KR20080114434A - Fiber reactive yellow dyes composites and methods for dyeing fiber using the same - Google Patents

Abstract

A reactive yellow dye composition is provided to ensure a build-up property, uniform dyeing, washing durability, chlorine color fastness and light fastness of the dyed product. A reactive yellow dye composition comprises at least one compound having the formula 1 and at least one compound having the formula 4. In the formula 1, D is a group of the formula 2a or 2b having a mother material for yellow; R1 is a substituted or non-substituted C1-4 linear or branched alkyl group, arbitrarily substituted aryl group or hydrogen atom; and X1 and X2 are halogen, hydroxyl, carboxy, cyanine, hydrogen, sulfonic acid or C1-4 alkoxy group.

Description

Reactive yellow dye composition and fiber dyeing method using the same {Fiber Reactive Yellow Dyes Composites and Methods for Dyeing Fiber Using the Same}

Figure 1 is a graph showing the measurement of the build-up of the dye stains through an embodiment of the present invention

The present invention relates to a reactive yellow dye composition and a method for dyeing fibers using the same, and more particularly, to dye a fiber material including hydroxyl groups, particularly cellulose fibers, which is difficult to realize with a single dye. The present invention relates to a reactive yellow dye composition capable of realizing a series of colors, having excellent dyeing properties, various fastnesses, and improving dyeing operations, and a method of dyeing fibers using the same.

Conventional techniques for dyeing yellow to conventional cellulose fiber materials are bifunctional reactive dyes. children. Staining with the following compounds called Reactive Yellow 145 was common.

However, since dyeing with a compound according to the above formula is difficult to realize a deep color and various colors, a mixture of two or more dye compounds may be used. Such a mixed dye may be, for example, a red compound and a blue color. When mixed with the compound, the compatibility between the two dyes is generally not good, the desired color reproducibility is inferior, the build-up (lack of build-up) was not suitable for high concentration dyeing.

Therefore, although a single yellow dye compound may be used, the single yellow dye compound developed so far is not suitable for high concentration dyeing due to low buildup properties during dyeing, and particularly, high fastness to light or sweat is required, but There was a problem that did not satisfy.

On the other hand, dyeing using reactive dyes requires a more economical method in terms of the quality of dyeing and profitability of the dyeing process, and therefore has a high color yield during high-density dyeing operations, There is a need for reactive dyes that are very easy to clean. As a result, there is a very high need for a novel reactive dye having high fastness to light or washing while meeting these conditions.

Therefore, the present invention is to solve the problems of the prior art as described above, and excellent color fastness for light and wet treatment during the dyeing of textile materials, and deep color difficult to realize in a single dye through the compound dyeing using the same The purpose of the present invention is to provide a reactive yellow dye composition capable of reproducing and greatly reducing the amount of inorganic salts used during dyeing and economically performing high-quality dyeing and dyeing method using the same.

In order to achieve the above object, the present invention

It is achieved by providing a reactive yellow dye composition comprising at least one compound having the structure of formula 1 and at least one compound having the structure of formula 4.

In Chemical Formula 1,

D is a group of formula 2a or 2b having a yellow chromosome;

R ₁ is a substituted or unsubstituted linear or branched alkyl group having 1 to 4 carbon atoms, an optionally substituted aryl group, or a hydrogen atom;

X ₁ and X ₂ are each independently halogen, hydroxy, carboxy, cyanine, a hydrogen atom, a sulfonic acid or an alkoxy group having 1 to 4 carbon atoms;

Y is halogen, hydroxyl, 3-carboxypyridin-1-yl, 3-carbamoylpyridin-1-yl, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted amino group Or an N-heterocycle group which may further contain a hetero atom;

Z is a group of formula (3);

n ₁ and n ₂ are each independently 0 to 4;

n ₃ is 0 or 1 and when n ₃ is 0,-(SO ₃ H) n ₃ is a hydrogen atom;

_{However, - (CH 2) n 1} -X 1 and - (CH ₂₎ n ₂ -X ₂ If is different from each other, n ₁ is O and X ₁ is a hydrogen atom; when n ₁ and n ₂ are each 0 and X ₁ is a hydrogen atom, X ₂ is not a hydrogen atom; When n ₁ is 0, n ₂ is 2 and X ₁ is hydrogen, X ₂ is not a carboxy group.

