JP5201283B1 - Azo pigment and method for producing the same - Google Patents

Abstract

【選択図】なしThe present invention provides an azo pigment having a weak secondary agglomeration of pigment, excellent dispersibility, high coloring power and sharpness, and excellent workability during use, and a method for producing the same.
A specific azo pigment having an apparent density defined by JIS K 5101-12-1 of 0.04 g / mL to 0.14 g / mL. The azo pigment is produced by a reaction between a diazo component represented by the following formula and a naphthalene-based orthohydroxycarboxylic acid amide as a coupler component. (In the following formulae, R13 to R17 each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a carbamoyl group, etc.)

[Selection figure] None

Description

  The present invention relates to an azo pigment and a method for producing the same.

  An azo pigment is a compound obtained by reacting a diazotized aromatic amine as a base component with a coupler component. Among them, a naphthol AS pigment is obtained from its coloring power, sharpness, and various resistances. It is used as a colorant in various fields such as printing ink, plastic, textile printing, inkjet ink, electrophotographic printing, color toner, and color filter.

  Naphthol AS pigments are usually produced by conducting a diazo coupling reaction in water. The pigment thus obtained is used for coloring an object to be colored in a wet state such as a wet cake. Further, a wet pigment is dried and used as a pigment in a dry state such as powder for coloring an object to be colored.

  Naphthol AS pigments are usually relatively difficult to finely disperse in colored materials such as varnishes, plastics, and water-based dispersion resins. Has the disadvantage of having to do. In order to eliminate this drawback, the pigment may be directly dispersed from the wet state without drying it. However, the wet pigment is likely to be frozen during storage in winter, and mold caused by various bacteria may be stored during storage in summer. There is a drawback that it tends to occur, and there is a problem that long-term storage is difficult. In addition, when dispersing the wet pigment on the object to be colored, a special device is required such as removing water. On the other hand, the pigment in the dry state does not have such a problem. However, when a colored product having excellent coloring characteristics is to be obtained, it takes time and cost to disperse with a strong force for a long time.

  A wet pigment that has not undergone drying has relatively weak aggregation between pigment particles, and is easily finely dispersed in a medium to be colored. This is because the pigment is in a soft agglomerate state in which the primary particles of the pigment adhere to each other at corners or ridges. However, by passing through the wet state as described above and subsequent drying, the primary particles are adhered to each other to form secondary particles, resulting in a hard aggregate state. In this specification, the property that the primary particles adhere to each other to form secondary particles is called secondary aggregation.

  The agglomerated state of the pigment particles has a great influence on the dispersibility of the pigment and the color characteristics of the colored product using the pigment. The colored products such as inks, paints, plastics, and color toners obtained thereby have excellent coloring power, sharpness, and the like. In the present specification, this property of being dispersible in an object to be colored in a small force and in a shorter time is called easy dispersibility.

  Generally, it is known that the smaller the primary particle diameter of the pigment, the harder the secondary aggregation occurs during drying. Therefore, as a method for alleviating secondary agglomeration, treatment with a solvent (Japanese Patent Laid-Open Nos. 56-32548, 57-168951, 57-168895, 58-120673, etc.) is known. This method is effective for easily dispersing the pigment, but the primary characteristics of the pigment to be colored tend to be inferior due to the growth of primary particles of the pigment.

  Therefore, it does not have the same disadvantages as the above-mentioned wet pigments, and does not require special equipment necessary to master the wet pigments. There is a need for dried naphthol AS pigments that can be colored and that exhibit better coloring characteristics than when colored with conventional dry pigments.

JP 56-32548 A Japanese Unexamined Patent Publication No. 57-168951 Japanese Patent Laid-Open No. 57-168952 JP 58-120673 A

  The present invention solves the problems of the prior art, azo pigments having weak secondary agglomeration of pigments, excellent dispersibility, high coloring power and sharpness, and excellent workability during use, and production thereof It aims to provide a method.

As a result of intensive studies, the present inventors have found that the above problems can be solved, and have reached the present invention.
That is, the embodiment of the present invention is represented by the general formula (1) characterized in that the apparent density defined by JIS K 5101-12-1 is 0.04 g / mL to 0.14 g / mL. The present invention relates to an azo pigment made of a compound.

General formula (1)

(In the general formula (1), R ₁ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the following general formula (2).
R ₂ is water atom, A Rukokishiru group, or a butoxycarbonyl group.
R ₃ represents a hydrogen atom, an alkyl group, an alkoxyl group, a carbamoyl group, an N-phenylcarbamoyl group, an N, N-diethylsulfamoyl group, or a benzylsulfonyl group.
R ₄ represents a hydrogen atom, a carbamoyl group, an N-phenylcarbamoyl group, or an N-methylsulfamoyl group.
R ₅ represents a hydrogen atom or an alkyl group.
R ₆ represents a hydrogen atom, an alkyl group, or an alkoxyl group. )

General formula (2)

(In general formula (2),
R ₇ is, water atom, an alkyl group, an alkoxyl group, or a halogen atom.
R ₈ represents a hydrogen atom.
R ₉ represents a hydrogen atom, an alkoxyl group, or a halogen atom.
R ₁₀ represents a hydrogen atom, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a two-Toro group.
R ₁₁ represents a hydrogen atom . )

  In an embodiment of the present invention, the azo pigment is C.I. I. Pigment Red 5, 31, 32, 146, 147, 150, 176, 184, 185, 208, 245, 258, 266, 268, 269, C.I. I. Pigment Violet 32, 50, the compound represented by the chemical formula (3), and the azo pigment which is at least one azo pigment selected from the compound represented by the chemical formula (4).

Chemical formula (3)

Chemical formula (4)

  An embodiment of the present invention also relates to an azo pigment composition comprising 0.1 to 10% by weight of a surfactant based on the azo pigment.

  In addition, an embodiment of the present invention is a method for producing an azo pigment, which includes a step of reacting an acid with a solution containing a coupler component to cause precipitation, and further reacting a diazo component to produce an azo pigment. The present invention relates to a method for producing an azo pigment comprising a compound represented by the general formula (1), wherein the apparent density defined by 5101-12-1 is 0.04 g / mL to 0.14 g / mL.

（一般式（１）中、Ｒ₁は、水素原子、ベンズイミダゾロン基、アルキルアミノアルキル基、または、下記一般式（２）で表わされる基を表わす。
Ｒ₂ は、水素原子、アルコキシル基、または、ブトキシカルボニル基を表す。
Ｒ ₃ は、水素原子、アルキル基、アルコキシル基、カルバモイル基、Ｎ−フェニルカルバモイル基、Ｎ，Ｎ−ジエチルスルファモイル基、または、ベンジルスルホニル基を表す。
Ｒ ₄ は、水素原子、カルバモイル基、Ｎ−フェニルカルバモイル基、または、Ｎ−メチルスルファモイル基を表す。
Ｒ ₅ は、水素原子、または、アルキル基を表す。
Ｒ ₆ は、水素原子、アルキル基、または、アルコキシル基を表す。）
General formula (1)

(In the general formula (1), R ₁ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the following general formula (2).
R ₂ is water atom, A Rukokishiru group, or a butoxycarbonyl group.
R ₃ represents a hydrogen atom, an alkyl group, an alkoxyl group, a carbamoyl group, an N-phenylcarbamoyl group, an N, N-diethylsulfamoyl group, or a benzylsulfonyl group.
R ₄ represents a hydrogen atom, a carbamoyl group, an N-phenylcarbamoyl group, or an N-methylsulfamoyl group.
R ₅ represents a hydrogen atom or an alkyl group.
R ₆ represents a hydrogen atom, an alkyl group, or an alkoxyl group. )

（一般式（２）中、
Ｒ₇ は、水素原子、アルキル基、アルコキシル基、または、ハロゲン原子を表す。
Ｒ ₈ は、水素原子を表す。
Ｒ ₉ は、水素原子、アルコキシル基、または、ハロゲン原子を表す。
Ｒ ₁₀ は、水素原子、アルコキシル基、ハロゲン原子、トリフルオロメチル基、または、ニトロ基を表す。
Ｒ₁₁ は、水素原子を表わす。）
General formula (2)

(In general formula (2),
R ₇ is, water atom, an alkyl group, an alkoxyl group, or a halogen atom.
R ₈ represents a hydrogen atom.
R ₉ represents a hydrogen atom, an alkoxyl group, or a halogen atom.
R ₁₀ represents a hydrogen atom, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a two-Toro group.
R ₁₁ represents a hydrogen atom . )

  Moreover, the embodiment of the present invention is a method in which a solution containing a coupler component is heated to 70 to 100 ° C. and held for 0.1 to 10 minutes, and then the solution containing the coupler component is reacted with an acid to precipitate. And a method of producing the azo pigment, further comprising reacting a diazo component to produce an azo pigment.

According to the present invention, since the secondary aggregation of the pigment is alleviated, an azo pigment having excellent dispersibility, high coloring power and sharpness, and excellent workability during use is provided, and a method for producing the same. Is done.

  Hereinafter, the present invention will be described in detail. Note that “CI” in this specification means a color index (CI).

  The azo pigment of the present invention is a compound represented by the general formula (1) characterized in that the apparent density specified by JIS K 5101-12-1 is 0.04 g / mL to 0.14 g / mL. Is an azo pigment. Here, the apparent density is a value obtained by dividing the mass of the loosely packed powder by the bulk volume occupied. The apparent density in this specification is that the dried pigment is crushed at a rotation speed of 6000 rpm and a pigment supply speed of 50 g / min by attaching a 1 mm screen to a continuous mill MF10.2 (hammer head mill) manufactured by IKA. This was used as a sample for measurement. Here, the term “dried” means that the weight loss when the pigment of the sample is dried for 2 hours in a drier kept at a temperature of 90 ° C. ± 2 ° C. is 2% or less of the weight of the pigment before drying. Refers to that.

When the apparent density is higher than 0.14 g / mL, the easy dispersibility of the azo pigment tends to be inferior. On the other hand, when the apparent density is lower than 0.04 g / mL, the pigment is likely to be scattered, and the pigment is scattered when the pigment is charged or mixed with a resin or the like, which tends to deteriorate workability.
The apparent density is a value correlated with the strength of secondary aggregation of pigment particles, which is a general index of easy dispersibility. When the primary particle diameter of the pigment is about the same, the higher the secondary aggregation, the larger the apparent density and the easier the dispersibility. Conversely, the weaker the secondary aggregation, the smaller the apparent density and the easier the dispersibility.

  The azo pigment of the present invention can be produced by acid precipitation positive coupling. As a method of acid precipitation normal coupling, a known method can be used, and an acid precipitation coupler slurry is obtained by reacting a solution containing a coupler component with an acid aqueous solution, and then a coupling reaction with a solution containing a diazo component. The method of letting it be mentioned.

  The acid used in the acid aqueous solution may be any acid as long as it dissolves in water, but it is preferable to use either hydrochloric acid or acetic acid, or a mixture of hydrochloric acid and acetic acid. Although the temperature of the acid aqueous solution during acid precipitation can be selected at any temperature, if acid precipitation is carried out at 0 to 5 ° C, the subsequent coupling reaction rate can be increased, and acid precipitation at 40 to 50 ° C. If done, it is easier to obtain a pigment with a lower apparent density. Ice may be added as necessary to maintain the acid precipitation temperature. In order to improve the reaction rate, the acid precipitation coupler slurry may be heated as necessary before or after the solution containing the diazo component is added. However, the temperature of the acid precipitation coupler slurry during the coupling reaction is preferably 50 ° C. or lower because the diazo component is easily altered and decomposed when the temperature is increased. The pH of the acid precipitation coupler slurry before adding the solution containing the diazo component is preferably 2-6. When the pH is less than 2, the reaction rate after adding the solution containing the diazo component is extremely slow, and when the pH exceeds 6, the diazo component is easily deteriorated, which is not preferable. Any acid can be used as the acid used for adjusting the pH as long as it dissolves in water, but it is preferable to use either hydrochloric acid or acetic acid, or a mixture of hydrochloric acid and acetic acid. The acid may be added in advance by using an acid used for acid precipitation in excess of the equivalent of the base of the solution containing the coupler component, or may be added in advance when the base is dissolved, or may be added to the diazo solution. A necessary amount may be added later to the coupler slurry after acid precipitation.

