JP2007277449A - Method for producing fine organic pigment - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for producing a pigment, solving such problems as much energy consumption as a problem in conventional kneaders, pigment grade such as gloss and coloring power, micronizing level limit and interlot contamination. <P>SOLUTION: The method for producing the fine organic pigment comprises kneading a mixture of an organic pigment, a water-soluble inorganic salt and a water-miscible organic solvent with a planetary-type mixer 1 with multiple blades 4 subject to planetary motion. Owing to the use of such a planetary mixer, the objective finer organic pigment can be obtained with a small amount of energy. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

The present invention relates to a method for producing an organic pigment in which particles of color developing powder are finely sized to have a uniform particle size and extremely dispersible in a vehicle. More specifically, the present invention provides good gloss, high coloring power, transparency, and the like when particles of color developing powder are dispersed in a vehicle such as an aqueous flexo ink, a coloring material, and an aqueous dispersion. Relates to a method for producing a fine organic pigment that provides excellent suitability even in applications requiring finer organic pigment particles such as inkjet inks and color filters.

Organic pigments typified by phthalocyanine pigments have a fine color tone, large coloring power, various functions such as weather resistance, heat resistance, etc., and a large amount in the color material industry. In addition, it is widely used. A solvent salt milling method is currently widely used as a method for refining a pigment.
In the solvent salt milling method, coarse pigment particles are mechanically treated by a kneader or the like in the presence of inorganic salts such as sodium chloride and sodium sulfate and highly viscous water-soluble organic solvents such as ethylene glycol, diethylene glycol and polyethylene glycol. It is a method to grind and refine. The solvent salt milling method is an effective method for refining and sizing pigment particles, but in order to achieve higher performance in inkjet and color filters, it was obtained by the conventional salt milling method. There is a need to use finer and sized pigments than pigments.
In addition, the conventional batch type kneader and the like have problems such as restrictions on the production scale derived from the batch type, variations in quality for each lot, contamination of the working environment due to foreign matter contamination and dust generation due to the open type.
Japanese Patent Laid-Open No. 7-53889

Although the solvent salt milling method is industrially advantageous, the kneader that has been widely used conventionally has a limit in the use of a great deal of energy for the refinement of organic pigments and in the refinement level. Furthermore, even when the fine organic pigment obtained is dispersed in a vehicle such as an aqueous flexo ink, a colorant, an aqueous dispersion, etc., the gloss, coloring power, transparency, etc. of the developed product are improved. It was always a challenge. Furthermore, finer pigment particles are required for applications such as inkjet inks and color filters, but it is difficult to obtain these by the above-described method, and a great deal of energy and time are required. In addition, the kneader has the problem that the kneaded material enters the rotating shaft and the cleaning properties of the gaps and the like are low, so that the kneaded material of the previous lot is mixed during the next lot operation, and the generation of contaminants is likely to occur. It was unsuitable for the production of a wide variety of products.
The present invention has been made in view of such a situation, and includes the consumption of enormous energy, gloss, coloring power, and the like, as well as limitations on the fineness level, contamination contamination between lots, and the like, which are cited as problems in conventional kneaders. It aims at providing the manufacturing method of the pigment which solves.

The method for producing a fine organic pigment of the present invention comprises a planetary mixer in which a plurality of blades move in a planetary motion, an organic pigment (excluding a mixture of α-type phthalocyanine and ε-type phthalocyanine), a water-soluble inorganic salt, and a water-soluble organic liquid. The mixture is kneaded to obtain a fine organic pigment with less energy compared to a kneader which is a general kneader. Furthermore, the number of blades is three. Furthermore, the mixture of the organic pigment, the water-soluble inorganic salt and the water-soluble organic liquid is 1 part by weight or more and 30 parts by weight or less of the water-soluble inorganic salt and 0.1 part by weight of the water-soluble organic liquid with respect to 1 part by weight of the organic pigment. It is a mixture containing at least 7 parts by weight and no more than 7 parts by weight. Furthermore, a resin is contained in a mixture of an organic pigment, a water-soluble inorganic salt, and a water-soluble organic liquid. Furthermore, a pigment derivative is contained in a mixture of an organic pigment, a water-soluble inorganic salt, and a water-soluble organic liquid.

