JP2002201377A - Pigment composition and pigment dispersion - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a stable pigment composition or pigment dispersion excellent in non-aggegativeness and fluidity and suitable for offset inks, gravure inks, coatings, ink-jet inks and the like. SOLUTION: This pigment composition is characterized by comprising at least one compound selected from basic group-containing pigment derivatives, basic group-containing anthraquinone derivatives and basic group-containing triazine derivatives, a sulfo-containing resin and a pigment.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pigment composition and a pigment dispersion which are excellent in usability, in particular, non-aggregation and fluidity.

[0002]

2. Description of the Related Art In general, when fine pigment particles are dispersed in vehicles such as offset inks, gravure inks, and paints, it is difficult to obtain a stable dispersion, and there are various reasons for the production work and the value of the obtained product. It is known to cause problems.

For example, a dispersion containing a pigment composed of fine particles often exhibits a high viscosity, which makes it difficult not only to take out and transport the product from the dispersing machine but also to worsen the gelation during storage. And it may be difficult to use.
Further, with respect to the surface of the coated film of the colored product, a state defect such as a decrease in gloss and a leveling defect may occur. When different kinds of pigments are mixed and used, color unevenness and a remarkable decrease in coloring power may appear in the developed product due to phenomena such as color separation due to aggregation and sedimentation.

In order to solve the above-mentioned various problems, a method of mixing a pigment derivative having an organic pigment as a parent skeleton and having an acidic group or a basic group as a substituent in a side chain as a dispersant is disclosed in 41-2466, USP285540
3, JP-A-63-305173, JP-A-1-24746
8, proposed in JP-A-3-26767. In these inventions, a mechanism is considered in which the pigment derivative and the resin component in the varnish interact to contribute to dispersion stabilization.
Since there are so many varnishes in paints and inks, pigment derivatives and resins in the varnish do not always work effectively, and satisfactory effects are obtained except for some varnishes. There is no actual situation.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides a stable pigment composition and a pigment dispersion excellent in non-aggregation and fluidity suitable for offset ink, gravure ink, paint, ink jet ink and the like.

[0006]

The present invention provides a pigment derivative having a basic group, an anthraquinone derivative having a basic group or a triazine derivative having a basic group, a resin having a sulfonic acid group, The present invention relates to a pigment composition comprising a pigment.

The sulfonic acid group contained in the resin having a sulfonic acid group of the present invention may be a metal such as sodium or potassium or diethylamine, dibutylamine, triethanolamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, octylamine. A salt may be formed with an organic amine such as amine, dodecylamine, stearylamine, oleylamine, and distearylamine.

[0008] Examples of the resin having a sulfonic acid group include a vinyl polymer containing an ethylenically unsaturated monomer having a sulfonic acid group as a monomer component.

Examples of the ethylenically unsaturated monomer having a sulfonic acid group include 2-acrylamido-2-methylpropanesulfonic acid, vinylsulfonic acid, and 3-allyloxy-2.
Sodium, potassium such as -hydroxypropanesulfonic acid, p-styrenesulfonic acid, methallylsulfonic acid, allylsulfonic acid, methallyloxybenzenesulfonic acid, allyloxybenzenesulfonic acid, 2-sulfoethyl methacrylate, and 4-sulfobutyl methacrylate; ,
Examples thereof include alkali metal salts such as lithium, ammonium salts, amine salts, and polyvalent metal salts such as calcium, magnesium, aluminum, and zinc.

[0010] These ethylenically unsaturated monomers having a sulfonic acid group can be used alone or in combination of two or more. The copolymerization ratio of the monomer having a sulfonic acid group in the copolymer is 100
The amount is preferably from 0.1 to 30 parts by weight, more preferably from 0.1 to 5 parts by weight, based on part by weight.

The weight average molecular weight (Mw) of the sulfonic acid group-containing resin of the present invention is preferably from 1,000 to 50,000.
And more preferably 2,000 to 30,000.

The resin having a sulfonic acid group is as follows:
It can be obtained by radical polymerization of an ethylenically unsaturated monomer having a sulfonic acid group and an ethylenically unsaturated monomer having no sulfonic acid group.