  A solution containing a coupler component can be prepared by adding a naphthol AS-based coupler to a heated basic aqueous solution. Moreover, water, a base, and a coupler component may be mixed at room temperature (about 15 ° C. to about 30 ° C.) and heated to be dissolved during transfer to an aqueous acid solution. The heating temperature depends on the type of naphthol AS coupler to be used, but approximately 50 ° C to 95 ° C is required. The base can be dissolved in water to dissolve the naphthol AS coupler, and any base can be used as long as it does not form an insoluble salt when neutralized with the acid aqueous solution. It is preferable to use potassium oxide from the viewpoints of cost, solubility of coupler components, waste liquid treatment, and the like.

  A solution containing a diazo component can be obtained by diazotizing an aromatic amine as a base component. A known method can be used as the diazotization method. For example, diazotization can be carried out by adding hydrochloric acid to a reslurry of the base component in ice water and dissolving it, and then adding sodium nitrite.

  Examples of the azo pigment to which the production method of the present invention can be applied include an azo pigment made of a compound represented by the general formula (1).

In R ₁ , the alkylaminoalkyl group means an N, N-dialkylaminoalkyl group. Here, 1-4 are preferable and, as for carbon number of a terminal alkyl group, 1-3 are more preferable. Moreover, 1-4 are preferable and, as for carbon number of the alkylene group couple | bonded with the terminal dialkylamino group, 1-3 are more preferable. Specifically, N, N-dimethylaminoethyl group, N, N-diethylaminoethyl group, N-ethyl-N-methylaminoethyl group, N, N-dipropylaminoethyl group, N, N-diisopropylaminoethyl Group, N, N-dimethylaminopropyl group, N, N-diethylaminopropyl group, N-ethyl-N-propylaminopropyl group, N, N-dipropylaminopropyl group, N, N-diisopropylaminopropyl group, N , N-dibutylaminopropyl group and the like. Among these, N, N-diethylaminoethyl group, N, N-dipropylaminoethyl group, N, N-diethylaminopropyl group, and N, N-dipropylaminopropyl group are preferable.

In R _{2 to} R ₆ , as an example of the alkyl group, a linear or branched alkyl group having 1 to 12 carbon atoms is preferable, and a linear or branched alkyl group having 1 to 4 carbon atoms is more preferable. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n-hexyl group, n-octyl group, 2-ethylhexyl group, etc. And a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a tert-butyl group are preferable.

  As an example of an alkoxyl group, a C1-C6 linear or branched alkoxyl group is preferable, and a C1-C4 linear or branched alkoxyl group is more preferable. Specifically, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutyloxy group, tert-butyloxy group, neopentyloxy group, 2,3-dimethyl-3-pentoxy group, n- A hexyloxy group etc. are mentioned, A methoxy group and an ethoxy group are preferable.

  Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

The alkyl group, alkoxy group in R ₇ to R _11, examples of the halogen atom, R ₂ an alkyl group, an alkoxyl group in to R _6, may be mentioned the same as the halogen atom, preferably group R ₂ to R ₆ It is the same.

  Preferred examples of the azo pigment represented by the general formula (1) include C.I. I. Pigment Red 5, 31, 32, 146, 147, 150, 176, 184, 185, 208, 245, 258, 266, 268, 269, C.I. I. Pigment Violet 32, 50, a compound represented by the chemical formula (3), and an azo pigment composed of the compound represented by the chemical formula (4).

  According to the production method of the present invention, an azo pigment made of a single compound can be produced, or an azo pigment made of two or more different compounds can be produced. The azo pigment serving as the different component is not particularly limited, but the azo pigment serving as the main component and the structure of the base portion or the coupler portion are preferably common.

  Any different raw material for producing the different component can be used as long as it reacts with the diazo component or the coupler component to become an azo compound.

  Examples of the heterogeneous coupler component that reacts with the diazo component to form an azo compound include, in addition to the compound represented by the general formula (5), β-naphthol, 3-hydroxy-2-naphthoic acid, 2-hydroxy-6-sulfone Examples include naphthol derivatives such as acids.

（一般式（５）中、Ｒ₁₂は、水素原子、ベンズイミダゾロン基、アルキルアミノアルキル基、または、一般式（２）で表わされる基を表わす。Ｒ₁₂におけるアルキルアミノアルキル基は、Ｒ₁におけるアルキルアミノアルキル基と同義である。） General formula (5)

(In the general formula (5), R ₁₂ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the general formula (2). The alkylaminoalkyl group in R ₁₂ represents R _1. And is synonymous with the alkylaminoalkyl group in

  Examples of the heterogeneous base component that reacts with the coupler component to become an azo compound include compounds represented by the general formula (6).

（一般式（６）中、Ｒ₁₃〜Ｒ₁₇は、それぞれ独立に、水素原子、アルキル基、アルコキシ基、ハロゲン原子、トリフルオロメチル基、ニトロ基、カルボニル基、スルホン基、カルバモイル基、スルファモイル基、ニトリル基、または、ベンゾイルアミノ基を表す。また、Ｒ₁₃〜Ｒ₁₇は、隣接した基が互いに結合して環を形成しても良い。） General formula (6)

(In the general formula (6), R _{13 to} R ₁₇ are each independently a hydrogen atom, alkyl group, alkoxy group, halogen atom, trifluoromethyl group, nitro group, carbonyl group, sulfone group, carbamoyl group, sulfamoyl group. Represents a nitrile group or a benzoylamino group, and R _{13 to} R ₁₇ may form a ring by bonding adjacent groups to each other.

Here, the alkyl group, alkoxy group, halogen atom, carbamoyl group, and sulfamoyl group in R _{13 to} R ₁₇ in the general formula (6) are the alkyl group, alkoxy group, halogen in R _{2 to} R ₆ in the general formula (1). It is synonymous with an atom, a carbamoyl group, and a sulfamoyl group.

  The order in which the azo pigments as the different components are generated may be any of before, simultaneously with, or after the generation of the azo pigment as the main component. When the azo pigment as the main component and the azo pigment as the dissimilar component are produced at the same time, if the dissimilar base component is used, it is diazotized simultaneously with the main base component. If the dissimilar coupler component is used, the main coupler is used in the coupler tank. It can be carried out by mixing with ingredients and acidifying simultaneously.

  When manufacturing an azo pigment, various additives can be added as needed. The type of additive that can be used is not particularly limited, but it is preferable to add any of surfactants, resins, and pigment derivatives, and it is particularly preferable to add surfactants.

  When an additive is used in producing an azo pigment, the additive may be used in addition to a solution containing a coupler component, a solution containing a diazo component or an acid solution for acid precipitation in advance. It may be used in addition to the slurry. When adding to a solution containing a coupler component, it may be added before the coupler is dissolved, or may be added after acid precipitation.

  As the surfactant, an anionic, nonionic or amphoteric surfactant can be preferably used. When adding a surfactant to a solution containing a coupler component, anionic or amphoteric is preferred. In the case of adding a surfactant to an acid solution for acid precipitation or an acid precipitation coupler slurry, a nonionic surfactant can also be suitably used.

  Anionic surfactants include fatty acid salts, alkyl sulfate esters, alkyl aryl sulfonates, alkyl naphthalene sulfonates, alkyl sulfates, dialkyl sulfonates, dialkyl sulfosuccinates, alkyl diaryl ether disulfonates, alkyls. Phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, naphthalene sulfonic acid formalin condensate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phosphate ester salt, glycerol borate fatty acid Examples include esters and polyoxyethylene glycerol fatty acid esters.

  Examples of amphoteric surfactants include betaine, sulfobetaine, alkylbetaine, and alkylamine oxide.

  Nonionic surfactants include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene oxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester And polyoxyethylene fatty acid ester polyoxyethylene alkylamine.

  These may be used alone or in combination. When combining a surfactant, a surfactant selected from the above can be freely selected, but a combination of an amphoteric surfactant and an anionic surfactant is preferably used. Moreover, you may add in emulsion form using organic solvents, such as xylene. Moreover, these can be used in 0.1-10 weight% with respect to the total weight of a pigment composition, Preferably it is 0.5-5 weight%. When it exceeds 10% by weight, the apparent density of the pigment tends to be low.

  As the resin, known resins can be used and are not particularly limited. Styrene-acrylic acid copolymer, acrylic acid-acrylic acid acrylic ester copolymer, styrene-acrylic acid-acrylic acid alkyl ester copolymer, styrene-methacrylic acid copolymer, styrene-methacrylic acid-acrylic acid acrylic copolymer Polymer, styrene-α-methylstyrene-acrylic acid copolymer, styrene-α-methylstyrene-acrylic acid-acrylic acid alkyl ester copolymer, polyacrylic acid, polymethacrylic acid, vinylnaphthalene-acrylic acid copolymer And salts of styrene-maleic acid copolymer, maleic acid-maleic anhydride copolymer, vinylnaphthalene-maleic acid copolymer, and the like. In preparing these water-soluble resins, those obtained by copolymerization of monomers such as acrylonitrile, vinyl acetate, acrylamide, vinyl chloride, vinylidene chloride, ethylene, and hydroxyethyl acrylate may be used.

  In addition to the above resins, rosin can also be used. As an example of rosin, a known rosin can be used and is not particularly limited. Examples include rosin-modified phenolic resin, disproportionated rosin, hydrogenated rosin, rosin ester and the like. These may be used alone or in combination. These can be used in the range of 0.1 to 50% by weight, preferably 1 to 30% by weight, based on the total weight of the pigment composition.

  Examples of the pigment derivative include compounds represented by the following general formulas (7) to (9).

General formula (7)

P- [X _1- (Y ₁ ) _k ] _m

(In the formula, P represents an organic dye residue.
X ₁ is a direct bond connecting P and Y ₁ , —O—, —S—, —CO—, —SO ₂ —, —NR ₁₈ —, —CONR ₁₈ —, —SO ₂ NR ₁₈ —, —NR _18. CO—, —NR ₁₈ SO ₂ —, a linear or branched alkylene group having 1 to 12 carbon atoms, or an alkyl group, an amino group, a nitro group, a hydroxyl group, an alkoxy group, or a halogen atom. It may be a benzene residue or a triazine residue, or a linking group formed by linking two or more of these linking groups (wherein R ₁₈ represents a hydrogen atom, an alkyl group, or a hydroxyalkyl group).
Y ₁ represents —NR ₁₉ R ₂₀ , —SO ₃ · M / j, or —COO · M / j,
R ₁₉ and R ₂₀ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or R ₁₉ and R ₂₀ together. And represents an optionally substituted heterocyclic group containing a nitrogen, oxygen or sulfur atom, and M represents a hydrogen ion, a 1-3 valent metal ion, or an ammonium ion in which at least one is substituted with an alkyl group. And j represents the valence of M.
k represents an integer of 1 or 2, and m represents an integer of 1 to 4. )

General formula (8)

_{Q- [X 2 - (Y 2} ) k] m

(In the formula, Q represents an anthraquinone residue optionally substituted with an alkyl group, an amino group, a nitro group, a hydroxyl group, an alkoxy group, or a halogen atom.
X ₂ represents a direct bond, —O—, —S—, —CO—, —SO ₂ —, —NR ₁₈ —, —CONR ₁₈ —, —SO ₂ NR ₁₈ —, —NR ₁₈ CO—, —NR _18. SO ₂ —, a linear or branched alkylene group having 1 to 12 carbon atoms, or an alkyl group, an amino group, a nitro group, a hydroxyl group, an alkoxy group, a halogen atom, or a trifluoromethyl group. A benzene residue or a triazine residue, or a linking group formed by linking two or more of these linking groups (wherein R ₁₈ represents a hydrogen atom, an alkyl group, or a hydroxyalkyl group).
Y ₂ represents —NR ₁₉ R ₂₀ , —SO ₃ · M / j, or —COO · M / j,
R ₁₉ and R ₂₀ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or R ₁₉ and R ₂₀ together. And represents an optionally substituted heterocyclic group containing a nitrogen, oxygen or sulfur atom,
M represents a hydrogen ion, a 1-3 valent metal ion, or an ammonium ion at least one of which is substituted with an alkyl group, and j represents the valence of M. k represents an integer of 1 or 2, and m represents an integer of 1 to 4. )

