JPS6023453A - Reactive dye composition and dyeing of textile material using the same - Google Patents

Abstract

PURPOSE:To provide a dye composition containing two or more kinds of monoazo compounds having different solubilities, and giving a uniformly dyed product having sufficient color density and free from spots, in high reproducibility by any dyeing methods. CONSTITUTION:A composition containing (A) at least one monoazo compound (or its metal salt) of formula I [D is phenyl substituted with 1-3 CH3, halogen, NO2, etc. or naphthyl (substituted with 1-2 SO3H); A is phenylene (substitued with 1-2 C2H5, Cl, OCH3, etc.) or naphthylene (substituted with one SO3H); X is -SO2CH=CH2 or -SO2CH2Y (Y is group eliminable with alkali); Z is halogen] and (B) at least one monoazo compound (or its metal salt) of formula II(R is 1-4C alkyl or substituted alkyl). The weight ratio of A:B is preferably 80:20-20:80.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a reactive dye composition that has excellent dyeability on textile materials and a method for dyeing textile materials using the same.

Dyeing of fiber materials such as cellulose fibers with reactive dyes includes exhaust dyeing method, -bath/padding/rolling method, -bath/
Semi-continuous or continuous dyeing methods such as padding and steaming methods, or textile printing methods are used.

When a reactive dye is used in an exhaust dyeing method, it is necessary to have sufficient solubility in a solution containing a large amount of electrolyte and alkali.

Furthermore, when the reactive dye is used in semi-continuous or continuous dyeing methods and printing methods, it is necessary that it has sufficient solubility in an aqueous alkaline solution.

On the other hand, as the solubility of the dye increases, its directness to the fiber material tends to decrease, and when using the exhaust dyeing method, there is a problem that the dyeability decreases.

The inventors of the present invention have conducted intensive studies to develop reactive dyes that can produce uniform, spot-free dyed products of sufficiently high density with good reproducibility regardless of the dyeing method used. The present inventors have discovered that a reactive dye composition containing a mixture of dyes can achieve the object, and have completed the present invention.

That is, the present invention relates to the following general formula (11 (where D is a group of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a halogen, an acetylamino group, a propionylamino group, a nitro group, a sulfonic acid group, and a carboxyl group) selected from
It represents a phenyl group substituted with 1, 2 or 8 substituents, or a naphthylene group optionally substituted with 1 to 2 sulfonic acid groups. A is one phenylene residue or sulfonic acid group optionally substituted with one or two substituents selected from the group of methyl group, ethyl group, methoxy group, ethoxy group, chlorine, bromine, and sulfonic acid group Naphthylene residues optionally substituted with X Ha!
-8020Ei = CH2 or group -8OzCK2(J
Represents hY. Here, Y is a group that is eliminated with an alkali. 2 represents a halogen atom. ) and one or more monoazo compounds or metal salts thereof represented by the following general formula (Ill (where D, A,
and 2 have the meanings given above, and the pores are alkyl groups having 1 to 4 carbon atoms, hydroxy-substituted alkyl groups, cyano-substituted alkyl groups, alkoxy-substituted alkyl groups, halogen-substituted alkyl groups, carboxy-substituted alkyl groups, carbamoyl Represents a substituted alkyl group, an alkoxycarbonyl-substituted alkyl group, or a sulfo-substituted alkyl group. ) A reactive dye composition containing one or a mixture of two or more of the monoazo compounds or metal salts thereof, and a method for dyeing delicate materials characterized by using the reactive dye composition.

The monoazo compound represented by the above general formula fIl or its metal salt is, for example,
89672 or Japanese Patent Publication No. 57-42986, and since the solubility in solutions containing a large amount of electrolyte and alkali or in aqueous alkaline solutions tends to be generally low, it is possible to avoid spotting by any of the above-mentioned dyeing methods. It may be difficult to obtain uniform dyeings.

On the other hand, the monoazo compound represented by the above general formula (Ill) or its metal salt generally has superior solubility compared to the monoazo compound shown by the above general formula (1) or its metal salt, and therefore is semi-continuous or While it is possible to obtain a uniformly dyed product without spots using the continuous dyeing method or the textile printing method, it may be difficult to obtain a sufficient dye finish when using the exhaust dyeing method.

