JP5173333B2 - Pigment composition, coloring composition using the same, and color filter - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a pigment composition being satisfactorily superior in dispersibility, dispersion stability, transparency and clearness, a coloring composition and a color filter containing the pigment composition. <P>SOLUTION: The pigment composition contains an organic pigment, and at least one selected from the group consisting of compounds represented by general formulae (1), (2) and (3). <P>COPYRIGHT: (C)2008,JPO&amp;INPIT

Description

  The present invention relates to a pigment composition, a coloring composition, and a color filter.

  Many examples of using a pigment as a colorant for a polymer organic compound are known. For example, various printing inks such as gravure printing ink, sizing color, binder color, coating agent, various paints, dry toner or wet toner for electrophotography , Thermal transfer recording ink, writing instrument ink, and the like (for example, Patent Documents 1 and 2).

  However, there is no known pigment colorant that sufficiently satisfies characteristics such as high transparency and color sharpness required for a color filter pixel forming coating liquid and inkjet ink. If the primary particle diameter of the pigment used in these applications is refined to a level of several tens to several hundreds of nanometers to improve transparency and sharpness, the reaggregation force of the pigment particles themselves is increased by the refinement, The dispersibility and dispersion stability of the pigment are deteriorated. Then, although the example (for example, patent documents 3-5) using a dispersing agent etc. is also known, it is still inadequate to obtain the characteristic calculated | required by the said use. For this reason, the pigment colorants prepared by the above-described prior art cannot satisfy all of the dispersibility, dispersion stability, transparency, and sharpness at present.

JP-A-8-20731 JP-A-8-27391 JP-A-9-122470 Japanese Patent Laid-Open No. 9-137075 JP 2003-66224 A

  Accordingly, an object of the present invention is to provide a pigment composition sufficiently excellent in dispersibility, dispersion stability, transparency, sharpness, and the like, a coloring composition containing the pigment composition, and a color filter.

The above object is achieved by the present invention described below. That is, the present invention provides an organic pigment, a pigment composition which comprises a compound represented by the following general formula (3).

(In the general formula (3), X is, represents the water atom or one or a plurality of optional substituents,, Q is have a hydrogen atom or one or a plurality of arbitrary substituents, It represents a phenyl group which may be, R represents an aromatic ring which may have one or more optional substituents. However, the compound represented by the general formula (3) is no less Both have a substituent represented by one COOM or SO ₃ M (M represents a hydrogen atom, a metal atom, an ammonium group, an organic amine group, or a quaternary ammonium group.)

In the pigment composition of the present invention, the organic pigment is, C. I. Pigment red 122, C.I. I. Pigment red 177, C.I. I. Pigment red 254 and C.I. I. Compounds of to the organic pigment 100 parts by weight, represented by the general formula (3); is at least one selected from Pigment Violet 19; primary particle diameter of the organic pigment, it is 100nm or less It is preferable to contain a product ( hereinafter sometimes referred to as “the acid group-introducing dye of the present invention”) at a blending ratio of 0.1 to 30 parts by mass.

Further, the present invention provides a front Kikao sweetener composition, a coloring composition comprising a film-forming material. Colored composition, color filter pixels forming coating Ekima others are particularly useful as a jet in click. The present invention also provides a color filter characterized by Rukoto includes a pixel formed by using the coloring composition.

  According to the present invention, it is possible to provide a pigment composition that is sufficiently excellent in dispersibility, dispersion stability, transparency, sharpness, and the like, a coloring composition containing the pigment composition, and a color filter.

Next, the present invention will be described in more detail with reference to preferred embodiments.
The acid group-introduced dye of the present invention used in the present invention represents a diazonium salt of a compound represented by the following general formula (4), (5) or (6) as a diazo component, represented by the following general formula (7). The compound to be produced can be obtained by a known coupling method using the compound as a coupler component, but the production method is not particularly limited. However, in the above coupling reaction, the resulting compounds represented by the general formulas (1), (2), and (3) each have at least one COOM group or SO ₃ M group. It is necessary to select and use the compounds represented by the general formulas (4), (5), (6) and (7).

