JPH101620A - Reactive dye composition and method for dyeing or printing fiber material using the same - Google Patents

Abstract

(57) [Summary] PROBLEM TO BE SOLVED: To be very good for near neutral to alkaline aqueous solution
Dissolving reactive dye composition and dyeing or printing using the same
Provide a way. (A) A free acid is represented by the following general formula (I) Wherein A is phenylene which may be substituted or
Optionally substituted naphthylene, wherein B is substituted
Represents a good phenylene, R¹And R^TwoAre independent of each other
A hydrogen atom or a lower alkyl which may be substituted
And Y represents phenylene which may be substituted or substituted
Represents an optionally substituted lower alkylene;¹And Z^TwoIs
Independently of one another, -CH = CH_Two, -CH_TwoCH_TwoL or
-CH_TwoCH _TwoOH, where L is the action of alkali
Represents a group leaving,¹, Z^TwoOne of-
CH_TwoCH_TwoOH, the other is -CH = CH_Twoor
Is -CH_TwoCH_TwoL. Bisazo compound represented by the formula
A substance or a salt thereof; (B) Condensation of naphthalene sulfonic acids and formaldehyde
A reactive dye composition comprising:
Stuff.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a reactive dye composition which is very well soluble in any liquid aqueous solution between near neutral and alkaline.

[0002]

2. Description of the Related Art In an effective method for dyeing or printing a fiber material such as cellulose fiber using a reactive dye, for example, in an exhaust dyeing method, a padding method and a one-phase printing method, a neutral dye is used. -It is necessary to use a dye having good solubility in an alkaline aqueous solution, and if a dye having insufficient solubility is used, the resulting dyed or printed matter may lack uniformity with spots or the like. It has been known. on the other hand,
Conventionally, it has been known that some reactive dye compositions containing an auxiliary agent such as ligninsulfonic acid have relatively high solubility in an aqueous solution near neutrality.

[0003]

However, even with such a reactive dye composition, the solubility in an alkaline aqueous solution is not always sufficient. Regardless of the nature, there is a strong demand for the development of reactive dye compositions having sufficient solubility.

[0004]

Under such circumstances, the present inventors have found that sufficient solubility in any liquid aqueous solution between near neutral and alkaline irrespective of its liquidity. As a result of intensive studies for the purpose of obtaining a reactive dye composition having, a reactive dye composition comprising a specific bisazo compound or a salt thereof, and a condensate of an alkylnaphthalenesulfonic acid and formaldehyde exhibits the desired performance. And completed the present invention.

That is, according to the present invention, (a) the free acid is represented by the following general formula (I)

[0006]

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Wherein A represents phenylene which may be substituted or naphthylene which may be substituted; B represents phenylene which may be substituted; R ¹ and R ²
Each independently represents a hydrogen atom or an optionally substituted lower alkyl; X represents an optionally substituted pyridinio, a compound represented by the following general formula (X1), (X2), (X3) or (X4)

[0008]

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(Where R⁷, R⁸, R⁹And R^TenIs
Independently, a hydrogen atom or an optionally substituted lower
Killed, optionally substituted phenyl or substituted
May represent naphthyl, Q^TwoIs -CH_Two-, -O-,
-S-, -SO_Two-Or -NR ¹¹-, Where R¹¹
Represents a hydrogen atom or an optionally substituted lower alkyl.
And t represents 1, 2 or 3. Y is substituted
Optionally substituted phenylene or optionally substituted low phenylene
Z represents a lower alkylene;¹And Z^TwoAre independent of each other,
-CH = CH_Two, -CH_TwoCH_TwoL or -CH_TwoCH_Two
Represents OH, wherein L is a group capable of leaving by the action of an alkali
Represents, Z¹, Z ^TwoIs -CH_TwoCH_TwoO
H, the other is -CH = CH_TwoOr -CH_TwoCH
_TwoL. Or a salt thereof.
And (b) the condensation of naphthalenesulfonic acids and formaldehyde
A reactive dye composition comprising:
And a method for dyeing or printing fiber materials using the same.
Is what you do. Hereinafter, the present invention will be described in detail.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The bisazo compound used in the present invention has a free acid represented by the following general formula (I), wherein A represents an optionally substituted phenylene or a substituted phenylene. Represents an optionally substituted naphthylene, and B represents an optionally substituted phenylene. As such optionally substituted phenylene and naphthylene, for example,
Methyl, ethyl, n-propyl, iso-propyl, n
-Butyl, iso-butyl, lower alkyl such as sec-butyl, methoxy, ethoxy, n-propoxy, iso
-Propoxy, n-butoxy, iso-butoxy, se
lower alkoxy such as c-butoxy, halogen atoms such as chloro and bromo, nitro, sulfo, carboxy, acetylamino, phenylene and naphthylene which may be substituted with one or two substituents selected from the group of ureido; Can be mentioned.

As the optionally substituted phenylene in A, preferred groups include, for example,

[0012]

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[Wherein the bond indicated by * is a compound represented by the general formula (I)
Represents a bond leading to —NR ¹ —. And the like. Further, as the optionally substituted naphthylene in A, preferred groups include, for example, the following general formulas (II) and (III)

[0014]

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[Wherein p is 1 or 2, q is 0 or 1, r
Represents 0 or 1, and the bond indicated by * represents a bond leading to —NR ¹ — in formula (I). And the like, and specifically,

[0016]

Embedded image

And the like.

In the optionally substituted phenylene represented by B, preferred groups include, for example,

[0019]

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[Wherein the bond indicated by * is a compound represented by the general formula (I)
Represents a bond leading to —SO ₂ —. And the like.

In the bisazo compound (I) used in the present invention, R ¹ and R ² each independently represent a hydrogen atom or a lower alkyl which may be substituted. And lower alkyl which may be substituted by a group selected from the group consisting of a cyano group, an alkoxy group, a halogen atom, a carboxy group, a carbamoyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a sulfo group, and a sulfamoyl group. .