The compounds represented by the above general formula and (nl) can be produced, for example, as follows.

An aromatic amine represented by the following general formula (1111 % formula % (] - (in the formula has the above-mentioned meaning)) is diazotized by a conventional method in an aqueous medium to form l-amino-8-hydroxy. Naphthalene
A coupling reaction was carried out with an N-acylated product of 3,6-disulfonic acid or l-amino-8-hydroxynaphthalene-4,6-disulfonic acid at a temperature of 0°C to 80°C while adjusting the pH to 5 to 9. Thereafter, the anlu group is hydrolyzed at a temperature of 50°C to 100°C in the presence of an acid or an alkali to obtain a monoazo compound represented by formula ([V)].

(In the formula, D has the above-mentioned meaning.) Then, the formula compound is heated in an aqueous medium at a temperature of θ°C to 30°C.
While adjusting the pH from piiH to 7 at ℃, the dichlorotriazinyl compound is firstly condensed with cyanuric chloride, and then the general formula (Vl or (■)) (wherein R, A, and X are ) is secondarily condensed at a temperature of 80° C. to 60° C. while adjusting the pH to 4 to 7 to obtain a compound of the general formula (moon or general formula side). be able to.

Alternatively, a compound of the general formula ffl or Also, by secondary condensation of a monoazo compound of the general formula←V while adjusting the pH to 7 or 7, the general formula
can be obtained.

Alternatively, l-amino-8-hydroxynaphthalene-8
, 6-disulfonic acid or 1-amino-8-hydroxynaphthalene-4,6-disulfonic acid and the formula tv+ or (V
The compounds of I) are added in any order in an aqueous medium - secondly to a pH of 4 at a temperature of 20°C to 60°C, with adjustment to pIli3 to pEI7 at a temperature of 0°C to 30°C.
Condensation with cyanuric chloride while adjusting the pH to 7 to obtain a monochlorotriazinyl compound represented by the general formula (vII) or (wherein, R, A, and X have the above-mentioned meanings), followed by The general formula (Il
Alternatively, a compound of the general formula fill can be obtained.

Examples of the diazo component represented by the general formula (III) include: 2-aminebenzenesulfonic acid 2-amino-5-methylbenzenesulfonic acid 2-amino-5-ethylbenzenesulfonic acid 2-amino-5-methquinbenzene Sulfonic acid 2-amino-5-ethynebenzenesulfonic acid 2-amino-5-chlorobenzenesulfonic acid 2-amino-5-promobenzenesulfonic acid-2
-Amino-5-acetylaminobenzenesulfonic acid 2-amino-5-probionylaminobenzenesulfonic acid 2-amino-5-nitropennesulfonic acid 2-amino-4-chloro-5-methylbenzenesulfonic acid 2-amino -5-chloro-4-methylbenzenesulfonic acid 2-amino-4-methoxybenzenesulfonic acid 2-amino-4-ethoxybenzenesulfonic acid 3-amino-4-
Methylbenzenesulfonic acid 3-amino-4-ethylbenzenesulfonic acid 3-amino-4-methoxybenzenesulfonic acid 3-amino-4-ethoxybenzenesulfonic acid 8-amino-4-chlorobenzenesulfonic acid 8-amino- 4-bromobenzenesulfonic acid 4-7J/-8-methylbenzenesulfonic acid 4-7E/-8-ethylbenzenesulfonic acid 4-amino-3-methoxybenzenesulfonic acid 4-amino-8-ethoxybenzenesulfonic acid 4-amino -8-Chlorobenzenesulfuric acid 4-amino-3
-Nitrobenzenesulfonic acid 2-aminebenzene-1,
4-disulfonic acid 2-aminobenzene-1,5-disulfonic acid 2-aminobenzoic acid 2-amino-4-methquinenzoic acid 2-amino-5-methoxybenzoic acid 2-amino-4-acetylaminobenzoic acid 2- Amino
5-acetylaminobenzoic acid 2-amino-4-sulfobenzoic acid 2-amino-5-sulfobenzoic acid 4-amino-2,5-dimethylbenzenesulfonic acid 4-amino-2,5-diethylbenzenesulfonic acid 4-amino-2,5-dimethynebenzenesulfonic acid 4-amino-2,5-diethylbenzenesulfonic acid 4-amino-2,5-dichlorobenzenesulfonic acid 4-amino-2,5-dibromobenzenesulfonic acid 4 -amino-2-methyl-5-methoxybenzenesulfonic acid 4-amino-2-methyl-5-ethoxybenzenesulfonic acid 2-amino-5-methylbenzene-1,4-disulfonic acid 2-amino-5-ethylbenzene- 1,4-disulfonic acid 2-amino-5-methylbenzene-1,4-disulfonic acid 2-amino-5-methylbenzene/-1,4-disulfonic acid 2-amino-5-acetylaminobenzene 1.4 -Disulfonic acid 2-amino-5-propionylaminobenzeno 1.4-
Disulfonic acid 2-naphthylamino-1-sulfonic acid 2-naphthylamine-5-sulfonic acid 2-naphthylamino-6-sulfonic acid 2-naphthylamine-7-sulfonic acid 2-naphthylamine-8-sulfonic acid 2-naphthylamino-1 , 5-disulfonic acid 2-naphthylamine-1,6-disulfonic acid 2-naphthylamine epsilon 1,7-disulfonic acid 2-naphthylamine-4,8-disulfonic acid 2-naphthylamine-6,8-disulfonic acid 2-naphthylamine -3,6-disulfonic acid and the like can be mentioned.