（式中、Ｘは前記と同意義を有する。）
上記一般式（４）〜（６）で表される化合物としては、例えば、２−アミノ−４−メチル−５−クロロベンゼンスルホン酸、３−アミノ−６−クロロベンゼンスルホン酸、３−アミノ−４−メトキシベンズアミド、２−アミノ−４−ニトロトルエン、２−アミノナフタレンスルホン酸、１−アミノ−４−ブロモアントラキノン−２−スルホン酸、α−アミノアントラキノン、アニリン、４−アミノ−３−ニトロトルエン、４−アミノ−３−メトキシニトロベンゼンなどが挙げられるが、これらに限定されない。

(In the formula, X has the same meaning as described above.)
Examples of the compounds represented by the general formulas (4) to (6) include 2-amino-4-methyl-5-chlorobenzenesulfonic acid, 3-amino-6-chlorobenzenesulfonic acid, and 3-amino-4- Methoxybenzamide, 2-amino-4-nitrotoluene, 2-aminonaphthalenesulfonic acid, 1-amino-4-bromoanthraquinone-2-sulfonic acid, α-aminoanthraquinone, aniline, 4-amino-3-nitrotoluene, 4-amino Examples include, but are not limited to, 3-methoxynitrobenzene.

（式中、ＱおよびＲは前記と同意義を有する。）
上記一般式（７）で表される化合物としては、例えば、２−ヒドロキシ−３−フェニルカルバモイルナフタレン、２−ヒドロキシ−３−（２−メチルフェニルカルバモイル）ナフタレン、２−ヒドロキシ−３−（４−クロロフェニルカルバモイル）ナフタレン、２−ヒドロキシ−３−ナフトエ酸アニライド−４’−スルホン酸などが挙げられるが、これらに限定されない。

(In the formula, Q and R are as defined above.)
Examples of the compound represented by the general formula (7) include 2-hydroxy-3-phenylcarbamoylnaphthalene, 2-hydroxy-3- (2-methylphenylcarbamoyl) naphthalene, 2-hydroxy-3- (4- Chlorophenylcarbamoyl) naphthalene, 2-hydroxy-3-naphthoic acid anilide-4′-sulfonic acid and the like, but are not limited thereto.

  In the general formulas (1) to (7), examples of the optional substituent other than the carboxylic acid group and the sulfonic acid group include substituents such as a nitro group, a hydroxy group, an alkoxy group, an alkyl group, and a halogen group. However, it is not limited to these. Examples of the metal that forms a salt with the carboxylic acid group and the sulfonic acid group include alkali metals such as Li, Na, and K, and polyvalent metals such as Ca, Ba, Al, Mn, Sr, Mg, and Ni. However, it is not limited to these. Examples of organic amines that form salts with carboxylic acid groups and sulfonic acid groups include, but are not limited to, (mono, di, or tri) alkylamines, substituted or unsubstituted alkylamines, and the like. Moreover, a benzene ring and a naphthalene ring are mentioned as an aromatic ring. The acid group in the acid group-introduced dye of the present invention is particularly preferably a sulfonic acid group or a salt group thereof, and the number of sulfonic acid groups is preferably one per molecule.

  Examples of the organic pigment used in the present invention include azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, quinophthalone pigments, Examples include, but are not limited to, diketopyrrolopyrrole pigments, anthraquinone pigments, thioindigo pigments, and metal complex pigments.

  Among these organic pigments, C.I. I. Pigment red 122, C.I. I. Pigment red 177, C.I. I. Pigment red 254 and C.I. I. At least one selected from pigment violet 19 is preferable.

  The organic pigment used in the present invention has a primary particle size of 100 nm or less, or an organic pigment having a primary particle size of 100 nm or less by atomization treatment, It is preferable from the viewpoint of improving the sharpness. Examples of the pigment atomization method include a salt milling method in which mill milling is performed in the presence of salt (for example, JP-A-2001-220520 and JP-A-2001-264528). I can't.

