WO2022163449A1 - Composition de résine colorée, film coloré et substrat décoratif - Google Patents

Composition de résine colorée, film coloré et substrat décoratif Download PDF

Info

Publication number
WO2022163449A1
WO2022163449A1 PCT/JP2022/001701 JP2022001701W WO2022163449A1 WO 2022163449 A1 WO2022163449 A1 WO 2022163449A1 JP 2022001701 W JP2022001701 W JP 2022001701W WO 2022163449 A1 WO2022163449 A1 WO 2022163449A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
mass
colored
colored resin
group
Prior art date
Application number
PCT/JP2022/001701
Other languages
English (en)
Japanese (ja)
Inventor
南部和樹
井上欣彦
Original Assignee
東レ株式会社
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
Application filed by 東レ株式会社 filed Critical 東レ株式会社
Priority to CN202280007802.8A priority Critical patent/CN116568762A/zh
Priority to KR1020237024062A priority patent/KR20230136739A/ko
Priority to JP2022504576A priority patent/JPWO2022163449A1/ja
Publication of WO2022163449A1 publication Critical patent/WO2022163449A1/fr

Links

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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/22—Monoazo compounds containing other metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B7/00—Indigoid 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
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to colored resin compositions, colored films, and decorative substrates.
  • Touch panels in various information terminals such as smartphones and in-vehicle displays have a light-shielding film formed in the non-display area of the cover lens, which is located on the outermost layer when viewed from the user side, and the light-shielding film hides electrodes such as the lead-out wiring of the touch sensor. have a role to play.
  • In-vehicle displays and smartwatches require reliability such that operability and design do not change even under ultraviolet irradiation of sunlight or in high temperature and high humidity environments. It is required that it does not decrease.
  • Patent Document 1 discusses an inkjet printing ink containing a carboxyl group-containing binder polymer having a weight average molecular weight of 20,000 to 300,000 and a curing agent containing a blocked isocyanate and an epoxy resin.
  • Patent Document 2 as an ink that can be printed on a non-heat-resistant, non-absorbent medium and that can be cured at a low temperature, an acrylic resin containing a glycol ether-based solvent and an acetate solvent and having a hydroxyl group and a low-temperature Ink jet printing inks containing dissociated blocked isocyanates have been investigated.
  • the ink described in Patent Document 1 can maintain high adhesion even after various reliability tests by using both a blocked isocyanate and an epoxy resin. Therefore, when used for long-term printing, the film thickness and printing accuracy change, resulting in insufficient viscosity stability.
  • the ink described in Patent Document 2 can be cured at a low temperature and has excellent viscosity stability. It lacked features.
  • the object of the present invention is to provide a colored resin composition that can be cured at a low temperature, has excellent viscosity stability at room temperature, and maintains high adhesion even after a light resistance test and a high temperature and high humidity test.
  • a colored resin composition contains a hydroxyl- or acid-containing resin, a coloring agent, a dispersant, and a blocked isocyanate, and an acrylic dispersant having a basic group as a dispersant.
  • the inventors have found that the above problems can be solved by applying the method, and completed the present invention.
  • the object of the present invention is mainly achieved by the following configurations.
  • the colored resin composition of the present invention can be cured at a low temperature and has excellent viscosity stability at room temperature, so that a colored film that maintains high adhesion even after a light resistance test and a high temperature and high humidity test can be obtained.
  • the colored resin composition of the present invention contains (A) a hydroxyl group- or acid group-containing resin, (B) a coloring agent, (C) a dispersant, and (D) a blocked isocyanate.
  • A The hydroxyl group- or acid group-containing resin acts as a binder in the composition.
  • B The coloring agent has the effect of shielding visible light.
  • C The dispersing agent has the function of dispersing the coloring material uniformly and preventing reaggregation.
  • the blocked isocyanate has the action of reacting with hydroxyl groups or acid groups contained in the resin only during heating and baking.
  • the present invention is characterized in that the (C) dispersant is an acrylic dispersant having a basic group.
  • Acrylic dispersants are excellent in reliability such as light resistance and high temperature and high humidity resistance. Furthermore, since the dispersant has a basic group, the dispersant adsorbs to the surface of the coloring agent, finely disperses the coloring agent when dispersing the coloring agent, stabilizes the dispersion state due to steric hindrance between the dispersing agents, and increases over time. It has the effect of suppressing stickiness and reaggregation.
