JP2010260997A - Pigment composition, pigment dispersion and inkjet ink using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a monoazo pigment composition high in tinting strength, excellent in dispersibility and in crystal stability, and little in impurity content, more practically to provide a pigment composition that settles the problem that the crystal stability of monoazo pigment falls down when primary particle diameter thereof is made very fine, further is excellent in dispersibility even if the particle is very fine, also to provide a pigment dispersion excellent in dispersion stability and an inkjet ink excellent in dischargeability using the same. <P>SOLUTION: The pigment composition contains various monoazo pigments and monoazo pigment derivatives having various substituents. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

The present invention relates to a monoazo pigment composition having high coloring power, excellent dispersibility and crystal stability, and low impurity content. More specifically, the present invention relates to an inkjet ink using the same.

  Up to now, in the field of digital printing such as inkjet method and electrophotographic method, C.I. I. Disazo pigments such as CI Pigment Yellow 12, 13 and 83, C.I. I. Monoazo pigments such as C.I. Pigment Yellow 74; I. Condensed azo pigments such as CI Pigment Yellow 93, 95 and 128 have been mainly used.

  Of these, disazo pigments have good properties such as hue, transparency, and coloring power, but are inferior in light resistance. Furthermore, since dichlorobenzidine is used as a raw material, there is a concern about the effect of degradable organisms, which are produced when discarding printed matter using these pigments, on safety. Condensed azo pigments, although having higher light resistance than monoazo pigments and disazo pigments, are often less colored and more expensive.

  On the other hand, monoazo pigments are relatively inexpensive, have properties superior to disazo pigments in terms of safety and light resistance, and are superior in coloring power to condensed azo pigments. Among them, C.I. I. Pigment Yellow 74 has excellent characteristics and is actively used in various digital printing fields.

  Although monoazo pigments have the above advantages, they are often inferior to disazo pigments in terms of transparency and coloring power. In addition, many of them have low crystal stability against solvents and heat, and depending on the conditions used, problems such as crystal growth and opacification may occur.

  Generally, in order to improve the transparency and coloring power of a pigment, it is effective to make the primary particle diameter of the pigment fine. However, in this case, the aggregation of pigment particles becomes more intense than that of coarse particles, making it difficult to disperse in a uniform state. In addition, monoazo pigments with fine particle diameters often have low crystal stability, and when used as dispersions or inks, there may be problems such as the primary particles of the pigment growing depending on the use conditions. Thereby, the coloring power of the printed matter is greatly reduced, and the quality of the product is significantly reduced. Various studies have been conducted to improve the crystal stability of the fine monoazo pigment as described above, and the methods of Patent Documents 1 to 3 are disclosed.

  Patent Document 1 discloses that 99.8 to 80 mol% of a monoazo pigment having a specific structure and 0.2 to 20 mol% of a monoazo pigment having a substituent different from the monoazo pigment are produced at the time of synthesis. The present invention relates to a coloring composition for image recording for ink-jet inks, which is treated with a kind or a known treating agent. Although the pigment composition obtained by this method has fine particles and is excellent in heat resistance, hue, and transparency, the effect of stabilizing the dispersion is not sufficient.

  Patent Document 2 discloses that a monoazo yellow pigment having a specific structure is prepared by adding 1 to 10 moles of a different base and a different coupler to 100 moles of the base and coupler for the monoazo yellow pigment, respectively. The present invention relates to a method for producing a yellow pigment. According to this method, a yellow pigment having fine particles and excellent in durability, crystal stability, and various optical properties can be produced. However, as in the case of Patent Document 2, the effect of stabilizing the dispersion is not sufficient.

  Patent Document 3 relates to a method for producing a monoazo yellow pigment composition in which a coupling reaction is performed in the presence of a surfactant having a specific structure, and a fatty acid ester is further treated after the reaction. According to this method, a pigment having a fine particle diameter, high coloring power and transparency, and high crystal stability can be produced. However, as in the case of Patent Document 1 and Patent Document 2, the effect of stabilizing the dispersion is not sufficient.

JP-A-10-158555 JP 2000-63694 A Japanese Patent Application Laid-Open No. 2004-83779

An object of the present invention is to solve the problem of a monoazo pigment that crystal stability is lowered when the primary particle size is reduced, and to provide a pigment composition that is fine but excellent in dispersibility.

The present invention provides the following pigment composition.
(1) A pigment composition containing a compound represented by the following general formula 1 and a compound represented by the following general formula 2.

(In formula, m, n, and p represent the integer of 1-3.
X ₁ is a hydrogen atom, is an alkyl group of 1 to 5 carbon atoms, a halogen atom, an alkoxyl group having 1 to 5 carbon atoms, an acetylamino group, a carboxyl group, a sulfone group (two X ₁ is integrated, further And may form a heterocyclic structure which may be substituted, including a nitrogen atom, an oxygen atom or a sulfur atom.
X ₂ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a nitro group, a halogen atom, a sulfone group, an alkoxyl group having 1 to 5 carbon atoms, a carbamoyl group, a sulfamoyl group, an ester having 1 to 5 carbon atoms, a carboxyl group, Represents a trifluoromethyl group (two X ₂ may be combined to form an optionally substituted heterocyclic structure containing an additional nitrogen atom, oxygen atom or sulfur atom).
X ₃ represents either a group represented by X ₂ or a group represented by the following general formula 3 or the following general formula 4.
However, at least one of X ₃ is either a group represented by the following general formula 3 or the following general formula 4. )

(Wherein, _{X 4 is, -SO 2 NR '-, -} CONR'- represents either.
X ₅ is a direct bond connecting X ₄ and X ₆ , an optionally substituted alkylene group having 20 or less carbon atoms, an optionally substituted alkenylene group having 20 or less carbon atoms, Represents any of an arylene group which may have a substituent and has 20 or less carbon atoms (these groups are divalent selected from —NR′—, —O—, —SO ₂ — or —CO—); And may be bonded to each other via a linking group.
X ₆ represents any of a hydrogen atom, —OR ₁ , —NR ₁ R ₂ , —CONR ₁ R ₂ , —SO ₂ NR ₁ R ₂ , and —COOR ₁ .
However, R ′ may have a hydrogen atom, a substituent, an alkyl group having 20 or less carbon atoms, an optionally substituted substituent, an alkenyl group having 20 or less carbon atoms, or a substituent. Or an aryl group having 20 or less carbon atoms.

R ₁ and R ₂ each independently have a hydrogen atom, a substituent, which may have a substituent, an alkyl group having 20 or less carbon atoms, an optionally substituted alkenyl group, which has 20 or less carbon atoms, It represents any of an aryl group which may have a substituent and has 20 or less carbon atoms. R ₁ and R ₂ together may contain an additional nitrogen atom, oxygen atom or sulfur atom, and may form an optionally substituted heterocyclic structure.
R ′ or R ₁ or R ₂ and X ₅ may be combined to form an optionally substituted heterocyclic structure which may contain an additional nitrogen atom, oxygen atom or sulfur atom. )

(In the formula, X ₇ represents —NR′— or —O—.
X ₈ and X ₉ each independently represent any of a group represented by the following general formula 5, —OR ′, —NR ′ ₂ , and a halogen atom.
However, R ′ represents the one defined by the general formula 3. )

(In the formula, X ₅ , X ₆ and X ₇ are those defined by General Formula 3 and General Formula 4)
(2) The content of the compound represented by the general formula 2 is 0.1 to 40 mol of the total amount of the number of moles of the compound represented by the general formula 1 and the number of moles of the compound represented by the general formula 2. %, The pigment composition according to (1).
(3) In a method for producing a pigment in which various aromatic amines are diazotized and then coupled with various acetoacetanilide compounds, compounds represented by the following general formula 6 and compounds represented by the following general formula 7 as aromatic amines: The pigment composition as described in (1) or (2) obtained by making it react with the acetoacetanilide compound represented by the following general formula 8 using a mixture.

(In the formula, m, n, p, X ₁ , X ₂ , and X ₃ represent those defined by General Formula 1 and General Formula 2, respectively.)
(4) In a method for producing a pigment in which various aromatic amines are diazotized and then coupled with various acetoacetanilide compounds, the aromatic amine diazotized compound represented by general formula 6 and the compound represented by general formula 2 are mixed. Then, the pigment composition according to (1) or (2), which is obtained by reacting with an acetoacetanilide compound represented by the general formula 8.
(5) In a method for producing a pigment for coupling with various acetoacetanilide compounds after diazotization of various aromatic amines, after mixing the acetoacetanilide compound represented by general formula 8 with the compound represented by general formula 2, The pigment composition according to (1) or (2), obtained by reacting with a diazotized aromatic amine represented by the general formula 6.
(6) In a method for producing a pigment which is diazotized with various aromatic amines and then coupled with various acetoacetanilide compounds, in a buffer solution of pH 3-6 containing the compound represented by general formula 2, general formula 6 The pigment composition according to (1) or (2), which is obtained by simultaneously adding a diazotized aromatic amine represented by formula (II) and a basic aqueous solution of the acetoacetanilide compound represented by formula (8) at a constant flow rate object.
(7) The pigment composition according to any one of (1) to (6), wherein the average primary particle diameter is 200 nm or less.
(8) The pigment composition according to any one of (1) to (7), wherein the specific conductivity of the aqueous solution obtained by boiling and extracting the pigment composition with ion-exchanged water is less than 200 μS / cm.
(9) The pigment composition according to any one of (1) to (8), wherein the total content of calcium, magnesium, and iron is less than 300 ppm.
(10) The pigment composition according to any one of (1) to (8), wherein the contents of calcium, magnesium, and iron are each less than 150 ppm.
(11) A pigment dispersion containing the pigment composition according to any one of (1) to (10).
(12) An inkjet ink containing the pigment composition according to any one of (1) to (10).

  The pigment composition of the present invention includes various monoazo pigments and monoazo pigment derivatives having a specific basic functional group. A monoazo pigment derivative having a specific functional group has an effect as a pigment dispersant or a crystal growth inhibitor, so that a pigment composition having better dispersibility and crystal stability than a monoazo pigment not containing them can be obtained. It is done.

  The pigment composition of the present invention is described as a compound represented by the above general formula 1 (hereinafter referred to as various monoazo pigments) and a compound represented as the above general formula 2 (hereinafter referred to as various monoazo pigment derivatives). ). Various monoazo pigment derivatives have a high dispersion effect on various monoazo pigments, and further have an effect as a crystal growth inhibitor. Therefore, even if a very fine monoazo pigment is used, a pigment composition having excellent dispersibility and crystal stability can be produced.

  The type of various monoazo pigments is not particularly limited. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 9, 49, 61, 62, 65, 73, 74, 75, 97, 98, 105, 111, 116, 120, 130, 133, 151, 154, 167, 168, 169, 175, 181, 194, 203, 213 and the like. Of these, C.I. is preferred in terms of hue, clarity and transparency. I. Pigment Yellow 74 is particularly preferable. These monoazo pigments may be used alone or in combination.

  The form of various monoazo pigments used in the present invention is not particularly limited. Commercially available pigments may be used as they are, or synthesized and used. Further, if necessary, it may be used after being refined to a desired particle size by a method such as acid pasting, solvent salt milling, or dry milling.

  Various monoazo pigments of the present invention can be synthesized by known methods. A typical synthesis method is illustrated below.