（式中、Ｒは、トリアジン残基を表す。
Ｘ₃からＸ₅は、それぞれ独立に、ＲとＹ₃からＹ₅のいずれかを結ぶ直接結合、−Ｏ−、−Ｓ−、−ＣＯ−、−ＳＯ₂−、−ＮＲ₁₈−、−ＣＯＮＲ₁₈−、−ＳＯ₂ＮＲ₁₈−、−ＮＲ₁₈ＣＯ−、−ＮＲ₁₈ＳＯ₂−、炭素数１〜１２個の直鎖または枝分かれしたアルキレン基、もしくは、アルキル基、アミノ基、ニトロ基、水酸基、アルコキシ基、ハロゲン原子、のいずれかで置換されていてもよいベンゼン残基、または、これら結合基が２個以上連結してなる結合基を表す（ここでＲ₁₈は、水素原子、アルキル基、またはヒドロキシアルキル基を表す）。
Ｙ₃は、−ＮＲ₁₉Ｒ₂₀、−ＳＯ₃・Ｍ／ｊ、または−ＣＯＯ・Ｍ／ｊを表し、Ｒ₁₉とＲ₂₀は、それぞれ独立に、水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基、置換されていてもよいフェニル基、またはＲ₁₉とＲ₂₀とで一体となって窒素、酸素もしくは硫黄原子を含む置換されていてもよい複素環基を表し、
Ｍは、水素イオン、１〜３価の金属イオン、または少なくとも１つがアルキル基で置換されているアンモニウムイオンを表し、ｊはＭの価数を表す。
Ｙ₄とＹ₅は、それぞれ独立に、Ｙ₃と同じであるか、または、アルキル基、アミノ基、ニトロ基、水酸基、アルコキシ基、ハロゲン原子、トリフルオロメチル基、または置換されていてもよいフェニル基のいずれかを表す。
ｐ、ｑ、ｒは、それぞれ独立に、１または２の整数を表す。） General formula (9)

(In the formula, R represents a triazine residue.
X ₃ to X ₅ are each independently a direct bond connecting R and any of Y ₃ to Y ₅ , —O—, —S—, —CO—, —SO ₂ —, —NR ₁₈ —, —CONR. _{18 -, - SO 2 NR 18} -, - NR 18 CO -, - NR 18 SO 2 -, a straight-chain or branched alkylene group having 1 to 12 carbon atoms or an alkyl group, an amino group, a nitro group, a hydroxyl group , A benzene residue optionally substituted with any of an alkoxy group and a halogen atom, or a linking group formed by linking two or more of these linking groups (wherein R ₁₈ represents a hydrogen atom, an alkyl group, Or a hydroxyalkyl group).
Y ₃ represents —NR ₁₉ R ₂₀ , —SO ₃ · M / j, or —COO · M / j, and each of R ₁₉ and R ₂₀ independently represents a hydrogen atom or an optionally substituted alkyl group. , An optionally substituted alkenyl group, an optionally substituted phenyl group, or an optionally substituted heterocyclic group containing a nitrogen, oxygen or sulfur atom together with R ₁₉ and R ₂₀ ; ,
M represents a hydrogen ion, a 1-3 valent metal ion, or an ammonium ion at least one of which is substituted with an alkyl group, and j represents the valence of M.
Y ₄ and Y ₅ are each independently the same as Y ₃ , or may be an alkyl group, amino group, nitro group, hydroxyl group, alkoxy group, halogen atom, trifluoromethyl group, or substituted. It represents one of phenyl groups.
p, q, and r each independently represent an integer of 1 or 2. )

  Here, examples of the organic dye residue in P include diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, and polyazo, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone, and the like. Anthraquinone dyes, quinacridone dyes, dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindoline dyes, isoindolinone dyes, quinophthalone dyes, selenium dyes, porphyrin dyes, phthalocyanine dyes Examples thereof include dyes and metal complex dyes.

Examples of the linear or branched alkylene group having 1 to 12 carbon atoms in X _{1 to} X ₃ include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, and a nonylene group. Group, dexylene group, undecylene group, dodexylene group and isomers thereof.

As the alkyl group which may be substituted in R ₁₉ to R _20, and a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, t- butyl group, a pentyl group, a skeleton, they In which one hydrogen of the above may be substituted with any one of an amino group, a hydroxyl group, chlorine, bromine, a sulfone group, and a nitro group.

Moreover, as an alkenyl group which may be substituted in R _{19 to} R ₂₀ , a vinyl group and a 2-propenyl group are used as a skeleton, and one hydrogen thereof is an amino group, a hydroxyl group, chlorine, bromine, a sulfone group, a nitro group. The thing etc. which may be substituted by any of group are mentioned.

Examples of the optionally substituted phenyl group in R _{19 to} R ₂₀ include a phenyl group, a methylphenyl group, a dimethylphenyl group, a methoxyphenyl group, a nitrophenyl group, a hydroxyphenyl group, a chlorophenyl group, and an aminophenyl group. Can be mentioned.

In addition, the heterocyclic group which may be substituted with R ₁₉ and R ₂₀ and containing a nitrogen, oxygen or sulfur atom includes an azolidine ring, oxolane ring, thiolane ring, azole ring, oxol ring, thiol ring Azinan ring, oxane ring, thiane ring, pyridine ring, lactam ring, pyrazole ring, imidazole ring, oxazole ring, benzimidazolone ring and the like.

  Examples of the 1 to 3 metal ions in M include lithium, sodium, potassium, magnesium, calcium, strontium, barium, aluminum, vanadium, copper, and iron.

  Examples of ammonium ions in which at least one of M is substituted with an alkyl group include dimethylammonium, ethylmethylammonium, diethylammonium, trimethylammonium, triethylammonium, dimethylpropylammonium, diethylpropylammonium and the like.

  These may be used alone or in combination. Moreover, these can be used in 0.1-20 weight% with respect to the total weight of a pigment composition, Preferably it is 1-10 weight%.

  As an example of the general formula (7),

等が挙げられる。

Etc.

等が挙げられる。 As an example of the general formula (8),

Etc.

等が挙げられる。 As an example of the general formula (9),

Etc.

  The above compound can be produced by a method known in the art, for example, a method disclosed in JP 2010-195906 A.

  The azo pigment produced by the production method of the present invention is excellent in easy dispersibility, and has excellent coloring power and sharpness. Therefore, it can be suitably used for printing ink, plastic, textile printing, inkjet ink, electrophotographic printing, color toner, color filter and the like.

  EXAMPLES Hereinafter, although the manufacturing method of this invention is demonstrated by an Example, this invention is not limited to these. In Examples and Comparative Examples, “part” represents “part by mass” unless otherwise specified.

(Example 1) Production method of pigment A As a base component, 24.2 parts of 3-amino-4-methoxybenzanilide was added to 432.2 parts of water and stirred to prepare a suspension, and ice was further added. The temperature was adjusted to 5 ° C. 39.7 parts of 35% -hydrochloric acid was added thereto, and stirred for 1 hour. Thereafter, 7.1 parts of sodium nitrite was added to 22 parts of water, a prepared aqueous solution was added, and diazotization was performed by stirring for 1 hour. 2 parts of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a solution containing a diazo component was obtained.

Moreover, 51.6 parts of 80% -acetic acid aqueous solution, 335 parts of water, and 670 parts of ice were put into the coupling tank and stirred to obtain an aqueous acetic acid solution.

On the other hand, while 670 parts of water and 99.9 parts of 25% -aqueous sodium hydroxide solution were mixed and heated to 90 ° C., N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2 was used as a coupler component. -33.4 parts of naphthamide was added and dissolved for 10 minutes to obtain a solution containing a coupler component. This solution was introduced into a coupling tank in which an aqueous acetic acid solution was stirred over 30 minutes to perform acid precipitation. When all the ice melted during acid precipitation, 400 parts of ice was added. After the introduction of the solution containing the coupler component was completed, this solution was heated to 15 ° C. Furthermore, 38.0 parts of 35% hydrochloric acid was added to obtain an acid precipitation coupler slurry.

While stirring the acid precipitation coupler slurry, the solution containing the diazo component was added over 20 minutes. After the introduction of the solution containing the diazo component, the reaction was completed by further stirring for 8 hours. After completion of the reaction, the slurry was heated to 80 ° C., filtered, and washed with water to obtain a press cake of the pigment composition. The press cake was dried at 90 ° C. for 18 hours, and then pulverized using a hammer mill equipped with a mesh having a 1 mm mesh to obtain 56.7 parts of pigment A.

(Example 2) Production method of pigment composition B As a base component, 24.2 parts of 3-amino-4-methoxybenzanilide was added to 432.2 parts of water and stirred to prepare a suspension. In addition, the temperature was adjusted to 5 ° C. 39.7 parts of 35% -hydrochloric acid was added thereto, and stirred for 1 hour. Thereafter, 7.1 parts of sodium nitrite was added to 22 parts of water, a prepared aqueous solution was added, and diazotization was performed by stirring for 1 hour. 2 parts of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a solution containing a diazo component was obtained.

Further, 34.4 parts of an 80% aqueous acetic acid solution, 335 parts of water and 670 parts of ice were placed in a coupling tank and stirred to obtain an aqueous acetic acid solution.

On the other hand, 670 parts of water, 3.3 parts of 70% polyoxyethylene alkyl ether potassium phosphate (manufactured by Kao Corporation: Electrostripper F) and 66.6 parts of 25% -sodium hydroxide aqueous solution are mixed and heated to 80 ° C. Then, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was added as a coupler component and dissolved over 10 minutes to obtain a solution containing the coupler component. This solution was introduced into a coupling tank in which an aqueous acetic acid solution was stirred over 30 minutes to perform acid precipitation. When all the ice melted during acid precipitation, 400 parts of ice was added. After the introduction of the solution containing the coupler component was completed, this solution was heated to 15 ° C. Furthermore, 29.0 parts of 35% -hydrochloric acid was added to obtain an acid precipitation coupler slurry.

While stirring the acid precipitation coupler slurry, the solution containing the diazo component was added over 20 minutes. After the introduction of the solution containing the diazo component, the reaction was completed by further stirring for 8 hours. After completion of the reaction, the slurry was heated to 80 ° C., filtered, and washed with water to obtain a press cake of the pigment composition. The press cake was dried at 90 ° C. for 18 hours, and then pulverized using a hammer mill equipped with a mesh having a 1 mm mesh to obtain 58.7 parts of pigment composition B.

(Example 3) Production method of pigment composition C 70% Similar to Example 2, except that 2.3 parts of sodium dodecylbenzenesulfonate was added instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate Thus, 58.6 parts of pigment composition C were obtained.

(Example 4) Production method of pigment composition D Example 70, except that 2.3 parts of sodium di-2-ethylhexylsulfosuccinate is added instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate In the same manner as in No. 2, 59.0 parts of pigment composition D was obtained.

(Example 5) Manufacturing method of pigment composition E 70% The same method as in Example 2 except that 2.3 parts of sodium lauryl sulfate is added instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate. Thus, 58.7 parts of pigment composition E was obtained.

(Example 6) Production method of pigment composition F 70% The same method as in Example 2 except that 2.3 parts of dimethyldodecylbetaine is added instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate Thus, 59.2 parts of pigment composition F was obtained.

(Example 7) Production method of pigment composition G 70% Polyoxyethylene alkyl ether Instead of 3.3 parts of potassium phosphate, 8.8 parts of 26% alkyldimethylbetaine (manufactured by Kao Corporation: Amphitol 86B) are added. Except for this, 58.9 parts of pigment composition G were obtained in the same manner as in Example 2.

(Example 8) Production method of pigment composition H Pigment composition in the same manner as in Example 1, except that 0.6 part of polyoxyethylene lauryl ether (manufactured by Kao Corporation: Emulgen 105) was added to the aqueous acetic acid solution. 57.8 parts of product H were obtained.

(Example 9) Production method of pigment composition I As a base component, 24.2 parts of 3-amino-4-methoxybenzanilide was added to 432.2 parts of water and stirred to prepare a suspension. In addition, the temperature was adjusted to 5 ° C. 39.7 parts of 35% -hydrochloric acid was added thereto, and stirred for 1 hour. Thereafter, 7.1 parts of sodium nitrite was added to 22 parts of water, an aqueous solution prepared was added, and the mixture was stirred for 1 hour for diazotization. 2 parts of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a solution containing a diazo component was obtained.

Further, 34.4 parts of an 80% aqueous acetic acid solution, 335 parts of water and 670 parts of ice were placed in a coupling tank and stirred to obtain an aqueous acetic acid solution.

