintaining the addition of 2 N sodium hydroxide solution. pH to 7. After the condensation has ended, 4.5 parts of a 25% aqueous ammonia solution are added and stirred at 15-20 ° C for 4 hours. To the solution of the coupling component of the formula thus obtained.

then a suspension of the diazonium compound prepared in a conventional manner from 5.19 parts of 2-amino-benzene-11-suiloic acid is added and coupling is carried out at pH 6-7. After the coupling, the dye is precipitated by addition of sodium chloride. Drying and grinding yields a dye powder which dyes the cellulosic water bath fabrics to constant orange shades.

Instead of condensation with 2,4,6-trifluoro-l, 3,5-triazine and subsequent reactions with ammonia, the condensation can also be carried out with 2-amino-4,6-difluoro-1,3,5-trlazine. The dye thus prepared is identical to the dye described above.

When, instead of 6-amino-naphthol-3,5-disulfonic acid, equivalent parts of the compounds listed in column 2 of the following table are used, instead of 1,4-diaminobenzene-2-sulfonic acid of the compound shown in Column 3, finally, instead of the 2-ammoniumbenzenesulfonic acid diazo compounds listed in column 5, dyes are obtained which dye the cellulose fiber fabrics to the shades shown in column 6.

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Example 4

12.56 parts of 8-amino-1-naphthol-3,6-disulfonic acid are condensed with 7.4 parts of cyanuric chloride as described in Example 2 and the obtained condensation product is coupled with a diazo compound from 6.92 parts of 1-aminobenzene- 2-sulfonic acids. A solution is then added

8.4 parts of the sodium salt of l, 4-dlaminobenzen-3-sulfonic acid and condensation at 10 to 12 °, with addition of 2 N sodium hydroxide to maintain the pH to 6. The resulting red dye solution is then added dropwise at 0 ° ^C 5.44 parts of 2,4,6-trifluoro-1,3,5-triazine while maintaining the pH at 6.5 by addition of 2N sodium hydroxide solution. After completion of the condensation, an aqueous solution of 9.5 parts of 2-amino-5-sulfobenzoic acid is added and stirred at 20-25 ° for three hours, while the hydrogen fluoride released by condensation is continuously neutralized by the addition of 2 N sodium hydroxide solution. The entire dye solution is spray dried to give a dark red dye powder which dyes the cellulose fibers from water baths to intense red shades.

Example 5

10.15 parts of 2-amino-5-methoxybenzenesulfonic acid are pseudo-colored and the resulting suspension is simultaneously allowed to flow to a well stirred solution of 13.05 parts of 2-amino-5-hydroxynaphthalene-7-sulfonic acid sodium salt. The pH is kept constant at 8.5 during the addition. At the end of the coupling, a solution of 9.25 parts of cyanuric chloride in acetone was added at 0 °, stirred at 0 ⁶ until the condensation was completed while maintaining the pH at 6.5 by concurrent addition of 2N sodium hydroxide solution. A solution of 10.8 parts of 1,3-diaminobenzene in water is then added and condensed further at the same pH and room temperature. The dye intermediate obtained is precipitated by the addition of sodium chloride, filtered and redissolved at 0 ° in water. 6.75 parts of 2,4,6-trifluoro-1,3,5-triazium are added dropwise to this solution over 20 minutes, while maintaining the pH at 7 by adding 2N sodium hydroxide solution at the same time. parts of morpholine and the mixture is further stirred at 0-5 ° and pH 8.5 until condensation is complete. From the aqueous dye solution, the dye is salted out by adding potassium chloride. The dye dyees cotton to scarlet-resistant shades.

Additional reactive dyes are obtained according to the data of this example by reacting the amino dye produced from the components listed in column 2 with cyanuric chloride, then condensing with the palladium listed in column 3, cyanurofluoride, and finally the amine listed in column 4. The dyes dye cotton or regenerated cellulose fibers for qdestructures listed in the last column.

