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WO2018030506A1 - Composition de pigment, matériau de revêtement contenant cette composition de pigment, et agent de dispersion - Google Patents

Composition de pigment, matériau de revêtement contenant cette composition de pigment, et agent de dispersion Download PDF

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Publication number
WO2018030506A1
WO2018030506A1 PCT/JP2017/029049 JP2017029049W WO2018030506A1 WO 2018030506 A1 WO2018030506 A1 WO 2018030506A1 JP 2017029049 W JP2017029049 W JP 2017029049W WO 2018030506 A1 WO2018030506 A1 WO 2018030506A1
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WO
WIPO (PCT)
Prior art keywords
group
pigment
resin
acidic group
pigment composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2017/029049
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English (en)
Japanese (ja)
Inventor
紗也佳 齋藤
雅之 藤木
勇輝 平林
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toyocolor Co Ltd
Artience Co Ltd
Original Assignee
Toyo Ink SC Holdings Co Ltd
Toyocolor Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2017132462A external-priority patent/JP2018028059A/ja
Application filed by Toyo Ink SC Holdings Co Ltd, Toyocolor Co Ltd filed Critical Toyo Ink SC Holdings Co Ltd
Publication of WO2018030506A1 publication Critical patent/WO2018030506A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds

Definitions

  • the embodiment of the present disclosure relates to an aqueous pigment composition particularly suitable for an aqueous composition.
  • Other embodiment of this indication is related with the coating material containing the said pigment composition.
  • Yet another embodiment of the present disclosure relates to a dispersant.
  • Color materials used as colorants are roughly classified into dyes and pigments.
  • the printed material has excellent characteristics such as water fastness and light fastness as compared with the case of using a dye as the color material.
  • pigments have problems of low transparency and low color developability in comparison with dyes.
  • a dispersion using a dye a dye which is a color material is used after being dissolved in a medium
  • a pigment dispersion a pigment which is a color material is used by being dispersed in the medium.
  • a method of dispersing a powder pigment using a surfactant or a water-soluble resin is generally used, and this method is still widely used today. Yes.
  • a paint containing a pigment dispersed using a surfactant has a problem that the resulting coating film has extremely poor water resistance and can be used only for limited applications.
  • Small organic particle color pigments generally have poor pigment dispersibility and tend to be energetically stable even after being dispersed in a paint. Therefore, the organic coloring pigment aggregates in the paint, and the size of the particles changes or the adsorption to other pigments easily occurs. These phenomena are various even in a state where the paint is formed into a coating film. May cause performance degradation.
  • the pH of the aqueous dispersion of the pigment finely dispersed using a resin having a carboxyl group neutralized with a basic compound is neutral or acidic using an acidic compound.
  • the resin is firmly fixed to the pigment (hereinafter, this step is referred to as “acid precipitation”), and then, if necessary, the aqueous dispersion after acid precipitation is filtered and washed with water.
  • a method of producing an aqueous pigment dispersion by neutralizing a carboxyl group again with a basic compound and redispersing it in water is known. According to this method, it is possible to prepare an aqueous pigment dispersion in which the pigment is finely dispersed to an extent sufficient to exhibit gloss, color developability, and coloring power, and also has excellent storage stability (patent) References 1, 2).
  • Patent Document 3 Also known is a method of obtaining a powder or solid pigment by performing acid precipitation using a limited resin such as a relatively high molecular weight acrylic resin.
  • a dispersant capable of finely dispersing a pigment at a high level a dispersant as described in Patent Document 4 is known.
  • this dispersant is excellent in dispersibility when the dispersion medium is a solvent, but cannot be applied when the dispersion medium is water.
  • a paint color having a high pigment concentration may be set in accordance with a demand for a paint color having excellent design and vivid high saturation.
  • the coating color is constituted by using an organic coloring pigment having poor dispersibility, there is a limit in coating film performance.
  • solvent type paints are concerned about environmental impacts, conversion to water-based paints is required.
  • JP-A-9-31360 Japanese Patent Laid-Open No. 50-122528 JP 11-199783 A WO2008 / 007776
  • the problem to be solved by the present invention is to provide a pigment composition that is excellent in dispersibility and excellent in hue, water resistance, haze value, and flip-flop properties, which cannot be achieved by the above-described conventional technology. It is in. Moreover, it is providing the water-based coating material which is excellent in the designability using the said pigment composition.
  • An embodiment of the present invention is a pigment composition containing a neutralized product of an acidic group-containing dispersant (S) and a basic compound, a pigment and water, wherein the acidic group-containing dispersant (S) is:
  • the present invention relates to a pigment composition containing the resin (S1) or (S2).
  • (S1) A resin which is a reaction product of the hydroxyl group of the polymer (A) having a hydroxyl group and an acidic group and the acid anhydride group of a tricarboxylic acid anhydride and / or tetracarboxylic dianhydride.
  • the polymer (A) having a hydroxyl group and an acidic group in the resin (S1) is an acidic group-containing ethylene in the presence of a compound (b1) having two hydroxyl groups and one thiol group in the molecule.
  • the polymer (a1) obtained by polymerizing the ethylenically unsaturated monomer (C) containing the polymerizable unsaturated monomer (c1) is preferable.
  • the content of the acidic group-containing ethylenically unsaturated monomer (c1) is preferably 3% by mass to 30% by mass with respect to the total amount of the ethylenically unsaturated monomer (C). .
  • the acidic group-containing dispersant (S) preferably has a weight average molecular weight of 7,000 to 25,000 and an acid value of 20 to 130.
  • the content of the acidic group-containing dispersant (S) is preferably 10% by mass to 30% by mass with respect to the total amount of the pigment.
  • the basic compound is preferably an organic amine.
