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
  • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
  • C09B47/18—Obtaining compounds having oxygen atoms directly bound to the phthalocyanine skeleton
• • 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
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
  • C09B67/0035—Mixtures 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
  • C09B67/006—Preparation of organic 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
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
  • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
  • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
  • C09D11/32—Inkjet printing inks characterised by colouring agents
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
  • C09D11/32—Inkjet printing inks characterised by colouring agents
  • C09D11/322—Pigment inks

Definitions

• the present disclosure relates to a phthalocyanine pigment, a phthalocyanine compound, a coloring composition, a method for producing a phthalocyanine pigment, and a method for producing a coloring composition.
• coloring compositions contain various pigments, dyes, and the like.
• JP 2016-141792 A discloses a coloring composition containing C.I. Pigment Green 58 (hereinafter also referred to as "PG58"), which has a true density of 2.985 to 3.005, as a pigment.
• PG58 C.I. Pigment Green 58
• WO 2020/171139 A discloses a coloring composition that contains a dye instead of a pigment for the purpose of improving brightness.
• Pigments contained in coloring compositions are required to have various properties depending on their applications. For example, in recent years, they are required to be able to suppress color change caused by long-term exposure to sunlight or the like (hereinafter, also referred to as “lightfastness”). In addition, from the viewpoint of forming good images, etc., pigments are required to be able to suppress aggregation over time (hereinafter, also referred to as "aggregation suppression property"). For example, a pigment having excellent aggregation suppression property can improve the ejection stability when used in inkjet printing, etc., and as a result, the occurrence of blurring, etc., in images formed by inkjet printing can be suppressed.
• An object of one embodiment of the present disclosure is to provide a phthalocyanine pigment, a phthalocyanine compound, and a colored composition that are excellent in light fastness and aggregation inhibition properties.
• Another problem to be solved by another embodiment of the present disclosure is to provide a method for producing a phthalocyanine pigment having excellent light fastness and aggregation inhibition properties, and a method for producing a colored composition.
• a phthalocyanine pigment having at least one diffraction peak at 3° ⁇ 2 ⁇ 7° in a powder X-ray diffraction spectrum and represented by the following general formula (1):
• M represents zinc or copper;
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• M is zinc;
• the phthalocyanine pigment according to the above item ⁇ 1>, wherein at least one of R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 is a group represented by the following formula (2):
• R 201 , R 202 , R 203 , R 204 , and R 205 each independently represent a hydrogen atom, an alkyl group, a phenoxycarbonyl group, or an alkoxy group; at least one of R 201 , R 202 , R 203 , R 204 and R 205 is an alkyl group, a phenoxycarbonyl group or an alkoxy group; * indicates the connection to the oxygen atom.
• R 201 , R 202 , R 204 and R 205 are hydrogen atoms;
• R 201 , R 202 , R 204 and R 205 are hydrogen atoms;
• ⁇ 5> The phthalocyanine pigment according to any one of ⁇ 1> to ⁇ 4> above, having a solubility in acetone at 25° C. of less than 0.005% by mass.
• ⁇ 6> A phthalocyanine compound represented by the following general formula (3):
• M represents zinc or copper
• R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• at least one of R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 , and R 308 is an aryl group represented by the following formula (4).
• R 401 , R 402 , R 404 and R 405 are hydrogen atoms;
• R 403 represents a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, or a propyloxy group;
• * indicates the connection to the oxygen atom.
• the solvent includes at least one selected from the group consisting of alcohols, ketones, carboxylic acid esters, and ethers.
• the solvent contains a carboxylic acid ester.
• ⁇ 12> The coloring composition according to any one of the above ⁇ 7> to ⁇ 11>, further comprising a dispersant.
• ⁇ 13> The colored composition according to ⁇ 12> above, wherein the dispersant is a polymer dispersant having a weight average molecular weight of 1,000 to 100,000.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• a method for producing a colored composition comprising a mixing step of mixing at least one of the phthalocyanine pigment according to ⁇ 1> above and the phthalocyanine compound according to ⁇ 6> above with a solvent.
• ⁇ 17> The method for producing a colored composition according to ⁇ 16> above, wherein in the mixing step, at least one of the phthalocyanine pigment and the phthalocyanine compound is dispersed in the solvent.
• a phthalocyanine pigment, a phthalocyanine compound, and a colored composition that are excellent in light fastness and aggregation inhibition properties.
• a method for producing a phthalocyanine pigment having excellent light fastness and aggregation inhibition properties it is possible to provide a method for producing a colored composition.
• FIG. 1 is an X-ray diffraction spectrum obtained by subjecting the pigment G-1 produced in Example 1 to powder X-ray diffraction.
• the use of "to" indicating a range of numerical values means that the numerical values before and after it are included as the lower limit and upper limit.
• the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages.
• the upper or lower limit value of the numerical range may be replaced with a value shown in the examples.
• a "pigment” refers to a compound having a solubility of less than 0.01% by mass in acetone at 25° C. The solubility is preferably less than 0.005% by mass.