According to the first aspect of the present invention, an organic pigment (excluding a mixture of α-type phthalocyanine and ε-type phthalocyanine), a water-soluble inorganic salt, a water-soluble organic liquid, and a planetary mixer in which a plurality of blades move in a planetary motion. A fine organic pigment can be obtained by kneading the mixture.
According to the second aspect of the invention, when the number of blades is 3, milling and kneading better than two can be performed, and a fine organic pigment can be obtained.
According to the invention described in claim 3, the refinement of the organic pigment is promoted by adding a large amount of the water-soluble inorganic salt coexisting with the organic pigment to the organic pigment. Furthermore, refinement | miniaturization can be accelerated | stimulated by adjusting suitably the quantity of a water-soluble organic solvent within the compounding ratio range of Claim 2.
According to invention of Claim 4, aqueous flexo ink, a coloring material, an aqueous dispersion, and inkjet use which are a use use by making resin contain in the mixture of an organic pigment, water-soluble inorganic salt, and water-soluble organic liquid. Demonstrates the effect of improving the suitability of various applications such as ink and color filters.
According to the fifth aspect of the present invention, the pigment growth is further suppressed by efficiently adding a pigment derivative to the mixture of the organic pigment, the water-soluble inorganic salt, and the water-soluble organic liquid, thereby miniaturizing efficiently. Furthermore, the obtained pigment has an effect of improving suitability for various uses.

A planetary mixer used in the present invention will be described with reference to the drawings. The planetary mixer main body (1) has a plurality of drive shafts (2) (two examples in the drawing) that perform planetary movement via a suitable transmission mechanism by a drive source (not shown) such as a motor. The drive shaft (2) is attached with a blade (4) so as to be inserted into the tank (3). When the processing material is put into the tank, the blade is lowered and set in a state as shown in FIG. 1, and a plurality of blades are planetarily moved in the tank, the blade and the inner wall of the tank, between the bottom wall and the plurality of blades A shearing force is applied to the treated material between the blades.
Specific examples of the planetary mixer of the present invention include, for example, a planetary mixer, a spiral mixer, and a trimix (manufactured by Inoue Seisakusho), and the trimix can provide a large shearing force. Is desirable to achieve.