  As a first example, there is a method in which diazotized products of various aromatic amines are added to a slurry containing an acetoacetanilide compound. First, the acetoacetanilide compound represented by the general formula 8 is dissolved in an alkaline aqueous solution having a pH of 10 or more, and poured into a previously prepared acetic acid aqueous solution to prepare a pH 3-6 suspension. On the other hand, various aromatic amines represented by the general formula 6 are added to a hydrochloric acid aqueous solution to prepare a suspension having a pH of 2 or lower, and after cooling to 5 ° C. or lower, sodium nitrite is added to diazo. To do. After completion of diazotization, sulfamic acid is added to the reaction mixture to remove nitrous acid, and an aqueous solution of diazotized product is prepared. A coupling reaction is performed by adding the aqueous solution of the diazotized compound prepared above to a slurry of an acetoacetanilide compound at 10 to 50 ° C. over 30 to 90 minutes, and the resulting slurry is filtered, washed with water, dried and pulverized. Thus, a pigment composition can be obtained.

  As a second example, there is a method in which an alkaline aqueous solution of an acetoacetanilide compound is added to a diazotized aqueous solution of various aromatic amines. First, an acetoacetanilide compound represented by the general formula 8 is dissolved in an alkaline aqueous solution having a pH of 10 or more to prepare an aqueous solution. On the other hand, various aromatic amines represented by the general formula 6 are added to a hydrochloric acid aqueous solution to prepare a suspension having a pH of 2 or lower, and after cooling to 5 ° C. or lower, sodium nitrite is added to diazo. To do. After completion of diazotization, sulfamic acid is added to the reaction mixture to remove nitrous acid, and an aqueous solution containing acetic acid and sodium hydroxide is added to prepare a diazotized aqueous solution having a pH of 2 to 4. A coupling reaction is performed by adding the aqueous solution of the acetoacetanilide compound prepared above to the diazotized aqueous solution at 0 to 30 ° C. over 1 to 60 minutes, and the obtained slurry is filtered, washed with water, dried and pulverized. A pigment composition can be obtained.

  As a third example, a diazo component of an aromatic amine and an alkaline aqueous solution of an acetoacetanilide compound are gradually added at a constant flow rate simultaneously to an aqueous solution prepared by previously adding a base such as acetic acid and sodium hydroxide. A method is mentioned. First, an acetoacetanilide compound represented by the general formula 8 is dissolved in an alkaline aqueous solution having a pH of 10 or more to prepare an aqueous solution. On the other hand, various aromatic amines represented by the general formula 6 are added to a hydrochloric acid aqueous solution to prepare a suspension having a pH of 2 or lower, and after cooling to 5 ° C. or lower, sodium nitrite is added to diazo. To do. After completion of diazotization, sulfamic acid is added to the reaction mixture to remove nitrous acid, and an aqueous solution of diazotized product is prepared. The slurry obtained by performing a coupling reaction by simultaneously adding the aqueous solution of the diazotized compound and the aqueous solution of the acetoacetanilide compound prepared as described above at 30 to 90 minutes at 10 to 50 ° C. while maintaining the pH at 6 or less. The pigment composition can be obtained by filtering, washing with water, drying and grinding.

  Examples of the aromatic amine used in the present invention include 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2- (trifluoromethyl) aniline, 3- (trifluoromethyl) aniline, 4 -(Trifluoromethyl) aniline, o-anisidine, m-anisidine, p-anisidine, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 2-methoxy-4-nitroaniline, 2-methoxy-5 Nitroaniline, 4-methoxy-2-nitroaniline, 2-methyl-3-nitroaniline, 2-methyl-4-nitroaniline, 2-methyl-5-nitroaniline, 2-methyl-6-nitroaniline, 3- Methyl-4-nitroaniline, 4-methyl-2-nitroaniline, 4-methyl-3-nitroaniline, 5-methyl-2-ni Roaniline, 2-chloro-4-nitroaniline, 2-chloro-5-nitroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline, 5-chloro-2-nitroaniline, 2-amino -5-nitrobenzenesulfonic acid, 4-amino-2-nitrobenzenesulfonic acid, 4-amino-3-nitrobenzenesulfonic acid, 2-chloro-4-methylaniline, 2-chloro-5-methylaniline, 2-chloro-6 -Methylaniline, 3-chloro-2-methylaniline, 3-chloro-4-methylaniline, 4-chloro-2-methylaniline, 4-chloro-3-methylaniline, 5-chloro-2-methylaniline, 3 -Amino-4-chlorobenzamide, 4-amino-3-chlorobenzamide, 4-amino-3-methoxy-N-phenyl Zensulfonamide, 4-amino-N- (4-carbamoylphenyl) benzamide, dimethyl aminoterephthalate, dimethyl 5-aminoisophthalate, 6-amino-7-chloro-4-methylquinolin-2 (1H) -one, And 5-aminoisoindoline-1,3-dione. One of these may be used alone, or a plurality of these may be used in combination.

  Examples of the acetoacetanilide compound used in the present invention include acetoacetanilide, o-acetoacetanisidide, p-acetoacetanisidide, 2′-chloroacetoacetanilide, 4′-chloroacetoacetanilide, N-acetoacetyl-o. -Toluidine, N-acetoacetyl-p-toluidine, o-acetoacetaniside, p-acetoacetaniside, p-acetoacetophenidide, 4'-acetylaminoacetoacetanilide, 2 ', 4'-dimethylacetate Acetanilide, 4′-chloro-2′-methylacetoacetanilide, 5′-chloro-2′-methoxyacetoacetanilide, 4′-chloro-2 ′, 5′-dimethoxyacetoacetanilide, 5-acetoacetamide-2-benzimidazolinone , N- (7-Met Shi-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-yl) -3-oxo butanamide, and the like. One of these may be used alone, or a plurality of these may be used in combination.

  When the pigment is made finer by acid pasting, various monoazo pigments are dissolved in concentrated sulfuric acid and mixed with a large excess of water to precipitate fine pigment particles. Thereafter, filtration and washing with water are repeated and dried to obtain finer pigment particles.

  The method of acid pasting is not particularly limited. For example, there is a method in which various monoazo pigments are dissolved in 5 to 30 times by weight of 98% sulfuric acid, and the resulting sulfuric acid solution is mixed with 5 to 30 times by weight of water. Can be mentioned. In this case, the temperature at which various monoazo pigments are dissolved in sulfuric acid is not particularly limited as long as it does not cause a reaction such as decomposition of the raw materials or sulfonation, but it can be carried out in the range of 3 to 40 ° C., for example. Also, there are no particular limitations on the method of mixing the sulfuric acid solution of various monoazo pigments and water, and the conditions such as temperature, but in many cases, particles tend to become finer at low temperatures than when they are precipitated at high temperatures. It is preferably carried out in the range of 0 ° C to 60 ° C. Any water that can be used industrially, such as tap water, well water, and warm water, can be used as the water used at that time, but in order to reduce the temperature rise during precipitation, pre-cooled water is used. Is preferably used.

  The mixing method of the sulfuric acid solution and water is not particularly limited, and any method may be used as long as various monoazo pigments can be completely precipitated. For example, it can be precipitated by a method of injecting a sulfuric acid solution into ice water prepared in advance or a method of continuously injecting it into running water using an apparatus such as an aspirator.

  The slurry obtained by the above method is filtered and washed to remove the acidic component, and then dried and pulverized to obtain the pigment composition of the present invention. When the slurry is filtered, the slurry obtained by mixing the sulfuric acid solution and water may be filtered as it is. However, if the slurry has poor filterability, the slurry may be heated and stirred before filtration. Moreover, you may filter, after neutralizing a slurry with various bases.

  When the pigment is refined by solvent salt milling, a mixture composed of at least three components of various monoazo pigments, a water-soluble inorganic salt and a water-soluble solvent is made into a clay-like mixture, and kneaded with a kneader or the like. The kneaded mixture is put into water and stirred with various stirrers to form a slurry. By filtering this, the water-soluble inorganic salt and the water-soluble solvent are removed. The above-mentioned slurrying, filtration, and water washing are repeated to obtain a refined organic pigment.

  As the water-soluble inorganic salt, sodium chloride, potassium chloride and the like can be used. These inorganic salts are used in an amount of 1 times by weight or more, preferably 20 times by weight or less of the organic pigment. When the amount of the inorganic salt is less than 1 times by weight, it is difficult to sufficiently miniaturize the pigment. On the other hand, when the amount is more than 20 times by weight, a great amount of labor is required to remove the water-soluble inorganic salt and the water-soluble solvent after kneading, and at the same time, the amount of the pigment that can be processed at one time is reduced. It is not preferable in terms.

  In the above-described method for refining the pigment, heat is often generated with kneading, and therefore, from the viewpoint of safety, it is preferable to use a water-soluble solvent having a boiling point of about 120 to 250 ° C. Examples include 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol. Monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, Examples include low molecular weight polypropylene glycol.

  When the pigment is refined by dry milling, the various monoazo pigments are refined by dry pulverization with various pulverizers. In this method, the pulverization proceeds through collision and friction between the pulverizing media. An apparatus used for performing dry milling is not particularly limited, and examples thereof include a ball mill, an attritor, and a vibration mill which are dry pulverization apparatuses incorporating a pulverization medium such as beads. When dry pulverization is performed using these apparatuses, the inside of the pulverization container may be decompressed or filled with an inert gas such as nitrogen gas as necessary. Further, after dry milling, the above-described solvent salt milling or stirring treatment in a solvent may be performed.

  In the above-described method for refining a pigment, various monoazo pigments may be used alone or in combination. Moreover, you may use after drying and grind | pulverizing, and you may use it in the form of the water cake before drying.

  Examples of various monoazo pigment derivatives used in the present invention include compounds having the structures shown below. However, the present invention is not limited to these examples. These various monoazo pigment derivatives may be used alone or in combination of two or more. The various monoazo pigment derivatives of the present invention can be synthesized by a known method, for example, in the same manner as the above-described methods for synthesizing various monoazo pigments.

  In preparing the pigment composition in the present invention, various monoazo pigments and various monoazo pigment derivatives can be mixed by any method. Examples of the mixing method include, for example, a method of mixing various monoazo pigments synthesized in advance and various monoazo pigment derivatives in powder form, a method of mixing water slurries with each other, a powdered or mixed water slurry of various monoazo pigments synthesized in advance. Examples include a method of adding various dissolved monoazo pigment derivatives, a method of simultaneously generating various monoazo pigment derivatives when synthesizing various monoazo pigments, and a method of synthesizing various monoazo pigments in the presence of various monoazo pigment derivatives. By any of these methods, a pigment composition having good dispersibility and crystal stability can be obtained.

  In the pigment composition of the present invention, the content of various monoazo pigment derivatives is preferably in the range of 0.1 mol% to 40 mol% of the total amount of various monoazo pigments and various monoazo pigment derivatives. Preferably they are 0.3 mol%-30 mol%, More preferably, they are 0.5 mol%-20 mol%. When the content is less than 0.1 mol%, the dispersibility or crystal stability of the resulting pigment composition becomes insufficient, and when it exceeds 40 mol%, a remarkable dispersion effect or crystal with an increase in the amount added is obtained. A stabilizing effect cannot be obtained, and further, the content of various monoazo pigments is lowered, so that the coloring power may be lowered, which is not preferable.

  As a method for producing the pigment composition of the present invention, among the methods exemplified above, various monoazo pigment derivatives are produced simultaneously when synthesizing various monoazo pigments, or various monoazo pigment derivatives in the presence of various monoazo pigment derivatives. A method for synthesizing a pigment is particularly preferable. When a pigment composition is produced by these methods, a pigment composition is obtained in which very fine and various monoazo pigment derivatives are uniformly treated. Therefore, when used for various applications, a pigment composition having excellent dispersibility and crystal stability and high coloring power and transparency can be obtained, which is particularly preferable.