• a “dye” refers to a compound having a solubility in acetone at 25°C of 0.01% by mass or more.
• pigments and dyes have different crystallinity, and the degree of interaction between the compounds changes depending on the crystallinity, which results in a change in solubility in a solvent. In other words, even if compounds have the same structure, one can be classified as a pigment and the other as a dye due to the difference in crystallinity.
• one method for evaluating the crystallinity is to use powder X-ray diffraction spectrum.
• the phthalocyanine pigment of the present disclosure has at least one diffraction peak at 3° ⁇ 2 ⁇ 7° in a powder X-ray diffraction spectrum, and is represented by the following general formula (1).
• M represents zinc or copper, preferably zinc;
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• the phthalocyanine pigment of the present disclosure has at least one diffraction peak at 3° ⁇ 2 ⁇ 7° in a powder X-ray diffraction spectrum, but may have two or more diffraction peaks.
• the diffraction peak of the phthalocyanine pigment of the present disclosure can be adjusted by adjusting the ratio of the amount of the solvent to the amount of the phthalonitrile compound used in the production of the phthalocyanine pigment.
• the diffraction peak can also be adjusted by the type of the phthalonitrile compound used.
• diffraction peaks are observed as follows.
• X-ray diffraction is performed under the following conditions using the phthalocyanine pigment powder of the present disclosure, and the number of diffraction peaks at diffraction angles 2 ⁇ of 3° to 7° is confirmed.
• a known device can be used as the measurement device. Examples of X-ray devices that can be used include smartlab manufactured by Rigaku Corporation, D8 Discover and Malvern manufactured by Bruker, and Empyrean manufactured by Panalytical.
• Radiation source Cu Diffraction angle 2 ⁇ : 2° to 60° ⁇ step: 0.01°
• the phthalocyanine pigment of the present disclosure preferably has at least one diffraction peak at 3.8° ⁇ 2 ⁇ 6° in the powder X-ray diffraction spectrum.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, and examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, etc.
• the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched.
• aryl group examples include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 9-anthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 9-phenanthryl group, a 1-pyrenyl group, a 5-naphthacenyl group, a 1-indenyl group, a 2-azulenyl group, a 1-acenaphthyl group, a 2-fluorenyl group, a 9-fluorenyl group, a 3-perylenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2,3-xylyl group, a 2,5-xylyl group, a mesityl group, a p-cumenyl group, a p-dodecylpheny
• heterocyclic group examples include an imidazolyl group, a benzimidazolyl group, a pyrazolyl group, a benzopyrazolyl group, a triazolyl group, a thiazolyl group, a benzothiazolyl group, an isothiazolyl group, a benzoisothiazolyl group, an oxazolyl group, a benzoxazolyl group, a thiadiazolyl group, a pyrrolyl group, a benzopyrrolyl group, an indolyl group, an isoxazolyl group, a benzoisoxazolyl group, a thienyl group, a benzothienyl group, a furyl group, a benzofuryl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a pyridazinyl group, a pyrimidinyl group, a
• alkyl group, aryl group, or heterocyclic group has a substituent
• substituents include an alkyl group, a hetero group, an aryl group, a halogen atom, a phenoxycarbonyl group, a phenoxyalkyl group, an acetyl group, an alkoxy group, an amido group, a sulfoalkyl group, and a sulfonamide group.
• substituted or unsubstituted aryl groups are preferred, and substituted aryl groups are more preferred.
• the substituents of the substituted aryl groups are preferably alkyl groups, phenoxycarbonyl groups, halogen atoms, alkoxycarbonyl groups, phenyl groups, or alkoxy groups, more preferably alkyl groups, phenoxycarbonyl groups, or alkoxy groups, even more preferably alkyl groups or alkoxy groups, and particularly preferably alkyl groups having 1 to 6 carbon atoms, or alkoxy groups having 1 to 6 carbon atoms.
• R 201 , R 202 , R 203 , R 204 , and R 205 each independently represent a hydrogen atom or a monovalent substituent, and * represents a linkage to an oxygen atom.
• the monovalent substituent include a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.
• R 201 , R 202 , R 203 , R 204 , and R 205 each independently represent any one selected from a hydrogen atom, a halogen atom, a phenyl group, an alkyl group, a phenoxycarbonyl group, and an alkoxy group, and at least one of R 201 , R 202 , R 203 , R 204 , and R 205 is an alkyl group, a phenoxycarbonyl group, or an alkoxy group, and more preferably an alkyl group or an alkoxy group.
• R 201 , R 202 , R 204 and R 205 are hydrogen atoms
• R 203 represents a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group or a propyloxy group.
• phthalocyanine pigment of the present disclosure is shown below. Note that the phthalocyanine pigment of the present disclosure is not limited to the following compound. Note that in the chemical formula in the present disclosure, Me means a methyl group, and Ph means a phenyl group.
• phthalocyanine compounds The phthalocyanine compound of the present disclosure is represented by the following general formula (3).