  The pigment composition of the present invention is produced by mixing the organic pigment and the acid group-introduced dye of the present invention by a conventionally known method (for example, JP-A Nos. 2001-271004 and 2004-91497). For example, a method of mixing powders of the organic pigment and the acid group-introducing dye of the present invention, the organic pigment dispersed in water or an organic solvent having solubility, and the acid group-introducing dye of the present invention And a method of mixing the suspensions with each other, a method of adding the acid group-introducing dye of the present invention to an arbitrary step in the production process of the organic pigment, and the like, but the production method is not particularly limited. As an arbitrary process in the said pigment manufacturing process, although salt milling is mentioned, for example, it is not restricted to this. Examples of the state when the acid group-introducing dye of the present invention is added include, but are not limited to, powder, paste, and suspension.

  The blending ratio of the pigment composition of the present invention is preferably such that the acid group-introduced dye of the present invention is 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight with respect to 100 parts by weight of the organic pigment. The ratio of parts. If the blending ratio of the acid group-introduced dye of the present invention is too small, the intended effect is not sufficiently obtained. Moreover, even if the blending ratio is too large, an effect proportional to the ratio cannot be obtained, and the various physical properties of the pigment composition and the coloring composition using the pigment composition are decreased, and the original hue is greatly changed. Become.

  In the present invention, the following mechanism can be considered as the reason why the acid group-introduced dye of the present invention has a useful function on the organic pigment. Since the acid group-introduced dye of the present invention used in the present invention contains an aromatic ring in the molecular skeleton, it is considered that the acid group-introduced dye is effectively adsorbed on the surface of the organic pigment having the aromatic ring skeleton by the interaction of π electrons. Furthermore, since the molecular weight of the acid group-introduced dye of the present invention is small, it is considered that the steric hindrance can be suppressed and adsorption can be performed more efficiently. At this time, polar groups such as a sulfonic acid group or a carboxylic acid group of the acid group-introduced dye of the present invention emerge on the surface of the adsorbed organic pigment, and the negative surface potential of the pigment surface increases. This is thought to be due to an increase in pigment dispersibility and dispersion stability over time.

  The acid group-introduced dye of the present invention can be used in combination with a conventionally known dispersant, for example, rosin, a polymeric dispersant, a surfactant, or a pigment derivative having a polar group introduced. Examples of rosin include, but are not limited to, rosin derivatives, rosin-modified maleic resins, rosin-modified phenolic resins, rosin-modified fumarate resins, and the like. Examples of the polymeric dispersant include commercially available Dispavic 160, 161, 162, 163, 164, 182, and 184 from BYK, Solsperse 22000, 24000, and 28000 from Abycia, and Disparon DA- from Enomoto Kasei Co., Ltd. 234, 325, 375, 725, etc., but are not limited thereto. Examples of pigment derivatives include, but are not limited to, commercially available Solsperse 5000, 2200 manufactured by Avicia.

  The pigment composition of the present invention includes, for example, various printing inks, sizing colors, binder colors and coating agents, various paints, electrophotographic dry toners or wet toners, thermal transfer recording inks, writing instrument inks, and coatings for forming color filter pixels. It can be used as a colorant for liquids and inkjet inks. Among them, it is particularly useful for a coating solution for forming a color filter pixel and an ink-jet ink that have a high level of required dispersibility, dispersion stability, transparency, and sharpness.

  In general, the color filter pixel forming coating liquid is made of, for example, a photosensitive polyacrylate resin, a photosensitive acrylic resin, a photosensitive polyamide resin, a photosensitive polyimide resin, or an unsaturated polyester resin. Photosensitive resin varnishes, or varnishes in which monomers or oligomers are further added as reaction diluents to these, photoinitiators (with sensitizers if necessary), solvents, etc. are added and then highly dispersed. . At that time, by using the pigment composition of the present invention as the pigment, a coating solution for forming a color filter pixel excellent in dispersibility, dispersion stability, transparency and sharpness can be obtained.

