KR830000150B1 - Monoazo dyes for dyeing hydrophobic fibers or yarns - Google Patents

Abstract

2,4,6-Z(O2N) (NC)C6H2NH2 (Z = Cl, CN) were diazotized and coupled with 3-R1CONHC6H4NR2R3 (R1 = Me, Et; R2,R3 = C5-8 alkyl to give fast disperse dyes of general structure I, which were stable in hot dyebaths and either alone or in mixture with anthraquinone disperse dyes, gave brilliant, reproducible blue shades on polyester fiber or yarn. I[Z = Cl, R1 = Me, R2 = R3 = (CH2)4Me (II) in a certain cryst. form was esp. stable in dyebaths. Thus, coupling diazodized 2,4,6-Cl(O2N)(NC)C6H2NH2 with 3-AcNHC6H4N[(CH2)4Me 2, suspending the resultant moist filter cake in H2O, and heating 3 hr 95≰C gave II.

Description

Method for preparing monoazo compound

1 and 2 are diagrams showing the X-ray powder diffraction of the monoazo compound before coupling and before heat treatment and the special crystalline monoazo compound formed after heat treatment according to the present invention.

3 is a chart showing the decomposition-exhaust rate characteristics of each dye.

The present invention relates to a process for the preparation of monoazo compounds, and more particularly to a process for producing monoazo dispersion dyes useful for dyeing hydrophobic fibers, in particular polyester fibers and cellulose ester fibers.

In order to dye hydrophobic fibers such as polyester fibers and cellulose ester fibers, anthraquinone disperse dyes are mainly used. The anthraquinone disperse dyes have a low molar absorption coefficient and have a low salt stability. Although it has been used in most cases because of the excellent degradation resistance (ie low pH sensitivity) and the high resolution and fastness of dyeing products, the high price is an important problem. have.

On the other hand, azo dispersants have the advantages of low cost, high molar absorption coefficient, and fastness of dyed products compared to anthraquinone disperse dyes, but have the disadvantage of poor stability in salt bath and gloss of products.

Various azolates have been disclosed. For example, Japanese Patent Application Publication Nos. 1966-6910 (A) and 1976-16554 (B) and British Patent No. 1,489,016 (C) have been disclosed.

※ This compound is not precisely disclosed in Japanese Patent Publication No. 1644/1976, but falls within the scope of the compound.

In addition, the following azo blue disperse dyes are known.

Known Compound

The above-mentioned disperse dyes all have drawbacks as the above-described azo dispersants.

The present inventors have extensively researched to solve these problems, and have developed azophosphate having a high commercial value.

It is an object of the present invention to provide a novel azoblue dispersion having excellent dyeing affinity, stability in salt baths (low pH sensitivity and excellent degradation resistance), sublimation resistance and fastness as well as dark and bright colors.

The present invention comprises a method for producing a novel azo blue dispersion of general formula (I) by reacting a diazo compound of general formula (II) with a compound of general formula (III).

(Wherein R ¹ is a methyl or ethyl group, R ² and R ³ are each an alkyl group of C ₅ to C ₈ and Z is a chlorine or cyano group.)

In particular, the present invention provides a large relative luminance of 11.2 °, 12.6 °, 16.0 °, 17.6 °, 19.2 ° with X-ray powder diffraction (2θ: Cu-Kα) 14.0 °, 18.5 °, 21.4 ° and 25.6 ° at each angle. 2-cyano-4-nitro-6-chloro-2'-acetylamino-4 '-(N, N-di-n-pentyl) in crystalline form showing intermediate relative luminances of 23.5 °, 24.2 and 26.4 ° It is advantageously used for the preparation of amino-1,1'-azobenzene, the preparation method of which is diazotized 2-cyano-4-nitro-6-chloroaniline-3-acetylamino-N, N-di-n The monoazo compound is reacted with pentyl aniline and the resulting monoazo compound is heated in the presence of a surfactant in an aqueous solvent or an organic solvent, if necessary, to produce 2-cyano-4-nitro-6-chloro-2'-acetyl, a monoazo compound. It is advantageous to the process for preparing amino-4 '-(N, N-di-n-pentyl) amino-1,1'-azobenzene.

The alkyl group represented by R ² and R ³ in the general formula (I) represents a C ₅ internal group C ₈ straight alkyl group, but a C ₅ or C ₆ straight alkyl group is suitable.