In Chemical Formula 2a,

R ₂ is methyl, -NHCONH ₂ , or -NHCOT, wherein T is methyl, ethyl, -CH ₂ CH ₂ COOH or -CH = CHCOOH;

R ₃ is a hydrogen atom, lower alkyl or lower alkoxy;

U is a vinyl group or a general formula CH ₂ -CH ₂ -Q, where Q is a living group that can be removed under alkaline conditions, and preferred examples of such living groups are chlorine, acetoxy, benzoyloxy, phosphate, sulf Peyto and others.

In Formula 2b, X ₁ , X ₂ , Z, n ₁ , n ₂ , n ₃ are the same as in Formula 1.

In Chemical Formula 3, U is the same as Chemical Formula 2a.

In Chemical Formula 4,

R ₄ and R ₅ independently of one another are hydrogen, sulfo, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, hydroxyl, halogen, amino, phenylamino, acetyl unsubstituted or substituted with C ₁ -C ₄ alkyl Amino, C ₂ -C ₄ alkanoylamino, benzoylamino, or ureido groups;

R ₆ , and R ₇ are each independently hydrogen or C ₁ to C ₄ Alkyl, 2-hydroxyethyl, 2-chloroethyl, 2-fluoroethyl group;

X ₃ independently of one another is halogen, hydroxy, amino, mono or di C ₁ to C ₄ alkyl amino, phenylamino unsubstituted or substituted C ₁ to C ₄ alkyl, a pyri unsubstituted or carbamoyl or carboxyl substituted Denyl, morpholino;

D ₂ is a substituent of the following Chemical Formula 5a or 5b.

R ₁₀ Is hydrogen, sulfo, C ₁ ~ C ₄ Alkyl, C ₁ to C ₄ Alkoxy, halogen, 2-hydroxyethyl, 2-chloroethyl, or 2-fluoroethyl group;

R ₁₁ is hydrogen or a C ₁ -C ₄ alkyl group.

Q ₂ and Q ₃ independently of each other are a radical of the formula -SO ₂ -Z or a formula -CONH- (CH ₂ ) _r -SO ₂ -Z, wherein Z is a vinyl or a formula -CH ₂ -CH ₂ -Y radical , Y is a leaving group (e.g., -Cl, -Br, -F, -OSO 3 H, -SSO 3 H, -OCO-CH 3, -OPO 3 H 2, -OCO-C 6 H 5, - OSO _{2 -} C ₁ to C ₄ Alkyl, or -OSO ₂ -N (C ₁ -C ₄ alkyl) _2, etc.), and r is an integer of 1 to 6;

In this case, the compound defined by Chemical Formula 1 is more preferably, n ₁ is 0, n ₂ is 2, X ₁ is a hydrogen atom, X ₂ is a hydroxy group is used.

In addition, in Y, preferred examples of halogen include fluorine and chlorine, and preferred examples of N-heterocyclo include morpholine, thiomorpholine, piperazine or piperidine radical, and the amino Preferred examples of the group are alkylamino, and examples of the alkylamino include N-mono- (C ₁ -C ₄ ) straight or branched alkylamino unsubstituted or substituted with hydroxyl, sulfato or sulfur. N, N-di- (C ₁ -C ₄ ) straight or branched alkylamino, and more preferably a group of the formula (6) is used.

In Chemical Formula 6, R ₁ is the same as in Chemical Formula 1, and U is the same as in Chemical Formula 2a.

In addition, in the compound defined by Chemical Formula 2a, most preferably U is a vinyl group or β-sulfatoethyl.