Specific examples of the ethylenically unsaturated monomer having no sulfonic acid group include methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate,
Butyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, stearyl methacrylate,
Alkyl (meth) acrylates such as cyclohexyl methacrylate, styrene, α-methylstyrene,
Vinyl toluene, vinyl acetate, vinyl propionate acrylic acid, acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, monohydroxyethyl phthalate, ω-carboxy-polycaprolactone monoacrylate, maleic acid, itaconic acid, fumaric acid, glutacon Acid, tetrahydrophthalic acid, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate , 2-
Hydroxybutyl (meth) acrylate, glycerin (meth) acrylate, polyethylene glycol mono (meth) acrylate (n = 2 to 50), polycaprolactone-modified hydroxyethyl (meth) acrylate (n
= 1 to 6), epoxy (meth) acrylate, hydroxyl-terminated urethane (meth) acrylate, and the like. These can be used alone or in combination of two or more.

The resin having a sulfonic acid group is carried out at 50 to 150 ° C. for 2 to 10 hours under an inert gas stream in the presence of an initiator. If necessary, the reaction may be performed in the presence of a solvent.

Examples of the initiator include organic peroxides such as benzoyl peroxide, cumene hydroperoxide, t-butyl hydroperoxide, diisopropyl peroxycarbonate, di-t-butyl peroxide and t-butyl peroxybenzoate. And azo compounds such as 2'-azobisisobutyronitrile. The initiator is preferably used in an amount of 1 to 20 parts by weight based on 100 parts by weight of the ethylenically unsaturated monomer.

It is preferable to use water and / or a water-miscible organic solvent as the solvent. Water-miscible organic solvents include ethyl alcohol, isopropyl alcohol,
Examples thereof include alcohol solvents such as n-propyl alcohol, and mono or dialkyl ethers of ethylene glycol or diethylene glycol.

The pigment derivative, anthraquinone derivative or triazine derivative having a basic group constituting the present invention is represented by the following general formulas (1), (2), (3) and (4)
Having at least one substituent selected from the group consisting of: Equation (1)

[0018]

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Equation (2)

[0020]

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Equation (3)

[0022]

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Equation (4)

[0024]

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X: -SO _2- , -CO-, -CH ₂ NHC
OCH ₂ —, —CH ₂ — or a direct bond. n represents an integer of 1 to 10. R _1, R _2: each independently, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group or further together with R ₁ and R _2, Represents an optionally substituted heterocycle containing a nitrogen, oxygen or sulfur atom. The alkyl group and the alkenyl group preferably have 1 to 10 carbon atoms. R _{3 represents} an alkyl group which may be substituted, an alkenyl group which may be substituted or a phenyl group which may be substituted. The alkyl group and the alkenyl group preferably have 1 to 10 carbon atoms. R ₄ , R ₅ , R ₆ , and R ₇ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group. The alkyl group and the alkenyl group preferably have 1 to 5 carbon atoms. _{Y: -NR 8 -Z-NR 9} - or a direct bond. R ₈ and R ₉ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group. The alkyl group and the alkenyl group preferably have 1 to 5 carbon atoms. Z represents an alkylene group which may be substituted, an alkenylene group which may be substituted, or a phenylene group which may be substituted. The alkyl group and the alkenyl group preferably have 1 to 8 carbon atoms. P: represents a substituent represented by the formula (5) or a substituent represented by the formula (6). Q: represents a hydroxyl group, an alkoxyl group, a substituent represented by the formula (5) or a substituent represented by the formula (6). Equation (5)

[0026]

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Equation (6)

[0028]

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The amine component used to form the formulas (1) to (6) is, for example, dimethylamine, diethylamine, N, N-ethylisopropylamine, N, N
-Ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N
-Sec-butylpropylamine, dibutylamine, g-sec-butylamine, diisobutylamine, N, N
-Isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-
Ethylhexyl) amine, dioctylamine, N, N-
Methyloctadecylamine, didecylamine, diallylamine, N, N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N- Dimethylaminoethylamine, N,
N-dimethylaminoamylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-
Diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-
Dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine,
N-methyl-laurylaminopropylamine, N, N-
Ethyl-hexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecoline, 3-pipecoline,
-Pipecoline, 2,4-lupetidine, 2,6-lupetidine, 3,5-lupetidine, 3-piperidinemethanol,
Pipecolic acid, isonipecotic acid, methyl isonicopetinate, ethyl isonicopetinate, 2-piperidineethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-amino Propylpiperidine, N-aminopropyl-2-pipecholine,
N-aminopropyl-4-pipecholine, N-aminopropylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine,
1-cyclopentylpiperazine and the like.