On the other hand, 670 parts of water, 2.3 parts of dimethyldodecylbetaine, and 66.6 parts of 25% -aqueous sodium hydroxide solution were mixed, and N- (5-chloro-2-methoxyphenyl) -3-hydroxy was used as a coupler component. 2-Naphthoamide (33.4 parts) was mixed to obtain a suspension containing a coupler component at 25 ° C. During the transfer of the suspension containing this coupler component, steam was blown from a steam mixer attached in the flow path and heated to 85 ° C., and the acetic acid aqueous solution was introduced into a coupling tank for stirring, and acid deposition was performed. . The flow rate was adjusted so that the time from when the suspension containing the coupler component was mixed with the steam until it was introduced into the coupling tank was 0.5 minutes. When all the ice melted during acid precipitation, 400 parts of ice was added. After the introduction of the solution containing the coupler component was completed, this solution was heated to 15 ° C. Furthermore, 29.0 parts of 35% -hydrochloric acid was added to obtain an acid precipitation coupler slurry.

While stirring the acid precipitation coupler slurry, the solution containing the diazo component was added over 20 minutes. After the introduction of the solution containing the diazo component, the reaction was completed by further stirring for 8 hours. After completion of the reaction, the slurry was heated to 80 ° C., filtered, and washed with water to obtain a press cake of the pigment composition. The press cake was dried at 90 ° C. for 18 hours, and then pulverized using a hammer mill equipped with a mesh having a 1 mm mesh to obtain 56.9 parts of pigment composition I.

(Example 106) Production method of pigment composition DB 70% Instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate, 0.2 part of dimethyldodecylbetaine and 2.1 parts of sodium dodecylbenzenesulfonate are added. Except for the above, 58.2 parts of pigment composition DB was obtained in the same manner as in Example 2.

(Example 107) Manufacturing method of pigment composition DC 70% Instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate, 0.6 parts of dimethyl dodecyl betaine and 1.7 parts of sodium dodecylbenzenesulfonate are added. Except for the above, 58.0 parts of pigment composition DC was obtained in the same manner as in Example 2.

(Example 108) 70% of the manufacturing method of pigment composition DD Instead of adding 3.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate, 0.2 part of dimethyldodecylbetaine and 3.5 parts of Taca Power BN2060 are added. In the same manner as in Example 2, 58.6 parts of pigment composition DD was obtained.

(Example 109) Production method of pigment composition DE 70% Instead of adding 3.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate, except adding 0.6 parts of dimethyldodecylbetaine and 2.9 parts of Taca Power BN2060 In the same manner as in Example 2, 58.1 parts of pigment composition DE was obtained.

(Example 110) 70% of the manufacturing method of pigment composition DF The same method as Example 2 except adding 3.9 parts of Taca Power BN2060 instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate Thus, 58.7 parts of pigment composition DF was obtained.

(Example 111) Production method of pigment composition DG 70% Polyoxyethylene alkyl ether Instead of 3.3 parts of potassium phosphate, 0.2 part of dimethyldodecylbetaine and 2.1 parts of sodium di-2-ethylhexyl sulfosuccinate 58.7 parts of pigment composition DG was obtained in the same manner as in Example 2 except that was added.

(Example 112) Production method of pigment composition DH 70% 0.6 parts of dimethyl dodecyl betaine and 1.7 parts of sodium di-2-ethylhexyl sulfosuccinate instead of 3.3 parts of potassium polyoxyethylene alkyl ether phosphate 58.1 parts of pigment composition DH was obtained in the same manner as in Example 2, except that

(Example 113) Production method of pigment composition DI 70% Polyoxyethylene alkyl ether Instead of 3.3 parts of potassium phosphate, 0.9 part of 26% alkyl dimethyl betaine (Ao Hitor 86B manufactured by Kao Corporation) and dodecyl 58.1 parts of pigment composition DI was obtained in the same manner as in Example 2, except that 2.1 parts of sodium benzenesulfonate was added.

(Example 114) Production method of pigment composition DJ 70% Polyoxyethylene alkyl ether Instead of 3.3 parts of potassium phosphate, 2.7 parts of 26% alkyldimethylbetaine (Aohitoru 86B, manufactured by Kao Corporation) and dodecyl Except for adding 1.7 parts of sodium benzenesulfonate, 58.1 parts of pigment composition DJ was obtained in the same manner as in Example 2.

(Example 115) Manufacturing method of pigment composition DK 70% Polyoxyethylene alkyl ether Instead of 3.3 parts of potassium phosphate, 0.9 part of 26% alkyldimethylbetaine (manufactured by Kao Corporation: Amphitol 86B) and Taca 58.1 parts of pigment composition DK were obtained in the same manner as in Example 2 except that 3.5 parts of Power BN2060 was added.

Example 116 Production Method of Pigment Composition DL 70% Polyoxyethylene alkyl ether In place of 3.3 parts of potassium phosphate, 2.7 parts of 26% alkyldimethylbetaine (Kao Co., Ltd .: Anhitole 86B) and Taca 58.1 parts of pigment composition DL was obtained in the same manner as in Example 2 except that 2.9 parts of power BN2060 was added.

Example 117 Production Method of Pigment Composition DM 70% Polyoxyethylene alkyl ether instead of 3.3 parts of potassium phosphate, 0.9 part of 26% alkyldimethylbetaine (Aohito 86B, manufactured by Kao Corporation) 58.1 parts of pigment composition DM were obtained in the same manner as in Example 2, except that 2.1 parts of sodium 2-ethylhexyl sulfosuccinate was added.

Example 118 Production Method of Pigment Composition DN 70% Polyoxyethylene alkyl ether Instead of 3.3 parts of potassium phosphate, 2.7 parts of 26% alkyldimethylbetaine (Kao Corporation: Anhitol 86B) 58.1 parts of pigment composition DN were obtained in the same manner as in Example 2 except that 1.7 parts of sodium 2-ethylhexyl sulfosuccinate was added.

(Example 132) Production method of pigment EB Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, 1005 parts of hot water adjusted to 40 ° C. is used as an aqueous acetic acid solution, and the temperature during introduction of the solution containing the coupler component in the aqueous acetic acid solution is appropriately maintained within the range of 40 to 45 ° C. by adding ice. Except for this, 55.3 parts of pigment EB was obtained in the same manner as in Example 1.

(Example 133) Production method of pigment composition EC Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.6 parts of pigment composition EC was obtained in the same manner as in Example 2.

(Example 134) Manufacturing method of pigment composition ED Instead of obtaining 51.6 parts of 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 was obtained instead of obtaining an acetic acid aqueous solution. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. 58.2 parts of pigment composition ED was obtained in the same manner as in Example 3 except for maintaining.

Example 135 Method for Producing Pigment Composition EE Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.7 parts of pigment composition EE were obtained in the same manner as in Example 4.

(Example 136) Production method of pigment composition EF Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.7 parts of pigment composition EF was obtained in the same manner as in Example 5.

(Example 137) Production method of pigment composition EG Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.4 parts of pigment composition EG was obtained in the same manner as in Example 6.

(Example 138) Production method of pigment composition EH Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.4 parts of pigment composition EH were obtained in the same manner as in Example 7.

(Example 139) Production method of pigment composition EI Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.3 parts of pigment composition EI was obtained in the same manner as in Example 9.

(Example 140) Manufacturing method of pigment composition EJ Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, 51.6 parts of an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.0 parts of pigment composition EJ was obtained in the same manner as in Example 106.

(Example 141) Production method of pigment composition EK Instead of obtaining an acetic acid aqueous solution by placing 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.4 parts of pigment composition EK was obtained in the same manner as in Example 107.

(Example 142) Production method of pigment composition EL Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.8 parts of pigment composition EL was obtained in the same manner as in Example 108.

(Example 143) Manufacturing method of pigment composition EM Instead of obtaining an acetic acid aqueous solution by placing 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 58.7 parts of pigment composition EM was obtained in the same manner as in Example 109.

(Example 144) Production method of pigment composition EN Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.9 parts of pigment composition EN was obtained in the same manner as in Example 110.

Example 145 Method for Producing Pigment Composition EO Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 is obtained. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.4 parts of pigment composition EO was obtained in the same manner as in Example 111.

(Example 146) Production method of pigment composition EP Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.7 parts of pigment composition EP was obtained in the same manner as in Example 112.

(Example 147) Production method of pigment composition EQ Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.7 parts of pigment composition EQ was obtained in the same manner as in Example 113.

Example 148 Method for Producing Pigment Composition ER Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.8 parts of pigment composition ER was obtained in the same manner as in Example 114.

(Example 149) Production method of pigment composition ES Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.7 parts of pigment composition ES was obtained in the same manner as in Example 115.

Example 150 Method for Producing Pigment Composition ET Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% aqueous acetic acid solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.8 parts of pigment composition ET was obtained in the same manner as in Example 116.

Example 151 Method for Producing Pigment Composition EU Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.7 parts of pigment composition EU was obtained in the same manner as in Example 117.

(Example 152) Production method of pigment composition EV Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.9 parts of pigment composition EV was obtained in the same manner as in Example 118.

(Example 10) Production method of pigment composition J After diazotization, 2.9 parts of compound (1) was added to a solution containing a diazo component, and after stirring for 8 hours, the pH was adjusted with an aqueous sodium hydroxide solution. 59.5 parts of pigment composition J was obtained in the same manner as in Example 1, except that the amount of pigment composition J was adjusted to 7.

(Example 11) Production method of pigment composition K Pigment composition K 58. In the same manner as in Example 1, except that 2.9 parts of compound (2) was added during the preparation of the solution containing the coupler component. 8 parts were obtained.

(Example 12) Manufacturing method of pigment composition L After adding 2.9 parts of compound (3) to a solution containing a diazo component after diazotization and stirring for 8 hours after coupling, pH was adjusted with an aqueous sodium hydroxide solution. 58.7 parts of Pigment Composition L was obtained in the same manner as in Example 1 except that the value was adjusted to 7.

(Example 13) Production method of pigment composition M Pigment composition M 58. In the same manner as in Example 1, except that 2.9 parts of compound (4) was added during the preparation of the solution containing the coupler component. 9 parts were obtained.

(Example 14) Production method of pigment composition N After diazotization, 2.9 parts of compound (5) was added to the solution containing the diazo component, and after stirring for 8 hours, the pH was adjusted with an aqueous sodium hydroxide solution. 59.2 parts of pigment composition N was obtained in the same manner as in Example 1 except that the value of was adjusted to 7.

(Example 15) Production method of pigment composition O Pigment composition O 59. was prepared in the same manner as in Example 1 except that 2.9 parts of compound (6) was added during the preparation of the solution containing the coupler component. Two parts were obtained.

(Example 16) Production method of pigment composition P To a slurry after stirring for 8 hours after coupling, 2.9 parts of compound (7) dissolved in hydrochloric acid was added, and then the pH was adjusted with an aqueous sodium hydroxide solution. Except for adjusting to 7, 59.6 parts of pigment composition P was obtained in the same manner as in Example 1.

(Example 17) Production method of pigment composition Q To a slurry after stirring for 8 hours after coupling, 2.9 parts of compound (8) dissolved in hydrochloric acid was added, and then the pH was adjusted with an aqueous sodium hydroxide solution. 59.8 parts of pigment composition Q was obtained in the same manner as in Example 1, except that the value of was adjusted to 7.

Example 18 Production Method of Pigment R Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro-2 Pigment R 56 in the same manner as in Example 1 except that a mixture of 32.4 parts of (methoxyphenyl) -3-hydroxy-2-naphthamide and 0.6 part of 3-hydroxy-2-naphthalenecarboxamide was used. .5 parts were obtained.

Example 19 Production Method of Pigment Composition S Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro In the same manner as in Example 2, except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 0.6 parts of 3-hydroxy-2-naphthalenecarboxamide was used, 57.7 parts of composition S were obtained.

(Example 20) Production method of pigment composition T Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro In the same manner as in Example 6, except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 0.6 parts of 3-hydroxy-2-naphthalenecarboxamide was used, 57.8 parts of composition T were obtained.

Example 21 Production Method of Pigment Composition U Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro In the same manner as in Example 9, except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 0.6 parts of 3-hydroxy-2-naphthalenecarboxamide was used, 58.0 parts of Composition U were obtained.

(Example 119) Production method of pigment composition DO Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 106 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 58.7 parts of composition DO were obtained.

(Example 120) Production method of pigment composition DP Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro In the same manner as in Example 107 except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.5 parts of 3-hydroxy-2-naphthalenecarboxamide was used, 57.7 parts of composition DP were obtained.