Along with this, the compound defined by Chemical Formula 4 is more preferably hydrogen is used for R ₆ and R ₇ .

In addition, X ₃ is most preferably used fluorine or chlorine.

The compounding ratio of the compound having the structure of Formula 1 and the compound having the structure of Formula 4 may be determined by various factors such as the kind of these compounds, the type of color to be implemented, and preferably, 100 wt% of the dye composition. 5 to 95% by weight of the compound of Formula 1 and 5 to 95% by weight of the compound of Formula 4 are mixed. In the above compounding ratio, if the compound defined by Formula 1 is too small, there is a problem in oxidative bleaching fastness and relative dyeing strength, and on the contrary, when the compound defined by Formula 4 is relatively small, daylight fastness This is because there is a problem of water fastness.

Compounds represented by the plurality of formulas can be prepared based on the formula structure, if one of ordinary skill in the art. For example, diazotization reaction, coupling reaction, condensation reaction, etc. may be performed to prepare the compounds represented by the above chemical formulas. Such reactions are well known to those skilled in the art. It can be easily reproduced.

As described above, the reactive yellow dye composition according to the present invention has a high reproducibility and excellent fixing ability when dyeing on fibers compared to conventional heterodifunctional compounds and vinyl sulfone compounds, and at the same time, dyes that are not fixed to the fibers are easily washed. It may be, and has properties such as excellent oxidation bleaching and fastness to moisture.

In addition, the present invention provides a method for dyeing the aforementioned reactive yellow dye composition to a hydroxy and / or carboxyl amino-containing fibrous material, more preferably a cellulose fiber material or a blended fiber material thereof.

The reactive yellow dye compositions according to the invention are suitable as dyes for dyeing all types of cellulose fiber materials, and such cellulose fiber materials include, for example, natural cellulose fibers such as cotton, flax, hemp and the like. , Pulp and recycled cellulose, and the like, and are particularly suitable for dyeing cotton. The dye mixtures of the invention are also suitable for dyeing cellulose blend fabrics such as cotton / polyester, cotton / nylon blend fabrics and the like.

In the dye solution to be used for the above purpose, the amount of the reactive red dye composition of the present invention may vary depending on the desired degree of coloring, for example, 0.01 to 10% by weight, preferably based on the fabric to be dyed. 0.01 to 6% by weight can be used.

Yellow dyes can be obtained by applying the dye mixtures according to the invention to cellulose fibers according to conventional dyeing or printing methods.

In the dyeing dyeing method, neutral salts such as sodium sulfate and sodium chloride may be used as a stimulating agent to assist the dye adsorption, and alkali agents such as sodium carbonate and sodium hydroxide may be used as the acid binder to help the cellulose fiber and the dye to be bonded.

In the printing dyeing method, a dye is used to attach a dye. Examples of the dye include sodium alginate, starch, polyvinyl alcohol (PVA), and carboxymethyl cellulose (CMC). A sodium bicarbonate, sodium carbonate, or the like is used as a fixing agent to be fixed by cure, and urea may be used to enhance dissolution and leveling of the dye.

In addition, the dye mixtures according to the invention are particularly suitable for dyeing by an extraction method. Dyeing by the adsorption method is generally, in an aqueous medium, the weight ratio of water to dye is 1: 2 to 1: 60, preferably 1: 5 to 1: 20, the reaction is 20 to 105 ℃, preferably 30 to 90 It is performed at the temperature of 40 degreeC, More preferably, 40-80 degreeC.

Another suitable dyeing method is a pad dyeing method, in which the fabric is generally impregnated with an aqueous solution, saline solution, saline solution or the like, and the pick-up is based on the weight of the fiber material to be dyed. 20 to 150%, preferably 40 to 120%, more preferably 50 to 100% is suitable. The aqueous solution already contains a fixed alkali, or in some cases the fiber material is treated with a fixed alkali after impregnation. Examples of suitable alkali metals are mixtures of sodium carbonate, sodium bicarbonate, sodium hydroxide, disodium phosphate, trisodium phosphate, sodium borate, aqueous ammonia, sodium trichloroacetate or sodium silicate solution, among which alkali hydroxides and / or alkali carbonates In particular, sodium hydroxide and / or sodium carbonate are preferred.