Hereinafter, the kneaded composition subjected to the milling and kneading process by such a mixer will be described in detail.
The organic pigments used in the kneaded composition are indicated by color index numbers below.
Examples of the red coloring composition include CI Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 97, 122. 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240 Red pigments such as 246, 254, 255, 264, and 272 can be used. A yellow pigment and an orange pigment can be used in combination with the red coloring composition.
Examples of the yellow coloring composition for forming the yellow filter segment include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20. 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167 It can be used yellow pigments such 168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199.
For example, an orange pigment such as CI Pigment orange 36, 43, 51, 55, 59, 61 can be used as the orange coloring composition for forming the orange filter segment.
For the green coloring composition for forming the green filter segment, for example, a green pigment such as CIPigment Green 7, 10, 36, 37 can be used. A yellow pigment can be used in combination with the green coloring composition.
The blue coloring composition for forming the blue filter segment includes a purple pigment such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, etc. Can be used in combination.
For the magenta coloring composition for forming the magenta color filter segment, for example, purple pigments and red pigments such as CI Pigment Violet 1, 19, CI Pigment Red 144, 146, 177, 169, 81 can be used. A yellow pigment can be used in combination with the magenta composition.
The water-soluble inorganic salt used in the present invention is not particularly limited, and examples thereof include sodium chloride (sodium chloride), potassium chloride, sodium sulfate, zinc chloride, calcium chloride, and mixtures thereof.
The amount of the water-soluble inorganic salt in the kneaded composition is preferably 1 part by weight or more and 30 parts by weight or less with respect to 1 part by weight of the organic pigment. When the amount of the water-soluble inorganic salt is less than 1 part by weight, it is difficult to refine the organic pigment, and when it exceeds 30 parts by weight, it is possible to obtain a refined organic pigment. This is because, since the amount is small, productivity is lowered and industrially disadvantageous.
In addition, the water-soluble organic liquid used in the present invention is added so that the organic pigment and the water-soluble inorganic salt are uniformly solidified, and can be mixed freely with water or not mixed freely, but industrially. It has a solubility that can be removed by washing with water. The water-soluble organic liquid is not particularly limited as long as the pigment particles grow, but a high-boiling solvent is preferable from the viewpoint of safety because the temperature rises during kneading and the organic liquid easily evaporates.
The amount of the water-soluble organic liquid in the kneaded composition is preferably 0.1 to 7 parts by weight with respect to 1 part by weight of the organic pigment, and the amount of the water-soluble inorganic salt and the hardness of the kneaded composition. It can be selected according to. When the amount of the water-soluble inorganic salt is less than 0.1 parts by weight, the kneaded composition becomes too hard to be operated safely, and when it exceeds 7 parts by weight, the kneaded composition becomes too soft and the fineness of the organic pigment The level of conversion decreases.
Examples of water-soluble organic solvents include 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono Butyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low Molecular weight polypropylene glycol, aniline, pyridine, tetrahydrofuran, dioxane, methanol, eta , Isopropanol, n-propanol, isobutanol, n-butanol, ethylene glycol, propylene glycol, propylene glycolic monomethyl ether acetate, ethyl acetate, isopropyl acetate, acetone, methyl ethyl ketone, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, etc. Can be mentioned. Moreover, you may mix and use 2 or more types of solvents as needed.
When kneading a mixture of an organic pigment, a water-soluble inorganic salt, and a water-soluble organic liquid, a resin may be added for the purpose of easily dispersing the resulting fine organic pigment in a pigment carrier.
The resin is preferably poorly water-soluble and partially soluble in a water-soluble organic liquid, such as rosin, disproportionated rosin, polymerized rosin, hydrogenated rosin, rosin ester, rosinamine, maleated rosin, fumarated rosin, Synthetic resins such as rosin metal salts, rosin resins such as rosin-modified phenolic resins and rosin-modified maleic resins, epoxy resins, acrylic resins, maleic resins, butyral resins, polyester resins, melamine resins, phenolic resins, polyurethane resins and polyamide resins In addition, modified resins derived from fiber, rubber, and the like can be mentioned, and rosin resins are particularly preferable from the viewpoint of the addition effect and cost.
The amount of the resin in the kneaded composition is not particularly limited, but is preferably 0.001 part by weight or more and 1.0 part by weight or less with respect to 1 part by weight of the organic pigment. When the amount of the resin is less than 0.001 part by weight, it is difficult to obtain the dispersion effect, and when it exceeds 1.0 part by weight, the dispersion effect for the added amount cannot be obtained. Further, it is preferable to adjust the amount of the resin depending on the difference in properties between the resin and the pigment carrier. In other words, if the difference is large, the amount of resin should be kept to the minimum necessary to reduce the effect on the physical properties of the pigment carrier, while if the difference is small, the amount of resin should be increased to fully exhibit the dispersion effect. Is preferred.
In addition, when kneading a mixture of an organic pigment, a water-soluble inorganic salt, and a water-soluble organic liquid, the organic pigment, anthraquinone, acridone, or triazine may be basic for the purpose of preventing crystal growth or crystal dislocation of the organic pigment. Alternatively, an acidic substituent or various derivatives introduced with a phthalimidomethyl group may be added. Among these, it is preferable to add a pigment derivative having a basic or acidic substituent or a phthalimidomethyl group introduced into an organic pigment. Examples of the basic substituent include substituents represented by the following formulas (1) to (4). Examples of the acidic substituent include a sulfonic acid group and a carboxyl group.
The pigment derivative is preferably a pigment derivative having the same structure as that of the organic pigment to be finely pulverized, but may be a pigment derivative having a structure different from the matrix.
The amount of the pigment derivative in the kneaded composition is preferably 0.001 part by weight or more and 0.3 part by weight or less with respect to 1 part by weight of the organic pigment. When the amount of the pigment derivative is less than 0.001 part by weight, it is difficult to obtain the added effect. If the amount exceeds 0.3 parts by weight, not only the effect of the added amount can be obtained, but also the resulting fine organic pigment becomes a mixture with the pigment derivative, so the difference between the physical properties of the organic pigment alone is large. Become.