The organic dyes constituting the pigment derivative having a basic group include, for example, diketopyrrolopyrrole dyes, azo dyes such as azo, disazo and polyazo, phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine and flavantron. Anthraquinone dyes, quinacridone dyes, dioxazine dyes such as anthantrone, indanthrone, pyranthrone, biolanthrone,
Perinone dye, perylene dye, thioindigo dye, isoindoline dye, isoindolinone dye,
These are dyes such as quinophthalone dyes, sulene dyes, and metal complex dyes.

The anthraquinone derivative having a basic group may be an alkyl group such as a methyl group or an ethyl group, an amino group, a nitro group, an alkoxy group such as a hydroxyl group or a methoxy group, an ethoxy group, or a substituent such as a halogen group such as chlorine. May be provided.

The triazine derivative having a basic group includes an alkyl group such as a methyl group and an ethyl group, an amino group or a dimethylamino group, an alkylamino group such as a diethylamino group and a dibutylamino group, a nitro group, a hydroxyl group and a methoxy group. , An ethoxy group, an alkoxy group such as a butoxy group,
Halogen such as chlorine or methyl group, methoxy group, amino group, dimethylamino group, phenyl group or methyl group which may be substituted with hydroxyl group, ethyl group, methoxy group,
Ethoxy group, amino group, dimethylamino group, diethylamino group, nitro group, may have a substituent such as a phenylamino group which may be substituted with a hydroxyl group, etc.
5-triazine.

The pigment derivative or anthraquinone derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, after introducing substituents represented by formulas (7) to (10) into an organic dye or anthraquinone, an amine component which reacts with the above substituents to form formulas (1) to (4), for example, N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazine-2-
[Ilamino] aniline and the like. Equation (7)

[0034]

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Equation (8)

[0036]

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Equation (9)

[0038]

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Equation (10)

[0040]

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When the organic dye is an azo dye, the substituents represented by the formulas (1) to (4) are introduced into the diazo component or the coupling component in advance, and then the coupling reaction is performed. An azo pigment derivative can also be produced.

The triazine derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example,
Starting from cyanuric chloride, an amine component forming a substituent represented by formula (1) to formula (4) on at least one chlorine of cyanuric chloride, for example, N, N-dimethylaminopropylamine or N-methylpiperazine And then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.

The pigments constituting the present invention include diketopyrrolopyrrole pigments, azo pigments such as azo, disazo and polyazo, copper phthalocyanine, halogenated copper phthalocyanine,
Phthalocyanine-based pigments such as metal-free phthalocyanine, anthraquinone-based pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavanthrone, anthantrone, indanthrone, pyranthrone and biolanthrone, quinacridone-based pigments, dioxazine-based pigments, perinone-based pigments, perylene Pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, sulene pigments, metal complex pigments and other organic pigments, or titanium oxide, zinc white, zinc sulfide, lead white, carbonic acid Calcium, precipitated barium sulfate, white carbon, alumina white, kaolin clay,
Talc, bentonite, black iron oxide, cadmium red, red iron, molybdenum red, molybdate orange, chrome vermillion, graphite, cadmium yellow,
Yellow iron oxide, titanium yellow, chromium oxide, viridian, titanium cobalt green, cobalt green, cobalt chrome green, victoria green, ultramarine, navy blue, cobalt blue, cerulean blue, cobalt silica blue, cobalt zinc silica blue, manganese violet, cobalt violet Such as inorganic pigments, or
Carbon black such as acetylene black, channel black and furnace black.