(Example 121) Production method of pigment composition DQ Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-Methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 108 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 56.5 parts of composition DQ were obtained.

(Example 122) Production method of pigment composition DR Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-Methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 109 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 56.9 parts of composition DR were obtained.

(Example 123) Production method of pigment composition DS Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro In the same manner as in Example 110 except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.5 parts of 3-hydroxy-2-naphthalenecarboxamide was used, the pigment 57.7 parts of composition DS were obtained.

(Example 124) Production method of pigment composition DT Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 111 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 57.0 parts of composition DT were obtained.

(Example 125) Production method of pigment composition DU Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 112 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 56.5 parts of composition DU were obtained.

(Example 126) Production method of pigment composition DV Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 113 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 58.1 parts of composition DV were obtained.

(Example 127) Production method of pigment composition DW Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 114 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 56.6 parts of composition DW were obtained.

(Example 128) Production method of pigment composition DX Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro In the same manner as in Example 115 except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.5 parts of 3-hydroxy-2-naphthalenecarboxamide was used, 57.1 parts of composition DX were obtained.

(Example 129) Production method of pigment composition DY Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 116 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 57.0 parts of composition DY were obtained.

(Example 130) Production method of pigment composition DZ Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 117 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 56.7 parts of composition DZ were obtained.

(Example 131) Production method of pigment composition EA Instead of using 30.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-Methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Example 118 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 58.3 parts of composition EA were obtained.

Example 153 Method for Producing Pigment Composition EW Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.2 parts of pigment composition EW was obtained in the same manner as in Example 20.

(Example 154) Production Method of Pigment Composition EX Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.5 parts of pigment composition EX was obtained in the same manner as in Example 119.

Example 155 Method for Producing Pigment Composition EY Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 is obtained. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.8 parts of pigment composition EY were obtained in the same manner as in Example 120.

(Example 156) Production method of pigment composition EZ Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.5 parts of pigment composition EZ was obtained in the same manner as in Example 121.

(Example 157) Production method of pigment composition FA Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.5 parts of pigment composition FA was obtained in the same manner as in Example 122.

(Example 158) Production Method of Pigment Composition FB Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 is obtained. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 58.6 parts of pigment composition FB was obtained in the same manner as in Example 123.

(Example 159) Production method of pigment composition FC Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.8 parts of pigment composition FC was obtained in the same manner as in Example 124.

(Example 160) Production method of pigment composition FD Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.5 parts of pigment composition FD was obtained in the same manner as in Example 125.

Example 161 Production Method of Pigment Composition FE Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 was obtained. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 58.1 parts of pigment composition FE was obtained in the same manner as in Example 126.

(Example 162) Production method of pigment composition FF Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.8 parts of pigment composition FF was obtained in the same manner as in Example 127.

(Example 163) Production method of pigment composition FG Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.4 parts of pigment composition FG was obtained in the same manner as in Example 128.

(Example 164) Production method of pigment composition FH Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.8 parts of pigment composition FH was obtained in the same manner as in Example 129.

(Example 165) Production method of pigment composition FI Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 58.1 parts of pigment composition FI was obtained in the same manner as in Example 130.

(Example 166) Production Method of Pigment Composition FJ Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.9 parts of pigment composition FJ was obtained in the same manner as in Example 131.

Example 22 Production Method of Pigment V Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro-2 Except for using a mixture of 31.8 parts of -methoxyphenyl) -3-hydroxy-2-naphthamide and 1.6 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide. In the same manner as in Example 1, 56.3 parts of Pigment V was obtained.

Example 23 Production Method of Pigment Composition W Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro Except that a mixture of 31.8 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.6 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide is used. In the same manner as in Example 2, 58.8 parts of pigment composition W was obtained.

(Example 24) Production method of pigment composition X Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro Except that a mixture of 31.8 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.6 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide is used. In the same manner as in Example 6, 58.7 parts of pigment composition X was obtained.

Example 25 Production Method of Pigment Composition Y Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro Except that a mixture of 31.8 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.6 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide is used. In the same manner as in Example 9, 58.3 parts of pigment composition Y was obtained.

(Example 167) Manufacturing method of pigment composition FK Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.3 parts of pigment composition FK was obtained in the same manner as in Example 24.

(Example 26) Manufacturing method of pigment composition Z Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide 32.4 parts and N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide, except that a mixture of 0.9 parts was used. In the same manner as in Example 1, 56.7 parts of pigment composition Z was obtained.

Example 27 Production Method of Pigment Composition AA Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide 32.4 parts and N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide, except that a mixture of 0.9 parts was used. In the same manner as in Example 2, 59.1 parts of pigment composition AA were obtained.

(Example 28) Production method of pigment composition AB Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide 32.4 parts and N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide, except that a mixture of 0.9 parts was used. In the same manner as in Example 6, 58.6 parts of pigment composition AB was obtained.

Example 29 Production Method of Pigment Composition AC Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide 32.4 parts and N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide, except that a mixture of 0.9 parts was used. In the same manner as in Example 9, 58.1 parts of pigment composition AC was obtained.

(Example 168) Production method of pigment composition FL Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% aqueous acetic acid solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous 80% acetic acid solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 58.7 parts of pigment composition FL was obtained in the same manner as in Example 28.

Example 30 Method for Producing Pigment AD Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 25.8 N, N-diethyl-3-amino-4-methoxybenzenesulfonamide Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2,4-dimethoxy-5-chlorophenyl)- 61.2 parts of pigment AD was obtained in the same manner as in Example 1 except that 36.5 parts of 3-hydroxy-2-naphthamide was used.

Example 31 Production Method of Pigment Composition AE Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N, N-diethyl-3-amino-4-methoxybenzenesulfonamide 25 8 parts, and instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2,4-dimethoxy-5-chlorophenyl) ) 63.5 parts of pigment composition AE were obtained in the same manner as in Example 2 except that 36.5 parts of 3-hydroxy-2-naphthamide were used.

(Example 32) Production method of pigment composition AF Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, N, N-diethyl-3-amino-4-methoxybenzenesulfonamide 25 8 parts, and instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2,4-dimethoxy-5-chlorophenyl) ) 63.3 parts of pigment composition AF was obtained in the same manner as in Example 6 except that 36.5 parts of -3-hydroxy-2-naphthamide was used.

(Example 33) Production method of pigment composition AG Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, N, N-diethyl-3-amino-4-methoxybenzenesulfonamide 25 8 parts, and instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2,4-dimethoxy-5-chlorophenyl) ) 65.0 parts of pigment composition AG were obtained in the same manner as in Example 9, except that 36.5 parts of 3-hydroxy-2-naphthamide were used.

(Example 169) Production method of pigment composition FM Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 61.5 parts of pigment composition FM was obtained in the same manner as in Example 32.

(Example 34) Production method of pigment AH Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 54.7 parts of pigment AH was obtained in the same manner as in Example 1, except that 31.8 parts of -chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 35) Production method of pigment composition AI Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 57.1 parts of pigment composition AI were obtained in the same manner as in Example 2 except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 36) Manufacturing method of pigment composition AJ Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 57.5 parts of pigment composition AJ was obtained in the same manner as in Example 6 except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 37) Production method of pigment composition AK Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 59.5 parts of pigment composition AK were obtained in the same manner as in Example 9, except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 170) Manufacturing method of pigment composition FN Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.8 parts of pigment composition FN was obtained in the same manner as in Example 36.

Example 38 Production Method of Pigment AL Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3-hydroxy- 49.9 parts of pigment AL was obtained in the same manner as in Example 1, except that 26.9 parts of 2-naphthamide were used.

(Example 39) Production method of pigment composition AM Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3- Pigment composition AM 51.9 parts was obtained by the same method as Example 2 except using 26.9 parts of hydroxy-2-naphthamide.

(Example 40) Production method of pigment composition AN Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3- 51.9 parts of pigment composition AN was obtained in the same manner as in Example 6 except that 26.9 parts of hydroxy-2-naphthamide was used.

(Example 41) Production method of pigment composition AO Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3- 52.5 parts of pigment composition AO was obtained in the same manner as in Example 9, except that 26.9 parts of hydroxy-2-naphthamide was used.

(Example 171) Production method of pigment composition FO Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 50.7 parts of pigment composition FO was obtained in the same manner as in Example 40.

(Example 42) Production method of pigment AP Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (4-chloro-2 , 5-dimethoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 1, except that 36.5 parts were used, 59.9 parts of pigment AP was obtained.

(Example 43) Production method of pigment composition AQ Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (4-chloro 61.9 parts of pigment composition AQ were obtained in the same manner as in Example 2, except that 36.5 parts of -2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide was used.

(Example 44) Production method of pigment composition AR Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (4-chloro 62.2 parts of pigment composition AR was obtained in the same manner as in Example 6 except that 36.5 parts of -2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide was used.

Example 45 Production Method of Pigment Composition AS Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (4-chloro 61.7 parts of pigment composition AS was obtained in the same manner as in Example 9, except that 36.5 parts of -2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide was used.

(Example 172) Production method of pigment composition FP Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 60.0 parts of pigment composition FP was obtained in the same manner as in Example 44.

Example 46 Production Method of Pigment AT Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 54.9 parts of pigment AT were obtained in the same manner as in Example 1, except that 31.8 parts of -chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 47) Production method of pigment composition AU Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 57.3 parts of pigment composition AU were obtained in the same manner as in Example 2, except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

Example 48 Production Method of Pigment Composition AV Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 56.5 parts of pigment composition AV was obtained in the same manner as in Example 6 except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

Example 49 Production Method of Pigment Composition AW Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 57.4 parts of pigment composition AW were obtained in the same manner as in Example 9, except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 173) Production method of pigment composition FQ Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 56.2 parts of pigment composition FQ was obtained in the same manner as in Example 48.

Example 50 Production Method of Pigment AX Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, 3-hydroxy-2-naphthalenecarbo Pigment AX 49 in the same manner as in Example 1 except that a mixture of 9.6 parts of amide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide is used. .4 parts were obtained.

Example 51 Production Method of Pigment Composition AY Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, 3-hydroxy-2- In the same manner as in Example 2 except that a mixture of 9.6 parts of naphthalenecarboxamide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide is used, the pigment 52.0 parts of composition AY was obtained.

(Example 52) Production method of pigment composition AZ Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, 3-hydroxy-2- In the same manner as in Example 6 except that a mixture of 9.6 parts of naphthalenecarboxamide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was used, the pigment 51.8 parts of composition AZ were obtained.

(Example 53) Production method of pigment composition BA Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, 3-hydroxy-2- In the same manner as in Example 9, except that a mixture of 9.6 parts of naphthalenecarboxamide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was used, the pigment 52.1 parts of composition BA were obtained.

(Example 174) Production method of pigment composition FR Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 52.1 parts of pigment composition FR was obtained in the same manner as in Example 52.

(Example 54) Production method of pigment BB Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-[(2,3- Dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide, except for using 32.6 parts, pigment BB 56.0 in the same manner as in Example 1. Got a part.

(Example 55) Production method of pigment composition BC Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-[(2, 3-Dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide, except that 32.6 parts were used, in the same manner as in Example 2, the pigment composition 57.6 parts of BC were obtained.

(Example 56) Production method of pigment composition BD Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-[(2, 3-Dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide in the same manner as in Example 6 except that 32.6 parts were used. 57.9 parts of BD were obtained.

(Example 57) Production method of pigment composition BE Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-[(2, 3-Dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide in the same manner as in Example 9, except that 32.6 parts are used. 58.0 parts of BE were obtained.

(Example 175) Production method of pigment composition FS Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.9 parts of pigment composition FS was obtained in the same manner as in Example 56.

Example 58 Production Method of Pigment BF Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 -Chlorophenyl) -3-hydroxy-2-naphthamide 15.9 parts and N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide 18.3 parts In the same manner as in Example 1, 57.6 parts of pigment BF was obtained.

(Example 59) Production method of pigment composition BG Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl Other than using a mixture of 15.9 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 2, 60.0 parts of pigment composition BG was obtained.

(Example 60) Manufacturing method of pigment composition BH Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl Other than using a mixture of 15.9 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 6, 58.8 parts of pigment composition BH was obtained.

Example 61 Production Method of Pigment Composition BI Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl Other than using a mixture of 15.9 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 9, 59.5 parts of pigment composition BI was obtained.

(Example 176) Method for Producing Pigment Composition FT Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 59.4 parts of pigment composition FT were obtained in the same manner as in Example 60.