  • (D) blocked isocyanate does not have reactivity due to the function of the blocking agent at room temperature, and has reactivity only when heated, so that the viscosity stability of the colored resin composition can be maintained well, and the blocking agent is used.
  • the blocking agent can dissociate at low temperatures and react with hydroxyl groups or acid groups.
  • a hydroxyl- or acid-group-containing resin is a resin having a hydroxyl group or an acid group.
  • hydroxyl group- or acid group-containing resins include acrylic resins, cardo resins, siloxane resins, polyimide resins, polyimide precursors, polyurethane resins, polyester resins, and vinyl chloride resins. You may contain 2 or more types of these. Among these, acrylic resins, polyurethane resins and polyester resins are preferred, and acrylic resins are particularly preferred, from the viewpoint of storage stability of the colored resin composition and adhesion and reliability of the colored film.
  • the hydroxyl or acid group-containing resin has a hydroxyl value or acid value of 10 mgKOH/g or more, and the viscosity stability of the colored resin composition, the curing speed, the adhesion of the colored film, and the reliability of the colored film is preferable from the viewpoint of
  • the hydroxyl value is preferably 20-300 mgKOH/g, more preferably 90-250 mgKOH/g.
  • the acid value is preferably 20-300 mgKOH/g, more preferably 60-150 mgKOH/g.
  • the sum of acid value and hydroxyl value is preferably 80-300 mgKOH/g, more preferably 100-300 mgKOH/g.
  • the total acid value and hydroxyl value is less than 80 mgKOH/g, the number of functional groups that react with (D) the blocked isocyanate is reduced, resulting in a decrease in curing speed, adhesion of the colored film, and deterioration in adhesion after various reliability tests. is concerned.
  • the total of the acid value and the hydroxyl value is less than 80 mgKOH/g, a decrease in viscosity stability and an increase in the diffuse reflectance of the resulting colored film are observed.
  • the decrease in viscosity stability and the increase in the diffuse reflectance of the colored film are caused by deterioration in compatibility between (A) the hydroxyl- or acid-containing resin and (D) the blocked isocyanate. It is thought to be caused to inhibit dispersion.
  • the diffuse reflectance is preferably low from the viewpoint of design.
  • the hydroxyl value refers to the number of mg of potassium hydroxide required to neutralize the acetic acid bound to the hydroxyl group when 1 g of (A) the hydroxyl- or acid-containing resin is acetylated (unit :mg KOH/g).
  • the acid value refers to the number of mg of potassium hydroxide required to neutralize 1 g of (A) a hydroxyl group- or acid group-containing resin according to JIS K0070 (1992) (unit: mgKOH/g).
  • the weight average molecular weight (Mw) of the hydroxyl group- or acid group-containing resin is preferably 500 or more and 150,000 or less. From the viewpoint of the reliability of the colored film, the weight average molecular weight is preferably 5,000 or more and 150,000 or less, more preferably 10,000 or more and 150,000 or less.
  • the weight average molecular weight (Mw) refers to a value analyzed by gel permeation chromatography using tetrahydrofuran as a carrier and converted using a standard polystyrene calibration curve.
  • Examples of the hydroxyl group or acid group possessed by the hydroxyl group- or acid group-containing resin include a hydroxyl group, a carboxyl group, a carboxylic anhydride group, a sulfonic acid group, and a phosphoric acid group. You may contain 2 or more types of these. Among these, a hydroxy group or a carboxyl group is particularly preferable from the viewpoint of adhesion after a reliability test of the coating film and low-temperature curability.
  • the content of the hydroxyl group- or acid group-containing resin is the total solid content of 100 mass from the viewpoint of the storage stability of the pigment dispersion, the curability of the colored resin composition, and the adhesion of the resulting colored film to the substrate. %, preferably 10 to 99% by mass, more preferably 25 to 85% by mass.
  • the solid content is a component other than the solvent among the components contained in the composition.
  • the solid content includes (A) hydroxyl group- or acid group-containing resin, (B) colorant, (C) dispersant, (D) blocked isocyanate, and other additives.
  • the curability of the colored resin composition and the adhesion of the colored film to the substrate are also affected by the content of (D) blocked isocyanate, which will be described later.
  • Colorants include, for example, organic pigments, inorganic pigments, and dyes.