  • the organic amine is preferably an alkanolamine.
  • the pH of the pigment composition is preferably 8-11.
  • the pigment is preferably at least one selected from the group consisting of diketopyrrolopyrrole, quinacridone and perylene.
  • the binder resin preferably includes an acrylic resin and a melamine resin.
  • Another embodiment of the present invention is a dispersant that is a neutralized product of an acidic group-containing dispersant (S) and a basic compound, wherein the acidic group-containing dispersant (S) is the following (S1) or ( The present invention relates to a dispersant containing the resin S2).
  • S1 A resin which is a reaction product of the hydroxyl group of the polymer (A) having a hydroxyl group and an acidic group and the acid anhydride group of a tricarboxylic acid anhydride and / or tetracarboxylic dianhydride.
  • a pigment composition having excellent dispersibility and good hue can be provided.
  • the coating material which is excellent in design property can be provided.
  • the pigment composition according to the first embodiment of the present invention is a liquid obtained by dispersing a pigment in a liquid medium containing water as a main component.
  • the pigment composition is composed of an acidic group-containing dispersant (S) and a basic compound. It is a pigment composition containing a hydrate, a pigment, and water.
  • the “neutralized product of the acidic group-containing dispersant (S) and the basic compound” described in the present specification means that the acidic group in the acidic group-containing dispersant (S) is sufficient by the basic compound in the pigment composition.
  • the step of forming a neutralized product of the acidic group-containing dispersant (S) and the basic compound is not essential.
  • a sufficient amount of the basic compound may be used to completely neutralize the acidic group of the agent (S).
  • the pH of the pigment composition is preferably 6 or more, and more preferably 8 or more. When the pH of the pigment composition is adjusted to 6 or more, it becomes easy to sufficiently neutralize the acidic groups of the acidic group-containing dispersant (S). By neutralizing the acidic group, charge repulsion necessary for pigment dispersion can be secured.
  • the upper limit of the pH is not particularly limited, but in one embodiment, the pH is preferably 11 or less from a practical viewpoint. In one embodiment, the pH of the pigment composition is preferably in the range of 8 to 11 because it becomes easy to completely neutralize the acidic group.
  • the resins (S1) and (S2) contained in the acidic group-containing dispersant (S) are mainly 2 of the polymerization reaction of ethylenically unsaturated double bonds and the esterification reaction of a hydroxyl group and an acid anhydride group. It has a complicated structure obtained by two reactions, and cannot be represented by a general formula (structure) or is not realistic. Therefore, it describes according to a manufacturing method about the said resin.
  • the acidic group-containing dispersant (S) contains the following resin (S1) or (S2).
  • the acidic group-containing dispersant (S) preferably consists essentially of the following resin (S1) or (S2), and more preferably comprises the following resin (S1) or (S2). .
  • (S1) A resin which is a reaction product of the hydroxyl group of the polymer (A) having a hydroxyl group and an acidic group and the acid anhydride group of a tricarboxylic acid anhydride and / or tetracarboxylic dianhydride.
  • the resin (S1) can be produced by a known method such as WO2008 / 007776 and JP2008-029901.
  • the polymer (A) having a hydroxyl group and an acidic group is preferably a polymer having a hydroxyl group at the terminal and an acidic group in the side chain.
  • the polymer (A) is obtained by polymerizing an ethylenically unsaturated monomer (C) containing an acidic group-containing ethylenically unsaturated monomer (c1) in the presence of a compound (B) having a hydroxyl group. It may be the polymer (a1) obtained.
  • the compound (B) having a hydroxyl group is preferably a compound having a hydroxyl group and a thiol group in the molecule as described later. Especially, since it is preferable that there are two or more terminal hydroxyl groups, the compound (b1) which has two hydroxyl groups and one thiol group in a molecule
  • numerator is used suitably.
  • the polymer (A) is a polymer having two hydroxyl groups at one end.
  • This polymer is an ethylenically unsaturated monomer containing an acidic group-containing ethylenically unsaturated monomer (c1) in the presence of a compound (b1) having two hydroxyl groups and one thiol group in the molecule. It can be obtained as a polymer (a1) obtained by polymerizing (C).
  • an acid anhydride ring Carboxylic acid groups are formed by ring opening of the structure.
  • the resin (S2) can be produced by a known method such as JP 2010-185934 A.
  • the hydroxyl group of the compound (B) having a hydroxyl group, a tricarboxylic anhydride and / or a tetracarboxylic dianhydride A polymer obtained by polymerizing an ethylenically unsaturated monomer (C) containing an acidic group-containing ethylenically unsaturated monomer (c1) in the presence of a reaction product with an acid anhydride group of the product. It may be.
  • a reaction product of the hydroxyl group of the compound (b1) having two hydroxyl groups and one thiol group in the molecule and the acid anhydride group of tricarboxylic anhydride and / or tetracarboxylic dianhydride in the presence of a reaction product of the hydroxyl group of the compound (b1) having two hydroxyl groups and one thiol group in the molecule and the acid anhydride group of tricarboxylic anhydride and / or tetracarboxylic dianhydride.
  • a polymer obtained by polymerizing an ethylenically unsaturated monomer (C) containing an acidic group-containing ethylenically unsaturated monomer (c1) is preferable.
  • the difference between the resins (S1) and (S2) is that the introduction of the polymer site by polymerization of the ethylenically unsaturated monomer (C) including the acidic group-containing ethylenically unsaturated monomer (c1) Or only later. Therefore, although the molecular weight and the like may be slightly different depending on various conditions, the same resin can be theoretically obtained if the raw materials and the reaction conditions are the same. Although not particularly limited, the resin (S1) is more preferable from the viewpoint of stable production. Hereinafter, the starting materials used for producing the resins (S1) and (S2) will be specifically described.