• M represents zinc or copper, preferably zinc;
• R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• at least one of R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 , and R 308 is an aryl group represented by the following formula (4).
• the alkyl group, aryl group and heterocyclic group are the same as those in the phthalocyanine pigment of the present disclosure, and therefore description thereof will be omitted here.
• R 401 , R 402 , R 404 and R 405 are hydrogen atoms;
• R 403 represents a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, or a propyloxy group, and * represents a linkage to the oxygen atom.
• the propyl group, butyl group and propyloxy group may be linear or branched.
• the phthalocyanine compound of the present disclosure has excellent light resistance and aggregation inhibition properties. The reason why the above effects are exhibited is not clear, but is presumed to be as follows.
• the phthalocyanine compound of the present disclosure has a specific structure, which is believed to increase the lattice spacing d of the crystals and reduce the tendency for pigment particles to aggregate.
• the phthalocyanine compound has a group represented by formula (4) having R 403 representing a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, or a propyloxy group, which effectively acts to dissipate light energy while appropriately relaxing the association and aggregation state of the phthalocyanine compound, thereby improving the light fastness.
• R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 , and R 308 are aryl groups represented by the above formula (4).
• the solubility of the phthalocyanine compound of the present disclosure in acetone at 25°C is preferably less than 0.01% by mass, and more preferably less than 0.005% by mass.
• Examples of the phthalocyanine compound of the present disclosure include compounds (2) to (5) exemplified above as the phthalocyanine pigment. Note that the phthalocyanine compound of the present disclosure is not limited to these compounds.
• the coloring composition of the present disclosure contains at least one of the phthalocyanine pigment and the phthalocyanine compound.
• the viscosity of the colored composition of the present disclosure at 25°C is preferably 1.0 MPa ⁇ s to 15.0 MPa ⁇ s, more preferably 2.0 MPa ⁇ s to 10.0 MPa ⁇ s, and even more preferably 3.0 MPa ⁇ s to 8.0 MPa ⁇ s.
• the viscosity is measured by a viscometer, for example, a viscometer RE85L (rotor: 1°34′ ⁇ R24, measurement range 0.6 to 1200 mPa ⁇ s) manufactured by Toki Sangyo Co., Ltd. can be used.
• the coloring composition of the present disclosure may contain a plurality of types of the phthalocyanine pigment and the phthalocyanine compound.
• the coloring composition may contain one or more types of the phthalocyanine pigment and the phthalocyanine compound, may contain a plurality of types of phthalocyanine pigments having mutually different structures, or may contain a plurality of types of phthalocyanine compounds having mutually different structures.
• the sum of the contents of the phthalocyanine pigment and the phthalocyanine compound relative to the total mass of the coloring composition is preferably 0.5% by mass to 10% by mass, more preferably 1% by mass to 8% by mass, and even more preferably 3% by mass to 6% by mass.
• the colored composition of the present disclosure preferably contains a solvent having a boiling point of less than 160° C. at 1013.2 hPa (hereinafter also referred to as a “specific solvent”).
• the boiling point is preferably 60° C. to 158° C., more preferably 80° C. to 150° C.
• the boiling point is a value measured by a boiling point meter, and can be measured using, for example, DosaTherm 300 manufactured by Titan Technologies, Inc.
• Examples of the specific solvent include methyl alcohol, ethyl alcohol, butyl alcohol, isobutyl alcohol, tert-butyl alcohol, propyl alcohol, isopropyl alcohol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, diethyl ether, dipropyl ether, tetrahydrofuran, dioxane, and ethylene glycol methyl ether.
• the coloring composition of the present disclosure may contain a solvent other than the specific solvent (hereinafter, also referred to as "other solvent”).
• the solvent may include at least one selected from water, alcohol, ketone, carboxylic acid ester, and ether.
• alcohols include methyl alcohol, ethyl alcohol, butyl alcohol, isobutyl alcohol, tert-butyl alcohol, propyl alcohol, isopropyl alcohol, 1-methoxy-2-propanol, benzyl alcohol, 1,2-hexanediol, glycerin, fluorinated alcohol, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, propylene glycol, butylene glycol, 1,2,6-hexanetriol, thioglycol, hexylene glycol, trimethylolethane, and trimethylolpropane.
• Examples of the ketone include acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
• Examples of the carboxylate include propylene glycol monomethyl ether acetate, ethyl 3-ethoxypropionate, methyl acetate, ethyl acetate, propyl acetate, methyl propionate, and ethyl propionate.
• the ether examples include diethyl ether, dipropyl ether, tetrahydrofuran, dioxane, ethylene glycol methyl ether, ethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, triethylene glycol monomethyl ether, and triethylene glycol monoethyl ether.
• the solvent preferably contains at least one selected from alcohol, ketone, and carboxylate, and more preferably contains a carboxylate.
• the coloring composition of the present disclosure may contain only one type of solvent, or may contain multiple types of solvents.
