JP5747289B2 - Method for producing azo pigment - Google Patents

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, naphthol AS pigments and condensed azo pigments are used as colorants in various fields such as printing inks, plastics, textile printing, inkjet inks, electrophotographic printing, and color filters because of their coloring power, sharpness and good resistance. .

  The method for producing an azo pigment generally includes a step of dissolving a coupler component as a raw material in a basic aqueous solution such as sodium hydroxide, potassium hydroxide, or aqueous ammonia. In the case of a naphthol AS pigment, the naphthol AS derivative, which is a coupler component, has low solubility in a basic aqueous solution, and as a result, a large amount of unreacted coupler component remains in the pigment, resulting in coloring power, clarity, Resistance tends to decrease. In order to avoid this, as disclosed in Patent Document 1, there is a method using methanol or dichlorobenzene during the production process, but it is not advantageous in terms of cost and environmental load from the viewpoint of using an organic solvent. It was. In addition, when the coupler component is dissolved at a high temperature for a long time in order to improve the reaction rate, the coupler component is altered and the aromatic amine in the pigment tends to increase. According to Patent Document 2, if a large amount of aromatic amine is present in the pigment, the Ames test known as a mutagenicity test becomes positive, which is not preferable for safety and health. In the case of the condensed azo pigment, if the coupler component is first condensed with the crosslinking portion, the solubility is remarkably lowered when one diazo component is bonded, and it is difficult to obtain the pigment quantitatively.

JP 2004-123866 A JP 2008-50418 A

  An embodiment of the present invention provides a method for producing an azo pigment that solves the problems of the related art, has a reduced aromatic amine contained in the pigment, has a negative Ames test, and is excellent in coloring power and sharpness. The purpose is to provide.

  That is, an embodiment of the present invention is a method for producing an azo pigment in which a diazo component obtained by diazotizing an aromatic amine and a coupler component are coupled, and the solution containing the coupler component is added for 0.1 minute to 10 minutes. The present invention relates to a method for producing an azo pigment characterized by having a step of holding at 70 to 100 ° C.

  The embodiment of the present invention is characterized in that the step of heating the solution containing the coupler component performs heating in the flow path when the solution containing the coupler component is transferred from the coupler tank to the coupling reaction tank. The present invention relates to a method for producing the above azo pigment.

  An embodiment of the present invention also relates to a method for producing the above azo pigment, wherein the azo pigment to be produced comprises a compound represented by the general formula (1).

(In 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 to} R ₆ are each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, a nitro group, a carbonyl group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a nitrile group, or a benzoylamino group. Further, R ₂ ~ In R ₆ , adjacent groups may be bonded to each other to form a ring.)

(In the general formula (2), R _{7 to} R ₁₁ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, or Represents a benzoylamino group, and R _{7 to} R ₁₁ may combine with each other to form a ring.

  Further, in an embodiment of the present invention, the azo pigment to be produced is C.I. I. Pigment Red 5, 31, 32, 146, 147, 150, 176, 184, 185, 208, 245, 258, 266, 268, 269, C.I. I. It is related with the manufacturing method of the said azo pigment characterized by being in any one of Pigment Violet 32 and 50.

  An embodiment of the present invention also relates to a method for producing the azo pigment, wherein the azo pigment to be produced comprises a compound represented by the following general formula (3).

(In General Formula (3), R _{12 to} R ₁₅ each independently represent a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a nitrile group.
n represents an integer of 1 or 2. R _{16 to} R ₂₅ each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, a nitro group, a carbonyl group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a nitrile group, or benzoyl Represents an amino group. In addition, R _{16 to} R ₂₀ and R _{21 to} R ₂₅ may form a ring by bonding adjacent groups to each other. )

  Further, in an embodiment of the present invention, the azo pigment to be produced is C.I. I. Pigment Red 144, 166, 214, 220, 221, 242, and C.I. I. Pigment Orange 31, which is any one of the above-mentioned azo pigments.

  Further, an embodiment of the present invention is the above azo pigment, wherein the azo pigment to be produced is composed of two or more different azo pigments containing at least one selected from the general formula (1) and the general formula (3). It relates to a manufacturing method.

  Further, according to an embodiment of the present invention, in the heating step, the solution containing a coupler component contains 0.1 to 10% by weight of a surfactant relative to the azo pigment to be produced. The present invention relates to a method for producing a pigment composition.

  In another embodiment of the present invention, the solution containing a coupler component in the heating step contains 0.1 to 50% by weight of a resin with respect to the azo pigment to be produced. The present invention relates to a method for manufacturing a product.

An embodiment of the present invention is an azo pigment produced by the above production method or an azo pigment composition produced by the above production method, wherein the content of the aromatic amine represented by the general formula (8) is The present invention relates to an azo pigment or an azo pigment composition that is 200 ppm or less.

(In the general formula (8), R _{45 to} R ₄₉ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, nitro group, carbonyl group, sulfonic acid group, carbamoyl group, sulfamoyl group. Represents a group, a nitrile group, or a benzoylamino group, and R _{45 to} R ₄₉ may combine with each other to form a ring.

  According to the embodiments of the present invention, it is possible to provide a method for producing an azo pigment having high purity, high coloring power, and high clarity, and a pigment and a pigment composition obtained by the production method.

  The disclosure of this specification relates to the subject matter included in Japanese Patent Application No. 2011-074184 filed on March 30, 2011, which is hereby incorporated by reference in its entirety.

In the method for producing an azo pigment of this embodiment, a solution containing a coupler component is heated to 70 ° C. to 100 ° C. during the production process, and is 0.1 to 10 minutes, preferably 0.25 to 5 minutes, more preferably. Includes holding for 0.25 to 2 minutes. When the holding time is shorter than 0.1 minutes, the coupler component cannot be sufficiently dissolved, and when the holding time is 10 minutes or more, the aromatic amine remaining in the pigment tends to increase. When the heating temperature is lower than 70 ° C., the coupler component cannot be sufficiently dissolved over time, and when the heating temperature is higher than 100 ° C., the aromatic amine in the pigment tends to increase. On the other hand, when the heating temperature is higher than 100 ° C., it boils and it becomes difficult to control the flow rate, and an internal pressure is applied in the flow path, which is dangerous. According to the method for producing an azo pigment of this embodiment, by strictly controlling the heating conditions of the basic aqueous solution, an excessive heat history can be prevented, and the coupler component can be sufficiently added while suppressing alteration of the coupler component by the base. Can be dissolved.
The heating temperature is more preferably 80 to 95 ° C, still more preferably 85 to 95 ° C.

  The method of heating the solution containing the coupler component is preferably performed by heating the flow path when the solution containing the coupler component is transferred from the coupler tank to the coupling reaction tank. When a conventional solution containing a coupler component is heated in a coupler tank, the aromatic amine tends to increase by exposing the coupler component to a high temperature until the solution containing the coupler component rises to a desired temperature. . In addition, by adding the coupler component to the heated basic aqueous solution, the time during which the coupler component is exposed to a high temperature can be shortened, but from the start of adding the coupler component until completely dissolved, the solution containing the coupler component is reduced. From the start to the end of the transfer to the coupling tank, the coupler components are exposed to high temperatures and the aromatic amine tends to increase. On the other hand, the coupler component is added to the heated basic aqueous solution, and after the coupler component is completely dissolved, the temperature can be reduced by adding water, ice, etc. The coupler component tends to remain in the pigment in a large amount.

  If the pigment contains a large amount of aromatic amine, the Ames test tends to be positive. In order to make the Ames test negative, the aromatic amine contained in the pigment is 200 ppm or less, preferably 100 ppm.

  As a heating method of the flow path when transferring the solution containing the coupler component, any method can be used as long as it can obtain a predetermined temperature.

  Examples of the heating method of the flow path include a method in which a pipe through which a solution containing a coupler component passes is passed through a heating medium such as water, steam or oil heated to a predetermined temperature, a method in which a pipe is wound with a heating wire, or by induction electric heating. Examples thereof include a method of heating the pipe, a method of directly blowing steam into the pipe with a steam mixer, a method of directly heating the solution with a microwave, and the like. From the viewpoint of heating efficiency and ease of temperature control, a method of passing a pipe through a heating medium such as heated water, steam, or oil or a method of directly blowing steam into the pipe is preferable. The temperature of the heating medium may be any number of times as long as the solution containing the coupler component can be heated to 70 to 100 ° C.

  Moreover, you may provide a stirring apparatus in a flow path. Any device can be used as long as it can mix liquids. Examples of the device include a method of stirring a magnetic stirring rod by a magnetic force from the outside, a method using a line mixer such as a static mixer, a steam mixer, and the like. It is done. When using a steam mixer, heating and stirring can be performed simultaneously, which is preferable.

  As a method for preparing a solution containing a coupler component, a method of generally moistening powder into a liquid can be used. In order to promote the wetting of the coupler and the subsequent solubility, additives such as a surfactant described later may be added. As an example of a method for preparing a solution containing a coupler component, the coupler component is added and stirred for 2 hours or longer while stirring water or water to which an additive such as a surfactant is added. Furthermore, it can prepare by adding 25% sodium hydroxide aqueous solution as a base and stirring for 1 hour.

  The temperature of the coupler solution before heating is 25 ° C. unless otherwise specified, but it may be any number as long as it is 50 ° C. or less. If it is 50 ° C. or lower, the aromatic amine does not increase.

  A known method can be used as a method for diazotization of an aromatic amine (hereinafter also referred to as a base component), and is not particularly limited. As an example of diazotization, the base component is added to water and stirred, and ice is added to keep the temperature at 5 ° C. or lower. After adding hydrochloric acid and stirring for 1 hour, diazotization can be performed by adding an aqueous sodium nitrite solution and further stirring for 1 hour. If necessary, the pH may be adjusted by adding aqueous sodium hydroxide, acetic acid, hydrochloric acid or the like.