Suitable as compounds of formula (I) are dyes in which both R ² and R ³ are n-pentyl or n-hexyl (particularly n-pentyl) and Z is chlorine. Among them, most suitable are compounds of the following general formula.

In formula, R <^1> has the meaning mentioned above but especially a methyl group.

Examples of the compound of formula (II) used to prepare the compound of formula (I) include the following.

Compounds of the general formula (III) include the following compounds.

These compounds (III) are alkyl halides or p-toluenesulfonic acids corresponding to 3-acetylaminoaniline or 3-propionylaminoaniline by a known method, for example, as described in Japanese Patent Publication No. 1966-3712. It is prepared by dialkylation with an alkyl ester of.

The dye preparation method of general formula (I) is as follows.

The compound of formula (II) (diazo component) is dissolved in an inorganic acid (e.g. sulfuric acid, hydrochloric acid) or an organic acid (e.g. acetic acid, propionic acid), and nitrosulfic acid is used for 5 hours at low temperature, especially 10-15 占 폚. Diazotize.

Separately, the compound (coupling component) of formula (III) is dissolved in an inorganic acid (e.g. hydrochloric acid, sulfuric acid), an organic acid (e.g. acetic acid, propionic acid) or an organic solvent (e.g. methanol, ethanol) The diazo component of (III) was injected into the solution of the general formula (III) at a temperature of about 10 ° C. or lower and the resulting mixture was reacted for 5 to 10 hours to complete the coupling, and then the precipitated product was filtered and washed with water. And dry.

The dye of formula (I) thus prepared can be used for dyeing hydrophobic fibers in the form of a paste or powder after spray drying by pulverizing with an appropriate dispersant in an aqueous solvent according to methods known in the art.

2-cyano-4-nitro-6-chloro-2'-acetylamino-4 '-(N, N-di-n-pentyl) amino-1,1'-azobenzene (hereinafter referred to as the monoazo compound) Abbreviated) in the preparation of the corresponding diazo component (2-cyano-4-nitro-6-chloroaniline) and coupling component (3-acetylamino-N, N-di-n-pentyl) according to the above-described method. A wet or dry cake of a monoazo compound prepared from aniline) is prepared by heat treatment in the presence of an emulsifier (for example, a dispersant) in an aqueous solvent or an organic solvent (for example, alcohol or acetic acid) as necessary.

The aqueous solvent or organic solvent used in the heat treatment uses a large amount so as to completely immerse the monoazo compound. Generally, it is preferable to use at least 10 times the amount of the monoazo compound in order to stir to uniform heating. good.

For heat treatment, dispersants (e.g., naphthalene sulfonic acid / formalin condensate, naphthalenesulfonic acid / cresol / formalin condensate) or anionic or nonionic surfactants in the range of 1 to 400% by weight of the monoazo compound By making it exist in, it is possible to obtain a desired effect such as improving the dispersibility of the dye.

The heat treatment temperature is appropriate in the range of 80 to 100 ℃ under atmospheric pressure. If the temperature is below 80 ℃, the required effect cannot be obtained and heat treatment must be performed for a long time to obtain the required effect. On the other hand, it can be heat treated at a temperature of 100 ℃ or more, but it does not need to be heat treated at a temperature higher than the pressure cooker.

The heat treatment time depends on the treatment temperature, the amount of aqueous medium or organic solvent, and the type and amount of other additives, but generally 1 to 5 hours is sufficient.

The monoazo compound having a specific X-ray powder refractive index thus prepared is ground in an aqueous medium with a suitable dispersing agent (e.g., naphthalene sulfonic acid-formalin condensate) according to a conventional method known in the art, It is used for dyeing the hydrophobic fibers described above in the form of a powder prepared by spray drying.

The compounds of the present invention are suitable for dyeing hydrophobic fibers, in particular polyester fibers and cellulose ester fibers, in light blue according to methods known in the art. For example, the hydrophobic fibers are immersed in an aqueous medium containing the compound of the present invention and pressurized to be dyed by treatment at a temperature of 105 ° C. or higher, particularly 110 ° C. to 140 ° C.

In the presence of a carrier such as 0-phenylphenol or trichlorobenzene, the fibers are dyed even at the boiling point of water, which is a relatively low temperature.