• the content of the solvent relative to the total mass of the coloring composition is preferably adjusted appropriately depending on the application of the coloring composition, and can be, for example, 1% by mass to 50% by mass. From the viewpoint of aggregation suppression, the content of the specific solvent relative to the total mass of the solvents contained in the colored composition of the present disclosure is preferably 50 to 100 mass%, and more preferably 80 to 100 mass%.
• the coloring composition of the present disclosure preferably does not contain an amide solvent, or contains an amide solvent, and the content of the amide solvent relative to the total mass of the coloring composition is 10 mass% or less, more preferably does not contain an amide solvent, or contains an amide solvent, and the content of the amide solvent relative to the total mass of the coloring composition is 5 mass% or less, even more preferably does not contain an amide solvent, or contains an amide solvent, and the content of the amide solvent relative to the total mass of the coloring composition is 3 mass% or less, particularly preferably does not contain an amide solvent, or contains an amide solvent, and the content of the amide solvent relative to the total mass of the coloring composition is 1 mass% or less, and most preferably does not contain an amide solvent.
• an amide solvent means a solvent having an amide bond
• examples thereof include dimethylformaldehyde, diethylformaldehyde, dimethylacetamide, diethylacetamide, N-methylpyrrolidone, 3-methoxy-N,N-dimethylpropanamide, hexamethylphosphoric triamide, and 1,3-dimethyl-2-imidazolidinone.
• compounds having an amide bond such as yellow dyes, are not solvents and are therefore not included in the amide solvents in the present disclosure.
• the colored composition of the present disclosure preferably contains a dispersant.
• the type of dispersant is not particularly important as long as it can disperse the pigment in the coloring composition and maintain that state stably.
• cationic, anionic, nonionic, amphoteric, etc. dispersants can be used.
• the dispersant is preferably a polymer dispersant.
• a polymer dispersant means a dispersant with a weight average molecular weight of 500 or more.
• Dispersants include modified acrylic copolymers, acrylic copolymers, polyurethanes, polyesters, alkyl ammonium salts or phosphate ester salts of polymeric copolymers, cationic comb-type graft polymers, etc.
• the weight average molecular weight of the dispersant is preferably from 1,000 to 100,000, more preferably from 5,000 to 50,000, and even more preferably from 10,000 to 45,000.
• GPC gel permeation chromatography
• the content of the dispersant relative to the total mass of the coloring composition is preferably 1% by mass to 20% by mass, more preferably 5% by mass to 15% by mass, and even more preferably 8% by mass to 13% by mass.
• the coloring composition of the present disclosure may contain a resin.
• the resin include acrylic resin, styrene-(meth)acrylic resin, vinyl resin, polyurethane, polyester, polyamide, and fluororesin.
• acrylic resins include homopolymers of monomers selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid esters, (meth)acrylamide, and (meth)acrylonitrile, and copolymers obtained by using two or more of these monomers.
• the acrylic resin may have a functional group selected from the group consisting of a methylol group, a hydroxyl group, a carboxyl group, and an amino group.
• Vinyl resins include polyvinyl alcohol, acid-modified polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, polyvinyl methyl ether, polyolefin, ethylene/butadiene copolymer, polyvinyl acetate, vinyl chloride/vinyl acetate copolymer, vinyl chloride/(meth)acrylic acid ester copolymer, ethylene/vinyl acetate copolymer, etc.
• Polyurethanes include compounds obtained by reacting at least one selected from the group consisting of polyols (e.g., ethylene glycol, propylene glycol, glycerin, trimethylolpropane, etc.), polyester polyols, polyether polyols (e.g., poly(oxypropylene ether) polyols, poly(oxyethylene-propylene ether) polyols, etc.), and polycarbonate polyols with polyisocyanates.
• polyols e.g., ethylene glycol, propylene glycol, glycerin, trimethylolpropane, etc.
• polyester polyols e.g., polyether polyols (e.g., poly(oxypropylene ether) polyols, poly(oxyethylene-propylene ether) polyols, etc.)
• polyether polyols e.g., poly(oxypropylene ether) polyols, poly(oxyethylene
• Polyesters include compounds obtained by reacting polyols (e.g., ethylene glycol, propylene glycol, glycerin, trimethylolpropane, etc.) with polybasic acids.
• polyols e.g., ethylene glycol, propylene glycol, glycerin, trimethylolpropane, etc.
• the resin content relative to the total mass of the coloring composition is preferably 0.5% by mass to 20% by mass, more preferably 1% by mass to 15% by mass, and even more preferably 3% by mass to 10% by mass.
• the coloring composition of the present disclosure may contain components (hereinafter also referred to as "additives”) other than the above-mentioned components.
• additives include surfactants, colloidal silica, inorganic salts, solid wetting agents (such as urea), discoloration inhibitors, emulsion stabilizers, penetration enhancers, UV absorbers, preservatives, antifungal agents, pH adjusters, antifoaming agents, viscosity adjusters, dispersion stabilizers, rust inhibitors, chelating agents, and water-soluble polymer compounds.