  As a coupling method, a known method can be used, and either a batch method or a continuous method may be used. Examples of batch systems include a reverse coupling method in which a solution containing a coupler component is introduced while stirring a solution containing a diazo component, and a parallel solution in which a solution containing a diazo component and a solution containing a coupler component are simultaneously introduced into a buffer solution. An injection method is mentioned. Examples of continuous systems include those using a microreactor. The compounding ratio of the diazo component and the coupler component is preferably 100: 100 to 100: 110, and more preferably 100: 102 to 100: 107, as a molar ratio.

  As an example of the reverse coupling method, a solution containing a diazo component can be stirred in advance, and a solution containing a coupler component heated in a flow path can be introduced therein. It is desirable to add ice appropriately to the solution containing the diazo component so that the temperature during the coupling is 30 ° C. or lower. After introducing the solution containing the coupler component, the reaction is completed by further stirring for 1 hour. If necessary, the slurry is heated to 80 ° C., filtered and washed with water to obtain an azo pigment press cake. The azo pigment press cake can be dried at 90 ° C. for 18 hours and pulverized with a hammer mill or the like to obtain the azo pigment.

  As the azo pigment, all azo pigments having a known chemical structure are included. From the viewpoint of coloring power, sharpness, hue, and water resistance, the azo pigment is particularly a compound represented by the following general formula (1) or (3). Certain azo pigments are desirable.

(In 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 to} R ₆ are each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, a nitro group, a carbonyl group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a nitrile group, or a benzoylamino group. Further, R ₂ ~ In R ₆ , adjacent groups may be bonded to each other to form a ring.)

(In the general formula (2), R _{7 to} R ₁₁ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, or Represents a benzoylamino group, and R _{7 to} R ₁₁ may combine with each other to form a ring.

(In General Formula (3), R _{12 to} R ₁₅ each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a nitrile group. N is an integer of 1 or 2 R _{16 to} R ₂₅ each independently represent a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, a nitro group, a carbonyl group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a nitrile group, Or represents a benzoylamino group, and R _{16 to} R ₂₀ and R _{21 to} R ₂₅ may be bonded to each other to form a ring.)

Here, as the alkylaminoalkyl group in R ₁ , a methylaminomethyl group, an ethylaminomethyl group, an ethylaminoethyl group, an ethylaminopropyl group, a propylaminoethyl group, a propylaminopropyl group, a dimethylaminomethyl group, dimethylamino Ethyl group, dimethylaminopropyl group, dimethylaminobutyl group, diethylaminomethyl group, diethylaminoethyl group, diethylaminopropyl machine, diethylaminobutyl group, dipropylaminoethyl group, dipropylaminopropyl group, ethylmethylaminoethyl group, ethylmethylamino A propyl group etc. are mentioned.

Examples of the alkyl group in R _{2 to} R ₂₅ include a methyl group, an ethyl group, a linear or branched propyl group, a linear or branched butyl group, a linear or branched pentyl group, a linear or branched hexyl group. Group, lauryl group, myristyl group, cetyl group, stearyl group and the like. As for carbon number of an alkyl group, 1-18 are preferable.

_As the alkoxyl group in R 2 _{to R 25,} a methoxy group, an ethoxy group, a propyl alkoxy group and the like.

_As the halogen atom in R 2 _{to R 25} chlorine, bromine, and iodine.

Examples of the carbamoyl group in R _{2 to} R ₆ and R _{16 to} R ₂₅ include an aminocarbonyl group and a phenylaminocarbonyl group.

Examples of the sulfamoyl group in R _{2 to} R ₆ and R _{16 to} R ₂₅ include an aminosulfonyl group, a methylaminosulfonyl group, a dimethylaminosulfonyl group, a diethylaminosulfonyl group, and a benzylaminosulfonyl group.

  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.

  Examples of the azo pigment represented by the general formula (3) include C.I. I. Pigment Red 144, 166, 214, 220, 221, 242, C.I. I. Pigment Orange 31.

  In the production method of this embodiment, a single azo pigment can be produced, or two or more different azo pigments can be produced. The azo pigment serving as the different component is not particularly limited, but it is preferable that the azo pigment serving as the main component and the base portion or the coupler portion have a common structure.

  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 main coupler component and heterogeneous coupler component that react with the diazo component to form an azo compound include the compounds represented by the general formula (4) and general formula (5), as well as β-naphthol and 3-hydroxy-2-naphtho. Examples thereof include naphthol derivatives such as acid and 2-hydroxy-6-sulfonic acid. The main coupler component and the different coupler component have different structures.

(In General Formula (4), R ₂₆ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the following General Formula (7). In General Formula (5), R ₂₇ to R ₃₀ independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a nitrile group, and n represents an integer of 1 or 2.)

(In the general formula (7), R _{40 to} R ₄₄ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, or Represents a benzoylamino group, and R _{40 to} R ₄₄ may be bonded to each other to form a ring.

Here, the alkylaminoalkyl group in R ₂₆ of the general formula (4) is synonymous with the alkylaminoalkyl group in R ₁ of the general formula (1), and R _{27 to} R ₃₀ of the general formula (5) and the general formula The alkyl group, alkoxyl group and halogen atom in R _{40 to} R ₄₄ of (7) have the same meaning as the alkyl group, alkoxyl group and halogen atom in R _{7 to} R ₁₁ of general formula (2).

  Examples of the main base component and the heterogeneous base component that react with the coupler component to form an azo compound include compounds represented by the general formula (8). The main base component and the different base component have different structures.

Here, the alkyl group, alkoxyl group, halogen atom, carbamoyl group, and sulfamoyl group in R _{45 to} R ₄₉ in the general formula (8) are the alkyl group, alkoxyl 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 the components and passing them through the flow path at the same time.

  The azo pigment produced by the production method of this embodiment has a reduced amount of unreacted aromatic amine as compared with a conventional azo pigment.

  General formula (8) is mentioned as an unreacted aromatic amine.

  When synthesizing the azo pigment, various additives can be added as necessary. 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 or resins.

  When an additive is used when synthesizing an azo pigment, the additive may be used in addition to a solution containing a coupler component or a solution containing a diazo component in advance, and used in addition to the slurry after the coupling reaction. May be. Of the additives, the surfactant and resins are preferably used in addition to the solution containing the coupler component. When the coupling method is a parallel injection method, it can be added to a buffer solution.

  As the surfactant, any anionic, nonionic or amphoteric surfactant can be used. When adding a surfactant to a solution containing a coupler component, anionic or amphoteric is preferable.

  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. Moreover, you may add in emulsion form using organic solvents, such as xylene. These are preferably used in an amount of 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, based on the total weight of the pigment composition, from the viewpoint of the sharpness of the obtained pigment. Can do.

  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 copolymerizing 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. Moreover, from a viewpoint of the clarity of the pigment obtained, these are 0.1 to 50 weight% with respect to the total weight of a pigment composition, More preferably, it can be used in the range of 1 to 30 weight%.

  Examples of the pigment derivative include compounds represented by the following general formulas (9) to (11).

P- [X _1- (Y ₁ ) _k ] _m General formula (9)

(Wherein P represents an organic dye residue.
X ₁ is a direct bond connecting P and Y ₁ , —O—, —S—, —CO—, —SO ₂ —, —NR ₅₀ —, —CONR ₅₀ —, —SO ₂ NR ₅₀ —, —NR _50. CO—, —NR ₅₀ 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 alkoxyl group, or a halogen atom. It may represent a benzene residue or a triazine residue, or a linking group formed by linking two or more of these linking groups (wherein R ₅₀ represents a hydrogen atom, an alkyl group, or a hydroxyalkyl group).
Y ₁ represents —NR ₅₁ R ₅₂ , —SO ₃ · M / j, or —COO · M / j, and R ₅₁ and R ₅₂ each independently represent a hydrogen atom or an optionally substituted alkyl. A 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 ₅₁ and R ₅₂ ; M 1 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 2.
k represents an integer of 1 or 2, and m represents an integer of 1 to 4. )

_{Q- [X 2 - (Y 2} ) k] m general formula (10)

(Wherein Q represents an anthraquinone residue optionally substituted with an alkyl group, amino group, nitro group, hydroxyl group, alkoxyl group, or halogen atom).
X ₂ represents a direct bond, —O—, —S—, —CO—, —SO ₂ —, —NR ₅₀ —, —CONR ₅₀ —, —SO ₂ NR ₅₀ —, —NR ₅₀ CO—, —NR _50. 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 alkoxyl group, a halogen atom, or a trifluoromethyl group. It may be a benzene residue or a triazine residue, or a linking group formed by linking two or more of these linking groups (where R ₅₀ represents a hydrogen atom, an alkyl group, or a hydroxyalkyl group).
Y ₂ represents —NR ₅₁ R ₅₂ , —SO ₃ · M / j, or —COO · M / j, and R ₅₁ and R ₅₂ each independently represent a hydrogen atom or an optionally substituted alkyl. A 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 ₅₁ and R ₅₂ ; 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. )

_{/ X 3 - (Y 3)} p
R—X ₄ — (Y ₄ ) _q General formula (11)
_{\ X 5 - (Y 5)} r

(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 ₅₀ —, —CONR. _{50 -, - SO 2 NR 50} -, - NR 50 CO -, - NR 50 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 , An alkoxyl group, a benzene residue which may be substituted with any of halogen atoms, or a linking group formed by linking two or more of these linking groups (wherein R ₅₀ represents a hydrogen atom, an alkyl group) Or a hydroxyalkyl group).
Y ₃ represents —NR ₅₁ R ₅₂ , —SO ₃ · M / j, or —COO · M / j, and R ₅₁ and R ₅₂ each independently represent a hydrogen atom or an optionally substituted alkyl group. Represents 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 ₅₁ and R ₅₂ ; , 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, alkoxyl 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, organic dye residues in P include diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, polyazo, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone, etc. Anthraquinone dyes, quinacridone dyes, dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindoline dyes, isoindolinone dyes, quinophthalone dyes, selenium dyes, porphyrin dyes, phthalocyanine dyes And metal complex dyes.

Further, X ₁ methylene group in to X ₃ as a linear or branched alkylene group having 1 to 12 carbon atoms, an ethylene group, a propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene , A dexylene group, an undecylene group, a dodexylene group and isomers thereof.

Also, R ₅₁ methyl group as the alkyl group which may be substituted in to R _52, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t- butyl group, and pentyl group, a skeleton, their Examples include one in which one hydrogen may be substituted with any of an amino group, a hydroxyl group, chlorine, bromine, a sulfonic acid group, and a nitro group.

Moreover, as an alkenyl group which may be substituted in R _{51 to} R _{52, 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, or a nitro group. Or any of those optionally substituted.

Examples of the optionally substituted phenyl group in R _{51 to} R ₅₂ 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. It is done.

In addition, the heterocyclic group which may be substituted with nitrogen, oxygen or sulfur atom integrally formed with R ₅₁ and R ₅₂ includes an azolidine ring, oxolane ring, thiolane ring, azole ring, oxol ring, thiol ring, Examples thereof include an azinan ring, an oxane ring, a thiane ring, a pyridine ring, a lactam ring, a pyrazole ring, an imidazole ring, an oxazole ring, and a benzimidazolone ring.

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

  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, from a viewpoint of the clarity of the pigment obtained, these are preferable 0.1-20 weight% with respect to the total weight of a pigment composition, More preferably, it can be used in 1-10 weight%.

  As an example of the general formula (9),

Etc.

  As an example of the general formula (10),

Etc.

  As an example of the general formula (11),

Etc.

  Said compound can be manufactured by the well-known method, for example, Unexamined-Japanese-Patent No. 2010-195906.

  The azo pigment produced by the production method of this embodiment has characteristics excellent in coloring power, sharpness, and safety and health. Therefore, it can be suitably used for printing ink, plastic, textile printing, inkjet ink, electrophotographic printing, color filter and the like.

  Hereinafter, although the manufacturing method of this embodiment is demonstrated by an Example, this invention is not limited to these. In Examples and Comparative Examples, “part” means “part by mass” unless otherwise specified. Further, in the production of pigments, the liquid containing the coupler component before heating was 25 ° C. unless otherwise specified.

Example 1 Method for Producing 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, 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 prepare a solution containing a diazo component.

  On the other hand, as a coupler component, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was mixed with 99.9 parts of a 25% aqueous sodium hydroxide solution and 670 parts of water. A suspension was made. This suspension was passed through a pipe heated with water vapor, heated to 80 ° C., and introduced into a coupling tank in which the solution containing the diazo component was stirred. The flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1.5 minutes.

  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 57.6 parts of pigment A.

(Example 2) Manufacturing method of pigment B The temperature at which the suspension containing the coupler component is heated is 95 ° C, and the suspension containing the first coupler component enters the heating section of the flow path and then exits the heating section. 57.8 parts of pigment B was obtained in the same manner as in Example 1 except that the flow rate was adjusted so that the time was 0.5 minutes.

(Example 3) Method for producing Pigment C A steam mixer is attached to the flow path through which the suspension containing the coupler component passes, and steam is blown into the flow path, the liquid temperature is 80 ° C, and the cup is mixed in 0.5 minutes after steam mixing. 57.6 parts of pigment C was obtained in the same manner as in Example 1 except that the amount of steam and the flow rate were adjusted so as to be introduced into the ring tank.

(Example 4) Production method of pigment composition D At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryldimethylamine N-oxide was added, and the temperature at which the suspension containing the coupler component was heated was 90. The same method as in Example 1 except that the flow rate was adjusted to 0.5 minutes at 0.5 ° C. until the suspension containing the first coupler component entered the heating section of the flow path and exited the heating section. Thus, 59.6 parts of pigment composition D was obtained.

(Example 5) Manufacturing method of pigment composition E At the time of preparing a suspension containing a coupler component, 2.3 parts of sodium dodecylbenzenesulfonate was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. In the same manner as in Example 1, except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. 59.4 parts of pigment composition E were obtained.

(Example 6) Manufacturing method of pigment composition F At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated The flow rate was adjusted to 90 ° C. so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. By this method, 59.8 parts of pigment composition F was obtained.

(Example 7) Manufacturing method of pigment composition G At the time of preparing a suspension containing a coupler component, 2.3 parts of sodium lauryl sulfate was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. In the same manner as in Example 1 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component of the liquid to enter the heating part of the flow path and exit the heating part was 0.5 minutes. 59.8 parts of composition G were obtained.

(Example 8) Manufacturing method of pigment composition H At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. In the same manner as in Example 1, except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 0.5 minutes. 59.7 parts of product H was obtained.

(Example 117) Production method of pigment composition DM At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and the temperature at which the suspension containing the coupler component is heated The same method as in Example 1 except that the flow rate was adjusted to 70 ° C. so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and to exit the heating section was 10 minutes. Thus, 59.6 parts of pigment composition DM was obtained.

(Example 118) Manufacturing method of pigment composition DN At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated Example 1 except that the flow rate was adjusted to 100 minutes at a temperature of 0.1 minutes from when the suspension containing the first coupler component entered the heating section of the flow path to the exit of the heating section. By this method, 59.2 parts of pigment composition DN was obtained.

(Example 9) Manufacturing method of pigment composition I Adding 5.8 parts of Joncryl 683 (manufactured by BASF Japan Ltd.) during the preparation of the suspension containing the coupler component, and heating the suspension containing the coupler component Example 1 except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating part of the flow path and exit the heating part was 0.5 minutes. In the same manner as above, 62.3 parts of pigment composition I was obtained.

(Example 10) Manufacturing method of pigment composition J At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 1 except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating part of the flow path and exit the heating part was 0.5 minutes. In the same manner as above, 62.5 parts of pigment composition J was obtained.

(Example 11) Manufacturing method of pigment composition K During the preparation of a suspension containing a coupler component, 5.8 parts of size pine (manufactured by Arakawa Chemical Co., Ltd.) are added, and the temperature at which the suspension containing the coupler component is heated The flow rate was adjusted to 90 ° C. so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 62.2 parts of pigment composition K was obtained.

(Example 12) Production method of pigment composition L After diazotization, 2.9 parts of compound (1) was added to the solution containing the diazo component, and after stirring for 1 hour after coupling, the pH was adjusted to 7 with an aqueous sodium hydroxide solution. 60.2 parts of pigment composition L was obtained in the same manner as in Example 1 except for adjusting to

(Example 13) Production method of pigment composition M Pigment composition M 60. In the same manner as in Example 1, except that 2.9 parts of compound (2) was added during the preparation of the suspension containing the coupler component. 4 parts were obtained.

(Example 14) Manufacturing method of pigment composition N After diazotization, 2.9 parts of compound (3) was added to the solution containing the diazo component, and after the coupling, the mixture was stirred for 1 hour, and then the pH was adjusted to 7 with an aqueous sodium hydroxide solution. 59.7 parts of pigment composition N was obtained in the same manner as in Example 1 except that the amount of pigment composition N was adjusted.

(Example 15) Production method of pigment composition O Pigment composition O 59. In the same manner as in Example 1, except that 2.9 parts of compound (4) was added during the preparation of the suspension containing the coupler component. 8 parts were obtained.

(Example 16) Production method of pigment composition P After diazotization, 2.9 parts of compound (5) was added to a solution containing a diazo component, and after the coupling, the mixture was stirred for 1 hour and then adjusted to pH 7 with an aqueous sodium hydroxide solution. 59.7 parts of pigment composition P was obtained in the same manner as in Example 1 except that the amount of the pigment composition P was adjusted.

(Example 17) Production method of pigment composition Q Pigment composition Q 60. In the same manner as in Example 1, except that 2.9 parts of compound (6) was added during the preparation of the suspension containing the coupler component. 3 parts were obtained.

(Example 18) Production method of pigment composition R To a slurry after stirring for 1 hour after coupling, 2.9 parts of compound (7) dissolved in hydrochloric acid was added, and then the pH was adjusted to 7 with an aqueous sodium hydroxide solution. 60.0 parts of pigment composition R was obtained in the same manner as in Example 1 except that the adjustment was made.

(Example 19) Production method of pigment composition S To a slurry after stirring for 1 hour after coupling, 2.9 parts of compound (8) dissolved in hydrochloric acid was added, and then the pH was adjusted to 7 with an aqueous sodium hydroxide solution. Except for the adjustment, 59.5 parts of pigment composition S was obtained in the same manner as in Example 1.

Example 20 Method for Producing Pigment T 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 T 57. 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. 3 parts were obtained.

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- (5-chloro-2 Example 1 except that a mixture of 31.8 parts of -methoxyphenyl) -3-hydroxy-2-naphthamide and 0.6 part of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide is used. In the same manner as above, 57.6 parts of pigment U were obtained.

(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- (5-chloro Examples except that a mixture of 32.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide and 0.9 parts of N- [3- (diethylamino) propyl] -3-hydroxy-2-naphthamide is used. In the same manner as in Example 1, 57.5 parts of pigment composition V was obtained.

Example 23 Method for Producing Pigment W Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 25.8 parts of N, N-diethyl-3-amino-4-methoxybenzenesulfonamide And N- (2,4-dimethoxy-5-chlorophenyl) -3 instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component 62.0 parts of pigment W was obtained in the same manner as in Example 1 except that 36.5 parts of -hydroxy-2-naphthamide was used.

(Example 24) Method for producing pigment composition X At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated As in Example 23, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. By this method, 63.9 parts of pigment composition X was obtained.

(Example 25) Manufacturing method of pigment composition Y At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was set to 90 ° C. A pigment composition was prepared in the same manner as in Example 23 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the channel and exit the heating section was 0.5 minutes. 63.8 parts of product Y were obtained.

(Example 26) Manufacturing method of pigment composition Z At the time of preparing a suspension containing a coupler component, 5.8 parts of diprozin K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 23, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 67.2 parts of pigment composition Z was obtained.

Example 27 Method for Producing Pigment AA Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 55.5 parts of pigment AA were obtained in the same manner as in Example 1 except that 31.8 parts of -chlorophenyl) -3-hydroxy-2-naphthamide was used.

(Example 28) Manufacturing method of pigment composition AB At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and the temperature at which the suspension containing the coupler component is heated As in Example 27, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. By this method, 57.2 parts of pigment composition AB was obtained.

Example 29 Method for Producing Pigment Composition AC During the preparation of a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was prepared in the same manner as in Example 27 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 0.5 minutes. 57.5 parts of product AC were obtained.

(Example 30) Manufacturing method of pigment composition AD At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 27, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner, 60.2 parts of pigment composition AD was obtained.

Example 31 Method for Producing Pigment AE Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N-phenyl-3-hydroxy- 51.1 parts of pigment AE were obtained in the same manner as in Example 1 except that 26.9 parts of 2-naphthamide were used.

(Example 32) Method for producing pigment composition AF At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. Thus, 52.8 parts of pigment composition AF was obtained.

Example 33 Method for Producing Pigment Composition AG During the preparation of a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. In the same manner as in Example 31, except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit from the heating section was 0.5 minutes. 53.0 parts of product AG was obtained.

(Example 34) Manufacturing method of pigment composition AH At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 31 except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 56.1 parts of pigment composition AH were obtained.

Example 35 Method for Producing Pigment AI Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the 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, 60.4 parts of pigment AI were obtained.

(Example 36) Manufacturing method of pigment composition AJ At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and the temperature at which the suspension containing the coupler component is heated As in Example 35, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. By this method, 62.2 parts of pigment composition AJ was obtained.

(Example 37) Manufacturing method of pigment composition AK At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was prepared in the same manner as in Example 35 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 62.5 parts of product AK were obtained.

(Example 38) Manufacturing method of pigment composition AL At the time of preparing a suspension containing a coupler component, 5.8 parts of diprozin K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 35, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 65.6 parts of pigment composition AL was obtained.

(Example 39) Production method of pigment AM Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component, N- (2-methyl-5 In the same manner as in Example 1, except that 31.8 parts of -chlorophenyl) -3-hydroxy-2-naphthamide was used, 56.1 parts of pigment AM was obtained.

(Example 40) Manufacturing method of pigment composition AN At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and the temperature at which the suspension containing the coupler component is heated 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 58.1 parts of pigment composition AN was obtained.

Example 41 Method for Producing Pigment Composition AO During the preparation of a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. A pigment composition was prepared in the same manner as in Example 39 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 58.0 parts of product AO were obtained.

(Example 42) Method for producing pigment composition AP At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 39, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 61.2 parts of pigment composition AP was obtained.

Example 43 Method for Producing Pigment AQ Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, 3-hydroxy-2-naphthalenecarbo Pigment AQ 50. 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 was used. 6 parts were obtained.

(Example 44) Method for producing pigment composition AR At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 52.4 parts of pigment composition AR was obtained.

Example 45 Method for Producing Pigment Composition AS At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was prepared in the same manner as in Example 43 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 0.5 minutes. 52.6 parts of product AS were obtained.

(Example 46) Manufacturing method of pigment composition AT At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 43, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner, 55.5 parts of pigment composition AT was obtained.

Example 47 Method for Producing Pigment AU 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, but using 32.6 parts of pigment AU 56.3 parts of pigment AU Got.

(Example 48) Method for producing pigment composition AV At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 58.3 parts of pigment composition AV were obtained.

Example 49 Method for Producing Pigment Composition AW At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was the same as in Example 47 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 58.1 parts of product AW were obtained.

(Example 50) Manufacturing method of pigment composition AX At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 47, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner, 61.5 parts of pigment composition AX was obtained.

Example 51 Method for Producing Pigment AY Instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, N- (2-methyl-5 -Chlorophenyl) Implemented except that 15.9 parts of 3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide are used In the same manner as in Example 1, 58.1 parts of pigment AY were obtained.

(Example 52) Method for producing pigment composition AZ At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. By this method, 60.2 parts of pigment composition AZ was obtained.

Example 53 Method for Producing Pigment Composition BA Adding 2.3 parts of lauryl betaine at the time of preparing a suspension containing a coupler component, heating the suspension containing the coupler component to 90 ° C., The pigment composition was prepared in the same manner as in Example 51 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit from the heating section was 0.5 minutes. 60.2 parts of product BA was obtained.

(Example 54) Manufacturing method of pigment composition BB At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 51, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 63.4 parts of pigment composition BB were obtained.

Example 55 Method for Producing Pigment BC Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 23.0 parts of 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide And N-[(2,3-dihydro-2-oxo-1H) instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component -Benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 55.7 parts of pigment BC were obtained in the same manner as in Example 1 except that 32.6 parts were used.

Example 56 Method for Producing Pigment BD 17.3 parts of 4-amino-5-methoxy-N, 2-dimethylbenzenesulfonamide instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component And 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide 6.1 parts, N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide 33 as the coupler component . Instead of using 4 parts, except using 32.6 parts N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide In the same manner as in Example 1, 56.1 parts of pigment BD was obtained.

Example 57 Production Method of Pigment Composition BE 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- A mixture of 17.3 parts of 5-methoxy-N, 2-dimethylbenzenesulfonamide is used and 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide is used as the coupler component. Instead, 31.6 parts N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and 3-hydroxy-2-naphthalenecarbo 55.4 parts of pigment composition BE were obtained in the same manner as in Example 1 except that a mixture of 0.6 parts of amide was used.

(Example 58) Manufacturing method of pigment composition BF At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 57.7 parts of pigment composition BF were obtained.

(Example 59) Manufacturing method of pigment composition BG At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. A pigment composition was prepared in the same manner as in Example 55 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 57.6 parts of product BG were obtained.

(Example 60) Manufacturing method of pigment composition BH At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 55 except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner, 60.5 parts of pigment composition BH was obtained.

Example 61 Production Method of Pigment BI 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- (5 -Chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide Instead of using 33.4 parts, N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl]- 51.8 parts of pigment BI was obtained in the same manner as in Example 1, except that 32.6 parts of 3-hydroxy-2-naphthalenecarboxamide was used.

(Example 62) Manufacturing method of pigment composition BJ At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and the temperature at which the suspension containing the coupler component is heated 90 ° C., except that the flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. Thus, 53.9 parts of pigment composition BJ were obtained.

(Example 63) Manufacturing method of pigment composition BK At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was set to 90 ° C. The pigment composition was the same as in Example 61 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 0.5 minutes. 54.0 parts of product BK were obtained.

(Example 64) Manufacturing method of pigment composition BL At the time of preparing a suspension containing a coupler component, 5.8 parts of diprozin K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 61, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 56.6 parts of pigment composition BL were obtained.

Example 65 Production Method of Pigment BM 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- Example 1 except that 36.9 parts of (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 above, 38.6 parts of pigment BM was obtained.

(Example 66) Method for producing pigment composition BN At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. Thus, 40.6 parts of pigment composition BN were obtained.

Example 67 Method for Producing Pigment Composition BO At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. In the same manner as in Example 65, except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 0.5 minutes. 40.7 parts of product BO was obtained.

(Example 68) Manufacturing method of pigment composition BP At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 65, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 43.5 parts of pigment composition BP was obtained.

Example 69 Method for Producing Pigment BQ Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 27.7 parts of 2-methoxy-5-benzylsulfonylaniline were used and N as the coupler component Example except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide are used instead of 33.4 parts of-(5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide In the same manner as in Example 1, 54.6 parts of pigment BQ was obtained.

(Example 70) Manufacturing method of pigment composition BR At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. 90 ° C., except that the flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 56.5 parts of pigment composition BR was obtained.

(Example 71) Manufacturing method of pigment composition BS At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was prepared in the same manner as in Example 69 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 56.6 parts of product BS was obtained.

(Example 72) Manufacturing method of pigment composition BT At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 69, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 59.7 parts of pigment composition BT was obtained.

Example 73 Production Method of Pigment BU 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 Instead of using 33.4 parts of 2-methoxyphenyl) -3-hydroxy-2-naphthamide, 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide are used. In the same manner as in Example 1, 43.6 parts of pigment BU was obtained.

(Example 74) Manufacturing method of pigment composition BV At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 45.5 parts of pigment composition BV was obtained.

Example 75 Method for Producing Pigment Composition BW At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. A pigment composition was prepared in the same manner as in Example 73 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 0.5 minutes. 45.7 parts of product BW were obtained.

(Example 76) Manufacturing method of pigment composition BX At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 73, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 48.8 parts of pigment composition BX were obtained.

Example 77 Method for Producing Pigment BY 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- Example 1 except that 36.9 parts of (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 above, 42.0 parts of pigment BY was obtained.

(Example 78) Manufacturing method of pigment composition BZ At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. By this method, 43.9 parts of pigment composition BZ was obtained.

(Example 79) Manufacturing method of pigment composition CA At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. A pigment composition was prepared in the same manner as in Example 77 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 44.1 parts of product CA was obtained.

(Example 80) Manufacturing method of pigment composition CB At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 77, except that the flow rate was adjusted to 90 minutes and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 49.1 parts of pigment composition CB was obtained.

Example 81 Method for Producing Pigment CC Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, 24.6 parts of 4-amino-2,5-dimethoxy-N-methylbenzenesulfonamide And N-[(2,3-dihydro-2-oxo-1H) instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component -Benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide 57.0 parts of pigment CC was obtained in the same manner as in Example 1 except that 32.6 parts were used.

(Example 82) Method for producing pigment composition CD At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated 90 ° C., except that the flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 59.2 parts of pigment composition CD were obtained.

(Example 83) Manufacturing method of pigment composition CE At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was prepared in the same manner as in Example 81 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit the heating section was 0.5 minutes. 56.7 parts of product CE were obtained.

(Example 84) Manufacturing method of pigment composition CF At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 81, except that the flow rate was adjusted to 90 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner, 62.1 parts of pigment composition CF was obtained.

Example 85 Method for Producing Pigment CG Instead of using 24.2 parts of 3-amino-4-methoxybenzanilide as the base component, N- (2-methyl-5-methoxy-4-aminophenyl) benzamide 25.6 , And instead of using 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as the coupler component, 26.9 N-phenyl-3-hydroxy-2-naphthamide 52.5 parts of pigment CG was obtained in the same manner as in Example 1 except that the parts were used.

(Example 86) Manufacturing method of pigment composition CH At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether phosphate is added, and a temperature at which the suspension containing the coupler component is heated. 90 ° C., except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In this way, 54.5 parts of pigment composition CH was obtained.

Example 87 Method for Producing Pigment Composition CI When preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 90 ° C. The pigment composition was the same as in Example 85 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. 54.6 parts of product CI were obtained.

(Example 88) Manufacturing method of pigment composition CJ At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) was added, and the suspension containing the coupler component was heated. Example 85, except that the flow rate was adjusted to 90 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.5 minutes. In the same manner as above, 59.4 parts of pigment composition CJ were obtained.

(Example 89) Production method of pigment CK As a base component (1), 16.2 parts of 2,5-dichloroaniline is added to 432.2 parts of water and stirred to prepare a suspension, and ice is 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, thereby preparing a solution (1) containing a diazo component. Moreover, the solution (2) containing a diazo component was prepared by the same method as the solution (1) containing a diazo component.

  On the other hand, 48.3 parts of N, N ′-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component and 199.8 parts of 25% -aqueous sodium hydroxide solution Then, it was mixed with 1340 parts of water to obtain a solution containing a coupler component.

  While stirring the solution containing the coupler component, the solution (1) containing the diazo component was added to perform coupling. The coupling liquid was passed through a heated pipe and heated to 100 ° C., and the solution (2) containing the diazo component was introduced into a coupling tank for stirring. The flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 2 minutes. 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 81.3 parts of pigment CK.

(Example 90) Manufacturing method of pigment composition CL At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. A method similar to that of Example 89, except that the flow rate was adjusted to 95 ° C. so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. Thus, 83.2 parts of pigment composition CL were obtained.

(Example 91) Manufacturing method of pigment composition CM At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. The pigment composition CM was prepared in the same manner as in Example 89 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. 83.5 parts were obtained.

(Example 92) Method for producing pigment composition CN At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 95, except that the flow rate was adjusted to 95 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. By this method, 86.5 parts of pigment composition CN was obtained.

Example 93 Method for Producing Pigment CO N, N ′-(2-Chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component N, instead of 48.3 parts, In the same manner as in Example 89, except that 44.8 parts of N ′-(1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) were used, 78.8 parts of pigment CO were obtained.

(Example 94) Manufacturing method of pigment composition CP At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate was added, and the temperature at which the suspension containing the coupler component was heated The same method as in Example 93, except that the flow rate was adjusted to 95 ° C. so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. As a result, 80.7 parts of pigment composition CP was obtained.

Example 95 Method for Producing Pigment Composition CQ During the preparation of a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. Pigment composition CQ was prepared in the same manner as in Example 93, except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. 80.6 parts were obtained.

(Example 96) Manufacturing method of pigment composition CR At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. As in Example 93, except that the flow rate was adjusted to 95 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. By this method, 83.5 parts of pigment composition CR was obtained.

Example 97 Method for Producing Pigment CS N, N ′-(2-Chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component N, instead of 48.3 parts, Pigment CS 85.2 in the same manner as in Example 89 except that 51.7 parts of N ′-(2,5-dichloro-1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) was used. Got a part.

(Example 98) Manufacturing method of pigment composition CT At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated The same method as in Example 97, except that the flow rate was adjusted to 95 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. Thus, 87.1 parts of pigment composition CT was obtained.

Example 99 Method for Producing Pigment Composition CU At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. Pigment composition CU was prepared in the same manner as in Example 97, except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. 87.3 parts were obtained.

(Example 100) Manufacturing method of pigment composition CV At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 95, except that the flow rate was adjusted to 95 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. By this method, 90.3 parts of pigment composition CV was obtained.

(Example 101) Production method of pigment CW 21.4 parts of 2-chloroethyl 3-amino-4-methylbenzoate instead of 16.2 parts of 2,5-dichloroaniline as base components (1) and (2) N, N '-(2,5-dimethyl) instead of 48.3 parts N, N'-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component 91.3 parts of pigment CW was obtained in the same manner as in Example 89 except that 47.7 parts of -1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) was used.

(Example 102) Production method of pigment composition CX At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether phosphate is added, and the temperature at which the suspension containing the coupler component is heated A method similar to that in Example 101, except that the flow rate was adjusted to 95 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. Thus, 93.2 parts of pigment composition CX was obtained.

(Example 103) Manufacturing method of pigment composition CY At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. Pigment composition CY was prepared in the same manner as in Example 101 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 1 minute. 93.3 parts were obtained.

(Example 104) Manufacturing method of pigment composition CZ At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 101 except that the flow rate was adjusted to 95 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. In this manner, 96.5 parts of pigment composition CZ were obtained.

(Example 105) Production method of pigment DA As base components (1) and (2), 19.3 parts of 1-methylethyl 3-amino-4-methylbenzoate instead of 16.2 parts of 2,5-dichloroaniline Instead of 48.3 parts of N, N ′-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component. In the same manner as in Example 89, except that 51.7 parts of dichloro-1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) was used, 91.1 parts of pigment DA was obtained.

(Example 106) Manufacturing method of pigment composition DB At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. The same method as in Example 105, except that the flow rate was adjusted to 95 ° C. so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. Thus, 92.9 parts of pigment composition DB was obtained.

Example 107 Method for Producing Pigment Composition DC During the preparation of a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. Pigment composition DC was prepared in the same manner as in Example 105 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit from the heating section was 1 minute. 93.1 parts were obtained.

(Example 108) Manufacturing method of pigment composition DD At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 95, except that the flow rate was adjusted to 95 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. In this way, 96.2 parts of pigment composition DD was obtained.

(Example 109) Production method of pigment DE 19.6 parts of 2-chloro-5- (trifluoromethyl) aniline instead of 16.2 parts of 2,5-dichloroaniline as base components (1) and (2) N, N ′-(2,5-dichloro) instead of 48.3 parts of N, N ′-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component 91.5 parts of pigment DE was obtained in the same manner as in Example 89, except that 51.7 parts of -1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) was used.

(Example 110) Manufacturing method of pigment composition DF At the time of preparing a suspension containing a coupler component, 2.3 parts of polyoxyethylene alkyl ether potassium phosphate is added, and a temperature at which the suspension containing the coupler component is heated. The same method as in Example 109, except that the flow rate was adjusted to 95 ° C. so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. Thus, 93.4 parts of pigment composition DF was obtained.

(Example 111) Manufacturing method of pigment composition DG At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. Pigment composition DG was prepared in the same manner as in Example 109, except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. 93.4 parts were obtained.

(Example 112) Manufacturing method of pigment composition DH At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. Example 109, except that the flow rate was adjusted to 95 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. By this method, 96.6 parts of pigment composition DH were obtained.

(Example 113) Production method of pigment DI As base components (1) and (2), 12.8 parts of 2-chloroaniline instead of 16.2 parts of 2,5-dichloroaniline and N, N 'as a coupler component -(2-Chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) N, N '-(3,3'-dichloro-1,1'-biphenyl instead of 48.3 parts In the same manner as in Example 89, except that 59.1 parts of -4,4'diyl) bis (3-hydroxy-2-naphthalenecarboxamide) was used, 86.1 parts of pigment DI were obtained.

(Example 114) Manufacturing method of pigment composition DJ At the time of preparing a suspension containing a coupler component, 2.3 parts of potassium polyoxyethylene alkyl ether phosphate is added, and a temperature at which the suspension containing the coupler component is heated. The same method as in Example 113, except that the flow rate was adjusted to 95 ° C. and the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. Thus, 88.2 parts of pigment composition DJ was obtained.

(Example 115) Manufacturing method of pigment composition DK At the time of preparing a suspension containing a coupler component, 2.3 parts of lauryl betaine was added, and the temperature at which the suspension containing the coupler component was heated was 95 ° C. The pigment composition DK was prepared in the same manner as in Example 113 except that the flow rate was adjusted so that the time taken for the suspension containing the coupler component to enter the heating section of the flow channel and exit from the heating section was 1 minute. 88.3 parts were obtained.

(Example 116) Method for producing pigment composition DL At the time of preparing a suspension containing a coupler component, 5.8 parts of diplozine K-25 (manufactured by Toho Chemical Co., Ltd.) is added, and the suspension containing the coupler component is heated. As in Example 113, except that the flow rate was adjusted to 95 ° C. and the time required for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 1 minute. In this way, 91.1 parts of pigment composition DL was obtained.

