JP5299151B2 - Fine pigment composition and method for producing the same - Google Patents

Fine pigment composition and method for producing the same Download PDF

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JP5299151B2
JP5299151B2 JP2009180130A JP2009180130A JP5299151B2 JP 5299151 B2 JP5299151 B2 JP 5299151B2 JP 2009180130 A JP2009180130 A JP 2009180130A JP 2009180130 A JP2009180130 A JP 2009180130A JP 5299151 B2 JP5299151 B2 JP 5299151B2
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pigment
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triazine compound
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JP2011032374A (en
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耕一 高原
博 谷垣
浩一 田中
雅史 伊藤
毅 西川
将吾 西俣
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Sanyo Color Works Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Filters (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

PURPOSE: A micro pigment composition is provided to effectively prevent the aggregation of pigment even when the composition is dispersed in a pigment dispersion composition and to form a thin film with excellent transparency. CONSTITUTION: A micro pigment composition comprises a triazine compound represented by formula (1) and organic pigments. In chemical formula (1), A represents an acid group or base group; B represents -OH, -Cl, acid group or base group; D represents -H, -Cl, -OH or aromatic amine moiety. A method for preparing the micro pigment composition comprises performing coupling reaction of diazonium salts with couplers in the presence of the triazine compound represented by formula (1).

Description

本発明は、微細な有機顔料を含む微細顔料組成物およびその製造方法に関するものである。   The present invention relates to a fine pigment composition containing a fine organic pigment and a method for producing the same.

印刷インキや塗料、例えばインクジェットプリンター用インキ、カラーフィルター用インキにおいては、顔料を微細な状態で分散させることにより、高い着色力を発揮させ、印刷物または塗加工物の鮮明な色調、光沢等の適性を持たせたり、カラーフィルター等の塗膜の色度、コントラスト等の適性を持たせたりしている。近年、高品質の印刷物等に対する市場の要請から、より一層微細な顔料粒子を分散して得られるインキ等が強く望まれている。   In printing inks and paints, such as inks for ink jet printers and color filter inks, the pigments are dispersed in a fine state to exert high coloring power and suitability for vivid colors, gloss, etc. Or having appropriateness such as chromaticity and contrast of a coating film such as a color filter. In recent years, there has been a strong demand for inks obtained by dispersing finer pigment particles because of market demand for high-quality printed materials.

そのため、顔料をより微細にするために、一旦得られた顔料をソルトミリング等の方法により、その一次粒子の粒子径をより小さくすることが広く行われている。
しかし、一般的には、水、溶剤、樹脂などの混合物（塗料やインキ等のビヒクル）中に一旦分散した顔料粒子は、その混合物（顔料分散体）中で凝集する傾向にあり、顔料の一次粒子の粒子径が小さくなるほど、凝集して二次粒子を形成する傾向が強いため、上記のようにソルトミリング等により顔料を微細化しても、微細化された顔料粒子を安定して分散させることは難しいこととされている。そして、このように顔料分散体中で顔料粒子が凝集すると、当該顔料分散体の粘度上昇、展色物の塗面光沢の低下、塗膜の性能の低下など、各種の好ましくない現象を生じることが多い。 Therefore, in order to make the pigment finer, it is widely practiced to reduce the particle diameter of the primary particles of the pigment once obtained by a method such as salt milling.
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, even if the pigment is refined by salt milling as described above, the refined pigment particles can be stably dispersed. Is considered difficult. 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.

この改善策として、金属石鹸などによる顔料の表面処理、あるいは、特定の顔料誘導体、有機色素の部分骨格を含む分散剤などの利用が提案されている（例えば、特許文献１〜３参照）。   As an improvement measure, use of a surface treatment of a pigment with metal soap or the like, or a dispersant containing a specific pigment derivative or a partial skeleton of an organic dye has been proposed (for example, see Patent Documents 1 to 3).

しかしながら、これらの技術によれば、顔料粒子の微細化と凝集性に関してある程度の改善効果は得られるものの、より微細な顔料粒子を分散したインキ等の要望に対して必ずしも満足しうるものが得られていないのが現状である。   However, according to these techniques, although some improvement effect can be obtained with respect to the refinement and agglomeration of the pigment particles, it is always possible to satisfy the demand for inks in which finer pigment particles are dispersed. The current situation is not.

米国特許第３５８２３８０号明細書US Pat. No. 3,582,380 特開平３−９９５７号公報Japanese Patent Laid-Open No. 3-9957 特開２００３−２６９５０号公報JP 2003-26950 A

上記問題に鑑みて、本発明の目的とするところは、一次粒子径が極めて小さい有機顔料を含み、かつその凝集が著しく抑制され得る微細顔料組成物を提供すること、および、当該微細顔料組成物を容易に調製可能な製造方法を提供することにある。   In view of the above problems, an object of the present invention is to provide a fine pigment composition containing an organic pigment having a very small primary particle diameter and capable of remarkably suppressing the aggregation, and the fine pigment composition. It is an object of the present invention to provide a production method capable of easily preparing the above.

本発明者らは、上記課題を解決するため、鋭意検討した結果、本発明に達した。即ち、本発明の第１は、式（１）で示されるトリアジン化合物と有機顔料とを含む微細顔料組成物に関する。   The inventors of the present invention have reached the present invention as a result of intensive studies to solve the above problems. That is, the first of the present invention relates to a fine pigment composition comprising a triazine compound represented by the formula (1) and an organic pigment.

Figure 0005299151
Figure 0005299151

（式（１）中、Ａは、式（７）で示される基から選択されるいずれかの酸性基又は−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（ＣＨ 3 ） 2 、−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（Ｃ 2 Ｈ 5 ） 2 、−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（Ｃ 3 Ｈ 7 ） 2 および−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（Ｃ 4 Ｈ 9 ） 2 から選択されるいずれかの塩基性基を示す。Ｂは、−ＯＨ又は−Ｃｌを示す。Ｄは、式（９）で示される一群の基のいずれかの芳香族アミン残基を示す。）
(In the formula (1), A represents any acidic group selected from the group represented by the formula (7), or —NH— (CH 2 ) 3 —N (CH 3 ) 2 , —NH— (CH 2 ) 3 -N (C 2 H 5 ) 2, -NH- (CH 2) 3 -N (C 3 H 7) 2 and -NH- (CH 2) is selected from 3 -N (C 4 H 9) 2 .B showing the Ruizure of basic groups, .D showing an -OH or -Cl represents any aromatic amine residue of a group of groups represented by the formula (9).)

Figure 0005299151
Figure 0005299151

（式（７）中、Ｒ(In formula (7), R 4Four 、Ｒ, R 5Five 、Ｒ, R 66 は、それぞれ独立して、−Ｈ、−ＮＯAre each independently -H, -NO 22 、−Ｃｌ、炭素数１〜４の低級アルキル基、炭素数１〜４の低級アルコキシル基、−ＣＦ, -Cl, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxyl group having 1 to 4 carbon atoms, -CF 3Three 、−ＳＯ, -SO 3Three Ｈ、−ＳＯH, -SO 22 Ｎ（ＣN (C 22 ＨH 5Five ）) 22 、−ＣＯＯＨ、−ＣＯＯＣＨ, -COOH, -COOCH 3Three 、−ＣＯＮＨ, -CONH 22 、−ＳＯ, -SO 22 −ＮＨ-NH 22 −Ｐｈ（Ｐｈはフェニル基を示す）、−ＣＯＮＨ−Ｐｈ（Ｐｈは、−Ｈ、−Ｃｌ、メチレン基の置換基を有して良いフェニル基を示す）のいずれかを示す。）-Ph (Ph represents a phenyl group) or -CONH-Ph (Ph represents a phenyl group which may have a substituent of -H, -Cl, or a methylene group). )

Figure 0005299151
Figure 0005299151

本発明では、前記有機顔料がアゾ系顔料あるいは縮合多環系顔料であってよく、アゾ系顔料としては、カラーインデックス ピグメントイエロー７４又はピグメントレッド２６９が好ましく、縮合多環系顔料としては、カラーインデックス ピグメントバイオレット２３又はピグメントレッド２５４が好ましい。   In the present invention, the organic pigment may be an azo pigment or a condensed polycyclic pigment, and the azo pigment is preferably Color Index Pigment Yellow 74 or Pigment Red 269, and the condensed polycyclic pigment is a color index. Pigment Violet 23 or Pigment Red 254 is preferable.

本発明の第２は、式（１）で示されるトリアジン化合物存在下で、ジアゾニウム塩をカップラーとカップリング反応させることを特徴とするアゾ系顔料を含む微細顔料組成物の製造方法に関する。また、本発明では、カップラー１００部に対し、前記トリアジン化合物が０．１〜２０部となるように添加してよい。   The second of the present invention relates to a method for producing a fine pigment composition containing an azo pigment, wherein a diazonium salt is subjected to a coupling reaction with a coupler in the presence of a triazine compound represented by the formula (1). Moreover, in this invention, you may add so that the said triazine compound may be 0.1-20 parts with respect to 100 parts of couplers.

本発明の第３は、式（１）で示されるトリアジン化合物存在下で、粗製顔料を顔料化することを特徴とする縮合多環系顔料を含む微細顔料組成物の製造方法に関する。また、本発明では、粗製顔料１００部に対し、前記トリアジン化合物が０．１〜２０部となるように添加してよい。   A third aspect of the present invention relates to a method for producing a fine pigment composition containing a condensed polycyclic pigment, wherein a crude pigment is pigmented in the presence of a triazine compound represented by the formula (1). Moreover, in this invention, you may add so that the said triazine compound may be 0.1-20 parts with respect to 100 parts of crude pigments.