  Examples of the monomer or oligomer include (meth) acrylic acid ester, (meth) acrylic acid, (meth) acrylamide, vinyl acetate, styrene, (meth) acrylonitrile, (meth) acrylate oligomer, and the like. Not limited. Examples of the photoinitiator include, but are not limited to, acetophenone series, benzoin series, benzophenone series, thioxanthone series, triazine series, carbazole series, and imidazole series. Examples of the sensitizer include, but are not limited to, acylphosphine oxide, methylphenylglyoxylate, quinone, anthraquinone, isophthalophenone, ester, benzyl, and benzophenone. Absent. Examples of the solvent include (poly) alkylene glycol monoalkyl ether, (poly) alkylene glycol monoalkyl ether acetate, ether, ketone, alkyl lactate ester, ester, aromatic hydrocarbon, amide, and the like. I can't.

  In general, an inkjet ink is composed of a pigment, for example, water, a water-soluble resin, a surfactant, a water-soluble solvent, and the like, and for the purpose of further improving storage stability, ejection stability, and the like, After adding a viscosity modifier, a specific resistance modifier, an antifoaming agent, an antifungal agent, etc., it is manufactured by highly dispersing. At that time, by using the pigment composition of the present invention as the pigment, an inkjet ink excellent in dispersibility, dispersion stability, transparency and sharpness can be obtained.

  Examples of the water-soluble resin include, but are not limited to, acrylic, acrylic-styrene, polyester, polyamide, and polyurethane resins. Examples of the surfactant include, but are not limited to, anionic, nonionic, amphoteric, and cationic surfactants. Examples of the water-soluble solvent include, but are not limited to, alcohol, polyhydric alcohol, polyhydric alcohol ether, amine, heterocycle, sulfoxide, sulfone, and acetonitrile.

  Next, although a synthesis example, an Example, and a comparative example are given and this invention is demonstrated further more concretely, this invention is not limited to these. In the text, “part” is based on mass.

Synthesis Example of Acid Group-Introducing Dye 20.5 parts of 2-amino-4-methyl-5-chlorobenzenesulfonic acid as diazo component and 27.0 parts of 2-hydroxy-3-phenylcarbamoylnaphthalene as coupler component are known methods To obtain 45.0 parts of acid group-introduced dye A described in Table 1 below.

  Except that the diazo component and coupler component were changed, the reaction was carried out in the same manner according to the synthesis example of acid group-introduced dye A to obtain acid group-introduced dye B to acid group-introduced dye J in Table 1 below.

A list of the synthesis results is shown in Table 1.

[Examples of pigment composition]
Reference example 1
C. I. An aqueous suspension containing 3 parts of acid group-introduced dye A was added to an aqueous suspension containing 20 parts of Pigment Red 254 pigment. After stirring the mixed solution for 30 minutes, the mixed solution was filtered and washed with water, and the taken out pigment paste was dried overnight and pulverized to obtain 21 parts of the target pigment composition.

Reference example 2
With acid group-introduced dye B instead of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Reference example 3
With acid group-introduced dye C instead of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.

Reference example 4
With acid group-introduced dye D in place of the acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Reference Example 5
With acid group-introduced dye E in place of the acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.

Reference Example 6
With acid group-introduced dye F in place of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Reference Example 7
With acid group-introduced dye G in place of the acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.

Reference Example 8
With acid group-introduced dye H in place of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Comparative Example 1
The same operation was performed without adding the acid group-introduced dye A used in Reference Example 1 to obtain an untreated pigment.

Reference Example 9
C. I. An aqueous suspension containing 3.5 parts of acid group-introduced dye H was added to an aqueous suspension containing 35 parts of Pigment Red 177 pigment. After stirring the mixed solution for 30 minutes, the mixed solution was filtered and washed with water, and the taken out pigment paste was dried overnight and pulverized to obtain 36 parts of the target pigment composition.

