KR101359445B1 - The synthesis of yellow azo disperse dyes for micro fiber dyeing - Google Patents

Abstract

The present invention relates to a yellow azo dispersion dye for microfiber dyeing and a synthesis method thereof. More specifically, the present invention relates to a yellow azo dispersion dye for microfiber dyeing suitable for automobile interior materials and a method of synthesizing it.
The yellow azo disperse dye prepared in the present invention has excellent light resistance, sublimation resistance and dispersibility than conventional dyes, and has a molar extinction coefficient of about 1.7 times higher than conventional disperse dyes. The color can be obtained, which is not only environmentally friendly, but also reduces the production cost.

Description

Yellow azo disperse dye for microfiber dyeing and its synthesis method {The synthesis of yellow azo disperse dyes for micro fiber dyeing}

The present invention relates to the synthesis of yellow azo dispersion dyes. More specifically, the yellow azo dispersion dyes are related to the synthesis of yellow azo dispersion dyes suitable for microfiber dyeing for automotive interior materials having improved light resistance, sublimation resistance, and dispersibility as used for microfiber dyeing.

In addition to improving mechanical performance, automobiles require high-quality and high-quality automotive interior materials to meet the emotional needs of users.In addition to improving fuel efficiency and recycling of used materials, various textile products are needed to reduce the weight of vehicles. It is used.

Unlike the global trend, the Korean automobile market is rapidly increasing in size and quality. Therefore, as the textile market for interior materials is increasingly applied to microfiber yarns, the dye market for dyeing materials for automobile interiors is gradually increasing.

Future trends in the development of textile materials for automotive interiors include the use of microfiber fibers that can satisfy various functions, such as light weight materials, which are environmentally friendly, from heavy materials such as polyurethane-coated artificial leather, animal leather, and harmful volatile-generating fibers. Demand is expected to increase gradually.

The microfiber refers to a fiber that shrinks and processes thinner than one-hundredth of the thickness of a human hair with polyester, and as the diameter of the fiber decreases, flexibility, gloss, slippage and specific surface area are expanded, and specific strength is improved. Therefore, when fabricated from a fabric such as woven or nonwoven fabric, the fibers are differentiated in appearance and touch due to the densification of fibers, the refinement of space, and the increase of the number of fibers present on the surface.These characteristics are the improvement of the functions of conventional textile materials. And new functions. Such microfiber is used as a material for high-end products such as artificial suede, artificial leather, and silk shoes.

However, microfibers for automobiles, the main material of automobile interior materials, have been localized, but dyes for dyeing microfibers have more than 80% of the domestic market dominated by domestic dyes (domestic market, 350 tons / 7 billion won / year). For domestic companies, only a small supply is being made.

Korean Patent Publication No. 2009-0118148 manufactures phthalimide-based dispersion dyes for polyester fibers to improve dye adsorption rate, washing fastness, friction fastness and daylight fastness, but the manufacturing steps are complicated and the effect is not sufficient. have.

Therefore, a high quality dye having excellent physical properties such as light resistance, sublimation resistance, build-up and reproducibility is required.

  In particular, since the internal temperature rises due to the heat received by the vehicle, it is difficult to satisfy very harsh use conditions as dyes used for dyeing general clothing, and a dye having excellent durability that can be used in such harsh conditions is required.

Therefore, the present inventors have developed a yellow azo disperse dye that can be used for dyeing microfibers for automobiles and has excellent light resistance, sublimation resistance, and dispersibility, and is intended to provide a dye that can be environmentally friendly and reduce production costs. .

Republic of Korea Patent Publication 2009-0118148 (November 18, 2009)

The present invention has been made to meet the above-described requirements, and an object thereof is to provide a yellow azo dispersion dye for microfiber dyeing and a synthesis method thereof. More specifically, it is an object to provide a yellow azo dispersion dye for microfiber dyeing suitable for automobile interior and its synthesis method.