Specific examples thereof include a methyl group,
Ethyl group, n-propyl group, iso-propyl group, n-
Butyl group, iso-butyl group, sec-butyl group, 2-
Hydroxyethyl group, 2-hydroxypropyl group, 3-
Hydroxypropyl group, 2-hydroxybutyl group, 3-
Hydroxybutyl group, 4-hydroxybutyl group, 2,3
-Dihydroxypropyl group, 3,4-dihydroxybutyl group, cyanomethyl group, 2-cyanoethyl group, 3-cyanopropyl group, methoxymethyl group, ethoxymethyl group,
2-methoxyethyl group, 2-ethoxyethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 2-hydroxy-3-methoxypropyl group, chloromethyl group, bromomethyl group, 2-chloroethyl group, 2-bromomethyl group , 3-chloropropyl group, 3-bromopropyl group, 4
-Chlorobutyl group, 4-bromobutyl group, carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 4-carboxybutyl group, 1,2-dicarboxyethyl group, carbamoylmethyl group, 2-carbamoylethyl group, 3-carbamoylpropyl group, 4-carbamoylbutyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, 2-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 3-ethoxycarbonylpropyl group, 4-methoxycarbonylbutyl group, 4-ethoxycarbonylbutyl group, methylcarbonyloxymethyl group,
Ethylcarbonyloxymethyl group, 2-methylcarbonyloxyethyl group, 2-ethylcarbonyloxyethyl group, 3-methylcarbonyloxypropyl group, 3-ethylcarbonyloxypropyl group, 4-methylcarbonyloxybutyl group, 4-ethylcarbonyl Oxybutyl, sulfomethyl, 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, sulfamoylmethyl, 2-sulfamoylethyl, 3-sulfamoylpropyl, 4-sulfamoyl A butyl group and the like can be mentioned. R ¹ and R ² are preferably a hydrogen atom, methyl and ethyl.

In the bisazo compound (I) of the present invention, X represents an optionally substituted pyridinio, a group represented by the general formula (X1), (X2), (X3) or (X4). Here, the optionally substituted pyridinio includes
Examples include carboxy, carbamoyl, sulfo, halogeno, and optionally substituted pyridinio which may be substituted with a group selected from the group of alkyl having 1 to 4 carbon atoms. Wherein the carbon number may be 1 to 4 which may be substituted
As the alkyl of, for example, 2-hydroxyethyl,
2-sulfoethyl and the like.

Specific examples of such pyridinio include pyridinio, 2-, 3- or 4-carboxypyridinio, 2
-, 3- or 4-carbamoylpyridinio, 3-sulfopyridinio, 4- (2-sulfoethyl) pyridinio, 3
-(2-hydroxyethyl) pyridinio, 4-chloropyridinio, 3-methylpyridinio, 3,5-dicarboxypyridinio and the like can be mentioned. Preference is given to pyridinio substituted with carboxy or carbamoyl, of which carboxypyridinio is preferred, and 3- or 4-carboxypyridinio is particularly preferred.

In the group represented by the general formula (X2), Q ² represents —CH ₂ —, —O—, —S—, —SO ₂ — or —NR ¹¹
Represents-. Here, R ¹¹ represents a hydrogen atom or an alkyl which may be substituted. As such R ¹¹ , for example,
Examples thereof include a hydrogen atom, an alkyl having 1 to 4 carbons, and an alkyl having 1 to 4 carbons substituted with an alkoxy having 1 to 4 carbons. Among them, a hydrogen atom, methyl and ethyl are preferred. t is 1, 2 or 3. The general formula (X
Specific examples of the group represented by 2) include, for example, pyrrolidino, piperidino, piperazino, n-alkylpiperazino, morpholino and the like. Among them, Q ²
Is preferably —CH ₂ — or —O—, and t is 2. Specific examples thereof include piperidino and morpholino as groups represented by the general formula (X2).

In the groups represented by formulas (X1), (X3) and (X4), R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an optionally substituted alkyl, Represents phenyl which may be substituted or naphthyl which may be substituted; Examples of such alkyl include alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, sulfamoyl, carbamoyl, hydroxy, halogeno, cyano,
Examples thereof include carboxylic acid esters, sulfonic acid esters, alkyl and cyclohexyl having 1 to 4 carbon atoms which may be substituted by one or two substituents selected from the group of phenyl and sulfate which may be substituted. it can. Here, the optionally substituted phenyl is, for example, an alkyl having 1 to 4 carbons, an alkoxy having 1 to 4 carbons, a sulfo and a halogeno, which are substituted by 1 or 2 substituents selected from the group of halogeno. Phenyl and the like.

Specific examples of such alkyl include the aforementioned R
^{In addition} to the optionally substituted alkyl exemplified in ^{1 above} ,
Sulfatoethyl, benzyl which may be substituted and the like can be mentioned. Preferably, methyl, ethyl,
n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-hydroxyethyl, 2-sulfatoethyl, 2-sulfoethyl, 2-methoxyethyl, 2-carboxyethyl, 2-carbamoylethyl,
2-sulfamoylethyl, benzyl, 2-, 3- or 4-sulfobenzyl and the like.

In the groups represented by formulas (X1), (X3) and (X4), the optionally substituted phenyl in R ⁷ , R ⁸ , R ⁹ and R ¹⁰ includes, for example, chloro,
Halogeno such as bromo, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons, sulfo, carboxy, hydroxy, cyano, carbamoyl, sulfamoyl, carboxylate, 2-hydroxyethylsulfonyl, amino, acylamino, and carbon number And phenyl which may be substituted by one or two substituents selected from the group of amino substituted by 1-4 alkyls.

Specific examples of such phenyl include, for example, phenyl, 2-, 3- or 4-methylphenyl, 2
-, 3- or 4-methoxyphenyl, 2-, 3- or 4
-Ethylphenyl, 2-, 3- or 4-ethoxyphenyl, 2-, 3- or 4-carboxyphenyl, 2-3
-Or 4-chlorophenyl, 2-, 3- or 4-sulfophenyl, 3-sulfo-4-methoxyphenyl, 2-,
3- or 4-hydroxyphenyl and the like. Preferred are phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-sulfophenyl.

In the groups represented by the general formulas (X1), (X3) and (X4), the optionally substituted naphthyl in R ⁷ , R ⁸ , R ⁹ and R ¹⁰ includes, for example, chloro,
Halogeno such as bromo, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons, sulfo, carboxy, naphthyl which may be substituted by 1, 2 or 3 substituents selected from the group of hydroxy, etc. Can be mentioned.