Fixation can be carried out through the thermal treatment of the impregnated fibrous material, for example at a temperature of 100 to 120 ° C., in particular saturated steam. According to the so-called cold pad-batch method, the dye is placed in a padder with alkali and stored at room temperature for several hours, for example 3 to 40 hours, and fixed. After fixation, dispersants are added to the dyeings as necessary and washed with precision.

The dyeings obtained according to the present invention are bright and high in clarity, and have excellent build-up and leveling properties. In addition, the adherence is high, and non-fixed dyes can be easily washed off, and there is little difference between the degree of adsorption and the adherence, i.e., the loss of soap. Moreover, the obtained dyeings have excellent coloration, high fiber-dye binding stability, good fastness to washing, seawater, cross-dyeing and sweating, fastness to wrinkles, ironing and friction, and the like. The light fastness is also excellent.

Hereinafter, the present invention will be described in more detail with reference to the following examples, which are only presented to aid the understanding of the present invention, but the present invention is not limited thereto. In the following examples, parts and percentages are by weight and parts by weight are in kg to l (liter) unless otherwise noted.

<Manufacture example 1>

Diazo-reaction of 4-aminobenzene-1,3-disulfonic acid, followed by coupling reaction with 3-ureidoaminoaniline to prepare a monoazo compound, 4.1 g of monoazo-water prepared as described above It was dissolved in 100 g of aqueous solution and 1.8 g of chlorocyanuls were added to condense for 3 hours at 5 ° C and pH 5. After completion of the reaction, 20 g of an aqueous solution in which 2.2 g of 1-amino-3- (2-hydroxyethyl) aminobenzene-4-sulfonic acid was dissolved was further added, followed by condensation reaction at 30 ° C. and pH 5 for 3 hours. A diazo solution of 2.8 g of 4-sulfatoethylsulfone-1-aminobenzene was added to the solution, and a coupling reaction was performed at 10 ° C. and pH 5.5 for 3 hours. The reaction solution was filtered to remove insoluble matters. After drying, to prepare a compound of formula (7). In Formula 7, D, A, B, and R ₁ are shown in Table 1 below.

<Production Examples 2 to 10>

Based on Preparation Example 1, it was possible to synthesize the compounds described in Table 1 below, and their specific preparation method can be sufficiently expected through the preparation examples based on the chemical structure of the product, Description is omitted.

No. D (Diazo component) A B R1 Preparation Example 1 K-acid -NH ₂ CONH ₂ -H -NH ₂ Preparation Example 2 K-acid -NH ₂ CONH ₂ -H NHCH ₂ CO ₂ H Preparation Example 3 K-acid -NH ₂ CONH ₂ -H -NHCH ₂ CH ₂ OH Preparation Example 4 C-acid NH ₂ COCH ₃ -H NHCH ₂ CO ₂ H Preparation Example 5 C-acid NH ₂ COCH ₃ -H -NHCH ₂ CH ₂ OH Preparation Example 6 Aniline-2,4 -NH ₂ CONH ₂ -H -NH ₂ Preparation Example 7 Aniline-2,4 -NH ₂ CONH ₂ -H NHCH ₂ CO ₂ H Preparation Example 8 Aniline-2,4 -NH ₂ CONH ₂ -H -NHCH ₂ CH ₂ OH Preparation Example 9 K-acid NH ₂ COCH ₃ -OCH ₃ -NH ₂ Preparation Example 10 K-acid NH ₂ COCH ₃ -OCH ₃ -NHCH ₂ CH ₂ OH