• the coloring composition of the present disclosure can be used as an inkjet ink.
• the phthalocyanine pigment and the phthalocyanine compound contained in the coloring composition of the present disclosure have excellent aggregation suppression properties, and therefore can improve the ejection stability, so that the coloring composition of the present disclosure can be suitably used as an inkjet ink.
• the use of the coloring composition is not limited thereto, and it can be used in thermal transfer recording sheets, printing inks other than inkjet inks, paints, etc.
• the method for producing a phthalocyanine pigment according to the present disclosure includes a mixing step of mixing a phthalonitrile compound represented by any one of the following general formulas (5) to (8), a metal salt of at least one of zinc and copper, and a solvent.
• the ratio of the amount of the solvent used to the amount of the phthalonitrile compound used is set to 2.0 times or less on a mass basis.
• R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
• Preferred embodiments of R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 are the same as those of the phthalocyanine pigment of the present disclosure described above, and therefore description thereof will be omitted here.
• the phthalonitrile compounds represented by the general formulas (5) to (8) may be different compounds or the same compound.
• the phthalonitrile compounds represented by the above general formulas (5) to (8) used in the method for producing the phthalocyanine pigment of the present disclosure are preferably the same compounds.
• a phthalocyanine pigment having excellent light resistance and aggregation suppression properties can be produced.
• the reason why the above effects are exhibited is not clear, but is presumed to be as follows.
• the ratio of the amount of the solvent used to the amount of the phthalonitrile compound used in the mixing step is set to 2.0 times or less on a mass basis.
• the above-mentioned phthalocyanine pigment of the present disclosure can be produced.
• the above-mentioned phthalocyanine compound of the present disclosure can also be produced.
• solvents used in the synthesis of phthalocyanine pigments include benzonitrile, nitrobenzene, chlorobenzene, dichlorobenzene, trichlorobenzene, chloronaphthalene, methylnaphthalene, pyridine, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and sulfolane.
• the ratio of the amount of the solvent used to the amount of the phthalonitrile compound used is preferably 1.0 to 2.0 times, more preferably 1.2 to 2.0 times, and even more preferably 1.5 to 1.9 times, on a mass basis.
• the method for producing the phthalocyanine pigment of the present disclosure is preferably carried out under an inert atmosphere.
• Examples of zinc metal salts include zinc iodide, zinc chloride, zinc bromide, zinc acetate, zinc stearate, etc.
• Examples of copper metal salts include copper iodide, copper chloride, copper bromide, copper acetate, copper stearate, etc. Among the above, zinc metal salts are preferred, and zinc iodide is more preferred.
• the ratio of the sum of the amounts of zinc and copper metal salts used to the amount of phthalonitrile compound used is preferably 0.01 to 0.6 times, more preferably 0.05 to 0.5 times, and even more preferably 0.1 to 0.4 times, by mass.
• the method for producing the phthalocyanine pigment of the present disclosure may include a heating step of heating the mixture obtained in the mixing step to precipitate crystals of the phthalocyanine pigment.
• the heating method is not particularly limited, and the heating can be performed by using a heating device (heater, etc.).
• the heating temperature is preferably 100° C. to 250° C., and more preferably 130° C. to 200° C.
• the heating temperature refers to the environmental temperature at which the mixture is heated.
• the heating time is, for example, preferably 3 hours to 12 hours, and more preferably 4 hours to 8 hours.
• the method for producing the phthalocyanine pigment of the present disclosure may include a cooling step of performing cooling after the heating step.
• the cooling method is not particularly limited, and may be performed using a cooling device (such as a blower) or may be allowed to cool naturally.
• the cooling temperature is not particularly limited and can be, for example, 0° C. to 30° C. In the present disclosure, the cooling temperature refers to the environmental temperature at which cooling is performed. After cooling, filtration or the like may be carried out.
• the method for producing the phthalocyanine pigment of the present disclosure may include a milling step in order to microparticulate the above-described phthalocyanine pigment of the present disclosure.
• the above-described phthalocyanine pigment of the present disclosure may be subjected to a milling process to obtain a uniform particle size.
• the milling step is not particularly limited, but preferably includes a salt milling step in which milling is performed using a salt.
• the milling method may be a wet method or a dry method, but is preferably a wet method, and more preferably includes a solvent salt milling step in which milling is performed using a salt and a solvent.
• the solvent salt milling process can be carried out in accordance with the method described in paragraph 0064 of JP 2013-173883 A.
• 1 part by mass of the phthalocyanine pigment of the present disclosure 10 parts by mass of pulverized sodium chloride, and 2 parts by mass of diethylene glycol are charged into a twin-arm kneader and kneaded at 100° C. for 3 hours, and the kneaded mixture is taken out into 100 parts by mass of water at 80° C., filtered, and washed to obtain a finely divided green phthalocyanine pigment.
• a method for producing a colored composition of the present disclosure includes a mixing step of mixing at least one of the phthalocyanine pigment of the present disclosure described above and the phthalocyanine compound of the present disclosure described above with a solvent.