Specific examples of such naphthyl include, for example, 2-, 3-, 4-, 5-, 6-, 7- or 8-sulfo-1-naphthyl, 1-, 5-, 6-, 7- Or 8-sulfo-2-naphthyl, 1,5-, 5,7-, 6,8-, 4,
8-, 4,7-, 3,8-, 4,6-, 3,7- or 3,6
-Disulfo-2-naphthyl, 4,6,8-, 2,4,7- or 3,6,8-trisulfo-1-naphthyl, 1,5,7-,
4,6,8- or 3,6,8-trisulfo-2-naphthyl and the like. Preferably, 2-, 3-, 4-, 5-,
6-, 7- or 8-sulfo-1-naphthyl, 1-, 5
-, 6-, 7- or 8-sulfo-2-naphthyl.

In the bisazo compound (I) of the present invention,
When X is the general formula (X1) represented by —NR ⁷ R ⁸ , when a specific example of the group is represented by an amine compound (HNR ⁷ R ⁸ ) used for forming the group, for example, The following can be mentioned.

Ammonia;

1-aminobenzene, 1-amino-2-,
-3- or -4-methylbenzene, 1-amino-2,4
-, -3,4- or -3,5-dimethylbenzene, 1-amino-2-, -3- or -4-ethylbenzene, 1-amino-2-, -3- or -4-methoxybenzene, 1 −
Amino-2-, -3- or -4-ethoxybenzene, 1
-Amino-2-, -3- or -4-chlorobenzene, 1
-Amino-2-, -3- or -4-bromobenzene, 1
-Amino-2-, -3- or -4-fluorobenzene,
3- or 4-aminophenylmethanesulfonic acid, 2-,
3- or 4-aminobenzenesulfonic acid, 3- or 4-
Methylaminobenzenesulfonic acid, 3- or 4-ethylaminobenzenesulfonic acid, 5-aminobenzene-1,
3-disulfonic acid, 6-aminobenzene-1,3- or -1,4-disulfonic acid, 4-aminobenzene-1,2-
Disulfonic acid, 4-amino-5-methylbenzene-1,
2-disulfonic acid, 2-, 3- or 4-aminobenzoic acid, 5-aminobenzene-1,3-dicarboxylic acid, 5-
Amino-2-hydroxybenzenesulfonic acid, 4-amino-2-hydroxybenzenesulfonic acid, 5-amino-
2-ethoxybenzenesulfonic acid, N-methylaminobenzene, N-ethylaminobenzene, 1-methylamino-3- or -4-methylbenzene, 1-ethylamino-
3- or -4-methylbenzene, 1-methylamino-2
-, -3- or -4-chlorobenzene, 1-ethylamino-2-, -3- or -4-chlorobenzene, 1- (2
-Hydroxyethyl) amino-3-methylbenzene, 3
-Or-methylaminobenzoic acid, 1-amino-2-methoxy-5-methylbenzene, 1-amino-2,5-dimethoxybenzene, 2-, 3- or 4-aminophenol, 1-amino-3- or -4-acetylaminobenzene, 2,4- or 2,5-diaminobenzenesulfonic acid,
1-aminobenzene-3- or -4- (b-hydroxyethylsulfone), 2-, 4-, 5-, 6-, 7- or 8-aminonaphthalene-1-sulfonic acid, 1-, 4-,
5-, 6-, 7- or 8-aminonaphthalene-2-sulfonic acid, 7-methylaminonaphthalene-2-sulfonic acid, 7-ethylaminonaphthalene-2-sulfonic acid, 7
-Butylaminonaphthalene-2-sulfonic acid, 7-isobutylaminonaphthalene-2-sulfonic acid, 4-, 5-
-, 6-, 7- or 8-aminonaphthalene-1,3-disulfonic acid, 2-, 3- or 4-aminonaphthalene-
1,5-disulfonic acid, 4- or 8-aminonaphthalene-1,6-disulfonic acid, 4-aminonaphthalene-1,7
-Disulfonic acid, 3- or 4-aminonaphthalene-2,
6-disulfonic acid, 3- or 4-aminonaphthalene-
2,7-disulfonic acid, 6- or 7-aminonaphthalene-1,3,5-trisulfonic acid, 4-, 7- or 8-aminonaphthalene-1,3,6-trisulfonic acid, 4-aminonaphthalene Aromatic amines such as -1,3,7-trisulfonic acid;

Methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, dimethylamine, diethylamine, methylethylamine, allylamine, 2-chloroethylamine, 2-methoxyethylamine, 2-amino Ethanol, 2-methylaminoethanol, bis (2-hydroxyethyl) amine, 2-acetylaminoethylamine, 1-amino-2-propanol, 3-methoxypropylamine, 1-amino-3-dimethylaminopropane, 2-amino Ethanesulfonic acid amide, 2-aminoethanesulfonic acid, aminomethanesulfonic acid, 2-methylaminoethanesulfonic acid amide, 2
-Methylaminoethanesulfonic acid, 3-amino-1-propanesulfonic acid, 2-sulfatoethylamine, aminoacetic acid, methylaminoacetic acid, 3-aminopropionic acid, 3-aminopropionic amide, 3-methylaminopropionic acid, 3-methylaminopropionamide,
ε-aminocaproic acid, benzylamine, 2-, 3- or 4-sulfobenzylamine, 2-, 3- or 4-chlorobenzylamine, 2-, 3- or 4-methylbenzylamine, N-methylbenzylamine, 1-phenylethylamine, 2-phenylethylamine, 1-phenyl-
Aliphatic amines such as 2-propylamine.

