Pigment compositions, coloring compositions, inks and printed materials

Abstract

The present invention aims to provide a pigment composition that can produce an ink with good viscosity stability, coloring power, and transparency. [Solution] A pigment composition comprising compound (A) represented by the following general formula (1) and compound (B) represented by the following general formula (2), wherein, in a total of 100 mol% of compound (A) and compound (B), compound (A) is present in an amount of 80-99 mol% and compound (B) in an amount of 1-20 mol%, and the specific surface area measured by the BET method is 30 m². 2 A pigment composition containing 1 / g or more. JPEG2026114952000020.jpg47144

Description

[Technical Field]

[0001] This invention relates to a pigment composition containing a disazo pigment. [Background technology]

[0002] Disazo pigments, a type of organic pigment, are characterized by high saturation and coloring power. These properties are important in the field of printing inks. When printing with overprints, highly transparent inks are needed to express colors through color mixing. To produce highly transparent inks, it is generally necessary to finely mill the pigment particles. When using disazo pigments in overprint inks, reducing the primary particle size of the pigment causes strong aggregation of the pigment particles, resulting in poor dispersibility. Furthermore, the resulting ink has low viscosity stability, and if the ink thickens over time, it becomes difficult to obtain suitable printed materials.

[0003] For example, Patent Document 1 discloses a composition containing a specific polymerized rosin component in an azo pigment for the purpose of improving viscosity stability and transparency. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 10-101958 [Overview of the project] [Problems that the invention aims to solve]

[0005] Even when conventional methods were applied to disazo pigments, it was not possible to satisfy all requirements regarding viscosity stability, clarity, and transparency.

[0006] The present invention aims to provide a pigment composition that can produce an ink with good viscosity stability, clarity, and transparency. [Means for solving the problem]

[0007] The pigment composition of the present invention comprises compound (A) represented by general formula (1) and compound (B) represented by general formula (2). Of the total 100 mol% of compound (A) and compound (B), compound (A) is present in 80 to 99 mol% and compound (B) in 1 to 20 mol% and has a specific surface area of ​​30 m² as measured by the BET method. 2 It is 1 / g or more.

[0008] General formula (1) [ka]

[0009] (In the formula, Ar1 and Ar2 represent aryl groups having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group.)

[0010] General formula (2) [ka]

[0011] (In the formula, Ar3 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. In the formula, Ar4 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, a sulfo group, and a sulfonate, except when all are hydrogen. Ar1, Ar2, and Ar3 are the same or different.) [Effects of the Invention]

[0012] The present invention provides a pigment composition that exhibits good viscosity stability and can produce inks with good clarity and transparency. Furthermore, the present invention can provide a coloring composition, an ink, a printed material, and a method for producing the pigment composition. [Modes for carrying out the invention]

[0013] Hereinafter, embodiments of the present invention will be described more specifically. The present invention is not limited to the following embodiments and can be variously modified within the scope capable of solving the problems.

[0014] The terms used in this specification will be explained. "C.I." represents a Color Index name. "Coated article" is synonymous with "printed matter", "image-formed matter", and "painted article". A to B means A or more and B or less.

[0015] <1>Pigment composition The pigment composition of the present invention contains a compound (A) represented by the following general formula (1) and a compound (B) represented by the following general formula (2). Among a total of 100 mol% of the compound (A) and the compound (B), the compound (A) is contained in an amount of 80 to 99 mol%, and the compound (B) is contained in an amount of 1 to 20 mol%, and the specific surface area measured by the BET method is 30 m 2 / g or more. Note that the pigment composition is in the form of particles.

[0016] The inventor speculates on the mechanism by which the pigment composition of the present invention can solve the problems as follows. Since particles with a large specific surface area mean particles with a small particle diameter, when an ink is prepared by refining a pigment composition containing a compound (A) represented by the general formula (1) and a compound (B) represented by the general formula (2) so that the specific surface area measured by the BET method is 30 m 2 / g or more, the dispersed particle diameter in the ink can be reduced. As a result, the clarity and transparency of the ink are improved. On the other hand, when the particle diameter of the compound (A) represented by the general formula (1) is refined, the dispersion stability decreases, and it easily aggregates over time in the ink and the ink tends to thicken. Therefore, when the compound (A) represented by the general formula (1) and the compound (B) represented by the general formula (2) are used in combination at an appropriate molar ratio, the electrostatic repulsion between the particles of the pigment composition due to the presence of the sulfo group or sulfonic acid group of the compound (B) prevents aggregation from occurring over time in the ink without impairing the clarity and transparency of the ink. As a result, the viscosity stability of the ink is improved.

[0017] Hereinafter, the compound (A) and the compound (B) will be sequentially described.

[0018] <Compound (A)> General formula (1) [ka]

[0019] In general formula (1), Ar1 and Ar2 represent aryl groups having the same or different substituents. The aryl group is preferably an aromatic hydrocarbon or heterocyclic compound such as phenyl, naphthyl, thienyl, or pyridyl. The substituents on the aryl group are preferably hydrogen atoms, alkyl groups, alkoxy groups, and halogen groups. The substituents may be the same or different and may be positioned at any position on the aryl group. The alkyl group is either linear or branched, and has 1 to 6 carbon atoms, more preferably 1 to 2, and even more preferably 1 carbon atom. The alkoxy group is linear, and the number of carbon atoms is preferably 1 to 6, more preferably 1 to 2, and even more preferably 1. Examples of halogen groups include fluorine, chlorine, bromine, and iodine. Among these, chlorine atoms or fluorine atoms are preferred, and chlorine atoms are more preferred. The compound represented by general formula (1) is preferably CIPigment Yellow 12, 13, 14, 17, or 83.

[0020] <Compound (B)> General formula (2) [ka]

[0021] In general formula (2), Ar3 represents an aryl group. The aryl group is preferably an aromatic hydrocarbon or heterocyclic compound such as phenyl, naphthyl, thienyl, or pyridyl. The substituents in the aryl group are preferably hydrogen atoms, alkyl groups, alkoxy groups, and halogen groups. The substituents may be the same or different and may be located at any position on the aryl group. The alkyl group is linear or branched, preferably having 1 to 6 carbon atoms, more preferably 1 to 2 carbon atoms, and even more preferably 1 carbon atom. The alkoxy group is linear, preferably having 1 to 6 carbon atoms, more preferably 1 to 2 carbon atoms, and even more preferably 1 carbon atom. Examples of the halogeno group include fluorine, chlorine, bromine, and iodine. Among these, a chlorine atom or a fluorine atom is preferred, and a chlorine atom is more preferred. In the formula, Ar4 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, a sulfo group, and a sulfonate, except when all are hydrogen. The aryl group is preferably an aromatic hydrocarbon or heterocyclic compound such as phenyl, naphthyl, thienyl, pyridyl, etc. The total number of sulfo groups and their salts is preferably 1 to 2. The hydrogen atom of the sulfo group can be substituted with a monovalent metal ion such as potassium or sodium depending on the pH. Ar1, Ar2, and Ar3 are the same or different.

