TW201221583A - Ultra-fine yellow pigment composition, pigment dispersion containing ultra-fine yellow pigment composition and preparation method for the ultra-fine yellow pigment composition - Google Patents

Abstract

The purpose of the present invention is to provide an ultra-fine yellow pigment composition for promoting contrast when it is used as a coating ink in a color filter. The solution is to adopt an ultra-fine yellow pigment composition comprising a quinophthalone-based pigment, a sulfonated quinophthalone-based pigment derivative and a specific triazine-based pigment derivative. The ultra-fine yellow pigment composition is prepared by adopting a mixture containing quinophthalone-based pigment, sulfonated quinophthalone-based pigment derivative and said triazine-based pigment derivative to carry out grinding and mixing processes at the temperature of 60 DEG C.

Description

201221583 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a yellow pigment composition, and more particularly to a fine yellow pigment composition containing a fine yellow pigment. [Prior Art] For printing inks and paints, for example, inks for inkjet printing and inks for color filters, by dispersing pigments in a fine state, high coloring power is exerted, and the color developing materials and coated materials such as printed matter are held. Characteristics such as vivid color and gloss, and characteristics such as color and contrast of a color filter. In recent years, such applications have required higher vividness, gloss, chroma, contrast, etc. One of the countermeasures is to use a method of refining the pigment. However, generally, once the pigment particles are dispersed in a mixture of water, a solvent, a resin, or the like (a coloring material such as a paint or an ink), the pigment particles tend to aggregate in the mixture (pigment dispersion), and the smaller the particle size of the primary particles of the pigment, The stronger the tendency to agglomerate the secondary particles, the more the pigment is finer, and it is difficult to stably disperse the finely divided pigment particles. When the pigment particles are condensed in the pigment dispersion, most of the unfavorable phenomena such as increasing the viscosity of the pigment dispersion, lowering the gloss of the surface of the color developing material, and lowering the performance of the coating film occur. In addition, the pigments used in color filters are mainly red, green, and blue. In addition, yellow pigments for these complementary colors are generally used. The yellow pigment is known as a quinoline yellow pigment having good heat resistance and weather resistance. However, when it is refined as described above, the performance is lowered (this fact is not the case other than the color-5-201221583 filter). In the same manner, a method for improving the porphyrin yellow pigment having a specific crystal structure (Patent Document 1) and a method using a quinoline yellow derivative sulfonic acid (Patent Document 2) have been proposed. Further, in Patent Document 1, the wet grinding temperature is preferably 80 °C or higher. However, even when such a technique is used, for example, when an ink for a coating film such as a color filter is used, there is still room for improvement in terms of improving the contrast. PRIOR ART DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT PATENT DOCUMENT 1 An object of the present invention is to provide a fine yellow pigment composition which can be improved in comparison when an ink for a coating film such as a color filter is used. MEANS FOR SOLVING THE PROBLEMS As a result of intensive review by the present inventors, it has been found that the above problems can be solved by using quinoline yellow pigments and a plurality of specific pigment derivatives, and the present invention has been completed. That is, the gist of the present invention is as follows. The first aspect of the present invention relates to a quinoline yellow pigment derivative containing a quinoline yellow pigment and a sulfonic acid-6 - 201221583, and a triazine pigment derivative represented by the following formula (1) A fine yellow pigment composition. [1] (1)

(In the formula (1), A is an aromatic amine residue, and hydrazine is a chlorine atomic hydroxyl group, a sulfanihc acid residue or an anthranilic acid residue. In the present invention, the aromatic amine residue A of the triterpene pigment derivative is preferably a group represented by the following formula (2). [2] (2)

-7- 201221583 【化3】 (3)

(In the formula (7), Q1, Q2, Q3, and q4 are each independently _H, haloalkyl or lower alkoxy. X is -H, -OH S_NH2. W 〇-, -S02- or formula (3), 1! and n are each independently 〇 or 丨). The second aspect of the present invention relates to a pigment dispersion containing the aforementioned fine yellow pigment. According to a second aspect of the present invention, in the method for producing a fine yellow pigment, the method comprises the steps of: containing a quinophthalone yellow pigment and the quinoline yellow pigment derivative and the triazine pigment derivative at a temperature of 6 〇 ° C or less. A fine yellow pigment composition method for the step of grinding and kneading. EFFECTS OF THE INVENTION When the fine yellow pigment composition of the present invention is used as an ink for a coating film of color or the like, the contrast of the coating film can be improved. The above fine yellow pigment composition can be easily produced by using the fine yellow pigment composition of the invention of the present application. MODE FOR CARRYING OUT THE INVENTION The fine yellow pigment composition of the present invention is a method for producing a color filter comprising a sulfonated mixture of a porphyrin and a low-CH2-'-pig composition, and a yellow pigment.