It is also an object of the present invention to provide a yellow azo disperse dye and its synthesis method superior to conventional dyes in light resistance, sublimation resistance and dispersibility.

The present invention for achieving the above object relates to a yellow azo dispersion dye and a method for producing the same.

The yellow azo dispersion dye of the present invention is represented by the following [Formula 1].

 [Formula 1]

In Formula 1, A is selected from the following compounds,

R ₁ to R ₃ in the compound are the same or different from each other, hydrogen atom, hydroxy group, amide group, nitro group, acetyl group, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ a -C ₆ alkoxy group, C ₆ -C ₁₄ aryl group and is selected from SO ₂ R _7, R ₄ to R ₆ each independently represent a hydrogen atom, an alkyl group of _{C 1 -C 6, C 1 -C} 6 of A haloalkyl group, a C ₁ -C ₆ alkoxy group, a nitro group or a halogen atom, wherein R ₇ is C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylamine group, C ₆ -C ₁₄ aryl An amine group, a C ₁ -C ₆ acetoxyalkyl group.

More specifically, the compound of Formula 1 includes the following Formulas 2 to 4.

(2)

(3)

[Chemical Formula 4]

In addition, the present invention relates to a method for preparing each compound, wherein the preparation method of Chemical Formula 2 is as follows.

a) The aniline derivative of the formula (8) is dispersed in one solution selected from water, acetic acid or a mixed solution of acetic acid and propionic acid, and then stirred, followed by addition of hydrochloric acid, sodium nitrite (NaNO ₂ ) or nitrosulfuric acid (HO ₃ SONO). Diazotizing;

b) preparing a coupler solution by dissolving a phenylindole derivative represented by Chemical Formula 5 in any one solution selected from acetic acid or a mixed solution of acetic acid and pyridonic acid;

c) slowly adding the solution diazotized in step a) to the coupler solution prepared in step b), followed by stirring.

In addition, the preparation method of Formula 3 or Formula 4 is as follows.

a) The aniline derivative of the formula (8) is dispersed in one solution selected from water, acetic acid or a mixed solution of acetic acid and propionic acid, and then stirred, followed by addition of hydrochloric acid, sodium nitrite (NaNO ₂ ) or nitrosulfuric acid (HO ₃ SONO). Diazotizing;

b) preparing a coupler solution by dissolving any derivative selected from a pyridone derivative of Formula 6 and an acetoacetanilide derivative of Formula 7 in an alkaline solution;

c) mixing and stirring the diazotized solution of step a) and the coupler solution of step b); and a method for preparing the yellow azo dispersion dye of Formula 3 or 4.

[Chemical Formula 5]

[Chemical Formula 6]

[Formula 7]

[Formula 8]

(R ₁ to R ₆ are the same as above.)

Hereinafter, each compound and its manufacturing method are demonstrated concretely.

The present invention can be represented by the following formula (1).

 [Formula 1]

R ₁ to R ₃ in the compound are the same or different from each other, hydrogen atom, hydroxy group, amide group, nitro group, acetyl group, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ It is selected from alkoxy groups, aryl groups, and SO ₂ R ₇ of C ₆ -C ₁₄ of -C _6, wherein R ₇ is C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl amine group, C ₆ -C amine group of ₁₄ aryl and is selected from the acetoxy group in the C ₁ -C _6.

The alkyl group refers to a linear or pulverized aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, specifically methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t- Butyl, n -pentyl, i -pentyl, n -hexyl, i -hexyl and the like.

The alkoxy group refers to O-alkyl in a linear or crushed aliphatic hydrocarbon group having 1 to 6 carbon atoms, specifically methoxy, ethoxy, n -propoxy, i -propoxy, n -butoxy , i -butoxy, t -butoxy, n -pentoxy, i -pentoxy, n -hexoxy, i -hexoxy and the like.