• phthalocyanine pigment phthalocyanine compound, and solvent of the present disclosure have been described above, so description thereof will be omitted here.
• the mixing method is not particularly limited as long as at least one of the phthalocyanine pigment of the present disclosure and the phthalocyanine compound of the present disclosure is mixed with a solvent.
• the mixing step in addition to the above-mentioned components, the above-mentioned dispersant, the above-mentioned resin, the above-mentioned additives, etc. may be added.
• the mixing step preferably includes a step of dispersing at least one of the phthalocyanine pigment of the present disclosure described above and the phthalocyanine compound of the present disclosure described above. The dispersion can be carried out in accordance with the method described in paragraph 0093 of JP-A-2013-173883.
• At least one of the phthalocyanine pigment of the present disclosure and the phthalocyanine compound of the present disclosure can be dispersed in a solvent using a dispersing device.
• a dispersing device a device using a stirrer stirring method, an impeller stirring method, an in-line stirring method, a mill method (e.g., a colloid mill, a ball mill, a sand mill, a bead mill, an attritor, a roll mill, a jet mill, a paint shaker, an agitator mill, etc.), an ultrasonic method, a high-pressure emulsification dispersion method (high-pressure homogenizer; specific commercially available devices include a Gaulin homogenizer, a microfluidizer, and a DeBEE2000, etc.) can be used.
• high-pressure homogenizer specific commercially available devices include a Gaulin homogenizer, a microfluidizer, and a DeBEE2000, etc.
• Example 1 Zinc iodide (1.74 g), 3,6-difluoro-4,5-bisphenoxyphthalonitrile (6.20 g), and benzonitrile (12 mL) were placed in a 100 mL recovery flask and mixed (mixing step), and reacted at 160° C. for 5 hours under a nitrogen atmosphere to precipitate crystals (heating step). The inside of the recovery flask was cooled to room temperature (25° C.) (cooling step), and the precipitated crystals were collected by filtration. The obtained crystals were washed with 60 mL of methanol to obtain Pigment G-1 (green pigment). The yield was 2.64 g, the yield rate was 41%, and the solubility in acetone at 25° C.
• Pigment G-1 was identified as the following compound by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) (MALDI-TOFMS: 1459 ([M+1] + )). In the production of pigment G-1, the ratio of the amount of the solvent used to the amount of the phthalonitrile compound used was 1.9 times on a mass basis.
• Pigment G-1 was subjected to powder X-ray diffraction under the following conditions to confirm the number of diffraction peaks at angles of 3° to 7°.
• the diffraction angles at which peaks were observed are shown in Table 1.
• Z maximum peak intensity in the obtained X-ray diffraction spectrum
• a peak having an intensity of 1 ⁇ 4 Z or more was recognized as a diffraction peak.
• Fig. 1 shows the X-ray diffraction spectrum obtained by subjecting Pigment G-1 to powder X-ray diffraction.
• pigment G-1 40 parts by weight of pigment G-1, 23 parts by weight of acrylic resin (dispersant, average molecular weight 23,000) synthesized with reference to [Synthesis Example 1] described in JP2016-141792A (dispersant), 34 parts by weight of 5% by weight aqueous sodium hydroxide solution, 7 parts by weight of isopropyl alcohol, and 75 parts by weight of ion-exchanged water were charged into a stainless steel container. Next, the mixture was dispersed for 2 hours with a paint conditioner using zirconia beads with a diameter of 0.5 mm manufactured by Nikkato Corporation to obtain pigment dispersion liquid 1 (mixing process).
• Example 2 Tetrafluorophthalonitrile (20.0 g), potassium fluoride (13.9 g), and acetone (72 mL) were placed in a three-neck flask and dissolved with stirring at 25°C. The mixture was then cooled, and a solution of p-cresol (21.6 g) in 48 mL of acetone was added dropwise at an internal temperature of -11°C to -5°C, after which the temperature was gradually increased to 25°C while stirring was continued for 5 hours. The insoluble matter in the reaction solution was filtered off, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography to obtain Intermediate G-2a. The yield was 37.6 g, 48%. Intermediate G-2a was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 377 ([M+1] + )).
• Pigment G-2 (green pigment) was obtained in the same manner as in Example 1, except that 3,6-difluoro-4,5-bisphenoxyphthalonitrile was replaced with Intermediate G-2a (15.0 g). The yield was 10.3 g, the yield rate was 66%, and the solubility in acetone at 25° C. was less than 0.005% by mass, confirming that the product was a pigment rather than a dye.
• Pigment G-2 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 1572 ([M+1] + )). In the production of pigment G-2, the ratio of the amount of the solvent used to the amount of the phthalonitrile compound used was 1.8 times on a mass basis.
• Pigment G-2 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 2 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-2.
• Example 3 The same procedure was repeated except that p-cresol in the synthesis of intermediate G-2a in Example 2 was changed to p-ethylphenol (19.2 g), to obtain 14.6 g of intermediate G-3a (yield 46%).