The amount of the resin having a sulfonic acid group in the pigment composition of the present invention is preferably 40 parts by weight or less, more preferably 10 to 30 parts by weight, based on 100 parts by weight of the pigment. The amount of the pigment derivative is preferably 1 to 30 parts by weight, more preferably 5 to 20 parts by weight, based on 100 parts by weight of the pigment.

The pigment dispersion of the present invention contains the pigment composition of the present invention, and may further contain a resin as contained in various varnishes. Examples of resins include petroleum resin, casein, shellac, rosin-modified maleic resin, rosin-modified phenol resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber, phenolic resin, and alkyd resin. , Polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylic resin, methacrylic resin, polyurethane resin, silicone resin, fluororesin, drying oil, synthetic dryness Examples include oil, styrene-modified maleic acid, polyamide resin, chlorinated polypropylene, butyral resin, and vinylidene chloride resin. Further, the pigment dispersion of the present invention can contain an organic solvent, water, a commercially available dispersant, and various additives.

The pigment dispersion of the present invention is obtained by mixing the pigment composition of the present invention with various solvents, resins, additives, commercially available dispersants and the like, if necessary, to form a horizontal sand mill, a vertical sand mill, an annular bead mill, an attritor. It can be manufactured by dispersing in the above method. A resin having a sulfonic acid group,
The pigment derivative, anthraquinone derivative or triazine derivative having a basic group (hereinafter referred to as pigment derivative having a basic group, etc.), pigment, other resin, and additives are dispersed after mixing all components. Although it is good, first, only a pigment having a sulfonic acid group and a pigment derivative having a basic group and a pigment, or only a resin having a sulfonic acid group and a pigment derivative having a basic group are dispersed. Dispersion may be performed again by adding another component. In addition, before performing dispersion with a horizontal sand mill, a vertical sand mill, an annular bead mill, an attritor, or the like, pre-dispersion using a kneading machine such as a kneader, a three-roll mill, or a two-roll mill, or Treatment with a resin having a sulfonic acid group and a pigment derivative having a basic group may be performed. In addition, all dispersers and mixers such as a high-speed mixer, a homomixer, a ball mill, a roll mill, a stone mill, and an ultrasonic disperser can be used for producing the dispersion of the present invention.

The pigment dispersion of the present invention can be used for non-aqueous or aqueous paints, gravure inks, offset inks, plastic coloring and the like.

Hereinafter, examples of the production of a resin having a sulfonic acid group, a pigment derivative having a basic group, and the like according to the present invention, and examples of the present invention will be described. Hereinafter, "parts" means "parts by weight". The molecular weight of the resin is a weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography). Resin Production Example [Production Example 1] A separable four-necked flask was equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, and a stirring device, and charged with 477 parts of isopropyl alcohol and 60 parts of ion-exchanged water.
After the temperature was raised to 76 ° C. and the inside of the reaction vessel was replaced with nitrogen, 47 parts of methyl methacrylate, 259 parts of n-butyl methacrylate, and 2-hydroxyethyl methacrylate 7 were added through a dropping tube.
1 part of a mixed solution of 2,2'-azobisisobutyronitrile and 4 parts of 2-acrylamide-
Aqueous solution of 2-methylpropanesulfonic acid (25% concentration)
Was added dropwise over 2 hours. After the completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a resin having a solid content of 40% and a weight average molecular weight of 24,000. [Production Example 2] A separable four-necked flask was equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, and a stirrer, and charged with 477 parts of isopropyl alcohol and ion-exchanged water 60.
After the temperature was raised to 6 ° C and the inside of the reaction vessel was replaced with nitrogen, 45 parts of methyl methacrylate, 246 parts of n-butyl methacrylate, and 67 parts of 2-hydroxyethyl methacrylate were added through a dropping tube.
And a mixture of 4 parts of 2,2'-azobisisobutyronitrile at the same time, an aqueous solution of sodium styrenesulfonate (40% concentration) was dropped from another dropping tube over 2 hours. After the completion of the dropwise addition, the reaction was continued for another 3 hours to obtain a solid content of 40%.
%, A resin having a weight average molecular weight of 30,000 was obtained. [Production Example 3] (Comparative Example) A separable four-necked flask was equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, and a stirrer, and charged with 547 parts of methanol. The temperature was raised to 65 ° C, and the inside of the reaction vessel was purged with nitrogen. A mixed solution composed of 45 parts of methyl methacrylate, 247 parts of n-butyl methacrylate, 90 parts of 2-hydroxyethyl methacrylate, 67 parts of methacrylic acid, and 2 parts of 2,2′-azobisisobutyronitrile was dropped from the dropping tube for 2 hours. And dropped. After the completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a resin having a solid content of 45% and a weight average molecular weight of 7,000. Production of Pigment Derivative Having Basic Group [Production Example 4] After chlorosulfonating 50 parts of copper phthalocyanine as a dye component, the pigment derivative was reacted with 14 parts of N, N-dimethylaminopropylamine as an amine component to produce a pigment derivative ( 1) 62 parts were obtained. Pigment derivative (1)