Production Example 11

153 parts of 1-amino-3-ureidobenzene was dispersed in 1500 g of water, neutralized and dissolved in pH 7 with a 25% aqueous sodium hydroxide solution, and then 2000 g of 383 g of 2-amino-3,6,8-naphthyltrisulfonic acid was dissolved in water. After dispersing 100 g of hydrochloric acid and maintaining it at 5 ° C. or less, 230 g of 30% sodium nitrite was added dropwise for 30 minutes to maintain a diazonium salt for 2 hours. The synthesized diazonium salt was added dropwise to the 1-amino-3-ureidobenzene dispersion while maintaining it at 10 or less, and neutralized with a 20% aqueous solution of pH 6.5 sodium carbonate to synthesize a primary coupling body.

184.4 g of cyanuric chloride is dispersed in 300 parts of water at 0 ° C., primary coupling is added, and neutralization is performed with a 20% aqueous solution of sodium carbonate at pH 6.0 to prepare a primary condensate.

281.3 parts of 3-aminobenzene-sulfatoethylsulfonic acid was added to the powder, and neutralized with a 20% aqueous solution of sodium carbonate to pH 6 to prepare a compound of Formula 8.

<Example 1>

One or more compounds prepared in Preparation Examples 1 to 10 and the compound prepared in Preparation Example 11 were dyed on cellulose fibers according to the following dyeing method. It was dyed with and showed high light fastness and washing fastness. The color indicated by the dyeing is shown in Table 2 below.

(1) dyeing method 1

1.0 g of the compound of Preparation Example 1 and 1.0 g of the compound of Preparation Example 11 were mixed and dissolved in 400 g of water. This solution was added to 1,500 g of a solution containing 53 g / L sodium chloride to prepare a salt bath. 100 g of cotton fabric was added to the dye bath at 40 ° C., and after 45 minutes, 100 g of a solution containing 16 g / L sodium hydroxide and 20 g calcined sodium carbonate was added. In addition, the temperature of the salt bath was maintained at 40 ° C. for 45 minutes. The dyed fabric was then washed, soaped for 25 minutes upon boiling with a nonionic detergent, washed again and dried.

(2) dyeing method 2

1.0 g of the compound of Preparation Example 2 and 1.0 g of the compound of Preparation Example 11 were mixed and dissolved in 400 g of water. To this solution was added to 1,500 g of a solution containing 53 g / L of sodium chloride to prepare a salt bath. 100 g of cotton fabric was added to the dye bath at 35 ° C., and after 20 minutes, 100 g of a solution containing 16 g of sodium hydroxide and 20 g of calcined sodium carbonate was added. In addition, the temperature of the salt bath was maintained at 35 ° C. for 15 minutes. The temperature was then raised to 60 ° C. over 20 minutes and held at that temperature for another 35 minutes. The dyed fabric was washed, soaped for 25 minutes on boiling using a nonionic detergent, washed again and dried.

(3) printing method

A stock thickener comprising 50 g of sodium alginate, 27.8 g of water, 20 g of urea, and 1.2 g of sodium m-nitrobenzenesulfonate while mixing 5.0 g of the compound of Preparation Example 2 and 5.0 g of the Preparation Example 11 while vigorously stirring. (stock thickening) interspersed in 100g. The cotton fabric was printed and dried with the printing paste obtained above. The printed cotton fabric was steamed at 102 DEG C for 2 minutes in saturated steam, then washed, optionally soaped at boiling, and washed once again to dry.