• Intermediate G-3a was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 405 ([M+1] + )).
• Pigment G-3 (green pigment) was obtained in the same manner as in Example 1, except that 3,6-difluoro-4,5-bisphenoxyphthalonitrile was replaced with Intermediate G-3a (10.0 g). The yield was 7.78 g, the yield rate was 75%, and the solubility in acetone at 25° C. was less than 0.005% by mass, confirming that the product was a pigment, not a dye.
• Pigment G-3 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 1684 ([M+1] + )). In the production of pigment G-3, the ratio of the amount of the solvent to the amount of the phthalonitrile compound was 1.8 times on a mass basis.
• Pigment G-3 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 3 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-3.
• Example 4 Pigment G-4 (green pigment) was obtained in the same manner as in Example 1, except that the 3,6-difluoro-4,5-bisphenoxyphthalonitrile in Example 1 was changed to 3,6-difluoro-4,5-bis[4-(1,1 dimethylethyl)phenoxy]phthalonitrile (12.0 g).
• the yield was 8.00 g, the yield rate was 65%, and the solubility in acetone at 25° C. was less than 0.005% by mass, confirming that the product was a pigment rather than a dye.
• Pigment G-4 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 1908 ([M+1] + )). In the production of pigment G-4, the ratio of the amount of the solvent to the amount of the phthalonitrile compound was 1.9 times on a mass basis.
• Pigment G-4 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 4 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-4.
• Example 5 The same procedure was repeated except that p-cresol in the synthesis of intermediate G-2a in Example 2 was changed to p-methoxyphenol (9.47 g), to give 8.16 g of intermediate G-5a (yield 55%).
• Intermediate G-5a was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 409 ([M+1] + )).
• Pigment G-5 (green pigment) was obtained in the same manner as in Example 1, except that 3,6-difluoro-4,5-bisphenoxyphthalonitrile was replaced with Intermediate G-5a (8.16 g). The yield was 6.71 g, the yield rate was 70%, and the solubility in acetone at 25° C. was less than 0.005% by mass, confirming that the product was a pigment rather than a dye.
• Pigment G-5 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 1700 ([M+1] + )). In the production of pigment G-5, the ratio of the amount of the solvent to the amount of the phthalonitrile compound was 1.8 times on a mass basis.
• Pigment G-5 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 5 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-5.
• Example 6 Pigment G-6 (green pigment) was obtained in the same manner as in Synthesis Example 1, except that 3,6-difluoro-4,5-bis(4-chlorophenoxy)phthalonitrile (6.00 g) was used instead of 3,6-difluoro-4,5-bisphenoxyphthalonitrile.
• the yield was 4.43 g, the yield rate was 71%, and the solubility in acetone at 25° C. was less than 0.005% by mass, confirming that the product was a pigment, not a dye.
• Pigment G-6 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 1735 ([M+1] + )). In the production of pigment G-6, the ratio of the amount of the solvent to the amount of the phthalonitrile compound was 1.8 times on a mass basis.
• Pigment G-6 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 6 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-6.
• Example 7 Pigment G-7 (green pigment) was obtained in the same manner as in Example 1, except that 3,6-difluoro-4,5-bis(4-methoxycarbonylphenoxy)phthalonitrile (1.40 g) was used instead of 3,6-difluoro-4,5-bisphenoxyphthalonitrile.
• the yield was 0.810 g, the yield rate was 56%, and the solubility in acetone at 25° C. was less than 0.005% by mass, confirming that the product was a pigment, not a dye.
• Pigment G-7 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 1924 ([M+1] + )). In the production of pigment G-7, the ratio of the amount of the solvent used to the amount of the phthalonitrile compound used was 1.9 times on a mass basis.
• Pigment G-7 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 7 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-7.
• Example 8 3,6-Difluoro-4,5-bis(4-phenoxycarbonylphenoxy)phthalonitrile (2.00 g) and benzonitrile (4 mL) were placed in a 100 mL recovery flask and stirred at 125° C. for 1 hour under a nitrogen atmosphere. Subsequently, zinc iodide (0.326 g) was added and the mixture was stirred at 170° C. for 4 hours to cause a reaction, resulting in the precipitation of crystals. The contents of the recovery flask were cooled to 25° C., and the crystals obtained were filtered out and washed with 50 mL of benzonitrile to obtain Pigment G-8 (green pigment).
• Pigment G-8 was identified as the following compound by MALDI-TOFMS (MALDI-TOFMS: 2420 ([M+1] + )). In the production of pigment G-8, the ratio of the amount of the solvent to the amount of the phthalonitrile compound was 2.0 times on a mass basis.
• Pigment G-8 was subjected to powder X-ray diffraction in the same manner as in Example 1, and the number of diffraction peaks at angles between 3° and 7° was confirmed. The results are shown in Table 1.
• Pigment dispersion 8 was obtained in the same manner as in Example 1, except that pigment G-1 was replaced with pigment G-8.