In the reaction component represented by general 2), examples of substituents for the compound of general formula <11 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 5eC-
Butyl group, hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 8-hydroxypropyl group, 2-hydroxybutyl group, 4-hydroxybutyl group, 1-methyl-2-hydroxypropyl group, cyanomethyl group, cyanethyl group, methoxymethyl group, 2-methoxyethyl group, 3-methoxypropyl group, ethoxymethyl group, 2-ethoxyethyl group, chloromethyl group, 2-chloroethyl group, 8-chloropropyl group, 4-chlorobutyl group, carboxynemethyl group, 2-carboxyneethyl group,
Carbamoylmethyl group, 2-carbamoylethyl group, 2
-Methoxycarbonylethyl group, 2-ethquincarbonylmethyl group, sulfomethyl group, 2-sulfoethyl group, etc., and are represented by the general formula y) or (4).As the formula residue A, for example, C□3 2Hs ■ (In the formula, the bond shown with an asterisk is H-N- or ■IN
- means a bond that leads to a group. ), etc.

and X is the group -80zCH=OHz or the group -802
It represents 0HzOH2Y, where Y is a group that is eliminated with an alkali, such as a sulfate ester group, a phosphate ester group, an acetate ester group, a halogen atom, etc.

These compounds can also be synthesized individually,
It can also be synthesized by mixing reaction components represented by the general formula (Vl or (Vll) in a desired ratio.

As described above, the reactive dye composition of the present invention contains a mixture of at least one compound each of a compound represented by the general formula (I+) and a compound represented by the general formula tn+, which have different solubility. (11) and the general formula (Il
The mixing ratio with the compound indicated by l is 80:20 by weight.
to 20:80.

The reactive dye composition of the present invention may further contain a hydrotope such as urea or anthraquinone-2-sulfonic acid, a condensate of alkylnaphthalene sulfonic acid and formaldehyde, or a substance that does not affect solubility such as textrin or sugar. It can also contain electrolytes in small amounts that do not adversely affect solubility, anti-scattering agents such as mineral oil emulsions, pI (stabilizers such as disodium phosphate) and water softeners such as polyphosphates. Additions such as these are prohibited.

The reactive dye composition according to the invention can be advantageously applied to dyeing and printing materials consisting of cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers and leather.

Cellulose fibers are preferably exemplified by cotton and regenerated cellulose, but also include other vegetable fibers such as linen, hemp, and jute. Polyamide fibers include natural and synthetic fibers such as wool and other animal hairs, silk, polyamide-6,
6, polyamide-6, polyamide-111 or polyamide-4.