  When producing a pigment composition by simultaneously producing various monoazo pigment derivatives when synthesizing various monoazo pigments, a compound represented by general formula 6 and a compound represented by general formula 7 are mixed as an aromatic amine. A pigment composition can be produced in the same manner as the method for synthesizing the various monoazo pigments and various monoazo pigment derivatives exemplified above. At that time, the amount of the compound represented by the general formula 7 is in the range of 0.1 mol% to 40 mol% of the total amount of the compound represented by the general formula 6 and the compound represented by the general formula 7. Preferably there is. Preferably they are 0.3 mol%-30 mol%, More preferably, they are 0.5 mol%-20 mol%. When the amount used is less than 0.1 mol%, the dispersibility or crystal stability of the resulting pigment composition becomes insufficient, and when it exceeds 40 mol%, a remarkable dispersion effect and crystals accompanying an increase in the amount added. A stabilizing effect cannot be obtained, and further, the content of various monoazo pigments is lowered, so that the coloring power may be lowered, which is not preferable.

  When producing a pigment composition by a method of synthesizing various monoazo pigments in the presence of various monoazo pigment derivatives, various monoazo pigment derivatives synthesized in advance are added to either the base component or the coupler component, and others are exemplified above. A pigment composition can be produced in the same manner as the method for synthesizing the various monoazo pigments and various monoazo pigment derivatives.

  The pigment composition prepared by any of the above methods may be used after further refined to a desired particle size by a method such as acid pasting, solvent salt milling, or dry milling, if necessary. The method in that case can be performed similarly to the case of the various monoazo pigments.

  In any of the above methods, the pigment composition of the present invention can be produced by adding a resin, a surfactant or the like as necessary. These additives may be used at any stage of preparing the pigment composition. For example, it may be used together with an aromatic amine or an acetoacetamide compound in the step of synthesizing a pigment composition, and may be used when performing acid pasting, solvent salt milling, dry milling, or the like.

  The type of resin used at that time is not particularly limited. For example, rosin resin, acrylic resin, styrene-acrylic resin, polyester resin, polyamide resin, polyurethane resin, fluorine resin, vinylnaphthalene-acrylic Examples thereof include acid resins and styrene-maleic acid resins. These resins may be used alone or in combination of two or more. Moreover, these can be used in 0.1-30 weight% with respect to a pigment composition, Preferably it is 1-15 weight%.

  The type of surfactant used when using the pigment composition is not particularly limited. For example, fatty acid salts, alkyl sulfate esters, alkyl aryl sulfonates, alkyl naphthalene sulfonates, dialkyl sulfonates, dialkyl sulfosuccinates. Acid salt, alkyl diaryl ether disulfonate, alkyl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, naphthalene sulfonic acid formalin condensate, polyoxyethylene alkyl phosphate ester salt, glycerol Late fatty acid ester, polyoxyethylene glycerol fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene oxypropylene block copolymer Rimmer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene alkylamine, fluorine-based nonionic surfactant, silicon-based nonionic surfactant, alkylamine Salts, quaternary amine salts, alkylpyridinium salts, alkylimidazolium salts and the like. These surfactants may be used alone or in combination of two or more. Moreover, these can be used in 0.3-20 weight% with respect to a pigment composition, Preferably it is 1-10% of range.

  As described above, the pigment composition of the present invention prepared by any method preferably has an average primary particle size of 200 nm or less, more preferably 150 nm or less, and still more preferably 100 nm or less. When the average primary particle diameter exceeds 200 nm, coloring power when used in various applications may be inferior, and precipitates may be generated during storage of the dispersion or ink, which is not preferable.

  In the present invention, the average primary particle diameter of the pigment composition can be measured using a scanning electron microscope or a transmission electron microscope. For example, a photograph of pigment particles is taken with a scanning electron microscope or a transmission electron microscope, and the diameter of each primary particle constituting the aggregate is measured. At that time, the diameter of the maximum portion of each particle is defined as the primary particle diameter. This measurement is performed on 100 particles included in the same field of view, and the average of the obtained values is defined as the average primary particle size.

  In the pigment composition of the present invention, the specific conductivity of an aqueous solution obtained by boiling and extracting the pigment composition with ion-exchanged water is measured as an index of the ionic impurity content contained in the pigment composition. Generally, it is known that the ionic impurities contained in the pigment composition affect the dispersion stability when used in various applications, and it is preferable that the ionic impurities be as small as possible. In the present invention, the specific conductivity of the aqueous solution obtained by boiling and extracting the pigment composition with ion-exchanged water is preferably less than 200 μS / cm, more preferably less than 150 μS / cm, and still more preferably less than 100 μS / cm.

  The method for reducing the ionic impurities contained in the pigment composition is not particularly limited as long as the specific conductivity of the aqueous solution obtained by boiling and extracting the pigment composition with ion-exchanged water falls within the above range. The method of repeating filtration and washing | cleaning after preparing a composition is mentioned. Although the kind of water used in that case is not specifically limited, It is preferable that it does not contain ionic impurities, such as distilled water and ion-exchange water.

  In the pigment composition of the present invention, the total content of calcium, magnesium, and iron is preferably less than 300 ppm, more preferably less than 200 ppm, and even more preferably less than 150 ppm. Moreover, it is preferable that content of each metal element is less than 150 ppm, More preferably, it is less than 100 ppm, More preferably, it is less than 80 ppm. When the total content of calcium, magnesium, and iron is 300 ppm or more, or the content of each metal element is 150 ppm or more, when the pigment composition is used for inkjet ink, the ink flow path of the printer and the nozzle of the head This is not preferable because insoluble matters are generated in the portion, which may cause nozzle clogging.

  Various methods for measuring the content of calcium, magnesium, and iron are known. For example, a solution obtained by adding nitric acid to a pigment composition and decomposing it with microwaves is diluted to an appropriate concentration. And a method of measuring using inductively coupled plasma optical emission spectrometry (ICP).

  The method for reducing the content of calcium, magnesium, and iron contained in the pigment composition is not particularly limited. For example, a method of slurrying the pigment composition in an acidic aqueous solution after preparation, and repeating filtration and washing is mentioned. It is done. Although the kind of acid used in that case is not specifically limited, For example, a sulfuric acid, hydrochloric acid, an acetic acid etc. can be mentioned. In addition, the type of water used for washing is not particularly limited, but is preferably one that does not contain ionic impurities such as distilled water or ion-exchanged water.

  The pigment dispersion of the present invention includes both an aqueous pigment dispersion in which the pigment composition of the present invention is dispersed in an aqueous medium and an oily pigment dispersion in which the pigment composition is dispersed in an organic solvent.

The aqueous pigment dispersion of the present invention can be prepared by dispersing a mixture of the pigment composition of the present invention, an aqueous medium, a resin, a surfactant and the like with various dispersers. Moreover, you may add and disperse | distribute various additives other than said raw material as needed. There are no particular restrictions on the order of addition or the method of adding the raw materials when preparing the pigment dispersion.
In the aqueous pigment dispersion of the present invention, the content of the pigment composition is not particularly limited, but it is preferably used in the range of 5 to 50% by weight. Particularly preferably, it is 10 to 40% by weight.

  The type and content of the aqueous medium used for the production of the aqueous pigment dispersion are not particularly limited, but it is preferable to use ion-exchanged water or distilled water from which metal ions and the like have been removed. The content of the aqueous medium is preferably 30 to 95% by weight in the aqueous pigment dispersion.

  Moreover, as an aqueous medium, water and a water-soluble solvent can be mixed and used as needed. The water-soluble solvent is not particularly limited. For example, ethylene glycol, diethylene glycol, propylene glycol, triethylene glycol, polyethylene glycol, glycerin, tetraethylene glycol, dipropylene glycol, ketone alcohol, diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, ethylene glycol mono Examples include ethyl ether, 1,2-hexanediol, N-methyl-2-pyrrolidone, substituted pyrrolidone, 2,4,6-hexanetriol, tetrafuryl alcohol, 4-methoxy-4-methylpentanone. One of these may be used alone, or a plurality of these may be used in combination. When these water-soluble solvents are used, the content of the water-soluble solvent is preferably 1 to 50% by weight in the aqueous pigment dispersion.

  The resin used for the production of the aqueous pigment dispersion is not particularly limited as long as it can disperse the pigment composition in an aqueous medium. For example, those exemplified as resins that can be used for producing the pigment composition Of these, water-soluble ones can be used. One kind of those resins may be used alone, or a plurality of resins may be used in combination. Further, the amount of use thereof is not particularly limited, but is preferably 0.5 to 30% by weight in the pigment dispersion, and more preferably 1 to 20% by weight.

  The surfactant for use in the production of the aqueous pigment dispersion is not particularly limited as long as it can disperse the pigment composition in an aqueous medium, but can be used, for example, when producing a pigment composition. What was illustrated as a surface active agent can be used. Those surfactants may be used alone or in combination. Further, the amount of use thereof is not particularly limited, but is preferably 0.5 to 30% by weight in the pigment dispersion, and more preferably 1 to 20% by weight.

  Furthermore, when manufacturing an aqueous pigment dispersion, additives, such as an antifungal agent, a pH adjuster, and an antifoamer, can be used as needed.

  An antifungal agent is used to prevent generation of wrinkles in the aqueous pigment dispersion. The type of the antifungal agent is not particularly limited. For example, sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione-1-oxide, 1,2-benzisothiazolin-3-one, 1- Examples include amine salts of benzisothiazolin-3-one. These are preferably used in the range of 0.05 to 2% by weight in the pigment dispersion.

  The pH adjuster is used to adjust the pH of the aqueous pigment dispersion to a desired value. Although the kind of pH adjuster is not specifically limited, For example, various amines, various inorganic alkalis, ammonia, various buffer solutions, etc. are mentioned.

  Antifoaming agents are used to prevent foaming in the production of aqueous pigment dispersions. The kind of antifoaming agent is not particularly limited, and any commercially available one can be used. For example, Surfinol 104E, Surfinol 104H, Surfinol 104A, Surfinol 104BC, Surfinol 104DPM, Surfinol 104PA, Surfinol 104PG-50, Surfinol 420, Surfinol 440, Surfinol 465, Surfinol 485, Surfinol PSA-336 (both manufactured by Air Products and Chemicals) and the like can be mentioned.

  The oily pigment dispersion of the present invention can be prepared by dispersing the mixture of the pigment composition of the present invention, an organic solvent, a dispersant and the like with various dispersers. Moreover, you may add and disperse | distribute various additives other than said raw material as needed. There are no particular restrictions on the order of addition or the method of adding the raw materials when preparing the pigment dispersion.

  In the oily pigment dispersion of the present invention, the content of the pigment composition is not particularly limited, but it is preferably used in the range of 5 to 50% by weight. Particularly preferably, it is 10 to 40% by weight.

  The type and content of the organic solvent used for the production of the oil pigment dispersion are not particularly limited, but alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, acetone, methyl ethyl ketone, Methyl-n-propyl ketone, methyl isopropyl ketone, methyl-n-butyl ketone, methyl isobutyl ketone, methyl-n-amyl ketone, methyl isoamyl ketone, diethyl ketone, ethyl-n-propyl ketone, ethyl isopropyl ketone, ethyl-n-butyl ketone , Ketones such as ethyl isobutyl ketone, di-n-propyl ketone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, isophorone, methyl acetate, ethyl acetate, acetic acid-n-propyl, ethyl acetate Esters such as propyl, n-butyl acetate, isobutyl acetate, hexyl acetate, octyl acetate, methyl lactate, propyl lactate, butyl lactate, glycols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol Ethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol dipropyl ether, tripropylene glycol monomethyl ether Glycol ethers such as, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, Diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, glycol acetates such as dipropylene glycol monomethyl ether acetate, n-hexane, isohexane, n-nonane, isononane, dodecane, Saturated hydrocarbons such as isododecane, unsaturated hydrocarbons such as 1-hexene, 1-heptene, 1-octene, cyclic saturated hydrocarbons such as cyclohexane, cycloheptane, cyclooctane, cyclodecane, decalin, cyclohexene, cycloheptene, Cyclic unsaturated hydrocarbons such as cyclooctene, 1,3,5,7-cyclooctatetraene, cyclododecene, benzene, Ene, aromatic hydrocarbons such as xylene. The content of the organic solvent is preferably 30 to 95% by weight in the oil pigment dispersion. One of these may be used alone, or a plurality of these may be used in combination.