• C.I. Pigment Green 58 (hereinafter also referred to as "PG58") was prepared.
• the structure of PG58 is shown below.
• the solubility of PG58 in acetone at 25°C was less than 0.005% by mass, and it was confirmed that PG58 was a pigment, not a dye.
• Pigment dispersion A was obtained in the same manner as in Example 1, except that pigment G-1 was changed to PG58.
• the yield was 3.02 g, the yield was 45%, and the solubility in acetone at 25° C. was 2.0% by mass, and it was confirmed to be a dye.
• Compound G-10 was identified by MALDI-TOFMS as a compound having the same structure as pigment G-8 (MALDI-TOFMS: 2420 ([M+1] + )).
• MALDI-TOFMS MALDI-TOFMS: 2420 ([M+1] + )
• Pigment dispersion 1 a polyurethane resin (HYDRAN (registered trademark) AP-40F (manufactured by DIC Corporation)) and ion-exchanged water were mixed to produce aqueous pigment dispersion 1 having a pigment content of 10 mass % and a polyurethane resin non-volatile content of 2 mass %. The following components were mixed to obtain colored composition 1.
• HUDRAN registered trademark
• AP-40F manufactured by DIC Corporation
• composition of Coloring Composition 1 Aqueous pigment dispersion 1 (non-volatile content 4.5% by mass) 40 parts by mass 1,2-hexanediol 5 parts by mass Glycerin 10 parts by mass Surfynol 465 (surfactant, manufactured by Air Products and Chemicals Co., Ltd.) 1 part by mass Ion-exchanged water 44 parts by mass
• Colored compositions 2 to 8 were obtained in the same manner as described above, except that the pigment dispersion 1 was changed to pigment dispersions 2 to 8.
• a colored composition A was obtained in the same manner as described above, except that the pigment dispersion liquid 1 was changed to the pigment dispersion liquid A.
• a colored composition B was obtained in the same manner as described above, except that the aqueous pigment dispersion 1 was changed to compound G-9.
• a colored composition C was obtained in the same manner as described above, except that the aqueous pigment dispersion 1 was changed to compound G-10.
• the image was irradiated with xenon light (85,000 lux) for 100 hours using a weather meter (Ci65, manufactured by Atlas), and the reflection density after irradiation with xenon light was measured using a reflection densitometer (X-Rite i1Pro, manufactured by X-Rite).
• the reflection density of the image before irradiation with the xenon light was set to 1.0.
• the compound remaining rate (%) before and after irradiation with xenon light was calculated from the following formula and evaluated based on the following evaluation criteria. The evaluation results are summarized in Table 1. It should be noted that a higher compound residual rate (%) indicates that the phthalocyanine compound contained in the image has better light resistance.
• the viscosity of the colored composition was measured before and after storage, and the viscosity increase rate (viscosity after storage-viscosity before storage)/viscosity before storage x 100 was calculated and evaluated based on the following evaluation criteria.
• the evaluation results are summarized in Table 1.
• the viscosity of the colored composition was measured using a viscometer RE85L (rotor: 1°34′ ⁇ R24, measurement range 0.6 to 1200 mPa ⁇ s) manufactured by Toki Sangyo Co., Ltd., with the temperature adjusted to 25° C. (Evaluation criteria)
• B The viscosity increase rate was more than 10%.
• Example 9 20 parts by mass of pigment G-1, 10 parts by mass of Solsperse (registered trademark) 32000 (polymer dispersant, manufactured by Lubrizol Corporation, weight average molecular weight 32,000), and 70 parts by mass of propylene glycol monomethyl ether acetate (solvent) were mixed, filled with zirconia beads having a diameter of 0.5 mm, and dispersed for 2 hours using a ball mill to obtain pigment dispersion liquid 1A.
• Solsperse registered trademark
• 32000 polymer dispersant, manufactured by Lubrizol Corporation, weight average molecular weight 32,000
• solvent propylene glycol monomethyl ether acetate
• Example 10 Pigment dispersion 5A was obtained in the same manner as in Example 9, except that pigment G-1 was changed to pigment G-5.
• Example 11 Pigment dispersion liquid 1B was obtained in the same manner as in Example 9, except that propylene glycol monomethyl ether acetate was changed to ethyl 3-ethoxypropionate.
• Example 12 20 parts by mass of pigment G-1, 10 parts by mass of Solsperse (registered trademark) 32000 (polymer dispersant, manufactured by Lubrizol Corporation, weight average molecular weight 32,000), 70 parts by mass of propylene glycol monomethyl ether acetate (solvent), and 7 parts by mass of N-methylpyrrolidone (amide solvent) were mixed, filled with zirconia beads having a diameter of 0.5 mm, and dispersed for 2 hours using a ball mill, to obtain pigment dispersion liquid 1C.
• Solsperse registered trademark
• 32000 polymer dispersant, manufactured by Lubrizol Corporation, weight average molecular weight 32,000
• solvent propylene glycol monomethyl ether acetate
• N-methylpyrrolidone amide solvent

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