JP2018172451A - Uracil compound or salt thereof, and pigment composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition stable as a colorant of e.g., a resist for color filters, where a pigment composition containing an organic pigment is reduced in particle size and increased in concentration without causing aggregation, sedimentation, or a viscosity increase with time.SOLUTION: The present invention provides a uracil compound represented by a formula (1) or a salt thereof (X, Y and Z are O, S or a bivalent linking group -NR-; Ris H or a C1-4 alkyl group; Ris a phenyl group or a naphthylene group having sulfonic acid or sulfonic acid salt as a substituent).SELECTED DRAWING: None

Description

  The present invention relates to a color filter resist used in the production of liquid crystal displays and imaging devices, uracil compounds used in ink jet inks or salts thereof, and pigment compositions excellent in fluidity and transparency containing the compounds. About.

  In recent years, pigments have been used as colorants for paints and printing inks, and in recent years for color filter resists and inkjet inks. Pigments have various characteristics such as heat resistance, weather resistance, migration resistance, etc., and are excellent in fastness compared to dyes, but on the other hand, aggregation, sedimentation, increase in viscosity over time, dissimilarity It has potential problems such as color separation when mixed with pigments.

  Recently, in order to achieve high contrast in liquid crystal displays, miniaturization of image sensors, high coloring and high definition of ink-jet inks, etc., there has been a demand for finer pigments and higher pigment concentrations in pigment compositions. However, as the particle diameter becomes finer and the pigment concentration increases, aggregation tends to occur and it is difficult to obtain a stable dispersion.

  In order to solve these problems, improvement of the pigment itself (pigment surface treatment), the development of a dispersant having a good adsorptivity to the pigment, the development of a surfactant, and the proposal of pigment derivatives have been made so far. I came. A pigment derivative is a compound in which substituents such as acidity and basicity are introduced into a pigment having the same structure or a similar structure as that of a finely divided pigment, and has an affinity and adsorbability with the pigment and has an acid-base interaction. Therefore, it has a property of improving the fine particle formation and dispersion stability of the pigment, and is used in the process of pulverizing and dispersing fine particles of the pigment. As pigments used in color filters and inkjets, phthalocyanine pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, isoindoline pigments, isoindolinone pigments, azo pigments, There are dye lake pigments, and many pigment derivatives have been reported, particularly phthalocyanine pigments, anthraquinone pigments, and quinacridone pigments. For example, a method of mixing a sulfonated pigment or a metal salt thereof with a pigment (Patent Documents 1 to 3), a method of mixing a substituted aminomethyl derivative (Patent Document 4), a method of mixing a phthalimidomethyl derivative (Patent Document 5), etc. It has been known.

Although these methods are effective for pigments having a specific skeleton, the number of substituents to be introduced can be reduced for pigments that are structurally difficult to introduce sulfone groups, aminomethyl groups, phthalimidomethyl groups, etc. It is difficult to control the position, and as a result, the effect as a dispersant is insufficient, and a by-product that adversely affects the color tone is produced in a large amount, and the quality of the pigment dispersion is not stable.
In addition, the pigment composition using Pigment Red 254, which has been widely used as a red pigment for color filters, has had a problem of improving the transmittance.

Japanese Patent Publication No.41-2466 JP 63-172772 A Japanese Patent Publication No. 50-4019 Japanese Examined Patent Publication No. 39-16787 JP-A-55-108466 U.S. Pat. No. 4,749,795

  The problem to be solved by the present invention is C.I. I. Pigment Red 254 and other pigments containing organic pigments such as red pigments (pigment dispersions) are made finer and highly concentrated without causing aggregation, sedimentation, and increase in viscosity over time. It is to provide a stable composition (dispersion) as a color filter resist or a colorant for inkjet ink.