Example 10
With acid group-introduced dye I in place of the acid group-introduced dye H of Example 9 was carried out in the same manner as in Reference Example 9.
Example 11
With acid group-introduced dye J instead of acid group-introduced dye H of Example 9 was carried out in the same manner as in Reference Example 9.
Comparative Example 2
The same operation was performed without adding the acid group-introduced dye H used in Reference Example 9 to obtain an untreated pigment.

[Preparation, test and evaluation of coating solution for forming color filter pixels]
Using the pigment compositions prepared in Reference Examples 1 to 9, Examples 10 and 11, and the untreated pigment prepared in Comparative Examples 1 and 2, a color filter pixel forming coating solution was prepared as follows, and the viscosity Then, storage stability and lightness were tested.

[Preparation of coating solution for forming color filter pixels]
Reference Example 12
After putting 180 parts of zirconia beads in a 250 ml glass bottle, add the pigment composition prepared in Reference Example 1, an acrylic resin, a polymer dispersant, and propylene glycol monoacetate (PGM-Ac), and easily by premixing. After mixing, the mixture was dispersed for 3 hours using a paint conditioner to obtain 100.0 parts of a dispersion. Thereafter, the dispersion obtained earlier in a 250 ml glass bottle, acrylic resin, dipentaerythritol hexaacrylate, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2,4-diethylthioxanthone, And PGM-Ac were added and sufficiently stirred, followed by filtration through a membrane filter to obtain 150.0 parts of a color filter pixel forming coating solution (see the table below for details of the composition).

Reference Example 13
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 2 instead of the pigment composition prepared in Reference Example 1.
Reference Example 14
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 3 instead of the pigment composition prepared in Reference Example 1.
Reference Example 15
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 4 instead of the pigment composition prepared in Reference Example 1.

Reference Example 16
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 5 instead of the pigment composition prepared in Reference Example 1.
Reference Example 17
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 6 instead of the pigment composition prepared in Reference Example 1.
Example 18
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 7 instead of the pigment composition prepared in Reference Example 1.

Reference Example 19
Using the pigment composition prepared in Reference Example 8 instead of the pigment composition prepared in Reference Example 1, the same procedure as in Reference Example 12 was performed.
Comparative Example 3
Using the untreated pigment prepared in Comparative Example 1 instead of the pigment composition prepared in Reference Example 1, the same procedure as in Reference Example 12 was performed.

Reference Example 20
After adding 200 parts of zirconia beads in a 250 ml glass bottle, add the pigment composition prepared in Reference Example 9, acrylic resin, polymer dispersant, and PGM-Ac, and mix them easily by premixing. And dispersed for 3 hours to obtain 100.0 parts of a dispersion. Thereafter, the dispersion obtained earlier in a 250 ml glass bottle, acrylic resin, dipentaerythritol hexaacrylate, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2,4-diethylthioxanthone, And PGM-Ac were added and sufficiently stirred, followed by filtration with a membrane filter to obtain 150.0 parts of a color filter pixel forming coating solution (see the table below for details).

Example 21
Using the pigment composition prepared in Example 10 instead of the pigment composition prepared in Reference Example 9, the same procedure as in Reference Example 20 was performed.
Example 22
Using the pigment composition prepared in Example 11 instead of the pigment composition prepared in Reference Example 9, the same procedure as in Reference Example 20 was performed.
Comparative Example 4
The same process as in Reference Example 20 was performed using the untreated pigment prepared in Comparative Example 2 instead of the pigment composition prepared in Reference Example 9.

[Testing and evaluation of coating solution for forming color filter pixels]
<Viscosity and storage stability>
Reference Example 12-20 and allowed to stand for one hour in Example 21, 22, and Comparative Examples 3 and 4 obtained in 25 ° C. in a color filter pixel-forming coating liquid. Thereafter, the viscosity was measured using a B-type viscometer (trade name: BL type, 30 rpm value, manufactured by Tokimec Co., Ltd.), and this measured value was taken as the initial viscosity. Next, after measuring the initial viscosity, the sample was held at 25 ° C. for 1 week, and then the viscosity with time was measured in the same manner as the measurement of the initial viscosity. There were four levels of evaluation: ◎ for no level, ◯ for usable level, △ for somewhat difficult use due to thickening, and x for unusable level for significant thickening.

