JPH0420950B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a method for producing a disazo compound. More details: 1 Diamine of formula (2) and 1 mole of amine of formula (3) (X in formula (3) is a sulfonic acid group, a carboxyl group,
Phenyl group optionally substituted with methyl group, methoxy group or chlorine atom; Naphthyl group substituted with 1 to 3 sulfonic acid groups; C _1-3 optionally substituted with carboxyl group or sulfonic acid group R represents a hydrogen atom or a methyl group. ) and 1 mol of the compound of formula (4) (Z ₃ in formula (4) represents a chlorine atom or a fluorine atom.) Condensation in any order gives formula (5) (In formula (5), X, R and Z ₃ represent the same meanings as above.) A compound represented by formula (5) is obtained, and then the compound of formula (5) is diazotized to produce 1-amino-8-naphthol 3,6 disulfone. After acidic coupling with 0.5 mol of acid at pH 2 to 4, alkali coupling at pH 4 to 9 yields formula (6). (In formula (6), X, R and Z ₃ represent the same meanings as above.) A compound represented by the formula (6) is obtained, and then 1 mole of nicotinic acid or isonicotinic acid is added to the compound of formula (6) in water for 50 to 50 minutes.
Formula (1) characterized by reaction at 100℃ (In equation (1), one of Z ₁ and Z ₂ is

[Formula] (the carboxyl group is bonded to the 3 or 4 position), and the other represents a chlorine atom or a fuso atom. Also, A ^- is an anion, m is 1
Or represents 2. In addition, X and R represent the same meanings as above) Method 2 for producing a disazo compound represented by 1 mol of diamine of formula (2) and Formula (4) (In formula (4), Z ₃ represents a chlorine atom or a fluorine atom.) After condensation with 1 mole of the compound represented by the formula, diazotization, acidic coupling at pH 2 to 4, and further acidic coupling at pH 4 to
After alkali coupling in step 9, formula (3) (In formula (3), X is a sulfonic acid group, a carboxyl group, a methyl group, a methoxy group, or a phenyl group which may be substituted with a chlorine atom; a naphthyl group substituted with 1 to 3 sulfonic acid groups; a carboxyl group or a C _1-3 alkyl group or a hydrogen atom which may be substituted with a sulfonic acid group, R represents a hydrogen atom or a methyl group) to form a compound represented by the formula (6). (In formula (6), X, R and Z ₃ represent the same meanings as above.) Obtain the compound represented by the formula (6), and then add 1 mole of nicotinic acid or isonicotinic acid to 1 mole of the compound of formula (6) in water. Formula (1) characterized by reaction at 50 to 100°C (In equation (1), one of Z ₁ and Z ₂ is

[Formula] (the carboxyl group is bonded to the 3 or 4 position), and the other represents a chlorine atom or a fuso atom. Also, A ^- is an anion, m is 1
Or represents 2. The present invention also relates to a method for producing a disazo compound represented by (X and R have the same meanings as above). Reactive dyes for cellulose fibers are used in large quantities because they have superior fastness and brightness compared to other dyes for cellulose fibers. For example, reactive dyes with reactive groups such as dichlorotriazinyl, monochlorotriazinyl, fluorochloropyrimidinyl, dichloroquinoxazinyl, methylsulfonylchloropyrimidinyl, vinylsulfonyl, sulfatoethylsulfonyl, etc. are used as acid binders. or substances that release acid binders by the action of heat (e.g., sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium metasilicate, trisodium phosphate, triphosphate)
Adjust the pH of the dye bath to 10 or higher by using potassium, sodium pyrophosphate, potassium pyrophosphate, sodium bicarbonate, sodium trichloroacetate) alone or in combination of two or more,
Cellulose fibers are dyed at temperatures below 100°C in the presence of neutral electrolytes such as sodium chloride and potassium sulfate. On the other hand, mixed fiber materials (blends) containing cellulose fibers are increasingly being used as textile materials for clothing, and among them, blends of polyester fibers and cellulose fibers, especially cotton (hereinafter abbreviated as T/C blends), are becoming more suitable for clothing. It has come to be widely used for reasons such as excellent quality and economical efficiency. And T/C
The following methods have generally been used to dye blends using reactive dyes and disperse dyes. (i) One-bath two-step method First, the polyester fiber side is dyed with a disperse dye by a carrier dyeing method, a high temperature dyeing method, etc., and then the cellulose fiber side is dyed with a reactive dye in the same bath. Or by the reverse method. (ii) Two-bath method First, the polyester fiber side is dyed by the method described above, and then the cellulose fiber side is dyed in a separate bath. Or by the reverse method. However, recently, in order to shorten the dyeing time, rationalize the dyeing process, and save energy, efforts have been made to use the T/C mixture in the same bath and finish the dyeing in one dyeing process (one-bath, one-step method). . However, there are several obstacles to dyeing a T/C blend with a reactive dye and a disperse dye in one bath and one step using a high temperature method or the like. For example, acid binders or substances releasing acid binders necessary for dyeing reactive dyes aggregate or disperse disperse dyes in the dyebath. In addition, when dyeing polyester fibers in an aqueous medium at high temperatures such as 130°C, reactive dyes are hydrolyzed by acid binders, etc.