As a result of intensive studies to solve the above problems, the present inventor has found that the above problems can be solved by using a compound comprising a uracil derivative, and has completed the present invention.
That is, the present invention
(1) The following formula (1)

(In Formula (1), X, Y, and Z represent an oxygen atom, a sulfur atom, or a bivalent coupling group -NR < ₁ >-. R < ₁ > represents a hydrogen atom or a C1-C4 alkyl group. R < ₂ >. Is the following formula (1-A) or (1-B)

(In the formulas (1-A) and (1-B), M represents a hydrogen atom, an alkali metal atom, or a —NZ ₁ Z ₂ Z ₃ Z ₄ group. Z _{1 to} Z ₄ are each independently a hydrogen atom or carbon. Substituted by an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an aralkyl group, a cycloalkyl group having 5 or 6 carbon atoms, an aryl group, or a cycloalkyl group having 5 or 6 carbon atoms Represents a substituent having a carbon number of 1 to 4). Uracil compounds or salts thereof represented by
(2) The uracil compound or a salt thereof according to (1), wherein X, Y and Z are divalent linking groups —NH—.
(3) The uracil compound or a salt thereof according to (1) or (2) above, wherein M is a cesium atom or rosin ammonium (Abieta-8,11,13-triene-18-ammonium),
(4) A pigment composition comprising the uracil compound according to any one of (1) to (3) or a salt thereof, an organic pigment and a resin dispersant,
(5) The pigment composition according to (4), wherein the resin dispersant is a cationic resin dispersant;
(6) The pigment composition as described in (4) or (5) above, wherein the addition amount of the uracil compound or a salt thereof is 1 to 50 parts by mass with respect to 100 parts by mass of the organic pigment;
(7) The pigment composition according to any one of (4) to (6), wherein the organic pigment is a pigment having a diketopyrrolopyrrole skeleton,
(8) A color resist containing the pigment composition according to any one of (4) to (7), a binder resin, and a polymerizable compound,
(9) The inkjet ink composition containing the uracil compound or a salt thereof according to any one of (1) to (3), and (10) further containing at least one organic solvent. (9) The ink composition for inkjet according to
About.

  The uracil compound represented by the formula (1) of the present invention or a salt thereof is extremely easy to produce, and by using this compound, C.I. I. Pigment Red 254 and other pigment compositions containing pigments can be made finer and highly concentrated without causing aggregation, sedimentation, and increase in viscosity over time. Colorants for color filter resists and inkjet inks As a result, a stable dispersion can be obtained.

The present invention is described in detail below.
The uracil compound of the present invention or a salt thereof has a structure represented by the following formula (1).

  The uracil compound or a salt thereof of the present invention can be suitably used as a color filter resist or a colorant for inkjet ink. Hereinafter, for convenience, the “uracil compound of the present invention or a salt thereof” may be simply described as “the compound of the present invention” simply.

In formula (1), X, Y and Z each independently represent an oxygen atom, a sulfur atom or a divalent linking group —NR ₁ —. R ₁ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Specific examples of the alkyl group having 1 to 4 carbon atoms represented by R ₁ in formula (1) are the same as the specific examples of the alkyl group having 1 to 4 carbon atoms represented by Z _{1 to} Z _{4 in} formula (1). And preferred ones are the same.
X, Y and Z in the formula (1) are an oxygen atom, a sulfur atom or a divalent linking group —NR ₁ —, and R ₁ is preferably a hydrogen atom or a methyl group, and a divalent linking group. More preferably, it is —NR ₁ —, and R ₁ is a hydrogen atom.

In formula (1), R ₂ represents a substituent represented by the above formula (1-A) or (1-B).
In formulas (1-A) and (1-B), M represents a hydrogen atom, an alkali metal atom, or a —NZ ₁ Z ₂ Z ₃ Z ₄ group. Z _{1 to} Z ₄ are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an aralkyl group, a cycloalkyl group having 5 or 6 carbon atoms, an aryl group, or An alkyl group having 1 to 4 carbon atoms substituted by a cycloalkyl group having 5 or 6 carbon atoms is represented.
Specific examples of the alkali metal atom represented by M in the formulas (1-A) and (1-B) include a lithium atom, a sodium atom, a potassium atom, a rubidium atom, a cesium atom, a francium atom, a lithium atom, A sodium atom, a potassium atom, and a cesium atom are preferable, and a cesium atom is more preferable.

The alkyl group having 1 to 4 carbon atoms represented by Z _{1 to} Z _{4 in the} formulas (1-A) and (1-B) may be either linear or branched, but is preferably linear. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group, and the methyl group or the ethyl group. Preferably, it is an ethyl group.
Specific examples of the hydroxyalkyl group represented by Z _{1 to} Z _{4 in the} formulas (1-A) and (1-B) include a hydroxymethyl group, a hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxybutyl group and the like can be mentioned, and hydroxyethyl group is preferable.
Specific examples of the aralkyl group represented by Z _{1 to} Z _{4 in the} formulas (1-A) and (1-B) include a benzyl group, a phenylethyl group, a phenylpropyl group, and a phenylbutyl group, preferably benzyl It is a group.