<Brightness>
Reference Example 12-20, Example 21, 22, and Comparative (manufactured by ABLE Corporation) spin coater obtained color filter pixel-forming coating liquid in Examples 3 and 4 is dropped onto the center of the glass plate was set in a glass A coating solution for forming color filter pixels was coated on the plate. After that, pre-baking was performed. Using the spectrocolorimeter (Minolta Co., Ltd., trade name: CM-3600d (type)), the chromaticity of the prepared glass was measured with a standard light source C and a vertical viewing angle of 2 degrees. Y, x, y) were determined and the contrast was measured. The numerical values of Comparative Examples 3 and 4 were each set to 100%, and the numerical values of the Examples were converted to calculate the contrast.

The above test results are shown in Tables 2 and 3.

  Tables 2 and 3 show the evaluation results of the addition and non-addition of the acid group-introduced dye of the present invention. The coating solution for forming a color filter pixel using the acid group-introduced dye of the present invention is as follows. The initial viscosity was lower than that of the coating solution for forming a color filter pixel without using the acid group-introducing dye of the present invention. Further, almost no change in viscosity over time was observed, and the storage stability was excellent. Furthermore, the contrast value increased about 10 to 30% with respect to the contrast of Comparative Example 3, and increased about 20% with respect to the contrast of Comparative Example 4.

[Examples of pigment composition]
Reference Example 23
C. I. An aqueous suspension containing 1.5 parts of acid group-introduced dye A was added to an aqueous suspension containing 30 parts of Pigment Red 122 pigment. After stirring the mixed solution for 15 minutes, the mixed solution was filtered and washed with water, and the taken out pigment paste was dried overnight and pulverized to obtain 27 parts of the intended pigment composition.
Comparative Example 5
The same operation was performed without adding the acid group-introduced dye A used in Reference Example 23 to obtain an untreated pigment.

[Preparation, testing and evaluation of inkjet ink]
Using the pigment composition prepared in Reference Example 23 and the untreated pigment prepared in Comparative Example 5, an ink-jet ink was prepared as follows, and the dispersion particle size, viscosity, storage stability, and color saturation were tested. Went.

[Preparation of inkjet ink]
Reference Example 24
After adding 120 parts of zirconia beads in a 250 ml glass bottle, the pigment composition prepared in Reference Example 23, a water-soluble styrene acrylic resin, and ion-exchanged water were added and mixed briefly by premixing, and then for 5 hours using a paint conditioner. Dispersion was performed to obtain 60.0 parts of a dispersion. Thereafter, the dispersion obtained earlier in a 250 ml glass bottle, triethylene glycol monobutyl ether, glycerin, surfinol, ion-exchanged water, methanol and 10% glycerylated chitosan (deacetylation degree 80%, glyceryl substitution degree 1.1) aqueous solution The mixture was sufficiently stirred and filtered through a membrane filter having a pore size of 5 microns to obtain 100.0 parts of ink-jet ink (refer to the table below for details).

Comparative Example 6
Using the untreated pigment prepared in Comparative Example 5 instead of the pigment composition prepared in Reference Example 23, the same procedure as in Reference Example 24 was performed.

[Test and evaluation of inkjet ink]
<Dispersed particle size and particle size stability>
The inkjet ink obtained in Reference Example 24 and Comparative Example 6 was allowed to stand at 25 ° C. for 1 hour. Then, the average particle diameter of the pigment in inkjet ink was measured using the laser scattering type particle size distribution analyzer (Beckman Coulter company make, brand name: N5 Submicron Particle Size Analyzer), and this value was made into the initial particle diameter. Next, this ink-jet ink was held at 50 ° C. for 10 days, and then the average particle diameter of the pigment in the ink was measured in the same manner as the measurement of the initial particle diameter. As the determination of the particle size stability, the case where the ratio (φ2 / φ1) of the initial particle size (φ1) to the time-lapsed particle size (φ2) was 1.5 or less was evaluated as “○”, and the case where the ratio exceeded 1.5 was evaluated as “x”.