Example 62 Production Method of Pigment BJ Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 23.0 , And instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2-oxo- 1H-Benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 54.4 parts of pigment BJ was obtained in the same manner as in Example 1 except that 32.6 parts were used.

Example 63 Production Method of Pigment Composition BK Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 23 Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 32.6 parts of pigment composition BK was prepared in the same manner as in Example 2 except that 32.6 parts were used. Obtained.

(Example 64) Production method of pigment composition BL Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 23 Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 32.6 parts of pigment composition BL were prepared in the same manner as in Example 6 except that 32.6 parts were used. Obtained.

Example 65 Production Method of Pigment Composition BM Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 23 Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide, except that 32.6 parts were used, in the same manner as in Example 9 except that 57.1 parts of pigment composition BM were added. Obtained.

(Example 177) Method for Producing Pigment Composition FU Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. A pigment composition FU of 55.6 parts was obtained in the same manner as in Example 64 except for maintaining.

Example 66 Production Method of Pigment BN Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 19.3 parts of butyl 2-aminobenzoate was used, and N- ( Instead of using 33.4 parts of 5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] 50.3 parts of pigment BN was obtained in the same manner as in Example 1 except that 32.6 parts of -3-hydroxy-2-naphthalenecarboxamide was used.

Example 67 Production Method of Pigment Composition BO Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 19.3 parts of butyl 2-aminobenzoate were used and N as the coupler component Instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5- In the same manner as in Example 2, except that 32.6 parts of [Il] -3-hydroxy-2-naphthalenecarboxamide was used, 53.4 parts of pigment composition BO was obtained.

Example 68 Production Method of Pigment Composition BP Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 19.3 parts of butyl 2-aminobenzoate were used and N as the coupler component Instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5- In the same manner as in Example 6, except that 32.6 parts of [Il] -3-hydroxy-2-naphthalenecarboxamide was used, 53.6 parts of pigment composition BP was obtained.

Example 69 Production Method for Pigment Composition BQ Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 19.3 parts of butyl 2-aminobenzoate were used and N as the coupler component Instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5- In the same manner as in Example 9, except for using 32.6 parts of [Il] -3-hydroxy-2-naphthalenecarboxamide, 52.6 parts of pigment composition BQ were obtained.

(Example 178) Manufacturing method of pigment composition FV Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. 51.7 parts of pigment composition FV was obtained in the same manner as in Example 68 except for maintaining.

Example 70 Production Method of Pigment BR Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 11.6 parts of 3-amino-4-methoxybenzamide was used, and N was used as the coupler component. Instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, it was carried out except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide were used. In the same manner as in Example 1, 50.8 parts of pigment BR was obtained.

(Example 71) Production method of pigment composition BS Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 11.6 parts of 3-amino-4-methoxybenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Example 2, 52.7 parts of pigment composition BS was obtained.

Example 72 Production Method of Pigment Composition BT Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 11.6 parts of 3-amino-4-methoxybenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Example 6, 53.1 parts of pigment composition BT was obtained.

(Example 73) Production method of pigment composition BU Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 11.6 parts of 3-amino-4-methoxybenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Example 9, 52.6 parts of pigment composition BU was obtained.

(Example 179) Production method of pigment composition FW Into a coupling tank, 51.6 parts of 80% -acetic acid aqueous solution, 335 parts of water, and 670 parts of ice were added to obtain an acetic acid aqueous solution. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 52.4 parts of pigment composition FW was obtained in the same manner as in Example 72.

Example 74 Production Method of Pigment BV Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline was used as a coupler component. Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide are used, In the same manner as in Example 1, 53.5 parts of pigment BV was obtained.

Example 75 Production Method of Pigment Composition BW Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline were used as a coupler. Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a component, except using 26.9 parts N-phenyl-3-hydroxy-2-naphthamide Obtained 55.1 parts of pigment composition BW in the same manner as in Example 2.

Example 76 Production Method of Pigment Composition BX Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline were used as a coupler. Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a component, except using 26.9 parts N-phenyl-3-hydroxy-2-naphthamide In the same manner as in Example 6, 55.1 parts of pigment composition BX was obtained.

Example 77 Production Method of Pigment Composition BY Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline were used as a coupler. Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a component, except using 26.9 parts N-phenyl-3-hydroxy-2-naphthamide In the same manner as in Example 9, 55.2 parts of pigment composition BY was obtained.

(Example 180) Production method of pigment composition FX Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. A pigment composition FX of 55.2 parts was obtained in the same manner as in Example 76 except for maintaining.

Example 78 Production Method of Pigment BZ Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 13.6 parts of p-aminobenzamide was used, and N- (5- Chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide Instead of using 33.4 parts N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide other than 29.9 parts In the same manner as in Example 1, 42.7 parts of pigment BZ was obtained.

Example 79 Production Method of Pigment Composition CA Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 13.6 parts of p-aminobenzamide was used, and N- ( Instead of using 33.4 parts of 5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide are used. Except for this, 44.8 parts of pigment composition CA were obtained in the same manner as in Example 2.

Example 80 Production Method of Pigment Composition CB Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 13.6 parts of p-aminobenzamide was used, and N- ( Instead of using 33.4 parts of 5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide are used. Except for this, 45.4 parts of pigment composition CB were obtained in the same manner as in Example 6.

(Example 81) Production method of pigment composition CC Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 13.6 parts of p-aminobenzamide was used, and N- ( Instead of using 33.4 parts of 5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide are used. Except for this, 44.5 parts of pigment composition CC was obtained in the same manner as in Example 9.

(Example 181) Production method of pigment composition FY Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 44.1 parts of pigment composition FY was obtained in the same manner as in Example 80.

Example 82 Production Method of Pigment CD Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 15.0 parts of 3-amino-4-methylbenzamide was used, and N was used as the coupler component. Instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, it was carried out except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide were used. In the same manner as in Example 1, 40.8 parts of pigment CD was obtained.

Example 83 Production Method of Pigment Composition CE Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 15.0 parts of 3-amino-4-methylbenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Example 2, 43.2 parts of pigment composition CE was obtained.

(Example 84) Production method of pigment composition CF Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 15.0 parts of 3-amino-4-methylbenzamide was used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Example 6, 43.2 parts of pigment composition CF was obtained.

Example 85 Production Method of Pigment Composition CG Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 15.0 parts of 3-amino-4-methylbenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Example 9, 43.3 parts of pigment composition CG was obtained.

(Example 182) Production method of pigment composition FZ Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 43.4 parts of pigment composition FZ was obtained in the same manner as in Example 84.

Example 86 Production Method of Pigment CH Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 24.6 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide , And instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2-oxo- In the same manner as in Example 1 except that 32.6 parts of 1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide was used, 55.9 parts of pigment CH was obtained.

Example 87 Production Method of Pigment Composition CI Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide 24 Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide In the same manner as in Example 2, except that 32.6 parts of pigment composition CI was added. Obtained.

Example 88 Production Method of Pigment Composition CJ Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide 24 Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide In the same manner as in Example 6, except for using 32.6 parts of pigment composition CJ, 57.9 parts. Obtained.

Example 89 Production Method of Pigment Composition CK 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide 24 instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide, except that 32.6 parts were used, in the same manner as in Example 9 except that 57.8 parts of pigment composition CK were added. Obtained.

(Example 183) Production method of pigment composition GA Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an aqueous solution of 80% acetic acid 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 57.1 parts of pigment composition GA was obtained in the same manner as in Example 88.

Example 90 Production Method of Pigment CL Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide 25. Instead of using 6 parts and using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component 26. N-phenyl-3-hydroxy-2-naphthamide 26. 51.4 parts of pigment CL were obtained in the same manner as in Example 1 except that 9 parts were used.

Example 91 Production Method of Pigment Composition CM Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide Instead of using 25.6 parts and using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-phenyl-3-hydroxy-2-naphthamide 53.4 parts of pigment composition CM was obtained in the same manner as in Example 2 except that 26.9 parts were used.

Example 92 Method for Producing Pigment Composition CN Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide Instead of using 25.6 parts and using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-phenyl-3-hydroxy-2-naphthamide Pigment composition CN 53.7 parts was obtained by the same method as Example 6 except using 26.9 parts.

Example 93 Method for Producing Pigment Composition CO Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide Instead of using 25.6 parts and using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-phenyl-3-hydroxy-2-naphthamide 53.3 parts of pigment composition CO were obtained in the same manner as in Example 9, except that 26.9 parts were used.

(Example 184) Production method of pigment composition GB Instead of obtaining an acetic acid aqueous solution by placing 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. 52.0 parts of pigment composition GB was obtained in the same manner as in Example 92 except for maintaining.

Example 94 Method for Producing Pigment CP Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 17.3 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide And a mixture of 6.1 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide and N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component Instead of using 33.4 parts, use 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide. 55.2 parts of pigment CP was obtained in the same manner as in Example 1 except that

Example 95 Method for Producing Pigment Composition CQ Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 17 A mixture of 3 parts and 6.1 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide with N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2 as the coupler component -Instead of using 33.4 parts of naphthamide, 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 57.0 parts of pigment composition CQ were obtained in the same manner as in Example 2 except for using.

Example 96 Method for Producing Pigment Composition CR Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 17 A mixture of 3 parts and 6.1 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide with N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2 as the coupler component -Instead of using 33.4 parts of naphthamide, 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 57.3 parts of pigment composition CR was obtained in the same manner as in Example 6 except that it was used.

(Example 97) Production method of pigment composition CS Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 17 A mixture of 3 parts and 6.1 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide with N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2 as the coupler component -Instead of using 33.4 parts of naphthamide, 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 57.5 parts of pigment composition CS was obtained in the same manner as in Example 9 except that it was used.

(Example 185) Production method of pigment composition GC Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. 56.3 parts of pigment composition GC was obtained in the same manner as in Example 96 except for maintaining.

Example 98 Production Method of Pigment CT Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 6.0 parts of 3-amino-4-methoxybenzanilide and 4-amino-5 Instead of using a mixture of 17.3 parts of -methoxy-N, 2-dimethylbenzenesulfonamide and 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3hydroxy-2-naphthalenecarboxamide 54.0 parts of pigment CT were obtained in the same manner as in Example 1, except that 0.6 part of the mixture was used.

Example 99 Production Method of Pigment Composition CU Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 6.0 parts of 3-amino-4-methoxybenzanilide and 4-amino Using a mixture of 17.3 parts of -5-methoxy-N, 2-dimethylbenzenesulfonamide, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component. Instead of using 31.6 parts N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3-hydroxy-2-naphthalene 57.0 parts of pigment composition CU were obtained in the same manner as in Example 2 except that a mixture of 0.6 parts of carboamide was used.

Example 100 Production Method of Pigment Composition CV Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 6.0 parts of 3-amino-4-methoxybenzanilide and 4-amino Using a mixture of 17.3 parts of -5-methoxy-N, 2-dimethylbenzenesulfonamide, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component. Instead of using 31.6 parts N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3-hydroxy-2-naphthalene 56.3 parts of pigment composition CV were obtained in the same manner as in Example 6, except that a mixture of 0.6 parts of carboamide was used.

Example 101 Method for Producing Pigment Composition CW Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 6.0 parts of 3-amino-4-methoxybenzanilide and 4-amino Using a mixture of 17.3 parts of -5-methoxy-N, 2-dimethylbenzenesulfonamide, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component. Instead of using 31.6 parts N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3-hydroxy-2-naphthalene 56.5 parts of pigment composition CW was obtained in the same manner as in Example 9, except that a mixture of 0.6 parts of carboamide was used.

Example 186 Method for Producing Pigment Composition GD Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 is obtained. The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 55.3 parts of pigment composition GD was obtained in the same manner as in Example 100.

(Example 102) Production method of pigment CX Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-chloro-5 60.7 parts of pigment CX was obtained in the same manner as in Example 1, except that 37.3 parts of (trifluoromethylphenyl) -3-hydroxy-2-naphthamide were used.

(Example 103) Production method of pigment composition CY Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-chloro Except for using 37.3 parts of -5-trifluoromethylphenyl) -3-hydroxy-2-naphthamide, 62.4 parts of a pigment composition CY were obtained in the same manner as in Example 2.

(Example 104) Production method of pigment composition CZ Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-chloro 62.4 parts of pigment composition CZ were obtained in the same manner as in Example 6 except that 37.3 parts of -5-trifluoromethylphenyl) -3-hydroxy-2-naphthamide was used.