Preferred examples of the amine compound represented by HNR ⁷ R ⁸ include aniline and
N-methylaniline, N-ethylaniline, 2-, 3-
Or 4-chloroaniline, N-methyl-2-, -3- or -4-chloroaniline, N-ethyl-2-, -3- or -4-chloroaniline, 2-, 3- or 4-methylaniline , 2-, 3- or 4-ethylaniline, 2-3
-Or 4-methoxyaniline, 2-, 3- or 4-ethoxyaniline, 2-, 3- or 4-hydroxyaniline, aniline-2-, -3- or -4-sulfonic acid, 3
-Or 4-methylaminobenzenesulfonic acid, 3- or 4-ethylaminobenzenesulfonic acid, 2-, 3- or 4-carboxyaniline, ammonia, methylamine,
Ethylamine, dimethylamine, taurine, N-methyltaurine, mono- or di-ethanolamine, 2-sulfamoylethylamine, 2-carbamoylethylamine and the like can be mentioned. Among these, aniline, N-methylaniline, N-ethylaniline, 2-, 3- or 4-chloroaniline, N-methyl-
2-, -3- or -4-chloroaniline, N-ethyl-
2-, -3- or -4-chloroaniline, 2-, 3- or 4-methylaniline, 2-, 3- or 4-ethylaniline, 2-, 3- or 4-methoxyaniline, 2-3
-Or 4-ethoxyaniline, 2-, 3- or 4-hydroxyaniline, aniline-2-, -3- or -4-sulfonic acid, 3- or 4-methylaminobenzenesulfonic acid, 3- or 4-ethyl Aminobenzenesulfonic acid, 2
-, 3- or 4-carboxyaniline and the like are particularly preferred.

X is the aforementioned general formula (X) represented by -OR ⁹
In the case of 3), when a specific example of the group is represented by a compound (HOR ⁹ ) used to form the group, the following can be exemplified.

Phenol, 1-hydroxy-2-, -3
-Or -4-methylbenzene, 1-hydroxy-3,4
-Or -3,5-dimethylbenzene, 1-hydroxy-
2-, -3- or -4-ethylbenzene, 1-hydroxy-2-, -3- or -4-methoxybenzene, 1-hydroxy-2-, -3- or -4-ethoxybenzene,
1-hydroxy-2-, -3- or -4-chlorobenzene, 3- or 4-hydroxyphenylmethanesulfonic acid, 3- or 4-hydroxybenzenesulfonic acid, 5-
Hydroxybenzene-1,3-disulfonic acid, 2-hydroxybenzene-1,4-disulfonic acid, 4-hydroxybenzene-1,2-disulfonic acid, 4-hydroxy-
5-methylbenzene-1,2-disulfonic acid, 3- or 4-hydroxybenzoic acid, 5-hydroxybenzene-
Phenols such as 1,3-dicarboxylic acid, 5-hydroxy-2-ethoxybenzenesulfonic acid;

2-, 4-, 5-, 6-, 7- or 8-hydroxynaphthalene-1-sulfonic acid, 1-, 4-, 5-
-, 6-, 7- or 8-hydroxynaphthalene-2-sulfonic acid, 4-, 5-, 6-, 7- or 8-hydroxynaphthalene-1,3-disulfonic acid, 2-, 3- or 4
-Hydroxynaphthalene-1,5-disulfonic acid, 4-
Or 8-hydroxynaphthalene-1,6-disulfonic acid, 4-hydroxynaphthalene-1,7-disulfonic acid, 3- or 4-hydroxynaphthalene-2,6-disulfonic acid, 3- or 4-hydroxynaphthalene-2, 7
-Disulfonic acid, 6- or 7-hydroxynaphthalene-
Naphthols such as 1,3,5-trisulfonic acid, 4-, 7- or 8-hydroxynaphthalene-1,3,6-trisulfonic acid, 4-hydroxynaphthalene-1,3,7-trisulfonic acid ;

Methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, 2-chloroethanol, 2-methoxyethanol, 2-ethoxyethanol, 3-methoxypropanol, 3-ethoxypropanol, -Hydroxyethanesulfonic acid, 3-hydroxy-1-propanesulfonic acid, 2-cyanoethanol, 2-sulfatoethanol, glycolic acid, 3-hydroxypropionic acid, benzyl alcohol, 2-, 3- or 4-chlorobenzyl alcohol , 4-methylbenzyl alcohol, 2-, 3- or 4-sulfobenzyl alcohol, 2
Aliphatic alcohols such as phenylethanol and 1-phenyl-2-propanol.

[0041] X is the formula represented by -SR ¹⁰ (X
In the case of 4), when a specific example of the group is represented by the compound (HSR ¹⁰ ) used to form the group, for example,
Examples of the group used for forming the general formula (X3) include the compounds exemplified above in which the hydroxyl groups in phenols, naphthols, and aliphatic alcohols are each changed to a mercapto group.

In the bisazo compound (I) of the present invention,
X represents an optionally substituted pyridinio, a compound represented by the general formula (X
1) a (X2), (X3) or (but is a group represented by X4), the formula preferably represented by -NR ⁷ R ⁸ (X1). Further, in the group represented by the general formula (X1), the group represented by R ⁷ or R ⁸ is preferably phenyl which may be substituted with one of them, and more preferably, R ⁷ is , Hydrogen, methyl or ethyl, and R ⁸ is alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons, sulfo, carboxy, halogeno,
In this case, it is phenyl which may be substituted with a group selected from the group consisting of hydroxy, cyano and acylamino.

Further, in the bisazo compound (I) of the present invention, Y represents optionally substituted phenylene or optionally substituted lower alkylene. Examples of such phenylene include those exemplified as B above. And phenylene which may be substituted as described above.

Examples of the alkylene include lower alkyl having 1 to 4 carbon atoms which may be substituted, and 1 to 4 carbon atoms.
4, lower alkoxy, halogeno, hydroxy, sulfo,
Examples thereof include alkylene having 2 to 4 carbon atoms which may have a substituent, such as carboxy, cyano, lower alkoxycarbonyl, lower alkylcarbonyloxy, and carbamoyl. Among them, unsubstituted ethylene, trimethylene, tetramethylene and the like are preferable.

In the bisazo compound (I) of the present invention,
Z¹And Z^TwoAre independently of each other -CH = CH_Two, -CH
_TwoCH_TwoL or -CH_TwoCH_TwoOH, where:
L is a group capable of leaving under the action of an alkali, and specifically,
For example, sulfates, thiosulfates, phosphate esters
Groups and halogen atoms, etc.
In particular, a sulfate group is preferable. Follow
And Z¹And Z^TwoPreferred specific examples of -CH =
CH_Two, -CH_TwoCH_TwoOSO_ThreeH and -CH_TwoCH_Two
OH, among which -CH _TwoCH_TwoOS
O_ThreeH is particularly preferred. Where Z¹And Z^TwoAny of
One is -CH_TwoCH_TwoOH, the other is -CH
= CH_TwoOr -CH_TwoCH_TwoL.