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Example 6

17.3 parts of 1-aminobenzene-2-sulfonic acid are dissolved in water with the addition of 50 parts. parts of 2 N sodium hydroxide solution. Cool to 0 ° C, add 10 parts of sodium bicarbonate and add 13.5 parts of 2,4,6-trifluoro-1,3,5-triazine dropwise over 15 minutes. After completion of the condensation, mix with the solution. 21 parts of 1,3-diaminobenzene-6-sulfonic acid sodium salt and stirred at room temperature, while the hydrogen fluoride released by condensation is continuously neutralized by dropwise addition of 2 N sodium hydroxide solution. As soon as 1,3-diaminobenzene-6-sulfonic acid is no longer detectable, the reaction mixture is cooled again to 0 °, a solution of 18.5 parts of 2,4,6-trichloro-1,3,5-trlazirium in 50 ml is added. parts by volume of acetone and stirred at 0 ° while maintaining the pH at 6-7. Once all the trichlorotriazine has been consumed, an aminoazo dye solution of formula I is added.

(49 parts of sodium sulphate) is heated to 25-30 ° and condensed at a pH of 6 to 7, which is maintained at this value by continuous dropwise addition of 2N sodium hydroxide solution.

The reactive dye of formula XXXIII is isolated from the yellow solution

addition of sodium chloride. After drying and grinding a yellow dye powder is obtained. which dye cellulose fibers to brilliant yellow shades that are moisture-resistant.

Dyes of similar properties are obtained analogously to the above procedure by substituting 1-aminobenzene-2-sulfonic acid for the equivalent parts of the components listed in column 2 of Table 4, instead of 1,3-diaminobenzene-6-sulfonic acid. equivalent parts of the compounds listed in column 3 and, instead of the aminoazopyridone dyes, equivalent parts of the amino dyes listed in column 4.

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Example 7

187 parts of 4-amino-3-methylbenzenesulfonic acid were dissolved in water by adding 100 parts by volume of 40% sodium hydroxide solution to neutral solution. It is cooled to 0 ° by the addition of ice, 14 parts of secondary sodium phosphate are added and 135 parts of 2,4,6-trifluoro-1,3,5-triazine are added dropwise to the solution over 15 minutes with good stirring. By the simultaneous addition of 2 N sodium hydroxide solution, the pH of the reaction mixture is maintained at 7. After completion of the condensation, it is mixed with a solution of 210 parts of 1,3-diaminobenzene-6-sulfonic acid sodium salt and stirred at 10-15 ° while releasing hydrogen fluoride during condensation it is continuously neutralized by dropwise addition of 2 N sodium hydroxide solution. Once 1,3-diaminobenzene-6-sulfonic acid is no longer detectable, the reaction mixture is recooled to 0 °, 185 parts of ground cyanuric chloride are added and condensed at pH 8-7 until no more cyanuric chloride is present. Once again, an aqueous solution of 210 parts of 1,3-diaminobenzene-6-sulfonic acid sodium salt is added and further condensed at 15 ° and pH 6. 250 parts by volume of 4 N sodium nitrite solution are added to the obtained solution. the cooling to 0 ° is poured into 250 parts by volume of 32% hydrochloric acid. After decomposing any excess nitric acid by addition of sulfamic acid, 381 parts of 8-acetylamino-1-hydroxynaphthalene-3,8-disulfonic acid are added to the diazo compound and the pH of the solution is raised to 7 by slowly adding sodium hydroxide solution. which is salted out by the addition of sodium chloride, filtered, dried and ground to a red powder. This dye colors cellulose textile materials into brilliant red moisture-resistant shades.

If, instead of 8-acetylamino-1-hydroxynaphthalene-3,6-disulfonic acid, the coupling components listed in the following table are used, additional valuable reactive dyes are obtained which dye cotton to these shades.

6. Coupling Components Shade of 1-hydroxynaphthalene-4-scarlet sulfonic acid 1- (4‘-sulfophenyl) -3-methyl-yellow -5-pyrazolone 1-ethyl-3-cyano-4-methyl-yellow

6-hydroxy-2-pyridin-1,4-dimethyl-3-sulfomethyl-thyl-6-hydroxy-2-pyridone

2- (3'-sulfophenylamino) -4,6-orange diamino-3-cyanopyridine

8-Benzoylamino-1-hydro-red xynaphthalene-3,6-disulfonic acid 1-hydroxynaphthalene-4,7-scarlatic acid

-disulfonic acid.