  • Organic pigments or inorganic pigments are preferred in order to improve the heat resistance, reliability and light resistance of the colored film.
  • organic pigments include diketopyrrolopyrrole pigments; azo pigments such as azo, disazo and polyazo; phthalocyanine pigments such as copper phthalocyanine, halogenated copper phthalocyanine and metal-free phthalocyanine; Anthraquinone pigments such as pyrimidine, flavanthrone, anthanthrone, indanthrone, pyranthrone, and violanthrone; quinacridone pigments; dioxazine pigments; perinone pigments; perylene pigments; quinophthalone-based pigments; threne-based pigments; and metal complex-based pigments.
  • diketopyrrolopyrrole pigments such as azo, disazo and polyazo
  • phthalocyanine pigments such as copper phthalocyanine, halogenated copper phthalocyanine and metal-free phthalocyanine
  • Anthraquinone pigments such as pyrimidine, flavanthron
  • inorganic pigments include titanium oxide, zinc white, zinc sulfide, lead white, calcium carbonate, precipitated barium sulfate, white carbon, alumina white, kaolin clay, talc, bentonite, black iron oxide, cadmium red, red iron oxide, molybdenum. Red, molybdate orange, chrome vermillion, yellow lead, cadmium yellow, yellow iron oxide, titanium yellow, chromium oxide, Viridian, titanium cobalt green, cobalt green, cobalt chrome green, victoria green, ultramarine blue, dark blue, cobalt blue, cerulean blue, cobalt silica blue, cobalt zinc silica blue, manganese violet, cobalt violet, and the like.
  • Dyes include, for example, azo dyes, anthraquinone dyes, condensed polycyclic aromatic carbonyl dyes, indigoid dyes, carbonium dyes, phthalocyanine dyes, methine dyes, and polymethine dyes.
  • black coloring materials include black organic pigments, mixed color organic pigments, and inorganic pigments.
  • black organic pigments include carbon black, perylene black, aniline black, and benzofuranone pigments.
  • mixed-color organic pigments include pseudo-black pigments obtained by mixing two or more pigments having colors such as red, blue, green, purple, yellow, magenta, and cyan.
  • black inorganic pigments include graphite; fine particles of metals such as titanium, copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, and silver; oxides, composite oxides, sulfides, and nitrides of the above metals. , oxynitrides, and the like.
  • white coloring materials include titanium dioxide, barium carbonate, zirconium oxide, calcium carbonate, barium sulfate, alumina white, and silicon dioxide.
  • Two or more of these coloring materials may be contained.
  • the (B) colorant in the colored resin composition of the present invention is preferably finely dispersed and the dispersion is stabilized. If the coloring material is not sufficiently dispersed, the resulting colored film contains coarse particles of the coloring material, resulting in unevenness in the film. It is considered to be a factor to
  • the average particle size of the coloring material in the colored resin composition is preferably 30 to 200 nm, more preferably 30 to 120 nm.
  • an acrylic dispersant having a basic group is used as the dispersant, and the colorant is dispersed stably and uniformly in a fine state without reaggregating the colorant in the resin.
  • a method of finely dispersing a coloring agent by a salt milling method or the like, or a method of finely dispersing the coloring agent by a bead mill, which will be described later, can be used to produce a colored resin composition.
  • the content of the (B) colorant in the colored resin composition of the present invention is preferably 1 to 60% by mass with respect to 100% by mass of the total solid content.
  • the content of the coloring agent (B) is preferably 1 part by mass or more, the resulting colored film can be improved in its ability to block visible light.
  • the coloring material is a component that does not shrink during curing, the more the coloring material, the less the film stress and the better the adhesion. From this point of view, the content of the coloring material is more preferably 13% by mass or more.
  • the content of the coloring agent (B) is preferably 60% by mass or less, more preferably 48% by mass or less.
  • the dispersant in the colored resin composition of the present invention is an acrylic dispersant having a basic group.
  • a dispersant is a substance having both a colorant affinity group having chemical bonding or adsorption action to the colorant surface and a polymer chain or group having solvent affinity.
  • An acrylic dispersant refers to a dispersant having a main chain obtained by copolymerizing a monomer containing a (meth)acrylic group.
  • the main chain may be a block copolymer or a random copolymer, or may have a side chain such as a graft copolymer.