本発明に係る微細顔料組成物は、特定のトリアジン化合物を含むことから、有機顔料の一次粒子径が極めて小さく、かつその凝集が著しく抑制され得るため、当該顔料組成物を顔料分散組成物中に分散させた場合でも、その凝集を効果的に防止することができる。従って、当該顔料分散組成物を用いて形成される薄膜は、透明性が極めて良好である。また、前記微細顔料組成物は、本発明に係る製造方法により容易に得ることができる。   Since the fine pigment composition according to the present invention contains a specific triazine compound, the primary particle diameter of the organic pigment is extremely small and the aggregation thereof can be remarkably suppressed. Therefore, the pigment composition is contained in the pigment dispersion composition. Even when dispersed, the aggregation can be effectively prevented. Therefore, the thin film formed using the pigment dispersion composition has very good transparency. The fine pigment composition can be easily obtained by the production method according to the present invention.

本発明の微細顔料組成物は、下式（１）で示されるトリアジン化合物と有機顔料とを含むことを特徴とする。   The fine pigment composition of the present invention comprises a triazine compound represented by the following formula (1) and an organic pigment.

Figure 0005299151
Figure 0005299151

（式（１）中、Ａは、酸性基又は塩基性基を示す。Ｂは、−ＯＨ、−Ｃｌ、酸性基又は塩基性基を示す。Ｄは、−Ｈ、−Ｃｌ、−ＯＨ又は芳香族アミン残基を示す。） (In the formula (1), A represents an acidic group or a basic group, B represents —OH, —Cl, an acidic group or a basic group. D represents —H, —Cl, —OH or aromatic. Group amine residue.)

本発明では、微細顔料組成物中に、前記式（１）で示されるトリアジン化合物が含まれることにより、有機顔料の一次粒子径が極めて小さく維持されることとなる。また、本発明の微細顔料組成物を用いて調製した顔料分散体は、他の分散剤などとの相乗効果により有機顔料の一次粒子の凝集が効果的に抑制されたものとなし得る。
このように、前記トリアジン化合物により微細な有機顔料の凝集が著しく抑制される機構は、必ずしも明らかではないが、トリアジン環を母体骨格として、その側鎖に酸性及び／又は塩基性の官能基を有することにより、前記トリアジン化合物が有機顔料の一次粒子表面へ吸着とトリアジン環のπ電子により、顔料粒子の結晶成長を抑制するとともに、分散剤等との親和性が飛躍的に向上するため、極めて良好な分散効果が奏されるものと考えられる。 In the present invention, when the triazine compound represented by the formula (1) is contained in the fine pigment composition, the primary particle diameter of the organic pigment is kept extremely small. In addition, the pigment dispersion prepared using the fine pigment composition of the present invention can be one in which agglomeration of the primary particles of the organic pigment is effectively suppressed by a synergistic effect with other dispersants and the like.
Thus, although the mechanism by which the aggregation of fine organic pigments is remarkably suppressed by the triazine compound is not necessarily clear, it has an acidic and / or basic functional group in its side chain with the triazine ring as a base skeleton. As a result, the triazine compound is adsorbed on the primary particle surface of the organic pigment and the pi electrons of the triazine ring suppress the crystal growth of the pigment particles, and the affinity with the dispersant is greatly improved. It is considered that a good dispersion effect is achieved.

式（１）中、Ｄは−Ｈ、−Ｃｌ、−ＯＨ又は芳香族アミン残基を示し、芳香族アミン残基としては、下記式（２）、（３）、（５）または（６）で示される基であるのが好ましい。このような芳香族アミン残基を有するトリアジン化合物は、π電子リッチな化合物であり、該化合物が形成されつつある顔料結晶粒子表面に接近し、該顔料分子が有するπ電子との相互作用により、顔料の一次粒子の結晶成長が抑制／制御できるものと考えられる。また、Ｄが−Ｃｌである場合は、トリアジン化合物が、π電子を有するトリアジン環により、形成されつつある顔料結晶粒子表面に近接し、該顔料分子が有するπ電子との相互作用により、顔料粒子表面に作用し、バルキーな塩素原子の動きと相俟って、顔料の一次粒子の結晶成長が抑制／制御できるものと考えられる。   In the formula (1), D represents —H, —Cl, —OH or an aromatic amine residue, and examples of the aromatic amine residue include the following formula (2), (3), (5) or (6). It is preferable that it is group shown by these. The triazine compound having such an aromatic amine residue is a π-electron rich compound, approaches the pigment crystal particle surface on which the compound is being formed, and interacts with the π electron that the pigment molecule has, It is considered that the crystal growth of the primary particles of the pigment can be suppressed / controlled. Further, when D is —Cl, the triazine compound is brought close to the surface of the pigment crystal particle being formed by the triazine ring having π electrons, and the pigment particles are caused to interact with the π electrons of the pigment molecules. It is considered that the crystal growth of the primary particles of the pigment can be suppressed / controlled in combination with the movement of the bulky chlorine atom acting on the surface.

Figure 0005299151
Figure 0005299151

（式（２）中、Ｙは、−Ｈ、−ＯＨ又は−ＮＨ2を示す。） (In formula (2), Y represents —H, —OH or —NH 2. )

Figure 0005299151
Figure 0005299151

（式（３）中、Ｑ1、Ｑ2、Ｑ3、Ｑ4は、それぞれ独立して、−Ｈ、ハロゲン原子、低級アルキル基又は低級アルコキシ基を示す。Ｘは、−Ｈ、−ＯＨ又は−ＮＨ2を示す。Ｗは、−ＣＨ2−、−Ｏ−、−ＳＯ2−又は式（４）を示し、ｎは、０〜２の整数を示す。） (In formula (3), 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 -NH 2 , W represents —CH 2 —, —O—, —SO 2 — or formula (4), and n represents an integer of 0 to 2.

Figure 0005299151
Figure 0005299151

Figure 0005299151
Figure 0005299151

（式（５）中、Ｒ1、Ｒ2、Ｒ3は、それぞれ独立して、−Ｈ、−Ｃｌ、−ＮＯ2、−ＮＨ2、低級アルキル基、低級アルコキシル基、−ＣＦ3、−ＳＯ3Ｈ、−ＳＯ2Ｎ（Ｃ2Ｈ5）2、−ＣＯＯＨ、−ＣＯＯＣＨ3、−ＣＯＮＨ2、−ＳＯ2−ＮＨ2−Ｐｈ（Ｐｈはフェニル基を示す）、−ＣＯＮＨ−Ｐｈ（Ｐｈは、−Ｈ、−Ｃｌ、メチレン基の置換基を有して良いフェニル基を示す）のいずれかを示す。） (In the formula (5), R 1 , R 2 and R 3 are each independently —H, —Cl, —NO 2 , —NH 2 , a lower alkyl group, a lower alkoxyl group, —CF 3 , —SO. 3 H, -SO 2 N (C 2 H 5) 2, -COOH, -COOCH 3, -CONH 2, -SO 2 -NH 2 -Ph (Ph represents a phenyl group), - CONH-Ph (Ph is , -H, -Cl, and a phenyl group which may have a substituent of a methylene group).

本発明において、低級アルキル基、低級アルコキシ基における低級とは、炭素数が１〜４であるものを意味する。   In the present invention, “lower” in the lower alkyl group and lower alkoxy group means one having 1 to 4 carbon atoms.

Figure 0005299151
Figure 0005299151

（式（６）中、Ｚ1、Ｚ2、Ｚ3、Ｚ4は、それぞれ独立して、−Ｈ、−Ｃｌ、−ＯＨ、−ＮＨ2、−ＳＯ3Ｈ、−ＣＯＯＨのいずれかを示す。） (In the formula (6), Z 1, Z 2, Z 3, Z 4 are respectively independently, -H, -Cl, -OH, -NH 2, -SO 3 H, any of the -COOH .)

本発明では、トリアジン化合物の芳香族アミン残基であるＤとしては、前記のような構成を満足すればよいが、有機顔料の結晶成長を抑制し、一次粒子径を小さくする観点からは、式（９）で示す一群の基のいずれかが好ましい。   In the present invention, D, which is an aromatic amine residue of the triazine compound, may satisfy the above-described configuration, but from the viewpoint of suppressing the crystal growth of the organic pigment and reducing the primary particle size, Any of the group of groups represented by (9) is preferred.

Figure 0005299151
Figure 0005299151

式（１）中、Ａは、酸性基又は塩基性基を示す。このような置換基であれば、特に限定はないが、酸性基としては、スルホン酸基又はカルボン酸基を有する基が好適であり、具体的には、π電子を有する芳香族基に酸性置換基を有する式（７）および（８）から選択されるいずれかの基であるのが好ましい。   In formula (1), A represents an acidic group or a basic group. The substituent is not particularly limited as long as it is such a substituent, but as the acidic group, a group having a sulfonic acid group or a carboxylic acid group is preferable. Specifically, an acidic substitution is performed on an aromatic group having π electrons. It is preferably any group selected from formulas (7) and (8) having a group.