  The dispersant used for the production of the oil pigment dispersion is not particularly limited. For example, a hydroxyl group-containing carboxylic acid ester, a salt of a long-chain polyaminoamide and a high-molecular weight acid ester, a salt of a high-molecular-weight polycarboxylic acid, a long-chain polyaminoamide, Polar acid ester salts, high molecular weight unsaturated acid esters, modified polyurethanes, modified polyacrylates, polyallylamine and polyesters having a free carboxylic acid, polyether ester type anionic surfactants, naphthalene Examples thereof include salts of sulfonic acid formalin condensate, aromatic sulfonic acid formalin condensate, polyoxyethylene alkyl phosphate ester, polyoxyethylene alkyl phenyl ether, stearylamine acetate and the like. One of these may be used alone, or a plurality of these may be used in combination. Although the usage-amount of these is not specifically limited, It is preferable that it is 0.5 to 30 weight% in a pigment dispersion, More preferably, it is 1 to 20 weight%.

  The disperser used for producing the pigment dispersion of the present invention is not particularly limited. For example, a horizontal sand mill, a vertical sand mill, an annular bead mill, an attritor, a microfluidizer, a high speed mixer, a homomixer, a homogenizer, and a ball mill. , Paint shakers, roll mills, stone mills, ultrasonic dispersers, and the like, and any disperser or mixer that is usually used to produce various dispersions can be used.

  Further, before dispersion with various dispersers, a pre-dispersion using a kneader mixer such as a kneader or a three roll mill, or a solid dispersion using a two roll mill or the like may be performed. In addition, after being dispersed with various dispersers, post-processing for storing for several hours to one week in a heated state at 30 to 80 ° C., and post-processing using an ultrasonic disperser or a collision type beadless disperser Is effective for imparting dispersion stability to the pigment dispersion. Furthermore, after performing dispersion with various dispersers, treatment with a centrifuge may be performed. This method is effective for removing coarse particles contained in the pigment dispersion.

  The ink-jet ink of the present invention includes both a water-based ink using the water-based pigment dispersion and an oil-based ink using the oil-based pigment dispersion.

The aqueous inkjet ink of the present invention can be produced by adding an aqueous medium, a resin, a surfactant, other additives and the like to the aqueous pigment dispersion of the present invention and mixing them uniformly.
In the aqueous inkjet ink of the present invention, the content of the pigment composition is not particularly limited, but is preferably 1 to 10% by weight, more preferably 2 to 7% by weight in the aqueous inkjet ink.

  The type and content of the aqueous medium used for the production of the aqueous inkjet ink are not particularly limited, but it is preferable to use ion-exchanged water or distilled water from which metal ions have been removed. The content of the aqueous medium is preferably 60 to 99% by weight in the aqueous inkjet ink.

  As the aqueous medium, a water-soluble solvent can be used as necessary in order to prevent drying and solidification of the ink in the nozzle portion of the printer head and to perform stable ejection. Although the kind of water-soluble solvent is not specifically limited, For example, what was illustrated as a water-soluble solvent which can be used by manufacture of an aqueous pigment dispersion is mentioned. One of these may be used alone, or a plurality of these may be used in combination. When these water-soluble solvents are used, the content of the water-soluble solvent is preferably in the range of 1 to 50% by weight in the aqueous inkjet ink.

  In preparing the water-based inkjet ink of the present invention, a resin can be used for imparting fixability of the pigment composition to the printing material. Although the kind of resin is not specifically limited, For example, among what was illustrated as resin which can be used when manufacturing an aqueous pigment dispersion, a water-soluble thing or those oil-in-water emulsions is mentioned. Of these, oil-in-water emulsions are preferred because they can provide a low-viscosity aqueous inkjet ink and a recorded product with excellent water resistance. These resins may be used alone or in combination of a plurality of resins. The content of these resins is preferably 0.5 to 10% by weight, more preferably 1 to 5% by weight in the aqueous inkjet ink. When the content is less than 0.5%, the effect of fixing the pigment composition becomes insufficient. When the content is more than 15%, the viscosity of the ink increases or the ejection stability decreases. It may occur and is not preferable. These resins can be used after neutralizing acidic functional groups with a pH adjuster such as ammonia, various amines, various inorganic alkalis, etc., if necessary.

  When preparing the water-based inkjet ink of the present invention, a surfactant can be used as necessary in order to impart dispersion stability of the pigment composition in the ink. Although the kind of surfactant is not specifically limited, For example, what was illustrated as surfactant which can be used when manufacturing an aqueous pigment dispersion is mentioned. These surfactants may be used alone or in combination of two or more. The content of these surfactants is preferably 0.5 to 10% by weight, more preferably 1 to 5% by weight in the aqueous inkjet ink.

  When manufacturing the water-based inkjet ink of this invention, a drying accelerator, a penetrating agent, an antifungal agent, a chelating agent, a pH adjuster etc. can be used as another additive.

  The drying accelerator can be used for speeding up drying when the aqueous inkjet ink is printed. Although the kind of drying accelerator is not specifically limited, For example, alcohols, such as methanol, ethanol, isopropyl alcohol, are mentioned. One of these may be used alone, or a plurality of these may be mixed and used. Moreover, it is preferable that these content is 1 to 50 weight% in water-based inkjet ink.

  Further, when the substrate to be printed is a permeable substrate such as paper, various penetrants can be used in order to promote ink permeation into the substrate and speed up apparent drying. Examples of penetrants include water-soluble solvents such as diethylene glycol monobutyl ether, alkylene glycol, alkylene diol, polyethylene glycol lauryl ether, sodium lauryl sulfate, sodium dodecylbenzenesulfonate, sodium oleate, di- (2-ethylhexyl) -Surfactants such as sodium sulfosuccinate. The amount of these used is 5% by weight or less in the water-based inkjet ink, and a sufficient effect is obtained. If it is more than this, ink bleeding or paper loss may occur, which is not preferable.

  An antifungal agent can be used to prevent generation of wrinkles in an aqueous inkjet ink. Although the kind of antifungal agent is not specifically limited, What was illustrated as an antifungal agent which can be used when manufacturing an aqueous pigment dispersion can be used, for example. These are preferably used in the range of 0.05 to 1.0% by weight in the aqueous inkjet ink.

  The chelating agent can be used to capture metal ions contained in the water-based inkjet ink and prevent precipitation of insoluble matter in the nozzle portion of the printer head or the ink. The type of chelating agent is not particularly limited, and examples include ethylenediamine tetraacetic acid, sodium salt of ethylenediaminetetraacetic acid, diammonium salt of ethylenediaminetetraacetic acid, and tetraammonium salt of ethylenediaminetetraacetic acid. These are preferably used in the range of 0.005 to 0.5% by weight in the water-based inkjet ink.

  Moreover, in order to adjust pH of water-based inkjet ink to a desired value, various pH adjusters can be used. The kind of pH adjuster is not specifically limited, Various amines, inorganic salt, ammonia, various buffer solutions, etc. can be used.

The oil-based inkjet ink of the present invention can be produced by adding an organic solvent, a resin, a dispersant, other additives and the like to the oil-based pigment dispersion of the present invention and mixing them uniformly.
In the oil-based inkjet ink of the present invention, the content of the pigment composition is not particularly limited, but is preferably 1 to 10% by weight, more preferably 2 to 7% by weight in the oil-based inkjet ink.

  Although the kind of organic solvent used for manufacture of oil-based inkjet ink is not specifically limited, For example, what was illustrated as an organic solvent which can be used when manufacturing an oil-based pigment dispersion can be used. Although content of an organic solvent is not specifically limited, It is preferable that it is 80 to 97 weight% in oil-based inkjet ink. These organic solvents may be used alone or in combination of two or more.

  In producing the oil-based ink jet ink of the present invention, a resin can be used in order to impart fixability of the pigment composition to the printing material. The type of resin is not particularly limited. For example, petroleum resin, casein, shellac, rosin resin, rosin ester resin, cellulose resin, natural rubber, synthetic rubber, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber, Phenol resin, terpene phenol resin, alkyd resin, polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, polyvinyl chloride, polyallylamine resin, vinyl chloride-vinyl acetate resin, ethylene-vinyl acetate resin , Vinylidene chloride resin, acrylic resin, methacrylic resin, urethane resin, silicone resin, fluorine resin, drying oil, synthetic drying oil, maleic acid resin, polyamide resin, polyimide resin, benzoguanamine resin, melamine resin, urea resin, butyral resin, Coumarone indene resin, Cyclohexylene resin, fumaric acid resin, polyolefin, polypropylene chloride, wax - latex resin, a styrene - acrylic resin, a styrene - maleic acid resins. One of these may be used alone, or a plurality of these may be used in combination. Although the usage-amount of these is not specifically limited, It is preferable that it is 1 to 15 weight% in oil-based inkjet ink, More preferably, it is 3 to 8 weight%.

  When preparing the oil-based inkjet ink of the present invention, a dispersant can be used as necessary in order to impart dispersion stability of the pigment composition in the ink. Although the kind of dispersing agent is not specifically limited, What was illustrated as a dispersing agent which can be used when manufacturing an oil-based pigment dispersion can be used, for example. One of these may be used alone, or a plurality of these may be used in combination. Although the usage-amount of these is not specifically limited, It is preferable that it is 0.1 to 15 weight% in oil-based inkjet ink, More preferably, it is 0.5 to 10 weight%.

  The oil-based inkjet ink of the present invention may contain further additives. Examples of the additive include a wetting agent, a degassing agent / defoaming agent, a preservative, and an antioxidant.

  When preparing the ink-jet ink by mixing the above raw materials, the method of mixing the raw materials is not particularly limited, and it can be performed using a high-speed disperser, an emulsifier, etc., in addition to a stirrer using a normal feather. it can. At that time, the order of adding the raw materials and the mixing method are not particularly limited.

  Moreover, the coarse particle contained in ink can be removed by mixing each raw material and filtering the prepared inkjet ink with various filters. The pore size of the filter used at that time is preferably 1 μm or less, and more preferably 0.65 μm or less.

EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to this.
<Preparation of various monoazo pigments and various pigment compositions>
Production Example 1 <Preparation of Monoazo Pigment A (CI Pigment Yellow 74)>
As a diazo component, 67.2 g of 2-methoxy-4-nitroaniline was added to 500 g of water and stirred to prepare a suspension, and ice was added to adjust the temperature to 5 ° C. or lower. Thereto was added 105 g of 35% hydrochloric acid, and the mixture was stirred for 1 hour while maintaining at 5 ° C. or lower. Then, diazotization was performed by adding an aqueous solution prepared by adding 28.0 g of sodium nitrite to 72.0 g of water and stirring for 1 hour. 0.5 g of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a diazonium aqueous solution was prepared.
On the other hand, 84.5 g of o-acetoacetanisid and 164 g of 25% -aqueous sodium hydroxide solution were added to 140 g of water as a coupler component, and the mixture was stirred and completely dissolved. It was poured into an aqueous solution in which 82.0 g of 80% acetic acid and 420 g of water were mixed to prepare a coupler slurry.

  The coupler slurry prepared above was heated to 40 ° C., and a diazonium aqueous solution was dropped therein over 1 hour. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour to complete the reaction. After completion of the reaction, the slurry was heated to 90 ° C., stirred for 1 hour, and then filtered through a Buchner funnel having a diameter of 285 mm. The filter cake was washed with 25 liters of ion-exchanged water, dried, and pulverized to obtain 150 g of monoazo pigment A (CI Pigment Yellow 74).