No. Preparation Example A Preparation Example B Preparation Example A Preparation Example B color Mixture1 Preparation Example 3 Preparation Example 11 10: 90 yellow Mixture 2 Preparation Example 3 Preparation Example 11 20: 80 yellow Mixture 3 Preparation Example 3 Preparation Example 11 30: 70 yellow Mixture 4 Preparation Example 3 Preparation Example 11 40: 60 yellow Mixture 5 Preparation Example 3 Preparation Example 11 50: 50 yellow Mixture 6 Preparation Example 3 Preparation Example 11 60: 40 yellow Mixture 7 Preparation Example 3 Preparation Example 11 70: 30 Orange Mixture8 Preparation Example 3 Preparation Example 11 80: 20 Orange Mixture 9 Preparation Example 3 Preparation Example 11 90: 10 Orange Mixture10 Preparation Example 4 Preparation Example 11 10: 90 yellow Mixture 11 Preparation Example 4 Preparation Example 11 20: 80 yellow Mixture12 Preparation Example 4 Preparation Example 11 30: 70 yellow Mixture13 Preparation Example 4 Preparation Example 11 40: 60 yellow Mixture14 Preparation Example 4 Preparation Example 11 50: 50 yellow Mixture15 Preparation Example 4 Preparation Example 11 60: 40 yellow Mixtures16 Preparation Example 4 Preparation Example 11 70: 30 Orange Mixture17 Preparation Example 4 Preparation Example 11 80: 20 Orange Mixtures18 Preparation Example 4 Preparation Example 11 90: 10 Orange Mixtures19 Preparation Example 5 Preparation Example 11 10: 90 yellow Mixture20 Preparation Example 5 Preparation Example 11 20: 80 yellow Mixture21 Preparation Example 5 Preparation Example 11 30: 70 yellow Mixture22 Preparation Example 5 Preparation Example 11 40: 60 yellow Mixture23 Preparation Example 5 Preparation Example 11 50: 50 yellow Mixture24 Preparation Example 5 Preparation Example 11 60: 40 yellow Mixture25 Preparation Example 5 Preparation Example 11 70: 30 Orange Mixture26 Preparation Example 5 Preparation Example 11 80: 20 Orange Mixture27 Preparation Example 5 Preparation Example 11 90: 10 Orange Mixture28 Preparation Example 5 Preparation Example 11 10: 90 yellow Mixture29 Preparation Example 5 Preparation Example 11 20: 80 yellow Mixture30 Preparation Example 5 Preparation Example 11 30: 70 yellow Mixture31 Preparation Example 5 Preparation Example 11 40: 60 yellow Mixture32 Preparation Example 5 Preparation Example 11 50: 50 yellow Mixtures33 Preparation Example 5 Preparation Example 11 60: 40 yellow Mixture34 Preparation Example 5 Preparation Example 11 70: 30 Orange Mixture35 Preparation Example 5 Preparation Example 11 80: 20 Orange Mixture36 Preparation Example 5 Preparation Example 11 90: 10 Orange Mixture37 Preparation Example 6 Preparation Example 11 10: 90 yellow Mixture38 Preparation Example 6 Preparation Example 11 20: 80 yellow Mixture39 Preparation Example 6 Preparation Example 11 30: 70 yellow Mixture40 Preparation Example 6 Preparation Example 11 40: 60 yellow Mixture41 Preparation Example 6 Preparation Example 11 50: 50 yellow Mixture42 Preparation Example 6 Preparation Example 11 60: 40 yellow Mixture43 Preparation Example 6 Preparation Example 11 70: 30 Orange Mixtures44 Preparation Example 6 Preparation Example 11 80: 20 Orange Mixture45 Preparation Example 6 Preparation Example 11 90: 10 Orange

<Example 2>

Using the dye mixtures 4, 13 and 22 of Table 2 corresponding to the present invention, and a single dye (CI Reactive Yellow 145) used in the prior art, the following dyeing experiments were carried out to check the difference in physical properties during dyeing. It was done.

(1) K / S value per dyeing concentration

Absolute color values are determined using a color measurement instrument called Computer Color Matching (CCM), and the dyeing power and the direction of the color are determined according to the absorption of light from the instrument. At this time, the difference in dyeing power can be confirmed by comparing the K / S value, which is a numerical expression representing the change caused by absorption (absorption coefficient, K) and reflection (scattering coefficient, S) of the light source.