S 201221583, a sulfonated quinoline yellow pigment derivative, and a triazine pigment derivative represented by the above formula (1). The representative of the above quinoline yellow pigment is, for example, a color index (hereinafter abbreviated as C.I.), C.I. Pigment Yellow 138 (hereinafter abbreviated as PY138), which is represented by the following formula (4). Known things can be used for PY138, such as Paliotol Yellow D0960 manufactured by BASF Corporation. [4] (4)

In the present invention, the primary particle diameter of the pigment ensures the dispersibility of the pigment. The viewpoint of improving the contrast is preferably from 20 to 60 μm. The sulfonated quinoline yellow pigment derivative (hereinafter simply referred to as "sulfonated pigment derivative") is obtained by subjecting a quinoline yellow pigment or the same pigment derivative to a sulfonation treatment, and the sulfonation treatment can be carried out. For example, it is carried out by a method described in JP-A-2009-126994, another known method, or the like. Further, in the present invention, the sulfonic acid obtained by the above method or the like or the salt of the above sulfonic acid can be used as it is. a compound or atom which forms a salt with the aforementioned sulfonic acid, such as a monoalkyl group such as lithium-9-201221583, potassium, sodium, calcium, magnesium, strontium, aluminum, or the like, a 1- to valent metal atom, 'ethylamine, butylamine, or the like. An organic amine such as a dialkylamine such as an amine, dimethylamine or diethylamine; a trialkylamine such as trimethylamine or triethylamine; an alkanolamine such as monoethanolamine, diethanolamine or triethanolamine; Amine, ammonia, etc. Further, when the salt is an alkali metal salt, since the salt is water-soluble, it is easy to separate the water-soluble impurities by filtration after dissolving the salt in water, thereby obtaining a highly purified sulfonated pigment derivative. The sulfonated quinoline yellow pigment derivative used in the present invention is, for example, a chemical structure represented by the following formula (5), and a salt thereof. [5] (5)

(In the formula (5), p is an integer of 1 to 5. X1 to X8 are each independently a hydrogen atom or a halogen atom). The sulfonated pigment derivative having this structure is a non-parallel state from the plane of the structure of the salino structure and the plane system derived from the quinone imine structure, and therefore it is inferred that it has a moderate affinity with the sulphate yellow pigment and can inhibit quinine. Phosphate yellow system-10-201221583 Pigment particles agglomerate. Further, since the sulfonated pigment derivative has high affinity with the triazine-based pigment derivative as described later, it is estimated that the interaction between the two can be effectively exerted on the sulphate yellow pigment by the interaction between the two. Further, since the molecule has a sulfo group, it is estimated that it has excellent dispersibility for a solvent to be described later, and has a function of effectiveness when preparing a pigment dispersion. The sulfonated quinoline yellow pigment derivative represented by the above formula (5) can be used in the present invention, but among them, X1 to X8 are all chlorine atoms. This product can improve the affinity with the quinophthalone yellow pigment represented by the above formula (4), and promote the adsorption of the pigment by the pigment particles, and is expected to be more effective in preventing crystal growth. The triazine-based pigment derivative may have the above-mentioned A structure represented by the formula (1). The triazine-based pigment derivative having an aromatic amine residue is a compound rich in π electrons, and therefore it is inferred that when the compound is close to the surface of the crystal particles of the quinoline yellow pigment, 'by the π-electron with the pigment molecule The interaction 'in the micronization treatment described later can suppress/control the crystal growth of the primary particles of the quinophthalone yellow pigment. Further, since the triazine-based pigment derivative also has an interaction with the π-electron of the sulfonated pigment derivative molecule, it is estimated that the affinity between the two can be improved, and the effect of both on the sputum yellow pigment can be effectively exerted. . Further, since the sulfonated pigment derivative has a base in the molecule, it is estimated that it has excellent dispersibility for a solvent to be described later, and it is effective to modulate the pigment dispersion. In the present invention, the triazine-based pigment derivative represented by the above formula (1) can be used, but it is preferred that the aromatic amine residue ' of the above-mentioned triazine-based pigment derivative is in the above formula (2). The base of expression. Further, in the present invention, the lower stage of the lower alkyl group and the lower stage oxy group means a substance having a carbon number of 1 to 4. This type of carbon number is inferred to reduce steric hindrance' to further enhance the affinity with pigments. The specific example of the group represented by the above formula (2) is preferably any one of the groups represented by the formulae (6) to (8) from the viewpoint of suppressing the crystal growth of the pyruvate yellow pigment and reducing the primary particle diameter. [6] (6)