Figure 0005299151
Figure 0005299151

Figure 0005299151
Figure 0005299151

（式（７）及び（８）中、Ｒ4、Ｒ5、Ｒ6は、それぞれ独立して、−Ｈ、−ＮＯ2、−Ｃｌ、低級アルキル基、低級アルコキシル基、−ＣＦ3、−ＳＯ3Ｈ、−ＳＯ2Ｎ（Ｃ2Ｈ5）2、−ＣＯＯＨ、−ＣＯＯＣＨ3、−ＣＯＮＨ2、−ＳＯ2−ＮＨ2−Ｐｈ（Ｐｈはフェニル基を示す）、−ＣＯＮＨ−Ｐｈ（Ｐｈは、−Ｈ、−Ｃｌ、メチレン基の置換基を有して良いフェニル基を示す）のいずれかを示す。） (In formulas (7) and (8), R 4 , R 5 and R 6 are each independently —H, —NO 2 , —Cl, a lower alkyl group, a lower alkoxyl group, —CF 3 , —SO. 3 H, -SO 2 N (C 2 H 5) 2, -COOH, -COOCH 3, -CONH 2, -SO 2 -NH 2 -Ph (Ph represents a phenyl group), - CONH-Ph (Ph is , -H, -Cl, and a phenyl group which may have a substituent of a methylene group).

また、塩基性基としては、アミン系塩基性基を有する基が好適であり、具体的には、−ＮＨ−（ＣＨ2）3−Ｎ（ＣＨ3）2、−ＮＨ−（ＣＨ2）3−Ｎ（Ｃ2Ｈ5）2、−ＮＨ−（ＣＨ2）3−Ｎ（Ｃ3Ｈ7）2および−ＮＨ−（ＣＨ2）3−Ｎ（Ｃ4Ｈ9）2から選択されるいずれかの塩基性基であるのが好ましい。 Further, as the basic group, a group having an amine-based basic group is preferable, and specifically, —NH— (CH 2 ) 3 —N (CH 3 ) 2 , —NH— (CH 2 ) 3 Any selected from —N (C 2 H 5 ) 2 , —NH— (CH 2 ) 3 —N (C 3 H 7 ) 2 and —NH— (CH 2 ) 3 —N (C 4 H 9 ) 2 These basic groups are preferred.

式（１）中、Ｂは、−ＯＨ、−Ｃｌ、酸性基又は塩基性基を示す。また、Ｂが酸性基又は塩基性基を示す場合は、それらについて、特に限定はないが、上述のＡにおいて示した、酸性基および塩基性基を、Ａとは独立して選択することができる。   In formula (1), B represents —OH, —Cl, an acidic group or a basic group. Moreover, when B shows an acidic group or a basic group, there is no limitation in particular about them, The acidic group and basic group which were shown in above-mentioned A can be selected independently of A. .

本発明では、以上のような構成を有するトリアジン化合物であれば、本発明の目的をたせいすることができるが、好適な例として、下式（１０）〜（１６）で示されるトリアジン化合物を挙げることができる。   In the present invention, the triazine compound having the above-described configuration can achieve the object of the present invention. As a preferable example, a triazine compound represented by the following formulas (10) to (16) is used. Can be mentioned.

Figure 0005299151
Figure 0005299151

Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151
Figure 0005299151

以上のような構成を有するトリアジン化合物は、公知の方法にて製造することができるほか、市販のものを用いても良い。   The triazine compound having the above-described configuration can be produced by a known method, or a commercially available product may be used.

本発明において用いる有機顔料としては特に限定はないが、アゾ系顔料または縮合系顔料が好適である。   The organic pigment used in the present invention is not particularly limited, but an azo pigment or a condensation pigment is preferable.

前記アゾ系顔料としては、本発明のトリアジン化合物による結晶抑制効果の観点から、カラーインデックス（以下、Ｃ．Ｉ．という） ピグメントイエロー１、３、１２、１３、１４、１７、５５、７３、７４、７５、８１、８３、９７、１２０、１５１、１５４、１５６、１６５、１７５、１８０、１９４、Ｃ．Ｉ．ピグメントレッド５、１４６、１４７、１５０、１７０、１７６、１８４、１８５、２１３、２６９が好ましく、中でも、Ｃ．Ｉ．ピグメントイエロー７４、Ｃ．Ｉ．ピグメントレッド２６９がより好ましい。   As the azo pigment, a color index (hereinafter referred to as CI) Pigment Yellow 1, 3, 12, 13, 14, 17, 55, 73, 74 is used from the viewpoint of the crystal suppression effect by the triazine compound of the present invention. 75, 81, 83, 97, 120, 151, 154, 156, 165, 175, 180, 194, C.I. I. Pigment Red 5, 146, 147, 150, 170, 176, 184, 185, 213, 269 are preferable. I. Pigment yellow 74, C.I. I. Pigment Red 269 is more preferable.

前記縮合多環系顔料としては、本発明のトリアジン化合物による結晶抑制効果の観点から、Ｃ．Ｉ．ピグメントレッド１２２、１７７、２０２、２０７、２０９、２５４、Ｃ．Ｉ．ピグメントブルー１５：３、１５：６、Ｃ．Ｉ．ピグメントグリーン３６、５８、Ｃ．Ｉ．ピグメントイエロー１３８、１５０、１８５、Ｃ．Ｉ．ピグメントバイオレット２３が好ましく、中でも、Ｃ．Ｉ．ピグメントレッド２５４、Ｃ．Ｉ．バイオレット２３がより好ましい。   Examples of the condensed polycyclic pigment include C.I. from the viewpoint of the crystal suppression effect by the triazine compound of the present invention. I. Pigment red 122, 177, 202, 207, 209, 254, C.I. I. Pigment blue 15: 3, 15: 6, C.I. I. Pigment green 36, 58, C.I. I. Pigment yellow 138, 150, 185, C.I. I. Pigment Violet 23 is preferable. I. Pigment red 254, C.I. I. Violet 23 is more preferable.

本発明において用いられる有機顔料は、１次粒子として、長径が、５０〜１５０ｎｍ、短径が、３０〜１００ｎｍであるのが好ましい。このような一次粒子の大きさを有するものを、本発明では、一次粒子径が極めて小さい、あるいは、高度に微細化された、という。   The organic pigment used in the present invention preferably has, as primary particles, a major axis of 50 to 150 nm and a minor axis of 30 to 100 nm. In the present invention, a particle having such a primary particle size is said to have a very small primary particle size or highly refined.

本発明の微細顔料組成物は、前述のトリアジン化合物の存在下で、所望の有機顔料の原料となる化合物を反応させるか、粗製顔料を顔料化することにより得ることができる。   The fine pigment composition of the present invention can be obtained by reacting a compound as a raw material of a desired organic pigment in the presence of the above-mentioned triazine compound or by pigmenting a crude pigment.

例えば、有機顔料としてアゾ系顔料を用いる場合は、前記トリアジン化合物の存在下で、原料となるジアゾニウム塩とカップラーとのカップリング反応を行うことで、カップリング反応によりアゾ系顔料が生成し、顔料の結晶が成長する際に、前記トリアジン化合物が、形成されつつある顔料結晶粒子表面に接近し、該顔料分子が有するπ電子との相互作用により、顔料の一次粒子の結晶成長が抑制／制御され、上述のように一次粒子径の極めて小さいアゾ系顔料を含む微細顔料組成物を得ることができると考えられる。尚、前記トリアジン化合物は、カップリング反応時に存在していれば良く、その添加方法は問わない。またカップリング反応は、公知の方法により行うことができる。尚、本発明において使用するカップラーとしては、上記アゾ系顔料を合成する際のカップリング反応において使用可能なものであれば特に限定はない。また、本発明において使用するジアゾニウム塩としては、上記アゾ系顔料のカップリング反応において使用可能なものであれば特に限定はなく、各種アミンをジアゾ化したジアゾニウムを金属塩としたものである。   For example, when an azo pigment is used as the organic pigment, an azo pigment is produced by a coupling reaction by performing a coupling reaction between a diazonium salt as a raw material and a coupler in the presence of the triazine compound. When the crystal grows, the triazine compound approaches the surface of the pigment crystal particle being formed, and the crystal growth of the primary particle of the pigment is suppressed / controlled by the interaction with the π electrons of the pigment molecule. As described above, it is considered that a fine pigment composition containing an azo pigment having an extremely small primary particle diameter can be obtained. The triazine compound may be present at the time of the coupling reaction, and the addition method is not limited. The coupling reaction can be performed by a known method. The coupler used in the present invention is not particularly limited as long as it can be used in the coupling reaction when synthesizing the azo pigment. Further, the diazonium salt used in the present invention is not particularly limited as long as it can be used in the coupling reaction of the azo pigment, and a diazonium obtained by diazotizing various amines is used as a metal salt.

また、前記トリアジン化合物の添加量は、特に限定はないが、カップラー１００部に対し、前記トリアジン化合物が０．１〜２０部となるように添加する。前記トリアジン化合物の添加量が、０．１部より少ないと、結晶成長抑制効果が小さく、２０部より多いと、最終製品の性能に影響を与える（最終製品の透明性、コントラストなど）傾向にある。また、カップラーとジアゾニウム塩の使用比率は、等モルの反応を基準とするが、それらの種類等によって適宜調整して良い。   The amount of the triazine compound added is not particularly limited, but is added so that the triazine compound is 0.1 to 20 parts with respect to 100 parts of the coupler. When the added amount of the triazine compound is less than 0.1 part, the crystal growth suppressing effect is small, and when it is more than 20 parts, the performance of the final product is affected (transparency, contrast, etc. of the final product). . Moreover, although the use ratio of a coupler and a diazonium salt is based on equimolar reaction, you may adjust suitably according to those types.