  • the dispersant improves the wettability of the colorant to the dispersion medium in the dispersion treatment described later, promotes disaggregation of the colorant, and stabilizes the particle size and viscosity of the colorant by steric hindrance and/or electrostatic repulsion effects. Furthermore, it has the effect of suppressing the occurrence of color separation during storage or coating of the colored resin composition.
  • the (C) dispersant in the colored resin composition of the present invention an acrylic resin with excellent reliability such as light resistance and high temperature and high humidity resistance is selected. Furthermore, since the dispersant (C) has a basic group, the dispersant adsorbs to the surface of the colorant, finely disperses the colorant when the colorant is dispersed, and stabilizes the dispersed state due to steric hindrance between the dispersants. , has the effect of suppressing thickening and reaggregation over time.
  • Examples of basic groups include primary amino groups, secondary amino groups, tertiary amino groups, quaternary ammonium bases, amide groups, imino groups, imidazoline groups, pyrrole groups, imidazole groups, benzimidazole groups, pyrazole groups, A pyridine group, a pyrimidine group, a pyrazine group, a pyrrolidine group, a piperidine group, a piperazine group, an indole group, an indoline group, a purine group, a quinoline group, an isoquinoline group, a quinuclidine group, a triazine group, and the like.
  • the dispersant can have one or more of these basic groups.
  • a dispersant containing at least one of a tertiary amino group and a quaternary ammonium base is preferable because it has good adsorptive power to a coloring material and high dispersibility. Dispersants with both ammonium bases are particularly preferred. If the adsorption power to the coloring material is good, the amount of dispersant released into the colored film by desorption from the coloring material will decrease during the high-temperature, high-humidity test and light resistance test. It is considered that the adhesion of the colored film after the wet test is improved.
  • the amine value of the dispersant (C) is preferably 1 mgKOH/g or more and 200 mgKOH/g or less, more preferably 20 mgKOH/g or more and 150 mgKOH/g or less.
  • the weight average molecular weight (Mw) is preferably 500 or more and 150,000 or less, more preferably 5000 or more and 150,000 or less.
  • the amine value in the present invention represents the number of mg of KOH equivalent to the acid required to neutralize 1 g of the dispersant.
  • acrylic dispersants having a basic group examples include DISPERBYK (registered trademark)-112, 116, 151, 155, 156, 187, 190, 191, 194N, 199, 2000, 2001, 2006, 2008, 2009, 2010, 2012, 2013, 2015, 2020, 2022, 2025, 2050, 2055, 2070, DISPERBYK (registered trademark) LPN6919, LPN21116, LPN22102 (all manufactured by BYK-Chemie).
  • DISPERBYK registered trademark
  • LPN6919, LPN21116, LPN22102 all manufactured by BYK-Chemie.
  • acrylic dispersants containing at least one of a tertiary amino group and a quaternary ammonium base include, for example, DISPERBYK (registered trademark)-187, 190, 191, 194N, 199, 2000, 2001, 2006 , 2009, 2010, 2012, 2013, 2015, 2022, 2025, 2050, 2055, DISPERBYK® LPN6919, LPN21116, and acrylic dispersants having both a tertiary amine and a quaternary ammonium salt, For example, DISPERBYK® LPN21116 may be mentioned.
  • the content of (C) the dispersant is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, relative to 100 parts by mass of the coloring material (B).
  • the content of the dispersant is preferably 100 parts by mass or less, more preferably 60 parts by mass or less with respect to 100 parts by mass of the coloring agent, from the viewpoint of improving the adhesion and reliability of the colored film.
  • Blocked isocyanate is a compound having two or more isocyanate groups blocked by a blocking agent. Since the blocking agent is dissociated by heating to regenerate the isocyanate group, the blocked isocyanate has a long pot life and the ink containing it has excellent viscosity stability.
  • a blocked isocyanate is used as a curing agent in the colored resin composition of the present invention. The blocked isocyanate dissociates (deprotects) the blocking agent by heating at a relatively low temperature to regenerate the isocyanate group. The regenerated isocyanate group thermally reacts with the hydroxyl group or acid group of the hydroxyl group- or acid group-containing resin (A) to cure the ink.
  • the type of isocyanate is not particularly limited, but includes aromatic diisocyanates, aliphatic diisocyanates, alicyclic diisocyanates, dimers or trimers obtained by modifying diisocyanates, and compounds containing terminal isocyanate groups. These may be used alone or in combination.