(Example 105) Manufacturing method of pigment composition DA Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-chloro 62.7 parts of pigment composition DA were obtained in the same manner as in Example 9, except that 37.3 parts of -5-trifluoromethylphenyl) -3-hydroxy-2-naphthamide was used.

(Example 187) Production method of pigment composition GE Instead of obtaining an acetic acid aqueous solution by putting 51.6 parts of an 80% acetic acid aqueous solution, 335 parts of water and 670 parts of ice in a coupling tank, an 80% acetic acid aqueous solution 51.6 The temperature during the introduction of a solution containing a coupler component into an acetic acid aqueous solution is adjusted to 40 to 45 ° C by appropriately adding ice. Except for maintaining, 62.3 parts of a pigment composition GE was obtained in the same manner as in Example 104.

Comparative Example 1 Production Method of Pigment a 24.2 parts of 3-amino-4-methoxybenzanilide was added to 432.2 parts of water as a base component and stirred to prepare a suspension, and ice was further added. The temperature was adjusted to 5 ° C. 39.7 parts of 35% -hydrochloric acid was added thereto, and stirred for 1 hour. Thereafter, 7.1 parts of sodium nitrite was added to 22 parts of water, an aqueous solution prepared was added, and the mixture was stirred for 1 hour for diazotization. 2 parts of sulfamic acid was added to the reaction mixture to eliminate nitrous acid. An aqueous solution consisting of 40.4 parts of 25% -aqueous sodium hydroxide, 52.8 parts of 80% -acetic acid and 40 parts of ice was added to the resulting aqueous solution to obtain a solution containing a diazo component.

On the other hand, N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide 33 as a coupler component was added to a mixed solution of 259.9% aqueous sodium hydroxide solution 99.9 parts heated to 90 ° C. and 670 parts water. 4 parts were added and stirred for 10 minutes to obtain a coupler solution. This coupler solution was introduced into a coupling tank for stirring the solution containing the diazo component over 30 minutes for coupling.

After the introduction of the solution containing the coupler component, the reaction was completed by further stirring for 1 hour. After completion of the reaction, the slurry was heated to 80 ° C., filtered, and washed with water to obtain a press cake of the pigment composition. The press cake was further dried at 90 ° C. for 18 hours and then pulverized to obtain 56.4 parts of pigment a.

(Comparative Example 2) Production method of pigment composition b As a base component, 24.2 parts of 3-amino-4-methoxybenzanilide was added to 432.2 parts of water and stirred to prepare a suspension. In addition, the temperature was adjusted to 5 ° C. 39.7 parts of 35% -hydrochloric acid was added thereto, and stirred for 1 hour. Thereafter, 7.1 parts of sodium nitrite was added to 22 parts of water, an aqueous solution prepared was added, and the mixture was stirred for 1 hour for diazotization. 2 parts of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, thereby preparing a solution containing a diazo component.

In addition, 34.4 parts of an 80% aqueous acetic acid solution, 335 parts of water and 670 parts of ice were placed in a coupling tank and stirred to obtain an aqueous acetic acid solution.

On the other hand, 670 parts of water, 10.0 parts of 70% polyoxyethylene alkyl ether potassium phosphate (manufactured by Kao Corporation: Electrostripper F) and 66.6 parts of 25% -aqueous sodium hydroxide solution are mixed and heated to 80 ° C. Then, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was added as a coupler component and dissolved for 10 minutes to obtain a solution containing the coupler component. This solution was introduced into a coupling tank in which an aqueous acetic acid solution was stirred over 30 minutes for acid precipitation. When all the ice melted during acid precipitation, 400 parts of ice was added. After the introduction of the solution containing the coupler component was completed, this solution was heated to 15 ° C. Furthermore, 29.0 parts of 35% -hydrochloric acid was added to obtain an acid precipitation coupler slurry.

While stirring the acid precipitation coupler slurry, the solution containing the diazo component was added over 20 minutes. After the introduction of the solution containing the diazo component, the reaction was completed by further stirring for 8 hours. After completion of the reaction, the slurry was heated to 80 ° C., filtered, and washed with water to obtain a press cake of the pigment composition. The press cake was dried at 90 ° C. for 18 hours, and then pulverized using a hammer mill equipped with a mesh having a 1 mm mesh to obtain 62.7 parts of pigment composition b.

Comparative Example 3 Production Method of Pigment c Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro-2 -Methoxyphenyl) -3-hydroxy-2-naphthamide 35.4 parts and 3-hydroxy-2-naphthalenecarboxamide, except that a mixture of pigment c 55 .8 parts were obtained.

Comparative Example 4 Production Method of Pigment Composition d Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide and pigment in the same manner as in Comparative Example 2 except that a mixture of 32.4 parts of 3-hydroxy-2-naphthalenecarboxamide is used. 63.5 parts of composition d were obtained.

(Comparative Example 5) Production method of pigment e Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro-2 Comparative example, except that 31.8 parts of -methoxyphenyl) -3-hydroxy-2-naphthamide and 1.6 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide are used In the same manner as in Example 1, 56.5 parts of pigment e was obtained.

Comparative Example 6 Production Method of Pigment Composition f Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro Except that a mixture of 31.8 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 1.6 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide is used. In the same manner as in Comparative Example 2, 63.0 parts of pigment composition f was obtained.

(Comparative Example 7) Production method of pigment composition g Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide 32.4 parts and N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide 0.9 parts except that a mixture is used In the same manner as in Example 1, 56.1 parts of pigment composition g was obtained.

(Comparative Example 8) Manufacturing method of pigment composition h Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (5-chloro 2-methoxyphenyl) -3-hydroxy-2-naphthamide 32.4 parts and N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide 0.9 parts except that a mixture is used In the same manner as in Example 2, 63.5 parts of pigment composition h was obtained.

Comparative Example 9 Production Method of Pigment i Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 25.8 N, N-diethyl-3-amino-4-methoxybenzenesulfonamide Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2,4-dimethoxy-5-chlorophenyl)- 61.5 parts of pigment i was obtained in the same manner as in Comparative Example 1, except that 36.5 parts of 3-hydroxy-2-naphthamide was used.

(Comparative Example 10) Production method of pigment composition j Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N, N-diethyl-3-amino-4-methoxybenzenesulfonamide 25 8 parts, and instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2,4-dimethoxy-5-chlorophenyl) ) 67.0 parts of pigment composition j were obtained in the same manner as in Comparative Example 2, except that 36.5 parts of 3-hydroxy-2-naphthamide were used.

Comparative Example 11 Production Method of Pigment k Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 55.0 parts of pigment k were obtained in the same manner as in Comparative Example 1 except that 31.8 parts of -chlorophenyl) -3-hydroxy-2-naphthamide was used.

Comparative Example 12 Production Method of Pigment Composition l Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 61.5 parts of pigment composition 1 were obtained in the same manner as in Comparative Example 2, except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

Comparative Example 13 Production Method of Pigment m Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3-hydroxy- 49.8 parts of pigment m were obtained in the same manner as in Comparative Example 1 except that 26.9 parts of 2-naphthamide were used.

Comparative Example 14 Production Method of Pigment Composition n Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3- 56.4 parts of pigment composition n were obtained in the same manner as in Comparative Example 2, except that 26.9 parts of hydroxy-2-naphthamide were used.

Comparative Example 15 Production Method of Pigment o Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (4-chloro-2 , 5-dimethoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Comparative Example 1 except that 36.5 parts were used, 58.8 parts of pigment o were obtained.

Comparative Example 16 Production Method of Pigment Composition p Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (4-chloro 66.1 parts of pigment composition p was obtained in the same manner as in Comparative Example 2, except that 36.5 parts of -2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide was used.

Comparative Example 17 Production Method of Pigment q Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 55.3 parts of pigment q were obtained in the same manner as in Comparative Example 1 except that 31.8 parts of -chlorophenyl) -3-hydroxy-2-naphthamide was used.

Comparative Example 18 Production Method of Pigment Composition r Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl 61.5 parts of pigment composition r were obtained in the same manner as in Comparative Example 2, except that 31.8 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide was used.

Comparative Example 19 Production Method of Pigment s Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, 3-hydroxy-2-naphthalenecarbo In the same manner as in Comparative Example 1 except that a mixture of 9.6 parts of amide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide is used, pigment s 49 .5 parts were obtained.

(Comparative Example 20) Production method of pigment composition t Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, 3-hydroxy-2- In the same manner as in Comparative Example 2, except that a mixture of 9.6 parts of naphthalenecarboxamide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was used, the pigment 55.9 parts of composition t were obtained.

Comparative Example 21 Method for Producing Pigment u Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-[(2,3- Dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide, except that 32.6 parts were used, and pigment u 55.0 Got a part.

(Comparative Example 22) Production method of pigment composition v Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-[(2, 3-Dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide, except that 32.6 parts were used, and the pigment composition was the same as in Comparative Example 2. 62.8 parts of v were obtained.

Comparative Example 23 Production Method of Pigment w Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 -Chlorophenyl) -3-hydroxy-2-naphthamide 15.9 parts and N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide 18.3 parts In the same manner as in Comparative Example 1, 56.8 parts of pigment w was obtained.

Comparative Example 24 Production Method of Pigment Composition x Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl Other than using a mixture of 15.9 parts of -5-chlorophenyl) -3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide Produced 63.2 parts of pigment composition x in the same manner as in Comparative Example 2.

Comparative Example 25 Production Method of Pigment y Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 23.0 , And instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2-oxo- In the same manner as in Comparative Example 1, except that 32.6 parts of 1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide was used, 54.9 parts of pigment y were obtained.

Comparative Example 26 Production Method of Pigment Composition z Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 23 Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 32.6 parts of pigment composition z in the same manner as in Comparative Example 2 except that 32.6 parts were used. Obtained.

(Comparative Example 27) Production method of pigment aa Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 19.3 parts of butyl 2-aminobenzoate was used, and N- ( Instead of using 33.4 parts of 5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] 51.2 parts of pigment aa was obtained in the same manner as in Comparative Example 1 except that 32.6 parts of -3-hydroxy-2-naphthalenecarboxamide was used.

(Comparative Example 28) Production method of pigment composition ab Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 19.3 parts of butyl 2-aminobenzoate was used and N as the coupler component Instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5- 58.1 parts of pigment composition ab was obtained in the same manner as in Comparative Example 2, except that 32.6 parts of [Il] -3-hydroxy-2-naphthalenecarboxamide was used.

(Comparative Example 29) Production method of pigment ac Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 11.6 parts of 3-amino-4-methoxybenzamide were used, and N as the coupler component Compared with using 36.9 parts of N-phenyl-3-hydroxy-2-naphthamide instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 1, 37.6 parts of pigment ac were obtained.

(Comparative Example 30) Production method of pigment composition ad Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 11.6 parts of 3-amino-4-methoxybenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Comparative Example 2, 44.1 parts of a pigment composition ad was obtained.

(Comparative Example 31) Production method of pigment ae Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline was used as a coupler component. Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide are used, In the same manner as in Comparative Example 1, 53.3 parts of pigment ae was obtained.

(Comparative Example 32) Production method of pigment composition af Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline were used as a coupler. Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a component, except using 26.9 parts N-phenyl-3-hydroxy-2-naphthamide In the same manner as in Comparative Example 2, 60.7 parts of pigment composition af was obtained.

(Comparative Example 33) Production method of pigment ag Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 13.6 parts of p-aminobenzamide was used, and N- (5- Chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide Instead of using 33.4 parts N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide other than 29.9 parts In the same manner as in Comparative Example 1, 42.4 parts of pigment ag was obtained.

(Comparative Example 34) Production method of pigment composition ah Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 13.6 parts of p-aminobenzamide was used, and N- ( Instead of using 33.4 parts of 5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide are used. Except for this, 49.9 parts of pigment composition ah was obtained in the same manner as in Comparative Example 2.

(Comparative Example 35) Production method of pigment ai Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 15.0 parts of 3-amino-4-methylbenzamide were used, and N as the coupler component Compared with using 36.9 parts of N-phenyl-3-hydroxy-2-naphthamide instead of using 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 1, 41.4 parts of pigment ai was obtained.

(Comparative Example 36) Production method of pigment composition aj Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as a base component, 15.0 parts of 3-amino-4-methylbenzamide were used as a coupler component. Except that 36.9 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide are used instead of 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide. In the same manner as in Comparative Example 2, 47.4 parts of pigment composition aj was obtained.