上記のようにカップリング反応をさせた後、定法により濾過、水洗し、乾燥させた後、ロールミル、ビーズミルなどの分散機により粉砕することにより、一次粒子の極めて小さいアゾ系顔料を含む微細顔料組成物を得ることができる。尚、上記のようにして、乾燥させた後は、一次粒子が凝集し、より大きな二次粒子が形成されるが、上記のような分散機を用いるだけで、通常必要とされるソルトミリングなどの微細化工程を経ることなく、容易に二次粒子を粉砕して、粒子径の極めて小さい一次粒子の状態に戻すことが可能である。   After the coupling reaction as described above, it is filtered, washed with water by a conventional method, dried, and then pulverized with a disperser such as a roll mill, a bead mill, etc., so that a fine pigment composition containing an azo pigment having extremely small primary particles You can get things. In addition, after drying as described above, primary particles agglomerate and larger secondary particles are formed. Salt milling ordinarily required only by using a disperser as described above. The secondary particles can be easily pulverized and returned to the state of primary particles having a very small particle size without going through the above-mentioned refinement process.

有機顔料として縮合多環系顔料を用いる場合は、アゾ系顔料の場合と異なり、前記トリアジン化合物の存在下で、粗製顔料を顔料化する工程を経て微細顔料組成物が製造される。これは、粗製顔料を調製する際に前記トリアジン化合物を添加することが困難であることによるものである。そこで、一次粒子径の非常に大きい粗製顔料が調製された後、顔料化（微細化）する工程において、前記トリアジン化合物を存在させると、微細化された顔料粒子の結晶成長が効果的に抑制され、一次粒子の極めて小さい縮合多環系顔料が得られることを見出した。基本的な原理は、アゾ系顔料の場合と同じく、前記トリアジン化合物と顔料のπ電子による相互作用およびその側鎖の構成によるものと考えられる。即ち、一旦調製された非常に大きな粒子径を有する粗製顔料を、ソルトミリング等の方法で、顔料粒子が微細にされた後、再度結晶が成長していくことになるが、その際に、前記トリアジン化合物を存在させることによって、その結晶成長が効果的に抑制されるものと考えられる。
尚、本発明で粗製顔料とは、縮合多環系顔料のもととなる原料化合物を反応させて得られる、粒子径の大きい（例えば、１０〜数百μｍ程度）化合物であって、そのままでは顔料としての分散性や鮮明な発色が得られないものをいう。このような縮合多環系顔料の粗製顔料は公知の方法で調製することができる。 When a condensed polycyclic pigment is used as the organic pigment, unlike the case of an azo pigment, a fine pigment composition is produced through a step of pigmenting a crude pigment in the presence of the triazine compound. This is because it is difficult to add the triazine compound when preparing a crude pigment. Therefore, in the step of pigmentation (miniaturization) after the preparation of a crude pigment having a very large primary particle diameter, the crystal growth of the miniaturized pigment particles is effectively suppressed when the triazine compound is present. It was found that a condensed polycyclic pigment having extremely small primary particles can be obtained. As in the case of the azo pigment, the basic principle is considered to be due to the interaction of the triazine compound and the pigment by π electrons and the structure of the side chain. That is, once a crude pigment having a very large particle diameter is prepared, a crystal is grown again after the pigment particles are refined by a method such as salt milling. The presence of the triazine compound is considered to suppress the crystal growth effectively.
In the present invention, the crude pigment is a compound having a large particle size (for example, about 10 to several hundred μm) obtained by reacting a raw material compound that is a basis for the condensed polycyclic pigment, This means that dispersibility as a pigment and clear color development cannot be obtained. Such a crude condensed polycyclic pigment can be prepared by a known method.

本発明では、上記のような粗製顔料を、前記トリアジン化合物の存在下で顔料化する。本発明で顔料化するとは、粗製顔料の粒子径を顔料として適切な粒子径範囲に揃える工程を意味する。また、適切な粒子範囲とは、用途などによって異なるが、０．０５〜０．３μｍ程度とされている。   In the present invention, the crude pigment as described above is pigmented in the presence of the triazine compound. Pigmentation in the present invention means a step of aligning the particle diameter of the crude pigment within an appropriate particle diameter range as a pigment. Moreover, although it changes with uses etc. with an appropriate particle range, it is set as about 0.05-0.3 micrometer.

また、上記顔料化の方法としては、ソルトミリング等の公知の方法を用いて行うことができる。顔料化の際の前記トリアジン化合物の添加量は、特に限定はないが、粗製顔料１００部に対し、前記トリアジン化合物が０．１〜２０部となるように添加する。前記トリアジン化合物の添加量が、０．１部より少ないと、結晶成長抑制効果が小さく、２０部より多いと、最終製品の性能に影響を与える（最終製品の透明性、コントラストなど）傾向にある。   The pigmentation method can be performed using a known method such as salt milling. The amount of the triazine compound added during pigmentation is not particularly limited, but the triazine compound is added in an amount of 0.1 to 20 parts per 100 parts of the crude pigment. When the added amount of the triazine compound is less than 0.1 part, the crystal growth suppressing effect is small, and when it is more than 20 parts, the performance of the final product is affected (transparency, contrast, etc. of the final product). .

上記のようにして顔料化された後、定法により水洗し、乾燥させた後、ロールミル、ビーズミルなどの分散機により粉砕することにより、高度に微細化された、一次粒子径の極めて小さい縮合多環系顔料を含む微細顔料組成物を得ることができる。   After being pigmented as described above, it is washed with water by a conventional method, dried, and then pulverized with a disperser such as a roll mill or a bead mill, so that it is highly refined, and a condensed polycycle having a very small primary particle size. A fine pigment composition containing a pigment can be obtained.

上記のようにして得られた本発明に係る所定のトリアジン化合物と所望の有機顔料を含む微細顔料組成物は、所望の有機顔料が高度に微細化されており、例えば、有機顔料の１次粒子として、長径が、５０〜１５０ｎｍ、短径が３０〜１００ｎｍを有するものを得ることができる。また、このように、本発明に係る微細顔料組成物は、含まれる有機顔料の一次粒子が極めて小さく、高度に微細化されており、かつその凝集性を著しく抑制し得るものであ、即ち、当該顔料組成物を顔料分散組成物中に分散させた場合でも、分散剤等との相乗効果によりその凝集を効果的に防止することができるため、高度な色特性等が要求される印刷インキ、塗料など、とりわけインクジェットプリンター用インキ、カラーフィルター用インキなどに好適に用いることができる。   The fine pigment composition containing the predetermined triazine compound and the desired organic pigment according to the present invention obtained as described above has the desired organic pigment highly refined, for example, primary particles of the organic pigment. As described above, a material having a major axis of 50 to 150 nm and a minor axis of 30 to 100 nm can be obtained. Further, in this way, the fine pigment composition according to the present invention is such that the primary particles of the organic pigment contained are extremely small, highly refined, and can remarkably suppress the agglomeration, that is, Even when the pigment composition is dispersed in the pigment dispersion composition, it is possible to effectively prevent aggregation due to a synergistic effect with the dispersant and the like, so a printing ink that requires advanced color characteristics, It can be suitably used for paints, in particular, ink for ink jet printers, color filter inks, and the like.

以下に実施例および比較例を挙げて本発明をより詳細に説明する。尚、例中における「部」や「％」は重量基準である。
（製造例１）
水１００部に塩化シアヌル７．３部と塩化シアヌルの１個のＣｌと反応する量のスルファニル酸（商品名：ＡＳＡスルファニル酸、スガイ化学工業製）６．８部を加えて２０℃で１時間反応させた。次に、この反応物の１個のＣｌと反応する量の４，４’−メチレンジ−２，６−キシリジン（商品名：ＫＡＹＡＢＯＮＤ Ｃ−２００Ｓ、日本化薬製）１０部を加えて７０℃で１時間反応させた。得られた反応物を濾過、残渣を水洗した後、８０℃の恒温槽に１晩静置して乾燥させて、前記式（１０）で示されるトリアジン化合物１７．０部を得た。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. In the examples, “parts” and “%” are based on weight.
(Production Example 1)
Add 6.8 parts of sulfanilic acid (trade name: ASA sulfanilic acid, manufactured by Sugai Chemical Industry) in an amount to react with 7.3 parts of cyanuric chloride and one Cl of cyanuric chloride in 100 parts of water, and at 20 ° C. for 1 hour. Reacted. Next, 10 parts 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 is added and the mixture is added at 70 ° C. The reaction was carried out for 1 hour. The obtained reaction product was filtered and the residue was washed with water, and then allowed to stand overnight in a thermostatic bath at 80 ° C. and dried to obtain 17.0 parts of a triazine compound represented by the formula (10).

（製造例２）
スルファニル酸６．８部に替えて、スルファニル酸３．４部添加とした以外は、製造例１と同様の操作を行い、前記式（１１）で示されるトリアジン化合物１４．８部を得た。 (Production Example 2)
The same operation as in Production Example 1 was conducted except that 3.4 parts of sulfanilic acid was added instead of 6.8 parts of sulfanilic acid, to obtain 14.8 parts of a triazine compound represented by the formula (11).