Dyeing Procedure I parts of the dye prepared according to Example 1 were dissolved by adding 0.5 parts of m-nitrobenzenesulfonic acid sodium salt in 100 parts of water. The obtained solution is impregnated with a cotton fabric so that it receives 75% of its weight and then dried.

The fabric is then impregnated with a 20 ° warm solution containing 5 g of sodium hydroxide and 300 g of sodium chloride per liter, squeezed to 75% weight gain, steamed at 100 to 101 ° for 30 seconds, rinsed, soaped for hours 0.3% boiling solution of non-ionic detergent, rinsed and dried.

The dye formulation II parts of the dye of Example 1 were dissolved in 100 parts of water.

The solution was added to 1900 parts cold water, 60 parts sodium chloride was added, and 100 parts cotton fabric was added to the dye bath.

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

I will invent the subject

Claims (11)

A process for the preparation of filaments reactive with fibers of the general formula I O - N- | и l II II R <г ^R 3 _((j OF wherein D is a sulfo-containing organic dye residue, R 1, R 2 and R 1 are independently hydrogen or C 1 -C 4 alkyl, V is C 2 -C 6 alkylene or phenylene which may be substituted (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, carboxyl, sulfo or halogen atom, naphthylene moiety which may be substituted by a sulfo group, or a diphenylurea, diphenyloxethane, stilbene or diphenylethane residue which may be sulfo-substituted, and A is amino, hydroxylamino, hydrazino which may be substituted by phenyl or sulfophenyl, C1-4 alkylamino which may be substituted by hydroxyl, chlorine or phenyl, N, N-dialkylamino having 1 to 4 carbon atoms; Carbon atoms in alkyl, which may be substituted by hydroxyl, alkoxyalkylamino having 1. up to 4 carbon atoms in alkoxy, and alkyl, cyclohexylamino, morpholino, piperidino, piperazino, N-alkyl-N-phenylamino of 1 to 2 carbon atoms in alkyl, N-sulfomethyl-N-phenylamino, phenylamino which may be substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen, sulfo, sulfomethyl or carboxy, naphthylamino which may be substituted by sulfo, C1-6 alkoxy carbon atoms, alkoxyalkoxy having 1 to 4 carbon atoms in each of the alkoxy groups or alkylthio having 1 to 4 carbon atoms,. Characterized in that, in any order, simultaneously or in individual stages, they are condensed together · an organic dye containing sulfo groups or dye components of the formula IV D — NH, ·. I; - ... ·. ... Rl ..... ·. . ·. . (Iv) where D and R 1 are as defined above, 2,4,6-richlor-1,3,5-triazine of formula V (V) _t ... C. . alkylenediamine or arylenediamine in general. of formula VI - ..... HN — B — NH ·, »2 R3 R 3 (VI) wherein R 6, R 8B are as defined above, 2,4 ^ ii ii ii ^ ^ l ^ ^ ^ ^ ^ ^ VII VII O ». F and a compound of formula VIII H — A, (VIII) wherein A is as defined above. 2. A process according to claim 1, wherein the compounds of formulas IV to VIII are used as starting compounds, wherein D is an organic dye radical containing sulfo groups, R1, R2 and R5 are hydrogen atoms, B is an arylene radical containing at least one sulfo group and A is an optionally substituted amino group. ···· 3. The process according to claim 1, wherein the starting compounds are compounds of the formulas IV to VII, wherein D is an azo dye residue. containing · sulfo groups, · R 1, R 2 and · R 3 'are atoms. hydrogen, B is a phenyl radical containing one or two sulfo groups and A is an optionally substituted amino group. . · 4. Process according to claim 1, characterized in that compounds of the formulas IV are used as starting compounds. to VIII, where D is a sulfo group containing a series of H-acids or J-acids, R 1, R 2 and R 5 independently of one another are hydrogen or alkyl of 1 to 4 atoms. B is a sulfophenyl radical, and A is an optionally substituted amino group. ”, .---- 77 · ..... 5. The method according to clause ·. 