The haloalkyl group is a linear or crushed aliphatic hydrocarbon group having 1 to 6 carbon atoms in which at least one halogen is substituted, and includes a chloromethyl, dichloromethyl, trifluoromethyl group, 1,2-dichloroethyl group, and the like. Can be.

Preferably, R ₁ to R ₃ are the same or different from each other, a hydrogen atom, a hydroxyl group, an amide group, a nitro group, an acetyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, SO ₂ NHC ₆ H ₅ , SO ₂ (CH ₂ ) ₂ OCOCH ₃ Etc. may be included.

More specifically, the compound of Formula 1 includes Formula 2 .

(2)

In Formula 2 R ₁ to R ₃ are the same or different, a hydrogen atom, a hydroxyl group, an amide group, a nitro group, a haloalkyl group of the acetyl group, C ₁ -C ₆ alkyl, C ₁ -C ₆ of, C is selected from ₁ -C ₆ alkoxy group, an aryl group, and SO ₂ R ₇ of C ₆ -C ₁₄ of, R ₄ are each independently a hydrogen atom, an alkyl group of C ₁ -C _6, a haloalkyl group of C ₁ -C ₆ , C ₁ -C ₆ alkoxy group, nitro group or halogen atom, R ₇ is C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylamine group, C ₆ -C ₁₄ arylamine group And C ₁ -C ₆ acetoxyalkyl group.

The alkyl group refers to a linear or pulverized aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, specifically methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t- Butyl, n -pentyl, i -pentyl, n -hexyl, i -hexyl and the like.

The alkoxy group refers to O-alkyl in a linear or crushed aliphatic hydrocarbon group having 1 to 6 carbon atoms, specifically methoxy, ethoxy, n -propoxy, i -propoxy, n -butoxy , i -butoxy, t -butoxy, n -pentoxy, i -pentoxy, n -hexoxy, i -hexoxy and the like.

The halogen atom means fluorine, chloro, bromo, iodine atom.

The haloalkyl group is a linear or crushed aliphatic hydrocarbon group having 1 to 6 carbon atoms in which at least one halogen is substituted, and includes a chloromethyl, dichloromethyl, trifluoromethyl group, 1,2-dichloroethyl group, and the like. Can be.

Preferably, R ₁ to R ₃ are the same or different from each other, a hydrogen atom, a hydroxyl group, an amide group, a nitro group, an acetyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, SO ₂ NHC ₆ H ₅ , SO ₂ Represents (CH ₂ ) ₂ OCOCH ₃ , and R ₄ may include a hydrogen atom, a methyl group, an ethyl group, a butyl group, a methoxy group, an ethoxy group, a chlorine atom, and the like.

The yellow azo dispersion dye having the structure of Chemical Formula 2 according to the present invention may be specifically exemplified as the following compound, but the following compound is not intended to limit the present invention.

Scheme 1 shows a reaction scheme of the yellow azo dispersion dye of the formula (2).

[Reaction Scheme 1]

Hereinafter, a method for preparing a yellow azo dispersion dye of Chemical Formula 2 in Scheme 1 will be described in detail.

a) The aniline derivative represented by Chemical Formula 8 in Scheme 1 is dispersed in one solution selected from water, acetic acid or a mixed solution of acetic acid and propionic acid and stirred, followed by hydrochloric acid, sodium nitrite (NaNO ₂ ) or nitrosulfuric acid (HO ₃ SONO). Diazotizing by adding;

b) preparing a coupler solution by dissolving a phenylindole derivative represented by Chemical Formula 5 in Scheme 1 in any one solution selected from acetic acid or a mixed solution of acetic acid and pyrionic acid;

c) slowly adding the solution diazotized in step a) to the coupler solution prepared in step b), followed by stirring. The yellow azo dispersion dye of Formula 2 may be prepared. In addition, after step c), d) washing the solution of step c) with a solvent and dried; To further include a yellow azo dispersion dye of Formula 2 may be prepared in Scheme 1.