[7] (7)

Cl CI

ΝΗ一式 (8) ΝΗ2

该1 This type of di-exposed derivative can be produced by a known method. Alternatively, -12-201221583 can be used as a commercially available product. In the fine pigment composition of the present invention, the content of the acid-expanding pigment derivative is not particularly limited. However, from the viewpoint of improving the coating film, it is preferably 2 to 20 parts by weight based on 100 parts by weight of the quinophthalone pigment. More preferably, the content of the above-mentioned triazine-based pigment derivative is not particularly limited, but from the viewpoint of improving the coating film, it is preferably from 1 to 10 with respect to 100 parts by weight of the quinoline yellow pigment. More preferably, it is 2 to 5 parts by weight. The fine yellow pigment composition of the present invention may contain a dispersant, a resin or the like in addition to the above pigments and pigment derivatives. The fine yellow pigment composition of the present invention can be subjected to grinding and kneading at 60 ° C or lower by mixing a mixture containing a quinophthalone yellow pigment and the above-mentioned acidified quinophthalone yellow pigment derivative and the above triterpenoid pigment derivative. In the above, the PY1 38 is a material having good heat resistance and weather resistance, and the wet grinding temperature in Application Document 1 is preferably 80 ° C or higher. However, the inventors have found that, as described above, the grinding and kneading can be carried out at a lower temperature, and the comparison of the coating films of the color filter or the like can be further improved. Further, it has been found that the quenching and kneading using the above-mentioned plural specific pigment derivative of the quinoline yellow pigment can effectively suppress the crystal growth of the pigment particles and further improve the contrast of the coating film of the final color filter or the like. In the present invention, the kneading can be carried out at a lower temperature of 60 ° C or lower, but the viewpoint of improving the contrast is preferably 20 ° C or higher, more preferably 30 to 50 ° C. When the above-mentioned grinding and kneading is carried out at a lower temperature, the viscosity of the kneaded material can be improved, and the shearing force can be more easily imparted to the kneaded material, and the microscopic pigment is expected to be refined. However, when the mixture is ground and kneaded at a temperature lower than 20 °C, the primary particle size of the pigment is passed, and when the pigment dispersion is prepared, it is agglomerated, which affects the contrast of the coating film. The method for producing the fine yellow pigment composition of the present invention will be described by way of an appropriate honing method, but is not limited thereto, and other known methods such as a dry honing method can be used at a specific temperature. In this example, the quinophthalone yellow pigment, the sulfonic acid pigment derivative, the triazine pigment derivative, and the water-soluble inorganic salt-soluble organic solvent are first mixed, and then premixed by a mixer such as an ultramixer. The mixing is preferably carried out, wherein the sulfonated pigment derivative is 2 to 20 parts by weight, the triazine derivative is 1 to 10 parts by weight, and the water-soluble inorganic salt is 500 to 1,500 parts by weight based on 100 parts by weight of the quinoline yellow pigment. The water-soluble organic solvent is from 100 to 400 parts by weight. The water-soluble inorganic salt is preferably used for a known grinding aid such as sodium chloride or mirabilite (sodium sulfate). The particle size of the inorganic salt is not particularly limited, but it is preferably 5 Ομηι or less from the viewpoint of miniaturization of the pigment. Further, as disclosed in Japanese Laid-Open Patent Publication No. 2009-2635-1, it is possible to use a finely sized material. The water-soluble organic solvent may be an organic solvent used for salt honing, for example, Diethylene glycol (DEG), ethylene glycol, polyethylene glycol, glycerin, etc., but is not limited thereto. Next, the mixture obtained by the premixing is supplied to a kneader, and the temperature of the compound (kneaded product) is adjusted. Grinding is carried out at the same time below 60 ° C. At this time, the temperature of the kneaded material is determined by the wet weight of the kneading viscosity in the batch kneading machine, and the weight of the pigment (anhydride) at the time of the water is determined. The alcohol is known to be mixed in the mixing tank - 1421, 2012, 583, and the kneaded material in the grinding and kneading process is measured by the thermometer after contact correction with respect to the kneaded material discharged from the outlet of the kneading machine. The kneading machine can be 'can be adjusted to the above temperature, and known things can be used. Specifically, a batch type kneading machine such as a kneading machine or a continuous type kneading machine can be used. From the standpoint of controlling the temperature of the mixture in the grinding and kneading, it is preferred to use a continuous kneader. The continuous kneading machine described in Japanese Laid-Open Patent Publication No. Hei 9-263723, and the continuous kneading machine described in JP-A-2006-77062, the latter being manufactured by Asada Iron Works Co., Ltd. Miraku KCK. Then, the finely ground pigment paste obtained by washing the kneaded mixture obtained by the above-mentioned grinding and kneading is washed with ion-exchanged water or the like. Thereafter, if necessary, the dryer is used to dry the fine pigment paste after washing, and the dried mass of the fine pigment is obtained, which is then pulverized by a known pulverizer to obtain a fine pigment powder. In the present invention, the fine pigment paste obtained as described above or the powder of the fine pigment is used as a fine yellow pigment composition. The pigment dispersion of the present invention is an article containing the aforementioned fine yellow pigment composition. Further, the pigment dispersion may contain a solvent, a dispersant, a dispersion resin, other pigments (including a pigment derivative), and other components in addition to the fine yellow pigment composition. The ingredients may be appropriately used as such ingredients, which will be briefly described below. Further, for example, the contents described in JP-A-2009-126994 can be used as appropriate. The solvent is preferably a water-soluble solvent. By using a water-soluble solvent as a solvent, a particularly excellent dispersibility of the pigment can be obtained. The water-soluble solution -15-201221583 can be a hydrophilic solvent, and specifically, for example, a liquid having a solubility of 100 g or more in water of 100 g at 25 g is used. The water-soluble solvent is generally a compound having a functional group having a hydrophilicity such as a hydroxyl group, a compound having a polyol skeleton, and the like. For example, diethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PMA), and the like. The present invention can use a water-insoluble solvent. The dispersant is not particularly limited, and for example, a polymer dispersant can be used. The polymer-based dispersant is, for example, a basic polymer-based dispersant, a neutral-polymer dispersant, or an acidic polymer-based dispersant. Such a polymer-based dispersant such as a dispersant formed of an acrylic-based or modified acrylic-based polymer, an urethane dispersant, a polyamine guanamine salt, a polyether ester, a phosphate ester, or a fat A dispersant formed by a polyvalent carboxylic acid or the like. The content ratio of the dispersing agent in the pigment dispersion is not particularly limited, but is preferably 2 to 28% by weight, more preferably 9 to 25% by weight. The aforementioned dispersion resin is, for example, alginic acid, polyvinyl alcohol, hydroxypropyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, styrene-acrylic resin, styrene-acrylic acid-acrylic resin, Styrene-maleic acid resin, styrene-maleic acid half ester resin, methacrylic acid-methacrylate resin, acrylic acid-acrylate resin, isobutylene-maleic acid resin, rosin modified maleic acid resin, poly The vinylpyrrolidone, the arabinated rubber, the polyallylamine, the polyvinylamine, the polyethylenimine, etc. may be used in combination of one or more selected from the group consisting of the above. The content ratio of the dispersion resin in the pigment dispersion is not particularly limited, but