[0049]

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CuPc represents a copper phthalocyanine residue. [Production Example 5] After chloromethylating 50 parts of copper phthalocyanine as a dye component, it was reacted with 40 parts of dibutylamine as an amine component to obtain 95 parts of a pigment derivative (2). Pigment derivative (2)

[0051]

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CuPc represents a copper phthalocyanine residue. [Production Example 6] 50 parts of quinacridone as a dye component was chloroacetamidomethylated, and then N-amine as an amine component.
Pigment derivative (3) by reacting with 40 parts of methylpiperazine
103 parts were obtained. Pigment derivative (3)

[0053]

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[Production Example 7] A pigment derivative (4) was obtained in the same manner as in Production Example 1, except that diphenyldiketopyrrolopyrrole was used as a coloring matter component and N-aminopropylmorpholine was used as an amine component. Pigment derivative (4)

[0055]

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[Production Example 8] Anthraquinone-β-carboxylic acid chloride (50 parts) was reacted with an amine component N, N-diethylaminopropylamine (36 parts) to obtain 66 parts of a pigment derivative (5). Pigment derivative (5)

[0057]

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[Production Example 9] Dioxazine violet (Pigment Violet 23) was used as the dye component, and the compound represented by the formula (11) was used as the amine component. The pigment derivative (6) was produced in the same manner as in Production Example 1. Obtained. Equation (11)

[0059]

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Pigment derivative (6)

[0061]

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[Production Example 10] 50 parts of diaminodianthraquinone (Pigment Red 177) as a dye component were reacted with 42 parts of cyanuric chloride to form an amine component and 28 parts of N, N-dimethylaminopropylamine to obtain a pigment derivative ( 7) 108 parts were obtained. Pigment derivative (7)

[0063]

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[Production Example 11] A diazo coupling reaction was carried out between 50 parts of a diazo component p-nitroaniline and 109 parts of a coupler having an amine component represented by the formula (12) to give 160 parts of a pigment derivative (8). Obtained. Equation (12)

[0065]

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Pigment derivative (8)

[0067]

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[Production Example 12] 263 parts of a pigment derivative (9) were obtained by subjecting 50 parts of a tetrazo component dichlorobenzidine to 212 parts of a coupler having an amine component represented by the formula (13) by a diazo coupling reaction. . Equation (13)

[0069]

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Pigment derivative (9)

[0071]

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[Production Example 13] 50 parts of a diazo component having an amine component represented by the formula (14) and a coupler component 5
30 parts of acetoacetylaminobenzimidazolone was subjected to a diazo coupling reaction to obtain 79 parts of a pigment derivative (10). Equation (14)

[0073]

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Pigment derivative (10)

[0075]

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[Production Example 14] 50 parts of aniline, 99 parts of cyanuric chloride, N, N-dimethylaminopropylamine 5
By reacting 5 parts in methanol, 168 parts of a pigment derivative (11) was obtained. Pigment derivative (11)

[0077]

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By reacting a dye component, anthraquinone or triazine with an amine component, or by coupling a compound having an amine component to synthesize a dye in the same manner as in Production Examples 1 to 14,
Various pigment derivatives constituting the present invention can be produced. Production and Evaluation of Dispersion The following paint was prepared to evaluate the performance of the pigment dispersion of the present invention. Dispersion was performed using a steel ball and a paint shaker. The viscosity of the obtained paint was measured with a B-type viscometer, and the performance of the dispersion was evaluated based on the viscosity and the TI value (the lower the viscosity, the better the better. The closer the TI value to 1, the better).
In preparing the coating, the resin having a sulfonic acid group was used after replacing the synthesis solvent with cyclohexanone.