The method for producing the bisazo compound (I) of the present invention is not particularly limited, but can be obtained, for example, as follows. The free acid is represented by the following general formula (V)

[0047]

Embedded image

Wherein Z ¹ , A, B and R ¹ have the same meanings as described above. A bisazo compound represented by the following general formula (VI)

[0049]

Embedded image XH (VI)

[Wherein, X represents the same meaning as described above. ]
And a compound represented by the following general formula (VII):

[0051]

Embedded image Z ² —SO ₂ —Y—NH—R ² (VII)

[Wherein, Z ² , Y and R ² have the same meanings as described above. And 2,4,6
By condensation with -trihalogeno-s-triazine, the bisazo compound (I) of the present invention can be obtained.

In this condensation reaction, the order of condensation of each compound is not particularly limited, but when the amine compound represented by the general formula (VII) is an aliphatic amine, this is first or secondly. Is preferably condensed. The conditions of the condensation reaction are not particularly limited. For example, the first condensation reaction is performed at a temperature of −10 ° C. to + 40 ° C.
Performed under conditions of pH 1 to 10, the second condensation reaction is
Carried out at a temperature of 0 ° C to 70 ° C and a pH of 2 to 10,
The third condensation reaction is performed at a temperature of 10 ° C to 100 ° C and a pH of 2
Examples of conditions performed under the conditions of 9

Further, specific compounds of 2,4,6-trihalogeno-s-triazine used herein include, for example,
Cyanuric chloride, cyanuric fluoride and the like can be mentioned.

The bisazo compound (I) of the present invention may be in the form of a free acid, a salt thereof, or a mixture thereof. Preferred are alkali metal salts, alkaline earth metal salts, and mixtures containing them, and among them, sodium salts, potassium salts, lithium salts and mixtures containing them are preferred.

On the other hand, in the present invention, the condensate of naphthalenesulfonic acid and formaldehyde of (b) is used.
Examples of the naphthalene sulfonic acids serving as a raw material of the condensate of (b) include naphthalene sulfonic acid and methyl,
1-4 carbon atoms such as ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl and sec-butyl
And naphthalenesulfonic acid substituted with a lower alkyl.

Specific examples of such naphthalenesulfonic acids include naphthalenesulfonic acid, mono- or dimethylnaphthalenesulfonic acid, mono- or diethylnaphthalenesulfonic acid, mono- or dipropylnaphthalenesulfonic acid, and mono- or dibutylnaphthalenesulfonic acid. Can be.

In the condensate (b), at least one selected from the naphthalene sulfonic acids is used as naphthalene sulfonic acid as a raw material, and preferably two or more are used. The method for condensing these naphthalenesulfonic acids with formaldehyde is not particularly limited, but can be carried out, for example, by a known method.

In the condensate (b), the degree of sulfonation (the degree of sulfonation in which one equivalent of a sulfo group is substituted for one equivalent of a naphthalene is defined as 100%) is 50 to 150% as an average value. It is about. Preferably, 80-
It is about 120%. The average degree of condensation ((b)) is the average of the number of naphthalenesulfonic acid residues in one molecule of the condensate, and the average degree of condensation of a condensate comprising 2 equivalents of naphthalenesulfonic acid and 1 equivalent of formaldehyde is 2.0. Yes.)
Is about 1.1 to 3, preferably about 1.5 to 2.5.

The condensate of (b) used in the present invention may be in the form of a free acid, a salt thereof, or a mixture thereof. It is an alkali metal salt and a mixture containing it, and among them, a sodium salt, a potassium salt, a lithium salt and a mixture containing them are preferred.

In the reactive dye composition of the present invention, the condensate (b) contained may be one kind or a plurality of kinds.

Further, in the reactive dye composition of the present invention, the bisazo compound of (a) or a salt thereof used in the reactive dye composition of the present invention;
Weight composition ratio (a) :( b) of the condensate of 2: 8-9.
8: 0.2, more preferably,
3: 7 to 9.5: 0.5.

Further, the dye composition of the present invention may contain other auxiliaries as needed, as long as the characteristics of the present invention are not impaired. Examples of such auxiliary agents include hydrotropic agents such as urea and anthraquinone-2-sulfonic acid,
Examples include saccharides such as dextrin, electrolytes such as sodium chloride and sodium sulfate, scattering prevention agents such as mineral oil emulsions, pH stabilizers such as disodium phosphate, and hard water softeners such as polyphosphates.

The reactive dye composition of the present invention is not particularly limited in its form, and may be in a known form, but may be in the form of powder, granule, or liquid. No problem.

The present invention also provides a method for dyeing and printing a fiber material, characterized by using the above reactive dye composition. Such fiber materials include, for example, natural cellulose fibers such as cotton, linen, hemp, jud and lami fibers, viscos staples, filament biscos.
Regenerated cellulose fibers such as cotton or a blend of these and other fibers, for example, a cotton / polyester blend, a cotton / nylon blend, a cotton / wool blend, and the like.

The dyeing or printing method of the present invention is characterized by using the above-mentioned reactive dye composition, and there is no particular limitation on other conditions and the like, and it can be carried out by, for example, a known method. As a method, for example,
In the case of the exhaust dyeing method, about 30 to 95 ° C. in the presence of an inorganic neutral salt such as anhydrous sodium sulfate and salt, and an acid binder such as sodium carbonate, caustic soda, and tertiary phosphate. , Preferably 40 to 7
A method of dyeing at about 0 ° C. is exemplified. In the cold pad batch dyeing method, padding is carried out using an inorganic neutral salt such as anhydrous sodium sulfate and sodium chloride, and an acid binder such as caustic soda and sodium silicate, and then placed in a closed packaging material at a constant temperature. A method of dyeing by leaving it to stand is exemplified. In the continuous dyeing method, an acid binder such as sodium carbonate and sodium bicarbonate is mixed with the dye padding solution,
A one-bath padding method of dyeing by drying or steaming after dye padding, and an inorganic neutral salt such as anhydrous sodium sulfate and salt after padding, and an acid binder such as caustic soda or silicate soda. Padding and dyeing by dry heat or steaming. Further, in the printing method, after printing a printing paste containing an acid binder such as sodium bicarbonate, a one-phase printing method in which printing is performed by drying or steaming, and printing a printing paste. After that, it contains an inorganic neutral salt such as sodium chloride and an acid binder such as caustic soda and silicate soda 90
For example, a two-phase printing method in which the material is charged into a high-temperature solution at a temperature of at least 100 ° C. to perform printing.