Production Example 2 <Preparation of Monoazo Pigment B (CI Pigment Yellow 1)>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 60.8 g of 4-methyl-2-nitroaniline, and 84.5 g of o-acetoacetaniside used as a coupler component. 132 g of monoaceto pigment B (CI Pigment Yellow 1) was obtained in the same manner as in Production Example 1 except for changing to 72.2 g of acetoacetanilide.

Production Example 3 <Preparation of Monoazo Pigment C (CI Pigment Yellow 9)>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 60.8 g of 4-methyl-2-nitroaniline, and 84.5 g of o-acetoacetaniside used as a coupler component. 137 g of monoazo pigment C (CI Pigment Yellow 9) was obtained in the same manner as in Production Example 1 except for changing to 78.0 g of N-acetoacetyl-o-toluidine.
Production Example 4 <Preparation of Monoazo Pigment D (CI Pigment Yellow 73)>
In production example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was changed to 69.0 g of 4-chloro-2-nitroaniline, and other than that, the production of monoazo pigment was the same as in production example 1 151 g of D (C.I. Pigment Yellow 73) was obtained.

Production Example 5 <Preparation of Monoazo Pigment E (C. I. Pigment Yellow 105)>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was changed to 83.4 g of 6-amino-7-chloro-4-methylquinolin-2 (1H) -one, and the others Produced 164 g of monoazo pigment E (CI Pigment Yellow 105) in the same manner as in Production Example 1.
Production Example 6 <Preparation of Monoazo Pigment F (C.I. Pigment Yellow 213)>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 83.6 g of dimethyl aminoterephthalate, and 84.5 g of o-acetoacetaniside used as a coupler component was N- (7 -Methoxy-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-6-yl) -3-oxobutanamide, except that it was changed to 119 g, and in the same manner as in Production Example 1, the monoazo pigment F (C.I. Pigment Yellow 213) 198 g was obtained.

Example 1 <Preparation of Pigment Composition A>
94.0 g of monoazo pigment A (CI Pigment Yellow 74) prepared in Production Example 1 and 6.0 g of powder of monoazo pigment derivative A represented by the following general formula 9 were uniformly mixed to obtain 100 g of pigment composition A. Got. The content of the monoazo pigment derivative A in the pigment composition A was 5.0 mol%.

Example 2 <Preparation of Pigment Composition B>
94.3 g of monoazo pigment A (CI Pigment Yellow 74) prepared in Production Example 1 and 5.7 g of powder of monoazo pigment derivative B represented by the following general formula 10 were uniformly mixed to obtain 100 g of pigment composition B. Got. The content of the monoazo pigment derivative B in the pigment composition B was 5.0 mol%.

Example 3 <Preparation of Pigment Composition C>
90.0 g of monoazo pigment B (CI Pigment Yellow 1) prepared in Production Example 2 and 10.0 g of the powder of monoazo pigment derivative C represented by the following general formula 11 were uniformly mixed to obtain 100 g of pigment composition C. Got. The content of the monoazo pigment derivative C in the pigment composition C was 5.0 mol%.

Example 4 <Preparation of Pigment Composition D>
94.0 g of monoazo pigment C (CI Pigment Yellow 9) prepared in Production Example 3 and 6.0 g of powder of monoazo pigment derivative D represented by the following general formula 12 were uniformly mixed to obtain 100 g of pigment composition D. Got. The content of the monoazo pigment derivative D in the pigment composition D was 5.0 mol%.

Example 5 <Preparation of Pigment Composition E>
94.0 g of monoazo pigment D (CI Pigment Yellow 73) prepared in Production Example 4 and 6.0 g of powder of monoazo pigment derivative E represented by the following general formula 13 were uniformly mixed to obtain 100 g of pigment composition E. Got. The content of the monoazo pigment derivative E in the pigment composition E was 5.0 mol%.

Example 6 <Preparation of Pigment Composition F>
93.1 g of monoazo pigment E (CI Pigment Yellow 105) prepared in Production Example 5 and 6.9 g of powder of monoazo pigment derivative F represented by the following general formula 14 were uniformly mixed to obtain 100 g of pigment composition F. Got. The content of the monoazo pigment derivative F in the pigment composition F was 5.0 mol%.

Example 7 <Preparation of Pigment Composition G>
95.4 g of monoazo pigment F (CI Pigment Yellow 213) prepared in Production Example 6 and 4.6 g of powder of monoazo pigment derivative G represented by the following general formula 15 were uniformly mixed to obtain 100 g of pigment composition G. Got. The content of the monoazo pigment derivative G in the pigment composition G was 5.0 mol%.

Example 8 <Preparation of Pigment Composition H>
A mixture of 282.0 g of monoazo pigment A (CI Pigment Yellow 74) prepared in Production Example 1, 18.0 g of monoazo pigment derivative A represented by general formula 9, 1500 g of sodium chloride, and 250 g of diethylene glycol was made of stainless steel. A 1-gallon kneader (manufactured by Inoue Seisakusho) was used and kneaded at 60 ° C. for 6 hours to obtain a clay-like kneaded product. This kneaded product was put into 15 liters of warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. The slurry was divided into three equal parts and each was filtered through a Buchner funnel with a diameter of 285 mm. The filter was washed by sprinkling 15 liters of warm water at 50 ° C. The filter cake was taken out and added to an aqueous solution in which 250 g of 35% hydrochloric acid and 15 liters of tap water were mixed and stirred to form a slurry. After stirring for 1 hour, the slurry was divided into three equal parts, and each was filtered through a Buchner funnel having a diameter of 285 mm. Each filter was washed with 15 liters of tap water. The filter cake was taken out, added to 15 liters of ion exchange water, and stirred to form a slurry. After stirring for 1 hour, the slurry was divided into three equal parts, and each was filtered through a Buchner funnel having a diameter of 285 mm. The filter cake was washed with 15 liters of ion-exchanged water, dried and pulverized to obtain 230 g of pigment composition H. The content of the monoazo pigment derivative A in the pigment composition H was 5.0 mol%.

Example 9 <Preparation of Pigment Composition I>
A mixture of 282.0 g of monoazo pigment A (CI Pigment Yellow 74) prepared in Production Example 1, 18.0 g of monoazo pigment derivative A represented by general formula 9, 1500 g of sodium chloride, and 250 g of diethylene glycol was made of stainless steel. A 1-gallon kneader (manufactured by Inoue Seisakusho) was used and kneaded at 60 ° C. for 6 hours to obtain a clay-like kneaded product. This kneaded product was put into 15 liters of warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. The slurry was divided into three equal parts and each was filtered through a Buchner funnel with a diameter of 285 mm. The filter cake was washed with 15 liters of warm water of 50 ° C., dried and pulverized to obtain 230 g of pigment composition I. The content of the monoazo pigment derivative A in the pigment composition I was 5.0 mol%.
Example 10 <Preparation of Pigment Composition J>
Monoazo pigment A used in Example 8 (CI Pigment Yellow 74) 282.0 g to 282.8 g, monoazo pigment derivative A represented by the general formula 9 18.0 g monoazo represented by the general formula 10 Pigment composition B was changed to 17.2 g, and pigment composition J 235 g was obtained in the same manner as in Example 8 except that. The content of the monoazo pigment derivative B in the pigment composition J was 5.0 mol%.

Example 11 <Preparation of Pigment Composition K>
282.8 g of monoazo pigment A (CI Pigment Yellow 74) used in Example 9 is represented by 282.8 g, and 18.0 g of monoazo pigment derivative A represented by formula 9 is represented by formula 10. Monoazo pigment derivative B was changed to 17.2 g, and pigment composition K 235 g was obtained in the same manner as in Example 9 except that. The content of the monoazo pigment derivative B in the pigment composition K was 5.0 mol%.
Example 12 <Preparation of Pigment Composition L>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was replaced with 63.8 g of 2-methoxy-4-nitroaniline and 5.0 g of aromatic amine A represented by the following general formula 16. In the same manner as in Production Example 1 except that, 151 g of pigment composition L was obtained. The components contained in the pigment composition L are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 5.0 mol%. there were.

Example 13 <Preparation of Pigment Composition M>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was replaced with 67.1 g of 2-methoxy-4-nitroaniline and 0.050 g of aromatic amine A represented by the general formula 16. The mixture was changed to a mixture, and otherwise, in the same manner as in Production Example 1, 149 g of pigment composition M was obtained. The components contained in the pigment composition M are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 0.05 mol%. there were.
Example 14 <Preparation of Pigment Composition N>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 66.8 g of 2-methoxy-4-nitroaniline and 0.50 g of aromatic amine A represented by the general formula 16. The mixture was changed to a mixture, and otherwise, in the same manner as in Production Example 1, 150 g of pigment composition N was obtained. The components contained in the pigment composition N are the monoazo pigment A (CI Pigment Yellow 74) and the monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 0.50 mol%. there were.

Example 15 <Preparation of Pigment Composition O>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was converted to 57.1 g of 2-methoxy-4-nitroaniline and 14.9 g of aromatic amine A represented by the general formula 16. The mixture was changed to a mixture, and other than that was carried out in the same manner as in Production Example 1 to obtain 154 g of a pigment composition O. The components contained in the pigment composition O are the monoazo pigment A (CI Pigment Yellow 74) and the monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 15.0 mol%. there were.
Example 16 <Preparation of Pigment Composition P>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 47.0 g of 2-methoxy-4-nitroaniline and 29.9 g of aromatic amine A represented by the general formula 16. The mixture was changed to a mixture, and otherwise, in the same manner as in Production Example 1, 159 g of pigment composition P was obtained. The components contained in the pigment composition P are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 30.0 mol%. there were.

Example 17 <Preparation of Pigment Composition Q>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 33.6 g of 2-methoxy-4-nitroaniline and 49.8 g of aromatic amine A represented by the general formula 16. 165 g of pigment composition Q was obtained in the same manner as in Production Example 1 except that the mixture was changed to a mixture. The components contained in the pigment composition Q are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 50.0 mol%. there were.
Example 18 <Preparation of Pigment Composition R>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 63.8 g of 2-methoxy-4-nitroaniline and 4.60 g of aromatic amine B represented by the following general formula 17. In the same manner as in Production Example 1 except that, 151 g of pigment composition R was obtained. The components contained in the pigment composition R are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative B represented by the general formula 10, and the content of the monoazo pigment derivative B is 5.0 mol%. there were.

Example 19 <Preparation of Pigment Composition S>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was replaced with 67.1 g of 2-methoxy-4-nitroaniline and 0.046 g of aromatic amine B represented by the general formula 17. 149 g of pigment composition S was obtained in the same manner as in Production Example 1 except that the mixture was changed to a mixture. The components contained in the pigment composition S are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative B represented by the general formula 10, and the content of the monoazo pigment derivative B is 0.05 mol%. there were.
Example 20 <Preparation of Pigment Composition T>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was replaced with 33.6 g of 2-methoxy-4-nitroaniline and 45.6 g of aromatic amine B represented by the general formula 17. The mixture was changed to a mixture, and otherwise, in the same manner as in Production Example 1, 161 g of pigment composition T was obtained. The components contained in the pigment composition T are the monoazo pigment A (CI Pigment Yellow 74) and the monoazo pigment derivative B represented by the general formula 10, and the content of the monoazo pigment derivative B is 50.0 mol%. there were.
Example 21 <Preparation of Pigment Composition U>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as the diazo component was replaced with 53.8 g of 4-chloro-2-methylaniline and 5.20 g of aromatic amine C represented by the following general formula 18. In this mixture, 84.5 g of o-acetoacetaniside used as a coupler component was changed to 111 g of 4′-chloro-2 ′, 5′-dimethoacetacetanilide, and the same as in Production Example 1, 165 g of pigment composition U was obtained. Components contained in the pigment composition U are C.I. I. Pigment Yellow 49 and the monoazo pigment derivative H represented by the following general formula 19, and the content of the monoazo pigment derivative H was 5.0 mol%.