  • the polymer (A) having a hydroxyl group and an acidic group in the resin (S1) is preferably a polymer having a hydroxyl group at a terminal and an acidic group in a side chain.
  • an acidic group-containing ethylenically unsaturated monomer (c1) is included in the presence of a compound (b1) having two hydroxyl groups and one thiol group in the molecule.
  • a polymer (a1) obtained by polymerizing the ethylenically unsaturated monomer (C) is exemplified.
  • the proportion of the compound (b1) is more preferably 3 to 12 parts by weight, still more preferably 4 to 12 parts by weight, and particularly preferably 5 to 9 parts by weight.
  • the weight average molecular weight of the polymer (A) is preferably 1,000 to 10,000, more preferably 2,000 to 8,000, still more preferably 2,000 to 6,000, and particularly preferably 3,000 to 10,000. 5,000.
  • part with respect to this polymer (A) becomes an affinity site
  • a polymerization initiator can be arbitrarily used with respect to 100 parts by weight of the ethylenically unsaturated monomer (C).
  • the polymerization initiator an azo compound and an organic peroxide can be used.
  • azo compounds examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane 1-carbonitrile), 2 , 2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2'-azobis (2-methylpropionate) 4,4′-azobis (4-cyanovaleric acid), 2,2′-azobis (2-hydroxymethylpropionitrile), 2,2′-azobis [2- (2-imidazolin-2-yl) Propane] and the like.
  • organic peroxides examples include benzoyl peroxide, t-butyl perbenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di (2-ethoxyethyl) peroxy
  • examples thereof include dicarbonate, t-butyl peroxyneodecanoate, t-butyl peroxybivalate, (3,5,5-trimethylhexanoyl) peroxide, dipropionyl peroxide, diacetyl peroxide and the like.
  • These polymerization initiators can be used alone or in combination of two or more.
  • the polymerization solvents are ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethylene glycol mono Ethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and the like are used, but are not particularly limited thereto.
  • the solvent (polymerization solvent) used for the polymerization reaction can be removed by an operation such as distillation after the completion of the reaction.
  • the polymerization solvent can be used as it is as a solvent for the next step or as part of a product.
  • the reaction temperature is preferably 40 to 150 ° C, more preferably 50 to 110 ° C.
  • the polymerization reaction of the ethylenically unsaturated monomer (C) including the acidic group-containing ethylenically unsaturated monomer (c1) in the resin (S2) is performed in the same manner as described above.
  • the compound (B) having a hydroxyl group in the resin (S2) preferably contains a compound having a hydroxyl group and a thiol group in the molecule.
  • the compound having a hydroxyl group and a thiol group in the molecule is not limited as long as it has a hydroxyl group and a thiol group.
  • a compound having two hydroxyl groups and one thiol group in a molecule described later may be used.
  • Compounds having one hydroxyl group and one thiol group in the molecule such as mercaptoethanol; Compounds having one hydroxyl group and two thiol groups in the molecule, such as 1,2-dimercapto-3-propanol and 1,3-dimercapto-2-propanol; Compounds having one hydroxyl group and three or more thiol groups in the molecule, such as pentaerythritol tris (3-mercaptoacetate) and dipentaerythritol pentakis (3-mercaptopropionate); Compounds having two hydroxyl groups and two thiol groups in the molecule, such as 1,2-dimercapto-1,2-ethanediol; Compounds having three or more hydroxyl groups and two thiol groups in the molecule, such as dimercaptodipentaerythritol; Compounds having two or more hydroxyl groups and three or more thiol groups in the molecule, such as
  • Compound (b1) having two hydroxyl groups and one thiol group in the molecule examples include 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, and 3-mercapto-1,2-propane.
  • Diol (hereinafter abbreviated as thioglycerin or thioglycerol), 2-mercapto-1,2-propanediol, 2-mercapto-2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3 -Propanediol, 1-mercapto-2,2-propanediol, 2-mercaptoethyl-2-methyl-1,3-propanediol, 2-mercaptoethyl-2-ethyl-1,3-propanediol, etc. It is done. Of these, 3-mercapto-1,2-propanediol is preferable.
  • the compound (B) having a hydroxyl group in the resin (S2) may contain a compound other than the compound having a hydroxyl group and a thiol group in the molecule exemplified above.
  • polyhydric alcohols such as ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, or hexanetriol
  • Polyether glycols such as polyoxyethylene glycol, polyoxypropylene glycol, or polyoxyethylene polyoxypropylene polyoxytetramethylene glycol
  • Modified polyether polyols obtained by ring-opening polymerization of the polyhydric alcohols with (cyclic) ether bond-containing compounds such as ethylene oxide, propylene oxide, or allyl glycidyl ether
  • Polyester polyols obtained by co-condensation of one or more of the above polyhydric alcohols with polyvalent carboxylic acids, wherein the poly
  • the ethylenically unsaturated monomer (C) includes an acidic group-containing ethylenically unsaturated monomer (c1).
  • acid group-containing ethylenically unsaturated monomer (c1)) examples include ethylenically unsaturated monomers having a carboxyl group such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, and crotonic acid; From an ethylenically unsaturated monomer having a carboxylic anhydride group such as maleic anhydride and itaconic anhydride, and an ethylenically unsaturated monomer having sulfonic acid, phosphoric acid, fluoric acid, etc. Species or two or more can be selected. In particular, from the viewpoint of dispersibility of the pigment, an ethylenically unsaturated monomer having a carboxyl group is preferable.
  • alkyl (meth) acrylates two or more selected from the group consisting of alkyl (meth) acrylates, (meth) acrylates having an aromatic substituent, and alkoxyalkylene (meth) acrylates
  • alkoxyalkylene (meth) acrylates These monomers are preferably used in combination.