For example, it does not stain cellulose fibers. Therefore, there has been a strong demand for the development of reactive dyes that can dye T/C mixtures in one step in one bath. As a result of extensive research to meet these demands, the present inventors discovered that the compound represented by formula (1) has extremely high suitability for the T/C mixed one-bath one-step dyeing method, and thus achieved the present invention. It is ivy. The compound obtained by the production method of the present invention not only shows excellent suitability for T/C mixed one-bath one-stage dyeing method, but also has sufficient suitability for dyeing cellulose fibers by conventional methods. However, it is noteworthy that the novel compounds of the present invention can be used in the absence of an acid binder or a substance that releases an acid binder, or in the absence of a dyebath.
In the presence of disperse dyes, simply by coexisting with a buffering agent necessary to maintain the pH at 4-10, especially 5-9.
The advantage is that the T/C blend can be dyed in one step in one bath at a dyeing temperature of 100 to 150°C. When the compound (dye) of the present invention is used together with a disperse dye in a one-bath one-step dyeing method of T/C mixture, the T/C mixture does not cause aggregation of the disperse dye or decomposition of the disperse dye or reactive dye. Can be dyed uniformly. The compound of the present invention dyes cellulose fibers in navy blue or dark green hues, and the dyed products have excellent wet fastness, chlorine fastness, and light fastness. The compound obtained by the production method of the present invention can be used for cotton, recycled viscose fiber, cellulose fiber such as hemp, T/C
The most remarkable effect is obtained when mixed dyeing is carried out, but other mixed fiber materials such as cellulose fiber and triacetate fiber, polyacrylonitrile fiber, modified polyacrylic fiber, polyamide fiber, wool, silk, etc. Excellent effects can be obtained even when dyeing the cellulose fiber side. In these cases, by using disperse dyes, basic dyes, cationic dyes, acid dyes, acidic metal-containing dyes, etc., it is possible to obtain a dyed blend in which each fiber forming the blend is uniformly dyed. The compound obtained by the production method of the present invention is synthesized, for example, by the following method. 1 mol of diamine of formula (2), and 1 mol of amine of formula (3) (wherein X and R represent the same meanings as above) and 1 mol of the compound of formula (4). (In the formula, Z ₃ represents a chlorine atom or a fluorine atom) Condensed in any order to form the formula (5) The compound is obtained. Next, the compound of formula (5) was diazotized by a conventional method to obtain 1
By acidic coupling with 0.5 mol of -amino-8-naphthol-3,6-disulfonic acid at pH 2-4 and then alkali coupling at pH 4-9, formula (6) can be obtained. A disazo compound is obtained. In this case, urea,
A coupling promoter such as thiourea may also be added. Further, the compound of formula (6) is reacted with 1 mole of nicotinic acid or isonicotinic acid in water at 50 to 100°C to obtain a compound of formula (1). Also, to obtain the compound of formula (6), diamine 1 of formula (2)
After condensing 1 mole of the compound represented by the formula (4) with 1 mole of the compound represented by the formula (4), diazotization is performed by a conventional method, and after coupling with 1-amino-8-naphthol-3,6-disulfonic acid in the same manner as in the above method, the compound represented by the formula (4) is formed. Condensation with the amine represented by (3) or formula (7) It can also be obtained by condensing 0.5 mol of a disazo compound represented by formula (3) and 1 mol of an amine represented by formula (3) with 1 mol of a compound represented by formula (4) in any order. To obtain the target product from the reaction solution, a conventional salting out method or acid precipitation method is used. Alternatively, the reaction solution can be directly spray-dried. Next, specific examples of the compound represented by formula (2), the compound represented by formula (3), and the compound represented by formula (4) used in producing the compound of formula (1) are listed. . Compound represented by formula (2); 1,3-phenylenediamine-4-sulfonic acid 1,4-phenylenediamine-2-sulfonic acid Compound represented by formula (3);