Comparative Example 37 Method for Producing Pigment ak Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 24.6 of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide , And instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2-oxo- 1H-Benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide was used in the same manner as in Comparative Example 1, except that 32.6 parts of pigment ak was obtained.

(Comparative Example 38) Production method of pigment composition al Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide 24 Instead of using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-[(2,3-dihydro-2- Oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide was used in the same manner as in Comparative Example 2 except that 62.8 parts of the pigment composition al was used. Obtained.

(Comparative Example 39) Production method of pigment am Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide 25. Instead of using 6 parts and using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component 26. N-phenyl-3-hydroxy-2-naphthamide 26. 51.6 parts of pigment am was obtained in the same manner as in Comparative Example 1, except that 9 parts were used.

(Comparative Example 40) Manufacturing method of pigment composition an Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide Instead of using 25.6 parts and using 33.4 parts N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N-phenyl-3-hydroxy-2-naphthamide A pigment composition an of 58.6 parts was obtained in the same manner as in Comparative Example 2 except that 26.9 parts were used.

Comparative Example 41 Production Method for Pigment ao Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 17.3 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide And a mixture of 6.1 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide and N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component Instead of using 33.4 parts, use 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide. Except for this, 54.3 parts of pigment ao were obtained in the same manner as in Comparative Example 1.

(Comparative Example 42) Method for producing pigment composition ap Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide 17 A mixture of 3 parts and 6.1 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide with N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2 as the coupler component -Instead of using 33.4 parts of naphthamide, 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 62.0 parts of pigment composition ap was obtained by the same method as Comparative Example 2 except that it was used.

(Comparative Example 43) Production method of pigment aq Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 6.0 parts of 3-amino-4-methoxybenzanilide and 4-amino-5 Instead of using a mixture of 17.3 parts of -methoxy-N, 2-dimethylbenzenesulfonamide and 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3hydroxy-2-naphthalenecarboxamide 54.4 parts of pigment aq was obtained in the same manner as in Comparative Example 1, except that 0.6 part of the mixture was used.

(Comparative Example 44) Production method of pigment composition ar Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 6.0 parts of 3-amino-4-methoxybenzanilide and 4-amino Using a mixture of 17.3 parts of -5-methoxy-N, 2-dimethylbenzenesulfonamide, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component. Instead of using 31.6 parts N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3-hydroxy-2-naphthalene A pigment composition ar 60.6 parts was obtained in the same manner as in Comparative Example 2 except that a mixture of 0.6 parts of carboamide was used.

(Comparative Example 45) Method for producing pigment as As a coupler component, instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide, N- (2-chloro-5 59.8 parts of pigment as was obtained in the same manner as in Comparative Example 1 except that 37.3 parts of -trifluoromethylphenyl) -3-hydroxy-2-naphthamide was used.

(Comparative Example 46) Production method of pigment composition at Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-chloro 66.6 parts of pigment composition was obtained in the same manner as in Comparative Example 2 except that 37.3 parts of -5-trifluoromethylphenyl) -3-hydroxy-2-naphthamide was used.

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

[Measurement method of apparent density of pigment]
The apparent density of the azo pigment of the present invention was measured according to “Pigment Test Method—Part 12: Apparent Density or Apparent Specific Volume—Section 1: Static Method” described in JIS K 5101-12-1.

[Evaluation method of coloring power and sharpness]
Offset inks were prepared using the pigments or pigment compositions obtained in Examples 1 to 187 and Comparative Examples 1 to 46. Offset ink is 0.5 g of pigment or pigment composition, varnish for offset ink (Tamanol 361 (Arakawa Chemical Industries, Ltd .: rosin modified phenolic resin) 50 parts by weight, linseed oil 20 parts by weight, No. 5 Solvent (Japan Petroleum) Co., Ltd .: Solvent for offset ink) 30 parts by weight and dissolved by heating at 200 ° C.) Dark ink by kneading 2.0 g with a Hoover Muller with a load of 150 lbs. The dark ink 0.2 g and the white ink (50 parts of the offset ink varnish with 50 parts of titanium oxide dispersed) 5.0 g were rotated 25 × 4 with a Hoover Muller loaded with 50 pounds. And mixed to obtain a light color ink.

  This light-colored ink was developed on art paper (Mitsubishi Paper Industries Co., Ltd .: Tokuhishi art double-sided N) and visually evaluated for coloring power and sharpness as follows: ◎, ○, Δ, ×. P. R. 269 (Examples 1 to 17, Examples 106 to 118, Examples 132 to 152, and Comparative Example 2) R. 269 + P. R. 150 (Examples 18 to 21, Examples 119 to 131, Examples 153 to 166 and Comparative Example 4) were prepared by comparing Comparative Example 3 with P.I. R. 269 + P. R. 147 (Examples 22 to 25, Example 167, and Comparative Example 6) were prepared by comparing Comparative Example 5 with P.I. R. 269+ Compounds represented by the chemical formula (3) (Examples 26 to 29, Example 168 and Comparative Example 8) R. 5 (Examples 30 to 33, Example 169 and Comparative Example 10) were prepared by comparing Comparative Example 9 with P.I. R. 31 (Examples 34 to 37, Example 170 and Comparative Example 12) R. 32 (Examples 38 to 41, Example 171 and Comparative Example 14) were prepared by comparing Comparative Example 13 with P.I. R. 146 (Examples 42 to 45, Example 172, and Comparative Example 16) were prepared by comparing Comparative Example 15 with P.I. R. 147 (Examples 46 to 49, Example 173, and Comparative Example 18) were prepared by comparing Comparative Example 17 with P.I. R. 150 + P. R. 269 (Examples 50 to 53, Example 174, and Comparative Example 20) were prepared by comparing Comparative Example 19 with P.P. R. 176 (Examples 54 to 57, Example 175, and Comparative Example 22) were obtained by comparing Comparative Example 21 with P.I. R. 184 (Examples 58-61, Example 176 and Comparative Example 24) R. 185 (Examples 62 to 65, Example 177 and Comparative Example 26) were prepared by comparing Comparative Example 25 with P.I. R. 208 (Examples 66 to 69, Example 18 and Comparative Example 28) were prepared by comparing Comparative Example 27 with P.I. R. 245 (Examples 70 to 73, Example 179, and Comparative Example 30) were prepared by comparing Comparative Example 29 with P.P. R. 258 (Examples 74 to 77, Example 180, and Comparative Example 32) were prepared by comparing Comparative Example 31 with P.P. R. 266 (Examples 78 to 81, Example 181 and Comparative Example 34) were prepared by comparing Comparative Example 33 with P.P. R. 268 (Examples 82 to 85, Example 182 and Comparative Example 36) were prepared by comparing Comparative Example 35 with P.P. V. 32 (Examples 86 to 89, Example 183, and Comparative Example 38) were compared with Comparative Example 37. V. 50 (Examples 90 to 93, Example 184, and Comparative Example 40) R. 85 + P. V. 32 (Examples 94 to 97, Example 185 and Comparative Example 42) were prepared by comparing Comparative Example 41 with P.I. R. 185 + P. V. 176 + P. V. 150+ pigment derivatives (Examples 98 to 101, Example 186 and Comparative Example 44) represent Comparative Example 43, and compounds represented by the chemical formula (4) (Examples 102 to 105, Example 187 and Comparative Example 46) represent Comparative Examples. 45 as Δ (reference). I. No. Comparison was made based on relative evaluation between the two. A case where the coloring power was higher or sharper than the one of △ was marked with ◯, a marked coloring power or a sharpness was marked with ◎, and a low coloring power or a sharpness was marked with ×.

[Evaluation method for easy dispersibility]
Evaluation of easy dispersibility was performed using an offset ink. However, unlike the ink used for the evaluation of coloring power and sharpness, the ink was prepared by the following method of dispersing with a weaker force and in a shorter time. A dark ink for easy dispersibility evaluation was obtained by rotating 0.5 × of the pigment or pigment composition and 2.0 g of the varnish for offset ink 25 × 4 with a Hoover Marler loaded with 50 pounds.
A small amount of this dark color ink was taken and sandwiched between two glass slides and spread well to prepare a slide.
When this preparation was observed with a transmission type optical microscope, x represents a case where an undispersed pigment mass of 40 μm or more (hereinafter referred to as coarse particles) was observed, and Δ represents a case where coarse particles of 20 μm or more were observed. The case where the above coarse particles were observed was evaluated as ○, and the case where no coarse particles of 10 μm or more were observed was evaluated as ◎.

[Method of evaluating workability]
When mixing the varnish and the pigment or pigment composition with the spatula at the time of creating the offset ink, x indicates that the pigment or pigment composition scatters, and ○ indicates that the pigment or pigment composition scatters. .

In each evaluation item of coloring power, sharpness, easy dispersibility, and workability, all the evaluation results were ◯ or more, and at least one evaluation item was ◎.
As shown in the above Tables 1 to 4, the pigments or pigment compositions obtained in Comparative Examples 1 to 46 are more colored, clear, and easily dispersible than the pigments or pigment compositions obtained in Examples 1 to 187. It was inferior to the above, or it was easy to scatter and the workability was difficult.

Claims (5)

An azo pigment comprising a compound represented by the general formula (1), wherein an apparent density defined by JIS K 5101-12-1 is 0.04 g / mL to 0.14 g / mL.
General formula (1)

(In the general formula (1), R ₁ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the following general formula (2).
R ₂ is water atom, A Rukokishiru group, or a butoxycarbonyl group.
R ₃ represents a hydrogen atom, an alkyl group, an alkoxyl group, a carbamoyl group, an N-phenylcarbamoyl group, an N, N-diethylsulfamoyl group, or a benzylsulfonyl group.
R ₄ represents a hydrogen atom, a carbamoyl group, an N-phenylcarbamoyl group, or an N-methylsulfamoyl group.
R ₅ represents a hydrogen atom or an alkyl group.
R ₆ represents a hydrogen atom, an alkyl group, or an alkoxyl group. )
General formula (2)

(In general formula (2),
R ₇ is, water atom, an alkyl group, an alkoxyl group, or a halogen atom.
R ₈ represents a hydrogen atom.
R ₉ represents a hydrogen atom, an alkoxyl group, or a halogen atom.
R ₁₀ represents a hydrogen atom, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a two-Toro group.
R ₁₁ represents a hydrogen atom . ) The azo pigment is C.I. I. Pigment Red 5, 31, 32, 146, 147, 150, 176, 184, 185, 208, 245, 258, 266, 268, 269, C.I. I. 2. The azo pigment according to claim 1, which is at least one azo pigment selected from Pigment Violet 32 and 50, a compound represented by Chemical Formula (3), and a compound represented by Chemical Formula (4).
Chemical formula (3)

Chemical formula (4)

  An azo pigment composition comprising 0.1 to 10% by weight of a surfactant in the azo pigment according to claim 1 or 2 based on the azo pigment. A method for producing an azo pigment, which includes a step of reacting and precipitating an acid in a solution containing a coupler component, and further reacting a diazo component to form an azo pigment, as defined in JIS K 5101-12-1. An apparent density is 0.04 g / mL-0.14 g / mL, The manufacturing method of the azo pigment which consists of a compound represented by General formula (1) characterized by the above-mentioned.
General formula (1)

(In the general formula (1), R ₁ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the following general formula (2).
R ₂ is water atom, A Rukokishiru group, or a butoxycarbonyl group.
R ₃ represents a hydrogen atom, an alkyl group, an alkoxyl group, a carbamoyl group, an N-phenylcarbamoyl group, an N, N-diethylsulfamoyl group, or a benzylsulfonyl group.
R ₄ represents a hydrogen atom, a carbamoyl group, an N-phenylcarbamoyl group, or an N-methylsulfamoyl group.
R ₅ represents a hydrogen atom or an alkyl group.
R ₆ represents a hydrogen atom, an alkyl group, or an alkoxyl group. )
General formula (2)

(In general formula (2),
R ₇ is, water atom, an alkyl group, an alkoxyl group, or a halogen atom.
R ₈ represents a hydrogen atom.
R ₉ represents a hydrogen atom, an alkoxyl group, or a halogen atom.
R ₁₀ represents a hydrogen atom, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a two-Toro group.
R ₁₁ represents a hydrogen atom . )   After the step of heating the solution containing the coupler component to 70 to 100 ° C. and holding it for 0.1 to 10 minutes, the solution containing the coupler component is allowed to react and precipitate, and the diazo component is further reacted. The manufacturing method of the azo pigment of Claim 4 including the process of producing | generating an azo pigment.