When using a mixture of acetic acid and propionic acid in step a) and b) it is preferable to use in the ratio range of 3 to 5: 0.5 to 3, the temperature is 0 to 10 ℃ to maintain the diazo reaction well well Make it happen.

In addition, the temperature in the step b) and c) is also preferably maintained at 0 ~ 10 ℃.

In addition, the compound of Formula 1 includes any one of the yellow azo dispersion dyes selected from the following formula (3) or (4).

 (3)

 [Chemical Formula 4]

Formula 3 with R ₁ to R ₃ eseo 4 are the same or different, and represent a hydrogen atom, a hydroxyl group, an amide group, a nitro group, an acetyl group, a haloalkyl group of C ₁ -C ₆ alkyl, C ₁ -C ₆ of , An alkoxy group of C ₁ -C _6, an aryl group of C ₆ -C ₁₄ and SO ₂ R ₇ , R ₄ to R ₆ are each independently a hydrogen atom, an alkyl group of C ₁ -C ₆ , C _1- It is selected from a C ₆ haloalkyl group, an alkoxy group, a nitro group or a halogen atom, a C ₁ -C _6, wherein R ₇ is C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl amine group, C ₆ -C amine group of ₁₄ aryl and is selected from the acetoxy group in the C ₁ -C _6.

The alkyl group refers to a linear or pulverized aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, specifically methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t- Butyl, n -pentyl, i -pentyl, n -hexyl, i -hexyl and the like.

The alkoxy group refers to O-alkyl in a linear or crushed aliphatic hydrocarbon group having 1 to 6 carbon atoms, specifically methoxy, ethoxy, n -propoxy, i -propoxy, n -butoxy , i -butoxy, t -butoxy, n -pentoxy, i -pentoxy, n -hexoxy, i -hexoxy and the like.

The halogen atom means fluorine, chloro, bromo, iodine atom.

The haloalkyl group is a linear or crushed aliphatic hydrocarbon group having 1 to 6 carbon atoms in which at least one halogen is substituted, and includes a chloromethyl, dichloromethyl, trifluoromethyl group, 1,2-dichloroethyl group, and the like. Can be.

Preferably, R ₁ to R ₃ are the same or different from each other, a hydrogen atom, a hydroxyl group, an amide group, a nitro group, an acetyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, SO ₂ NHC ₆ H ₅ , SO ₂ (CH ₂ ) ₂ OCOCH ₃ , and R ₄ R ₆ may include a hydrogen atom, a methyl group, an ethyl group, a butyl group, a methoxy group, an ethoxy group, a chlorine atom, and the like.

The yellow azo dispersion dye having the structure of Formula 3 or Formula 4 according to the present invention may be specifically exemplified as the following compound, but the following compound is not intended to limit the present invention.

Hereinafter, a method for preparing any one of the yellow azo dispersion dyes selected from Formula 3 or Formula 4 will be described in detail.

Scheme 2 below shows the scheme of Chemical Formula 3, and Scheme 3 below shows the scheme of Formula 4.

[Reaction Scheme 2]

Scheme 3

a) The aniline derivative represented by Chemical Formula 8 in Schemes 2 to 3 is dispersed in one solution selected from water, acetic acid or a mixed solution of acetic acid and propionic acid, and then stirred, followed by hydrochloric acid, sodium nitrite (NaNO ₂ ) or nitrosulfate (HO). Diazotizing by adding ₃ SONO);

b) preparing a coupler solution by dissolving any one derivative selected from a pyridone derivative of Formula 6 and acetoacetanilide derivative of Formula 7 in Scheme 2 in Scheme 2;

c) mixing and stirring the diazotized solution of step a) and the coupler solution of step b); to prepare a yellow azo dispersion dye of Formula 3 or 4. In addition, after step c), d) washing the solution of step c) with a solvent and dried; Further comprising a yellow azo dispersion dye of Formula 3 or Formula 4 may be prepared.