（上記式（１）〜（４）において、
Ｘは、−ＳＯ₂−、−ＣＯ−、−ＣＨ₂ＮＨＣＯＣＨ₂−、−ＣＨ₂−または直接結合を表し、
ｎは、１〜１０の整数を表し、Ｒ₁およびＲ₂は、それぞれ独立に、置換されていてもよい炭素数１〜３６のアルキル基、置換されていてもよい炭素数２〜３６のアルケニル基もしくは置換されていてもよいフェニル基を表すか、またはＲ₁とＲ₂とが結合して更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を形成し、
Ｒ₃は、置換されていてもよい炭素数１〜３６のアルキル基、置換されていてもよい炭素
数２〜３６のアルケニル基または置換されていてもよいフェニル基を表し、
Ｒ₄、Ｒ₅、Ｒ₆およびＲ₇は、それぞれ独立に、水素原子、置換されていてもよい炭素数１〜３６のアルキル基、置換されていてもよい炭素数２〜３６のアルケニル基または置換されていてもよいフェニル基を表し、
Ｙは、−ＮＲ₈−Ｚ−ＮＲ₉−または直接結合を表し、Ｒ₈およびＲ₉は、それぞれ独立に、水素原子、置換されていてもよい炭素数１〜３６のアルキル基、置換されていてもよい炭素数２〜３６のアルケニル基または置換されていてもよいフェニル基を表し、
Ｚは、置換されていてもよい炭素数１〜３６のアルキレン基、置換されていてもよい炭素数２〜３６のアルケニレン基、または置換されていてもよいフェニレン基を表し、
Ｒは、下記式（５）で示される置換基、または下記式（６）で示される置換基を表し、
Ｑは、水酸基、アルコキシル基、下記式（５）で示される置換基または下記式（６）で示される置換基を表す。式（５）および式（６）において、Ｒ₁〜Ｒ₇およびｎは、上に定義した通りのものである。）

(In the above formulas (1) to (4),
X represents —SO ₂ —, —CO—, —CH ₂ NHCOCH ₂ —, —CH ₂ — or a direct bond;
n represents an integer of 1 to 10, and R ₁ and R ₂ each independently represents an optionally substituted alkyl group having 1 to 36 carbon atoms or an optionally substituted alkenyl group having 2 to 36 carbon atoms. Represents a group or an optionally substituted phenyl group, or R ₁ and R ₂ combine to form an optionally substituted heterocycle containing additional nitrogen, oxygen or sulfur atoms;
R ₃ represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group;
R ₄ , R ₅ , R ₆ and R ₇ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or Represents an optionally substituted phenyl group,
Y represents —NR ₈ —Z—NR ₉ — or a direct bond, and R ₈ and R ₉ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, or a substituted group. Represents an optionally substituted alkenyl group having 2 to 36 carbon atoms or an optionally substituted phenyl group,
Z represents an optionally substituted alkylene group having 1 to 36 carbon atoms, an optionally substituted alkenylene group having 2 to 36 carbon atoms, or an optionally substituted phenylene group;
R represents a substituent represented by the following formula (5) or a substituent represented by the following formula (6),
Q represents a hydroxyl group, an alkoxyl group, a substituent represented by the following formula (5) or a substituent represented by the following formula (6). In formula (5) and formula (6), R _{1 to} R ₇ and n are as defined above. )

顔料誘導体を構成する有機顔料としては、例えば、ジケトピロロピロール系顔料、アゾ、ジスアゾ、ポリアゾ等のアゾ系顔料、フタロシアニン系顔料、ジアミノジアントラキノン、アントラピリミジン、フラバントロン、アントアントロン、インダントロン、ピラントロン、ビオラントロン等のアントラキノン系顔料、キナクリドン系顔料、ジオキサジン系顔料、ペリノン系玩弄、ペリレン系顔料、チオインジゴ系顔料、イソインドリン系顔料、イソインドリノン系顔料、キノフタロン系顔料、スレン系顔料、金属錯体系顔料が挙げられる。また、上記に示した混練組成物に用いられる顔料でもよい。
また、アントラキノン誘導体およびアクリドン誘導体を構成するアントラキノンおよびアクリドンは、メチル基、エチル基等のアルキル基、アミノ基、ニトロ基、水酸基、またはメトキシ基、エトキシ基等のアルコキシ基、または塩素等のハロゲン等の置換基を有していてもよいアントラキノンおよびアクリドンである。
また、トリアジン誘導体を構成するトリアジンは、メチル基、エチル基等のアルキル基、アミノ基またはジメチルアミノ基、ジエチルアミノ基、ジブチルアミノ基等のアルキルアミノ基、ニトロ基、水酸基、またはメトキシ基、エトキシ基、ブトキシ基等のアルコキシ基、塩素等のハロゲン、またはメチル基、メトキシ基、アミノ基、ジメチルアミノ基、水酸基等で置換されていてもよいフェニル基またはメチル基、エチル基、メトキシ基、エトキシ基、アミノ基、ジメチルアミノ基、ジエチルアミノ基、ニトロ基、水酸基等で置換されていてもよいフェニルアミノ基等の置換基を有していてもよい１，３，５−トリアジンである。
塩基性の置換基を有する顔料誘導体、アントラキノン誘導体およびアクリドン誘導体は、種々の合成経路で合成することができる。例えば、有機顔料、アントラキノンまたはアクリドンに、下記式（７）〜（１０）で表される置換基を導入した後、該置換基と反応して一般式（１）〜（４）で表される置換基を形成するアミン成分、例えば、Ｎ，Ｎ−ジメチルアミノプロピルアミン、Ｎ−メチルピペラジン、ジエチルアミンまたは４−［４−ヒドロキシ−６−［３−（ジブチルアミノ）プロピルアミノ］−１，３，５−トリアジン−２−イルアミノ］アニリン等を反応させることによって得られる。
式（７） −ＳＯ₂Ｃｌ
式（８） −ＣＯＣｌ
式（９） −ＣＨ₂ＮＨＣＯＣＨ₂Ｃｌ
式（１０） −ＣＨ₂Ｃｌ
一般式（７）〜（１０）と上記アミン成分の反応時には、一般式（７）〜（１０）の一部が加水分解して、塩素が水酸基に置換したものが混在していてもよい。その場合、一般式（７）、一般式（８）はそれぞれスルホン酸基、カルボン酸基となるが、何れも遊離酸のままでもよく、また、１〜３価の金属または上記のモノアミンとの塩であってもよい。
有機顔料がアゾ系顔料である場合は、一般式（１）〜（４）で表される置換基をあらかじめジアゾ成分またはカップリング成分に導入し、その後カップリング反応を行うことによって塩基性基を有するアゾ系顔料誘導体を製造することもできる。
また、特定の塩基性基を有するトリアジン誘導体も、種々の合成経路で合成することができる。例えば、塩化シアヌルを出発原料とし、塩化シアヌルの少なくとも１つの塩素に一般式（１）〜（４）で表される置換基を形成するアミン成分、例えば、Ｎ，Ｎ−ジメチルアミノプロピルアミンまたはＮ−メチルピペラジン等を反応させ、次いで塩化シアヌルの残りの塩素と種々のアミンまたはアルコール等を反応させることによって得られる。
塩基性の置換基を有する誘導体の具体例を以下に示すが、これらに限定されるわけではない。これらの誘導体は、単独でまたは２種類以上を混合して用いることができる。