[0022] In a total of 100 mol% of the compound (A) and the compound (B), 80 to 99 mol% of the compound (A) and 1 to 20 mol% of the compound (B) are contained. Preferably, 90 to 99 mol% of the compound (A) and 1 to 10 mol% of the compound (B) are contained, and more preferably, 95 to 99 mol% of the compound (A) and 1 to 5 mol% of the compound (B) are contained. By coexisting the compound of the general formula (2) within the above range, particle growth can be prevented and the particles can be refined.

[0023] The pigment composition of the present invention has a specific surface area measured by the BET method of 30 m 2 / g or more. The specific surface area is preferably 30 m 2 / g or more and 90 m 2 / g or less, and more preferably 30 m 2 / g or more and 59 m 2 / g or less. When it is 30 m 2 / g or more, a highly transparent ink can be obtained. Also, when it is 90 m 2 / g or less, the viscosity stability is further improved. The BET method is a type of method that involves adsorbing low-temperature N2 gas onto the surface of a particle, calculating the amount of adsorbed gas using the BET formula, and then determining the specific surface area.

[0024] <Dispersing agent> The pigment composition of the present invention may contain surfactants, rosin, and the like as dispersion aids. Surfactants include anionic, cationic, nonionic, and amphoteric surfactants. Examples of nonionic surfactants include the Emulgen series (manufactured by Kao Corporation), such as Emulgen 104P, Emulgen 105, Emulgen 106, Emulgen 108, Emulgen 109P, Emulgen 120, Emulgen 123P, Emulgen 147, Emulgen 150, Emulgen 210, Emulgen 220, Emulgen 306P, Emulgen 320P, Emulgen 350, Emulgen 404, Emulgen 408, Emulgen 409PV, Emulgen 420, Emulgen 430, Emulgen 705, Emulgen 707, Emulgen 709, and Emulgen A-60. Cationic surfactants include, for example, Acetamine 24 and Acetamine 86 from the Acetamine series (manufactured by Kao Corporation). Anionic surfactants include, for example, Demol N, Demol RN, Demol T, Demol SS, Poise 520, and Homogenol L-18 from the Demol series (manufactured by Kao Corporation), Poise series (manufactured by Kao Corporation), and Homogenol series (manufactured by Kao Corporation). The surfactant content is preferably 0.1 to 5.0% by mass of the nonvolatile content of the pigment composition.

[0025] The use of rosin reduces aggregation of the dried powder after pigment synthesis and improves dispersibility. Examples of rosin include disproportionated rosin, hydrogenated rosin, fumarated rosin, maleated rosin, ester gum, polymerized rosin, and rosin ester. Among these, disproportionated rosin, fumarated rosin, and maleated rosin are preferred. Examples of heterogeneous rosins include the Rondis series and Rosin Soap 20N from Arakawa Chemical Industries, and the Diplozine series from Toho Chemical Industries. Examples of fumarate rosin and maleide rosin include the Marquid series manufactured by Arakawa Chemical Industries, Ltd. Rosin can be used alone or in combination of two or more types. The rosin content is preferably 0.1 to 30% by mass of the nonvolatile content of the pigment composition.

[0026] <1> Preparation of a wet cake of a pigment composition The pigment composition described herein can be prepared by individually synthesizing compound (A) represented by general formula (1) and compound (B) represented by general formula (2) below, and then mixing them. Furthermore, another method for preparing the pigment compositions described herein allows for the simultaneous synthesis of compound (A) represented by general formula (1) and compound (B) represented by general formula (2). The above synthesis can be carried out by a coupling reaction between a diazonium salt obtained by diazotizing compound (C) (aromatic amine) represented by chemical formula (3), which is the base component, and compound (D) represented by general formula (4) and compound (E) represented by general formula (5), which are the coupler components.

[0027] [ka]

[0028] In general formula (4), Ar5 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. The aryl group is preferably an aromatic hydrocarbon or heterocyclic compound having a 5-membered ring to a 10-membered ring. Alkyl groups are linear or branched. The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 2, and even more preferably 1. Alkoxy groups are linear, and the number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 2, and even more preferably 1. Examples of halogen groups include fluorine, chlorine, bromine, and iodine. Among these, chlorine atoms or fluorine atoms are preferred, and chlorine atoms are more preferred.

[0029] In general formula (5), Ar6 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, a sulfo group, and a sulfonate, excluding the case where all substituents are hydrogen. The aryl group is preferably an aromatic hydrocarbon or heterocyclic compound such as phenyl, naphthyl, thienyl, or pyridyl. The total number of sulfo groups and sulfonates is preferably 1 to 2. The hydrogen atoms of the sulfo groups are substituted with monovalent metal ions such as potassium or sodium depending on the pH.

[0030] Two synthesis methods are shown below. The first method involves preparing a solution containing compound (D) represented by general formula (4) and compound (E) represented by general formula (5), which are coupler components, and then synthesizing a pigment composition containing compound (A) and compound (B) by coupling reaction with a solution containing a diazonium salt. A second method involves preparing solutions containing only the first coupler component and solutions containing only the second coupler component, and then synthesizing pigment compositions containing compound (A) and compound (B) by sequentially performing coupling reactions. The order in which compounds (D) and (E) are added does not matter.

[0031] A solution containing the coupler components, compound (D) represented by general formula (4) and compound (E) represented by general formula (5), can be prepared by dissolving the coupler components in a basic aqueous solution heated to approximately 20-30°C. Alternatively, the coupler components may be dissolved by mixing water, a water-soluble organic solvent, the coupler components, and a base at approximately 20-30°C.

[0032] The base dissolves in water and dissolves the coupler components. The base is preferably a compound that does not form an insoluble salt when neutralized with the acid in the acid aqueous solution or the acid in the solution containing the diazonium salt described later. For example, sodium hydroxide and potassium hydroxide are more preferred bases. This reduces costs, improves the dissolving power of the coupler components, and facilitates wastewater treatment.

[0033] Solutions containing diazonium salts are obtained by diazotizing the base component. Diazotization can be performed, for example, by adding hydrochloric acid or sulfuric acid to a slurry of the base component in ice water, dissolving it, and then adding sodium nitrite to carry out the diazotization. Another method involves adding a water-soluble organic solvent to the solution containing the diazonium salt.

