JP5678519B2 - Fine yellow pigment composition, pigment dispersion containing the fine yellow pigment composition, and method for producing the fine yellow pigment composition - Google Patents

Description

  The present invention relates to a yellow pigment composition, and more particularly to a fine yellow pigment composition containing a refined yellow pigment.

  In printing inks and paints, such as ink for ink jet printers and color filter inks, the pigments are dispersed in a fine state to exert high coloring power, and the vivid color tone of color-extended products such as printed materials and coated products. In addition, it has appropriateness such as gloss, and appropriateness such as chromaticity and contrast ratio of a coating film such as a color filter. In recent years, higher sharpness, gloss, chromaticity, contrast ratio and the like have been demanded in these applications.

  As one of the countermeasures, a method of making the pigment fine is employed. However, in general, pigment particles once dispersed in a mixture of water, solvent, resin, etc. (vehicles such as paints and inks) tend to aggregate in the mixture (pigment dispersion). The smaller the particle diameter, the stronger the tendency to agglomerate to form secondary particles. Therefore, it is difficult to stably disperse the refined pigment particles even if the pigment is refined. When the pigment particles aggregate in the pigment dispersion in this way, various undesirable phenomena such as an increase in the viscosity of the pigment dispersion, a decrease in the gloss of the painted surface of the developed color, and a decrease in the performance of the coating film may occur. There are many.

  By the way, three colors of red, green, and blue are mainly used as color filter pigments, and yellow pigments are generally used in combination as these complementary colors. As such a yellow pigment, a quinophthalone pigment, which is considered to have good heat resistance and weather resistance, is known. The same applies to other uses other than color filters).

  As an improvement measure, a method using a quinophthalone pigment having a specific type of crystal structure (Patent Document 1) and a method using a quinophthalone 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 these techniques are used, there is still room for improvement in terms of, for example, improving the contrast ratio when used as an ink for a coating film such as a color filter.

JP 2002-105351 A JP 2003-167112 A

  In view of the above problems, an object of the present invention is to provide a fine yellow pigment composition capable of improving the contrast ratio when used as an ink for a coating film such as a color filter.

  As a result of intensive studies, the present inventors have found that the above problems can be solved by using a quinophthalone pigment and a plurality of specific pigment derivatives, and have reached the present invention. That is, the gist of the present invention is as follows.

The first of the present invention relates to a fine yellow pigment composition comprising a quinophthalone pigment, a sulfonated quinophthalone pigment derivative, and a triazine pigment derivative represented by the following formula (1).

(In the formula (1), A represents an aromatic amine residue represented by the following formula (2), and B represents a chlorine atom, a hydroxyl group, a sulfanilic acid residue or an alternic acid residue.)

(In formula (2), Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent —H, a halogen atom, a lower alkyl group or a lower alkoxy group. X represents —H, —OH or Represents —NH ₂ , W represents —CH ₂ — , and m and n are each independently 0 or 1.)

The second of the present invention relates to a pigment dispersion containing the fine yellow pigment composition , a solvent, a dispersant, a dispersion resin, and other pigments .

A third aspect of the present invention is a method for producing the fine yellow pigment composition, wherein a mixture containing a quinophthalone pigment, the sulfonated quinophthalone pigment derivative and the triazine pigment derivative is ground at 60 ° C. or less. The present invention relates to a method for producing a fine yellow pigment composition comprising a step of kneading to refine the quinophthalone pigment .

  The fine yellow pigment composition according to the present invention can improve the contrast ratio of the coating film when used as an ink for a coating film such as a color filter.

  According to the method for producing a fine yellow pigment composition according to the present invention, the fine yellow pigment composition can be easily produced.

  The fine yellow pigment composition according to the present invention includes a quinophthalone pigment, a sulfonated quinophthalone pigment derivative, and a triazine pigment derivative represented by the above formula (1).

  As the quinophthalone pigment, the color index (hereinafter abbreviated as CI) number is C.I. I. Pigment Yellow 138 (hereinafter abbreviated as PY138) is representative and is represented by the following formula (4). A well-known thing can be used as PY138, for example, Palitool Yellow D0960 by BASF Corporation etc. can be illustrated.

  In the present invention, the primary particle diameter of the pigment is preferably in the range of 20 to 60 μm from the viewpoint of ensuring dispersibility of the pigment and improving the contrast ratio.

  The sulfonated quinophthalone pigment derivative (hereinafter sometimes simply referred to as “sulfonated pigment derivative”) is obtained by subjecting a quinophthalone pigment or the pigment derivative to sulfonation. . The sulfonation treatment can be performed by, for example, the method described in JP-A-2009-126994 and other known methods.

  In the present invention, the sulfonic acid obtained by the above method may be used as it is, or may be used as a salt of the sulfonic acid. Examples of the compound or atom that forms a salt with the sulfonic acid include, for example, 1 to 3 metal atoms such as lithium, potassium, sodium, calcium, magnesium, strontium, and aluminum, monoalkylamines such as ethylamine and butylamine, and dimethylamine. And dialkylamines such as diethylamine, trialkylamines such as trimethylamine and triethylamine, monoethanolamines, organic amines such as alkanolamines such as diethanolamine and triethanolamine, and ammonia.

  In addition, when the salt is an alkali metal salt, the salt becomes water-soluble, and after dissolving the salt in water, the water-insoluble impurities can be easily separated by simply filtering. Derivatives can be obtained with high purity.

  Examples of the sulfonated quinophthalone pigment derivative used in the present invention include those having a chemical structure represented by the following formula (5) and salts thereof.

(In formula (5), p represents an integer of 1 to 5. X ^{1 to} X ⁸ each independently represents a hydrogen atom or a halogen atom.)

  The sulfonated pigment derivative having such a structure has an appropriate affinity with the quinophthalone pigment because the plane due to the quinoline structure and the plane due to the phthalimide structure are in a non-parallel state. It is considered that the aggregation of pigment particles is suppressed. In addition, the sulfonated pigment derivative has a high affinity with the triazine pigment derivative as will be described later, and it is considered that both of them can effectively exert the action on the quinophthalone pigment. Furthermore, since it has a sulfo group in the molecule, it is excellent in dispersibility in the solvent described later, and is considered to function effectively when preparing a pigment dispersion.

In the present invention, a sulfonated quinophthalone pigment derivative represented by the above formula (5) may be used, and among them, it is preferable that all of X ^{1 to} X ⁸ are chlorine atoms. Thereby, the affinity with the quinophthalone pigment represented by the above formula (4) is improved, the adsorption of the derivative to the pigment particles is promoted, and more effective prevention of crystal growth can be expected.

Any triazine pigment derivative may be used as long as it has a structure represented by the above formula (1). The triazine pigment derivative having such an aromatic amine residue is a π electron-rich compound, the compound approaches the surface of the quinophthalone pigment crystal particle, and interaction with the π electron that the pigment molecule has, It is considered that the crystal growth of primary particles of the quinophthalone pigment can be suppressed / controlled in the miniaturization process described later.
The triazine pigment derivative also interacts with the π-electron of the sulfonated pigment derivative molecule, so both have a high affinity and are considered to be able to effectively exert their effects on the quinophthalone pigment. It is done.
Furthermore, since it has a sulfo group in the molecule as in the case of the sulfonated pigment derivative, it has excellent dispersibility in the solvent described later and is considered to function effectively when preparing a pigment dispersion. .

  In the present invention, a triazine pigment derivative represented by the above formula (1) may be used, but A, which is an aromatic amine residue of the triazine pigment derivative, is a group represented by the above formula (2). Is preferred. In the present invention, “lower” in the lower alkyl group and lower alkoxy group means one having 1 to 4 carbon atoms. In the case of such carbon number, it is considered that the steric hindrance is low and the affinity with the pigment is further improved.

  Specific examples of the group represented by (2) above include any of the groups represented by formulas (6) to (8) from the viewpoint of suppressing the crystal growth of the quinophthalone pigment and reducing the primary particle diameter. preferable.

  Such a triazine pigment derivative can be produced by a known method, or a commercially available product may be used.

  In the fine pigment composition of the present invention, the content of the sulfonated pigment derivative is not particularly limited, but from the viewpoint of improving the contrast ratio of the coating film, it is 2 to 20 parts by weight with respect to 100 parts by weight of the quinophthalone pigment. It is preferably 5 to 10 parts by weight. The content of the triazine pigment derivative is not particularly limited, but is preferably 1 to 10 parts by weight with respect to 100 parts by weight of the quinophthalone pigment from the viewpoint of improving the contrast ratio of the coating film. More preferably, it is 5 parts by weight.

  If necessary, the fine yellow pigment composition of the present invention may contain a dispersant, a resin and the like in addition to the pigment and the pigment derivative.

  The fine yellow pigment composition of the present invention can be obtained through a step of milling and kneading a mixture containing a quinophthalone pigment, the sulfonated quinophthalone pigment derivative and the triazine pigment derivative at 60 ° C. or less. .

  As described above, PY138 has good heat resistance and weather resistance. For example, in Patent Document 1, the wet milling temperature is preferably 80 ° C. or higher. However, the present inventors have found that the contrast ratio of a coating film such as a color filter can be further improved by performing kneading and kneading at a relatively low temperature as described above.

  In addition, by kneading and kneading a quinophthalone pigment using a plurality of specific pigment derivatives described above, the crystal growth of pigment particles is effectively suppressed, and the contrast ratio of a coating film such as a color filter is finally increased. It was found that it can be improved.

  In the present invention, the kneaded material may be milled and kneaded at a temperature as low as 60 ° C. or lower. However, from the viewpoint of improving the contrast ratio, 20 ° C. or higher is more preferable, and 30 to 50 ° C. is more preferable. Thus, by kneading and kneading at a lower temperature, it is possible to increase the viscosity of the kneaded product, to easily apply a shearing force to the kneaded product, and to contribute to the refinement of the pigment. When milling and kneading is performed at a temperature lower than 20 ° C., the primary particle diameter of the pigment becomes too small, and aggregates when the pigment dispersion is prepared to increase the viscosity, which may affect the contrast ratio of the coating film.

  The method for producing the fine yellow pigment composition of the present invention will be described based on a preferred example using a wet milling method, but is not limited thereto, and may be performed at a specific temperature. For example, other known methods such as a dry milling method may be used.

  In this example, first, the quinophthalone pigment, the sulfonated pigment derivative, the triazine pigment derivative, a water-soluble inorganic salt, and a water-soluble organic solvent are mixed and premixed by a mixer such as a super mixer. In this case, the mixing ratio is 2 to 20 parts by weight of the sulfonated pigment derivative, 1 to 10 parts by weight of the triazine pigment derivative, 500 to 1500 parts by weight of a water-soluble inorganic salt, and 100 parts by weight of water. The organic solvent is preferably 100 to 400 parts by weight.

  As the water-soluble inorganic salt, those known as grinding aids such as sodium chloride and (anhydrous) sodium sulfate ((anhydrous) sodium sulfate) can be appropriately used. The particle size of the inorganic salt is not particularly limited, but from the viewpoint of making the pigment finer, a particle size of 50 μm or less, preferably 10 μm or less is used. Moreover, you may use what was refined | miniaturized and sized as described in Unexamined-Japanese-Patent No. 2009-263501.

  As the water-soluble organic solvent, a known organic solvent used in salt milling can be used. Examples thereof include diethylene glycol (DEG), ethylene glycol, polyethylene glycol, propylene glycol, and glycerin, but are not limited thereto. Not.

  Next, the mixture obtained by performing the above preliminary mixing is supplied to a kneader, and grinding and kneading is performed while adjusting the temperature of the mixture (kneaded material) to 60 ° C. or less. At this time, the temperature of the kneaded product is determined with respect to the kneaded product being milled and kneaded in the kneading tank in the case of a batch-type kneader, and the kneaded product discharged from the outlet of the kneader in the case of a continuous kneader. Is measured by contacting a calibrated thermometer.

  As the kneader, any known kneader can be used as long as the temperature can be adjusted. Specifically, a batch kneader such as a kneader or a continuous kneader can be used. From the viewpoint of temperature control of the mixture during milling and kneading, it is preferable to use a continuous kneader. Examples of the continuous kneader include a biaxial continuous kneader described in JP-A-9-263723, a continuous kneader described in JP-A 2006-77062, and the like. The company-made Miracle KCK can be mentioned.

  Furthermore, the milled and kneaded product obtained by milling and kneading as described above is washed with ion-exchanged water or the like to obtain a fine pigment paste. Then, if necessary, the fine pigment paste after washing with water is dried with a dryer to obtain a fine pigment dry block, which is pulverized with a known pulverizer to obtain a fine pigment powder.

  In the present invention, the fine pigment paste obtained as described above or the fine pigment powder is used as the fine yellow pigment composition.

The pigment dispersion of the present invention contains the fine yellow pigment composition.
In addition to the fine yellow pigment composition, the pigment dispersion appropriately includes a solvent, a dispersant, a dispersion resin, other pigments (including pigment derivatives), and other components. Each of these components can be appropriately selected from known ones, and the outline thereof will be described below. In addition, the details can be appropriately used, for example, those described in JP2009-126994A.

As the solvent, a water-soluble solvent is preferably used. By using a water-soluble solvent as the solvent, the dispersibility of the pigment can be made particularly excellent. As the water-soluble solvent, a hydrophilic solvent can be used. Specifically, for example, a liquid having a solubility in 100 g of water at 25 ° C. of 3 g or more can be used.
As the water-soluble solvent, generally, a compound having a highly hydrophilic functional group such as a hydroxyl group, a compound having a polyglycol skeleton, or the like can be preferably used. For example, diethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PMA) and the like can be mentioned.
In the present invention, a water-insoluble solvent may be used.

Although it does not specifically limit as said dispersing agent, For example, a polymeric dispersing agent can be used. Examples of the polymer dispersant include basic polymer dispersants, neutral polymer dispersants, acidic polymer dispersants, and the like. Examples of such polymeric dispersants include, for example, dispersants made of acrylic and modified acrylic copolymers, urethane dispersants, polyaminoamide salts, polyether esters, phosphate esters, and aliphatic polycarboxylic acids. And the like, and the like.
Although the content rate of the dispersing agent in a pigment dispersion is not specifically limited, It is preferable that it is 2-28 wt%, and it is more preferable that it is 9-25 wt%.

Examples of the dispersion resin include alginic acids, polyvinyl alcohol, hydroxypropyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, styrene-acrylic acid resin, styrene-acrylic acid-acrylic ester resin, styrene-maleic acid resin, styrene- Maleic acid half ester resin, methacrylic acid-methacrylic acid ester resin, acrylic acid-acrylic acid ester resin, isobutylene-maleic acid resin, rosin-modified maleic acid resin, polyvinylpyrrolidone, gum arabic starch, polyallylamine, polyvinylamine, polyethyleneimine, etc. 1 type or 2 types or more selected from these can be used in combination.
Although the content rate of the dispersion resin in a pigment dispersion is not specifically limited, It is preferable that it is 2-21 wt%, and it is more preferable that it is 6-19.5 wt%.

As the other pigments, various known pigments and pigment derivatives thereof can be used. These pigments and pigment derivatives may be used alone or in combination of two or more.
The content of the pigment (the yellow fine pigment composition of the present invention and all other pigments (including pigment derivatives)) in the pigment dispersion is preferably 10 wt% or more, and preferably 10 to 25 wt%. Is more preferable.

  Examples of the other components include a vehicle, a pH adjuster, an antioxidant, an ultraviolet absorber, an antiseptic, and an antifungal agent. These can be added appropriately as long as the effects of the present invention are not hindered.

The pigment dispersion of the present invention can be prepared by a known method. Although the suitable example of the embodiment is demonstrated easily below, it is not limited to this.
In this example, inorganic beads are added in a multistage manner to a mixed solution containing a fine yellow pigment composition, a solvent, a dispersant, and a dispersion resin to perform a dispersion treatment. Thus, by adding inorganic beads in multiple stages, the fine pigment composition and the like can be efficiently dispersed in a fine state. If necessary, the other pigment and the other components may be added.

The inorganic beads are not particularly limited, and examples thereof include beads made of zirconia (for example, Toray ceramic crushed balls (trade name), manufactured by Toray Industries, Inc.).
The average particle diameter of the inorganic beads used in each stage is not particularly limited, but it is preferable to decrease the average particle diameter sequentially. For example, when adding inorganic beads in two stages, the average particle diameter of the first stage inorganic beads is 0.5 to 3.0 mm, and the second stage is 0.03 to 0.3 mm. .
The amount of inorganic beads added in each stage is not particularly limited, but is preferably 300 to 500 parts by weight with respect to 100 parts by weight of the mixed solution. Moreover, if it is the said range, the addition amount in each stage may be the same or different.

  The disperser that performs the dispersion treatment is not particularly limited, and examples thereof include a media-type disperser such as a pearl mill, and a uniaxial or biaxial mixer such as a disper mill. The treatment time is not particularly limited but is preferably 10 to 120 minutes. Moreover, there is no limitation in particular as the rotation speed of the stirring blade of a disperser, However, It is preferable that it is 1000-5000 rpm. Note that the types and conditions of these devices may be appropriately selected in each stage.

  The number of stages for adding the inorganic beads is not particularly limited, but it is preferable to add them in two stages. Further, in this example, after removing the inorganic beads added at each stage, other inorganic beads are added at the subsequent stage. However, as a method for removing the inorganic beads, it may be performed by a known method such as filtration. .

The pigment dispersion of the present invention is a dispersion-treated mixed liquid obtained by adding and dispersing the inorganic beads in multiple stages under the above conditions and removing the inorganic beads added in the final stage.
The pigment dispersion of the present invention is used, for example, for various paints, various printing inks such as offset printing and gravure printing, coating film inks (colorants for films) such as color filters, and lens coating materials. it can.

  The pigment dispersion of the present invention can be used for forming a coating film. For example, the coating film is applied with a pigment dispersion on the substrate by a method such as bar coating, spin coating, roll coating, slit coating, brush coating, offset printing, or gravure printing, and then dried (de-coated) as necessary. The target coating film can be formed by solvent treatment.

  Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples.

(Production Example 1) Preparation of Triazine Pigment Derivative (A) Sulfanilic acid (trade name: ASA sulfanilic acid, manufactured by Sugai Chemical Industry Co., Ltd.) reacting with 7.3 g of cyanuric chloride and 1 Cl of cyanuric chloride in 100 parts of water 6.8 g was added and reacted at 20 ° C. for 1 hour. Next, 10 g of 4,4′-methylenedi-2,6-xylidine (trade name: KAYABOND C-200S, manufactured by Nippon Kayaku Co., Ltd.) in an amount capable of reacting with one Cl of the reaction product was added, and 1 at 70 ° C. Reacted for hours. The obtained reaction product was filtered, and the residue was washed with water, and then left to stand overnight in a constant temperature bath at 80 ° C. and dried to obtain 17.0 g of a triazine derivative (A) represented by the following formula (9). It was.

Production Example 2 Preparation of Triazine Pigment Derivative (B) 10 g of 3,3′-dichlorobenzidine is added to 100 g of water, dispersed, and 7.3 g of cyanuric chloride reacting with one amino group is added. The reaction was carried out at 20 ° C. for 1 hour. Next, 13.7 g of sulfanilic acid was added and reacted at 90 ° C. for 1 hour to obtain 26.6 g of a triazine pigment derivative (B) having the structure of the following formula (10).