Specific examples of the cycloalkyl group having 5 or 6 carbon atoms represented by Z _{1 to} Z _{4 in the} formulas (1-A) and (1-B) include a cyclopentyl group and a cyclohexyl group, preferably cyclohexyl. It is a group. The cycloalkyl group mentioned here may be increased with a saturated hydrocarbon ring and / or an unsaturated hydrocarbon ring, and the hydrogen atom on the ring of the cycloalkyl group and / or the hydrogen atom on the increase is an alkyl group. It may be substituted with a substituent such as a group. Specific examples of the —NZ ₁ Z ₂ Z ₃ Z ₄ group having a ring-increased and having an alkyl group and a cycloalkyl group having 5 or 6 carbon atoms include rosin ammonium (Abieta-8, 11, 13). -Triene-18-ammonium) is preferred.
Specific examples of the aryl group represented by Z _{1 to} Z _{4 in the} formulas (1-A) and (1-B) include a phenyl group and a naphthyl group, and a phenyl group is preferable.

In the formulas (1-A) and (1-B), the alkyl group having 1 to 4 carbon atoms substituted by the cycloalkyl group having 5 or 6 carbon atoms represented by Z _{1 to} Z ₄ is 5 or An alkyl group having 1 to 4 carbon atoms having a cycloalkyl group having 6 carbon atoms as a substituent, that is, a cycloalkyl-substituted alkyl group, and specific examples of the cycloalkyl group having 5 or 6 carbon atoms in the cycloalkylalkyl group Examples are the same as the specific examples of the cycloalkyl group having 5 or 6 carbon atoms represented by Z _{1 to} Z ₄ in formula (1), and _{1 to 4} carbon atoms in the cycloalkyl group. Specific examples of the alkyl group include the same as the specific examples of the alkyl group having 1 to 4 carbon atoms represented by Z _{1 to} Z ₄ in the formulas (1-A) and (1-B).

M in the formulas (1-A) and (1-B) is a lithium atom, a sodium atom, a potassium atom, a cesium atom, or a -NZ ₁ Z ₂ Z ₃ Z ₄ group, and Z ₁ To Z ₄ are each independently a hydrogen atom or a cycloalkyl group having 5 or 6 carbon atoms, preferably a cesium atom or rosin ammonium (Abieta-8,11,13-triene-18-ammonium). Is more preferable.

In the formulas (1-A) and (1-B), the introduction position of the —SO ₃ M group is not particularly limited, but the carbon atom represented by 1 to 6 on the benzene ring in the following formula (1-A ′) Is preferably substituted with 4 carbon atoms, and is preferably substituted with 5 carbon atoms among the carbon atoms represented by 1 to 8 on the naphthalene ring in the following formula (1-B ′). . Note that M in the formulas (1-A ′) and (1-B ′) has the same meaning as M in the formulas (1-A) and (1-B).

Examples of the uracil compound represented by the formula (1) of the present invention or a salt thereof include X, Y, Z (R ₁ in the divalent linking group —NR ₁ —), R ₂ and M (—NZ). ₁ Z ₂ Z ₃ Z ₄ groups Z ₁ to Z ₄ in) compound or more preferably a salt thereof in combination with one each of the preferred, more preferred compounds or salts thereof in combination with what is more preferable.

  Examples of the amine used for salt formation of the compound of the formula (1) include ammonia, diethylamine, triethanolamine, benzylamine, and rosinamine (18-aminoabieta-8,11,13-triene).

  The salt of the uracil compound represented by the formula (1) may be a free acid, a tautomer thereof, or a mixture of these various salts. For example, any combination such as a mixture of cesium salt and ammonium salt, a mixture of free acid cesium salt, a mixture of lithium salt and cesium salt may be used. Depending on the type of salt, the physical properties such as solubility may differ, and if necessary, select the type of salt as appropriate, or change the ratio when containing multiple salts, etc. It is also possible to obtain a mixture having

The uracil compound of the present invention represented by the formula (1) can be synthesized, for example, by the following method.
That is, a desired compound can be obtained by subjecting a compound represented by the following formula (2) or (3) obtained by a conventional method to a condensation reaction with a uracil compound. In the following formulas (2) and (3), M and Z represent the same meaning as M and Z in the above formula (1).