[0034] Methods for coupling reactions include so-called reverse coupling, forward coupling, acid precipitation forward coupling, and parallel injection. Among these, acid precipitation forward coupling, described later, is preferred from the viewpoint of particle size control and reaction yield.

[0035] One method of reverse coupling is to add a solution containing a coupler component to a solution containing a diazonium salt.

[0036] One method for positive coupling is to add a solution containing a diazonium salt to a solution containing a coupler component.

[0037] One method for acid precipitation positive coupling involves reacting a solution containing the coupler component with an acidic aqueous solution to obtain an acid precipitation coupler slurry. Then, a solution containing the diazonium salt is added to the obtained acid precipitation coupler slurry to carry out the coupling reaction. The temperature of the acidic aqueous solution during acid precipitation is preferably 0 to 30°C. From the viewpoint of improving the reaction rate, the acid precipitation coupler slurry can be heated as needed before adding the solution containing the diazonium salt. However, to suppress alteration or decomposition of the diazonium salt, the temperature of the acid precipitation coupler slurry during the coupling reaction is preferably 50°C or lower. Furthermore, the pH of the acid precipitation coupler slurry before adding the solution containing the diazonium salt is preferably 2 to 6.5 from the viewpoint of reaction rate and reaction efficiency. Any acid that dissolves in water can be used to adjust the pH, but hydrochloric acid, acetic acid, or a mixture of hydrochloric acid and acetic acid is preferred. Methods for adding acid include adding the acid to be used for acid precipitation in excess of the base in the solution containing the coupler component, adding it in advance when the base is dissolved, adding it to the solution containing the diazonium salt, or adding the required amount to the coupler slurry after acid precipitation. Furthermore, from the viewpoint of improving the reaction rate and dispersibility, it is preferable to heat the slurry after coupling as needed. The heating temperature is preferably 50 to 90°C, and acid or base may be added during heating as needed.

[0038] One example of a parallel injection method is to continuously add a solution containing a coupler component and a solution containing a diazonium salt to an acidic aqueous solution.

[0039] The slurry of the pigment composition obtained by the coupling reaction can be used to remove water, water-soluble organic solvents, water-soluble salts, etc., using known suction filters, filter presses, ultrafilters, etc. In this way, a wet cake of the pigment composition is obtained. It is preferable to remove the water so that the solid content of the wet cake of the pigment composition is 25 to 40% by mass.

[0040] When manufacturing the pigment composition of the present invention, a dispersion aid may be used as needed. Examples of dispersion aids include the surfactants already exemplified. The dispersion aid can be used at any time during the manufacturing process.

[0041] <2> Method for manufacturing pigment compositions The method for producing the pigment composition described herein involves drying a wet cake of the pigment composition and obtaining a specific surface area of ​​30 m² as measured by the BET method. 2 This is a method for obtaining powder of a quantity of / g or more. The pigment composition comprises compound (A) represented by general formula (1) and compound (B) represented by general formula (2), wherein compound (A) accounts for 80 to 99 mol% and compound (B) accounts for 1 to 20 mol% of the total 100 mol% of compound (A) and compound (B).

[0042] The resulting pigment composition wet cake is dried by removing moisture through a drying process. Methods for supplying the wet cake to the dryer include continuous and batch methods. Drying methods include hot air heating and conductive heating. Among these, hot air heating is preferred, and continuous hot air heating drying is more preferred. Examples of continuous hot air heating drying methods include rotary dryers and band dryers. Among these, band dryers are preferred. A band dryer is a device that can continuously dry materials with hot air while transporting them using a belt conveyor or the like.

[0043] The drying temperature of the band dryer is preferably around 100°C to 150°C, and more preferably between 100°C and 130°C. This suppresses aggregation of the pigment composition during drying. A temperature gradient may be provided for the drying temperature.

[0044] The drying time in the band dryer is preferably 1 to 10 hours, and more preferably 1 to 4 hours. Shortening the drying time reduces the thermal energy applied to the wet cake of the pigment composition, thereby suppressing aggregation. This improves the transparency of the ink when using the pigment composition to produce ink.

[0045] Since the pigment composition remains in a lumpy state after drying, it can be pulverized to produce a powdered pigment composition. Grinding equipment includes, for example, high-speed rotary grinders. Examples of high-speed rotary grinders include hammer mills, gauge mills, pin mills, disintegrators, screen mills, turbo mills, and centrifugal classification mills. The pigment composition obtained by the aforementioned drying and grinding has a specific surface area of ​​30 m² as measured by the BET method. 2 A value of 1 / g or more is preferred. The specific surface area should be 90 m². 2 Preferably less than / g

[0046] <3> coloring composition The coloring compositions described herein may contain the pigment composition and resin of the present invention. Examples of resins include dispersion resins and binder resins. Examples of the resin types used for the dispersion resin and binder resin include acrylic resin, epoxy resin, alkyd resin, phenolic resin, polyurethane resin, polyester resin, vinyl resin, and polyvinyl chloride resin. These resins can improve properties such as adhesion, hardness, flexibility, gloss, solubility, and stability when the colored composition is turned into an ink and formed into a coating film. Block polymers and comb polymers are preferred as the dispersion resin form. Random polymers are preferred as the binder resin form.

[0047] The pigment composition content is preferably 10 to 90% by mass, and more preferably 40 to 60% by mass, of the nonvolatile content of the coloring composition.

[0048] The resin content is preferably 10 to 90% by mass, and more preferably 40 to 60% by mass, of the nonvolatile content of the colored composition.

[0049] Applications of the colored composition of the present invention include paints, solvent-based printing inks, water-based printing inks, and active energy ray-curable printing inks. Ink can be any color, such as black, white, red, orange, yellow, green, blue, indigo, purple, or combinations thereof. Ink is used in applications such as pens, printers, and markers. The ink can be used for coloring and printing on substrates such as paper, cloth, plastic, metal, wood, glass, and ceramics.

[0050] Ink can be used for printing. This ink is called printing ink. Printing methods include plate printing such as lithography, intaglio printing, relief printing, and stencil printing, and plateless printing such as inkjet printing and electrophotography. Among these, gravure printing is preferred.

[0051] <4> Printing ink The printing ink preferably contains a pigment composition, and further contains a resin and a solvent. Printing inks can be further subdivided according to the printing format, for example, into inks for offset printing, flexographic printing, gravure printing, color filter inks, inkjet printing inks, etc. The pigment composition of this embodiment has excellent dispersibility, as well as excellent coloring power, vividness, and transparency, and can therefore be used in a variety of printing inks.