S -16- 201221583 is preferably 2 to 2 1 wt%, more preferably 6 to 1 9.5 wt%. As the other pigments mentioned above, various known pigments, and pigment derivatives thereof can be used. Further, one type or two or more types of pigments and pigment derivatives may be used. The content of the pigment (the yellow fine pigment composition of the present invention, and other pigments (including the pigment derivative) of the present invention) in the pigment dispersion is preferably 10% by weight or more, more preferably 10 to 25% by weight. The other components mentioned above are coloring agents, pH adjusters, antioxidants, ultraviolet absorbers, preservatives, antifungal agents, and the like. This is equivalent to being appropriately added without impairing the effects of the present invention. The pigment dispersion of the present invention can be adjusted by known methods. Preferred embodiments of the embodiment will be briefly described below, but are not limited thereto. In this example, the inorganic sphere is added to a mixed solution containing a fine yellow pigment composition, a solvent, a dispersant, and a dispersion resin in a multistage manner to carry out dispersion treatment. By adding the inorganic spheres in the multistage form, the fine pigment composition can be dispersed in an efficient and fine state. Further, the other pigments described above and the other components may be added as necessary. The inorganic ball is not particularly limited, and examples thereof include a ball made of zirconia (e.g., Toray ceram crushing ball (trade name), manufactured by Toray Corporation). The average particle diameter of the inorganic spheres used in each stage is not particularly limited, but it is preferably decreasing in order. For example, when the inorganic sphere is added in two stages, the average particle diameter of the inorganic particles of the first stage is 0.5 to 3.0 mm, and the second stage is 0.03 to 0 _ 3 mm. The amount of each of the inorganic spheres to be added is not particularly limited, but is preferably from 300 to 500 parts by weight based on 100 parts by weight of the above mixture. Also, the addition amount of each segment in the range -17-201221583 may be the same or different. The dispersing machine to be subjected to the dispersion treatment is not particularly limited, and is, for example, a constant-diameter dispersing machine such as a tantalum-making machine, and a single-shaft or biaxial kneading machine such as a dispersing pulverizer. The treatment time is not particularly limited, and is preferably from 1 Torr to 120 minutes. Further, the number of revolutions of the stirring blade of the dispersing machine is not particularly limited, and is preferably from 1,000 to 50,000 rpm. Further, the types and conditions of such machines can be appropriately selected according to each section. 段 The number of the inorganic spheres added is not particularly limited, and is preferably added in two stages. Further, in this example, after the inorganic spheres added in the respective stages are removed, other inorganic spheres may be added in the subsequent stage, and the method of removing the inorganic spheres may be a known method such as filtration. The dispersion liquid obtained by dispersing the inorganic spheres in a multistage manner under the above conditions and then dispersing the inorganic spheres in the final stage is the pigment dispersion of the present invention. The pigment dispersion of the present invention can be used, for example, in various coating inks such as various coating materials, lithographic printing, gravure printing, inks for coating films such as color filters, filming agents for lenses, and the like. The pigment dispersion of the present invention can be used for film formation. The coating film can be applied to the substrate by, for example, bar coating, spin coating, roll coating, slit coating, brush coating, lithography, gravure printing, etc., and then dried as necessary. Solvent) can form a coating film of interest. [Embodiment] Hereinafter, the present invention will be described in more detail by way of examples and comparative examples.