  Specific examples of the compound of the present invention are shown below. In addition, the acidic functional group of a compound shall be represented in the form of a free acid for convenience.

The pigment composition of the present invention contains the compound of the present invention, an organic pigment and a resin dispersant.
The organic pigment contained in the pigment composition of the present invention is not particularly limited as long as it is a conventionally known one such as those described in the color index, but the compound represented by the formula (1) of the present invention itself is a red type. Since it has a hue, it is preferable to use a red organic pigment in the sense that it does not impair the original hue of the organic pigment, more preferably an organic pigment classified as pigment red by color index. I. Pigment Red 254 is more preferable. In addition, the organic pigment contained in the pigment composition is preferably an organic pigment having a diketopyrrolopyrrole skeleton in the sense that it is excellent in dispersion stability when mixed with the compound of the present invention.

  The resin dispersant contained in the pigment composition of the present invention is not particularly limited as long as it is a known resin dispersant, but a cationic resin dispersant is preferable in view of affinity with the compound of the present invention. Examples of cationic resin dispersants include BYK112, 116, 140, 142, 161, 162, 164, 166, 182, 2000, 2001, 2050, 2070, 2150 from Big Chemie Japan, EFKA4010 from Efka Corporation, 4015, 4020, 4050, 4055, 4060, 4300, 4330, 4400, 4406, Solsperse of Nippon Lubrizol Corporation, 24000, 32500, Ajimoto Fine Techno Co., Ltd. Ajisper PB711, 821, 822, 881 and the like. The addition amount of the resin dispersant is usually 5 to 100 parts by mass, preferably 10 to 50 parts by mass with respect to 100 parts by mass of the organic pigment. When the addition amount of the resin dispersant is less than 5 parts by mass, good dispersion stability cannot be obtained.

  If necessary, an organic solvent can be added to the pigment composition of the present invention. The organic solvent that can be used is not particularly limited, for example, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethyl cellosolve acetate, butyl cellosolve acetate, ethyl cellosolve, cyclohexanone, cyclopentanone, ethylene glycol diethyl ether, Examples include diethylene glycol dimethyl ether, ethyl acetate, butyl acetate, methanol, ethanol, and isopropyl alcohol. These may be used alone or in admixture of two or more. The organic solvent is used in an amount of 90% by mass or less in the pigment composition.

The color resist of the present invention contains the pigment composition of the present invention, a binder resin and a polymerizable compound.
The binder resin that can be used in the color resist of the present invention is not particularly limited. For example, styrene (co) polymer, (meth) acrylic acid ester (co) polymer, styrene-maleic acid ester copolymer, cellulose Examples thereof include acetate-based resins, polyester-based resins, polyurethane-based resins, polyamide-based resins, and polyimide-based resins. These may be used alone or in combination of two or more. The binder resin is used in an amount occupying 50% by mass or less in the pigment composition.

Examples of the polymerizable compound that can be used in the color filter resist of the present invention include a photopolymerizable monomer, an epoxy compound, and a melamine compound. Specific examples of these polymerizable compounds include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethylene glycol di (meth) acrylate, and diethylene glycol di (meth). Acrylate, triethyleneglycol (meth) acrylate, tetraethylene glycol (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate , Dipentaerythritol hexa (meth) acrylate, glycerol (meth) acrylate, bisphenol-A type epoxy di (meth) acrylate, bisphenol Nord-F type epoxy di (meth) acrylate, bisphenol-fluorene type epoxy di (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, ethoxylated glycerin tri (meth) acrylate , Ethoxylated isocyanuric acid tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, ethoxylated pentaerythritol tetra (meth) acrylate, 9,9-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene, cayarad RP-1040 (Nippon Kayaku), Kayrad DPCA-30 (Nippon Kayaku), UA-33H (Shin Nakamura Chemical), UA-53H (Shin Nakamura Chemical) and M-8060 (Toagosei) (Meth) acrylate monomers: TEMPIC (manufactured by Sakai Chemical), TMMP (manufactured by Sakai Chemical), thiol polymerization monomers such as PMP (manufactured by Sakai Chemical) and DPMP (manufactured by Sakai Chemical); NC-6000 of Nippon Kayaku products NC-6300, NC-6300H, NC-3000, EOCN-1020, XD-1000, EPPN-501H, BREN-S, NC-7300L, Daicel Chemicals' Celoxite 2021P, EHPE3150, Cyclomer M100, Epolide PB3600, Japan Epoxy Resin products Epicoat 828, Epicoat YX8000, Epicoat YX4000, Printec products VG-3101L, Silaace S510 (Nisso), TEPIC (Nissan Chemical Industries) and other epoxy compounds; and methylolated melamine and Mw Melamine-based compounds such as -30 (Sanwa Chemical) are mentioned, but are not limited thereto.
These polymerizable compounds are preferably used in combination with a polymerization initiator, a curing accelerator or the like, if necessary.