Dyeing and printing of these fiber materials are carried out by conventional methods commonly used for reactive dyes, such as conventional exhaust dyeing, semi-continuous or continuous dyeing, or printing. In the case of exhaustion method, sodium carbonate, tribasic phosphate,
It is carried out at relatively low temperatures in a dye bath containing mirabilite or common salt in the presence of an acid binder such as caustic soda. Dyeing by a textile printing method is also carried out by printing a color paste containing an acid binder such as bicarbonate of soda, soda carbonate, tribasic sodium phosphate, or caustic soda, urea, and a sizing agent, preferably sodium alginate, etc. on the fiber, and after intermediate drying, the dyeing is carried out at 100 to 200°C. This is done by steaming or dry heating. Further, a semi-continuous or continuous dyeing method is also carried out by a commonly used method.

The novel compositions according to the invention are particularly useful for dyeing and printing cellulose fibers. It also shows excellent physical and chemical stability in dyeing stock liquids and printing paste liquids and in the presence of alkali, and has very good affinity and excellent build-up properties in ordinary dyeing and printing. However, even in exhaust dyeing, it is relatively unaffected by the bath ratio, dyeing temperature, etc., and provides a rich dyed product with excellent build-up properties.

The dyed or printed products obtained by the composition of the present invention have high tinting strength and excellent gloss, and are excellent in various fastnesses, especially chlorine fastness, light fastness, and sweat/sunlight fastness.

Next, the present invention will be explained by examples. In the text, parts indicate parts by weight.

Example 1 (a) 9.2 parts of cyanuric chloride is added to a solution of 0.1 part of noniono surfactant dissolved in 100 parts of water at 0 to 5°C and dispersed.

To this, 1-amino-8-hydroxynaphthalene-3,6
- 16 parts of disulfonic acid (■ acid) in 100 parts of water, pH 7~
The solution dissolved in step 8 is added dropwise at 0 to 5°C over 1 hour. After dropping, add 20% sodium carbonate aqueous solution and
and stir for an additional 2 hours. Next, 16 parts of l-N-ethylaminobenzene-3-β-hydroxyethylsulfone sulfate was added, and the temperature was raised to 40°C while adjusting the pH to 6 to 6 with a 20% aqueous sodium carbonate solution, and the mixture was stirred at the same temperature for 6 hours. .

Next, add 12.6 parts of sodium 0-b to the blade again. A solution obtained by diazotizing 8.6 parts of 2-aminebenzenesulfonic acid in a conventional manner is added to this at 0 to 5°C over 1 hour. After stirring at the same temperature for 2 hours, the pH was adjusted to 5 to 6 with hydrochloric acid, and 40 parts of sodium chloride was added to precipitate crystals, which were filtered with suction, washed, and dried at 60°C to form the following formula (1). Compound 80aNa
5OaNa (λmaz '53 Q nm) (b) 9.2 parts of cyanuric chloride is added to 1 part of a solution of 0.1 part of nonionic surfactant dissolved in 100 parts of water at 0 to 5°C and dispersed.

To this, l-amino-8-hydroxynaphthalene-8,
16 parts of 6-disulfonic acid (H acid) was added to 100 parts of water at pI (
The solution dissolved in steps 7 to 8 is added dropwise at 0 to 5°C over 1 hour. After dropping, add 20% aqueous sodium carbonate solution to pH 3.
and stir for an additional 2 hours.

Next, 16 parts of l-aminobenzene-8-β-hydroxyethylsulfone sulfate were added, and the mixture was heated to 40°C while adjusting the pH to 5 to 6 with a 20% aqueous sodium carbonate solution, and stirred at the same temperature for 6 hours.

Then, after cooling again to 0-5° C., 12.6 parts of sodium hydrogen carbonate are added. To this was added a solution obtained by diazotizing 8.6 parts of 2-amizbenzenesulfuric acid in a conventional manner.
Add for 1 hour at 5°C. After stirring at the same temperature for 2 hours, the pH was adjusted to 5 to 6 with hydrochloric acid, and 40 parts of sodium chloride was added to precipitate crystals, which were filtered with suction, washed, and dried at 60°C to form the following formula (2). The compound was obtained.