  • aromatic diisocyanates include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane-4,4'-diisocyanate, diphenylmethane-2,4'-diisocyanate and dianisidine diisocyanate.
  • Aliphatic diisocyanates include, for example, 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate (hereinafter referred to as HMDI), 2,2,4-trimethyl-1,6-hexamethylene and diisocyanate.
  • HMDI 1,6-hexamethylene diisocyanate
  • diisocyanate examples include lysine diisocyanate, isophorone diisocyanate (hereinafter IPDI), 1,3-bis(isocyanatomethyl)-cyclohexane, 4,4'-dicyclohexylmethane diisocyanate and the like. Dimers or trimers by modification of these diisocyanates are also included.
  • Modification methods include biuret formation, isocyanurate formation, and the like.
  • a terminal isocyanate group-containing compound obtained by reacting the aforementioned diisocyanate compound or polyisocyanate compound with an active hydrogen compound such as ethylene glycol, propylene glycol, trimethylolpropane, ethanolamine, polyester polyol, polyether polyol, polyamide, etc. is mentioned.
  • Blocking agents include, for example, known blocking agents such as phenol, methyl ethyl ketoxime, and sodium bisulfite.
  • a resin such as a polycarbonate or a PET film
  • Examples of such blocking agents that can be dissociated at lower temperatures include active methylene compounds and pyrazole compounds.
  • Active methylene compounds include Meldrum's acid, dialkyl malonate, alkyl acetoacetate, 2-acetoacetoxyethyl methacrylate, acetylacetone, and ethyl cyanoacetate.
  • Pyrazole compounds include pyrazole, 3,5-dimethylpyrazole, 3-methylpyrazole, 4-benzyl-3,5-dimethylpyrazole, 4-nitro-3,5-dimethylpyrazole, 4-bromo-3,5-dimethyl pyrazole, 3-methyl-5-phenylpyrazole and the like. Among them, diethyl malonate, 3,5-dimethylpyrazole and the like are preferable.
  • “Blocked isocyanate” is available as a commercial product.
  • Coronate (registered trademark) AP Stable M Coronate (registered trademark) 2503, 2515, 2507, 2513, 2555, Millionate MS-50 (manufactured by Nippon Polyurethane Industry Co., Ltd.), Duranate (registered trademark) 17B- 60PX, 17B-60P, TPA-B80X, TPA-B80E, MF-B60X, MF-B60B, MF-K60X, MF-K60B, E402-B80B, SBN-70D, SBB-70P, K6000 (above, Asahi Kasei Chemicals ), Desmodur BL1100, BL1265 MPA/X, BL3575/1, BL3272MPA, BL3370MPA, BL3475BA/SN, BL5375MPA, VPLS2078/2, BL4265SN, PL340, PL350, Su
  • the contents of (A) a hydroxyl group- or acid group-containing resin and (D) a blocked isocyanate are preferably selected so that their respective functional groups are consumed after curing.
  • the content of (D) blocked isocyanate is preferably 1 to 300 parts by mass, more preferably 5 to 150 parts by mass, more preferably 10 to 100 parts by mass, with the mass of (A) hydroxyl group- or acid group-containing resin being 100 parts by mass. Part is more preferred.
  • the content of the blocked isocyanate is within these ranges, the effect of efficiently curing the hydroxyl group- or acid group-containing resin can be obtained.
  • the colored resin composition of the present invention preferably further contains (E) an organic solvent because it can improve the applicability.
  • the organic solvent has the effect of uniformly dissolving or dispersing (A) the hydroxyl group- or acid group-containing resin, (B) the coloring agent, (C) the dispersant, and (D) the blocked isocyanate.
  • As the organic solvent a compound having a boiling point of 110 to 250° C. under atmospheric pressure is preferable.
  • the colored resin composition of the present invention is assumed to be applied by a printing method such as spin coater, slit coater, screen printing, inkjet, gravure printing or bar coater, if the boiling point is less than 110 ° C., the drying of the organic solvent The speed is high, and problems with coating uniformity are likely to occur. On the other hand, if the boiling point exceeds 250° C., the organic solvent may remain in the resulting colored film and the chemical resistance of the colored film may deteriorate.