[0067]

The reactive dye composition of the present invention has a neutral to
Since it shows remarkably excellent solubility in all aqueous solutions of alkalinity, it can be used for dyeing or printing methods requiring particularly high solubility, such as exhaustion dyeing, padding and one-phase. Even in the printing method, uniform dyeings and prints without spots and the like can be obtained.

[0068]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In addition, in the text, parts represent parts by weight.

Example 1 The form of the free acid is represented by the formula (1)

[0070]

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85 parts of a bisazo compound represented by the following formula: sodium salt of a condensate of methylnaphthalenesulfonic acid and formaldehyde (sulfonation degree 110%, average condensation degree 1.
5) 14 parts and 1 part of a mineral oil emulsion were sufficiently mixed. 20 g of the obtained reactive dye composition was dissolved in 400 g of hot water and cooled to 25 ° C. To this, 15 ml of a 32.5% aqueous solution of caustic soda and 150 g of 50 degree water glass were added, and further water was added to adjust the total amount to 1000 ml at 25 ° C. Was padded. The padded cotton fabric is wound up, closed with a polyethylene film and left in a room at 20 ° C. for 20 hours, and then the cotton fabric is washed and soaped.
Finished dry. The obtained dyed product was a uniform navy dyed product without spots.

Example 2 The form of the free acid is represented by the formula (2)

[0073]

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89 parts of a bisazo compound represented by the following formula: sodium salt of a condensate of dimethylnaphthalenesulfonic acid and formaldehyde (degree of sulfonation 110%, average degree of condensation 1.
8) 5 parts, sodium salt of a condensate of monomethylnaphthalenesulfonic acid and formaldehyde (sulfonation degree 110
%, An average degree of condensation of 1.5) and 4 parts of a mineral oil emulsion were thoroughly mixed. 0.8 kg of the obtained reactive dye composition was dissolved in 16 kg of hot water, and water was added thereto to make 200 liters. After adding 10 kg of anhydrous sodium sulfate to this solution,
10 kg of non-mercerized cotton knit was immersed and heated to 60 ° C. Treat the cotton knit at the same temperature for 20 minutes,
4 kg of daash was added and the cotton knit was treated and dyed at this temperature for 60 minutes. The cotton knit was then washed and dried to finish. The resulting dyed product was uniform, dark and clear navy with no spots.

Example 3 The form of the free acid is represented by the formula (3)

[0076]

Embedded image

A sodium salt of a condensate of dimethylnaphthalenesulfonic acid and formaldehyde (sulfonation degree 110%, average condensation degree 1.
8) 6.5 parts, 7.5 parts of sodium salt of a condensate of naphthalenesulfonic acid and formaldehyde (degree of sulfonation 110%, average degree of condensation 1.8), 10 parts of sodium sulfate, and 1 part of mineral oil emulsion were sufficiently mixed. . 80 kg of the obtained reactive dye composition was dissolved in kg of hot water and cooled to 25 ° C. 1 kg of sodium alginate, 10 kg of sodium metanitrobenzenesulfonate and 20 kg of sodium bicarbonate
kg was added, and water was further added to make a total volume of 1000 liters at 25 ° C. Using this solution as a padding solution, cotton fabric was padded. The padded cotton fabric was dried at 120 ° C. for 2 minutes, then steamed at 100 ° C. for 5 minutes, washed, soaped, washed and dried to finish. The resulting dyed product was a uniform, dark, vivid navy dyed product without spots.

Example 4 The form of the free acid is represented by the formula (4)

[0079]

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65 parts of a bisazo compound represented by the following formula: sodium salt of a condensate of diethylnaphthalenesulfonic acid and formaldehyde (degree of sulfonation 100%, average degree of condensation 2.
5) 10 parts of sodium salt of monoethylnaphthalenesulfonic acid and formaldehyde condensate (degree of sulfonation: 120
%, Average degree of condensation 1.8) 24 parts and mineral oil emulsion 1
Parts were mixed well. A printing paste having the following formulation was prepared using the obtained reactive dye composition. Reactive dye composition 80 parts Urea 50 parts Sodium alginate 550 parts Hot water 300 parts Sodium bicarbonate 20 parts Total 1000 parts After printing the obtained printing paste on cotton poplin, 5% at 100 ° C.
A steaming treatment was performed for one minute. Next, after washing, soaping, and further washing, the product was dried and finished. The resulting print was a uniform, dark navy print without spots.

Example 5 (a) The free acid was of the formula (5)

[0082]

Embedded image

A sodium salt of a condensate of dimethylnaphthalenesulfonic acid and formaldehyde (sulfonation degree 110%, average condensation degree 1.
8) 20 parts of sodium salt of monomethylnaphthalenesulfonic acid and formaldehyde condensate (degree of sulfonation: 100
%, Average degree of condensation 1.8) 19 parts and mineral oil emulsion 1
Parts were mixed well. (B) Cellulose fiber 50% and polyester fiber 50
% Of the mixed and knitted fabrics was set in a high-pressure circular dyeing apparatus, the bath ratio was 1: 8, the water temperature was 80 ° C., and the pH was adjusted to 5 using acetic acid. Equation (6) sufficiently dispersed in advance

[0084]

Embedded image

A dispersion containing 0.2 parts of the disperse dye represented by the formula (1) was added, the temperature was raised to 130 ° C. in 40 minutes, and the temperature was maintained at the same temperature for 40 minutes to dye. (C) 0.8 kg of the reactive dye composition obtained in the item (a)
Was dissolved in boiling water, and water was added thereto to make 200 liters. To this solution was added 10 kg of anhydrous sodium sulfate, and (b)
10 kg of the dyed material obtained in
After treating the knitted fabric for 5 minutes, 4 parts of soda ash was added, and dyed at the same temperature for 60 minutes. The dyeing was then washed and dried to finish. The obtained dyed product was a uniform and dark navy dyed product without spots.