  Other additives that can be added to the pigment composition of the present invention as necessary include, for example, thixotropic agents, polymerization initiators and curing agents, curing accelerators, polymerization inhibitors, organic or inorganic fillers, coupling agents, and the like. Although these may be mentioned, these may be selected according to the specific intended use of the pigment composition, and are not limited to the above. Further, the addition amount may be selected in accordance with a specific purpose application.

  The pigment composition of the present invention can be prepared, for example, by the following method. That is, as a method of blending the organic pigment and the compound of the present invention, various conventionally known methods, for example, a method of simply mixing each dry powder or press cake, various dispersions such as a kneader, a bead mill, a dissolver, an attritor, etc. Examples thereof include a method of mechanically mixing by a machine, a method of suspending an organic pigment in water or an organic solvent, and adding and mixing the compound of the present invention therein to deposit uniformly on the surface of the organic pigment. Next, a mixture of the obtained organic pigment and the compound of the present invention is blended with a resin dispersant and various organic solvents, a binder resin, various additives, etc. as necessary, and a sand mill, an annular bead mill, an attritor, etc. The desired pigment composition can be produced by dispersing in step (b). Alternatively, for convenience, the organic pigment, the compound of the present invention, the resin dispersant, and other components as necessary may be mixed and dispersed in a lump. The addition amount of the compound of the present invention in the pigment composition of the present invention is usually 0.1 to 70 parts by weight, preferably 0.5 to 60 parts by weight, more preferably 100 parts by weight of the organic pigment. 1 to 50 parts by mass. If the compounding ratio of the compound of the present invention is too small, the desired dispersion stability and fine particle formation of the organic pigment cannot be achieved, and even if the compounding ratio is excessively increased, the dispersion stability is decreased. Optimization is necessary.

  The use of the pigment composition of the present invention is not particularly limited. For example, various printing inks such as gravure printing inks, paints, dry toners or wet toners for electrophotography, inks for inkjet recording, resist colorants for color filters, and the like. Applications are listed. In particular, the pigment composition of the present invention is useful as a resist colorant for color filters and ink for ink jet recording that require finer pigments and high stability.

  Hereinafter, the present invention will be described specifically by way of examples. In the text, “parts” and “%” are based on mass unless otherwise specified. The maximum absorption wavelength in the examples is a value measured by a spectrophotometer “UV-3150 manufactured by Shimadzu Corporation”, and the acid value is a value measured by a measurement method based on JIS K-0070: 1992. The weight average molecular weight is a value calculated in terms of polystyrene based on the measurement result of gel permeation chromatography.

Example 1 (Synthesis of the compound represented by No. 1 of the above specific example compound)
(Process 1)
“Aqueous solution 1” was obtained by adding 14 parts of sulfanilic acid to 400 parts of water and adjusting the pH to 10 with a 25% aqueous sodium hydroxide solution. Under stirring, 15 parts of cyanuric chloride was added to 340 parts of ice water for suspension, and the whole amount of “Aqueous solution 1” obtained above at a reaction temperature of 0 to 5 ° C. was added. During this time, a 25% aqueous sodium hydroxide solution was added to the reaction system to maintain the pH value at 2.5 to 3.5, and the mixture was stirred at the same temperature for 1 hour, and contained a compound represented by the following formula (4). 800 parts of “Aqueous solution 2” were obtained.

(Process 2)
To the reaction vessel was added 21 parts of 6-aminouracil, 200 parts of NMP and the total amount of “Aqueous Solution 2” containing the compound represented by formula (4) obtained in Step 1, and the mixture was reacted at 100 ° C. for 10 hours. The reaction solution was cooled to 0 ° C. and filtered to obtain 820 parts of “Wet Cake 1”. After 410 parts of “Wet Cake 1” were suspended in 500 parts of water and the pH value was adjusted to 10 to 11 with a 25% aqueous sodium hydroxide solution, 14 parts of cesium chloride was added and stirred at 45 ° C. for 1 hour. The “wet cake 2” obtained by filtering the reaction solution was dried with a hot air dryer at 80 ° C. 14 parts of the compound represented by 1 were obtained. The maximum absorption wavelength λmax of the compound was 320 nm (NMP).