  • a printing method such as spin coater, slit coater, screen printing, inkjet, gravure printing or bar coater
  • Organic solvents include, for example, ethers, acetates, esters, ketones, aromatic hydrocarbons, amides, and alcohols.
  • ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl.
  • Acetates include, for example, butyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether.
  • esters include lactic acid alkyl esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate and 3-methoxypropionic acid; ethyl, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, n-butyl propionate , ethyl
  • ketones include methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone and the like.
  • aromatic hydrocarbons include toluene and xylene.
  • Amides include, for example, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and the like.
  • alcohols include butyl alcohol, isobutyl alcohol, pentanol, 4-methyl-2-pentanol, 3-methyl-2-butanol, 3-methyl-3-methoxybutanol, diacetone alcohol and the like. be done. You may contain 2 or more types of these.
  • the content of acetates in the organic solvent is preferably 50 to 100% by mass, more preferably 70 to 100% by mass.
  • the organic solvent (E) preferably contains 3 to 90% by mass, more preferably 10 to 75% by mass, of an organic solvent having a boiling point of 150 to 250°C.
  • the content of the (E) organic solvent is preferably 50% by mass or more of the entire composition from the viewpoint of uniformity of the coating film thickness in the coating step, and more preferably 70% by mass or more. preferable.
  • the content of the (E) organic solvent is preferably 95% by mass or less, more preferably 90% by mass or less, of the entire composition from the viewpoint of suppressing pigment sedimentation.
  • the colored resin composition of the present invention may contain a leveling agent.
  • a leveling agent By containing a leveling agent, the coatability and the surface smoothness of the colored film can be improved.
  • leveling agents include anionic surfactants such as ammonium lauryl sulfate and triethanolamine polyoxyethylene alkyl ether sulfate; cationic surfactants such as stearylamine acetate and lauryltrimethylammonium chloride; Amphoteric surfactants such as methylhydroxyethylimidazolium betaine; Nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and sorbitan monostearate; Silicone surfactants having a main skeleton such as polydimethylsiloxane agents; fluorine-based surfactants, and the like. You may contain 2 or more types of these. Examples of commercially available surfactants include "BYK (registered trademark)"-302, 333, 3550
  • a dispersion machine is used to contain (A) a hydroxyl group- or acid group-containing resin, (B) a coloring agent, (C) a dispersant and (E) an organic solvent.
  • a coloring agent dispersion having a high coloring agent concentration is prepared in advance, and (A) a hydroxyl group- or acid group-containing resin, (D) a blocked isocyanate, and, if necessary, an interface
  • a method of adding other ingredients such as an activator and stirring is preferred. Filtration of the obtained colored resin composition may be performed as necessary.
  • Dispersers used for dispersion treatment include, for example, ball mills, bead mills, sand grinders, three-roll mills, and high-speed impact mills.
  • a bead mill is preferable for improving dispersion efficiency and fine dispersion.
  • examples of bead mills include coball mills, basket mills, pin mills, and dyno mills.
  • Bead mill beads include, for example, titania beads, zirconia beads, and zircon beads.
  • the method for producing the colored resin composition of the present invention it is preferable to perform dispersion treatment in multiple stages using a bead mill.
  • a bead mill For example, it is preferable to disperse with a bead mill using beads having an average bead diameter of more than 0.1 mm ⁇ , and then to disperse with a bead mill using beads having an average bead diameter of 0.1 mm ⁇ or less.
  • a coloring material having a large crystallite size can be efficiently pulverized by dispersing with a bead mill using beads having an average bead diameter larger than 0.1 mm ⁇ .
  • the bead mill is preferably provided with a centrifugal separator capable of separating fine beads from the dispersion liquid.
  • the average bead diameter refers to the number average value of equivalent circle diameters of beads.
  • the beads were photographed at a magnification of 45 times with a stereoscopic microscope, and the longest and shortest diameters of 100 randomly selected beads were measured, and the average value was taken as the circle equivalent diameter, and the number average By calculating the value, the bead diameter can be obtained.
  • a colored film can be obtained by curing the colored resin composition of the present invention.
  • the light shielding property of the colored film formed in the non-display area of the display is preferably 4.0 or more OD, more preferably 4.5 or more, from the viewpoint of preventing light leakage from the backlight.