<Viscosity and storage stability>
The inkjet ink obtained in Reference Example 24 and Comparative Example 6 was allowed to stand at 25 ° C. for 1 hour. Thereafter, the viscosity was measured using an E-type viscometer (trade name: RE80 type, 50 rpm value, manufactured by Tokyo Sangyo Co., Ltd.), and this measured value was taken as the initial viscosity. Next, after measuring the initial viscosity, the sample was held at 50 ° C. for 10 days, then the viscosity was measured in the same manner as the measurement of the initial viscosity, the viscosity with time was measured, and the storage stability was determined as the initial value. The case where the ratio (η2 / η1) of the viscosity (η1) and the time-dependent viscosity (η2) was 2.0 or less was evaluated as ○, and the case where the ratio exceeded 2.0 was evaluated as ×.

<Hue and transparency>
The prepared ink-jet ink was developed on a hiding power test paper (Nippon Test Panel Industry Co., Ltd.) with a bar coater standard No. 6, and a gloss of 60 degrees was measured with a gloss meter (BYK Hayes Gloss Meter). . In addition, the transparency was evaluated by visually developing the ink-jet ink on a commercially available OHP film for ink-jet printing according to bar coater standard No. 6. Evaluation was good: ○, translucent: Δ, no transparency: x.

The above test results are shown in Tables 4 and 5.

  The ink-jet ink using the acid group-introduced dye according to the present invention exhibited excellent initial particle size stability with little initial particle size and little change with time. In terms of fluidity, it exhibits a low initial viscosity and excellent viscosity stability over time. Moreover, it was excellent in transparency compared with the conventional product and had high gloss.

  According to the present invention, it was possible to provide a coloring composition excellent in dispersibility, dispersion stability, transparency and sharpness, and a pigment composition used therefor. The pigment composition of the present invention and the coloring composition using the same are, for example, various printing inks, sizing colors, binder colors and coating agents, various paints, electrophotographic dry toners or wet toners, thermal transfer recording inks, and writing instruments. It can be used for ink, coating liquid for forming color filter pixels, inkjet ink and the like. Among them, it is particularly useful for a coating solution for forming a color filter pixel and an ink-jet ink, which have high required levels of dispersibility, dispersion stability, transparency and sharpness.

Claims (7)

And organic pigments, pigment composition which comprises a compound represented by the following general formula (3).

(In the general formula (3), X is, represents the water atom or one or a plurality of optional substituents,, Q is have a hydrogen atom or one or a plurality of arbitrary substituents, It represents a phenyl group which may be, R represents an aromatic ring which may have one or more optional substituents. However, the compound represented by the general formula (3) is no less Both have a substituent represented by one COOM or SO ₃ M (M represents a hydrogen atom, a metal atom, an ammonium group, an organic amine group, or a quaternary ammonium group.) The organic pigment is C.I. I. Pigment red 122, C.I. I. Pigment red 177, C.I. I. Pigment red 254 and C.I. I. The pigment composition according to claim 1, wherein the pigment composition is at least one selected from pigment violet 19. The pigment composition according to claim 1 or 2 , wherein the organic pigment has a primary particle size of 100 nm or less. Relative to the organic pigment 100 parts by weight, the pigment composition according to the compound represented by the general formula (3) in any one of claims 1 to 3, including the proportions of 0.1 to 30 parts by weight object. A coloring composition comprising the pigment composition according to any one of claims 1 to 4 and a film-forming material. The coloring composition according to claim 5 color filter pixels forming coating Ekima the other is jet-in click. A color filter according to claim Rukoto includes a pixel formed by using the coloring composition according to claim 6.