Example 2 (Synthesis of a compound represented by No. 2 of the above specific example compound)
(Process 3)
Instead of using 14 parts of cesium chloride, the same procedure as in Step 2 was used, except that 7.1 parts of 18-aminoabieta-8,11,13-triene was dissolved in 69 parts of 3.3% acetic acid aqueous solution. Specific compound No. 26 parts of the compound represented by 2 were obtained. The maximum absorption wavelength λmax of the compound was 320 nm (NMP).

Example 3 (Synthesis of the compound represented by No. 7 of the above specific example compound)
(Process 4)
"Aqueous solution 3" was obtained by adding 18 parts of 2-aminonaphthalene-6-sulfonic acid to 400 parts of water and adjusting the pH to 10 with a 25% aqueous sodium hydroxide solution. Under stirring, 15 parts of cyanuric chloride was added to 340 parts of ice water for suspension, and the total amount of “Aqueous solution 3” obtained above at a reaction temperature of 0 to 5 ° C. was added. During this time, a 25% aqueous sodium hydroxide solution is added to the reaction system to maintain the pH value at 2.5 to 3.5, and the mixture is stirred at the same temperature for 1 hour, and contains a compound represented by the following formula (3). 800 parts of “Aqueous solution 4” were obtained.

(Process 5)
To the reaction vessel was added 24 parts of 6-aminouracil, 200 parts of NMP, and the total amount of “Aqueous solution 4” containing the compound represented by formula (3) obtained in Step 4, and after reacting at 100 ° C. for 10 hours, The reaction solution was cooled to 0 ° C. and filtered to obtain 820 parts of “Wet Cake 3”. After 410 parts of “Wet Cake 3” were suspended in 500 parts of water and the pH value was adjusted to 10 to 11 with a 25% aqueous sodium hydroxide solution, 14 parts of cesium chloride was added and stirred at 45 ° C. for 1 hour. The “wet cake 4” obtained by filtering the reaction solution was dried with a hot air dryer at 80 ° C. 14 parts of the compound represented by 7 were obtained. The maximum absorption wavelength λmax of the compound was 322 nm (NMP).

Example 4 (Synthesis of the compound represented by No. 2 of the above specific example compound)
(Step 6)
Instead of using 14 parts of cesium chloride, the same procedure as in Step 5 was used, except that an aqueous solution in which 7.1 parts of 18-aminoabieta-8,11,13-triene was dissolved in 69 parts of 3.3% acetic acid aqueous solution was used. Specific compound No. 26 parts of the compound represented by 8 were obtained. The maximum absorption wavelength λmax of the compound was 320 nm (NMP).

Synthesis example 1 (adjustment of binder resin A)
A 500 ml four-necked flask is charged with 160 parts of methyl ethyl ketone, 10 parts of methacrylic acid, 33 parts of benzyl methacrylate, and 1 part of α, α'-azobis (isobutyronitrile), and nitrogen gas is introduced into the flask for 30 minutes while stirring. did. Then, it heated up to 80 degreeC and stirred for 4 hours as it was at 80 to 85 degreeC. After completion of the reaction, the reaction mixture was cooled to room temperature to obtain a colorless, transparent and uniform binder resin solution. This was precipitated in a 1: 1 mixed solution of isopropyl alcohol and water, filtered, and the solid content was taken out and dried to obtain a binder resin A. The obtained binder resin A had a polystyrene equivalent weight average molecular weight of 18,000 and an acid value of 152.

Example 5 (Preparation of the pigment composition of the present invention)
As an organic pigment, C.I. I. Pigment Red 254 10.0 parts, No. obtained in Example 1 as a compound of the present invention. 1.0 parts of the compound represented by 1; 1.8 parts of the binder resin A obtained in Synthesis Example 1 as the binder resin; Azisper PB881 (manufactured by Ajinomoto Fine Techno Co.) as the resin dispersant; 82 parts of propylene glycol monomethyl ether acetate as the solvent After premixing, the mixture was dispersed with a paint shaker for 60 minutes using 0.3 mm zirconia beads. The obtained dispersion was filtered through a 5 μm filter to prepare a pigment composition.