  • the methyl (meth) acrylate content is preferably 15% by mass to 80% by mass and more preferably 30% by mass to 50% by mass with respect to the total amount of the ethylenically unsaturated monomer (C). More preferred.
  • the content of the acidic group-containing ethylenically unsaturated monomer (c1) is 3% by mass to 30% by mass with respect to the total amount of the ethylenically unsaturated monomer (C). Is preferred. In one embodiment, the content is more preferably 4% by mass to 25% by mass.
  • the hydroxyl group of the polymer (A) in the resin (S1) or the hydroxyl group of the compound (B) in the resin (S2) is an acid containing a tricarboxylic acid anhydride and / or a tetracarboxylic dianhydride described below.
  • An ester bond is formed by reaction with an anhydride.
  • the acid anhydride will be described.
  • Tricarboxylic anhydride Examples of the tricarboxylic acid anhydride include aliphatic tricarboxylic acid anhydrides or aromatic tricarboxylic acid anhydrides.
  • Examples of the aliphatic tricarboxylic acid anhydride include 3-carboxymethylglutaric acid anhydride, 1,2,4-butanetricarboxylic acid-1,2-anhydride, cis-propene-1,2,3-tricarboxylic acid- 1,2-anhydride, 1,3,4-cyclopentanetricarboxylic acid anhydride and the like.
  • Examples of the aromatic tricarboxylic acid include benzene tricarboxylic acid anhydride (1,2,3-benzene tricarboxylic acid anhydride, trimellitic acid anhydride [1,2,4-benzene tricarboxylic acid anhydride], etc.), naphthalene tricarboxylic acid, and the like.
  • Acid anhydrides (1,2,4-naphthalene tricarboxylic acid anhydride, 1,4,5-naphthalene tricarboxylic acid anhydride, 2,3,6-naphthalene tricarboxylic acid anhydride, 1,2,8-naphthalene tricarboxylic acid anhydride 3,4,4′-benzophenone tricarboxylic acid anhydride, 3,4,4′-biphenyl ether tricarboxylic acid anhydride, 3,4,4′-biphenyl tricarboxylic acid anhydride, 2,3,2 ′ -Biphenyltricarboxylic acid anhydride, 3,4,4'-biphenylmethanetricarboxylic acid anhydride, or 3,4,4'-biphenylsulfo Tricarboxylic anhydride and the like.
  • tetracarboxylic dianhydride examples include 1,2,3,4-butanetetracarboxylic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,3-dimethyl-1,2 , 3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 2,3,5-tricarboxycyclopentylacetic dianhydride, 3,5,6- Tricarboxynorbornane-2-acetic acid dianhydride, 2,3,4,5-tetrahydrofurantetracarboxylic dianhydride, 5- (2,5-dioxotetrahydrofural) -3-methyl-3-cyclohexene-1, 2-dicarboxylic dianhydrides or aliphatic tetracarboxylic dianhydrides such as bicyclo [2,2,2] -oc
  • the tetracarboxylic dianhydride is not limited to the compounds exemplified above, and may have two carboxylic anhydride groups in the molecule and may have any structure. These compounds may be used alone or in combination.
  • the tricarboxylic acid anhydride and tetracarboxylic acid dianhydride in the resins (S1) and (S2) are preferably tetracarboxylic acid dianhydrides and more preferably aromatic tetracarboxylic acid dianhydrides from the viewpoint of adsorptivity to the pigment. .
  • pyromellitic dianhydride is more preferable.
  • the aromatic carboxylic dianhydride is used, the pigment adsorbing ability is higher than that of the aliphatic carboxylic dianhydride.
  • the resin (S1) is obtained by the reaction (polyester synthesis) of the hydroxyl group of the polymer (A) having the hydroxyl group and acidic group described above with the acid anhydride group of tricarboxylic anhydride and / or tetracarboxylic dianhydride. be able to.
  • the resin (S2) is obtained by reacting the hydroxyl group of the above-described compound (B) having a hydroxyl group with the acid anhydride group of tricarboxylic acid anhydride and / or tetracarboxylic dianhydride (polyester synthesis).
  • polyester synthesis can be carried out as follows.
  • the polymerization in the resin (S2) is as described above.
  • (Reaction solvent) Polyester synthesis can be carried out using only the raw materials exemplified above, but it is preferable to carry out using a solvent in order to avoid problems such as high viscosity and non-uniform reaction.
  • a solvent which can be used at the time of a synthesis
  • combination You may be a well-known solvent.
  • acetone methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl acetate, butyl acetate, toluene, xylene, acetonitrile and the like can be mentioned.
  • the solvent used in the synthesis can be removed by an operation such as distillation after the completion of the reaction.
  • the reaction solvent can be used as it is as the solvent for the next step or as part of the product.
  • reaction catalyst As a catalyst used for polyester synthesis, a known catalyst can be used.
  • the catalyst is preferably a tertiary amine compound.
  • triethylamine triethylenediamine, N, N-dimethylbenzylamine, N-methylmorpholine, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1,5-diazabicyclo- [4.3.0 ] -5-nonene and the like.
  • reaction temperature The reaction temperature of the polyester synthesis is 50 ° C to 180 ° C, preferably 80 ° C to 140 ° C.
  • the reaction rate is slow, and when the reaction temperature is 180 ° C. or higher, the carboxyl group and the hydroxyl group may undergo an esterification reaction, resulting in a decrease in acid value or gelation.
  • the reaction is stopped by reacting until the absorption of acid anhydride disappears by infrared absorption.
  • the reaction may be stopped when the acid value of the polyester falls within the range of 5 to 200, or when the hydroxyl value falls within the range of 20 to 200.