(Comparative Example 1) Method for Producing Pigment a Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of a 25% aqueous sodium hydroxide solution heated to 90 ° C and 670 parts of water was added. Implemented except that 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was added, dissolved by stirring for 15 minutes, and then adjusted to 20 ° C. by adding ice. In the same manner as in Example 1, 53.3 parts of pigment a was obtained.

(Comparative Example 2) Method for Producing Pigment b Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. Pigment b was prepared in the same manner as in Example 1 except that 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes. 57.5 parts were obtained.

(Comparative Example 3) Method for Producing Pigment c Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 1, 53.5 parts of pigment c was obtained.

(Comparative Example 4) Method for Producing Pigment d Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 1, 57.0 parts of pigment d was obtained.

(Comparative Example 5) Method for producing pigment e 52.9 parts of pigment e was obtained in the same manner as in Example 1 except that the temperature for heating the suspension containing the coupler component was changed to 60 ° C.

(Comparative Example 6) Method for Producing Pigment f 56.8 parts of Pigment f were obtained in the same manner as in Example 1 except that the temperature for heating the suspension containing the coupler component was changed to 120 ° C.

(Comparative Example 7) Method for Producing Pigment g Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. Other than using 36.5 parts of N- (2,4-dimethoxy-5-chlorophenyl) -3-hydroxy-2-naphthamide, stirring for 15 minutes and dissolving, then adding ice and adjusting to 20 ° C. In the same manner as in Example 23, 56.9 parts of pigment g was obtained.

(Comparative Example 8) Method for Producing Pigment h Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. In the same manner as in Example 23 except that 36.5 parts of N- (2,4-dimethoxy-5-chlorophenyl) -3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes, and the pigment was used. 61.8 parts of h were obtained.

(Comparative Example 9) Method for Producing Pigment i Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 23, to obtain 56.9 parts of pigment i.

(Comparative Example 10) Production method of pigment j Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and then exit the heating section was 15 minutes. In the same manner as in Example 23, 60.6 parts of pigment j was obtained.

(Comparative example 11) Production method of pigment k 56.0 parts of pigment k were obtained in the same manner as in Example 23, except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative example 12) Production method of pigment l 60.7 parts of pigment l was obtained in the same manner as in Example 23, except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 13) Method for Producing Pigment m Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of a 25% aqueous sodium hydroxide solution heated to 90 ° C and 670 parts of water was used. Example 27 and Example 27 were used except that 31.4 parts of N- (3-nitrophenyl) -3-hydroxynaphthalene-2-carboxamide was added, dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice. In the same manner, 50.4 parts of pigment m was obtained.

(Comparative Example 14) Method for Producing Pigment n Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. In the same manner as in Example 27 except that 31.4 parts of N- (3-nitrophenyl) -3-hydroxynaphthalene-2-carboxamide was added and stirred for 30 minutes to dissolve, 55.0 parts of pigment n Got.

(Comparative Example 15) Method for Producing Pigment o Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 27, 51.1 parts of pigment o was obtained.

(Comparative Example 16) Method for Producing Pigment p Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and then exit the heating section is 15 minutes. In the same manner as in Example 27, 54.5 parts of pigment p was obtained.

Comparative Example 17 Production Method of Pigment q 50.6 parts of pigment q was obtained in the same manner as in Example 27 except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 18) Method for Producing Pigment r 54.0 parts of Pigment r was obtained in the same manner as in Example 27 except that the temperature for heating the suspension containing the coupler component was changed to 120 ° C.

(Comparative Example 19) Method for Producing Pigment s Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. In the same manner as in Example 31, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added, dissolved by stirring for 15 minutes, and then adjusted to 20 ° C. by adding ice. 47.3 parts of s were obtained.

(Comparative Example 20) Method for Producing Pigment t Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. 50.7 parts of pigment t were obtained in the same manner as in Example 31, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes.

(Comparative Example 21) Method for Producing Pigment u Except for adjusting the flow rate so that the time it takes for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes Was obtained in the same manner as in Example 31 to obtain 46.9 parts of pigment u.

(Comparative Example 22) Manufacturing method of pigment v Implemented except that the flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and to exit the heating section was 15 minutes. In the same manner as in Example 31, 50.4 parts of pigment v was obtained.

(Comparative example 23) Manufacturing method of pigment w Except having changed the temperature which heats the suspension containing a coupler component into 60 degreeC, it was a method similar to Example 31, and obtained pigment w46.2 parts.

(Comparative Example 24) Method for Producing Pigment x 49.8 parts of Pigment x was obtained in the same manner as in Example 31 except that the temperature for heating the suspension containing the coupler component was changed to 120 ° C.

(Comparative Example 25) Method for Producing Pigment y Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% -aqueous sodium hydroxide heated to 90 ° C and 670 parts of water was added. Other than using 36.5 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide, stirring and dissolving for 15 minutes, then adding ice and adjusting to 20 ° C In the same manner as in Example 35, to obtain 55.4 parts of pigment y.

(Comparative Example 26) Method for Producing Pigment z Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. In the same manner as in Example 35, except that 36.5 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes. 60.0 parts of pigment z was obtained.

(Comparative Example 27) Method for Producing Pigment aa Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 35, 56.0 parts of pigment aa was obtained.

(Comparative Example 28) Method for producing pigment ab Implemented except that the flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and to exit the heating section was 15 minutes. In the same manner as in Example 35, 59.0 parts of pigment ab was obtained.

(Comparative Example 29) Method for Producing Pigment ac 54.8 parts of pigment ac was obtained in the same manner as in Example 35, except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 30) Method for Producing Pigment ad 58.4 parts of pigment ad were obtained in the same manner as in Example 35 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 31) Method for Producing Pigment ae Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. Example 3 except that 31.8 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide was added and dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice. In the same manner as in Example 39, 52.3 parts of pigment ae was obtained.

(Comparative Example 32) Method for Producing Pigment af Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. Pigment af 55 in the same manner as in Example 39 except that 31.8 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes. .7 parts were obtained.

(Comparative Example 33) Method for Producing Pigment Ag Other than adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes In the same manner as in Example 39, 52.0 parts of pigment ag was obtained.

(Comparative Example 34) Method for Producing Pigment ah Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 39, 55.9 parts of pigment ah was obtained.

(Comparative Example 35) Method for producing pigment ai 51.8 parts of pigment ai was obtained in the same manner as in Example 39, except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 36) Method for producing pigment aj 55.4 parts of pigment aj was obtained in the same manner as in Example 39, except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 37) Method for Producing Pigment ak Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% -aqueous sodium hydroxide heated to 90 ° C and 670 parts of water was used. After adding 9.6 parts of 3-hydroxy-2-naphthalenecarboxamide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide and stirring for 15 minutes to dissolve, ice 40.1 parts of pigment ak was obtained in the same manner as in Example 43, except that a mixture adjusted to 20 ° C. was used.

(Comparative Example 38) Method for Producing Pigment al Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. A solution prepared by adding 9.6 parts of 3-hydroxy-2-naphthalenecarboxamide and 16.7 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide and stirring for 30 minutes to dissolve Except for use, 43.1 parts of pigment al was obtained in the same manner as in Example 43.

(Comparative Example 39) Method for Producing Pigment am Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 43, 40.4 parts of pigment am was obtained.

(Comparative Example 40) Method for Producing Pigment an Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and then exit the heating section was 15 minutes. In the same manner as in Example 43, 42.6 parts of pigment an were obtained.

(Comparative example 41) Production method of pigment ao 39.6 parts of pigment ao was obtained in the same manner as in Example 43, except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 42) Method for producing pigment ap 42.8 parts of pigment ap was obtained in the same manner as in Example 43, except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 43) Method for Producing Pigment aq Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. After adding 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and stirring for 15 minutes to dissolve, ice 55.2 parts of pigment aq was obtained in the same manner as in Example 47 except that the mixture was adjusted to 20 ° C.

(Comparative Example 44) Method for Producing Pigment ar Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide (32.6 parts) was added and stirred for 30 minutes to dissolve. 56.1 parts of pigment ar was obtained in the same manner as in Example 47 except for using.

(Comparative Example 45) Method for Producing Pigment as Except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 0.05 minutes. In the same manner as in Example 47, 55.4 parts of pigment as was obtained.

(Comparative Example 46) Pigment at production method Implemented except that the flow rate was adjusted so that it took 15 minutes for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section. In the same manner as in Example 47, 55.9 parts of pigment at were obtained.

(Comparative Example 47) Method for Producing Pigment au 55.2 parts of pigment au was obtained in the same manner as in Example 47, except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 48) Method for producing pigment av 56.4 parts of pigment av was obtained in the same manner as in Example 47, except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 49) Method for Producing Pigment aw Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. 15.9 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide 57.0 parts of pigment aw was obtained in the same manner as in Example 51 except that the mixture was added and stirred for 15 minutes to dissolve, and then the mixture was adjusted to 20 ° C. by adding ice.

(Comparative Example 50) Method for Producing Pigment ax Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. 15.9 parts of N- (2-methyl-5-chlorophenyl) -3-hydroxy-2-naphthamide and 18.3 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthamide 58.3 parts of pigment ax was obtained in the same manner as in Example 51, except that the mixture obtained by adding the above mixture and stirring and dissolving for 30 minutes was used.

(Comparative Example 51) Method for Producing Pigment ay Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 51, 56.8 parts of pigment ay was obtained.

(Comparative Example 52) Method for Producing Pigment az Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 51, 58.2 parts of pigment az was obtained.