Examples of organic pigments constituting the pigment derivative include diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, polyazo, phthalocyanine pigments, diaminodianthraquinone, anthrapyrimidine, flavantrons, anthanthrone, indanthrone, Anthraquinone pigments such as pyranthrone, violanthrone, quinacridone pigments, dioxazine pigments, perinone toys, perylene pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, selenium pigments, metal complexes Systemic pigments are mentioned. Moreover, the pigment used for the kneading | mixing composition shown above may be sufficient.
Anthraquinone derivatives and acridone derivatives constituting anthraquinone derivatives and acridone derivatives are alkyl groups such as methyl and ethyl groups, amino groups, nitro groups, hydroxyl groups, alkoxy groups such as methoxy groups, ethoxy groups, halogens such as chlorine, etc. Anthraquinone and acridone which may have the following substituents:
The triazine constituting the triazine derivative is an alkyl group such as a methyl group or an ethyl group, an amino group or a dimethylamino group, an alkylamino group such as a diethylamino group or a dibutylamino group, a nitro group, a hydroxyl group, a methoxy group or an ethoxy group. , An alkoxy group such as a butoxy group, a halogen such as chlorine, or a phenyl group or a methyl group optionally substituted with a methyl group, a methoxy group, an amino group, a dimethylamino group, a hydroxyl group, an ethyl group, a methoxy group, an ethoxy group 1,3,5-triazine which may have a substituent such as phenylamino group which may be substituted with amino group, dimethylamino group, diethylamino group, nitro group, hydroxyl group and the like.
Pigment derivatives, anthraquinone derivatives and acridone derivatives having a basic substituent can be synthesized by various synthetic routes. For example, after introducing a substituent represented by the following formulas (7) to (10) into an organic pigment, anthraquinone or acridone, it reacts with the substituent and is represented by the general formulas (1) to (4). Amine components that form substituents such as N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3 It can be obtained by reacting 5-triazin-2-ylamino] aniline or the like.
Formula (7) —SO ₂ Cl
Formula (8) -COCl
Formula (9) —CH ₂ NHCOCH ₂ Cl
Equation (10) -CH ₂ Cl
At the time of reaction of the general formulas (7) to (10) and the amine component, a part of the general formulas (7) to (10) may be hydrolyzed so that chlorine is substituted with a hydroxyl group. In that case, the general formula (7) and the general formula (8) are a sulfonic acid group and a carboxylic acid group, respectively, but both may be a free acid, and may be a 1 to 3 valent metal or the above monoamine. It may be a salt.
When the organic pigment is an azo pigment, a basic group is introduced by introducing a substituent represented by the general formulas (1) to (4) into a diazo component or a coupling component in advance and then performing a coupling reaction. An azo pigment derivative having the same can also be produced.
Triazine derivatives having a specific basic group can also be synthesized by various synthetic routes. For example, starting from cyanuric chloride, an amine component that forms a substituent represented by the general formulas (1) to (4) on at least one chlorine of cyanuric chloride, such as N, N-dimethylaminopropylamine or N It is obtained by reacting methylpiperazine or the like and then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.
Specific examples of the derivative having a basic substituent are shown below, but are not limited thereto. These derivatives can be used alone or in admixture of two or more.

本発明におけるミキサーの運転時における温度条件において、摩砕混練を効果的に進行させるため、混練温度は、０〜１５０℃、特には４０〜９０℃が好ましい。
混練組成物は初期に全量投入する必要はなく、混練組成物の硬さの状況もしくは混練開始後に混練組成物の微細化および整粒度に応じて、水溶性有機溶剤および水溶性無機塩を適宜投入しても良い。
混練後の混練組成物は常法により処理される。すなわち、混練組成物を水または鉱酸水溶液で処理し、濾過、水洗により水溶性無機塩および水溶性有機溶剤を除去し微細有機顔料を単離する。得られた微細有機顔料はこのまま湿潤状態で使用することも、乾燥・粉砕により粉末状態で使用することも可能である。必要に応じて樹脂、界面活性剤、その他の添加剤を混練後に加えてもよい。
本発明による方法で製造された微細有機顔料の用途は特に限定されないが、一般に用いられる色材用途に加えて、高い光沢や着色力、透明性等を要求される用途にも使うことができ、インクジェット用インキやカラーフィルター等の用途にも適用できる。

In the temperature condition at the time of operation of the mixer in the present invention, the kneading temperature is preferably 0 to 150 ° C., particularly preferably 40 to 90 ° C., in order to effectively proceed the milling and kneading.
It is not necessary to add the entire amount of the kneaded composition in the initial stage, and a water-soluble organic solvent and a water-soluble inorganic salt are appropriately added depending on the hardness of the kneaded composition or after the start of kneading, depending on the refinement and particle size of the kneaded composition. You may do it.
The kneaded composition after kneading is processed by a conventional method. That is, the kneaded composition is treated with water or an aqueous mineral acid solution, and the fine organic pigment is isolated by removing the water-soluble inorganic salt and the water-soluble organic solvent by filtration and washing with water. The obtained fine organic pigment can be used in a wet state as it is, or in a powder state by drying and pulverization. If necessary, a resin, a surfactant and other additives may be added after kneading.
The use of the fine organic pigment produced by the method according to the present invention is not particularly limited, but in addition to commonly used color materials, it can be used for applications that require high gloss, coloring power, transparency, It can also be applied to uses such as inkjet inks and color filters.