  • the weight average molecular weight of the acidic group-containing dispersant (S) is preferably 7,000 to 25,000, more preferably 10,000 to 20,000. If the weight average molecular weight is less than 7,000, the stability of the pigment composition may be lowered, and if it exceeds 25,000, the interaction between the resins becomes strong and the viscosity may increase.
  • the acid value of the obtained acidic group-containing dispersant (S) is preferably 20 to 130. More preferably, it is 30 to 120. In one embodiment, the acid value is more preferably 60 to 110.
  • the pigment used in the pigment composition can be arbitrarily selected from conventionally known various organic pigments and inorganic pigments, and is not particularly limited in terms of hue or structure.
  • a pigment composition using an organic pigment as the pigment is preferred.
  • organic pigments include phthalocyanine, dioxazine violet, indanthrene blue, perylene, quinacridone, diketopyrrolopyrrole, azo, anthraquinone, quinophthalone, isoindoline, quinoxaline and These metal complex pigments can be mentioned.
  • the organic pigment represented by the general formula known as a superordinate concept of these organic pigments can also be applied.
  • specific pigments that can be used are exemplified.
  • phthalocyanine examples include C.I. I. Pigment Blue (hereinafter abbreviated as PB) 1, PB2, PB14, PB16, PB15: 1, PB15: 2, PB15: 3, PB15: 4, PB15: 5, PB15: 6, aluminum phthalocyanine, C.I. I. Pigment green (hereinafter abbreviated as PG) 1, PG2, PG3, PG4, PG7, PG36, PG45, PG58, PG62, and the like.
  • dioxazine violet series examples of the dioxazine violet pigment include C.I. I. Pigment violet (hereinafter abbreviated as PV) 1, PV2, PV3, PV4, PV12, PV23, PV27, PV39, PV50 and the like.
  • indanthrene Blue examples include PB60 and PB64.
  • perylene pigments examples include C.I. I. Pigment red (hereinafter abbreviated as PR) 123, PR149, PR178, PR179, PR190, PV29, and the like.
  • quinacridone pigment examples include PR122, PR202, PR206, PR207, PR209, PV19, PV42, and the like.
  • Examples of the diketopyrrolopyrrole pigment include PR254, PR255, PR264, C.I. I. Pigment orange (hereinafter abbreviated as PO) 71, PO73, and the like.
  • anthraquinone examples include PR168, PR177, and PO40.
  • isoindoline series examples include PY139, PY185, PO66, PO69, PR260 and the like.
  • Metal complex system examples of the metal complex pigment include PY117, PY129, PY150, PY153, and the like.
  • the pigment constituting the pigment composition is preferably phthalocyanine, dioxazine violet, indanthrene blue, perylene, quinacridone, diketopyrrolopyrrole, azo and anthraquinone.
  • Is at least one selected from the group consisting of More preferred is at least one organic pigment selected from the group consisting of diketopyrrolopyrrole, quinacridone and perylene, and particularly preferred is a perylene pigment.
  • a pigment composition is prepared by selecting a pigment from the above exemplified pigments so as to match a target hue. Any pigment may be used alone in each color paint, or two or more pigments may be mixed and used. Of course, the pigments that can be used in the pigment composition are not limited to the above pigments. It is also possible to use newly produced pigments.
  • the basic compound used in the pigment composition examples include organic amines such as aqueous ammonia, dimethylaminoethanol, ethanolamine, diethanolamine, triethanolamine, aminemethylpropanol, and triethylamine; sodium hydroxide, lithium hydroxide, hydroxide It may be an inorganic alkali agent of an alkali metal hydroxide such as potassium; an organic acid or a mineral acid. Among these, organic amines and inorganic alkali agents are preferable, and organic amines are more preferable. Examples of the organic amine include dimethylaminoethanol, diethylaminoethanol, ethanolamine, diethanolamine, and triethanolamine. Among them, alkanolamines such as dimethylaminoethanol and ethanolamine are particularly preferable.
  • the water used in the pigment composition is preferably ion-exchanged water (deionized water), not general water containing various ions.
  • the pigment composition can be produced by mixing a pigment, an acidic group-containing dispersant (S), a basic compound, water, and other resins and additives as necessary, and then dispersing.
  • the dispersion treatment can be carried out using various conventionally known dispersers such as a three-roll mill, a two-roll mill, a kneader, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor.
  • a pigment composition in which several types of pigments are separately dispersed can be mixed and used.
  • the acidic group-containing dispersant (S) can finely and stably disperse the pigment. Therefore, the resin composition is excellent in dispersibility and hue. In addition, since the acidic group-containing dispersant (S) is also excellent in compatibility with other resins, by using the pigment composition and the binder resin, it is excellent in dispersibility and hue. A paint having an excellent design can be produced.
  • the blending amount of the acidic group-containing dispersant (S) is preferably 5 to 120% by mass, more preferably 10 to 100% by mass, and further preferably 10 to 50% by mass with respect to the total amount of the pigment. Particularly preferred is 10 to 30% by mass.
  • the acidic group-containing dispersant (S) is neutralized by a basic compound and dispersed or dissolved in an aqueous liquid medium.
  • the pH of the pigment composition is preferably adjusted to 6 to 11, more preferably the pH is adjusted to 8 to 11.
  • the basic compound facilitates water-solubilization of the resin with respect to the acid value of the combined carboxyl group and ring-opened acid anhydride group contained in the acidic group-containing dispersant (S), and From the viewpoint of improving pigment dispersibility, it is preferably used at a ratio of 1.0 equivalent or more.
  • the pigment composition can be prepared by mixing and dispersing each component in one step as described above.