(2) Experiment contents

A salt solution prepared by adding 0.6 g of a dye (or dye mixture) to 1,200 ml of water is placed in a 2 L stainless beaker, and stirred with addition of 1/3 Common Salt, 1/4 Soda Ash, and 1 g / L leveling agent, The cloth wetted with water (Cotton Knit) was squeezed tightly. The fabric was not exposed out of the salt solution during the experiment. After 15 minutes from the time of initial dyeing, 1/3 Common Salt was added and after 15 minutes, 3/4 Soda Ash was added, followed by dyeing for 45 to 60 minutes while maintaining the temperature at 98-100 ° C. After the dyeing was completed, cold rinse, 0.5g / ℓ softener and 1.0g / ℓ Soda Ash was added and soaped (soaping) for 10 minutes at 40-45 ℃. Cold water again, dehydrated and dried at 60 ℃. K / S value was measured for the obtained dye by using CCM.

(3) experimental results

As shown in Figure 1, the dye mixture according to the present invention is C.I. It was found that the K / S value was higher than that of Reactive Yellow 145, which means that the dye mixture of the present invention has excellent buildup properties.

As described above, the reactive red dye composition of the present invention and the method of dyeing the fiber using the same have excellent build-up property, uniformity and washability when dyeing the fiber material, especially cellulose fiber, and the light fastness of the dye. It has excellent fastness, such as washing fastness, chlorine fastness and sweat fastness, and it has excellent dyeing ability even when using less amount of inorganic salt to be applied during dyeing and excellent reproducibility when dyeing and printing dyeing. Excellent buildup in the dyeing field means good dyeing property and excellent property of maintaining color development for a long time. In addition, as described above, the dye mixture of the present invention has a small amount of inorganic salts, which leads to a reduction in wastewater treatment costs and is environmentally friendly.

In addition, one of ordinary skill in the art to which the present invention pertains will be able to make various applications and modifications within the scope of the present invention based on the above contents.

Claims (12)

A reactive yellow dye composition comprising at least one compound having a structure of Preparation Example 1 and at least one compound having a structure of Preparation Example 4. <Manufacture example 1>

In Preparation Example 1, D is a group of Preparation Example 2a or 2b having a yellow chromosome; R ₁ is a substituted or unsubstituted linear or branched alkyl group having 1 to 4 carbon atoms, an optionally substituted aryl group, or a hydrogen atom; X ₁ and X ₂ are each independently halogen, hydroxy, carboxy, cyanine, a hydrogen atom, a sulfonic acid or an alkoxy group having 1 to 4 carbon atoms; Y is halogen, hydroxyl, 3-carboxypyridin-1-yl, 3-carbamoylpyridin-1-yl, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted amino group Or an N-heterocycle group which may further contain a hetero atom; Z is a group of Preparation Example 3 below; n ₁ and n ₂ are each independently 0 to 4; n ₃ is 0 or 1 and when n ₃ is 0,-(SO ₃ H) n ₃ is a hydrogen atom; Provided that when-(CH ₂ ) n _1- X ₁ and-(CH ₂ ) n _2- X ₂ are different from each other, n ₁ is O and X ₁ is a hydrogen atom; when n ₁ and n ₂ are each 0 and X ₁ is a hydrogen atom, X ₂ is not a hydrogen atom; When n ₁ is 0, n ₂ is 2 and X ₁ is hydrogen, X ₂ is not a carboxy group. <Production Example 2a>

In Preparation Example 2a, R ₂ is methyl, -NHCONH ₂ , or -NHCOT, wherein T is methyl, ethyl, -CH ₂ CH ₂ COOH or -CH = CHCOOH; R ₃ is a hydrogen atom, lower alkyl or lower alkoxy; U is a vinyl group or a general formula CH ₂ -CH ₂ -Q, where Q is a living group that can be removed under alkaline conditions, and preferred examples of such living groups are chlorine, acetoxy, benzoyloxy, phosphate, sulf Peyto and others. <Production Example 2b>