（製造例３）
４，４’−メチレンジ−２，６−キシリジン１０部に替えて、パラフェニレンジアミン（商品名：ｐ−フェニレンジアミン、和光純薬製）４．３部添加とした以外は、製造例１と同様の操作を行い、前記式（１２）で示されるトリアジン化合物１２．５部を得た。 (Production Example 3)
The same as Production Example 1 except that 4.3 parts of paraphenylenediamine (trade name: p-phenylenediamine, manufactured by Wako Pure Chemical Industries) was added in place of 10 parts of 4,4′-methylenedi-2,6-xylidine. Thus, 12.5 parts of a triazine compound represented by the formula (12) was obtained.

（製造例４）
４，４’−メチレンジ−２，６−キシリジン１０部に替えて、３−アミノ−４−メトキシベンズアニライド（商品名：Ｍ−４０、三星化学工業製）９．５部添加とした以外は、製造例１と同様の操作を行い、前記式（１３）で示されるトリアジン化合物１６．６部を得た。 (Production Example 4)
In place of 10 parts of 4,4′-methylenedi-2,6-xylidine, 9.5 parts of 3-amino-4-methoxybenzanilide (trade name: M-40, manufactured by Samsung Chemical Industries) was added. The same operation as in Production Example 1 was performed to obtain 16.6 parts of a triazine compound represented by the formula (13).

（製造例５）
水１００部に塩化シアヌル７．３部と塩化シアヌルの１個のＣｌと反応する量のスルファニル酸６．８部を加えて２０℃で１時間反応させた。次に、この反応物の１個のＣｌと反応する量の３−アミノ−４−メトキシベンズアニライド（商品名：Ｍ−４０、三星化学工業製）９．５部を加えて７５℃で１時間反応させた。その後、水酸化ナトリウムを加えてｐＨ６に調製し、更に９０℃で２時間撹拌を行い、残りのＣｌを加水分解した。得られた反応物を濾過、残渣を水洗した後、８０℃の恒温槽に１晩静置して乾燥させて、前記式（１４）で示されるトリアジン化合物１５．９部を得た。 (Production Example 5)
To 100 parts of water, 7.3 parts of cyanuric chloride and 6.8 parts of sulfanilic acid in an amount capable of reacting with one Cl of cyanuric chloride were added and reacted at 20 ° C. for 1 hour. Next, 9.5 parts of 3-amino-4-methoxybenzanilide (trade name: M-40, manufactured by Samsung Chemical Industry Co., Ltd.) in an amount to react with one Cl of the reaction product was added, and 1 at 75 ° C. Reacted for hours. Thereafter, sodium hydroxide was added to adjust to pH 6, and the mixture was further stirred at 90 ° C. for 2 hours to hydrolyze the remaining Cl. 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 15.9 parts of a triazine compound represented by the formula (14).

（製造例６）
水１００部に塩化シアヌル７．３部と塩化シアヌルの１個のＣｌと反応する量のスルファニル酸６．８部を加えて２０℃で１時間反応させた。次に、この反応物の１個のＣｌと反応する量の４，４’−メチレンジ−２，６−キシリジン（商品名：ＫＡＹＡＢＯＮＤ Ｃ−２００Ｓ、日本化薬製）１０部を加えて７０℃で１時間反応させた。その後、水酸化ナトリウムを加えてｐＨ６に調製し、更に９０℃で２時間撹拌を行い、残りのＣｌを加水分解した。得られた反応物を濾過、残渣を水洗した後、８０℃の恒温槽に１晩静置して乾燥させて、前記式（１５）で示されるトリアジン化合物１６．４部を得た。 (Production Example 6)
To 100 parts of water, 7.3 parts of cyanuric chloride and 6.8 parts of sulfanilic acid in an amount capable of reacting with one Cl of cyanuric chloride were added and reacted at 20 ° C. for 1 hour. Next, 10 parts 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 is added and the mixture is added at 70 ° C. The reaction was carried out for 1 hour. Thereafter, sodium hydroxide was added to adjust to pH 6, and the mixture was further stirred at 90 ° C. for 2 hours to hydrolyze the remaining Cl. The obtained reaction product was filtered, and the residue was washed with water, and then allowed to stand overnight in a constant temperature bath at 80 ° C. and dried to obtain 16.4 parts of a triazine compound represented by the formula (15).

（製造例７）
スルファニル酸６．８部に替えて、ジブチルアミノプロピルアミン（商品名：Ｎ，Ｎ−ジブチル−１，３−プロパンジアミン、和光純薬製）７．３部添加とした以外は、製造例１と同様の操作を行い、前記式（１６）で示されるトリアジン化合物１７．４部を得た。 (Production Example 7)
Except that 6.8 parts of sulfanilic acid was replaced with 7.3 parts of dibutylaminopropylamine (trade name: N, N-dibutyl-1,3-propanediamine, manufactured by Wako Pure Chemical Industries), Production Example 1 and The same operation was performed to obtain 17.4 parts of a triazine compound represented by the formula (16).

（実施例１）
２−メトキシ−４−ニトロ−アニリン（商品名：Ｋａｋｏ Ｒｅｄ Ｂ Ｂａｓｅ ｃｏｎｃ、昭和化工製）５０部を、水４００部と３５％塩酸７９部との混合液中に加えて撹拌した後、この液が０〜５℃になるまで冷却し、さらに亜硝酸ソーダ２１．５部を加えて定法によりジアゾ化し、ジアゾ化液を調製した。
また、カップラー液は、次のようにして調製した。先ず、カップラーである２−メトキシ−アセトアセトアニライド（商品名：アセト酢酸Ｏ−アニシダイト、三星化学工業製）６６部を、水３００部と３０重量％苛性ソーダ水溶液４８部との混合液中に加えて溶解させた。そして、この溶解液を、水９００部に酢酸ソーダ３０部を添加して得られる水溶液に加えた後、水１５０部と８０％酢酸２８部との混合液を更に加えて、カップラーを析出させた。次いで、この析出液に、製造例１で得られたトリアジン化合物３部を添加して懸濁液（カップラー液）を調製した。
このカップラー液に前記ジアゾ化液を２５℃において撹拌しながら１２０分間かけて徐々に添加して、ジアゾニウム塩をカップラーとカップリング反応をさせた後、９０℃で３０分間加熱し、アゾ系黄色顔料Ｃ．Ｉ．ピグメントイエロー７４を生成した。
この反応液を常温で放置後、定法により濾過し、水洗し、乾燥させた後、サンプルミルにより粉砕して、式（１０）で示されるトリアジン化合物とアゾ系黄色顔料Ｃ．Ｉ．ピグメントイエロー７４を含む微細顔料組成物１１８部を得た。 Example 1
50 parts of 2-methoxy-4-nitro-aniline (trade name: Kako Red B Base conc, manufactured by Showa Kako) was added to a mixed liquid of 400 parts of water and 79 parts of 35% hydrochloric acid, and this liquid was stirred. Was cooled to 0 to 5 ° C., 21.5 parts of sodium nitrite was further added, and diazotized by a conventional method to prepare a diazotized liquid.
The coupler liquid was prepared as follows. First, 66 parts of 2-methoxy-acetoacetanilide (trade name: acetoacetic acid O-anisidite, manufactured by Samsung Chemical Industry), which is a coupler, is added to a mixed solution of 300 parts of water and 48 parts of a 30% by weight aqueous caustic soda solution. And dissolved. Then, this solution was added to an aqueous solution obtained by adding 30 parts of sodium acetate to 900 parts of water, and then a mixed solution of 150 parts of water and 28 parts of 80% acetic acid was further added to precipitate the coupler. . Next, 3 parts of the triazine compound obtained in Production Example 1 was added to this precipitation solution to prepare a suspension (coupler solution).
The diazotized liquid is gradually added to the coupler liquid over a period of 120 minutes while stirring at 25 ° C., and the diazonium salt is allowed to undergo a coupling reaction with the coupler, followed by heating at 90 ° C. for 30 minutes to obtain an azo yellow pigment. C. I. Pigment Yellow 74 was produced.
The reaction solution was allowed to stand at room temperature, then filtered by a conventional method, washed with water, dried, and then pulverized by a sample mill to obtain a triazine compound represented by the formula (10) and an azo yellow pigment C.I. I. 118 parts of a fine pigment composition containing CI Pigment Yellow 74 were obtained.