1 for the preparation of reactive dyes of the general formula I, wherein D is a sulfo group-containing azo dye residue characterized in that the diazotized aromatic diamine comprises an NHR 1 group, wherein: Ri · has the meaning given in point 1, the coupling component, wherein the traceable aromatic diamine and the coupling component together contain at least one sulfo group, ЗДб-МсЫог-ТД ^ + г ^ т or an "arylendiamine of the general formula VI," wherein. R2, R5, and B.. . have the meanings given therein,. , ·,, 2,, 4 ^ 43-triple ^ .1 ·, 3>: -: Γ1 & ζώ formulas, · VII · · and compound · general · formula Vili; Where má is meaningful at point 1 · 1 · together · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 7 - 6. A process according to claim 1 for the preparation of a reactive dye of the formula I, wherein D is a sulfo group-containing azo dye residue, characterized in that the coupling component comprises HNR 1 -. a group wherein R 1 is as defined in item 1, a diazotable aromatic amine, wherein the coupling component and the diazotable aromatic amine together contain at least one sulfo group; VI, wherein R 2, R 5 and B are as defined in 1, 2,4,6-trifluoro-1,3,5-triazine of formula. The compound of formula (VIII), wherein A ‘is as defined in 1, is reacted together by diazocation, coupling and condensation. . 7. The process of claim 5, wherein the diazotizable aromatic diamine comprises an HNR1 group wherein R1 is the starting compound. is a hydrogen atom, a coupling component, wherein the diazotizable diamine and the coupling component together contain at least one sulfosulfate42 19 S 317. 2,4,6-trichloro-1,3,5-triazine of formula (V); an arylendiamine of formula (VI) wherein R? and R5 is hydrogen; and V is a phenylene radical containing one or two sulfo, 2,4,6-trifluoro-1,3,5-triazine of formula VII and a compound of formula VIII wherein A is optionally substituted amino, 8. A process according to claim 6, wherein the starting compound is a coupling component comprising an HNR1 group, wherein R1 is hydrogen, a diazotable aromatic amine, wherein the coupling component and the diazable aromatic amine together contain at least one sulfo group, 2,4,6-trichloro-1,3,5-triazine of formula V, an arylenediamine of formula VI, wherein R 2 and R 3 are hydrogen atoms, V is a phenylene radical containing one or two sulfos (4 wherein D 1 is a diazocomponent radical) and A is an optionally substituted amino group, characterized in that the 2,4,6-tri-chloro-1,3,5-triazine of the formula V is condensed with the H-acid of the formula IX fully; The compound of formula VII, 6-trifluoro-1,3,5-triazine, and the compound of formula VIII, wherein A 1 is an optionally substituted amino group. 9. A process as claimed in claim 6, wherein the H-acid or J-acid containing the HNR1 group is used as the starting compound, wherein R1 is hydrogen or C1-C4 alkyl, a dispersible aromatic amine, 4,6-trichloro-1,3,5-triazine of formula (V); an arylendiamine of formula (VI): and R 3 are, independently of one another, hydrogen or C 1 -C 4 alkyl, and V is a sulfophenylene radical, 2,4,6-trifluoro-1,3,5-triazine of formula VIII and a compound of formula VIII, wherein A is optionally substituted amino. 10. The process of item 6 for preparing fiber reactive dyes of formula II and phenylenediaminosulfonic acid of formula X formed by the secondary condensation product of formula XI (XII) is coupled with a diazotized amine of formula XII wherein Di is as defined above; Di — NH? (XII) is condensed with _2,4) 6 - rlfÍuór-l, 3,5-tria zine -vzorce VII and the resulting condensation product is condensed with - a compound of formula VIII obecné44 it, - wherein A is an optionally substituted amino moieties. 11. A process according to claim 10 for the preparation of fiber-reactive dyes of the formula III, characterized in that the 2,4,6-richlor-1,3,5-triazine of the formula V is condensed with an H-acid of formula-IX, the primary condensation product obtained. is condensed with phenylenediaminosulfonic acid of formula X, the obtained secondary condensation product is coupled with diazotized aminobenzenesulfonic acid of formula XIV CJW mi The SQ 1 H obtained azo compound is condensed with a 2,4,6-trifluoro-1,3,5-triazine of formula VII and the obtained condensation product is condensed with an aminobenzenesulfonic acid of formula XIV.