S -18-201221583 (Manufacturing Example 1) Preparation of a triazine-based pigment derivative (A) A mixture of 7.3 g of trichlorocyanuric acid and one chlorine of trichlorocyanide is used. Name: ASA aminene sulfonic acid, manufactured by SKAI Chemical Industry Co., Ltd.) 6.8 g of water was added to 1 part of water and reacted at 2 Torr for 1 hour. Next, 4,4'-methyl 2,6-dimethylaniline (trade name: KAYABOND C-200S, manufactured by Nippon Kasei Co., Ltd.) i〇g was added to the amount of chlorine reacted with the reactant. The reaction was carried out at 〇 ° C for 1 hour. After the obtained reaction product was filtered, the residue was washed with water, and then left to stand overnight in a constant temperature bath of 8 (TC) to obtain 17.0 g of the triazine derivative (A) represented by the following formula (9). Formula (9)

(Production Example 2) Preparation of triazine-based pigment derivative (B) 3,3'-dichlorobenzidine 10 g was added to water, and after dispersion, trichlorochloride was added in an amount reactive with one amine group. 7.3 g of cyanuric acid was reacted at 20 ° C for 1 hour. Next, 1 3 · 7 g of p-aminobenzenesulfonic acid was added, and the reaction was carried out at 90 ° C for 1 hour to obtain 26.6 g of a triazine-based pigment derivative (B) having the structure of the following formula (10). -19- 201221583 【化1 〇】 (1 ο) νη2