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[Formula] NH ₃ , NH ₂ CH ₃ , NH(CH ₃ ) ₂ , NH ₂ CH ₂ CH ₃ NH ₂ CH ₂ CH ₂ , NH ₂ CH ₂ COOH,
NH ₂ CH ₂ CH ₂ COOH NH ₂ CH ₂ CH ₂ SO ₃ H, NH ₂ CH (CH ₃ ) ₂ Compound represented by formula (4); 1,3,5-trichlorotriazine 1,3,5-trifluoro A ^- in the triazine formula (1) is a negative charge required to balance the positive charge of the nitrogen atom of one or two pyridine nuclei in the formula (1), and OH ^- , C1 from the reaction solution. -Also ^, it may be COO ^- or SO ₃ ^- in the molecule. Next, a method for dyeing cellulose fibers and cellulose fiber-containing fiber materials (blended fibers) using the compound obtained by the production method of the present invention will be described. When dyeing cellulose fibers using the batch dyeing method using the compound obtained by the production method of the present invention,
A dyebath is usually prepared with an inorganic salt such as sodium sulfate or sodium chloride and the compound of the invention, and the fibers are immersed and dyed for 10 to 60 minutes at 50 to 90°C followed by an acid binder such as hydrogen carbonate. sodium,
Sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium metasilicate, trisodium phosphate, tripotassium phosphate, sodium pyrophosphate, potassium pyrophosphate, and sodium trichloroacetate are added singly or in a mixture of two or more. , further dyeing is carried out at the same temperature for 20 to 60 minutes. In this case, the acid binder may be added to the dye bath from the beginning, or it is possible to treat the dye with a separate bath containing the acid binder and an inorganic salt after dyeing. In addition, when dyeing T/C mixed fibers by the dip dyeing method using the compound (dye) of the present invention, the compound disperse dye of the present invention and an inorganic salt may be added, and if necessary, the pH value of the dye bath may be adjusted to 5.
From buffers (e.g., mixtures of acetic acid and sodium acetate, mixtures of monopotassium phosphate and disodium phosphate, mixtures of monosodium phosphate and disodium phosphate), surfactants, reduction inhibitors, etc. Prepare a dye bath, immerse the fibers in this dye bath, and
Heat to ~150°C and stain for 20 to 90 minutes.
It is also possible to dye only cellulose fibers using the method described above. The compound obtained by the production method of the present invention makes it possible to dye T/C mixture in one step in one bath with the coexistence of disperse dye, from the viewpoint of shortening dyeing time, streamlining the dyeing process, and saving energy. The economic effect is extremely large. Next, the present invention will be specifically explained with reference to Examples.
In the examples, "part" means "part by weight", "%" means "% by weight", sulfonic acid group and carboxyl group are represented in free form, and the positive charge of the nitrogen atom of the pyridine nucleus is expressed in the solution or molecule. It is assumed that it has been neutralized by OH ^- , C1 ^- or COO ^- , SO ₃ ^- in the molecule. Example 1 Formula (8) 11.4 parts of the disazo compound represented by was dissolved in 50 parts of water, and to this solution was added a solution consisting of 2.5 parts of nicotinic acid, 25 parts of water, and 0.9 parts of sodium hydroxide. This mixed solution was heated to 90°C and reacted for 10 hours.
By salting out the reaction solution with sodium chloride, separating the resulting crystals, and drying at 80°C, formula (9),
12.3 parts of a dark blue disazo compound mixture (λmax 610 nm (in water)) represented by formula (10) was obtained. (In the formula, one of Z ₄ and Z ₅ is

The result of high performance liquid chromatography analysis (wherein [formula] is the other representing a chlorine atom) was a mixture of 68% (9) and 31% (10). The disazo compound of formula (8) used in the above example was obtained as follows. Add 3.9 parts of cyanuric chloride and a small amount of surfactant to cold water.