Furthermore, the so-called thermosol method may also be used. In this case, the hydrophobic fiber cloth is padded with a dye dispersion and dried and heat-treated at 150 ° C to 250 ° C for 30 seconds to 60 seconds.

In addition, the compound of the present invention can be effectively used in the printing method of printing, steaming or thermosolating the forge with a dye paste prepared with a dye dispersion medium and a foil, as well as an organic solvent (eg trichloroethylene, fur as a dyeing medium). It can also be used for the solvent dyeing method using chloroethylene).

As described above, the azo dispersant (I) according to the present invention can infiltrate or print hydrophobic fibers with dark blue and light blue having sufficient dyeing affinity, pH sensitivity (decomposition resistance), sublimation resistance and excellent fastness as well as excellent reproducibility. have.

In particular, the use of a monocrystalline crystalline monoazo compound eliminates the problems of dyeing techniques such as deterioration of dispersibility and formation of condensate, resulting in a uniformly dyed product.

Hereinafter, the part and% of an Example are described by weight as described in the Example of this invention.

1 and 3 are diagrams showing the X-ray powder diffraction of the monoazo compound before the heat treatment after coupling and the special crystalline monoazo compound after the heat treatment, respectively. 1 and 2 are recorded by an automatic recording apparatus equipped with a Geiger instrument as a graph of diffraction by irradiation of Cu-Kα rays.

The abscissa represents the diffraction value (2θ: Cu-Kα) and the ordinate represents the relative intensity (R, I) of the diffraction line.

3 shows the degradation rate-exhaust rate characteristics of each compound.

Example 1

3-acetylaminoaniline (15 parts) was reacted with n-amyl chloride (32 parts) in the presence of anhydrous sodium carbonate (21.2 parts) at 120-130 ° C. for 4 hours to give 3-acetylamino-N, N-di-n -Pentylaniline (coupling component) is obtained, and the resulting 3-acetylamino-N, N-di-n-pentylaniline is dissolved in methanol (200 parts). Separately, 2-cyano-4-nitro-6-chloroaniline (19.8 parts) is diazotized with nitrosulfuric acid at a low temperature (10 ° C or lower) to obtain a diazo solution, which is 5 ° C or lower in the coupling liquid described above. Drop by drop at the temperature of.

After the coupling is completed, the precipitated product is filtered, washed with water and dried to obtain 44.8 parts of the dye of formula (1).

The yield is 90% based on the diazo component.

The dye of Structural Formula (1) (3 parts) was finely ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to form a dispersible form and sulfuric acid of a higher alcohol. The salt bath is made uniformly dispersed in water together with the ester (3 parts).

Testosterone spun yarn (100 parts) (polyester fiber manufactured by Toray Co., Ltd.) was immersed in a salt bath and dyed at 130 ° C. for 60 minutes, and the dyed yarn was sodium hydroxide (3 parts), hydrosulfite (3 parts), beta After washing for 10 minutes at 85 ° C. in a solution of puppet surfactant (3 parts) and water (3000 parts), the dyed spun yarn is rinsed with water and dried to obtain a clear, bright, solid, dyed blue product. .

Example 2

3-propionylaminoaniline (16.4 parts) was placed in a solvent of methylcellulose (100 parts) and water (100 parts) and n-amine toluenesulfonate (5 8.1 parts) in the presence of anhydrous sodium carbonate (12.7 parts). To react with 3-propionylamino-N, N-di-n-pentylaniline (the cuffing component).

In the same manner as in Example 1, 1,2-cyano-4-nitro-6-chloroaniline is diazotized and coupled with the coupling component described above to obtain 45.1 parts of the dye of formula (2). The yield is 88% based on the diazo component.

The dye (93 parts) of the structural stone (2) was made into a finely dispersible form with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) in the following Example 1 The dyeing process is made in the same manner as in the dyeing, and the dye is obtained to give a bright, dyed blue product which is dark and bright.

Example 3

3-acetylaminoaniline (15 parts) was reacted with n-hexyl chloride (36.2 parts) in the presence of anhydrous sodium carbonate (21.2 parts) for 4 hours at 120 ° C to 130 ° C for 3-acetylamino-N, N-di- n-hexylaniline (coupling component) is prepared.

Prepared by dissolving the coupling component in methanol (200 parts) and separately diazotizing 2-cyano-4-nitro-6-chloroaniline (19.8 parts) with nitrosulfuric acid at low temperature (10 ℃ or less) A solution of the coupling component described above is added dropwise to the prepared diazo mother solution at a temperature of 5 ° C or lower.