Example 22 <Preparation of Pigment Composition V>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 106 g of 4-amino-3-methoxy-N-phenylbenzenesulfonamide and an aromatic amine represented by the following general formula 20. D In the mixture of 7.14 g, 84.5 g of o-acetoacetanisidide used as a coupler component was changed to 111 g of 4′-chloro-2 ′, 5′-dimethoxyacetoacetanilide. Thus, 219 g of a pigment composition V was obtained. The components contained in Pigment Composition V are C.I. I. Pigment Yellow 97 and the monoazo pigment derivative I represented by the following general formula 21, and the content of the monoazo pigment derivative I was 5.0 mol%.

Example 23 <Preparation of Pigment Composition W>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 63.8 g of 2-methoxy-4-nitroaniline and 8.86 g of aromatic amine E represented by the following general formula 22. In the same manner as in Production Example 1 except that 84.5 g of o-acetoacetaniside used as a coupler component was changed to 98.6 g of 5′-chloro-2′-methoxyacetoacetanilide. 168 g of product W was obtained. Components contained in the pigment composition W are C.I. I. Pigment Yellow 111 and the monoazo pigment derivative J represented by the following general formula 23, and the content of the monoazo pigment derivative J was 5.0 mol%.

Example 24 <Preparation of Pigment Composition X>
In Production Example 1, 67.2 g of 2-methoxy-4-nitroaniline used as a diazo component was replaced with 61.6 g of 5-aminoisoindoline-1,3-dione and an aromatic amine A 4 represented by the general formula 16. In the same manner as in Production Example 1 except that 84.5 g of o-acetoacetaniside used as a coupler component was changed to 83.7 g of 2 ′, 4′-dimethylacetoacetanilide in the mixture of .98 g. 148 g of product X was obtained. Components contained in the pigment composition X are C.I. I. Pigment Yellow 167 and the monoazo pigment derivative K represented by the following general formula 24, and the content of the monoazo pigment derivative K was 5.0 mol%.

Example 25 <Preparation of Pigment Composition Y>
As diazo component A, 63.8 g of 2-methoxy-4-nitroaniline was added to 475 g of water and stirred to prepare a suspension, and ice was added to adjust the temperature to 5 ° C. or lower. 100 g of 35% -hydrochloric acid was added thereto, and the mixture was stirred for 1 hour while maintaining at 5 ° C. or lower. Then, diazotization was performed by adding an aqueous solution prepared by adding 26.6 g of sodium nitrite to 68.4 g of water and stirring for 1 hour. 0.48 g of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and an aqueous diazonium solution A was prepared.

  Similarly, as diazo component B, 5.0 g of aromatic amine A represented by general formula 16 is added to 25.0 g of water and stirred to prepare a suspension. Further, ice is added to lower the temperature to 5 ° C. or less. Adjusted. To this, 5.25 g of 35% hydrochloric acid was added and stirred for 1 hour while maintaining the temperature at 5 ° C. or lower. Then, diazotization was performed by adding an aqueous solution prepared by adding 1.40 g of sodium nitrite to 3.60 g of water and stirring for 1 hour. 0.03 g of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a diazonium aqueous solution B was prepared.

  On the other hand, 84.5 g of o-acetoacetanisid and 164 g of 25% -aqueous sodium hydroxide solution were added to 140 g of water as a coupler component, and the mixture was stirred and completely dissolved. It was poured into an aqueous solution in which 82.0 g of 80% acetic acid and 420 g of water were mixed to prepare a coupler slurry.

The coupler slurry prepared above was heated to 40 ° C., and the diazonium aqueous solution B was first dripped into it at once. The mixture was stirred at the same temperature for 10 minutes, and then the diazonium aqueous solution A was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour to complete the reaction. After completion of the reaction, the slurry was heated to 90 ° C., stirred for 1 hour, and then filtered through a Buchner funnel having a diameter of 285 mm. The filter cake was washed with 25 liters of ion-exchanged water, dried and pulverized to obtain 150 g of pigment composition Y. The components contained in the pigment composition Y are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative A represented by the general formula 9, and the content of the monoazo pigment derivative A is 5.0 mol%. there were.
Example 26 <Preparation of Pigment Composition Z>
In Example 25, 5.0 g of the aromatic amine A represented by the general formula 16 used as the diazo component B was changed to 4.60 g of the aromatic amine B represented by the general formula 17; In the same manner as in No. 25, 150 g of pigment composition Z was obtained. The components contained in the pigment composition Z are a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative B represented by the general formula 10, and the content of the monoazo pigment derivative B is 5.0 mol%. there were.

Example 27 <Preparation of Pigment Composition a>
As a diazo component, 63.8 g of 2-methoxy-4-nitroaniline was added to 475 g of water and stirred to prepare a suspension, and ice was added to adjust the temperature to 5 ° C. or lower. 100 g of 35% -hydrochloric acid was added thereto, and the mixture was stirred for 1 hour while maintaining at 5 ° C. or lower. Then, diazotization was performed by adding an aqueous solution prepared by adding 26.6 g of sodium nitrite to 68.4 g of water and stirring for 1 hour. 0.48 g of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a diazonium aqueous solution was prepared. 9.37 g of the monoazo pigment derivative A represented by the general formula 9 was added thereto, and the mixture was stirred uniformly to obtain a suspension, thereby obtaining a diazonium aqueous solution containing the monoazo pigment derivative A.

  On the other hand, 80.4 g of o-acetoacetanisid and 156 g of 25% -aqueous sodium hydroxide solution were added to 140 g of water as a coupler component, and the mixture was stirred and completely dissolved. This was poured into an aqueous solution in which 420 g of water and 78.0 g of 80% -acetic acid were mixed to prepare a coupler slurry.

  The coupler slurry prepared above was heated to 40 ° C., and a diazonium aqueous solution containing the monoazo pigment derivative A was dropped therein over 1 hour. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour to complete the reaction. After completion of the reaction, the slurry was heated to 90 ° C., stirred for 1 hour, and then filtered through a Buchner funnel having a diameter of 285 mm. The filter cake was washed with 25 liters of ion-exchanged water, dried and pulverized to obtain 150 g of pigment composition a. The components contained in the pigment composition a were a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative A, and the content of the monoazo pigment derivative A was 5.0 mol%.

Example 28 <Preparation of Pigment Composition b>
In the same manner as in Example 27, 9.37 g of the monoazo pigment derivative A represented by the general formula 9 used in Example 27 was changed to 8.95 g of the monoazo pigment derivative B represented by the general formula 10. 150 g of pigment composition b was obtained. The components contained in the pigment composition b were a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative B, and the content of the monoazo pigment derivative B was 5.0 mol%.
Example 29 <Preparation of Pigment Composition c>
In Example 27, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 65.5 g of 4-chloro-2-nitroaniline, and 80.4 g of o-acetoacetaniside used as a coupler component. 2'-chloroacetoacetanilide was changed to 82.1 g, and monoazo pigment derivative A 9.37 g represented by general formula 9 was changed to monoazo pigment derivative L 11.4 g represented by general formula 25 below, Except for this, in the same manner as in Example 27, 156 g of pigment composition c was obtained. Components contained in the pigment composition c are C.I. I. Pigment Yellow 3 and the monoazo pigment derivative L represented by the following general formula 25, and the content of the monoazo pigment derivative L was 5.0 mol%.

Example 30 <Preparation of Pigment Composition d>
In Example 27, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 65.5 g of 4-chloro-2-nitroaniline, and 80.4 g of o-acetoacetaniside used as a coupler component. Example 6 Example 6 Example 6 Example 1 Example Acetoacetanilide was changed to 6.8.7 g, and monoazo pigment derivative A 9.37 g represented by general formula 9 was changed to monoazo pigment derivative M 8.18 g represented by general formula 26 below. In the same manner as in No. 27, 140 g of pigment composition d was obtained. Components contained in the pigment composition d are C.I. I. Pigment Yellow 6 and the monoazo pigment derivative M represented by the following general formula 26, and the content of the monoazo pigment derivative M was 5.0 mol%.

Example 31 <Preparation of Pigment Composition e>
In Example 27, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 52.1 g of 2-aminobenzoic acid, and 80.4 g of o-acetoacetaniside used as a coupler component was 5-acetoacetamide. -2-benzimidazolinone was changed to 90.4 g, and monoazo pigment derivative A 9.37 g represented by the general formula 9 was changed to 13.8 g monoazo pigment derivative N represented by the following general formula 27, Otherwise in the same manner as in Example 27, 153 g of a pigment composition e was obtained. Components contained in the pigment composition e are C.I. I. Pigment Yellow 151 and the monoazo pigment derivative N represented by the following general formula 27, and the content of the monoazo pigment derivative N was 5.0 mol%.

Example 32 <Preparation of Pigment Composition f>
In Example 27, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 79.4 g of dimethyl aminoterephthalate, and 80.4 g of o-acetoacetaniside used as a coupler component was 5-acetoacetamide- 2-benzimidazolinone was changed to 90.4 g, and monoazo pigment derivative A 9.37 g represented by the general formula 9 was changed to 11.0 g monoazo pigment derivative O represented by the following general formula 28, respectively. In the same manner as in Example 27, to obtain 177 g of a pigment composition f. The components contained in the pigment composition f are C.I. I. Pigment Yellow 175 and the monoazo pigment derivative O represented by the following general formula 28, and the content of the monoazo pigment derivative O was 5.0 mol%.

Example 33 <Preparation of Pigment Composition g>
As a diazo component, 63.8 g of 2-methoxy-4-nitroaniline was added to 475 g of water and stirred to prepare a suspension, and ice was added to adjust the temperature to 5 ° C. or lower. 100 g of 35% -hydrochloric acid was added thereto, and the mixture was stirred for 1 hour while maintaining at 5 ° C. or lower. Then, diazotization was performed by adding an aqueous solution prepared by adding 26.6 g of sodium nitrite to 68.4 g of water and stirring for 1 hour. 0.48 g of sulfamic acid was added to the reaction mixture to eliminate nitrous acid, and a diazonium aqueous solution was prepared.

  On the other hand, 80.4 g of o-acetoacetaniside and 156 g of 25% -sodium hydroxide aqueous solution were added to 140 g of water as a coupler component and stirred to completely dissolve, thereby preparing a coupler aqueous solution. Also, 420 g of water, 78.0 g of 80% acetic acid, and 9.37 g of the monoazo pigment derivative A represented by the general formula 9 were mixed to prepare a suspension of the monoazo pigment derivative A. Into that, the coupler aqueous solution prepared above was injected to prepare a coupler slurry containing the monoazo pigment derivative A.

  The coupler slurry containing the monoazo pigment derivative A prepared above was heated to 40 ° C., and a diazonium aqueous solution was dropped therein over 1 hour. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour to complete the reaction. After completion of the reaction, the slurry was heated to 90 ° C., stirred for 1 hour, and then filtered through a Buchner funnel having a diameter of 285 mm. The filter cake was washed with 25 liters of ion-exchanged water, dried and pulverized to obtain 150 g of a pigment composition g. The components contained in pigment composition g were monoazo pigment A (CI Pigment Yellow 74) and monoazo pigment derivative A, and the content of monoazo pigment derivative A was 5.0 mol%.