Examples 6 to 20 Instead of using the reactive dye compositions described in Examples 1 to 5, the reactive dye compositions shown in Tables 1 to 5 (in the tables, parts are parts by weight of each compound) ), And dyeing and printing were performed according to the methods described in Examples 1 to 5. The solubility of the reactive dye compositions shown in Tables 1 to 5 were all good. Further, the obtained dyed product and printed product were uniform and dark navy dyed product and printed product without any unevenness.

[0087]

[Table 1]

[0088]

[Table 2]

[0089]

[Table 3]

[0090]

[Table 4]

[0091]

[Table 5]

Example 21 The padding solution prepared in Example 1 was prepared at 25 ° C.
No precipitation of dye was observed after standing for 20 minutes.

Comparative Example 1 Bisazo compound (1) 85 used in Example 1
, 14 parts of anhydrous sodium sulfate and 1 part of a mineral oil emulsion were thoroughly mixed. A padding solution was prepared according to Example 1 except that 20 g of the obtained reactive dye composition was used, and a cotton fabric was padded in the same manner as in Example 1 to obtain a dyed product. The obtained dyed product was a navy dyed product having many spots and having no practical value.

Example 22 Bisazo compound (2) 84 used in Example 2
Parts, anhydrous sodium sulfate 5 parts, sodium salt of condensate of dimethylnaphthalenesulfonic acid and formaldehyde (degree of sulfonation 110%, average degree of polymerization 1.8), condensate of monomethylnaphthalenesulfonic acid and formaldehyde (degree of sulfonation 110 %, An average degree of polymerization of 1.5) and 5 parts of a mineral oil emulsion were thoroughly mixed. Obtained reactive dye composition 4
g was dissolved in 80 g of boiling water, and water was added thereto.
It was adjusted to 00 ml. 10 g of anhydrous sodium sulfate and 4 g of soda ash were added to this solution, and the mixture was allowed to stand at 25 ° C. for 60 minutes. No precipitation of dye was observed.

Example 23 In Example 22, the amount of sodium salt of a condensate of dimethylnaphthalenesulfonic acid and formaldehyde (sulfonation degree 110%, average polymerization degree 1.8) was changed to 7.5 parts, and monomethylnaphthalenesulfone was used. Condensate of acid and formaldehyde (degree of sulfonation 110%, average degree of polymerization 1.
A reactive dye composition was obtained according to Example 22, except that the amount of 5) was changed to 7.5 parts. 6 g of the obtained reactive dye composition was dissolved in 120 g of hot water, and water was added thereto to adjust the temperature to 25 ° C. and 200 ml. 10 g of anhydrous sodium sulfate and 4 g of soda ash were added to this solution, and the mixture was allowed to stand at 25 ° C. for 120 minutes, but no precipitation of dye was observed.

Comparative Example 2 In Example 22, the amount of anhydrous sodium sulfate was changed to 15 parts, and the sodium salt of a condensate of dimethylnaphthalenesulfonic acid and formaldehyde and the condensate of monomethylnaphthalenesulfonic acid and formaldehyde were not used. Except for the above, a reactive dye composition was obtained in accordance with Example 22. 3 g of the obtained reactive dye composition was dissolved in 60 g of boiling water, and water was added thereto to adjust the temperature to 25 ° C. and 200 ml.
10 g of anhydrous sodium sulfate and 4 g of soda ash were added to this solution,
When left at 5 ° C., precipitation of the dye was observed in 20 minutes.

Comparative Example 3 To 98 parts of the bisazo compound (1) used in Example 1, 2 parts of a mineral oil emulsion was added and mixed well. (A) A padding solution was prepared according to Example 1, except that 20 g of the obtained reactive dye composition was used. Immediately after the preparation, no precipitation of the dye was observed, but the viscosity became extremely high. Even when padding a cotton fabric using this solution, only a very lightly colored dyed product was obtained. . (B) When the padding solution of (a) was left at 25 ° C. for 30 minutes, it became a gel and became incapable of padding.

Example 24 Bisazo compound (1) 65 used in Example 4
Parts, a sodium salt of a condensate of naphthalenesulfonic acid and formaldehyde (sulfonation degree: 180%, average polymerization degree: 1.1), and 1 part of a mineral oil emulsion were sufficiently mixed. Except for using 80 parts of the obtained reactive dye composition,
A printing paste was prepared in accordance with Example 4 and subjected to a printing treatment in the same manner as in Example 4. As a result, the resulting printed matter was a spotless navy dyed matter.

Example 25 Bisazo compound (1) 85 used in Example 1
And 15 parts of a sodium salt of a condensate of methylnaphthalenesulfonic acid and formaldehyde (degree of sulfonation 110%, average degree of polymerization 1.8) were sufficiently mixed. A padding solution was prepared according to Example 1 except that 20 g of the obtained reactive dye composition was used, and a cotton fabric was padded in the same manner as in Example 1 to obtain a dyed product. The obtained dyed product was a navy dyed product without spots.

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[Procedure amendment]

[Submission date] December 17, 1996

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0009

[Correction method] Change

[Correction contents]

(Where R⁷, R⁸, R⁹And R^TenIs
Independently, a hydrogen atom or an optionally substituted lower
Killed, optionally substituted phenyl or substituted
May represent naphthyl, Q^TwoIs -CH_Two-, -O-,
-S-, -SO_Two-Or -NR ¹¹-, Where R¹¹
Represents a hydrogen atom or an optionally substituted lower alkyl.
And t represents 1, 2 or 3. Y is substituted
Optionally substituted phenylene or optionally substituted low phenylene
Z represents a lower alkylene;¹And Z^TwoAre independent of each other,
-CH = CH_Two, -CH_TwoCH_TwoL or -CH_TwoCH_Two
Represents OH, wherein L is a group capable of leaving by the action of an alkali
Represents, Z¹, Z ^TwoIs -CH_TwoCH_TwoO
H, the other is -CH = CH_TwoOr -CH_TwoCH
_TwoL. Or a salt thereof.
And (b) the condensation of naphthalenesulfonic acids and formaldehyde
A reactive dye composition comprising:
And method of dyeing or printing fiber material using the sameOfferOffer
Things. Hereinafter, the present invention will be described in detail.