Add 50 parts and disperse well. In this suspension, 1,
A solution of 3.9 parts of 3-phenylenediamine-4-sulfonic acid dissolved in 30 parts of water is added dropwise over 30 minutes. Next, adjust the pH to 6.0 with a 10% sodium carbonate aqueous solution,
Add ice and stir for 1 hour while maintaining the temperature at 5-10°C.
Ice was added to the resulting reaction solution to bring the temperature to 0-5°C, and the temperature was adjusted to 40%.
Add 3.7 parts of sodium nitrite aqueous solution. Add 4.3 parts of concentrated hydrochloric acid to this mixture and stir at 5-10°C for 1 hour. Excess nitrous acid is then decomposed with sulfamic acid to obtain a diazonium salt solution. A solution prepared by dissolving 3.4 parts of 1-amino-8-naphthol-3,6-disulfonic acid in 40 parts of water at pH 5.5-6.0 was added to the above diazonium salt solution with ice and diluted for 5-10 minutes.
Add dropwise over 1 hour while keeping at ℃. During this time, 10% sodium carbonate aqueous solution was added dropwise at the same time to make the pH 2.5-3.0.
Keep it. After the addition is complete, the mixture is stirred for another 2 hours to complete the coupling reaction (acidic coupling).
Then the pH was adjusted by adding 10% aqueous sodium carbonate solution.
Stir at 7.0 to 7.5 for 1 hour and perform alkali coupling. Next, 2.9 parts of 4-aminobenzoic acid was added to 15 parts of water at pH
Add the aqueous solution containing pH 6.0-7.0 to the above reaction solution, and stir at 50-60°C for 2 hours while maintaining the pH at 7.0-8.0. Salting out with sodium chloride was performed, and the precipitate was separated and dried at 80°C to obtain 19 parts of a disazo compound of formula (8). Reference example 1 2 parts of the compound obtained in Example 1 (mixture of formula (9) and formula (10)), 60 parts of Glauber's salt, 2 parts of disodium phosphate,
A dye bath was prepared consisting of 0.5 parts of monopotassium phosphate, 1 part of sodium metanitrobenzenesulfonate, and 934.5 parts of water. The pH value of the dye bath at this time was 7. Add 50 parts of scouring and bleaching unsilced cotton knitted fabric to this dye bath and dye it for 30 minutes with stirring.
The temperature was raised to ℃ and dyed at that temperature for 60 minutes. The PH value after staining was 7, unchanged from before the start of staining. After dyeing, the dyed product was washed with water, soaped with 1,000 parts of an aqueous solution containing 2 parts of an anionic surfactant at 100° C. for 10 minutes, washed with water, and dried to obtain a dark blue dyed product. This product had excellent wet fastness, chlorine fastness, light fastness, and sweat/sunlight fastness. Reference Example 2 1 part of the compound obtained in Example 1 (mixture of formula (9) and formula (10)), Kayalon polyester, Navy Blue EX-SF200 (disperse dye manufactured by Nippon Kayaku) 0.5 part, Glauber's salt 80 parts , 1 part of sodium metanitrobenzenesulfonate, 2 parts of a formalin condensate of naphthalene sulfonic acid (dispersant), and adjusted to pH 70 with a buffer consisting of disodium phosphate and monopotassium phosphate, with a total volume of 1000 parts. , 50 parts of a polyester fiber/cotton (50/50) blended fabric was introduced, the temperature was raised to 130°C for 20 minutes, and dyeing was carried out at this temperature for 60 minutes. After washing with water, soaping for 20 minutes at 100°C in 1000 parts of water containing 2 parts of anionic surfactant and 2 parts of sodium carbonate.
Then, it was washed with water and dried. A dyed product was obtained in which both the polyester fiber side and the cotton side were uniformly dyed in dark blue. Reference Example 3 1 part of the compound obtained in Example 1 (mixture of formula (9) and formula (10)), Kayalon Polyester Navy Blue
50 parts of polyester fiber/cotton (50/50) blended fabric was added to a dye bath with a total volume of 1000 parts prepared from 0.5 part of EX-SF200 and 80 parts of Glauber's salt, and the temperature was raised to 130 minutes in 20 minutes. Stained for minutes. Next, the same treatment as in Example 3 was performed to obtain the polyester fiber side.