(Comparative Example 53) Method for Producing Pigment ba 57.2 parts of pigment ba was obtained in the same manner as in Example 51 except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 54) Method for Producing Pigment bb 58.4 parts of pigment bb was obtained in the same manner as in Example 51 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 55) Method for Producing Pigment bc Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. After adding 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and stirring for 15 minutes to dissolve, ice 54.5 parts of pigment bc was obtained in the same manner as in Example 55 except that a mixture adjusted to 20 ° C. was used.

(Comparative Example 56) Method for Producing Pigment bd Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide (32.6 parts) was added and stirred for 30 minutes to dissolve. 55.2 parts of pigment bd was obtained in the same manner as in Example 55 except that it was used.

(Comparative Example 57) Method for Producing Pigment be Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes In the same manner as in Example 55, 54.9 parts of pigment be were obtained.

(Comparative Example 58) Method for Producing Pigment bf Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 15 minutes. In the same manner as in Example 55, 55.0 parts of pigment bf was obtained.

(Comparative Example 59) Method for producing pigment bg 54.9 parts of pigment bg was obtained in the same manner as in Example 55, except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 60) Method for producing pigment bh 55.1 parts of pigment bh was obtained in the same manner as in Example 55 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 61) Method for Producing Pigment bi Instead of heating the suspension containing the coupler component during the transfer, a mixed solution of 99.9 parts of a 25% -sodium hydroxide aqueous solution heated to 90 ° C and 670 parts of water was used. After adding 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and stirring for 15 minutes to dissolve, ice 47.6 parts of pigment bi were obtained in the same manner as in Example 61 except that a mixture adjusted to 20 ° C. was used.

(Comparative Example 62) Method for Producing Pigment bj Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide (32.6 parts) was added and stirred for 30 minutes to dissolve. 51.0 parts of pigment bj was obtained in the same manner as in Example 61 except that it was used.

(Comparative Example 63) Method for Producing Pigment bk Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 61, 47.6 parts of pigment bk was obtained.

(Comparative Example 64) Manufacturing method of pigment bl Implemented except that the flow rate was adjusted so that the time required for the suspension containing the first coupler component to enter the heating section of the flow path and to exit the heating section was 15 minutes. In the same manner as in Example 61, 51.2 parts of pigment bl was obtained.

(Comparative Example 65) Method for Producing Pigment bm 46.8 parts of pigment bm was obtained in the same manner as in Example 61 except that the temperature for heating the suspension containing the coupler component was changed to 60 ° C.

Comparative Example 66 Method for Producing Pigment bn 50.2 parts of pigment bn was obtained in the same manner as in Example 61 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 67) Method for Producing Pigment bo Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. In the same manner as in Example 65, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added, dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice, the pigment was used. 35.5 parts of bo were obtained.

(Comparative Example 68) Method for Producing Pigment bp Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. 38.0 parts of pigment bp was obtained in the same manner as in Example 65 except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes.

(Comparative Example 69) Method for Producing Pigment bq Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 65, 35.6 parts of pigment bq was obtained.

(Comparative Example 70) Method for Producing Pigment br Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 65, 38.0 parts of pigment br was obtained.

(Comparative Example 71) Method for producing pigment bs 35.2 parts of pigment bs was obtained in the same manner as in Example 65 except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 72) Method for Producing Pigment bt 37.8 parts of pigment bt was obtained in the same manner as in Example 65 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 73) Method for Producing Pigment bu Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% -aqueous sodium hydroxide heated to 90 ° C and 670 parts of water was added. In the same manner as in Example 69, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice, the pigment was used. 49.7 parts of bu were obtained.

(Comparative Example 74) Method for Producing Pigment bv Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. 53.6 parts of pigment bv was obtained in the same manner as in Example 69 except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes.

(Comparative Example 75) Method for Producing Pigment bw Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 69, 50.2 parts of pigment bw was obtained.

(Comparative Example 76) Method for Producing Pigment bx Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 69, 54.0 parts of pigment bx was obtained.

(Comparative example 77) Manufacturing method of pigment by By the same method as Example 69 except having changed the temperature which heats the suspension containing a coupler component into 60 degreeC, 50.0 parts of pigment by were obtained.

(Comparative Example 78) Method for Producing Pigment bz 53.4 parts of pigment bz was obtained in the same manner as in Example 69 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 79) Method for Producing Pigment ca Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. Example 73 except that 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide was added and dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice. In the same manner, 39.7 parts of pigment ca was obtained.

(Comparative Example 80) Method for Producing Pigment cb Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. Pigment cb 43. In the same manner as in Example 73, except that 29.9 parts of N- (2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide was added and dissolved by stirring for 30 minutes. 1 part was obtained.

(Comparative Example 81) Method for Producing Pigment cc Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 73, 39.7 parts of pigment cc was obtained.

(Comparative Example 82) Pigment cd production method Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 73, 42.5 parts of pigment cd was obtained.

(Comparative Example 83) Method for Producing Pigment ce 39.5 parts of Pigment ce was obtained in the same manner as in Example 73 except that the temperature for heating the suspension containing the coupler component was changed to 60 ° C.

(Comparative example 84) Manufacturing method of pigment cf 43.0 parts of pigment cf was obtained by the same method as Example 73 except having changed the temperature which heats the suspension containing a coupler component into 120 degreeC.

(Comparative Example 85) Method for Producing Pigment cg Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. In the same manner as in Example 77, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added, dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice, the pigment was used. 38.5 parts of cg were obtained.

(Comparative Example 86) Method for Producing Pigment ch Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. 41.3 parts of pigment ch was obtained in the same manner as in Example 77 except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes.

(Comparative Example 87) Method for Producing Pigment ci Other than adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes In the same manner as in Example 77, 39.0 parts of pigment ci was obtained.

(Comparative Example 88) Method for Producing Pigment cj Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 77, 41.1 parts of pigment cj was obtained.

(Comparative Example 89) Method for Producing Pigment ck 38.4 parts of pigment ck was obtained in the same manner as in Example 77 except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 90) Method for Producing Pigment Cl 41.3 parts of pigment cl was obtained in the same manner as in Example 77 except that the temperature for heating the suspension containing the coupler component was changed to 120 ° C.

(Comparative Example 91) Method for Producing Pigment cm Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% -aqueous sodium hydroxide heated to 90 ° C and 670 parts of water was added. After adding 32.6 parts of N-[(2,3-dihydro-2-oxo-1H-benzimidazol) -5-yl] -3-hydroxy-2-naphthalenecarboxamide and stirring for 15 minutes to dissolve, ice 52.2 parts of pigment cm was obtained in the same manner as in Example 81 except that a mixture adjusted to 20 ° C. was used.

(Comparative Example 92) Method for Producing Pigment cn Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. N-[(2,3-dihydro-2-oxo-1H-benzimidazole) -5-yl] -3-hydroxy-2-naphthalenecarboxamide (32.6 parts) was added and stirred for 30 minutes to dissolve. 55.8 parts of pigment cn was obtained in the same manner as in Example 81 except that it was used.

(Comparative Example 93) Method for Producing Pigment co Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 81, 52.4 parts of pigment co was obtained.

(Comparative Example 94) Method for Producing Pigment cp Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 81, 55.3 parts of pigment cp were obtained.

(Comparative Example 95) Method for Producing Pigment cq 51.7 parts of pigment cq was obtained in the same manner as in Example 81 except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 96) Method for Producing Pigment cr 55.6 parts of pigment cr was obtained in the same manner as in Example 81 except that the temperature for heating the suspension containing the coupler component was changed to 120 ° C.

(Comparative Example 97) Method for Producing Pigment cs Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 90 ° C was used. In the same manner as in Example 85, except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 15 minutes and then adjusted to 20 ° C. by adding ice, the pigment was used. 48.3 parts of cs were obtained.

(Comparative Example 98) Method for Producing Pigment ct Instead of heating the suspension containing the coupler component during transfer, a mixture of 99.9 parts of 25% aqueous sodium hydroxide and 670 parts of water heated to 80 ° C was used. 51.7 parts of pigment ct was obtained in the same manner as in Example 85 except that 26.9 parts of N-phenyl-3-hydroxy-2-naphthamide was added and dissolved by stirring for 30 minutes.

(Comparative Example 99) Method for Producing Pigment cu Except for adjusting the flow rate so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section is 0.05 minutes. In the same manner as in Example 85, 48.0 parts of pigment cu was obtained.

(Comparative Example 100) Pigment Cv Production Method Implemented except that the flow rate was adjusted so that the time taken for the suspension containing the first coupler component to enter the heating section of the flow path and exit the heating section was 15 minutes. In the same manner as in Example 85, 51.7 parts of pigment cv were obtained.

(Comparative Example 101) Method for producing pigment cw 47.6 parts of pigment cw was obtained in the same manner as in Example 85 except that the temperature at which the suspension containing the coupler component was heated was changed to 60 ° C.

(Comparative Example 102) Method for producing pigment cx 50.9 parts of pigment cx was obtained in the same manner as in Example 85 except that the temperature at which the suspension containing the coupler component was heated was changed to 120 ° C.

(Comparative Example 103) Method for Producing Pigment Cy As a base component, 32.4 parts of 2,5-dichloroaniline was added to 864.4 parts of water and stirred to prepare a suspension, and ice was added to bring the temperature to 5 Adjusted to ° C. 79.4 parts of 35% -hydrochloric acid was added thereto, and stirred for 1 hour. Then, diazotization was performed by adding 14.2 parts of sodium nitrite to 44 parts of water and adding the prepared aqueous solution and stirring for 1 hour. 4 parts of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, thereby preparing a solution containing a diazo component. On the other hand, 48.3 parts of N, N ′-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) as a coupler component, 199.8 parts of 25% -aqueous sodium hydroxide solution 1340 parts of water was mixed to obtain a solution containing a coupler component.

  While stirring the solution containing the diazo component, the solution containing the coupler component was introduced to perform 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 72.1 parts of pigment cy.