  • the method for producing the pigment composition includes a step of producing a neutralized product of the acidic group-containing dispersant (S) and the basic compound in water (preferably ion-exchanged water), Next, the obtained solution may have a step of adding and mixing a pigment, and if necessary, other resins and additives, followed by dispersion treatment.
  • the neutralized product of the acidic group-containing dispersant (S) and the basic compound functions as a pigment dispersant.
  • one embodiment is a pigment dispersant which is a neutralized product of an acidic group-containing dispersant (S) and a basic compound, wherein the acidic group-containing dispersant (S) is the following (S1) or ( The present invention relates to a pigment dispersant containing the resin of S2).
  • S1 A resin which is a reaction product of the hydroxyl group of the polymer (A) having a hydroxyl group and an acidic group and the acid anhydride group of a tricarboxylic acid anhydride and / or tetracarboxylic dianhydride.
  • the content of solids other than the pigment is preferably 10% by mass or more, and more preferably 60% by mass or less, based on the total amount of the pigment composition.
  • the content is preferably 10 to 60% by mass, more preferably 20 to 50% by mass, and further preferably 30 to 40% by mass.
  • the content of the pigment is preferably 5% by mass or more and more preferably 70% by mass or less based on the total amount of the pigment composition.
  • the content is preferably 5 to 70% by mass, more preferably 10 to 60% by mass, and still more preferably 20 to 50% by mass.
  • a water-soluble solvent miscible with water may be added to the pigment composition.
  • various additives may be added.
  • antifoaming agents, preservatives, pigment derivatives, other pigments, and the like can be added. These are not particularly limited as long as they do not hinder the dispersibility of the pigment, but are preferably those that dissolve in water.
  • a dispersion aid By using a dispersion aid, the dispersibility of the pigment can be improved, and re-aggregation of the pigment after dispersion can be more effectively prevented.
  • an acetylene glycol surfactant and / or an acetylene alcohol surfactant is preferable.
  • acetylene glycol surfactants and / or acetylene alcohol surfactants include 2,4,7,9-tetramethyl-5-decyne-4,7-diol and 2,4,7,9-tetramethyl- Selected from alkylene oxide adducts of 5-decin-4,7-diol, 2,4-dimethyl-5-decyn-4-ol and alkylene oxide adducts of 2,4-dimethyl-5-decyn-4-ol 1 or more types are preferable.
  • Preservatives are added for the purpose of preventing generation of soot and bacteria in the recording solution, and include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione-1-oxide, 1,2- Benzisothiazolin-3-one, amine salt of 1-benzisothiazolin-3-one, and the like are used. These are preferably contained in the recording liquid in the range of 0.05 to 1.0% by mass.
  • the pigment composition may further contain a dye derivative in order to improve the dispersibility of the pigment.
  • the dye derivative include a compound in which a phthalimidomethyl group which may have a basic substituent and / or an acidic substituent is introduced into an organic pigment such as anthraquinone, acridone or triazine.
  • a compound having an azo skeleton, a naphthol azo skeleton, a diketopyrrolopyrrole skeleton, an anthraquinone skeleton, a quinophthalone skeleton, and a perylene skeleton is preferable from the viewpoints of brightness and dispersibility.
  • pigment derivative when used, all components including the pigment derivative may be mixed and dispersed. Alternatively, initially only the pigment and dye derivative, or only the dye derivative and acidic group-containing dispersant (S), or only the pigment, dye derivative and acidic group-containing dispersant (S) are dispersed, Other components may be added and dispersed again.
  • the blending amount of the pigment derivative is preferably 0.5% by mass or more, more preferably 1% by mass or more based on the total amount of the additive pigment (100% by mass) from the viewpoint of improving the dispersibility of the additive pigment.
  • the total amount of the additive pigment is preferably 40% by mass or less and more preferably 5% by mass or less, based on the total amount (100% by mass).
  • an organic pigment derivative By adding an organic pigment derivative, it is considered that the pigment is adsorbed by the pigment to be dispersed and imparts polarity, thereby giving a dispersion effect from the interaction with the dispersant and the resin.
  • an effect contributing to pigment crystal stabilization and dispersion stabilization can be expected.
  • EFKA-6745, 6750 manufactured by EFKA Additive
  • BYK-Synerg ist2100 manufactured by Big Chemie Japan Co., Ltd.
  • Solsperse 5000, 12000, 22000 manufactured by Nihon Lubrizol Co., Ltd.
  • the second embodiment of the present invention relates to a paint (hereinafter also referred to as an aqueous paint or an aqueous paint composition) containing at least the pigment composition of the first embodiment and a binder resin described later.
  • the ratio of the pigment composition to the binder resin varies depending on the required use and is not particularly limited. It can also be used in applications where the pigment concentration is very low.
  • the content of the binder resin (active ingredient) in the coating composition is preferably 10 to 95% by mass, and more preferably 40 to 90% by mass.
  • the binder resin is not particularly limited as long as it is usually used as a binder resin for paints.
  • a binder resin for paints for example, an acrylic resin, a polyester resin, an alkyd resin, a fluororesin, a urethane resin, a silicon-containing resin containing a crosslinkable functional group.
  • An acid anhydride, an alkoxysilane group-containing compound, a resin, or the like can be used.
  • a resin containing a crosslinkable functional group in combination with a resin having a role as a crosslinking agent.
  • a resin having a role as a crosslinking agent.
  • an acrylic resin and a melamine resin in combination.
  • the melamine resin is particularly preferably used because it has thermosetting properties and acts as a curing agent.
  • the acrylic resin is preferably obtained by polymerizing a monomer having a polymerizable unsaturated double bond well known by those skilled in the art by a conventional method.