5OaNa 803Na (λmax 580 nm) (/included) 60 parts of the compound represented by formula (1) and formula (2)
30 parts of the compound represented by (30 parts) and 10 parts of naphthalene sulfonic acid formaldehyde condensate were uniformly mixed to prepare 100 parts of dye composition A.

b)) 0.8 parts of dye composition A was dissolved in 200 parts of water, and 20 parts of anhydrous sodium sulfate was added to prepare a dye bath. 10 parts of cotton knit was immersed in this bath and heated to 60°C, then 4 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes. After dyeing,
After washing with water and soaping, a dyed product with a high density of red was obtained. (1 tbsp) Dissolve 50 parts of dye composition A in 700 parts of water,
Add 1'50 parts of 2.5% caustic soda soluble in water, 15- and 50-degree Baume water glass, add 100% chlorinated water,
A dye bath of t 1' 000 parts was prepared. A cotton fabric was padded using this bath, rolled up, sealed with a polyethylene film, and left in a room at 20°C for 20 hours. The dyed fabric was washed with water and soaped to obtain a dyed fabric with a high density of red.

Dissolve 50 parts of N dye composition A in 700 parts of water.
20 parts of sodium m-nitropenzenosulfonate, 1 part of sodium alginate, and 20 parts of sodium bicarbonate were added, and water was further added to prepare a dye bath having a total amount of 1000 parts. A cotton fabric is padded using this bath, dried with hot air at 180'C for 1 minute, then steam-nogged with a steamer at 108°C for 3 minutes, washed with water, and soaped to obtain a dyed fabric with a high density of red. Ta.

g) Dissolve 5 parts of dye composition A in 80 parts of water, add 5 parts of urea
1 part, 58 parts of original glue paste, 2 parts of sodium bicarbonate, and further water were added to prepare a colored paste paste with a total amount of 100 parts.

Using this color paste, print on cotton fabric, dry at 103℃
After steaming for 5 minutes using a steamer, washing with water and soaping were performed to obtain a dyed product with a high density of red.

Comparative Example-1 90 parts of the compound represented by formula (1) obtained in (a) of Example 1 was uniformly mixed with 10 parts of naphthalene sulfonate formaldehyde condensate to prepare 100 parts of dye composition B. .

As a result of dyeing using 013 parts of dye composition B under the same conditions as in item (d) of Example 1, only dyed products with extremely low density were obtained as shown in the table below.

The degree of dyeing in the table was calculated from the surface concentration of the dyed product using the above formula.

Comparative Example-2 90 parts of the compound represented by formula (2) obtained in (b) of Example 1 was uniformly mixed with 10 parts of naphthalene sulfonic acid formaldehyde condensate to prepare 100 parts of dye composition 0. .

As a result of dyeing using 00.3 parts of the dye composition under the same conditions as in Example 1, a red dyed product with relatively high density was obtained. ) The dyeing concentration was lower than that of the dyed products in section ).

As a result of dyeing using dye composition C under the same conditions as those in Example 1, items 1), 2), and 3), dyed products with extremely low density or with extremely large spots were found which were of no practical value. I could only get it.

The degree of dyeing in the table is the same as Comparative Example 1.

Example 2 (a) 9.2 parts of cyanuric chloride is added to a solution in which 0.1 part of a nonionic surfactant is dissolved in 100 parts of water at 10 to 15°C and dispersed. This was followed by l-N-ethylaminobenzene-4-β-hydroxyethylsulfone sulfate 7.
5 parts and 7.5 parts of l-aminobenzene-4-β-hydroxynystyl sulfonic acid sulfate in 100 parts of water.
The solution dissolved in H4-5 is added dropwise at 10-15°C over 1 hour. After the dropwise addition is completed, a 20% aqueous sodium carbonate solution is added to adjust to plT-3, and the mixture is further stirred for 2 hours. Next, 16 parts of H acid was added, and the pH was adjusted with a 20% aqueous sodium carbonate solution.
The temperature was raised to 40° C. while adjusting the temperature to 5 to 6, and the mixture was stirred at the same temperature for 2 hours.