After coupling is complete, the precipitated product is filtered and washed with water to obtain 47.4 parts of the dye of formula (3).

The yield is 90% based on the diazo component.

λmax, 603 nm (in dimethylformamide)

Melting Point ： 137-139 ℃

The dye (3 parts) of formula (3) was ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to make a dispersible form and sulfate ester of a higher alcohol. (3 parts) together with water to prepare a salt bath.

100 parts of Tetron spun yarn (polyester fiber manufactured by Toray Co., Ltd.) was immersed in a salt bath, dyed at 130 ° C. for 60 minutes, dried, and then sodium hydroxide (3 parts), hydrosulfite (3 parts), and betaine type surfactant ( 3 parts) and water (3000 parts) in a liquid wash at 85 ℃ for 10 minutes.

Rinse the dyed yarn to obtain a clear, blue, dyed product that is dry, dark, bright and solid.

Example 4

3-propionylaminoaniline (16.4 parts) was converted to n-heptyl p-toluenesulfonate (64.8 parts) in the presence of anhydrous sodium carbonate (12.7 parts) in a solvent of methylcellulose (100 parts) and water (100 parts). ) And reacted at 100 ° C. for 5 hours to obtain 3-propionylamino-N, N-di-n-heptylaniline (coupling component).

In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline is diazotized and coupled with the above-mentioned coupling component to obtain 48.8 parts of the dye of formula (4). Yield, 88% based on the diazo component.

λmax, 603 nm (in dimethylformamide)

The dye of Structural Formula (4) (3 parts) was finely ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to make a dispersible form and in Example 3 Dye by preparing a dye bath in the same manner. A bright blue dyed product is obtained that is dark and bright.

Example 5

3-acetylaminoaniline (15 parts) was reacted with n-octyl bromide (19.3 parts) at 90 ° to 100 ° C. for 4 hours in the presence of anhydrous potassium carbonate (6.9 parts) to form 3-acetylamino-N-octanianiline. The reaction product was further reacted with 3-acetylamino-Nn-octyl-N-hexyl at 120 ° to 130 ° C. for 4 hours while n-hexylbromide (16.5 parts) and anhydrous potassium carbonate (6.9 parts) were added. Aniline (coupling component) is prepared.

In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline is diazotized to react with the aforementioned coupling component to obtain 45.9 parts of the dye of formula (5). Yield, 85% based on the diazo component.

λmax, 603 nm (in dimethylformamide)

The dye (3 parts) of formula (5) was ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to make a dispersible form and In the same way a dye bath is prepared and dyed. A bright, dyed blue product is obtained, which is dark and bright.

Example 6

3-acetylaminoaniline (15 parts) was reacted with n-hexyl chloride (12.1 parts) at 100 ° C. to 110 ° C. for 4 hours in the presence of anhydrous sodium carbonate (5.3 parts) to prepare 3-acetylamino-N-hexyl aniline. Then, n-amyl chloride (10.7 parts) and anhydrous sodium carbonate (5.3 parts) were added, followed by further reaction for 4 hours at 120 ° to 130 ° C. to 3-acetylamino-Nn-hexyl-Nn-pentylaniline (coupling component) Get

In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline is diazotized and combined with the coupling component described above to obtain 42.5 parts of the compound of formula (6). Yield, 83% based on the diazo component.

λmax, 603 nm (in dimethylformamide)

The dye of Structural Formula (6) (3 parts) was finely ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to form a dispersible form and sulfuric acid of a higher alcohol. A salt bath is prepared by uniformly dispersing it in water (3000 parts) together with the ester (3 parts).

100 parts of Teflon spun yarn (polyester fiber manufactured by Toray Co., Ltd.) were immersed in a dye bath and dyed at 130 ° C. for 60 minutes. After drying, the solution was washed with sodium hydroxide (3 parts), hydrosulfite (3 parts), betaphosphate surfactant (3 parts) and water (3000 parts) at 85 ° C for 10 minutes, then rinsed and dried to give a dark and bright A bright blue dyed product with fastness is obtained.