A dyed product was obtained in which both the cotton sides were uniformly dyed in dark blue. Example 2 Formula (11) 12.4 parts of a disazo compound represented by is dissolved in 300 parts of water, and 5.0 parts of nicotinic acid was added. Then 5%
The pH was adjusted to 6.0 with sodium hydroxide and heated to 90°C. While maintaining the pH at 5.5 to 6.0 by adding a 5% aqueous sodium hydroxide solution as necessary, the mixture was stirred at the same temperature for 8 hours. The reaction solution was salted out with sodium chloride, and the precipitate was separated and dried under reduced pressure at 60°C to obtain 13.5 parts of a dark green disazo compound represented by formula (12).
(λmax630nm (water)) The disazo compound represented by formula (11) used in the above example was obtained as follows. Dissolve 9.2 parts of 4-aminotoluene-2-sulfonic acid in 80 parts of water in a neutral state, add 20 parts of ice, and dissolve 0-5
A small amount of surfactant and 9.2 parts of cyanuric chloride were added to the solution at 0-5°C while maintaining the pH at 6.0-7.0 with a 10% aqueous sodium carbonate solution.
Stir for hours. 1,4-phenylenediamine-2-sulfonic acid
A neutral solution of 9.0 parts dissolved in 20 parts of water was added to the above reaction solution, and the pH was adjusted with a 10% aqueous sodium carbonate solution.
The mixture was stirred at 5-10°C for 4 hours while maintaining the temperature at 6.0-6.5. Ice was added to the resulting reaction solution to bring the temperature to 0-5°C, and the temperature was kept at 40°C.
% zinc sodium nitrate aqueous solution 8.8 parts and concentrated hydrochloric acid
12.0 parts were added and stirred at 0-10°C for 1 hour, and then excess nitrous acid was decomposed with sulfamic acid. Thiourea is added to the viscous diazonium salt solution thus obtained.
30 parts were added. A solution of 6.2 parts of 1-amino-8-naphthol-3,6-disulfonic acid dissolved in 40 parts of water at a pH of 5.5-6.0 was added dropwise to the diazonium salt solution over 20-30 minutes, followed by addition of 10% sodium carbonate. PH by aqueous solution
The mixture was stirred at 10-15°C for 5-8 hours while maintaining the temperature at 3.5-4.0°C. (Acidic coupling) Next, the pH was adjusted to 8.0-8.5 with a 10% aqueous sodium carbonate solution, stirred for 2 hours, and alkaline coupling was performed. Salting out with sodium chloride, separating the precipitate and drying, formula (11)
21 parts of a disazo compound represented by was obtained. Reference Example 4 A dye bath was prepared with 2 parts of the disazo compound of formula (12) obtained in Example 5, 80 parts of Glauber's salt, and 1,000 parts of water,
Dip 50 parts of cotton stockinette into this dye bath and dye at 80℃.
After staining for 30 minutes, 20 parts of sodium carbonate was added, followed by staining at the same temperature for 60 minutes. The dyed product was then treated and dried in the same manner as in Example 2 to obtain a dark green dyed product, which had excellent wet fastness and light fastness. Example 3 Formula (13) Dissolve 12.8 parts of the disazo compound represented by in 300 parts of water, add 3.7 parts of isonicotinic acid, adjust the pH to 6.5 with a 5% aqueous sodium hydroxide solution, and heat at 75-80°C.
The mixture was stirred for 24 hours. The reaction solution was salted out with sodium chloride, and the precipitate was separated and dried to obtain the compound of formula (14).
Got 13.6 copies. (λmax610nm (water)) Equation (14) Note that the compound of formula (13) was produced according to the method described in Example 1. Dyeing was performed using the disazo compound of formula (14) according to Example 2 to obtain a dark blue dyed product. It had excellent wet fastness, chlorine fastness, light fastness, and sweat fastness to light. Reference Example 5 4 parts of the disazo compound of formula (14) obtained in Example 7, Kayalon Polyester Navy Blue EX
- Contains 2 parts of SF200, 80 parts of Glauber's salt, 2 parts of sodium metanitrobenzenesulfonate, and 2 parts of a formalin condensate of naphthalene sulfonic acid, and the pH was adjusted with a buffer consisting of di-sodium phosphate and monopotassium phosphate.
A total volume of 1000 parts of the solution adjusted to 7.0 was injected into a cheese dyeing machine (manufactured by Nippon Senzo Kikai Co., Ltd.). Contains 100 parts of polyester fiber/cotton (50/50) blended yarn.