（実施例２）
３−アミノ−４−メトキシベンズアニライド（商品名：Ｍ−４０、三星化学工業製）５０部を、水１０００部に添加し、分散させ、液温を０〜５℃に調整して、３５％塩酸７８部を加えて２０分間撹拌した後、亜硝酸ソーダ１５部を加えて定法によりジアゾ化した。更に、８０％酢酸２５部及び酢酸ソーダ１５部を添加してジアゾニウム塩を生成させた後、製造例１で得られたトリアジン化合物１部を添加し、ジアゾニウム塩溶液を調製した。
また、Ｎ−（５−クロロ−２−メトキシフェニル）−３−ヒドロキシ−２−ナフタレンカルボキシアミド（商品名：ナフトール ＡＣ−ＣＡ、三星化学工業製）６９部を、水１７００部と３０重量％苛性ソーダ水溶液４８部の混合液に溶解し、カップラー液を調製した。
このカップラー液を、液温が１０℃以下になるように調整し、前記ジアゾニウム塩溶液に撹拌しながら添加してカップリング反応をさせた後、９０℃で３０分間加熱し、アゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を生成した。
この反応液を常温で放置後、定法により濾過し、水洗し、乾燥させた後、サンプルミルにより粉砕して、式（１０）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 2)
50 parts of 3-amino-4-methoxybenzanilide (trade name: M-40, manufactured by Samsung Chemical Industry Co., Ltd.) is added to 1000 parts of water and dispersed, and the liquid temperature is adjusted to 0 to 5 ° C. After adding 78 parts of hydrochloric acid and stirring for 20 minutes, 15 parts of sodium nitrite was added and diazotized by a conventional method. Further, 25 parts of 80% acetic acid and 15 parts of sodium acetate were added to form a diazonium salt, and then 1 part of the triazine compound obtained in Production Example 1 was added to prepare a diazonium salt solution.
Further, 69 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide (trade name: Naphthol AC-CA, manufactured by Samsung Chemical Industry), 1700 parts of water and 30% by weight of caustic soda A coupler solution was prepared by dissolving in 48 parts of an aqueous solution.
The coupler solution was adjusted so that the solution temperature was 10 ° C. or lower, added to the diazonium salt solution with stirring to cause a coupling reaction, and then heated at 90 ° C. for 30 minutes to obtain an azo red pigment C . I. Pigment Red 269 was produced.
The reaction solution was allowed to stand at room temperature, then filtered by a conventional method, washed with water, dried, and then pulverized by a sample mill to obtain a triazine compound represented by formula (10) and an azo red pigment C.I. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例３）
製造例１で得られた式（１０）で示されるトリアジン化合物３部を添加したことを除き、実施例２と同様にして、式（１０）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 3)
The triazine compound represented by the formula (10) and the azo red pigment C.I. were added in the same manner as in Example 2 except that 3 parts of the triazine compound represented by the formula (10) obtained in Production Example 1 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例４）
製造例２で得られた式（１１）で示されるトリアジン化合物３部を添加したことを除き、実施例３と同様にして、式（１１）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 Example 4
The triazine compound represented by the formula (11) and the azo red pigment C.I. were added in the same manner as in Example 3 except that 3 parts of the triazine compound represented by the formula (11) obtained in Production Example 2 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例５）
製造例３で得られた式（１２）で示されるトリアジン化合物３部を添加したことを除き、実施例３と同様にして、式（１２）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 5)
A triazine compound represented by the formula (12) and an azo red pigment C.I. were added in the same manner as in Example 3 except that 3 parts of the triazine compound represented by the formula (12) obtained in Production Example 3 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例６）
製造例４で得られた式（１３）で示されるトリアジン化合物３部を添加したことを除き、実施例３と同様にして、式（１３）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 6)
A triazine compound represented by the formula (13) and an azo red pigment C.I. were added in the same manner as in Example 3 except that 3 parts of the triazine compound represented by the formula (13) obtained in Production Example 4 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例７）
製造例４で得られた式（１３）で示されるトリアジン化合物０．８部を添加したことを除き、実施例６と同様にして、式（１３）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 7)
The triazine compound represented by the formula (13) and the azo red pigment C were obtained in the same manner as in Example 6 except that 0.8 part of the triazine compound represented by the formula (13) obtained in Production Example 4 was added. . I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例８）
製造例４で得られた式（１３）で示されるトリアジン化合物１．５部を添加したことを除き、実施例６と同様にして、式（１３）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 8)
The triazine compound represented by the formula (13) and the azo red pigment C were obtained in the same manner as in Example 6 except that 1.5 parts of the triazine compound represented by the formula (13) obtained in Production Example 4 was added. . I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例９）
製造例４で得られた式（１３）で示されるトリアジン化合物５部を添加したことを除き、実施例６と同様にして、式（１３）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 Example 9
A triazine compound represented by the formula (13) and an azo red pigment C.I. were added in the same manner as in Example 6 except that 5 parts of the triazine compound represented by the formula (13) obtained in Production Example 4 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例１０）
製造例４で得られた式（１３）で示されるトリアジン化合物１０部を添加したことを除き、実施例６と同様にして、式（１３）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 10)
A triazine compound represented by the formula (13) and an azo red pigment C.I. were added in the same manner as in Example 6 except that 10 parts of the triazine compound represented by the formula (13) obtained in Production Example 4 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例１１）
製造例４で得られた式（１３）で示されるトリアジン化合物２０部を添加したことを除き、実施例６と同様にして、式（１３）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 11)
A triazine compound represented by the formula (13) and an azo red pigment C.I. were added in the same manner as in Example 6 except that 20 parts of the triazine compound represented by the formula (13) obtained in Production Example 4 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例１２）
製造例５で得られた式（１４）で示されるトリアジン化合物３部を添加したことを除き、実施例３と同様にして、式（１４）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 12)
A triazine compound represented by the formula (14) and an azo red pigment C.I. were added in the same manner as in Example 3 except that 3 parts of the triazine compound represented by the formula (14) obtained in Production Example 5 was added. I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（実施例１３）
製造例５で得られた式（１４）で示されるトリアジン化合物１．５部を添加したことを除き、実施例１２と同様にして、式（１４）で示されるトリアジン化合物とアゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む微細顔料組成物１２１部を得た。 (Example 13)
The triazine compound represented by the formula (14) and the azo red pigment C were obtained in the same manner as in Example 12 except that 1.5 parts of the triazine compound represented by the formula (14) obtained in Production Example 5 was added. . I. 121 parts of a fine pigment composition containing CI Pigment Red 269 were obtained.

（比較例１）
式（１０）で示されるトリアジン化合物を添加しなかったことを除き、実施例１と同様にして、アゾ系黄色顔料Ｃ．Ｉ．ピグメントイエロー７４を含む顔料組成物１１５部を得た。 (Comparative Example 1)
In the same manner as in Example 1, except that the triazine compound represented by the formula (10) was not added, the azo yellow pigment C.I. I. 115 parts of a pigment composition containing CI Pigment Yellow 74 were obtained.

（比較例２）
式（１０）で示されるトリアジン化合物を添加しなかったことを除き、実施例２と同様にして、アゾ系赤色顔料Ｃ．Ｉ．ピグメントレッド２６９を含む顔料組成物１２０部を得た。 (Comparative Example 2)
In the same manner as in Example 2, except that the triazine compound represented by the formula (10) was not added, the azo red pigment C.I. I. 120 parts of a pigment composition containing Pigment Red 269 were obtained.

（顔料粒子径の測定）
実施例１〜１３、比較例１、２において調製した顔料組成物について、電子顕微鏡に連結したＣＣＤカメラで撮影した画像を用いて、顔料組成物に含まれる有機顔料の１次粒子の粒子径を測定した。電子顕微鏡は、日本電子データム株式会社製、ＪＥＭ−１０１１型を使用し、加圧電圧８０ｋＶ、測定倍率５万倍とし、ＣＣＤカメラは、オリンパス社製、ＭｅｇａＶｅｉｗ IIIを使用した。その結果を表１に示す。 (Measurement of pigment particle diameter)
For the pigment compositions prepared in Examples 1 to 13 and Comparative Examples 1 and 2, using the images taken with a CCD camera connected to an electron microscope, the particle size of the primary particles of the organic pigment contained in the pigment composition was determined. It was measured. The electron microscope used was JEM-1011 manufactured by JEOL Datum Co., Ltd., the applied voltage was 80 kV, the measurement magnification was 50,000 times, and the CCD camera used was MegaView III manufactured by Olympus. The results are shown in Table 1.

（インキの調製）
前記実施例１〜１３、比較例１、２の顔料組成物７．５部、分散剤（ジョンクリル６１Ｊ、ＢＡＳＦ社製）４部、イソプロピルアルコール５部、脱イオン水１３．５部、ガラスビーズ（直径２．５〜３．５ｍｍ）を１４０ｍＬガラス容器に入れ、ペイントコンディショナーにて６０分間分散させた。次いで、分散剤（ジョンクリル７００１、ＢＡＳＦ社製）２０部をさらに添加し、同様にして５分間分散させた後ガラスビーズを除去し、顔料分散体としてインキを調製した。このインキを、バーコーターを用いてウェット膜厚が０．１５μｍとなるようにポリプロピレンフィルムに展色し、乾燥した。 (Preparation of ink)
7.5 parts of the pigment compositions of Examples 1 to 13 and Comparative Examples 1 and 2, 4 parts of a dispersant (Johncrill 61J, manufactured by BASF), 5 parts of isopropyl alcohol, 13.5 parts of deionized water, glass beads (Diameter 2.5-3.5 mm) was put in a 140 mL glass container and dispersed for 60 minutes with a paint conditioner. Next, 20 parts of a dispersant (Johncrill 7001, manufactured by BASF) was further added and dispersed in the same manner for 5 minutes, and then the glass beads were removed to prepare an ink as a pigment dispersion. This ink was spread on a polypropylene film using a bar coater so that the wet film thickness was 0.15 μm and dried.

（評価）
上記のようにしてポリプロピレンフィルム上に調製した薄膜について、目視により透明性を確認した。尚、評価基準は、「◎」が非常に優れている、「○」が優れている、「×」が劣っている（不透明）である。その評価結果を表１に示す。 (Evaluation)
The transparency of the thin film prepared on the polypropylene film as described above was confirmed visually. The evaluation criteria are “◎” is very good, “◯” is excellent, and “x” is inferior (opaque). The evaluation results are shown in Table 1.