[0052] Examples of resins used in the printing inks described herein include acrylic resins, epoxy resins, alkyd resins, phenolic resins, polyurethane resins, polyester resins, silicone resins, vinyl resins, polypropylene chloride resins, polyvinyl chloride resins, rosin resins, rosin-modified phenolic resins, nitrocellulose, styrene-acrylic resins, petroleum resins, and the like. The resin used to prepare the printing ink may be the same as or different from the resin in the coloring composition.

[0053] Solvents contained in printing inks include hydrophilic organic solvents, hydrophobic organic solvents, and water. Examples of hydrophilic organic solvents include alkyl alcohols, glycols, and polyhydric alcohol-modified monoalcohols. Examples of alkyl alcohols include ethanol, n-propanol, isopropanol, and isobutanol. Examples of glycols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, and glycerin. Examples of polyhydric alcohol-modified monoalcohols include methoxypropanol or methoxybutanol. Examples of water-soluble organic solvents include aliphatic hydrocarbons, aromatic hydrocarbons, ketones, and esters. Aliphatic hydrocarbons may be straight-chain, branched-chain, or cyclic, and examples include straight-chain and branched-chain C5-C10 alkanes and methylcyclohexane. Aromatic hydrocarbons include toluene and xylene. Examples of ketones include methyl ethyl ketone and methyl isobutyl ketone. Examples of esters include ethyl acetate, propyl acetate, and butyl acetate. Other solvents commonly used in the ink industry are also included.

[0054] The pigment composition content is preferably 10 to 80% by mass, and more preferably 30 to 50% by mass, relative to the non-volatile content of the ink.

[0055] The resin content is preferably 20 to 90% by mass, and more preferably 50 to 70% by mass, relative to the non-volatile content of the ink.

[0056] The printing ink may further contain other components. For example, it may contain, as needed, coloring pigments commonly used in the art and various additives. The method for manufacturing the printing ink, and the method for applying and drying it, are not particularly limited, and methods well known in the art can be used.

[0057] The printed materials of the present invention are made by printing with the ink of the present invention. Examples of printed materials include books, newspapers, magazines, brochures, flyers, posters, maps, tickets, cards, labels, packaging, clothing, wallpaper, signs, and the like. Examples of substrate types include paper, polyethylene terephthalate (PET) film, and biaxially oriented polypropylene (OPP) film. The substrate thickness is preferably 10 to 1000 μm. The ink layer thickness is preferably 0.5 to 50 μm. Printing methods include, for example, gravure printing and offset printing.

[0058] [Example of an embodiment] Examples of embodiments of the present invention are given below. The present invention is not limited to the following.

[0059] <1> The pigment composition of the present invention comprises compound (A) represented by the following general formula (1) and compound (B) represented by the following general formula (2). The compound (A) and (B) together make up 100 mol% of the total, with 80-99 mol% of compound (A) and 1-20 mol% of compound (B), and having a specific surface area of ​​30 m² as measured by the BET method. 2 It is 1 / g or more. General formula (1) [ka]

[0060] (In the formula, Ar1 and Ar2 represent aryl groups having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group.) General formula (2) [ka]

[0061] (In the formula, Ar3 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. In the formula, Ar4 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, a sulfo group, and a sulfonate, except when all substituents are hydrogen. Ar1, Ar2, and Ar3 are the same or different.) <2> <1> A pigment composition and a coloring composition comprising a resin. <3> <1> An ink containing a pigment composition. <4> <3> A printed material made by printing with ink. <5> A wet cake of a pigment composition containing the pigment composition described below is dried using a continuous hot air heat-receiving drying method, and the specific surface area measured by the BET method is 30 m². 2 A method for producing a pigment composition that yields a powder of 1 / g or more. The pigment composition comprises compound (A) represented by the following general formula (1) and compound (B) represented by the following general formula (2), wherein compound (A) accounts for 80 to 99 mol% and compound (B) accounts for 1 to 20 mol% of the total 100 mol% of compound (A) and compound (B). General formula (1) [ka]

[0062] (In the formula, Ar1 and Ar2 represent aryl groups having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group.) General formula (2) [ka]

[0063] (In the formula, Ar3 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. In the formula, Ar4 represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, a sulfo group, and a sulfonate, except when all substituents are hydrogen. Ar1, Ar2, and Ar3 are the same or different.) [Examples]

[0064] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. "Parts" refers to "parts by mass," and "%" refers to "percentage by mass."

[0065] The abbreviations used in the examples have the following meanings: <Coupler> AAOT:2'-Methylacetoacetanilide AS-IRG: 4'-Chloro-2',5'-dimethoxyacetoacetanilide AAA: Acetacetanilide AAMX:2',4'-Dimethylacetoacetanilide AAOA: 2'-Methoxyacetonealide AASP: Potassium 4'-acetoacetylaminobenzenesulfonate

[0066] The surfactants and rosins used in the following examples are as follows: <Nonionic surfactants> Emulgen 105: Manufactured by Kao Corporation Toho Hall N-220: Manufactured by Toho Chemical Industry Co., Ltd. Emulgen A-60: Manufactured by Kao Corporation <Cationic surfactants> Acetamine 86: Manufactured by Kao Corporation Acetamine 24: Manufactured by Kao Corporation <Rosin> Rosin Soap 20N: Manufactured by Arakawa Chemical Industries, Ltd. Diplozine K-25: Manufactured by Toho Chemical Industry Co., Ltd.

[0067] The drying conditions for the wet cake of the pigment composition are shown below. Drying conditions A: The wet cake of the obtained pigment composition was placed in a band-type dryer (manufactured by Changzhou Yalong Drying Equipment Co., Ltd.) and dried at "120°C to 130°C for 75 minutes, 105°C to 115°C for 100 minutes, and 65°C for 25 minutes". Drying condition B: The wet cake of the obtained pigment composition was placed in a band-type dryer (manufactured by Changzhou Yalong Drying Equipment Co., Ltd.) and dried at "140°C to 150°C for 75 minutes, 130°C to 140°C for 100 minutes, and 65°C for 25 minutes". Drying condition C: The wet cake of the obtained pigment composition was placed in a box-type dryer (manufactured by Nippon Drying Machine Co., Ltd.) and dried at 100°C for 1440 minutes. Drying condition D: The wet cake of the obtained pigment composition was placed in a band-type dryer (manufactured by Changzhou Yalong Drying Equipment Co., Ltd.) and dried at "120°C to 130°C for 95 minutes, 105°C to 115°C for 120 minutes, and 65°C for 25 minutes". Drying condition E: The wet cake of the obtained pigment composition was placed in a band-type dryer (manufactured by Changzhou Yalong Drying Equipment Co., Ltd.) and dried at "140°C to 150°C for 65 minutes, 130°C to 140°C for 80 minutes, and 65°C for 15 minutes".