(Example 1) Yellow 138 of a quinoline yellow pigment (trade name "Pali〇t〇i Yellow L0960HD, manufactured by BASF Corporation" 500 g, using a super mixer (manufactured by Kavada Co., Ltd., super mixer SMV-20) The water-soluble inorganic salt of the mirabilite (average particle transport of about 5 μηι, the Glauber's anhydride described in JP-A-2009-263 50 1) 5 000 g. The water-soluble organic solvent of ethylene glycol l〇45g, the following formula (11) 50 g of the sulfonated pigment derivative and 25 g of the triazine-based pigment derivative (A) of Production Example 1 were pre-mixed for about 2 minutes to make it uniform. The mixture was supplied to a continuous kneading machine (Mirako, Asada Iron Works Co., Ltd.) KCK3 type 2). The kneading conditions were as follows: the amount of extrusion was 6.6 kg/h, the number of revolutions was 90 rpm, and the temperature of the kneaded material was temperature-controlled at 45 ° C for grinding and kneading. The 1300 g of the ground kneaded product was added to 40. : After stirring and dispersing 8000 g of ion-exchanged water, it was transferred to Nuo's filtration' and then repeatedly washed with water until the Glauber's salt was removed to obtain a pigment water paste. The pigment water paste was dried at 60 ° C for 20 hours. Science and technology (stock) system, small pulverizer sample pulverizer SK-M2) smashing the drying The product contains a quench yellow pigment, a sulfonated pigment derivative, and a fine yellow pigment composition of a triazine-based -20-201221583 pigment derivative of about 90 g. [Chemical Formula 1] Formula (1 1 >

CI --fs〇3H)p

Cl (in the formula (11), 'p is an integer of 1 to 5 (Example 2) except that the triazine-based derivative (B) is substituted with the triazine-based derivative (A), and the same as in Example 1 contains quinoline. The fine yellow pigment composition of the yellow pigment, the sulfonated pigment derivative, and the tri-exposed pigment derivative is about 9 〇g. (Example 3) The grinding and kneading is carried out while the temperature of the kneaded product is temperature-controlled at 3 Torr. Further, in the same manner as in Example 1, a fine yellow pigment composition containing a quinoline yellow pigment, a sulfonated pigment derivative, or a triazine pigment derivative was obtained in an amount of about 9 g. (Example 4) a -21 - 201221583 The fine yellow pigment composition containing the porphyrin yellow pigment, the sulfonated pigment derivative, and the dioxin pigment derivative was obtained in the same manner as in Example 1 except that the temperature of the kneaded product was temperature-controlled at 5 〇〇c. (Comparative Example 1) In the same manner as in Example 1, except that the triazine-based pigment derivative was not added, about 90 g of a fine yellow pigment composition containing a porphyrin yellow-based pigment and a sulfonated pigment derivative was obtained. (Comparative Example 2) The same as Comparative Example 1 except that the amount of the sulfonated pigment derivative added was 75 g. A fine yellow pigment composition containing a quinoline yellow pigment and a sulfonated pigment derivative was obtained in an amount of about 90 g. (Evaluation) <Preparation of pigment dispersion and coating film> Fastogen GREEN All® (manufactured by DIC Corporation) of green pigment 1 7.3 6 g, a complementary pigment, 23.55 g of the fine yellow pigment composition of the comparative example, 5.89 g of the sulfonated pigment derivative represented by the above formula (11) (the content of the above three products is called a pigment component), and dispersion Disperbyk LPN-6919 (manufactured by Jue Chemical Co., Ltd.) 24_5g, SPCN-2000 (made of Showa Polymer) of dispersion resin, 27.6g, PMA 71.1g of organic solvent, and a stirrer (single-axis mixer) with a content of 400ml, stir 1 〇 minutes. At this time, the number of revolutions of the stirring wing of the mixer is 2 000 rpm. 201221583 Next, the inorganic sphere (the first inorganic sphere) with an average particle diameter of 〇8 mm, chrome oxide, "Toray ceram crushing ball" (trade name), 640 g, manufactured by Toray Co., Ltd., and stirred for 30 minutes at room temperature to carry out the first stage of dispersion treatment (first treatment). At this time, the number of revolutions of the stirring blade of the mixer was 2000 rpm, and then filtered using a filter ("PALL HDCII Membrane Filter", manufactured by PALL Corporation) to remove the inorganic sphere (the first inorganic sphere), and then PMA was added to make the pigment component. 15 wt%, an inorganic sphere having an average particle diameter of 0.1 mm in an amount of 4 times the total amount of the total amount added (the second inorganic sphere, chrome oxide, "Toray ceram crushing ball" (trade name), Donglei The company's production process) was stirred for 90 minutes to carry out the second stage of dispersion treatment (second treatment). At this time, the number of revolutions of the stirring blade of the mixer was 200 rpm. Thereafter, a filter ("PALL HDCII Membrane Filter" (trade name), manufactured by PALL Co., Ltd.) was used to filter, and the inorganic ball (second inorganic ball) was removed to obtain a desired pigment dispersion. The above-prepared pigment dispersion was prepared into a film-like coating plate (coating film) using a spin coater (MIKASA SPINCORTER IH-DX2). The coating film was heated at 23 ° C for 1 hour, and was subjected to the following evaluation. (Evaluation) Using the above-mentioned prepared coating film, Y値, X値 'contrast (CR) was measured by a spectrophotometer (SPECTROI»HOTOMETER CM-3700d). Further, the measurement method of the comparison was as follows. That is, the color filter is held by two polarizing plates, and the transmitted illuminance when the polarizing surfaces of the polarizing plates are parallel is measured and the illuminance is perpendicular to -23-201221583, and the comparison is performed. For the measurement of the illuminance, the brightness meter "LS-100" (manufactured by Minoda Co., Ltd.) was used. The results of each measurement are shown in Table 1. Further, in the evaluation column of the table, y 値 is 0.55 値, and contrast (CR) is the relative ratio based on 値 of Comparative Example 1. [Table 1] Fine yellow pigment composition Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Modified derivative derivative 1 Note 1 M0 10 10 10 10 10 15 Derivative 2 Note 2 [wt %] 5 0 5 5 0 0 Derivative 3 in 3 [wtX] 0 5 0 0 0 0 Temperature g ^ TC] 45 45 30 50 45 45 Evaluation of coating film Y値76.6 76.4 76.1 76.3 76.8 75.9 X値0.356 0.355 0.354 0.355 0.356 0.353 CR [%] 109 129 109 110 Reference 24 Note 1: Derivative 1 is a sulfonated pigment derivative represented by formula (11). Note 2: Derivative 2 is a triazine-based pigment derivative of Production Example 1. (A) Note 3: Derivative 3 is a triazine-based pigment derivative (B) of Production Example 2. It is used as shown in Table 1, and is obtained by kneading and pulverizing at a certain temperature, and containing a sulfonated pigment derivative and When the pigment dispersion obtained by the yellow fine pigment composition of the triazine-based pigment derivative is used, the coating film prepared by the pigment dispersion can improve the contrast. In contrast, the triazine-based pigment derivative is not used, and the addition of the sulfonated pigment derivative greatly decreases the contrast. Therefore, the fine yellow pigment composition of the present invention is suitable for providing a coating film for enhancing a contrast color filter or the like. -twenty four-