(Comparative Example 104) Method for Producing Pigment cz N, N '-(2-Chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) N as a coupler component instead of 48.3 parts 69.3 parts of pigment cz was obtained in the same manner as in Comparative Example 103 except that 44.8 parts of N '-(1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) was used.

(Comparative Example 105) Method for Producing Pigment da N, N '-(2-Chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) N as a coupler component instead of 48.3 parts Pigment da 75.8 is the same as Comparative Example 103 except that 51.7 parts of N ′-(2,5-dichloro-1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) is used. Got a part.

(Comparative Example 106) Method for producing pigment db As a base component, instead of 32.4 parts of 2,5-dichloroaniline, 42.8 parts of 2-chloroethyl 3-amino-4-methylbenzoate and N, N as coupler components N, N '-(2,5-dimethyl-1,4-phenylene) instead of 48.3 parts of'-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) 80.1 parts of pigment db was obtained in the same manner as in Comparative Example 103 except that 47.7 parts of bis (3-hydroxy-2-naphthalenecarboxamide) was used.

(Comparative Example 107) Method for producing pigment dc 38.6 parts of 1-methylethyl 3-amino-4-methylbenzoate instead of 32.4 parts of 2,5-dichloroaniline as a base component, N, N, N '-(2,5-dichloro-1,4-phenylene) instead of 48.3 parts of N'-(2-chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) ) 80.5 parts of pigment dc was obtained in the same manner as in Comparative Example 103 except that 51.7 parts of bis (3-hydroxynaphthalene-2-carboxamide) was used.

(Comparative Example 108) Method for producing pigment dd 39.2 parts of 2-chloro-5- (trifluoromethyl) aniline instead of 32.4 parts of 2,5-dichloroaniline as a base component and N, N as a coupler component '-(2-Chloro-1,4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) N, N'-(2,5-dichloro-1,4-phenylene) instead of 48.3 parts 80.3 parts of pigment dd was obtained in the same manner as in Comparative Example 103 except that 51.7 parts of bis (3-hydroxynaphthalene-2-carboxamide) was used.

(Comparative Example 109) Method for Producing Pigment de 25.6 parts of 2-chloroaniline instead of 32.4 parts of 2,5-dichloroaniline as a base component, and N, N '-(2-chloro-1 as a coupler component , 4-phenylene) bis (3-hydroxy-2-naphthalenecarboxamide) N, N ′-(3,3′-dichloro-1,1′-biphenyl-4,4′diyl) instead of 48.3 parts In the same manner as in Comparative Example 103, except that 59.1 parts of bis (3-hydroxy-2-naphthalenecarboxamide) was used, 74.2 parts of pigment de was obtained.

  Table 1 summarizes the results of the aromatic amine amount in the pigment, Ames test results, coloring power of the offset ink, and sharpness of the offset ink evaluated according to the evaluation method described later.

  As shown in Table 1, the pigments of Comparative Examples 1 to 109 are inferior in coloring power and sharpness of the offset ink compared to the pigments or pigment compositions of Examples 1 to 118, or have a lot of aromatic amines, and are the results of the Ames test. Was positive.

[Method for measuring unreacted substance in pigment or pigment composition]
80 mg of the pigment or pigment composition was precisely weighed in a sample bottle, 10 ml of methanol was added, and the mixture was dispersed with an ultrasonic cleaner for 1 hour. The dispersion was filtered through a 0.2 μm membrane filter as a sample and analyzed by high performance liquid chromatography under the following conditions.

Apparatus: High-performance liquid chromatograph “2695 Separation Module” manufactured by Nihon Waters Sample: 3 μl
Detector: PDA 240nm
Eluent: Methanol / ammonium phosphate buffer flow rate: 0.5 ml / min
Temperature: 35 ° C
Calibration curve: A calibration curve was prepared based on the result of the same quantitative determination using the target aromatic amine.

[Method of Ames test]
The Ames test was performed by culturing histidine-requiring Salmonella with the test substance added at each concentration, and counting the number of colonies that had become non-histidine-required by reverse mutation. When the number of colonies was more than twice that of the negative control, and this increase showed a dose dependency on the test substance concentration, it was determined as positive.

[Creation and evaluation method of offset ink]
Offset inks were prepared using the pigments or pigment compositions obtained in Examples 1-118 and Comparative Examples 1-109. Offset ink is 0.5 g of pigment, 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 Oil Co., Ltd .: Offset Ink solvent) 30 parts by weight added and dissolved by heating at 200 ° C.) 2.0 g of knead was rotated 100 × 4 with a Hoover Muller under a load of 150 pounds to obtain a dark ink. Dark ink 0.5g and white ink (prepared by dispersing 50 parts of titanium oxide in 50 parts of the above-mentioned offset ink varnish) and mixed by rotating 25 × 4 with a Hoover Muller loaded with 50 pounds As a result, a light color ink was obtained.

  This light-colored ink was spread on a white paper and visually evaluated for coloring power and sharpness by ◎, ○, Δ, and ×. Evaluation is P.M. R. 269 is Comparative Example 2, p. R. 5 is Comparative Example 8; R. 31 is Comparative Example 14; R. 32 is Comparative Example 20; R. 146 is Comparative Example 26, P.I. R. 147 is Comparative Example 32, P.I. R. 150 + P. R. 269 is Comparative Example 38, p. R. 176 is Comparative Example 44, P.I. R. 184 is Comparative Example 50, p. R. 185 is Comparative Example 56, P.I. R. 208 is Comparative Example 62, p. R. 245 is Comparative Example 68, p. R. 258 is Comparative Example 74, p. R. 266 is Comparative Example 80, p. R. 268 is Comparative Example 86, p. V. 32 is Comparative Example 92, p. V. 50 is Comparative Example 98, p. R. 144 is Comparative Example 103, P.I. R. 166 is Comparative Example 104, P.I. R. 214 is Comparative Example 105, p. R. 220 is Comparative Example 106, p. R. 221 is Comparative Example 107, p. R. 242 is Comparative Example 108, p. O. 31 is the same as that of Comparative Example 109 with Δ. I. No. Compared with each other. The case where the coloring power was higher or clearer than the above was evaluated as “◯”, the case where the coloring power was particularly high, or the case where the coloring was particularly high, and the case where the coloring power was low or it was unclear.

Claims (8)

A diazo component obtained by diazotizing an aromatic amine, a compound represented by the general formula (4), a compound represented by the general formula (5), β-naphthol, 3-hydroxy-2-naphthoic acid, and 2-hydroxy-6 A method for producing an azo pigment for coupling with at least one coupler component selected from the group consisting of sulfonic acids, wherein the solution containing the coupler component is heated to 70 to 100 ° C. for 0.1 minutes to 10 The step of heating for a minute and the step of heating the solution containing the coupler component is carried out in the flow path when transferring the solution containing the coupler component from the coupler vessel to the coupling reaction vessel. A method for producing a characteristic azo pigment.
(In General Formula (4), R ₂₆ represents a hydrogen atom, a benzimidazolone group, an alkylaminoalkyl group, or a group represented by the following General Formula (7). In General Formula (5), R ₂₇ to R ₃₀ independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a nitrile group, and n represents an integer of 1 or 2.)
(In the general formula (7), R _{40 to} R ₄₄ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, or Represents a benzoylamino group, and R _{40 to} R ₄₄ may be bonded to each other to form a ring. The method for producing an azo pigment according to claim 1 , wherein the produced azo pigment comprises a compound represented by the general formula (1).
(In 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 to} R ₆ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, nitro group, carbonyl group, sulfonic acid group, carbamoyl group, sulfamoyl group, nitrile group, or benzoyl Represents an amino group. R _{2 to} R ₆ may form a ring by bonding adjacent groups to each other. )
(In the general formula (2), R _{7 to} R ₁₁ are each independently a hydrogen atom, alkyl group, alkoxyl group, halogen atom, trifluoromethyl group, sulfonic acid group, carboxyl group, hydroxyl group, nitro group, or Represents a benzoylamino group, and R _{7 to} R ₁₁ may combine with each other to form a ring. The azo pigment produced is C.I. I. Pigment Red 5, 31, 32, 146, 147, 150, 176, 184, 185, 208, 245, 258, 266, 268, 269, C.I. I. The method for producing an azo pigment according to claim 2 , which is any one of Pigment Violet 32 and 50. The method for producing an azo pigment according to claim 1 , wherein the produced azo pigment comprises a compound represented by the following general formula (3).
(In General Formula (3), R _{12 to} R ₁₅ each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, or a nitrile group. N is an integer of 1 or 2 Represents.
R _{16 to} R ₂₅ each independently represents a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a trifluoromethyl group, a nitro group, a carbonyl group, a sulfonic acid group, a carbamoyl group, a sulfamoyl group, a nitrile group, or benzoyl Represents an amino group. In addition, R _{16 to} R ₂₀ and R _{21 to} R ₂₅ may form a ring by bonding adjacent groups to each other. ) The azo pigment produced is C.I. I. Pigment Red 144, 166, 214, 220, 221, 242, and C.I. I. The method for producing an azo pigment according to claim 4 , which is any one of Pigment Orange 31. Azo pigments to be manufactured, consisting of the general formulas (1) and (3) two or more different azo pigments containing at least one selected from, according to any one of claims 2-5 A method for producing an azo pigment. The solution containing a coupler component during the heating step contains 0.1 to 10% by weight of a surfactant with respect to the azo pigment to be produced, according to any one of claims 1 to 6. The manufacturing method of the azo pigment of description. The solution containing the coupler component at the time of heating, characterized in that it comprises from 0.1 to 50% by weight of the resin to the azo pigments prepared, according to any one of claims 1 to 6 A method for producing an azo pigment.