  • Examples of the monomer having a polymerizable unsaturated double bond include acrylic acid, methacrylic acid, crotonic acid, isocrotonic acid, ethacrylic acid, propylacrylic acid, isopropylacrylic acid, itaconic acid, maleic anhydride, and fumaric acid.
  • Carboxylic acid group-containing monomers such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and ⁇ -caprolactone-modified acrylic monomer, (meth) acrylic acid Methyl, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, hexyl (meth) acrylate, (meth ) 2-ethylhexyl acrylate, ( (Ta) Octyl acrylate, (meth) acrylate nonyl, (meth) acrylate decyl, (meth) acrylate dodecyl, (meth) acrylate ester monomers such as stearyl (meth) acrylate
  • the water-based coating composition further includes various additives such as water or an organic solvent, a rheology control agent, an anti-settling agent, a curing catalyst, an antifoaming agent, an antioxidant, an ultraviolet absorber, and a surface conditioner, if necessary.
  • An extender pigment etc. can be suitably mix
  • the aqueous coating composition can be prepared by mixing and dispersing the components of the pigment composition, the binder resin, and, if necessary, the aforementioned additional components. Moreover, after mixing the said binder resin and water previously, the said pigment composition and the above-mentioned additional component as needed are further mixed and disperse
  • the said coating material is not specifically limited, It can apply to various base materials.
  • a coated product obtained by applying the coating material on a substrate can be provided.
  • a base material for example, a metal base material such as iron, stainless steel, aluminum, etc. and a surface treated product thereof; a cement base material such as cement, lime, gypsum; polyvinyl chloride, polyester, polycarbonate, acrylic Examples thereof include plastic base materials.
  • various articles to be coated in the building / building materials field such as building materials, buildings, and structures made of metal or plastic materials constituting these various substrates can be used as the substrate.
  • the coating method of the paint is not particularly limited, and examples thereof include brush coating, roller coating, and spray coating.
  • the coating film can be usually obtained by drying at room temperature or drying by heating.
  • the coating amount; the order of coating such as undercoating, intermediate coating, and topcoating; the coating film thickness; the drying time, and the like can be arbitrarily set according to the type of coating composition and the substrate to be applied.
  • the weight average molecular weight is determined by using two separation columns “TSK-GEL SUPER HZM-N” connected in series in Gel Permeation Chromatography (GPC) “HLC-8220GPC” (manufactured by Tosoh Corporation). It is the polystyrene conversion value measured using tetrahydrofuran (THF) for the phase.
  • GPC Gel Permeation Chromatography
  • the temperature in the system was cooled to 70 ° C., and 80.0 parts of methyl methacrylate, 5.0 parts of methacrylic acid, 10.0 parts of hydroxyethyl methacrylate And 5.0 parts of acrylic acid were added, and a solution prepared by dissolving 0.1 part of 2,2′-azobisisobutyronitrile in 26.2 parts of propylene glycol monomethyl ether acetate was added over 10 hours. Reaction was performed. The solid content measurement confirmed that the polymerization had progressed 95%, and the reaction was completed. After completion of the reaction, the nonvolatile content was adjusted to 50% by weight, and an acidic group-containing dispersant S11 having an acid value of 108 mgKOH / g and a weight average molecular weight of 9,500 was obtained.
  • Acid component tricarboxylic anhydride and / or tetracarboxylic dianhydride
  • MAA methacrylic acid AA: acrylic acid
  • 2-MTA methoxyethyl acrylate
  • MMA methyl methacrylate
  • EA ethyl acrylate
  • BzMA benzyl methacrylate t-BA: tarsal Butyl acrylate
  • HEMA hydroxyethyl methacrylate thioglycerol: 3-mercapto-1,2-propanediol
  • AIBN 2,2′-azobisisobutyronitrile
  • PGMAc propylene glycol monomethyl ether acetate
  • PMA pyromellitic dianhydride
  • BPDA 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride
  • Ricacid BT-100 1,2,3,4-butanetetracarboxylic dianhydride
  • the prepared pigment composition was diluted by adding water so that the loading index value of the laser dynamic light scattering method (manufactured by Nikkiso Co., Ltd., UPA150EX) was within the range of 0.8 to 1.2.
  • the median diameter (D50) of the cumulative volume at ° C was measured. Subsequently, evaluation was performed according to the following criteria. A: D50 is 50 nm or less B: D50 is greater than 50 nm and 100 nm or less ⁇ : D50 is greater than 100 nm and 200 nm or less X: D50 is greater than 200 nm
  • Comparative resin 1 Florene G700AMP (manufactured by Kyoeisha Chemical Co., Ltd .: ⁇ -olefin maleic anhydride copolymer partial ester, 2-amino-2-methyl-1-propanol salt)
  • Comparative resin 2 DisperBYK-190 (manufactured by Big Chemie: acrylic block copolymer)
  • Comparative resin 3 ARUFON UC-3000 (manufactured by Toa Gosei Co., Ltd .: all acrylic polymer)
  • PR122 “FASTOGEN Super Magenta RGT” manufactured by DIC PR177: “Cinilex Red SR4C” manufactured by Cinic PR179: “Paliogen Red L3885” manufactured by BASF PR254: “Cinilex DPP Red SR2P” manufactured by Cinic PR264: “Cinilex DPP Rubine SR5H” manufactured by Cinic PB15: 1: “Cyanine Blue G-314” manufactured by Sanyo Dye PB15: 3: “LIONOL BLUE 7919” manufactured by Toyocolor Co., Ltd. PB15: 6: “LIONOL BLUE ESP-S 74160” manufactured by Toyocolor Co., Ltd.
  • Example 76 (Preparation of coating composition C-1) The pigment composition P-1 obtained in Example 1 and the binder resin were blended in a solid content so as to have the following composition to obtain a coating composition C-1.