In Preparation Example 2b, X ₁ , X ₂ , Z, n ₁ , n ₂ , n ₃ are the same as in Preparation Example 1. <Manufacture example 3>

In Preparation Example 3, U is the same as Preparation Example 2a. <Manufacture example 4>

In Preparation Example 4, R ₄ and R ₅ independently of one another are hydrogen, sulfo, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, hydroxyl, halogen, amino, phenylamino, acetyl unsubstituted or substituted with C ₁ -C ₄ alkyl Amino, C ₂ -C ₄ alkanoylamino, benzoylamino, or ureido groups; R ₆ , and R ₇ are independently of each other hydrogen or a C ₁ -C ₄ alkyl, 2-hydroxyethyl, 2-chloroethyl, 2-fluoroethyl group; X ₃ independently of one another is halogen, hydroxy, amino, mono or di C ₁ -C ₄ alkyl amino, phenylamino unsubstituted or substituted C ₁ -C ₄ alkyl, a pyri unsubstituted or substituted with carbamoyl or carboxyl group Denyl, morpholino; D ₂ is a substituent of Preparation Example 5a or 5b. <Production Example 5a>

<Production Example 5b>

R ₁₀ is hydrogen, sulfo, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogen, 2-hydroxyethyl, 2-chloroethyl, or 2-fluoroethyl group; R ₁₁ is hydrogen or a C ₁ -C ₄ alkyl group. Q ₂ and Q ₃ independently of each other are radicals of Preparation -SO _2- Z or Preparation -CONH- (CH ₂ ) _r- SO _2- Z, wherein Z is vinyl or Preparation -CH _2- CH _2- Y is the radical, Y is a leaving group (e.g., -Cl, -Br, -F, -OSO 3 H, -SSO 3 H, -OCO-CH 3, -OPO 3 H 2, -OCO-C 6 H ₅ , -OSO _2- C ₁ -C ₄ alkyl, or -OSO _2- N (C ₁ -C ₄ alkyl) _2, etc.), and r is an integer of 1-6. The reactive yellow dye composition according to claim 1, wherein n ₁ is 0, n ₂ is 2, X ₁ is a hydrogen atom, and X ₂ is a hydroxy group. The reactive yellow dye composition according to claim 1 or 2, wherein U is a vinyl group or β-sulfatoethyl. The method according to claim 3, wherein Y is a preferred example of halogen include fluorine and chlorine, and a preferred example of the N-heterocyclo include morpholine, thiomorpholine, piperazine or piperidine radicals, the amino group Preferred examples are alkylamino, and examples of the alkylamino are N-mono- (C ₁ -C ₄ ) straight or branched alkylamino or N unsubstituted or substituted with hydroxyl, sulfato or sulfur. , N-di- (C ₁ -C ₄ ) linear or branched alkylamino. The reactive yellow dye composition of claim 4, wherein Y is more preferably a group of Preparation Example 6. <Manufacture example 6>

In Preparation Example 6, R ₁ is the same as in Preparation Example 1, and U is the same as in Preparation Example 2a. The reactive yellow dye composition of claim 1, wherein R ₆ and R ₇ are hydrogen. The reactive yellow dye composition of claim 6, wherein X ₃ is fluorine or chlorine. The reactive yellow dye composition according to claim 1, comprising 10 to 90% by weight of the compound defined in Preparation Example 1 and 10 to 90% by weight of the compound defined in Preparation Example 3. A dyeing method comprising dyeing a fiber material containing nitrogen or a hydroxyl group with a dye solution containing the reactive yellow dye composition of claim 1. The dyeing method according to claim 9, wherein the dyeing is performed by an absorption method, a pad dyeing method, a dip dyeing method, or a printing method. The dyeing method according to claim 9, wherein the reactive yellow dye composition is added in an amount of 0.01 to 10% by weight based on the fabric to be dyed. The dyeing method according to claim 11, wherein the reactive yellow dye composition is more preferably added with 0.01 to 6% by weight based on the fabric to be dyed.

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