The temperature was raised to 130°C for 30 minutes, and staining was carried out at this temperature for 30 minutes. It was then treated in the same manner as in Example 3, washed with water and dried. A dyed product was obtained in which both the polyester fiber side and the cotton side were uniformly dyed in dark blue. Example 4 Formula (15) 13.5 parts of a disazo compound represented by is dissolved in 300 parts of water, 2.5 parts of nicotinic acid was added, and the pH was adjusted to 6.5 with a 5% aqueous sodium hydroxide solution. This solution was heated to 60° C. and stirred for 10 hours while maintaining the pH at 6.0 to 6.5 with a 10% aqueous sodium carbonate solution. After salting out the reaction solution with sodium chloride and separating the precipitate,
Vacuum drying at °C yielded 14.3 parts of a dark blue mixture of disazo compounds (λmax 610 nm (H ₂ O)) represented by formulas (16) and (17). Formula (16) Formula (17) (In the formula, one of Z ₆ and Z ₇ is

[Formula] The other represents a fluorine atom) The results of high performance liquid chromatography analysis are 73% for formula (16) and 20% for formula (17)
It was a mixture consisting of the following proportions. Examples 5 to 57 Disazo compounds of formula (18) were produced according to Examples 1 to 4, and cotton was dyed according to Reference Example 1. The following table shows the compound represented by formula (2) used to produce the compound of formula (18), the compound represented by formula (3), the bonding position of the carboxyl group in the pyridine nucleus, and the λmax ( water), shows the hue when cotton is dyed.

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Claims (1)

[Claims] 1 Diamine of formula (2) and 1 mole of amine of formula (3) (X in formula (3) is a sulfonic acid group, a carboxyl group,
Phenyl group optionally substituted with methyl group, methoxy group or chlorine atom; Naphthyl group substituted with 1 to 3 sulfonic acid groups; C _1-3 optionally substituted with carboxyl group or sulfonic acid group R represents a hydrogen atom or a methyl group. ) and 1 mol of the compound of formula (4) (Z ₃ in formula (4) represents a chloro atom or a fluorine atom.) Condensation in any order gives formula (5) (In formula (5), X, R and Z ₃ represent the same meanings as above.) A compound represented by formula (5) is obtained, and then the compound of formula (5) is diazotized to produce 1-amino-8-naphthol 3,6 disulfone. After acidic coupling with 0.5 mol of acid at pH 2 to 4, alkali coupling at pH 4 to 9 yields formula (6). (In formula (6), X, R and Z ₃ represent the same meanings as above.) A compound represented by the formula (6) is obtained, and then 1 mol of nicotinic acid or isonicotinic acid is added to the compound of formula (6) in water for 50~
Formula (1) characterized by reaction at 100℃ (In formula (1), one of Z ₁ and N ₂ represents [formula] (the carboxyl group is bonded to the 3 or 4 position), and the other represents a chlorine atom or a fluorine atom. Also, A ^- anion, m is 1
Or represents 2. In addition, X and R represent the same meanings as above) Method 2 for producing a disazo compound represented by 1 mol of diamine of formula (2) and Formula (4) (In formula (4), Z ₃ represents a chlorine atom or a fluorine atom.) After condensation with 1 mol of a compound represented by
Acidic coupling at PH2-4, and further at PH4-9
After alkali coupling with formula (3) (In formula (3), X is a sulfonic acid group, a carboxyl group, a methyl group, a methoxy group, or a phenyl group which may be substituted with a chlorine atom; a naphthyl group substituted with 1 to 3 sulfonic acid groups; a carboxyl group or a C _1-3 alkyl group or a hydrogen atom which may be substituted with a sulfonic acid group, and R represents a hydrogen atom or a methyl group) is condensed with a compound represented by formula (6) (In formula (6), X, R and Z ₃ represent the same meanings as above.) Obtain the compound represented by the formula (6), and then add 1 mole of nicotinic acid or isonicotinic acid to 1 mole of the compound of formula (6) in water. Formula (1) characterized by reaction at 50 to 100°C (In formula (1), one of Z ₁ and Z ₂ represents [formula] (the carboxyl group is bonded to the 3 or 4 position), and the other represents a chlorine atom or a fluorine atom. Also, A ^- anion, m is 1
Or represents 2. In addition, X and R represent the same meanings as above) A method for producing a disazo compound represented by: