WO2023203789A1 - Procédé de production d'une composition de pigment de phtalocyanine de cuivre de forme epsilon - Google Patents

Procédé de production d'une composition de pigment de phtalocyanine de cuivre de forme epsilon Download PDF

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Publication number
WO2023203789A1
WO2023203789A1 PCT/JP2022/030850 JP2022030850W WO2023203789A1 WO 2023203789 A1 WO2023203789 A1 WO 2023203789A1 JP 2022030850 W JP2022030850 W JP 2022030850W WO 2023203789 A1 WO2023203789 A1 WO 2023203789A1
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Prior art keywords
copper phthalocyanine
pigment composition
type copper
producing
type
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PCT/JP2022/030850
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English (en)
Japanese (ja)
Inventor
成美 奥村
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大日精化工業株式会社
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Classifications

    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents of phthalocyanines
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a method for producing an ⁇ -type copper phthalocyanine pigment composition.
  • the ⁇ -type copper phthalocyanine pigment is a pigment with a reddish blue tone that is clear and has strong coloring power, and has excellent light resistance and heat resistance. Taking advantage of these properties, ⁇ -type copper phthalocyanine pigments are used in a wide range of fields such as paints and plastics, and are also useful as pigments for forming blue colors in color filters for liquid crystals.
  • ⁇ -type copper phthalocyanine As a general method for producing ⁇ -type copper phthalocyanine, a method is known in which ⁇ -type copper phthalocyanine is subjected to solvent salt milling together with a phthalocyanine derivative (Patent Document 1). Furthermore, phthalimidomethylated phthalocyanine and the like are known as phthalocyanine derivatives used in solvent salt milling (Patent Documents 1 and 2).
  • Patent Document 3 a method of phthalimidomethylating phthalocyanine in sulfuric acid is known (Patent Document 3).
  • xylene sulfonic acid which is an acidic surfactant, is added after the reaction is completed.
  • Patent No. 4097053 Japanese Patent Application Publication No. 2002-121420 US Patent No. 2,855,403
  • phthalimidomethylated copper phthalocyanine produced by reaction in concentrated sulfuric acid can be obtained in the form of a strongly aggregated powder. Since phthalimidomethylated copper phthalocyanine hardly dissolves in water-soluble organic solvents such as diethylene glycol used in solvent salt milling, it is difficult to uniformly mix it with ⁇ -type copper phthalocyanine even by solvent salt milling proposed in Patent Document 1. took a long time.
  • ⁇ -type copper phthalocyanine produced in sulfuric acid also has strong aggregation properties. Therefore, when strongly aggregated ⁇ -type copper phthalocyanine is subjected to solvent salt milling, it tends to undergo crystal transition from ⁇ -type to ⁇ -type in a non-uniform state. As a result, the resulting pigment particles tend to be non-uniform, resulting in problems such as decreased performance as a coloring material and a large amount of ⁇ -type particles mixed in. In particular, when used as a coloring agent for liquid crystal color filters, color properties such as brightness and contrast tend to be insufficient.
  • the present invention has been made in view of the problems of the prior art, and its object is to provide coloring for color filters used in liquid crystals, etc., which have excellent color characteristics such as contrast and brightness.
  • An object of the present invention is to provide a simple method for producing ⁇ -type copper phthalocyanine, which is useful as an agent.
  • the following method for producing an ⁇ -type copper phthalocyanine pigment composition is provided.
  • a method for producing an ⁇ -type copper phthalocyanine pigment composition comprising the step of solvent salt milling a mixture containing phthalocyanine to obtain a pigment composition.
  • ⁇ -type copper phthalocyanine which has excellent color properties such as contrast and brightness and is useful as a coloring agent for color filters used in liquid crystals and the like.
  • One embodiment of the method for producing the ⁇ -type copper phthalocyanine pigment composition of the present invention (hereinafter also simply referred to as "the production method") is to treat phthalimidomethylated copper phthalocyanine with a nonionic surfactant to form the treated phthalimide.
  • a step of obtaining methylated copper phthalocyanine (step (1)) and a step of solvent salt milling a mixture containing ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine, and treated phthalimidomethylated copper phthalocyanine to obtain a pigment composition. (Step (2)).
  • Step (1) A step of obtaining methylated copper phthalocyanine
  • step (2) a step of solvent salt milling a mixture containing ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine, and treated phthalimidomethylated copper phthalocyanine to obtain a pigment composition.
  • step (1) phthalimidomethylated copper phthalocyanine (hereinafter also referred to as "PIM copper phthalocyanine”) is treated with a nonionic surfactant to obtain treated PIM copper phthalocyanine.
  • PIM copper phthalocyanine phthalimidomethylated copper phthalocyanine
  • a nonionic surfactant By treating the PIMized copper phthalocyanine with a nonionic surfactant, the strong aggregation of the PIMized copper phthalocyanine can be alleviated, unlike the case where the PIMized copper phthalocyanine is treated with a surfactant other than the nonionic surfactant. This makes it possible to improve the processing efficiency of solvent salt milling in the subsequent step (step (2)), and to easily produce an ⁇ -type copper phthalocyanine pigment composition with excellent color properties such as contrast and brightness. I can do it.
  • PIMized copper phthalocyanine can be produced according to a known method using copper phthalocyanine as a raw material. For example, as disclosed in US Pat. No. 2,855,403, PIMized copper phthalocyanine can be obtained by reacting copper phthalocyanine and methylol phthalimide in sulfuric acid. Note that phthalimide and paraformaldehyde may be used instead of methylol phthalimide.
  • nonionic surfactant Commercially available products can be used as the nonionic surfactant.
  • specific examples of nonionic surfactants include glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, sucrose fatty acid ester, fatty acid alkanolamide, polyoxyalkylene alkyl ether, polyoxyalkylene alkylphenyl ether, and polyoxyalkylene fatty acid ester.
  • Oxyalkylene polystyrylphenyl ether and the like can be mentioned.
  • polyoxyalkylene alkyl ether polyoxyalkylene alkylphenyl ether, and polyoxyalkylene polystyrylphenyl ether are preferred, and polyoxyalkylene polystyrylphenyl ether is particularly preferred.
  • the process for producing PIM copper phthalocyanine includes, for example, a reaction process in concentrated sulfuric acid, a precipitation process in water, a filtration/washing process, and a drying process. Among these, it is preferable to treat the PIM copper phthalocyanine with a nonionic surfactant after the filtration/washing process and before the drying process.
  • Specific methods for treating PIMized copper phthalocyanine with a nonionic surfactant include, for example, (i) a method of adding a nonionic surfactant into the system in the production process of PIMized copper phthalocyanine; ii) A method of adding an aqueous solution of a nonionic surfactant into the system; (iii) A method of adding an emulsion obtained by mixing a nonionic surfactant, a water-insoluble solvent, and water into the system; etc. can be mentioned.
  • the above emulsion is added to a slurry prepared by peptizing PIMized copper phthalocyanine in water, and the emulsion is brought into contact with the PIMized copper phthalocyanine (contact with a nonionic surfactant).
  • PIMized copper phthalocyanine in the slurry forms strong aggregates.
  • water-insoluble organic solvent it is preferable to use at least one selected from the group consisting of toluene, xylene, ethyl acetate, and butyl acetate, and it is particularly preferable to use xylene.
  • the treatment of PIMized copper phthalocyanine with a nonionic surfactant is preferably carried out under heating conditions.
  • the uniformity of the treatment can be further improved by bringing the PIMized copper phthalocyanine into contact with a nonionic surfactant under heating conditions.
  • the temperature during treatment is preferably 60 to 100°C, more preferably 80 to 90°C.
  • Step (2) a mixture containing ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine, and treated PIMized copper phthalocyanine is subjected to solvent salt milling to obtain a pigment composition.
  • the treated PIMized copper phthalocyanine is PIMized copper phthalocyanine that has been treated with a nonionic surfactant in the above-mentioned step (1), so that strong aggregation is alleviated. Therefore, by subjecting the mixture containing this treated PIMized copper phthalocyanine to solvent salt milling, the crystal transition from ⁇ type to ⁇ type is promoted, resulting in an ⁇ type copper phthalocyanine pigment composition with excellent color properties such as contrast and brightness. can be manufactured more efficiently.
  • Solvent salt milling usually involves kneading a mixture containing ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine, and treated PIMized copper phthalocyanine using a kneader in the presence of a water-soluble organic solvent and an inorganic salt. and by grinding.
  • kneading machines include kneaders, planetary mixers, and Miracle K. C. K (trade name, manufactured by Asada Steel Co., Ltd.), Trimix (trade name, manufactured by Inoue Seisakusho Co., Ltd.), etc. can be used.
  • ⁇ -type copper phthalocyanine can be produced according to a known method using crude copper phthalocyanine containing ⁇ -type copper phthalocyanine.