Then, after cooling to 0-5°C, sodium hydrogen carbonate 12
．． Add 6 parts. A solution obtained by diazotizing 8.6 parts of 2-aminobenzenesulfonic acid using a conventional method was added to this at 0 to 5°C.
Add it in an hour. After stirring at the same temperature for 2 hours, the pH was adjusted to 5 to 6 with hydrochloric acid, 60 parts of sodium chloride was added to precipitate crystals, filtered under suction, washed, and dried at 60°C. ) and a mixed compound of the following formula (4) were obtained.

205 ku (λmax 53Q nm) (b) 90 parts of the mixture of compounds represented by formula (3) and formula (4) obtained in (a) were uniformly mixed with 10 parts of Glauber's salt, and 100 parts of dye composition D was added. It was adjusted.

Using the rXl dye composition, Section 1)) of Example-1.

As a result of dyeing under the same conditions as in (E), (F), and (G), dyed products with high red density were obtained in all cases.

Example-3 (a) 31.9 parts of H acid was added to 150 parts of water with caustic soda.
After dissolving at H6-7, add 8.4 parts of sodium bicarbonate. Add 20 to 9.8 parts of maleic anhydride to this solution.
The mixture was added at a temperature of 25°C and stirred at the same temperature for 1 hour.

Next, the solution was cooled to 5-10°C, and 20%
Add while maintaining pH 5-6 with aqueous sodium carbonate solution. After stirring at the same temperature for 8 hours, 6.0 parts of caustic soda was added and the temperature was raised to 80°C. The mixture is kept at the same temperature for 4 hours, then neutralized with hydrochloric acid to pH 5 to 7, and then 15% of the liquid volume of sodium chloride is added to precipitate crystals, followed by filtration to obtain a compound represented by the following formula.

9.3 parts of cyanuric chloride are added to a solution in which 28 parts of this compound is dissolved in 500 parts of water, and the mixture is stirred for 2 hours at a temperature of 5 to 10° C. while maintaining a pfi of 4 to 5 with a 20% aqueous sodium carbonate solution.

Subsequently, 1-N-hydroxyethylaminobenzeno-3
16 parts of -β-hydroxyethyl sulfone sulfate are added, and the temperature is raised to 50° C. while adjusting the pH to 5 to 61 with a 20% aqueous sodium carbonate solution, and the mixture is stirred for 6 hours at the same temperature.

Next, 40 parts of sodium chloride was added to precipitate crystals, which were filtered by suction, washed, and dried at 60°C to give the following formula (5
) was obtained.

(λmax 5801m) (b) 9.2 parts of cyanuric chloride is added to a solution in which 0.1 part of a noniono surfactant is dissolved in 100 parts of water at 10-15°C and dispersed. To this, 1-aminobenzene-2-β-
15 parts of hydroxyethylsulfone sulfate 10 parts of water
A solution prepared by dissolving 0 parts at pH 4 to 5 is added dropwise at 10-15°C over 1 hour. After the dropwise addition is completed, a 20% aqueous sodium carbonate solution is added to adjust the pH to 8, and the mixture is further stirred for 2 hours. Next, add 16 parts of acid, and dilute with 20% sodium carbonate aqueous solution.
While adjusting H to 5-6, the temperature was raised to 40℃, and at the same temperature
Stir for an hour.

Then, after cooling to 0-5°C, sodium hydrogen carbonate 12
．． Add 6 parts. A solution obtained by diazotizing 8.6 parts of 2-aminebenzenesulfonic acid in a conventional manner was added to this at 0 to 5°C.
Add it in an hour. After stirring at the same temperature for 2 hours, the pH was adjusted to 5 to 6 with hydrochloric acid, and 60 parts of sodium chloride was added to precipitate crystals, which were filtered under suction, washed, and dried at 60°C. The compound was obtained.

■ (λmax530nrn) rXl 30 parts of the compound represented by formula (5) and formula (6)
Dye composition E was prepared by uniformly mixing 60 parts of the compound represented by , 9 parts of anhydrous sodium sulfate, and 1 part of mineral oil emulsion.

2)) Using dye composition E, 2)) of Example-1, -
As a result of staining under the same conditions as in Sections ), (F), and (G), dyed products with high red color density were obtained in all cases.