[0068] (Example 1) Preparation of Pigment Composition 1 <Synthesis> In a reaction vessel equipped with a stirring device, 5.48 parts of water and 10.0 parts of 3,3'-dichlorobenzidine as the base component were added and stirred. Further stirring, 8.6 parts of 35% hydrochloric acid and 2.3 parts of 98% sulfuric acid were added. 40.4 parts of ice were added to this solution to cool it to 0°C, and then 5.5 parts of sodium nitrite were added and stirred for 1 hour. Next, a small amount of sulfamic acid was added to eliminate the excess sodium nitrite, and then 158.2 parts of water were added to obtain a tetrazo solution of 3,3'-dichlorobenzidine. Separately, 15.7 parts of AAOT and 0.4 parts of AASP as coupler components were added to 58.7 parts of water in a reaction vessel equipped with a stirring device. Further stirring was performed by adding 18.2 parts of 25% aqueous sodium hydroxide solution. A mixture of 9.1 parts of 80% acetic acid and 79.2 parts of water was gradually added to this solution to form a suspension, and the tetrazo solution was uniformly added dropwise to the suspension over 80 minutes. When adding the tetrazo solution dropwise, the reaction temperature was maintained at approximately 20°C with a pH of 4-6. To the resulting disazo pigment slurry, 0.4 parts of Emulgen 105 were added as a surfactant. The mixture was then heated to 60°C and held for 30 minutes. Next, the pH was adjusted to 9.0 with a 25% sodium hydroxide aqueous solution, and after stirring for 10 minutes, the mixture was filtered, washed with water, and pressed to obtain a wet cake of the pigment composition with a pigment content of 30.0%.

[0069] <Drying> The wet cake of the obtained pigment composition was dried under drying condition A to obtain a lump-type pigment composition.

[0070] <Crushing> The bulk pigment composition was pulverized with a hammer mill to obtain pigment composition 1 containing 96.66 mol% of compound (A) and 3.34 mol% of compound (B).

[0071] (Examples 2-6 and 13-18) Preparation of pigment compositions 2-6 and 13-18 Pigment compositions 2 to 18 were obtained in the same manner as in Example 1, except for the following three changes. The changes are shown below as (1) to (3). (1) The coupler solution used in Example 1 consisted of 15.7 parts AAOT and 0.4 parts AASP, but the types and amounts (parts) of the first and second couplers shown in Table 1 were used instead, and these two types of coupler components were mixed to make the coupler solution. (2) The emulsion 105 used in Example 1 as a dispersing agent was changed from 0.4 parts to the type and amount (parts) of the dispersing agent shown in Table 1. (3) The samples were dried according to the drying conditions described in Table 1.

[0072] (Example 7) Preparation of pigment composition 7 The synthesis of pigment composition 1 was modified as follows. Otherwise, pigment composition 7 was obtained in the same manner as in Example 1. <Synthesis> 5.48 parts water and 10.0 parts 3,3'-dichlorobenzidine as the base component were added to a reaction vessel equipped with a stirring device. Furthermore, 8.6 parts 35% hydrochloric acid and 2.3 parts 98% sulfuric acid were added. 40.4 parts ice was added to this solution to cool it to 0°C, and then 5.5 parts sodium nitrite was added and the mixture was stirred for 1 hour. A small amount of sulfamic acid was added to remove the excess sodium nitrite, and then 158.2 parts water was added to obtain a tetrazo solution of 3,3'-dichlorobenzidine. Separately, 58.7 parts water and 22.5 parts AS-IRG and 0.4 parts AASP as coupler components were added to a reaction vessel equipped with a stirring device. 18.2 parts 25% aqueous sodium hydroxide solution was added to the reaction vessel and dissolved. This solution was gradually added to a mixture of 9.1 parts 80% acetic acid, 79.2 parts water, and 0.9 parts acetamine 86 dissolved in hot water to form a suspension. The tetrazo solution was uniformly added dropwise to the suspension over 80 minutes. During the addition of the tetrazo solution, the pH was maintained at 4-6 and the reaction temperature at approximately 20°C. The mixture was then heated to 90°C and held there for 30 minutes. After cooling to 70°C, the pH was adjusted to 9.0 with a 25% sodium hydroxide aqueous solution, and after stirring for 10 minutes, the mixture was filtered, washed with water, and pressed to obtain a wet cake of the pigment composition containing 29.4% pigment components.

[0073] (Example 8) Preparation of pigment composition 8 The synthesis of pigment composition 1 was modified as follows. Otherwise, pigment composition 8 was obtained in the same manner as in Example 1. <Synthesis> 5.48 parts water and 10.0 parts 3,3'-dichlorobenzidine as the base component were added to a reaction vessel equipped with a stirring device. Furthermore, 8.6 parts 35% hydrochloric acid and 2.3 parts 98% sulfuric acid were added. 40.4 parts ice was added to this solution to cool it to 0°C, then 5.5 parts sodium nitrite was added and the mixture was stirred for 1 hour. A small amount of sulfamic acid was added to remove excess sodium nitrite, and then 158.2 parts water was added to obtain a tetrazo solution of 3,3'-dichlorobenzidine. Separately, 58.7 parts water and 22.5 parts AS-IRG and 0.4 parts AASP as coupler components were added to a reaction vessel equipped with a stirring device. 18.2 parts 25% sodium hydroxide aqueous solution was added to the reaction vessel and dissolved. A mixture of 9.1 parts 80% acetic acid and 79.2 parts water was gradually added to this solution to form a suspension. 0.9 parts acetamine 24 was added to the suspension. The tetrazo solution was added to this solution over a period of approximately 80 minutes. During the addition of the tetrazo solution, the pH was maintained between 4 and 6 and the reaction temperature was kept at approximately 20°C. The mixture was then heated to 90°C and held therefore for 60 minutes. After cooling to 70°C, the mixture was filtered, washed with water, and pressed to obtain a wet cake of the pigment composition with a pigment content of 28.7%.

[0074] (Example 9) Preparation of pigment composition 9 In pigment composition 7, 0.9 parts of acetamine 86 were replaced with 0.0 parts. Otherwise, pigment composition 9 was obtained in the same manner as in Example 7.