When using a mixture of acetic acid and propionic acid in step a) and b) it is preferable to use in the ratio range of 3 to 5: 0.5 to 3, the temperature is 0 to 10 ℃ to maintain the diazo reaction well well To make it happen.

In addition, in steps b) and c), the temperature is in the range of -20 to 20 ° C, preferably 0 to 10 ° C, and when the coupling reaction is in the range of pH 6 to 8, preferably pH 6 to 7. Make it work well.

In step b), the alkaline solution is a solution in which an alkali metal salt is dissolved in a solvent of water, alcohol or an aqueous alcohol solution. The alcohol may be a lower alcohol such as methanol, ethanol, propanol, butanol, and preferably methanol or ethanol. Alkali metal salts may include hydroxides, carbonates, hydrogen carbonates and the like of alkali metals such as sodium and potassium, and preferably sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate.

The yellow azo dispersed dyes of Chemical Formulas 2 to 4 prepared according to the present invention had a light resistance, a sublimation resistance, and a dispersibility effect equivalent to those of the conventional yellow dispersed dyes, and the molar extinction coefficient was about 1.7 times higher. As a result, the same concentration of color can be obtained by reducing the amount of dye used during dyeing, which is not only environmentally friendly, but also reduces the production cost.

Hereinafter, the present invention will be described by way of example in order to describe the present invention in more detail, but the present invention is not limited to the following examples.

Example 1

6.8 g (0.05 mol) of 4'-aminoacetophenone was dispersed in 100 ml of an acid mixed solution (acetic acid: propionic acid = 4: 1) as a diazo, and stirred for 30 minutes at room temperature, followed by 11 ml (0.127 mol) of concentrated hydrochloric acid. The reaction was cooled to 0 ° C. Then, 18.5 ml (0.055 mol) of 3 N NaNO ₂ was slowly added over 40 minutes, taking care not to let the reaction temperature exceed 5 ° C. After stirring at 0 ° C for 2.5 hours, 0.5 g of sulfamic acid was added to the excess of nitrous acid. Was removed and the diazotization reaction was completed.

10.4 g (0.05 mol) of 1-methyl-2-phenylindole was dispersed in 100 ml of an acid mixed solution (acetic acid: propionic acid = 4: 1), and then the reaction solution was kept at 0 ° C. The mixture was slowly added over 30 minutes while being careful not to exceed 5 ° C.

The reaction was stirred at 0 ° C. for 2 hours and then the reaction was slowly warmed up and stirred at room temperature for 3 hours to complete the coupling reaction. The reaction was poured into 250 ml of iced water, stirred at room temperature for 1 hour, filtered, the resulting product was dispersed in 200 ml of water, stirred at room temperature for 30 minutes, filtered and washed sufficiently with water, and the solid product was dispersed in 200 ml of methanol at room temperature. After stirring for 30 minutes, it was filtered and dried to obtain a yellow solid azo dispersion dye.

[Examples 2 to 9]

It was carried out in the same manner as in Example 1, using aniline derivatives as shown in Table 1 below to obtain a yellow azo dispersion dye.

Table 1 below describes the amount of aniline derivatives used in Examples 1 to 9, aniline derivatives used, coupler derivatives, coupler used, and synthetic yields.

Table 1

[Example 10]

8.3 g (0.027 mol) of 4-amino-2,5-dimethoxy- N -phenylsulfonamide are dispersed in 90 ml of an acid mixed solution (acetic acid: propionic acid = 4: 1) and stirred for 10 minutes at room temperature, followed by concentrated hydrochloric acid. 9 ml (0.10 mol) were added and the reaction cooled to 0 ° C. Then, add 9.5 ml (0.0285 mol) of 3 N NaNO ₂ slowly for 20 minutes, taking care not to let the reaction temperature exceed 0 ° C, stir at 0 ° C for 2 hours, and add 0.3 g of sulfamic acid to remove excess nitrite. It was removed and the diazotization reaction was completed.

4.4 g (0.027 mol) of 1-methyl-4-methyl-3-cyano-6-hydroxy-2-pyridone was dissolved in 90 ml of 0.8 N NaOH, and the reaction solution was prepared at 0 ° C. in a diazo solution prepared above. The mixture was added slowly for 30 minutes while being careful not to exceed, and then stirred at 0 ° C. for 2.5 hours, followed by filtration to separate the solid product. This was dispersed in 300 ml of H ₂ O, stirred at room temperature for 20 minutes, filtered and washed thoroughly with H ₂ O. The solid product was dispersed in 200 ml of methanol, stirred at room temperature for 30 minutes, filtered and dried to give a yellow solid. An azo dispersion dye was obtained.

[Example 11]

It was carried out in the same manner as in Example 10, using aniline derivatives as shown in Table 2 below to obtain a yellow azo dispersion dye.

Table 2 below describes the amount of aniline derivatives, aniline derivatives used, coupler derivatives, coupler used, and synthetic yields used in Examples 10 to 11.

[Table 2]

[Example 12]

4.0 g (0.03 mol) of 4'-aminoacetophenone was dispersed in 60 ml of an acid mixed solution (acetic acid: propionic acid = 4: 1), stirred at room temperature for 10 minutes, and then 6.6 ml (0.076 mol) of concentrated hydrochloric acid was added to the reaction product. Was cooled to 0 ° C. Then, 11.1 ml (0.033 mol) of 3 N NaNO ₂ was slowly added for 20 minutes while taking care that the temperature of the reaction did not exceed 0 ° C., stirred at 0 ° C. for 2 hours, and 0.3 g of sulfamic acid was added to give excess nitrite. It was removed and the diazotization reaction was completed.

8.1 g (0.03 mol) of 4-chloro-2,5-dimethoxy acetoacetanilide was dispersed in 60 ml H ₂ O, and 20 ml of 4 N NaOH was added to completely dissolve the coupler and kept at 5 ° C., which was obtained above. The reaction mixture was slowly added to the diazotized solution while being careful not to raise the temperature of the reactant. After stirring at 5 ° C. for 1 hour, the reaction was gradually heated up and stirred at room temperature for 2 hours, and then the reaction was filtered. The solid product was dispersed in 300 ml of H ₂ O, stirred at room temperature for 30 minutes, and filtered. The product was dispersed in 300 ml of methanol, and then gradually heated up. The mixture was stirred at 50 ° C. for 30 minutes, cooled to room temperature, filtered, and dried to give a yellowish color. A solid azo dispersion dye was obtained.

[Examples 13 to 14]

A yellow azo dispersion dye was obtained in the same manner as in Example 12, using the aniline derivative as shown in Table 3 below.

Table 3 below describes the amount of aniline derivatives used in Examples 12 to 14, aniline derivatives used, and synthetic yields.

[Table 3]

Hereinafter, the physicochemical characteristics of the yellow azo dispersion dyes prepared in the present invention were confirmed by Experimental Examples 1 to 4.

Experimental Example 1 Dyeing Experiment

The milled dye (0.5% owf; On the Weight of Fiber.) Is the bath ratio (the weight ratio of the solvent dissolving the dye and the dyeing aid to 1 Kg of the salt, ie the weight ratio of water) 1:20. Staining was carried out using 1 ml of leveling agent at pH 4.5 (buffer solution).

Stain for 60 minutes at 130 ℃, 0.85 g / L, NaOH 1 g / L, reducing agent (Non-ionic sulphinic acid derivative, Doxalin MSA, M. Dohmen Korea), surfactant (Neutral phosphoric ester, Doavin WEA, M. Dohmen Korea) ) 1 g / L was used for 10 minutes under reduced cleaning and drying.