  • methods for producing ⁇ -type copper phthalocyanine include (i) an acid pasting method in which crude copper phthalocyanine is dissolved in sulfuric acid and a sulfuric acid solution is injected into water to precipitate; (ii) using a ball mill, etc.
  • Examples include a dry milling method in which crude copper phthalocyanine is dry-milled; (iii) a solvent salt milling method in which crude copper phthalocyanine is kneaded with an inorganic salt and a water-soluble organic solvent in a kneader such as a kneader; and the like.
  • (i) acid pasting method is preferred because it yields a more highly purified and fine ⁇ -type copper phthalocyanine.
  • the concentration of sulfuric acid used in the acid pasting method is preferably 70 to 100% by mass. If the concentration of sulfuric acid is less than 70% by mass, crude copper phthalocyanine may be difficult to dissolve sufficiently, and ⁇ -type copper phthalocyanine may be easily mixed into the resulting precipitate. Furthermore, since the particle size of the obtained ⁇ -type copper phthalocyanine tends to increase, the subsequent solvent salt milling may also result in slightly insufficient refinement. On the other hand, if the concentration of sulfuric acid is too high, a portion of the ⁇ -type copper phthalocyanine produced may be easily sulfonated. Therefore, in consideration of the purity, particle size, etc. of the obtained ⁇ -type copper phthalocyanine, it is more preferable that the concentration of sulfuric acid used in the acid pasting method is 95 to 98% by mass.
  • ⁇ -type copper phthalocyanine one produced according to a known method may be used, or a commercially available product may be used.
  • Known methods for producing ⁇ -type copper phthalocyanine include the solvent method disclosed in Japanese Patent Publication No. 57-35210; the method of dry grinding followed by solvent treatment disclosed in Japanese Patent No. 3030880; and the method disclosed in Japanese Patent Publication No. 64-7108. Examples include a method of micronizing ⁇ -type copper phthalocyanine obtained by the disclosed copper phthalocyanine synthesis using solvent salt milling.
  • water-soluble organic solvent it is preferable to use a high boiling point solvent from the viewpoints of safety and workability.
  • water-soluble organic solvents include diethylene glycol, glycerin, propylene glycol, liquid polyethylene glycol, liquid polypropylene glycol, 2-methoxyethanol, 2-butoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene Examples include glycol, triethylene glycol monomethyl ether, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, and dipropylene glycol monoethyl ether.
  • the inorganic salt it is preferable to use a water-soluble inorganic salt.
  • the inorganic salt it is preferable to use sodium chloride, potassium chloride, sodium sulfate, magnesium sulfate, and the like.
  • Solvent salt milling is preferably carried out at 50 to 150°C, more preferably 70 to 140°C.
  • solvent salt milling is carried out under a temperature condition of less than 50° C.
  • the crystal transition from ⁇ type to ⁇ type may be somewhat insufficient.
  • solvent salt milling is performed under a temperature condition of over 150° C., the performance as a coloring material may tend to deteriorate slightly due to crystal growth.
  • Solvent salt milling is preferably carried out at 50 to 80°C.
  • the amount of ⁇ -type copper phthalocyanine relative to 100 parts by mass of ⁇ -type copper phthalocyanine is preferably 5 to 50 parts by mass, more preferably 10 to 30 parts by mass. If the amount of ⁇ -type copper phthalocyanine is less than 5 parts by mass per 100 parts by mass of ⁇ -type copper phthalocyanine, it may take some time for crystal transition from ⁇ -type to ⁇ -type, and ⁇ -type crystals may be formed. It may become easier. On the other hand, if the amount of the ⁇ -type copper phthalocyanine is more than 50 parts by mass based on 100 parts by mass of the ⁇ -type copper phthalocyanine, the productivity may decrease slightly, which may be industrially disadvantageous.
  • the amount of the water-soluble organic solvent is preferably 50 to 500 parts by mass with respect to a total of 100 parts by mass of ⁇ -type copper phthalocyanine and ⁇ -type copper phthalocyanine.
  • the water-soluble organic solvent may be added in its entirety at the initial stage of solvent salt milling, or may be added in stages depending on the progress of refinement.
  • the amount of the inorganic salt is preferably 200 to 2,000 parts by mass based on a total of 100 parts by mass of the ⁇ -type copper phthalocyanine and the ⁇ -type copper phthalocyanine, and the amount of the inorganic salt is preferably 200 to 2,000 parts by mass. It may be adjusted as appropriate depending on the degree. The larger the amount of the inorganic salt added, the finer the ⁇ -type copper phthalocyanine pigment composition can be obtained.
  • the amount of treated PIM copper phthalocyanine is preferably 1 to 20 parts by mass relative to 100 parts by mass of ⁇ -type copper phthalocyanine.
  • the treated PIMized copper phthalocyanine may be charged at the initial stage of solvent salt milling, or may be charged in advance during the process of producing ⁇ -type copper phthalocyanine. From the viewpoint of processing PIM copper phthalocyanine more uniformly, it is possible to dissolve the treated PIM copper phthalocyanine in sulfuric acid together with the crude copper phthalocyanine used as a raw material when producing ⁇ -type copper phthalocyanine by the acid pasting method described above. preferable.
  • the time required for solvent salt milling varies depending on the temperature, the amount of materials charged, etc., but is preferably 2 to 20 hours, and may be adjusted taking into account the progress of crystal transition and refinement.
  • a powdered pigment composition that can be used as a coloring material can be obtained by peptizing the kneaded material obtained by solvent salt milling in water, followed by filtration, washing, drying, and pulverization. It is preferable to repeat filtration and water washing until the water-soluble organic solvent and inorganic salt contained in the kneaded product are completely removed.
  • the drying temperature may be, for example, 70 to 120° C., and a box dryer, band dryer, spray dryer, etc. can be used.
  • a mortar, hammer mill, disc mill, pin mill, jet mill, etc. can be used to crush the dried lumps into powder.
  • Step (3) The pigment composition obtained by the solvent salt milling described above can be used as the desired ⁇ -type copper phthalocyanine pigment composition.
  • the manufacturing method of the present embodiment further includes a step (step (3)) of subjecting the pigment composition obtained in step (2) above to solvent salt milling again.
  • solvent salt milling is preferably carried out at 50 to 80°C, more preferably solvent salt milling is carried out at 50 to 70°C.
  • the obtained ⁇ -type copper phthalocyanine pigment composition may be treated with pigment derivatives such as various phthalocyanine derivatives depending on the purpose.
  • pigment derivatives include sulfonic acid derivatives of metal-free or metal phthalocyanines, N-(dialkylamino)methyl derivatives of metal-free or metal phthalocyanines, N-(dialkylaminoalkyl)sulfonic acid amide derivatives of metal-free or metal phthalocyanines, etc. be able to.
  • the pigment derivative may be added during the manufacturing process of the ⁇ -type copper phthalocyanine pigment composition, or may be added to the obtained ⁇ -type copper phthalocyanine pigment composition. Among these, it is preferable to add a pigment derivative when peptizing the wet cake obtained after solvent salt milling in water. When adding the pigment derivative, an acid or alkali may be added to adjust the pH, if necessary.
  • the ⁇ -type copper phthalocyanine pigment composition it may be treated with a pigment dispersant.
  • a pigment dispersant a commercially available product can be used.
  • Commercially available pigment dispersants include the following trade names: DISPERBYK-130, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-170, DISPERBYK-171, DISPERBYK-174, DISPERBY K-180, DISPERBYK-182, DISPERBYK-183, DISPERBYK-184, DISPERBYK-185, DISPERBYK-2000, DISPERBYK-2001, DISPERBYK-2022, DISPERBYK-2050, DISPERBYK-2055, DISP ERBYK-2059, DISPERBYK-2070, DISPERBYK-2151, DISPERBYK-2064 (and above, BYK); EF
  • the process of producing the ⁇ -type copper phthalocyanine pigment composition it may be treated with various resins.
  • resins include acrylic resins; urethane resins; alkyd resins; natural rosins such as wood rosin, gum rosin, and tall oil rosin; modified rosins such as polymerized rosin, disproportionated rosin, hydrogenated rosin, oxidized rosin, and maleated rosin. and rosin derivatives such as rosin amine, lime rosin, alkylene oxide-added rosin, rosin-modified alkyd resin, and rosin-modified phenol.
  • pigment dispersants that are water-soluble or can be uniformly dispersed in water may be treated in the same manner as for the pigment derivatives described above.
  • Pigment dispersants and the like that can be dissolved in organic solvents may be added during solvent salt milling.
  • An emulsion was prepared by mixing 10 parts of xylene, 1 part of polyoxyalkylene polystyrylphenyl ether, and 50 parts of water using a disper. The prepared emulsion was added to the slurry and stirred at 90°C for 1 hour. After cooling to 60° C., the mixture was filtered, dried, and pulverized to obtain 100 parts of PIM copper phthalocyanine. The obtained PIMized copper phthalocyanine is a treated PIMized copper phthalocyanine treated with a nonionic surfactant.
  • Example 1 ⁇ Production of ⁇ -type copper phthalocyanine pigment composition> (Example 1) 58 parts of crude copper phthalocyanine (including ⁇ -type copper phthalocyanine) produced by a conventional method and 3 parts of the treated PIM copper phthalocyanine obtained in Production Example 1 were added to 400 parts of 98% sulfuric acid, and the mixture was heated at 80°C for 3 hours. A sulfuric acid solution was obtained by stirring. After pouring the obtained sulfuric acid solution into 8,000 parts of ice water, the generated precipitate was filtered, washed with water, dried, and crushed to obtain 58 parts of a co-precipitate of ⁇ -type copper phthalocyanine and PIMized copper phthalocyanine. Ta.
  • Example 2 9 parts of the ⁇ -type copper phthalocyanine pigment composition obtained in Example 1, 90 parts of pulverized salt obtained by pulverizing with a pulverizer, and 21 parts of diethylene glycol were placed in a kneader and kneaded at 60° C. for 18 hours. During the kneading, 0.5 part of diethylene glycol was added in several portions as needed to obtain an appropriate viscosity. After peptizing the obtained kneaded material in water, 98% sulfuric acid was added in an amount to give a sulfuric acid concentration of 2%, and the mixture was stirred at 90° C. for 1 hour to obtain a slurry. The obtained slurry was filtered, washed with water, dried, and crushed to obtain 10 parts of an ⁇ -type copper phthalocyanine pigment composition.
  • Comparative example 1 22 parts of an ⁇ -type copper phthalocyanine pigment composition was prepared in the same manner as in Example 1 above, except that the untreated PIM copper phthalocyanine obtained in Comparative Production Example 1 was used in place of the treated PIM copper phthalocyanine. I got it.
  • Example 2 The ⁇ -type copper phthalocyanine pigment composition obtained in Example 1 was replaced with the ⁇ -type copper phthalocyanine pigment composition obtained in Comparative Example 1 in the same manner as in Example 2 described above. 10 parts of a phthalocyanine pigment composition were obtained.
  • a CF coloring agent was applied to a glass plate using a spin coater. After prebaking at 90°C for 2 minutes, post-baking was performed at 230°C for 30 minutes to obtain a glass substrate for measurement.
  • ⁇ -type copper phthalocyanine composition of the present invention According to the method for producing an ⁇ -type copper phthalocyanine composition of the present invention, ⁇ -type copper phthalocyanine useful as a coloring agent for color filters used in liquid crystals and the like can be easily produced.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

L'invention concerne un procédé pratique de production de phtalocyanine de cuivre de forme epsilon qui présente d'excellentes caractéristiques de couleur, par exemple, un contraste et une brillance, et qui est utile, entre autres, comme colorant pour les filtres colorés utilisés avec, par exemple, des cristaux liquides. Le procédé de production d'une composition de pigment de phtalocyanine de cuivre de forme epsilon comprend : une étape de traitement d'une phtalocyanine de cuivre phtalimidométhylée avec un tensioactif non ionique pour obtenir une phtalocyanine de cuivre phtalimidométhylée traitée ; et une étape d'obtention d'une composition de pigment par le broyage de sels en solvant d'un mélange comprenant de la phtalocyanine de cuivre de forme alpha, de la phtalocyanine de cuivre de forme epsilon, et de la phtalocyanine de cuivre phtalimidométhylée traitée.
PCT/JP2022/030850 2022-04-20 2022-08-15 Procédé de production d'une composition de pigment de phtalocyanine de cuivre de forme epsilon WO2023203789A1 (fr)

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JP2022069175A JP7110511B1 (ja) 2022-04-20 2022-04-20 ε型銅フタロシアニン顔料組成物の製造方法
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JP2002121420A (ja) * 2000-08-07 2002-04-23 Dainippon Ink & Chem Inc 銅フタロシアニン顔料及びその製造方法
JP2007009007A (ja) * 2005-06-29 2007-01-18 Dainippon Ink & Chem Inc ε型銅フタロシアニン顔料組成物及びその製造方法
JP4097053B2 (ja) * 1999-03-08 2008-06-04 東洋インキ製造株式会社 カラーフィルタ用着色組成物の製造方法およびカラーフィルタの製造方法
JP2010244028A (ja) * 2009-03-17 2010-10-28 Fujifilm Corp 着色硬化性組成物、カラーフィルタ、及びカラーフィルタの製造方法
JP2012032833A (ja) * 2011-10-28 2012-02-16 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用着色組成物およびカラーフィルタ

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