  • Pigment composition P-1 3.2 parts Watersol S-751: 60.0 parts (acrylic resin for baking paints manufactured by DIC)
  • Example 77 to 150, Comparative Examples 16 to 30 (Preparation of coating compositions C-2 to C-90) Coating compositions C-2 to C-90 were obtained in the same manner as in Example 76 except that the pigment compositions and additive resins (binder resins) shown in Table 4-1 to Table 4-3 and Table 5 were changed. It was.
  • the obtained coating composition was coated on an corona discharge-treated PET film or a BT-144 treated steel plate with an applicator so that the film thickness was 37 ⁇ 2 ⁇ m, and set for 30 minutes. Subsequently, after drying the obtained coating film at 60 degreeC for 20 minutes, baking was performed at 140 degreeC for 20 minutes, and the test piece of each coating composition was produced. The test piece was evaluated as follows. The results are shown in Tables 4-1 to 4-3 and Table 5.
  • the coating composition using the pigment composition of the present invention has a sense of color depth, gloss, color development, water resistance, haze value and flip-flop. It was shown to be excellent in performance.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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Abstract

L'invention concerne une composition de pigment qui comprend un produit neutralisé d'un agent de dispersion comprenant un groupe acide (S) et d'un composé basique, un pigment et une eau. Ledit agent de dispersion comprenant un groupe acide (S) comprend quant à lui une résine décrite aux points (S1) ou (S2) suivants. (S1) Une résine qui consiste en un produit réactionnel entre un groupe hydroxyle d'un polymère (A) possédant un groupe hydroxyle et un groupe acide, et un groupe anhydride d'acide d'un anhydride d'acide tricarboxylique et/ou d'un di-anhydride d'acide tétracarboxylique. (S2) Une résine qui consiste en un polymère obtenu par polymérisation d'un monomère éthyléniquement insaturé (C) contenant un monomère éthyléniquement insaturé à teneur en groupe acide (c1), en présence d'un produit réactionnel entre un groupe hydroxyle d'un composé (B) possédant un groupe hydroxyle, et un groupe anhydride d'acide d'un anhydride d'acide tricarboxylique et/ou d'un di-anhydride d'acide tétracarboxylique.
PCT/JP2017/029049 2016-08-10 2017-08-10 Composition de pigment, matériau de revêtement contenant cette composition de pigment, et agent de dispersion Ceased WO2018030506A1 (fr)

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
JP2020084100A (ja) * 2018-11-29 2020-06-04 東洋インキＳｃホールディングス株式会社 （メタ）アクリレート重合体の製造方法、（メタ）アクリレート重合体、ブロック共重合体、およびグラフト共重合体
JPWO2022019255A1 (fr) * 2020-07-22 2022-01-27

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JP2000319571A (ja) * 1998-11-09 2000-11-21 Toyo Ink Mfg Co Ltd 水性顔料分散体およびそれを用いたインクジェットインキ
JP2001064562A (ja) * 1999-08-27 2001-03-13 Nippon Paint Co Ltd 水性顔料分散液の分散安定性改良方法
WO2008007776A1 (fr) * 2006-07-14 2008-01-17 Toyo Ink Manufacturing Co., Ltd. Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant
JP2008029901A (ja) * 2005-07-08 2008-02-14 Toyo Ink Mfg Co Ltd 分散剤、その製造方法、及び該分散剤を含む顔料分散体
JP2010185934A (ja) * 2009-02-10 2010-08-26 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物及びカラーフィルタ
JP2012036379A (ja) * 2010-07-14 2012-02-23 Toyo Ink Sc Holdings Co Ltd 顔料用分散剤、及びそれを用いた顔料組成物

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JPH0931360A (ja) * 1995-07-21 1997-02-04 Dainippon Ink & Chem Inc 水性顔料分散体の製造方法、および該水性顔料分散体を含有する水性着色剤組成物
JP2000319571A (ja) * 1998-11-09 2000-11-21 Toyo Ink Mfg Co Ltd 水性顔料分散体およびそれを用いたインクジェットインキ
JP2000239376A (ja) * 1999-02-19 2000-09-05 Dainippon Toryo Co Ltd 水性塗料用顔料分散剤の製造方法
JP2001064562A (ja) * 1999-08-27 2001-03-13 Nippon Paint Co Ltd 水性顔料分散液の分散安定性改良方法
JP2008029901A (ja) * 2005-07-08 2008-02-14 Toyo Ink Mfg Co Ltd 分散剤、その製造方法、及び該分散剤を含む顔料分散体
WO2008007776A1 (fr) * 2006-07-14 2008-01-17 Toyo Ink Manufacturing Co., Ltd. Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant
JP2010185934A (ja) * 2009-02-10 2010-08-26 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物及びカラーフィルタ
JP2012036379A (ja) * 2010-07-14 2012-02-23 Toyo Ink Sc Holdings Co Ltd 顔料用分散剤、及びそれを用いた顔料組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020084100A (ja) * 2018-11-29 2020-06-04 東洋インキＳｃホールディングス株式会社 （メタ）アクリレート重合体の製造方法、（メタ）アクリレート重合体、ブロック共重合体、およびグラフト共重合体
JPWO2022019255A1 (fr) * 2020-07-22 2022-01-27
WO2022019255A1 (fr) * 2020-07-22 2022-01-27 富士フイルム株式会社 Composition de résine, film, filtre optique, élément d'imagerie à l'état solide, dispositif d'affichage d'images et résine
JP7397201B2 (ja) 2020-07-22 2023-12-12 富士フイルム株式会社 樹脂組成物、膜、光学フィルタ、固体撮像素子、画像表示装置及び樹脂

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