-Dyeing machine: High temperature / high pressure dyeing machine (Color pet`s 12)

-Test gun: Polyester Knit

Experimental Example 2 Dispersion Experiment

2 g of the dye was dispersed in 200 ml of ion-exchanged water, stirred for about 10 minutes, warmed to 71 ° C, vacuum filtered using Whatman paper # 2 (11 cm) and # 4 (11 cm), and dried naturally. Filtration time was measured.

Experimental Example 3 Day Fastness Test

The color fastness of the specimen and the standard blue dye were exposed to the Xenon arc lamp on a weather-o-meter (Atals) at the same time to compare the degree of change of the specimen to that of the standard blue dye using Computer Color Matching. It was.

Experiment with the following HYUNDAI method.

-Condition: Temperature 89 ℃ Humidity 50%, Chamber 62 ℃

-Illuminance condition: 0.55W / cm ² , 700 KJ (1 hour = 1.98 KJ)

-Rating: Blue Scale 1 ~ 8

Experimental Example 4 Sublimation Experiment

The grade was determined according to Gray Scale (grades 1-5) by experiment of AATCC 117-1999 for 30 seconds at 180 ℃.

Table 4 summarizes the MS ( m / e ), ¹ H NMR, and UV (λ _max and ε values) spectrum data for confirming the structure of each of the yellow azo dispersion dyes prepared in Examples 1 to 14 below. It was.

Table 5 shows the light fastness, dispersion stability and sublimation properties of the prepared yellow azo dispersion dye.

Table 6 shows the maximum absorption wavelength and molar extinction coefficient of the yellow azo dispersion dyes prepared in the present invention.

[Table 4]

_

[Table 5]

[Table 6]

Claims (5)

Yellow azo dispersion dye represented by the following [Formula 1]:
[Chemical Formula 1]

In Formula 1, A is selected from the following compounds,

R ₁ or R ₃ in the compound is the same or different from each other, hydrogen atom, hydroxy group, amide group, nitro group, acetyl group, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ An alkoxy group of -C _6, an aryl group of C ₆ -C ₁₄ and SO ₂ R ₇ are selected from R ₂ is an acetyl group or an acetylamino group; R ₄ to R ₆ are each independently selected from a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a nitro group or a halogen atom, and R ₇ Is selected from a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylamine group, a C ₆ -C ₁₄ arylamine group and a C ₁ -C ₆ acetoxyalkyl group. The method according to claim 1, wherein R ₁ or R ₃ is the same or different from each other, hydrogen atom, hydroxy group, amide group, nitro group, acetyl group, methyl group, ethyl group, methoxy group, ethoxy group, SO ₂ NHC ₆ H ₅ And SO ₂ (CH ₂ ) ₂ OCOCH ₃ , wherein R ₄ to R ₆ represent a hydrogen atom, a methyl group, an ethyl group, a butyl group, a methoxy group, an ethoxy group, and a chlorine atom. The yellow azo disperse dye according to claim 1, wherein the compound of Formula 1 is selected from Formula 9.
[Chemical Formula 9]

a) The aniline derivative of the formula (8) is dispersed in one solution selected from water, acetic acid or a mixed solution of acetic acid and propionic acid, and then stirred, followed by addition of hydrochloric acid, sodium nitrite (NaNO ₂ ) or nitrosulfuric acid (HO ₃ SONO). Diazotizing;
b) dissolving the acetoacetanilide derivative of Formula 7 in an alkaline solution to prepare a coupler solution;
c) mixing and stirring the diazotized solution of step a) and the coupler solution of step b).
[Chemical Formula 4]

(7)

[Chemical Formula 8]

(R ₁ to R ₆ are the same as in Claim 1.) The method of claim 4, further comprising, after step c), d) filtering the solution of step c) with a solvent, washing and drying; Method for producing a yellow azo dispersion dye of Formula 4 further comprising.
[Chemical Formula 4]

(R ₁ to R ₆ are the same as in Claim 1.)