Claims (1)

201221583 VII. Application for Patent Park: 1. A fine yellow pigment composition characterized by containing Quinophthalone pigments and acidified quinoline yellow pigment derivatives, and the following formula (1) The triazine-based pigment derivative shown, [Chemical 1] (In the formula (1), A represents an aromatic amine residue, and B represents a chlorine atom, a hydroxyl group, a p-aminobenzene acid extension residue or an o-amine benzenesulfonic acid residue). 2. The fine yellow pigment composition of claim 1 of the patent application, wherein A of the aromatic amine residue of the three-exposed pigment derivative is a group represented by the following formula (2), 】 (2) -25- 201221583 【化3】 (3) (In the formula (2), 'Q丨, Q2, Q3, and Q4 are not each independently—Η, a halogen atom, a lower alkyl group or a lower alkoxy group; X represents ·Η,·0Η or·ΝΗ2; w represents _ CH2-, -0-, -S〇2- or formula (3); m and η are each independently 0 or 1). 3. A pigment dispersion characterized by 'a fine yellow pigment composition comprising the first or second aspect of the patent application. A method for producing a fine yellow pigment composition, which is a method for producing a fine yellow pigment composition according to claim 1 or 2, which comprises the steps of: containing a quinoline yellow pigment, and the foregoing The mixture of the acidified sapylin yellow pigment derivative and the aforementioned triazine pigment derivative was ground and kneaded at 60 °C. -26- 201221583 Four designated representatives: (1) The representative representative of the case is: None (2) The symbol of the representative figure is simple: No 201221583 If there is a chemical formula in the case, please disclose the chemical formula that best shows the characteristics of the invention: no