Example 7

3-propionylaminoaniline (16.4 parts) and n-heptyl p-toluenesulfonate (27 parts) were reacted in methylcellulose (200 parts) at 100 ° C. for 4 hours in the presence of anhydrous sodium carbonate (5.3 parts). 3-Propionylamino-N-heptylaniline was obtained, and then n-amyl p-toluenesulfonate (24.2 parts) and anhydrous sodium carbonate (5.3 parts) were added, followed by further reaction at 100 to 110 ° C. for 4 hours to give 3-propy. Onylamino-Nn-heptyl-Nn-pentylaniline (coupling component) is prepared.

By the method of Example 1, 2-cyano-4-nitro-6-chloroaniline is diazotized and combined with the coupling component described above to obtain 45.9 parts of the dye of formula (7). Yield, 85% based on the diazo component.

λmax, 602nm (in dimethylformamide)

Dye (3 parts) of formula (7) was finely ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to form a dispersible form. The dye bath is prepared and dyed to obtain a bright, dyed blue product that is dark, bright and solid.

Example 8

3-acetylaminoaniline (15 parts) and n-octylbromide (19.3 parts) were reacted for 4 hours at 100 ° C. in the presence of anhydrous sodium carbonate to prepare 3-acetylamino-Nn-octylaniline, followed by n-amylbromide ( 15.1 parts) and anhydrous sodium carbonate (5.3 parts) are added and further reacted at 120 to 130 ° C. for 4 hours to obtain 3-acetylamino-Nn-octyl-Nn-pentylaniline (coupling component).

By the method of Example 1 2-cyano-4-nitro-6-chloroaniline is diazotized and combined with the coupling component described above to obtain 43.8 parts of the dye of formula (8). Yield, 81% based on the diazo component.

λmax, 601 nm (in dimethylformamide)

Dye (3 parts) of formula (8) was finely ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to form a dispersible form. The dye bath is prepared and dyed to obtain a bright, dyed blue product that is dark, bright and solid.

Example 9

3-acetylamino-N, N-di-n-pentylaniline was synthesized by the method of Example 1 and the product (29.0 parts) was dissolved in methanol (200 parts) to obtain a coupler liquid. 2-cyano-4-nitro-6-bromoaniline (24.2 parts) was diazotized with nitrosulfuric acid at low temperature (10 ° C or lower) and the resulting diazo solution was 5 ° C or lower in the coupler liquid. Drop one by one. After the coupling was completed, the precipitated product was filtered and washed with water to dry 2-cyano-4-nitro-6-bromo-2'-acetylamino-4 '-(N, N-di-n-pentyl)- Obtain amino-1,1'-azobenzene.

The total amount of the product was dissolved in dimethylformamide (250 parts), 1 cyanide (10 parts) was injected at room temperature over 2 hours, and then stirred at room temperature for 10 hours to complete the reaction. The insoluble organics were filtered off and the filtrate was poured into methanol (1000 parts) to precipitate precipitated crystals and washed with water to obtain 40.0 parts of dye of formula (9). Total yield 81.8%

λmax, 647 nm (in dimethylformamide)

Example 10

3-Propionylamino-N, N-pentylaniline was synthesized by the method of Example 2 and the product (30.4 parts) was dissolved in methanol (200 parts) to obtain a coupler liquid. In the same manner as in Example 9, 2-cyano-4-nitro-6-bromoaniline was diazotized and combined with the coupler described above to produce 2-cyano-4-nitro-6-bromo-2'-propy. Onylamino-4 '-(N, N-di-n-pentyl) -amino-1,1'-azobenzene is obtained.

The product was dried and reacted with copper cyanide in the same manner as in Example 9 to convert to a cyano compound to prepare 40.2 parts of the dye of formula (10). Overall yield 80%

λmax, 645 nm (in dimethylformamide)

[Comparative Example]

The results of Table 1 compare the degradation resistance and dyeing properties of the compounds according to the present invention with known dyes.

TABLE 1

Reference (1) Decomposition Resistance (decomposition rate)

Decomposition Ratio (%) = 100 ×

Treatment aid ： 140 degrees Celsius * 30 minutes, pH 7

The composition of the salt bath ：

Degradation rate is a numerical representation of the pH sensitivity, the lower the decomposition rate means less decomposition, so the lower the decomposition rate is good.