Example 1
500 g of Yellow 138 (trade name “Pariotol Yellow L0960HD, manufactured by BASF Corporation) as a quinophthalone pigment, 5000 g of anhydrous sodium sulfate (average particle diameter of about 5 μm, anhydrous sodium sulfate described in JP-A-2009-263501), water-soluble organic As a solvent, 1045 g of ethylene glycol, 50 g of the sulfonated pigment derivative represented by the following formula (11), and 25 g of the triazine pigment derivative (A) of Production Example 1 were uniformly mixed with a super mixer (manufactured by Kawata, Super Mixer SMV- 20) and premixed for about 2 minutes.
This mixture was supplied to a continuous kneader (Miracle KCK32 manufactured by Asada Tekko). The kneading conditions were as follows: the extrusion amount was 6.6 kg / h, the rotation speed was 90 rpm, and the kneaded material was milled and kneaded while controlling the temperature so that the temperature of the kneaded product was 45 ° C. 1300 g of the milled and kneaded product was stirred and dispersed in 8000 g of ion-exchanged water at 40 ° C., then transferred to Nutsche, filtered, and washed with water until the salt cake was removed to obtain a pigment water paste.
The pigment water paste was dried at 60 ° C. for 20 hours. The dried product was pulverized with a pulverizer (manufactured by Kyoritsu Riko Co., Ltd., small pulverizer sample mill SK-M2), and about 90 g of a fine yellow pigment composition containing a quinophthalone pigment, a sulfonated pigment derivative, and a triazine pigment derivative was obtained. Obtained.

(In Formula (11), p is an integer of 1-5.)

(Example 2)
A fine yellow pigment composition containing a quinophthalone pigment, a sulfonated pigment derivative, and a triazine pigment derivative in the same manner as in Example 1 except that the triazine derivative (B) was used instead of the triazine derivative (A). About 90 g was obtained.

Example 3
A fine yellow pigment composition containing a quinophthalone pigment, a sulfonated pigment derivative, and a triazine pigment derivative in the same manner as in Example 1 except that the kneaded product was milled and kneaded while controlling the temperature so that the temperature of the kneaded product was 30 ° C. About 90 g of product was obtained.

Example 4
A fine yellow pigment composition containing a quinophthalone pigment, a sulfonated pigment derivative, and a triazine pigment derivative in the same manner as in Example 1 except that the kneaded product was milled and kneaded while controlling the temperature so that the temperature of the kneaded product was 50 ° C. About 90 g of product was obtained.

(Comparative Example 1)
About 90 g of a fine yellow pigment composition containing a quinophthalone pigment and a sulfonated pigment derivative was obtained in the same manner as in Example 1 except that the triazine derivative was not added.

(Comparative Example 2)
About 90 g of a fine yellow pigment composition containing a quinophthalone pigment and a sulfonated pigment derivative was obtained in the same manner as in Comparative Example 1 except that the addition amount of the sulfonated pigment derivative was changed to 75 g.