[0075] (Example 10) Preparation of pigment composition 10 The synthesis of pigment composition 1 was modified as follows. Otherwise, pigment composition 10 was obtained in the same manner as in Example 1. <Synthesis> 5.48 parts water and 10.0 parts 3,3'-dichlorobenzidine as the base component were added to a reaction vessel equipped with a stirring device. Furthermore, 8.6 parts 35% hydrochloric acid and 2.3 parts 98% sulfuric acid were added. 40.4 parts ice was added to this solution to cool it to 0°C, then 5.5 parts sodium nitrite was added and the mixture was stirred for 1 hour. A small amount of sulfamic acid was added to remove excess sodium nitrite, and then 158.2 parts water was added to obtain a tetrazo solution of 3,3'-dichlorobenzidine. Separately, 58.7 parts water, 14.6 parts AAA and 0.4 parts AASP as coupler components were added to a reaction vessel equipped with a stirring device. 18.2 parts 25% aqueous sodium hydroxide solution was added to the reaction vessel and dissolved. A mixture of 9.1 parts 80% acetic acid and 79.2 parts water was gradually added to this solution to form a suspension. The tetrazo solution was then added to the suspension over a period of approximately 80 minutes. When adding the tetrazo solution, the pH was maintained between 4 and 6 and the reaction temperature was kept at approximately 20°C. Afterward, the pH was adjusted to 10.5 with a 25% sodium hydroxide aqueous solution, and then 0.4 parts of Diplozin K-25 were added and the mixture was held for 20 minutes. After cooling to 70°C, the mixture was filtered, washed with water, and pressed to obtain a wet cake containing 28.7% pigment.

[0076] (Examples 11 and 12) Preparation of pigment compositions 11 and 12 The synthesis of pigment composition 8 was modified as follows. Otherwise, pigment compositions 11 and 12 were obtained in the same manner as in Example 8. (Changes) (1) Instead of using 22.5 parts AS-IRG and 0.4 parts AASP as the coupler solution in Example 8, the types and amounts (parts) of the first and second couplers shown in Table 1 were used, and these two types of coupler components were mixed to make the coupler solution. (2) Instead of 0.9 parts of acetamine 24 used in Example 8 as a dispersing agent, the type and amount (parts) of the dispersing agent shown in Table 1 were used.

[0077] (Example 19) Preparation of pigment composition 19 The synthesis of pigment composition 1 was modified as follows. Otherwise, pigment composition 19 was obtained in the same manner as in Example 1. <Synthesis> 5.48 parts water and 10.0 parts 3,3'-dichlorobenzidine as the base component were added to a reaction vessel equipped with a stirring device. 8.6 parts 35% hydrochloric acid and 2.3 parts 98% sulfuric acid were added to the reaction vessel. 40.4 parts ice was added to this solution to cool it to 0°C, then 5.5 parts sodium nitrite was added and the mixture was stirred for 1 hour. A small amount of sulfamic acid was added to remove the excess sodium nitrite, and then 158.2 parts water was added to obtain a tetrazo solution of 3,3'-dichlorobenzidine. Separately, 9.1 parts 80% acetic acid, 200.0 parts water, and 0.4 parts Emulgen A-60 were added to a tank equipped with a stirring device and stirred for 30 minutes to obtain an acetic acid mixture. Separately, 22.5 parts AS-IRG and 0.4 parts AASP as coupler components were added to 58.7 parts water in a reaction vessel equipped with a stirring device. 18.2 parts 25% sodium hydroxide aqueous solution was added to the reaction vessel and dissolved. This dissolution was gradually added to the acetic acid mixture to form a suspension. The tetrazo solution was added to the suspension over a period of approximately 80 minutes. During the addition of the tetrazo solution, the pH was maintained between 4 and 6 and the reaction temperature was kept at approximately 10°C. Meanwhile, a xylene emulsion solution was prepared using 22.6 parts water, 5.8 parts xylene, and 0.3 parts Touhol N-220 (78% water, 20% xylene, 2% Touhol). The xylene emulsion solution was added to the resulting disazo pigment slurry, the pH was adjusted to 11.0, and the mixture was heated to 90°C and held for 30 minutes. 18.8 parts of rosin soap 20N and 6.5 parts of 8% aluminum sulfate aqueous solution were added. After adjusting the pH to 6.0, the mixture was stirred for 10 minutes, filtered, washed with water, and pressed to obtain a wet cake of the pigment composition with a pigment content of 30.0%.

[0078] (Example 20) Preparation of pigment composition 20 Pigment composition 20 was obtained in the same manner as in Example 5, except that the drying conditions for pigment composition 5 were changed to drying condition D.

[0079] (Example 21) Preparation of pigment composition 21 Pigment composition 21 was obtained in the same manner as in Example 13, except that the drying conditions for pigment composition 13 were changed to drying condition E.

[0080] [Table 1]

[0081] (Comparative Examples 101-106 and 113) Preparation of Pigment Compositions 101-106 and 113 Pigment compositions 101-106 and 113 were obtained in the same manner as in Example 1, except for the following three changes. The changes are shown below as (1)-(3). (1) The coupler solution used in Example 1 consisted of 15.7 parts AAOT and 0.4 parts AASP, but the types and amounts (parts) of the first and second couplers shown in Table 2 were used instead, and these two types of coupler components were mixed to form the coupler solution. (2) The amount of Emulgen 105 used in Example 1 as a dispersing agent was changed to 0.4 parts, and the type and amount (parts) of the dispersing agent shown in Table 2 was used instead. (3) The samples were dried under the drying conditions shown in Table 2. A list of the changes is shown in Table 2.

[0082] (Comparative Examples 107, 109, 114 and 115) Preparation of Pigment Compositions 107, 109, 114 and 115 Pigment compositions 107 and 109 were obtained in the same manner as in Example 7, except that the following three points were changed. The changes are shown below as (1) and (2). (1) The coupler solution used in Example 1 consisted of 22.5 parts AS-IRG and 0.4 parts AASP. The types and amounts (parts) of the first and second couplers shown in Table 2 were used instead, and these two types of coupler components were mixed to form the coupler solution. (2) Instead of using 0.9 parts of acetamine 86 as a dispersing agent in Example 7, the type and amount (parts) of the dispersing agent shown in Table 2 were used. (3) The drying was carried out under the drying conditions shown in Table 2. A list of the changes is shown in Table 2.

[0083] (Comparative Example 108) Preparation of Pigment Composition 108 In Example 8, the drying method was changed from condition A to condition C. Otherwise, the procedure was the same as in Example 8.