Example 34 <Preparation of Pigment Composition h>
In the same manner as in Example 33, 9.37 g of the monoazo pigment derivative A represented by the general formula 9 used in Example 33 was changed to 8.95 g of the monoazo pigment derivative B represented by the general formula 10. The pigment composition h 150g was obtained. The components contained in the pigment composition h were the monoazo pigment A (CI Pigment Yellow 74) and the monoazo pigment derivative B, and the content of the monoazo pigment derivative B was 5.0 mol%.
Example 35 <Preparation of Pigment Composition i>
In Example 33, 63.8 g of 2-methoxy-4-nitroaniline used as the diazo component was added to 52.4 g of 4-nitroaniline, and 80.4 g of o-acetoacetaniside used as the coupler component was acetoacetanilide 68. 8 g, and 9.37 g of the monoazo pigment derivative A represented by the general formula 9 was changed to 8.12 g of the monoazo pigment derivative P represented by the following general formula 29, respectively. Thus, 127 g of pigment composition i was obtained. The components contained in the pigment composition i are C.I. I. Pigment Yellow 4 and the monoazo pigment derivative P represented by the following general formula 29, and the content of the monoazo pigment derivative P was 5.0 mol%.

Example 36 <Preparation of Pigment Composition j>
In Example 33, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 79.4 g of dimethyl 5-aminoisophthalate, and 80.4 g of o-acetoacetaniside used as a coupler component was 5- Acetoacetamide-2-benzimidazolinone 90.5 g, and monoazo pigment derivative A 9.37 g represented by general formula 9 were changed to monoazo pigment derivative Q 9.89 g represented by general formula 30 below, respectively. Otherwise in the same manner as in Example 33, 176 g of a pigment composition j was obtained. Components contained in the pigment composition j are C.I. I. Pigment Yellow 120 and the monoazo pigment derivative Q represented by the following general formula 30 and the content of the monoazo pigment derivative Q was 5.0 mol%.

Example 37 <Preparation of Pigment Composition k>
In Example 33, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 61.1 g of 2- (trifluoromethyl) aniline, and 80.4 g of o-acetoacetaniside used as a coupler component. 5-acetoacetamide-2-benzimidazolinone was changed to 90.5 g, and monoazo pigment derivative A 9.37 g represented by general formula 9 was changed to monoazo pigment derivative R 12.7 g represented by general formula 31 below, respectively. Otherwise, in the same manner as in Example 33, 161 g of pigment composition k was obtained. Components contained in the pigment composition k are C.I. I. Pigment Yellow 154 and the monoazo pigment derivative R represented by the following general formula 31, and the content of the monoazo pigment derivative R was 5.0 mol%.

Example 38 <Preparation of Pigment Composition l>
In Example 33, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 46.8 g of o-anisidine, and 80.4 g of o-acetoacetaniside used as a coupler component was 5-acetoacetamide-2. -90.5 g of benzimidazolinone, and 9.37 g of the monoazo pigment derivative A represented by the general formula 9 were changed to 10.4 g of the monoazo pigment derivative S represented by the following general formula 32, respectively. In the same manner as in Example 33, 145 g of a pigment composition l was obtained. The components contained in the pigment composition l are C.I. I. Pigment Yellow 194 and the monoazo pigment derivative S represented by the following general formula 32, and the content of the monoazo pigment derivative S was 5.0 mol%.

Example 39 <Preparation of Pigment Composition m>
As a diazo component, 63.8 g of 2-methoxy-4-nitroaniline was added to 475 g of water and stirred to prepare a suspension, and ice was added to adjust the temperature to 5 ° C. or lower. 100 g of 35% -hydrochloric acid was added thereto, and the mixture was stirred for 1 hour while maintaining at 5 ° C. or lower. Then, diazotization was performed by adding an aqueous solution prepared by adding 26.6 g of sodium nitrite to 68.4 g of water and stirring for 1 hour. To the reaction mixture, 0.48 g of sulfamic acid was added to eliminate nitrous acid, and water was further added to adjust the liquid volume to 1000 g to prepare a diazonium aqueous solution.

  On the other hand, 80.4 g of o-acetoacetanisid and 156 g of 25% -sodium hydroxide aqueous solution were added to 140 g of water as a coupler component and stirred to dissolve completely, and further water was added to adjust the liquid volume to 400 g. A coupler aqueous solution was prepared.

  A reaction tank aqueous solution was prepared by uniformly mixing 365 g of water, 64.0 g of 80% acetic acid, and 71.2 g of 25% sodium hydroxide aqueous solution. 9.37 g of monoazo pigment derivative A represented by the general formula 9 was added thereto and stirred uniformly to obtain a suspension. It was heated to 40 ° C., and while maintaining the temperature, the diazonium aqueous solution and the coupler aqueous solution were simultaneously added dropwise over 1 hour while maintaining the pH of the reaction vessel at 6.0 or lower. After completion of dropping, the mixture was stirred at 40 ° C. for 1 hour to complete the reaction. After completion of the reaction, the slurry was heated to 90 ° C., stirred for 1 hour, and then filtered through a Buchner funnel having a diameter of 285 mm. The filter cake was washed with 25 liters of ion-exchanged water, dried and pulverized to obtain 151 g of a pigment composition m. The components contained in pigment composition m were monoazo pigment A (CI Pigment Yellow 74) and monoazo pigment derivative A, and the content of monoazo pigment derivative A was 5.0 mol%.

Example 40 <Preparation of Pigment Composition n>
In the same manner as in Example 39, 9.37 g of the monoazo pigment derivative A represented by the general formula 9 used in Example 39 was changed to 8.95 g of the monoazo pigment derivative B represented by the general formula 10. 150 g of pigment composition n was obtained. The components contained in the pigment composition n were a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative B, and the content of the monoazo pigment derivative B was 5.0 mol%.
Example 41 <Preparation of Pigment Composition o>
In Example 39, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 65.5 g of 4-chloro-2-nitroaniline, and 80.4 g of o-acetoacetaniside used as a coupler component. Changed to 79.6 g of 2 ′, 4′-dimethylacetoacetanilide and 9.37 g of monoazo pigment derivative A represented by general formula 9 to 9.33 g of monoazo pigment derivative T represented by general formula 33 below Otherwise, in the same manner as in Example 39, 152 g of a pigment composition o was obtained. Components contained in the pigment composition o are C.I. I. Pigment Yellow 2 and the monoazo pigment derivative T represented by the following general formula 33, and the content of the monoazo pigment derivative T was 5.0 mol%.

Example 42 <Preparation of Pigment Composition p>
In Example 39, 63.8 g of 2-methoxy-4-nitroaniline used as the diazo component was added to 52.4 g of 2-nitroaniline, and 80.4 g of o-acetoacetaniside used as the coupler component was acetoacetanilide 68. 8 g, and 9.37 g of the monoazo pigment derivative A represented by the general formula 9 was changed to 7.86 g of the monoazo pigment derivative U represented by the following general formula 34, respectively. As a result, 128 g of a pigment composition p was obtained. Components contained in the pigment composition p are C.I. I. Pigment Yellow 5 and the monoazo pigment derivative U represented by the following general formula 34, and the content of the monoazo pigment derivative U was 5.0 mol%.

Example 43 <Preparation of Pigment Composition q>
In Example 39, 63.8 g of 2-methoxy-4-nitroaniline used as a diazo component was added to 65.5 g of 4-chloro-2-nitroaniline, and 80.4 g of o-acetoacetaniside used as a coupler component. To 87.6 g of 4′-chloro-2′-methylacetoacetanilide, 9.37 g of monoazo pigment derivative A represented by general formula 9 is converted to 11.8 g of monoazo pigment derivative V represented by general formula 35 below. Each was changed, and otherwise, it carried out similarly to Example 39, and obtained 162 g of pigment compositions q. Components contained in the pigment composition q are C.I. I. Pigment Yellow 98 and the monoazo pigment derivative V represented by the following general formula 35, and the content of the monoazo pigment derivative V was 5.0 mol%.

Example 44 <Preparation of Pigment Composition r>
In Example 39, 63.8 g of 2-methoxy-4-nitroaniline used as the diazo component was changed to 57.7 g of 4-methyl-2-nitroaniline, and 9.37 g of the monoazo pigment derivative A represented by the general formula 9 was added. In the same manner as in Example 39, except for changing to monoazo pigment derivative W 13.2 g represented by the following general formula 36, pigment composition r 149 g was obtained. Components contained in the pigment composition r are C.I. I. Pigment Yellow 203 and the monoazo pigment derivative W represented by the following general formula 36, and the content of the monoazo pigment derivative W was 5.0 mol%.

<Evaluation of various monoazo pigments and various pigment compositions>
For the monoazo pigments and pigment compositions prepared in Production Examples 1 to 6 and Examples 1 to 44, the average primary particle size, the specific conductivity of the extracted water, and the metal content were measured by the following methods. The results are summarized in Table 3.

(Average primary particle size)
The average primary particle size was measured from a photograph of pigment particle size taken with a scanning electron microscope. A scanning electron microscope (manufactured by JEOL Datum Co., Ltd., JSM) was prepared by applying a conductive double-sided tape to a metal sample stage, attaching a pigment or pigment composition, and depositing platinum on the sample surface by sputtering. Particles were photographed with a −6700F scanning electron microscope), and the maximum diameter was measured for each of the 100 primary particles of the pigment photographed in the same field of view. A value obtained by averaging them was calculated, and the value was defined as an average primary particle size.
(Specific conductivity of extracted water)
5 g of various monoazo pigments or pigment compositions were moistened with 10 g of ethanol, and 90 g of ion exchange water was further added to form a slurry. While stirring with a magnetic stirrer, the mixture was boiled and stirred for 5 minutes. After completion of stirring, the mixture was cooled to room temperature, and ion-exchanged water was added so that the total amount of slurry was 105 g. The slurry was stirred uniformly and filtered through 5 C filter paper defined by JIS P 3801. The container for receiving the filtrate was rinsed with the filtrate, filled with the filtrate, and the specific conductivity was measured with an electric conductivity meter (CM-40V, manufactured by Toa DKK Corporation).
(Metal content)
About 2 g of various monoazo pigments or pigment compositions were added to 8 ml of nitric acid, and treated with a microwave sample pretreatment device (ETHOS1 manufactured by Milestone General Co., Ltd.) according to the temperature program shown in Table 1.

  After the treatment solution was cooled to room temperature, 2 ml of nitric acid was added, and the treatment was further carried out according to the temperature program shown in Table 2.

  The treatment liquid was filtered through 5 types C filter paper defined by JIS P 3801, and the filtrate was measured in a 50 ml volumetric flask to obtain a measurement sample.

The measurement sample was measured with a multi-ICP emission spectroscopic analyzer (manufactured by Varian Technologies Japan Limited, 720-ES type), and each metal element was quantified.

<Preparation of various pigment dispersions>
(Preparation of oil-based pigment dispersion)
Examples 45-68 and Comparative Examples 1-3
1000 g of various pigment compositions or various monoazo pigments, 325 g of Disperbyk130 (manufactured by BYK Chemie, pigment dispersant), 250 g of Joncrill 586 (manufactured by BASF Japan, styrene-acrylic resin), 925 g of ethylene glycol monobutyl ether acetate, The mixture was stirred with a high speed mixer until uniform. It was dispersed for 2 hours with a horizontal wet disperser (DYNO-MILL TYPE KDL-PILOT), and then 2500 g of ethylene glycol monobutyl ether acetate was added and further dispersed for 1 hour to obtain oil pigment dispersions A to Z and a. . Table 4 summarizes the pigment composition or monoazo pigment used in each oil pigment dispersion.
Comparative Example 4
Various pigment compositions or various monoazo pigments were changed to Hansa Brilliant Yellow 5GX (manufactured by Clariant, CI Pigment Yellow 74), and the other oily pigments were the same as in Examples 45 to 68 and Comparative Examples 1 to 3. Dispersion b was obtained.
(Preparation of aqueous pigment dispersion)
Examples 69-88 and Comparative Examples 5-7
1000 g of various pigment compositions or various monoazo pigments, Jonkrill HPD-96J (manufactured by BASF, styrene-acrylic resin, active ingredient 34.0%) 735 g, Surfynol 104E (manufactured by Air Products and Chemicals, defoaming agent) 50% of active ingredients), 50 g of Revanax BX-150 (manufactured by Shoei Chemical Co., Ltd., preservative), 250 g of propylene glycol and 415 g of ion-exchanged water were mixed and stirred with a high speed mixer until uniform. It was dispersed for 2 hours with a horizontal wet disperser (DYNO-MILL TYPE KDL-PILOT), and then 2500 g of ion-exchanged water was added and further dispersed for 1 hour to obtain aqueous pigment dispersions A to W. The pigment compositions or monoazo pigments used for each aqueous pigment dispersion are summarized in Table 5.
Comparative Example 8
Various pigment compositions or various monoazo pigments were changed to Hansa Brilliant Yellow 5GX (manufactured by Clariant, CI Pigment Yellow 74), and oily pigment dispersion X was obtained in the same manner as in Examples 69 to 88 and Comparative Examples 5 to 7. Got.
<Evaluation of various pigment dispersions>
For each dispersion, the dispersion particle size, viscosity, crystal stability and storage stability were evaluated by the following methods. The results are summarized in Table 4 and Table 5.
(Dispersed particle size)
Dispersed particle diameter was evaluated by _{D 50} values measured by Microtrac UPA-0.99 (manufactured by Nikkiso Co., Ltd.).
(viscosity)
The viscosity was measured with a B-type viscometer VISCOMETER (manufactured by Toki Sangyo Co., Ltd.) at 60 rpm.
(Crystal stability)
As an index of crystal stability, a photograph of the pigment or pigment composition particles in each pigment dispersion was taken with a transmission electron microscope.