As shown in Table 1 below, the dispersion of the present invention
As compared with the comparative example, a good viscosity and a good TI value were shown. (Coating component) Pigment Pigment derivative Resin having sulfonic acid group Alkyd resin Melamine resin Thinner (cyclohexanone / xylene / n-butanol = 6/2/2)

[0080]

[Table 1]

[0081]

[0082]

The pigment composition of the present invention, when dispersed in various vehicles, comprises a pigment derivative having a basic group, anthraquinone having a basic group or a triazine having a basic group, and a resin having a sulfonic acid group. Interact to give a stable pigment dispersion. Therefore, by using the pigment composition of the present invention, a stable pigment dispersion can always be produced even when the pigment dispersibility of the resin contained in the vehicle is poor.

Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat II (Reference) C09B 29/33 C09B 29/33 B 35/035 35/035 35/10 35/10 47/16 47/16 47/24 47/24 48/00 48/00 A 57/00 57/00 Z 67/20 67/20 L C09C 3/08 C09C 3/08 3/10 3/10 C09D 11/00 C09D 11/00 // C09D 201 / 00 201/00 (72) Inventor Takayuki Nogami 2-3-13 Kyobashi, Chuo-ku, Tokyo Toyo Ink Manufacturing Co., Ltd.F-term (reference) 4H056 AA01 AA02 AB01 AB03 AC02 AD25B AD35C EA16 FA01 4J037 AA30 CC12 CC29 EE08 FF15 4J038 DA162 DD121 DD231 GA13 JA34 JB02 JB06 JB36 KA08 LA06 MA07 MA08 NA23 4J039 AD10 AD12 AD22 AE05 BC17 BC52 BC79 BE01 CA06 CA07

Claims (5)

[Claims] 1. A method comprising: a pigment derivative having a basic group; an anthraquinone derivative having a basic group; or a triazine derivative having a basic group; a resin having a sulfonic acid group; and a pigment. And a pigment composition. 2. The pigment composition according to claim 1, wherein the sulfonic acid group forms a metal salt or an amine salt. 3. The resin having a sulfonic acid group is a resin obtained by copolymerizing an ethylenically unsaturated monomer having a sulfonic acid group and an ethylenically unsaturated monomer having no sulfonic acid group. The pigment composition according to claim 1. 4. A pigment derivative, anthraquinone derivative or triazine derivative having a basic group, wherein at least one of the groups represented by the following formulas (1), (2), (3) and (4) The pigment composition according to any one of claims 1 to 3, which has a substituent. Formula (1) Formula (2) Formula (3) Formula (4) _{X: -SO 2 -, - CO} -, - CH 2 NHCOCH 2 -,
—CH ₂ — or a direct bond. n represents an integer of 1 to 10. R _1, R _2: each independently, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group or further together with R ₁ and R _2, Represents an optionally substituted heterocycle containing a nitrogen, oxygen or sulfur atom. R _{3 represents} an alkyl group which may be substituted, an alkenyl group which may be substituted or a phenyl group which may be substituted. R ₄ , R ₅ , R ₆ , and R ₇ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group. _{Y: -NR 8 -Z-NR 9} - or a direct bond. R ₈ and R ₉ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group. Z represents an alkylene group which may be substituted, an alkenylene group which may be substituted, or a phenylene group which may be substituted. P: represents a substituent represented by the formula (5) or a substituent represented by the formula (6). Q: represents a hydroxyl group, an alkoxyl group, a substituent represented by the formula (5) or a substituent represented by the formula (6). Formula (5) Formula (6) 5. A pigment dispersion obtained by dispersing the pigment composition according to claim 1 in a varnish.