Figure 0005299151
Figure 0005299151

表１に示すように、実施例１〜１３の微細顔料組成物に含まれる有機顔料は、その一次粒子が極めて小さく、当該微細顔料組成物を用いた顔料分散体（インク）は、その透明性が優れており、顔料分散体において、一次粒子の凝集が著しく抑制されていることが示された。   As shown in Table 1, the organic pigment contained in the fine pigment compositions of Examples 1 to 13 has very small primary particles, and the pigment dispersion (ink) using the fine pigment composition has transparency. It was shown that the aggregation of primary particles was remarkably suppressed in the pigment dispersion.

（実施例１４）
縮合多環系顔料の赤色粗製顔料（Ｃ．Ｉ．ピグメントレッド２５４、商品名：Ｃｒｏｍｏｐｈｔａｌ Ｒｅｄ ２０３０，チバ・スパシャリティ・ケミカルズ製）３００部、製造例１で得られた式（１０）で示されるトリアジン化合物３０部、中性無水芒硝（平均粒径約２０μｍ、三田尻化学工業（株）製）３０００部、溶剤としてジエチレングリコール（（株）日本触媒製）７５０部を５Ｌニーダー（（株）モリヤマ製、Ｓ５−２ＧＨ−Ｓ型）に添加し、混練物の温度が５０℃になるように温度コントロールしながら９時間混練摩砕した。当該混練摩砕物を４０℃の温水３０Ｌに撹拌分散し、その後ヌッチェに移して濾過し、芒硝が完全に取り除かれるまで水洗を繰り返し、顔料水ペーストを得た。当該顔料水ペーストを、１０５℃で２時間乾燥させた。当該乾燥物を粉砕機（共立理工（株）製、小型粉砕機、サンプルミルＳＫ−Ｍ２）で粉砕し、式（１０）で示されるトリアジン化合物と縮合多環系赤色顔料Ｃ．Ｉ．ピグメントレッド２５４を含む微細顔料組成物３３０部を得た。 (Example 14)
300 parts of condensed red polycyclic pigment (CI Pigment Red 254, trade name: Chromophthal Red 2030, manufactured by Ciba Spatial Chemicals), a triazine represented by formula (10) obtained in Production Example 1 30 parts of compound, neutral anhydrous sodium sulfate (average particle size of about 20 μm, manufactured by Mitajiri Chemical Co., Ltd.), 750 parts of diethylene glycol (manufactured by Nippon Shokubai Co., Ltd.) as a solvent, 5 L kneader (manufactured by Moriyama Co., Ltd.) S5-2GH-S type) and kneaded and ground for 9 hours while controlling the temperature of the kneaded product to 50 ° C. The kneaded and ground product was stirred and dispersed in 30 L of warm water at 40 ° C., then transferred to Nutsche, filtered, and washed with water until the salt cake was completely removed to obtain a pigment water paste. The pigment water paste was dried at 105 ° C. for 2 hours. The dried product was pulverized with a pulverizer (manufactured by Kyoritsu Riko Co., Ltd., small pulverizer, sample mill SK-M2), and the triazine compound represented by the formula (10) and the condensed polycyclic red pigment C.I. I. 330 parts of a fine pigment composition containing CI Pigment Red 254 were obtained.

（実施例１５）
製造例６において得られた式（１５）で示されるトリアジン化合物を用いた以外は、実施例１４と同様にして、式（１５）で示されるトリアジン化合物と縮合多環系赤色顔料Ｃ．Ｉ．ピグメントレッド２５４を含む微細顔料組成物３３０部を得た。 (Example 15)
A triazine compound represented by the formula (15) and a condensed polycyclic red pigment C.I. were obtained in the same manner as in Example 14 except that the triazine compound represented by the formula (15) obtained in Production Example 6 was used. I. 330 parts of a fine pigment composition containing CI Pigment Red 254 were obtained.

（実施例１６）
製造例２において得られた式（１１）で示されるトリアジン化合物を用いた以外は、実施例１４と同様にして、式（１１）で示されるトリアジン化合物と縮合多環系赤色顔料Ｃ．Ｉ．ピグメントレッド２５４を含む微細顔料組成物３３０部を得た。 (Example 16)
A triazine compound represented by the formula (11) and a condensed polycyclic red pigment C.I. were obtained in the same manner as in Example 14 except that the triazine compound represented by the formula (11) obtained in Production Example 2 was used. I. 330 parts of a fine pigment composition containing CI Pigment Red 254 were obtained.

（比較例３）
トリアジン化合物を添加しなかった以外は、実施例１４と同様にして、縮合多環系赤色顔料Ｃ．Ｉ．ピグメントレッド２５４を含む微細顔料組成物３３０部を得た。 (Comparative Example 3)
A condensed polycyclic red pigment C.I. was prepared in the same manner as in Example 14 except that no triazine compound was added. I. 330 parts of a fine pigment composition containing CI Pigment Red 254 were obtained.

（実施例１７）
縮合多環系顔料の紫色粗製顔料（Ｃ．Ｉ．ピグメントバイオレット２３、商品名：Ｈｏｓｔａｐｅｒｍ Ｖｉｏｌｅｔ ＲＬ−０２、クラリアント製）５００部、製造例１で得られた式（１０）で示されるトリアジン化合物５０部、中性無水芒硝（平均粒径約２０μｍ、三田尻化学工業（株）製）２５００部、溶剤としてジエチレングリコール（（株）日本触媒製）８００部を５Ｌニーダー（（株）モリヤマ製、Ｓ５−２ＧＨ−Ｓ型）に添加し、混練物の温度が５０℃になるように温度コントロールしながら８時間混練摩砕した。当該混練摩砕物を４０℃の温水３０Ｌに撹拌分散し、その後ヌッチェに移して濾過し、芒硝が完全に取り除かれるまで水洗を繰り返し、顔料水ペーストを得た。当該顔料水ペーストを、１０５℃で２時間乾燥させた。当該乾燥物を粉砕機（共立理工（株）製、小型粉砕機、サンプルミルＳＫ−Ｍ２）で粉砕し、式（１０）で示されるトリアジン化合物と縮合多環系赤色顔料Ｃ．Ｉ．ピグメントバイオレット２３を含む微細顔料組成物５５０部を得た。 (Example 17)
Violet crude pigment of condensed polycyclic pigment (CI Pigment Violet 23, trade name: Hostaperm Violet RL-02, manufactured by Clariant) 500 parts, triazine compound 50 represented by formula (10) obtained in Production Example 1 Parts, neutral anhydrous sodium sulfate (average particle diameter of about 20 μm, manufactured by Mitajiri Chemical Co., Ltd.), 2500 parts of diethylene glycol (manufactured by Nippon Shokubai Co., Ltd.) as a solvent, 5 L kneader (manufactured by Moriyama Co., Ltd., S5- 2GH-S type) and kneaded and ground for 8 hours while controlling the temperature of the kneaded product to 50 ° C. The kneaded and ground product was stirred and dispersed in 30 L of warm water at 40 ° C., then transferred to Nutsche, filtered, and washed with water until the salt cake was completely removed to obtain a pigment water paste. The pigment water paste was dried at 105 ° C. for 2 hours. The dried product was pulverized with a pulverizer (manufactured by Kyoritsu Riko Co., Ltd., small pulverizer, sample mill SK-M2), and the triazine compound represented by the formula (10) and the condensed polycyclic red pigment C.I. I. 550 parts of a fine pigment composition containing Pigment Violet 23 were obtained.

（実施例１８）
製造例３において得られた式（１２）で示されるトリアジン化合物を用いた以外は、実施例１７と同様にして、式（１２）で示されるトリアジン化合物と縮合多環系赤色顔料Ｃ．Ｉ．ピグメントバイオレット２３を含む微細顔料組成物５５０部を得た。 (Example 18)
A triazine compound represented by the formula (12) and a condensed polycyclic red pigment C.I. were obtained in the same manner as in Example 17 except that the triazine compound represented by the formula (12) obtained in Production Example 3 was used. I. 550 parts of a fine pigment composition containing Pigment Violet 23 were obtained.

（実施例１９）
製造例７において得られた式（１６）で示されるトリアジン化合物を用いた以外は、実施例１７と同様にして、式（１６）で示されるトリアジン化合物と縮合多環系赤色顔料Ｃ．Ｉ．ピグメントバイオレット２３を含む微細顔料組成物５５０部を得た。 (Example 19)
The triazine compound represented by the formula (16) and the condensed polycyclic red pigment C.I. were obtained in the same manner as in Example 17 except that the triazine compound represented by the formula (16) obtained in Production Example 7 was used. I. 550 parts of a fine pigment composition containing Pigment Violet 23 were obtained.

（比較例４）
トリアジン化合物を添加しなかった以外は、実施例１７と同様にして、縮合多環系赤色顔料Ｃ．Ｉ．ピグメントバイオレット２３を含む微細顔料組成物５５０部を得た。 (Comparative Example 4)
A condensed polycyclic red pigment C.I. was prepared in the same manner as in Example 17 except that no triazine compound was added. I. 550 parts of a fine pigment composition containing Pigment Violet 23 were obtained.