  Particles were photographed with a transmission electron microscope (H-7650 type transmission electron microscope, manufactured by Hitachi High-Technologies Corporation) using a sample obtained by dripping and drying various pigment dispersions on a mesh with a support film. The maximum diameter was measured for 100 primary particles of the pigment photographed in the field of view. A value obtained by averaging them was calculated, and the value was defined as an average primary particle size.

Each dispersion was sealed in a screw cap bottle and stored at 70 ° C. for 4 weeks, and the same measurement was performed. Crystal stability was evaluated by the change in average primary particle size before and after storage. Before and after storage, the change rate of the average primary particle size was determined as 0, 15% exceeding 30% and 30% or less, and exceeding 30% as X.
(Storage stability)
Each dispersion was sealed in a screw cap bottle and stored at 70 ° C. for 4 weeks, and then the dispersed particle size and viscosity were measured. Storage stability was evaluated based on changes in the dispersed particle diameter and viscosity before and after storage, and the presence or absence of sediment after storage.

  As shown in Table 4, the oil-based pigment dispersion of the present invention gave a dispersion having a lower viscosity and a smaller dispersed particle size than the others, and showed good dispersibility. These dispersions were good both in storage stability and crystal stability.

As shown in Table 5, the aqueous pigment dispersion of the present invention gave a dispersion having a lower viscosity and a smaller dispersed particle size than the others, and showed good dispersibility. These dispersions were good both in storage stability and crystal stability.
<Preparation of various ink-jet inks>
(Preparation of oil-based inkjet ink)
Examples 89-112 and Comparative Examples 9-12
25.0 g of the oily pigment dispersion prepared in Examples 45 to 68 and Comparative Examples 1 to 4, 10.0 g of propylene glycol monomethyl ether acetate, 55.0 g of ethylene glycol monobutyl ether acetate, and 10.0 g of diethylene glycol monoethyl ether acetate were mixed. And after stirring for 1 hour, it filtered with the PTFE membrane filter with a hole diameter of 1.0 micrometer, and obtained oil-based inkjet ink AZ and ab.
(Preparation of water-based inkjet ink)
Examples 113 to 132 and Comparative Examples 13 to 16
Aqueous pigment dispersions 15.0 g prepared in Examples 69 to 88 and Comparative Examples 5 to 8, acrylic resin emulsion W-215 (manufactured by Nippon Polymer Kogyo Co., Ltd., solid content 30%) 1.5 g, ethylene glycol 15.0 g Then, 68.5 g of ion-exchanged water was mixed and stirred for 1 hour, and then filtered through a PTFE membrane filter having a pore size of 1.0 μm to obtain aqueous inkjet inks A to X.
<Evaluation of various ink-jet inks>
(Evaluation of oil-based inkjet ink)
The dischargeability of each oil-based inkjet ink by a printer and the coloring power of the obtained printed matter were evaluated. The results are summarized in Table 6.

  In the evaluation of ejection properties, each oil-based ink-jet ink was filled in a cartridge of an ink-jet printer IP-6500 (manufactured by Seiko Eye Infotech Co., Ltd.) and printed on a glossy PVC sheet MD5 (manufactured by Metamark). The printed matter was visually observed for the presence or absence of missing dots (portions where printing was not performed), and used as an index of ejection properties. When the nozzles of the printer head where dot missing occurred were 0% of all nozzles, it was judged as ○, when 0-5%, Δ when exceeding 5%, and x.

In the evaluation of coloring power, for each printed matter, the reflection density of a portion where no dot omission occurred was measured with a reflection densitometer D19C (manufactured by Gretag Machbeth). On the basis of the oil-based inkjet ink b prepared in Comparative Example 12, the equivalent was determined as Δ, the higher reflection density as ○, and the lower as ×.
(Evaluation of water-based inkjet ink)
The ejectability of each water-based inkjet ink by a printer and the coloring power of the obtained printed matter were evaluated. The results are summarized in Table 7.

  In the evaluation of ejection performance, each water-based inkjet ink was filled in a cartridge of an inkjet printer HG-5130 (manufactured by Seiko Epson Corporation) and printed on photographic paper / glossy gold (manufactured by Canon Inc.). The printed matter was visually observed for the presence or absence of missing dots (portions where printing was not performed), and used as an index of ejection properties. When the nozzles of the printer head where dot missing occurred were 0% of all nozzles, it was judged as ○, when 0-5%, Δ when exceeding 5%, and x.

  In the evaluation of coloring power, the reflection density of a portion where no dot omission occurred in each printed matter was measured with a reflection densitometer D19C (manufactured by Gretag Machbeth). On the basis of the water-based inkjet ink X prepared in Comparative Example 16, it was determined that the equivalent was Δ, the higher reflection density was ◯, and the lower was X.

  As shown in Table 6, the oil-based inkjet ink of the present invention had better ejection properties and coloring power than the others.

As shown in Table 7, the oil-based ink-jet ink of the present invention had better ejection properties and coloring power than the others.

Claims (12)

A pigment composition containing a compound represented by the following general formula 1 and a compound represented by the following general formula 2.

(In formula, m, n, and p represent the integer of 1-3.
X ₁ is a hydrogen atom, is an alkyl group of 1 to 5 carbon atoms, a halogen atom, an alkoxyl group having 1 to 5 carbon atoms, an acetylamino group, a carboxyl group, a sulfone group (two X ₁ is integrated, further And may form a heterocyclic structure which may be substituted, including a nitrogen atom, an oxygen atom or a sulfur atom.
X ₂ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a nitro group, a halogen atom, a sulfone group, an alkoxyl group having 1 to 5 carbon atoms, a carbamoyl group, a sulfamoyl group, an ester having 1 to 5 carbon atoms, a carboxyl group, Represents a trifluoromethyl group (two X ₂ may be combined to form an optionally substituted heterocyclic structure containing an additional nitrogen atom, oxygen atom or sulfur atom).
X ₃ represents either a group represented by X ₂ or a group represented by the following general formula 3 or the following general formula 4.
However, at least one of X ₃ is either a group represented by the following general formula 3 or the following general formula 4. )

(Wherein, _{X 4 is, -SO 2 NR '-, -} CONR'- represents either.
X ₅ is a direct bond connecting X ₄ and X ₆ , an optionally substituted alkylene group having 20 or less carbon atoms, an optionally substituted alkenylene group having 20 or less carbon atoms, Represents any of an arylene group which may have a substituent and has 20 or less carbon atoms (these groups are divalent selected from —NR′—, —O—, —SO ₂ — or —CO—); And may be bonded to each other via a linking group.
X ₆ represents any of a hydrogen atom, —OR ₁ , —NR ₁ R ₂ , —CONR ₁ R ₂ , —SO ₂ NR ₁ R ₂ , and —COOR ₁ .
However, R ′ may have a hydrogen atom, a substituent, an alkyl group having 20 or less carbon atoms, an optionally substituted substituent, an alkenyl group having 20 or less carbon atoms, or a substituent. Or an aryl group having 20 or less carbon atoms.
R ₁ and R ₂ each independently have a hydrogen atom, a substituent, which may have a substituent, an alkyl group having 20 or less carbon atoms, an optionally substituted alkenyl group, which has 20 or less carbon atoms, It represents any of an aryl group which may have a substituent and has 20 or less carbon atoms. R ₁ and R ₂ together may contain an additional nitrogen atom, oxygen atom or sulfur atom, and may form an optionally substituted heterocyclic structure.
R ′ or R ₁ or R ₂ and X ₅ may be combined to form an optionally substituted heterocyclic structure which may contain an additional nitrogen atom, oxygen atom or sulfur atom. )

(In the formula, X ₇ represents —NR′— or —O—.
X ₈ and X ₉ each independently represent any of a group represented by the following general formula 5, —OR ′, —NR ′ ₂ , and a halogen atom.
However, R ′ represents the one defined by the general formula 3. )

(In the formula, X ₅ , X ₆ and X ₇ are those defined by General Formula 3 and General Formula 4)   The content of the compound represented by General Formula 2 is 0.1 to 40 mol% of the total amount of the number of moles of the compound represented by General Formula 1 and the number of moles of the compound represented by General Formula 2. The pigment composition according to claim 1. In a method for producing a pigment for diazotizing various aromatic amines and then coupling with various acetoacetanilide compounds, a mixture of a compound represented by the following general formula 6 and a compound represented by the following general formula 7 is used as the aromatic amine The pigment composition according to claim 1, which is obtained by reacting with an acetoacetanilide compound represented by the following general formula 8:

(In the formula, m, n, p, X ₁ , X ₂ , and X ₃ represent those defined by General Formula 1 and General Formula 2, respectively.)   In the method for producing a pigment which is diazotized with various aromatic amines and then coupled with various acetoacetanilide compounds, after the aromatic amine diazotized compound represented by general formula 6 and the compound represented by general formula 2 are mixed, The pigment composition of Claim 1 or 2 obtained by making it react with the acetoacetanilide compound represented by General formula 8.   In a method for producing a pigment that is coupled with various acetoacetanilide compounds after diazotization of various aromatic amines, after mixing the acetoacetanilide compound represented by general formula 8 with the compound represented by general formula 2, The pigment composition of Claim 1 or 2 obtained by making it react with the diazotized product of the aromatic amine represented by these.   In a method for producing a pigment that is coupled with various acetoacetanilide compounds after diazotization of various aromatic amines, it is represented by the general formula 6 in a buffer solution of pH 3-6 containing the compound represented by the general formula 2. The pigment composition according to claim 1, which is obtained by simultaneously adding a diazotized aromatic amine and a basic aqueous solution of an acetoacetanilide compound represented by the general formula 8 at a constant flow rate.   The pigment composition according to any one of claims 1 to 6, wherein the average primary particle diameter is 200 nm or less.   The pigment composition according to any one of claims 1 to 7, wherein the specific conductivity of the aqueous solution obtained by boiling and extracting the pigment composition with ion-exchanged water is less than 200 µS / cm.   The pigment composition according to any one of claims 1 to 8, wherein the total content of calcium, magnesium, and iron is less than 300 ppm.   The pigment composition according to any one of claims 1 to 8, wherein the contents of calcium, magnesium, and iron are each less than 150 ppm.   The pigment dispersion containing the pigment composition of any one of Claims 1-10. The inkjet ink containing the pigment composition of any one of Claims 1-10.