(Evaluation)
<Preparation of pigment dispersion and coating film>
17.36 g of Fastogen GREEN A11O (manufactured by DIC) as a green pigment, 23.55 g of a fine yellow pigment composition of Examples and Comparative Examples as a complementary color pigment, 5.89 g of a sulfonated pigment derivative represented by the above formula (11) (above The content of the three products is referred to as the pigment component), Disperbyk LPN-6919 (manufactured by Big Chemie) 24.5 g as a dispersant, 27.6 g of SPCN-2000 (manufactured by Showa Polymer) as a dispersing resin, and 71.1 g of PMA as an organic solvent The mixture was put into a stirrer (uniaxial mixer) having an internal volume of 400 ml and stirred for 10 minutes. At this time, the rotation speed of the stirring blade of the stirrer was set to 2000 rpm.
Next, 640 g of inorganic peas having an average particle diameter of 0.8 mm (first inorganic peas, zirconia, Toray ceram crushed balls (trade name), manufactured by Toray Industries, Inc.) is added and stirred at room temperature for 30 minutes. First-stage distributed processing (first processing) was performed. At this time, the rotation speed of the stirring blade of the stirrer was set to 2000 rpm.
Next, the inorganic beads (first inorganic peas) are removed by filtration using a filter (“PALL HDCII Membrane Filter”, manufactured by PALL 杜), and then PMA is added so that the pigment content is 15 wt%. In addition, an inorganic peas having an average particle size of 0.1 mm (second inorganic peas, manufactured by Zirconia, “Toray ceram pulverized ball” (trade name), manufactured by Toray Industries, Inc.) is added by weight, and 4 times the total charge is added, The mixture was further stirred for 90 minutes to carry out the second stage dispersion treatment (second treatment). At this time, the rotation speed of the stirring blade of the stirrer was set to 2000 rpm.
Thereafter, the inorganic beads (second inorganic peas) were removed by filtration using a filter (“PALL HDCII Membrane Filter” (trade name), manufactured by PALL) to obtain a desired pigment dispersion.

  The pigment dispersion prepared as described above was used to prepare a thin coating plate (coating film) using spin coating (MIKASA SPINCENTER IH-DX2). The coating film was heated at 230 ° C. for 1 hour and subjected to the following evaluation.

(Evaluation)
Using the coating film prepared as described above, the Y value, x value, and contrast ratio (CR) were measured with a spectrophotometer (SPECTROTOPOMETER CM-3700d).
The method for measuring the contrast is as follows. That is, the color filter was sandwiched between two polarizing plates, and the transmitted light illuminance when the polarizing planes of the respective polarizing plates were made parallel to the transmitted light illuminance when perpendicularized were measured to obtain the ratio. For the measurement of transmitted light illuminance, a luminance meter “LS-100” (manufactured by Minolta) was used. Table 1 shows the measurement results. The column for evaluation in the table is a value when the y value is 0.55, and the contrast ratio (CR) is a relative ratio based on the value of Comparative Example 1.

As shown in Table 1, when a pigment dispersion obtained using a yellow fine pigment composition containing a sulfonated pigment derivative and a triazine pigment derivative prepared by kneading and grinding at a predetermined temperature is used, The contrast ratio of the coating film prepared from the pigment dispersion is improved. On the other hand, when the addition amount of the sulfonated pigment derivative is increased without using the triazine pigment derivative, the contrast ratio is greatly reduced.
Thus, the fine yellow pigment composition of the present invention is suitable for providing a coating film such as a color filter having an improved contrast ratio.

Claims (4)

A fine yellow pigment composition comprising a quinophthalone pigment, a sulfonated quinophthalone pigment derivative, and a triazine pigment derivative represented by the following formula (1).

(In the formula (1), A represents an aromatic amine residue represented by the following formula (2), and B represents a chlorine atom, a hydroxyl group, a sulfanilic acid residue or an alternic acid residue.)

(In Formula (2), Q ¹ , Q ² , Q ³ , and Q ⁴ each independently represent —H, a halogen atom, a lower alkyl group, or a lower alkoxy group. X represents —H, —OH, or Represents —NH ₂ , W represents —CH ₂ —, and m and n are each independently 0 or 1.)   The fine yellow pigment composition according to claim 1, wherein the quinophthalone pigment is refined by grinding and kneading a mixture containing the quinophthalone pigment, the sulfonated quinophthalone pigment derivative, and the triazine pigment derivative.   A pigment dispersion comprising the fine yellow pigment composition according to claim 1 and 2, a solvent, a dispersant, a dispersion resin, and other pigments.   The method for producing a fine yellow pigment composition according to claim 1 or 2, wherein a mixture comprising a quinophthalone pigment, the sulfonated quinophthalone pigment derivative and the triazine pigment derivative is ground at 60 ° C or less. A method for producing a fine yellow pigment composition comprising a step of kneading to refine the quinophthalone pigment.