（カラーフィルターの調製）
実施例１４〜１９、比較例３、４の微細顔料組成物を用いて、表２で示す組成の混合物を調製した。表中ＰＲ２５４はＣ．Ｉ．ピグメントレッド２５４の略称で、その列は、実施例１４〜１６、比較例３についての組成であり、ＰＶ２３はＣ．Ｉ．ピグメントバイオレット２３の略称であり、その列は、実施例１７〜１９、比較例４についての組成である。また、アクリル樹脂として、昭和高分子製のＳＰＣＮ−２０００、分散剤として、ＰＲ２５４にはビックケミージャパン製のＢＹＫ−ＬＰＮ６９１９、ＰＶ２３にはビックケミージャパン製のＤｉｓｐｅｒｂｙｋ−２００１、溶剤として、プロピレングリコールモノメチルエーテルアセテート（ＰＭＡ）を使用した。ジルコニアビーズは直径が０．５ｍｍのものを使用した。尚、表中のアクリル樹脂の値は、４０％ＰＭＡ溶液として添加した時の値である。また、ＰＶ２３を含む微細顔料組成物の評価にあたっては、カラーフィルターとしての評価を適切に行うため、Ｃ．Ｉ．ピグメントブルー１５：６（商品名：フタロシアニンブルー６００５、山陽色素製）（以下、ＰＢ１５：６という）との混合物を用いた。顔料の値は混合物としての値であり、その混合比（重量基準）は、（ＰＢ１５：６）／（ＰＶ２３）＝４／１とした。 (Preparation of color filter)
Using the fine pigment compositions of Examples 14 to 19 and Comparative Examples 3 and 4, mixtures having the compositions shown in Table 2 were prepared. In the table, PR254 is C.I. I. This is an abbreviation for CI Pigment Red 254, and its columns are the compositions of Examples 14 to 16 and Comparative Example 3. I. This is an abbreviation for Pigment Violet 23, and the columns are the compositions for Examples 17 to 19 and Comparative Example 4. As acrylic resin, SPCN-2000 made by Showa Polymer, as dispersant, BYK-LPN6919 made by Big Chemie Japan, Disperbyk-2001 made by Big Chemie Japan, and PV23 as propylene glycol monomethyl ether as solvent Acetate (PMA) was used. Zirconia beads having a diameter of 0.5 mm were used. In addition, the value of the acrylic resin in a table | surface is a value when it adds as a 40% PMA solution. In the evaluation of the fine pigment composition containing PV23, in order to appropriately evaluate as a color filter, C.I. I. A mixture with Pigment Blue 15: 6 (trade name: Phthalocyanine Blue 6005, manufactured by Sanyo Dye) (hereinafter referred to as PB15: 6) was used. The value of the pigment is a value as a mixture, and the mixing ratio (weight basis) was (PB15: 6) / (PV23) = 4/1.

Figure 0005299151
Figure 0005299151

上記組成で調製した混合物を１４０ｍＬガラス容器に入れ、ペイントコンディショナーにて６０分間分散させた後、ジルコニアビーズを除去し、顔料分散体を調製した。この顔料分散体を、スピンコート（ＭＩＫＡＳＡ ＳＰＩＮＣＯＲＴＥＲ ＩＨ−ＤＸ２）を用いて薄膜状の塗板（カラーフィルター）を調製した。   The mixture prepared with the above composition was put in a 140 mL glass container and dispersed with a paint conditioner for 60 minutes, and then zirconia beads were removed to prepare a pigment dispersion. A thin coating plate (color filter) was prepared from this pigment dispersion using spin coating (MIKASA SPINCENTER IH-DX2).

（評価）
上記のようにして調製したカラーフィルターを用い、分光光度計（ＳＰＥＣＴＲＯＰＨＯＴＯＭＥＴＥＲ ＣＭ−３７００ｄ）にてＹ値、コントラスト（ＣＲ）を測定した。
尚、コントラストの測定方法は、以下のとおりである。即ち、カラーフィルターを２枚の偏光板の間にはさみ、各偏光板の偏光面を平行にした時の透過光照度と垂直にした時の透過光照度とを測定し、その比を求めた。透過光照度の測定には、輝度計「ＬＳ−１００」（ミノルタ社製）を用いた。各測定結果を表３に示す。 (Evaluation)
Using the color filter prepared as described above, the Y value and contrast (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 3 shows the measurement results.

Figure 0005299151
Figure 0005299151

表３に示すように、実施例１４〜１９において得られた微細顔料組成物を用いたカラーフィルターは、Ｙ値を低下させることなく、高コントラストであることから、顔料の一次粒子が極めて小さく、かつその凝集が効果的に抑制されていることが示唆される。   As shown in Table 3, since the color filter using the fine pigment composition obtained in Examples 14 to 19 has high contrast without lowering the Y value, the primary particles of the pigment are extremely small, And it is suggested that the aggregation is effectively suppressed.

Claims (9)

式（１）で示されるトリアジン化合物と有機顔料とを含む微細顔料組成物。
Figure 0005299151
 （式（１）中、Ａは、式（７）で示される基から選択されるいずれかの酸性基又は−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（ＣＨ 3 ） 2 、−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（Ｃ 2 Ｈ 5 ） 2 、−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（Ｃ 3 Ｈ 7 ） 2 および−ＮＨ−（ＣＨ 2 ） 3 −Ｎ（Ｃ 4 Ｈ 9 ） 2 から選択されるいずれかの塩基性基を示す。Ｂは、−ＯＨ又は−Ｃｌを示す。Ｄは、式（９）で示される一群の基のいずれかの芳香族アミン残基を示す。）
Figure 0005299151
 （式（７）中、Ｒ4、Ｒ5、Ｒ6は、それぞれ独立して、−Ｈ、−ＮＯ2、−Ｃｌ、炭素数１〜４の低級アルキル基、炭素数１〜４の低級アルコキシル基、−ＣＦ3、−ＳＯ3Ｈ、−ＳＯ2Ｎ（Ｃ2Ｈ5）2、−ＣＯＯＨ、−ＣＯＯＣＨ3、−ＣＯＮＨ2、−ＳＯ2−ＮＨ2−Ｐｈ（Ｐｈはフェニル基を示す）、−ＣＯＮＨ−Ｐｈ（Ｐｈは、−Ｈ、−Ｃｌ、メチレン基の置換基を有して良いフェニル基を示す）のいずれかを示す。）
Figure 0005299151
 A fine pigment composition comprising a triazine compound represented by the formula (1) and an organic pigment.
Figure 0005299151
 (In the formula (1), A represents any acidic group selected from the group represented by the formula (7), or —NH— (CH 2 ) 3 —N (CH 3 ) 2 , —NH— (CH 2 ) 3 -N (C 2 H 5 ) 2, -NH- (CH 2) 3 -N (C 3 H 7) 2 and -NH- (CH 2) is selected from 3 -N (C 4 H 9) 2 .B showing the Ruizure of basic groups, .D showing an -OH or -Cl represents any aromatic amine residue of a group of groups represented by the formula (9).)
Figure 0005299151
 (In the formula (7), R 4 , R 5 and R 6 are each independently —H, —NO 2 , —Cl, a lower alkyl group having 1 to 4 carbon atoms, or a lower alkoxyl having 1 to 4 carbon atoms. group, -CF 3, -SO 3 H, -SO 2 N (C 2 H 5) 2, -COOH, -COOCH 3, -CONH 2, -SO 2 -NH 2 -Ph (Ph represents a phenyl group) , -CONH-Ph (Ph represents -H, -Cl, a phenyl group which may have a substituent of a methylene group).
Figure 0005299151
 前記有機顔料が、アゾ系顔料である請求項１に記載の微細顔料組成物。 The fine pigment composition according to claim 1 , wherein the organic pigment is an azo pigment. 前記アゾ系顔料が、カラーインデックス ピグメントイエロー７４又はピグメントレッド２６９である請求項２記載の微粒化顔料組成物。 The atomized pigment composition according to claim 2 , wherein the azo pigment is Color Index Pigment Yellow 74 or Pigment Red 269. 前記有機顔料が、縮合多環系顔料である請求項１に記載の微細顔料組成物。 The fine pigment composition according to claim 1 , wherein the organic pigment is a condensed polycyclic pigment. 前記縮合多環系顔料が、カラーインデックス ピグメントバイオレット２３又はピグメントレッド２５４である請求項４記載の微粒化顔料組成物。 The atomized pigment composition according to claim 4 , wherein the condensed polycyclic pigment is Color Index Pigment Violet 23 or Pigment Red 254. 請求項１に記載の式（１）で示されるトリアジン化合物存在下で、ジアゾニウム塩をカップラーとカップリング反応させることを特徴とするアゾ系顔料を含む微細顔料組成物の製造方法。 A method for producing a fine pigment composition containing an azo pigment, wherein a diazonium salt is subjected to a coupling reaction with a coupler in the presence of a triazine compound represented by the formula (1) according to claim 1 . カップラー１００部に対し、前記トリアジン化合物が０．１〜２０部となるように添加する請求項６記載のアゾ系顔料を含む微細顔料組成物の製造方法。 The manufacturing method of the fine pigment composition containing the azo pigment of Claim 6 added so that the said triazine compound may be 0.1-20 parts with respect to 100 parts of couplers. 請求項１に記載の式（１）で示されるトリアジン化合物存在下で、粗製顔料を顔料化することを特徴とする縮合多環系顔料を含む微細顔料組成物の製造方法。 A method for producing a fine pigment composition containing a condensed polycyclic pigment, wherein the crude pigment is pigmented in the presence of the triazine compound represented by the formula (1) according to claim 1 . 粗製顔料１００部に対し、前記トリアジン化合物が０．１〜２０部となるように添加する請求項８記載の縮合多環系顔料を含む微細顔料組成物の製造方法。 The method for producing a fine pigment composition containing a condensed polycyclic pigment according to claim 8 , wherein the triazine compound is added in an amount of 0.1 to 20 parts per 100 parts of the crude pigment.
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