Hereinafter, the present invention will be described in detail with reference to examples and comparative examples according to conventional methods. However, the present invention is not limited to the scope of these examples. In the examples, “parts” represents parts by weight, and “%” represents% by weight.
In Examples and Comparative Examples, the particle diameter was measured by observing particles with a transmission microscope and measuring and analyzing the equivalent circle diameter of particles in the image.
Example 1
500 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254, “Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals), 5000 parts of sodium chloride, 1100 parts of diethylene glycol, 15,000 parts by volume of trimix ( The resulting mixture was ground and finely diketopyrrolopyrrole was produced. As operating conditions, the milling temperature was 70 ° C., the revolution was 20 rpm, and the rotation was 60 rpm, and the mixture was kneaded for 8 hours while maintaining a dense lump. The kneaded composition obtained here was taken out in 10000 parts of a 1% aqueous sulfuric acid solution at 70 ° C., stirred for 1 hour with heat, filtered, washed with water and dried to obtain a fine diketopyrrolopyrrole pigment. When the obtained fine diketopyrrolopyrrole pigment was observed with a TEM (transmission electron microscope) and the image was analyzed to measure the particle diameter, the number average diameter was 27 nm, which was obtained by the production method of Comparative Example 1 shown below. Compared with the diketopyrrolopyrrole pigment, it was made finer. The amount of power energy input per kg of pigment was 11.2 kW / kg, which was 56% of that of Comparative Example 1.
Comparative Example 1
Diketopyrrolopyrrole pigment (CI Pigment Red 254, Ciba Specialty Chemicals “Irgafore Red B-CF”) 500 parts, sodium chloride 5000 parts, diethylene glycol 1100 parts double arm type 15000 parts by volume The kneader was charged and kneaded for 8 hours at 70 ° C. while maintaining a dense lump. After grinding, the mixture was taken out to 10000 parts of a 1% aqueous sulfuric acid solution at 70 ° C., and stirred for 1 hour, filtered, washed with water, and dried to obtain a diketopyrrolopyrrole pigment. The obtained diketopyrrolopyrrole pigment was observed with TEM, and the image was analyzed to measure the particle diameter. As a result, the number average diameter was 29 nm. Further, the input amount of electric power energy per 1 kg of the pigment was 20.0 kWH / kg.

Front view of planetary mixer

Explanation of symbols

1. 1. Planetary mixer body 2. Drive shaft Tank 4. blade

Claims (6)

It is characterized by kneading a mixture of an organic pigment (excluding a mixture of α-type phthalocyanine and ε-type phthalocyanine), a water-soluble inorganic salt, and a water-soluble organic liquid in a planetary mixer in which multiple blades move in a planetary motion. A method for producing a fine organic pigment. 2. The method for producing an organic fine pigment according to claim 1, wherein the organic pigment is a condensed polycyclic pigment. The number of blades is 3, The method for producing a fine organic pigment according to any one of claims 1 and 2. The mixture of the organic pigment, the water-soluble inorganic salt and the water-soluble organic liquid is 1 part by weight or more and 30 parts by weight or less of the water-soluble inorganic salt and 0.1 part by weight or more of the water-soluble organic liquid with respect to 1 part by weight of the organic pigment. The method for producing a fine organic pigment according to any one of claims 1 to 3, wherein the mixture comprises 7 parts by weight or less. The method for producing a fine organic pigment according to any one of claims 1 to 4, wherein a resin is further contained in a mixture of the organic pigment, the water-soluble inorganic salt, and the water-soluble organic liquid. 6. The method for producing a fine organic pigment according to claim 1, further comprising a pigment derivative in the mixture of the organic pigment, the water-soluble inorganic salt, and the water-soluble organic liquid.

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