Dyeability (exhaust rate) of reference (2)

Exhaust Rate (%) = 100 ×

Dyeing condition ： 130 ℃ × 60 minutes, pH 5

3 is a chart showing the decomposition rate in the vertical direction and the exhaust rate in the horizontal direction with respect to the data in Table 1. FIG. Dye with a low decomposition rate and a large exhaust rate, that is, dyes in the upper right side of FIG. 3, is of practical value. Only the dyes of the present invention are located on the upper right side of FIG. 3, which indicates that the dyes of the present invention have excellent practical value.

Preparation of the dye having a special crystalline form and dyeing method of hydrophobic fibers using the same is as follows.

Example 11

2-cyano-4-nitro-6-chloroaniline (19.8 parts) is diazotized with nitrosulfuric acid to obtain a diazo solution. 3-Acetylamino-N, N-di-n-pentylaniline (29 parts) is dissolved in methanol (150 parts), ice is obtained, and the aforementioned diazo solution is added and coupled while maintaining at 0 ° C to 5 ° C. After completion of the reaction, the precipitate was filtered and washed with 2-cyano-4-nitro-6-chloro-2'-acetylamino-4 '-(N, N-di-n-pentyl) amino-1,1'- 150 parts of azobenzene wet cakes (corresponding to 43.8 parts when dried) are obtained. X-ray powder diffraction of the product is shown in FIG.

The wet cake (150 parts) is dispersed in 1500 parts of water, heat treated at 95 ° C. for 3 hours while stirring, cooled, and the cake is filtered and washed with water to obtain 135 parts of wet dye cake (corresponding to 43.8 parts when dried). X-ray powder diffraction of the dye is shown in FIG.

2-cyano-4-nitro-6-chloro-2'-acetylamino-4 '-(N, N-di-n-pentyl) amino-1,1'-azobenzene having the above specific crystalline form (3 Part 3) was finely ground together with naphthalene-β-sulfonic acid / formalin condensate (3 parts) and sodium lignosulfonate (1.5 parts) to form a dispersible form, followed by sulfate esters with sulfuric acid of higher alcohol (3 parts). And uniformly dispersed in water (3000 parts) with to prepare a salt bath.

100 parts of Tetoron spun yarn (polyester fiber manufactured by Toray Co., Ltd.) (100 parts) were immersed in a salt bath, dyed at 130 ° C. for 60 minutes and dried, and then dyed spun yarn was treated with sodium hydroxide (30 parts) and hydrosulfite (3 parts). ), Washed with beta-type positive surfactant (3 parts) and water (3000 parts) at 85 ° C for 10 minutes. The dyed yarn is then rinsed off and dried to obtain a bright blue dyed product that is dark, bright and solid. This dyed product has a uniform depth and no spots due to the condensation of the dye.

Example 12

2-cyano-4-nitro-6-chloro-2'-acetylamino-4 '-(N, N-di-n-pentyl) prepared by diazotization and coupling in the same manner as in Example 11 A wet cake of amino-1,1'-azobenzene (150 parts) (corresponding to 43.9 parts when dried) was dissolved in water (1500 parts), acetic acid (100 parts) was added, and stirred at 90 ° C. for 3 hours. Heat treatment. The product is cooled, filtered and washed with water to obtain 140 parts of wet dye cake (corresponding to 43.5 parts of dry dye). X-ray powder diffraction of the dye is as in FIG.

As a result of dyeing in the same manner as in Example 11 using the prepared dye, excellent results were obtained as in Example 11.

Example 13

2-cyano-4-nitro-6-chloro-2'-acetylamino-4 '-(N, N-di-n-pentyl) amino prepared by diazotization and coupling in the same manner as in Example 11 Disperse the wet cake (150 parts) (corresponding to 43.9 parts when dried) of -1,1'-azobenzene in water (1500 parts), add naphthalenesulfonic acid / formalin condensate (50 parts), and then stir 90 Heat treatment is carried out for 2 hours at ℃. The product is cooled, filtered and washed with water to obtain 136 parts of wet dye cake (corresponding to 43.6 parts of drying). X-ray powder diffraction of the dye is as in FIG.

Dyeing was carried out in the same manner as in Example 11 using the prepared dyes to obtain excellent dyeing results as in Example 11.

Claims (1)

A method of preparing a monoazo compound of general formula (I) by reacting a compound of general formula (II) with a compound of general formula (III).

(Wherein R ¹ is a methyl or ethyl group, R ² and R ³ are each an alkyl group of C ₅ to C ₈ and Z is a chlorine or cyano group.)

Images