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0015

[Correction method] Change

[Correction contents]

[Wherein p is 1 or 2, q is 0 or 1, r
Represents 0 or 1, and the bond indicated by * represents a bond leading to —NR ¹ — in formula (I). ] Ki represented out to include groups such as, in particular,

[Procedure amendment 3]

[Document name to be amended] Statement

[Correction target item name] 0028

[Correction method] Change

[Correction contents]

[0028] The general formula (X1), (X3) and in the group represented by (X4), as phenyl optionally have substitution of <br/> in R ^7, R ^8, R ⁹ and R ¹⁰ are For example, halogeno such as chloro and bromo, alkyl having 1 to 4 carbons, 1 carbon
~ 4 alkoxy, sulfo, carboxy, hydroxy,
Substituted by one or two substituents selected from the group consisting of cyano, carbamoyl, sulfamoyl, carboxylic acid ester, 2-hydroxyethylsulfonyl, amino, acylamino, and amino substituted by alkyl having 1 to 4 carbon atoms. Phenyl and the like.

[Procedure amendment 4]

[Document name to be amended] Statement

[Correction target item name] 0030

[Correction method] Change

[Correction contents]

[0030] The general formula (X1), (X3) and in the group represented by (X4), as R ^7, R ^8, R ⁹ and naphthyl which may have been replacement of <br/> in R ¹⁰ is For example, halogeno such as chloro and bromo, alkyl having 1 to 4 carbons, 1 carbon
And naphthyl which may be substituted by one, two or three substituents selected from the group consisting of alkoxy, sulfo, carboxy and hydroxy.

[Procedure amendment 5]

[Document name to be amended] Statement

[Correction target item name] 0053

[Correction method] Change

[Correction contents]

In this condensation reaction, the order of condensation of each compound is not particularly limited, but when the amine compound represented by the general formula (VII) is an aliphatic amine, this is first or secondly. Is preferably condensed. The conditions of the condensation reaction are not particularly limited. For example, the first condensation reaction is performed at a temperature of −10 ° C. to + 40 ° C.
Performed under conditions of pH 1 to 10, the second condensation reaction is
Carried out at a temperature of 0 ° C to 70 ° C and a pH of 2 to 10,
The third condensation reaction is performed at a temperature of 10 ° C to 100 ° C and a pH of 2 to
Conditions performed under the conditions of No. 9 can be exemplified .

[Procedure amendment 6]

[Document name to be amended] Statement

[Correction target item name] 0077

[Correction method] Change

[Correction contents]

A sodium salt of a condensate of dimethylnaphthalenesulfonic acid and formaldehyde (sulfonation degree 110%, average condensation degree 1.
8) 6.5 parts, 7.5 parts of sodium salt of a condensate of naphthalenesulfonic acid and formaldehyde (degree of sulfonation 110%, average degree of condensation 1.8), 10 parts of sodium sulfate, and 1 part of mineral oil emulsion were sufficiently mixed. . 80 kg of the obtained reactive dye composition was dissolved in 160 kg of hot water and cooled to 25 ° C. 1 kg of sodium alginate, 10 kg of sodium metanitrobenzenesulfonate and 2 kg of sodium bicarbonate
0 kg, water is further added, and the total amount is 1000 at 25 ° C.
Liter, and the cotton fabric was padded using this solution as a padding solution. Padded cotton fabric at 120 ° C
After drying at 100 ° C. for 5 minutes, washing and soaping were performed, followed by washing and drying to finish. The resulting dyed product was a uniform, dark, vivid navy dyed product without spots.

[Procedure amendment 7]

[Document name to be amended] Statement

[Correction target item name] 0097

[Correction method] Change

[Correction contents]

Comparative Example 3 To 98 parts of the bisazo compound (1) used in Example 1, 2 parts of a mineral oil emulsion was added and mixed well. (B) except that there use the resulting reactive dye composition 20g is
A padding solution was prepared according to Example 1. It is not observed precipitation of the dye immediately after preparation, but the viscosity is significantly high. Even when padding a cotton fabric using this solution, only a very lightly colored dyed product was obtained. . (B) When the padding solution of (a) was left at 25 ° C. for 30 minutes, it became a gel and became incapable of padding.

Claims (6)

[Claims] (1) the free acid is represented by the following general formula (I):Wherein A is phenylene which may be substituted or
Optionally substituted naphthylene, wherein B is substituted
R also represents phenylene;¹And R^TwoAre independent of each other
A hydrogen atom or a lower alkyl which may be substituted
X is an optionally substituted pyridinio, one of the following:
General formula (X1), (X2), (X3) or (X4)(Where R⁷, R⁸, R⁹And R^TenAre independent of each other,
Hydrogen atom, lower alkyl which may be substituted,
Optionally substituted phenyl or optionally substituted naph
Represents chill and Q^TwoIs -CH_Two-, -O-, -S-, -S
O_Two-Or -NR ¹¹-, Where R¹¹Is a hydrogen atom or
Represents an optionally substituted lower alkyl, t is 1,
Represents 2 or 3. And Y is optionally substituted
Phenylene or optionally substituted lower alkylene
And Z¹And Z^TwoAre independently of each other -CH = CH
_Two, -CH_TwoCH_TwoL or -CH_TwoCH_TwoOH,
Here, L represents a group capable of leaving by the action of an alkali,
Z¹, Z ^TwoIs -CH_TwoCH_TwoOH
The other is -CH = CH_TwoOr -CH_TwoCH_TwoL
You. And (b) condensation of naphthalenesulfonic acids and formaldehyde
A reactive dye composition comprising:
Stuff. 2. A bisazo compound of (a) or a salt thereof,
The weight composition ratio (a) :( b) of the condensate of (b) is 2:
The reactive dye composition according to claim 1, wherein the ratio is from 8 to 9.8: 0.2. 3. The condensate of (b), wherein the naphthalenesulfonic acids are substituted with 1 to 3 substituents selected from the group consisting of alkyl having 1 to 3 carbon atoms. 3. The reactive dye composition according to any one of claims 1 to 2. 4. The reactive dye composition according to claim 1, wherein the degree of sulfonation of the alkylnaphthalenesulfonic acids in the condensate of (b) is 50 to 150%. 5. The condensate of (b) has an average degree of condensation of from 1.1 to 1.1.
The reactive dye composition according to any one of claims 1 to 4, which is 3. 6. A method for dyeing or printing a fiber material, comprising using the reactive dye composition according to claim 1.