Example 6 (Preparation of the pigment composition of the present invention)
No. 1 obtained in Example 1. No. 1 obtained in Example 2 instead of the compound represented by No. 1. A pigment composition was prepared in the same manner as in Example 5 except that the compound represented by 2 was used.

Example 7 (Preparation of the pigment composition of the present invention)
No. 1 obtained in Example 1. No. 1 obtained in Example 3 instead of the compound shown in FIG. A pigment composition was prepared in the same manner as in Example 5 except that the compound represented by 7 was used.

Example 8 (Preparation of the pigment composition of the present invention)
No. 1 obtained in Example 1. No. 1 obtained in Example 4 instead of the compound shown in FIG. A pigment composition was prepared in the same manner as in Example 5 except that the compound represented by 8 was used.

Comparative Example 1 (Preparation of comparative pigment composition)
No. 1 obtained in Example 1. A pigment composition was prepared in the same manner as in Example 5 except that the compound represented by 1 was not used.

The pigment compositions of Examples 5 to 8 and Comparative Example 1 were measured for viscosity using a B-type viscometer at room temperature (25 ° C.) of 10 rpm and evaluated according to the following criteria. In order to confirm the storage stability, in addition to the initial (immediately after adjustment), the viscosity after standing at 40 ° C. for 3 days was also measured and evaluated. The results are shown in Table 1.
Evaluation criteria Initial viscosity: less than 20 mPa · s ○, 20 mPa · s or more ×
40 ° C. × 3 days later viscosity increase rate: less than 20% ○, 20% or more ×
In addition, about the thing gelatinized immediately after preparation, the viscosity after leaving to stand at 40 degreeC for 3 days was set to "it cannot evaluate."

As is clear from Table 1, the pigment compositions of Examples 5 to 8 have a lower initial viscosity than that of Comparative Example 1 in which the present pigment derivative is not added. And the quality of the ink is not impaired. Furthermore, the storage stability was better than that of the comparative example.
Specifically, Comparative Example 1 was not dispersible due to gelation, while Examples 5 to 8 had a viscosity increase rate of 20% or less after 40 ° C. × 3 days.

By using the uracil compound of the present invention, it is possible to make fine particles and increase the concentration without agglomeration, sedimentation, and increase in viscosity over time. The pigment derivative can be used as a color filter resist or ink jet ink. It is very useful as a colorant for obtaining a stable dispersion.

Claims (10)

Following formula (1)

(In Formula (1), X, Y, and Z represent an oxygen atom, a sulfur atom, or a bivalent coupling group -NR < ₁ >-. R < ₁ > represents a hydrogen atom or a C1-C4 alkyl group. R < ₂ >. Is the following formula (1-A) or (1-B)

(In the formulas (1-A) and (1-B), M represents a hydrogen atom, an alkali metal atom, or a —NZ ₁ Z ₂ Z ₃ Z ₄ group. Z _{1 to} Z ₄ are each independently a hydrogen atom or carbon. Substituted by an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an aralkyl group, a cycloalkyl group having 5 or 6 carbon atoms, an aryl group, or a cycloalkyl group having 5 or 6 carbon atoms Represents a substituent having a carbon number of 1 to 4). Or a salt thereof. The uracil compound or a salt thereof according to claim 1, wherein X, Y and Z are a divalent linking group —NH—. The uracil compound or a salt thereof according to claim 1 or 2, wherein M is a cesium atom or rosin ammonium (Abieta-8,11,13-triene-18-ammonium). A pigment composition comprising the uracil compound according to any one of claims 1 to 3 or a salt thereof, an organic pigment, and a resin dispersant. The pigment composition according to claim 4, wherein the resin dispersant is a cationic resin dispersant. The pigment composition according to claim 4 or 5, wherein the amount of the uracil compound or a salt thereof added to 100 parts by mass of the organic pigment is 1 to 50 parts by mass. The pigment composition according to any one of claims 4 to 6, wherein the organic pigment is a pigment having a diketopyrrolopyrrole skeleton. A color resist comprising the pigment composition according to claim 4, a binder resin, and a polymerizable compound. The ink composition for inkjets containing the uracil compound as described in any one of Claims 1 thru | or 3, or those salts. Furthermore, the ink composition for inkjets of Claim 9 containing at least 1 or more types of organic solvent.