[0084] (Comparative Example 110) Preparation of Pigment Composition 110 Pigment composition 110 was obtained in the same manner as in Example 10, except for the following three changes. The changes are shown below as (1) to (3). (1) Changed AASP from 0.4 parts to 0.0 parts. (2) Diplozine K-25 was changed from 0.4 parts to 0.0 parts. (3) The samples were dried under the drying conditions shown in Table 2. Otherwise, the procedure was the same as in (Example 10).

[0085] (Comparative Examples 111 and 112) Preparation of Pigment Compositions 111 and 112 Pigment compositions 111 and 112 were obtained in the same manner as in Example 11, except for the following three changes. The changes are shown below as (1) to (3). (1) The coupler solution was prepared by replacing the 17.0 parts of AAMX and 0.4 parts of AASP used in Example 11 with the type and amount of couplers (parts) shown in Table 2. (2) The mass of acetamine 24 was changed to 0.0 parts. (3) The samples were dried under the drying conditions shown in Table 2. Otherwise, the procedure was the same as in (Example 11).

[0086] (Comparative Example 116) Preparation of Pigment Composition 116 The following two points were modified from (Example 19). Otherwise, the procedure was the same as in (Example 19). (1) The AASP was changed from 0.4 units to 0.0 units. (2) The drying conditions were changed from A to C.

[0087] [Table 2]

[0088] <Degree of pigment fineness> The degree of pigment refinement was evaluated by the specific surface area of ​​the pigment particles. The specific surface area was measured using a fully automated specific surface area measuring device (HM model-1201, manufactured by Mountec Co., Ltd.) based on the BET flow method (based on JIS Z8830:2013). The specific surface area results for the obtained pigment compositions are shown in Tables 3 and 4.

[0089] <mol% of compound A and compound B> The mole percentages of compound A and compound B were calculated for the obtained pigment compositions as follows. A calibration curve was created using a scanning X-ray fluorescence analyzer (Rigaku ZSX Primus II) for the ratio of the X-ray intensity of sulfur atoms to the X-ray intensity of chlorine atoms (hereinafter referred to as S / Cl) and the mole percentage of compound B. The calibration curve can be expressed as y = 46.2x (y: mole percent of compound B, x: S / Cl). Using this, the molar percentages of compound A and compound B in the pigment composition were calculated.

[0090] [Table 3]

[0091] [Table 4]

[0092] <Manufacturing and evaluation of gravure inks> • Creation of gravure inks First, the hydroxyl value, acid value, amine value, and weight-average molecular weight of the resin are as follows: (Hydroxyl value) The results were obtained according to JIS K0070. (Acid value) The results were obtained according to JIS K0070. (Amine value) The amine value was determined according to JIS K0070, using the following method, which is the same amount of potassium hydroxide (in mg) as the equivalent amount of hydrochloric acid required to neutralize the amino groups contained in 1 g of resin. 0.5 to 2 g of the sample was accurately weighed (sample non-volatile content: S g). 50 mL of a methanol / methyl ethyl ketone (60 / 40 mass ratio) mixture was added to the accurately weighed sample and dissolved. Bromophenol blue was added to the resulting solution as an indicator, and the solution was titrated with a 0.2 mol / L ethanolic hydrochloric acid solution (titer: f). The endpoint was defined as the point where the solution color changed from green to yellow. The titration volume (A mL) at this point was used to determine the amine value using the following formula. Amine value = (A × f × 0.2 × 56.108) / S [mgKOH / g]

[0093] (Weight average molecular weight) The weight-average molecular weight was determined by measuring the molecular weight distribution using a GPC (gel permeation chromatography) instrument (HLC-8220, Tosoh Corporation) and calculating the converted molecular weight using polystyrene as the standard substance. The measurement conditions are shown below. Columns: The following columns were used, connected in series. Tosoh Corporation Guard Column HXL-H TSKgel G5000HXL manufactured by Tosoh Corporation TSKgel G4000HXL manufactured by Tosoh Corporation TSKgel G3000HXL manufactured by Tosoh Corporation TSKgel G2000HXL manufactured by Tosoh Corporation Detector: RI (Differential Refractometer) Measurement conditions: Column temperature 40°C Eluent: Tetrahydrofuran Flow rate: 1.0mL / min

[0094] (Glass transition temperature) The glass transition temperature (Tg) was determined by differential scanning calorimetry (DSC). A Rigaku DSC8231 was used, with a measurement temperature range of -70 to 250°C, a heating rate of 10°C / min, and the midpoint between the endothermic start temperature and end temperature based on the glass transition in the DSC curve was defined as the glass transition temperature.

[0095] (Synthesis Example 1) [Polyurethane resin PU1] 200 parts by mass of polypropylene glycol (hereinafter "PPG700") with a number-average molecular weight of 700, 127 parts by mass of isophorone diisocyanate (hereinafter "IPDI"), and 81.8 parts by mass of ethyl acetate were reacted at 80°C for 4 hours under a nitrogen stream to obtain a resin solution of terminal isocyanate urethane prepolymer. Next, 49.5 parts by mass of isophorone diamine (hereinafter "IPDA"), 3 parts by mass of 2-ethanolamine, and 803.9 parts by mass of a mixed solvent of ethyl acetate / isopropanol (hereinafter "IPA") = 50 / 50 (mass ratio) were mixed together. The obtained resin solution of terminal isocyanate urethane prepolymer was gradually added to this mixture at 40°C, and then reacted at 80°C for 1 hour to obtain a polyurethane resin solution PU1 with a non-volatile content of 30%, an amine value of 3.5 mg KOH / g, a hydroxyl value of 7.3 mg KOH / g, and a weight-average molecular weight of 40000. The glass transition temperature of the resin was -32°C.

[0096] (Example A-1) Preparation of gravure ink a-1 As a binder resin, 30 parts by mass of polyurethane resin solution PU1 (30% non-volatile content), 0.8 parts by mass of polyethylene wax (Honeywell A-C400A) as a hydrocarbon wax (calculated on a non-volatile content basis), 0.5 parts by mass of chlorinated polypropylene resin (Nippon Paper Industries 370M, 30% chlorine content, 50% non-volatile content) (calculated on a non-volatile content basis), 10 parts by mass of pigment composition 1, and 58.7 parts by mass of a mixed solvent consisting of methyl ethyl ketone (hereinafter "MEK") / n-propyl acetate (hereinafter "NPAC") / IPA = 40 / 40 / 20 (mass ratio) were mixed and dispersed in an Eiger mill for 15 minutes to obtain gravure ink a-1.