Example-4 (a) Using the same method as in Example-1, the following formula (71, f81
, (91 and (10) were obtained.

5OaNa 803Na (mouth j 85 parts of the compound represented by formula (7), 15 parts of the compound represented by formula (8), 15 parts of the compound represented by formula (9)
1 part, 25 parts of the compound represented by formula (10), 1 part of anhydrous sodium sulfate, and 1 part of mineral oil emulsion were added and thoroughly mixed to prepare dye composition E.

rll Using dye composition r, Section 2) of Example-1,
As a result of staining under the same conditions as in Sections (A), (F), and (G), highly concentrated red dyes were obtained in all cases.

Comparative Example-8 Single compounds represented by formulas (3) to (9) of Examples-2 to 4 were added to Example-1-1, part 1, ii)), 匝), and (F) As a result of staining under the same conditions as in Section 1, each staining method yielded dyed products with significantly different densities.

The results of Examples 2 to 4 and Comparative Example 3 are summarized in the following table.

Claims (3)

[Claims] (1) The following general formula (Il (wherein D is selected from the group of methyl group, ethyl group, methoxy group, ethoxy group, halogen, acetylamino group, propionylamino group, nitro group, sulfonic acid group, and carboxyl group) , l, represents a phenyl group substituted with 2 or 8 substituents or a naphthylene group optionally substituted with 1 to 2 sulfonic acid groups.A is a methyl group,
Substituted with one phenylene residue or one sulfonic acid group optionally substituted with one or two substituents selected from the group of ethyl group, methoxy group, ethoxy group, chlorine, bromine, and sulfonic acid group It represents a good aftylene residue. X is a group -80zOH-Cfiz or a group '-8Oz
Represents OHzCHzY. Here, Y is a group that is eliminated with an alkali. 2 represents a halogen atom. ) or two or more of the monoazo compound or its metal salt represented by the following general formula +l1l (where D, 'A, X
and 2 have the meanings given above, and the pores are alkyl groups having 1 to 4 carbon atoms, hydroxy-substituted alkyl groups, cyanogen-substituted alkyl groups, alkoxy-substituted alkyl groups, halogen-substituted alkyl groups, carboxy-substituted alkyl groups, carbamoyl Represents a substituted alkyl group, an alkoxycarbonyl-substituted alkyl group, or a sulfo-substituted alkyl group. ) A reactive dye composition containing one or a mixture of two or more monoazo compounds or metal salts thereof. (2) The weight ratio of one or more monoazo compounds or metal salts thereof represented by the general formula (month) to one or more monoazo compounds or metal salts thereof represented by the general formula (II) 80:20 to 20:80. The reactive dye composition according to claim (1). (3) The following general formula [11 (wherein D is selected from the group of methyl group, ethyl group, methoxy group, ethoxy group, halogen, acetylamino group, propionylamino group, nitro group, sulfonic acid group, and carboxyl group) , represents a phenyl group substituted with 1.2 or 8 substituents or a naphthylene group optionally substituted with 1 to 2 sulfonic acid groups. A is a methyl group,
Substituted with one phenylene residue or one sulfonic acid group, which may be substituted with one or two substituents selected from the group of ethyl group, methoxy group, ethoxy group, chlorine, bromine, and sulfonic acid group. Represents an optional naphthylene residue. X is the group -8020H-CL (2 or the group -8O20H
Represents zCH2Y. Here, Y is a group that is eliminated with an alkali. 2 represents a halogen atom. ) and one or more monoazo compounds or metal salts thereof, and the following general formula (wherein D, A, X and 2 have the above meanings, It represents an alkyl group, a hydroxy-substituted alkyl group, a cyano-substituted alkyl group, an alkoxy-substituted alkyl group, a halogen-substituted alkyl group, a carboxy-substituted alkyl group, a carbamoyl-substituted alkyl group, an alkoxycarbonyl-substituted alkyl group, or a sulfo-substituted alkyl group having an atom. 1.) A method for dyeing textile materials, characterized by using a reactive dye composition containing one or a mixture of two or more monoazo compounds or metal salts thereof.