[0097] (Examples A-2 to A-21, Comparative Examples A-101 to A-116) Preparation of gravure inks a-2 to a-21 and a-101 to a-116 Except for changing pigment composition 1 of Example A-1 as shown in Table 5, the procedure was carried out in the same manner as in Example A-1 to obtain gravure inks a-2 to a-21 and a-101 to a-116.

[0098] Production of gravure ink printed materials The obtained gravure ink was diluted with a mixed solvent consisting of MEK / NPAC / IPA = 40 / 40 / 20 (mass ratio) to a viscosity of 16 seconds (25°C, Zahn cup No. 4). The diluted solution was then printed onto the following substrates (corona discharge treated surface for clarity) using a gravure printing press equipped with a Helio 175-line gradient plate (compressed gradient plate type 100%~3%) at a printing speed of 80 m / min on the OPP substrate to obtain OPP printed materials. (base material) • OPP: Biaxially oriented polypropylene (OPP) film with corona discharge treatment on one side (Futamura Chemical Co., Ltd., FOR, 25 μm thickness)

[0099] <Evaluation of gravure inks and printed materials> Regarding the color evaluation items (vividness, transparency), since the hue differs depending on the pigment type, evaluation was performed for each of the four hue groups according to the method described above. Hue Group 1 used Comparative Example A-113 (gravure ink a-113) as the evaluation standard. Hue Group 2 used Comparative Example A-116 (gravure ink a-116) as the evaluation standard. Hue Group 3 used Comparative Example A-110 (gravure ink a-110) as the evaluation standard. Hue Group 4 used Comparative Example A-111 (gravure ink a-111) as the evaluation standard. Hue Group 5 used Comparative Example A-112 (gravure ink a-112) as the evaluation standard. The group divisions are shown in Tables 5 and 6, and in each hue group, the row marked with * is the comparative example used as the evaluation standard for color evaluation.

[0100] (Ink viscosity stability) The prepared gravure ink was placed in a sealed container and stored at 40°C for 10 days. Afterward, the viscosity was measured to evaluate the change in viscosity compared to before storage. Viscosity was measured at 25°C using a Zahn cup No. 4 in seconds. The results are shown in Tables 5 and 6. A score of "4" or "3" according to the evaluation criteria below indicates a usable level. (Evaluation criteria for viscosity stability) 4. Viscosity change in less than 2 seconds. (Excellent) 3. Viscosity change between 2 seconds and less than 5 seconds. (Good) 2. Viscosity change between 5 seconds and less than 10 seconds. (Defective) 1: Viscosity change between 10 seconds and less than 15 seconds. (Extremely poor)

[0101] (Clarity) The obtained OPP printed materials were visually inspected and evaluated according to the following criteria. The results are shown in Tables 5 and 6. A score of "4" or "3" according to the evaluation criteria below indicates a level that is usable. (Criteria for evaluating clarity) 4. The image is significantly clearer than the reference print. (Excellent) 3: The image is clearer than the reference print. (Good) 2. Sharpness equivalent to the reference print. (Poor) 1: The clarity is lower than the reference print. (Extremely poor)

[0102] (transparency) The obtained OPP printed materials were visually inspected and evaluated according to the following criteria. The results are shown in Tables 5 and 6. A score of "4" or "3" according to the evaluation criteria below indicates a level that is usable. (Transparency evaluation criteria) 4. The transparency is significantly higher than the reference printed material. (Excellent) 3. Higher transparency than the reference printed material. (Good) 2. Transparency equivalent to the standard printed material. (Poor) 1: The transparency is lower than the reference printed material. (Extremely poor)

[0103] (Glossy) The obtained OPP printed materials were visually inspected and evaluated according to the following criteria. The results are shown in Tables 5 and 6. A score of "4" or "3" according to the evaluation criteria below indicates a level that is usable. (Evaluation criteria for gloss) 4: The gloss is significantly higher than the reference print. (Excellent) 3: The gloss is greater than the reference print. (Good) 2. Glossiness equivalent to the reference printed material. (Defective) 1: The gloss level is lower than the reference print. (Extremely poor)

[0104] [Table 5]

[0105] [Table 6]

[0106] From the results in Tables 5 and 6 above, it can be seen that using the pigment composition of the present invention yields an ink with high clarity, transparency, and good viscosity stability. On the other hand, the specific surface area is 30 m² 2 When the content of compound (B) was changed from 3.25 mol% to 0.00 mol%, as in Comparative Example A-113 where it was less than / g, viscosity stability, clarity, and transparency were inferior compared to Example A-1. Also, the specific surface area was 30 m². 2 When the drying conditions were changed from A to C, as in Comparative Example A-101 (which was less than / g), the viscosity stability was equivalent to that of Example A-1, but the clarity and transparency were lacking.

Claims

1. A pigment composition comprising compound (A) represented by the following general formula (1) and compound (B) represented by the following general formula (2), The compound (A) and (B) together make up 100 mol% of the total, with 80-99 mol% of compound (A) and 1-20 mol% of compound (B), and having a specific surface area of ​​30 m² as measured by the BET method. ２ A pigment composition having a concentration of 1 / g or more. General formula (1) 【Chemistry 1】 (In the formula Ar １ , and Ar ２ This indicates an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. General formula (2) 【Chemistry 2】 (In the formula Ar ３ Ar represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. ４ (This refers to an aryl group having the same or different substituents selected from the group consisting of hydrogen atoms, sulfo groups, and sulfonates, excluding cases where all substituents are hydrogen.) (Ar １ Ar ２ , and Ar ３ They are either the same or different.

2. A coloring composition comprising the pigment composition and resin according to claim 1.

3. An ink comprising the pigment composition described in claim 1.

4. A printed article obtained by printing the ink described in claim 3.

5. A wet cake of a pigment composition containing the following pigment composition is dried by a continuous hot-air heating drying method to obtain a powder having a specific surface area of 30 m ２ / g or more, a method for producing a pigment composition. The pigment composition comprises compound (A) represented by the following general formula (1) and compound (B) represented by the following general formula (2), wherein compound (A) accounts for 80 to 99 mol% and compound (B) accounts for 1 to 20 mol% of the total 100 mol% of compound (A) and compound (B). General formula (1) 【Chemistry 12】 (In the formula Ar １ , and Ar ２ This indicates an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. General formula (2) 【Chemistry 13】 (In the formula Ar ３ Ar represents an aryl group having the same or different substituents selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogeno group. ４ (This refers to an aryl group having the same or different substituents selected from the group consisting of hydrogen atoms, sulfo groups, and sulfonates, excluding cases where all substituents are hydrogen.) (Ar １ Ar ２ , and Ar ３ They are either the same or different.

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