  • a decorative substrate comprising a substrate and a colored film is obtained by coating a colored resin composition on a substrate and curing it to form a colored film by the following method.
  • substrates include transparent glass substrates such as soda glass, non-alkali glass, and aluminosilicate glass; resin substrates such as polycarbonate resin and acrylic resin; film substrates such as PET film and COP film; silicon wafers, ceramics, and gallium arsenide. and the like.
  • coating methods include spin coating using a spinner, spray coating, die coating, roll coating, inkjet printing, screen printing, and gravure printing.
  • the film thickness of the coating film can be appropriately selected depending on the coating method or the like.
  • the film thickness after drying is generally 1 to 150 ⁇ m.
  • the obtained coating film is dried to obtain a dry film.
  • the drying method include heat drying, air drying, reduced pressure drying, and infrared irradiation.
  • heat drying devices include ovens and hot plates.
  • the drying temperature is preferably 50 to 150° C., and the drying time is preferably 1 minute to several hours. This drying process is expected to level the coating film and suppress the adhesion of foreign substances. However, this drying process is not necessarily required, and a colored film can be obtained only by the heat treatment described later.
  • the resulting coating film is cured by heat treatment (post-baking) to obtain a colored film.
  • the heat treatment may be performed in air, in a nitrogen atmosphere, or in a vacuum.
  • the heating temperature is preferably 70 to 300°C, more preferably 80 to 180°C.
  • the heating temperature can be selected according to the heat resistance temperature of the base material.
  • the heating time is preferably 0.25 to 5 hours. During the heat treatment, the heating temperature may be changed continuously or stepwise.
  • a decorative substrate comprising a substrate and a colored film made of a cured product of the colored resin composition of the present invention is a decorative substrate in display terminals such as smartphones, tablet PCs, and in-vehicle displays, and is used for driver monitoring in in-vehicle displays and in-vehicle instruments. It can be suitably used for a near-infrared sensor for a gesture sensor, a decorative substrate for concealing a near-infrared camera, a decorative film for concealing a LiDAR sensor, and the like.
  • the colored film made of the cured product of the colored resin composition of the present invention can be suitably used as a light-shielding film such as a black matrix of a color filter provided in a liquid crystal display device or the like, a colored partition wall inside an organic EL display, and the like.
  • JIS S6050 acceptable product JIS S6050 acceptable product
  • the tape While holding one end of the tape and keeping the tape perpendicular to the plate, the tape was momentarily peeled from the colored film. At this time, the ratio of the peeled colored film was evaluated by visually confirming the number of squares of the colored film remaining without peeling from the substrate among the 100 squares of the colored film.
  • [Average particle size of coloring material] Set the temperature of a dynamic light scattering particle size distribution meter (UPA-EX150 manufactured by Microtrac Bell Co., Ltd.) to 20 ⁇ 1 ° C., and dilute the coloring material dispersion or colored resin composition 400 times with propylene glycol monomethyl ether acetate. The measured value (D50) obtained by measuring the colorant particles was used as the value of the average particle size of the coloring material particles.
  • UPA-EX150 dynamic light scattering particle size distribution meter
  • the colored films obtained in Examples and Comparative Examples were measured using a spectrophotometer (CM-2600d; manufactured by Konica Minolta, Inc.) calibrated with a white calibration plate (CM-A145; manufactured by Konica Minolta, Inc.).
  • CM-2600d color temperature 6504K
  • viewing angle 2° CIE1976
  • atmospheric pressure 20°C
  • SCE diffuse reflection chromaticity
  • L * was evaluated as an index of the diffuse reflectance of the colored film.
  • the colored film formed in the non-display area of the cover lens preferably has a low L * from the viewpoint of design.
  • the film thickness of the colored film obtained in each example and comparative example was measured using a contact film thickness gauge Surfcom 1400D (manufactured by Tokyo Seimitsu Co., Ltd.).
  • a white cotton cloth Koreanakin No. 3
  • isopropyl alcohol a test solvent, as a friction element, layered so as to come into contact with the colored film
  • a Gakushin type rubbing tester under a constant load condition ( After performing a rubbing test (10 reciprocations) at 300 g/cm 2 ), the film thickness was measured again. From the changes in the thickness of the colored film before and after the rubbing test, the solvent resistance of the colored film was obtained from the following formula.
  • Solvent resistance (%) film thickness after rubbing test ( ⁇ m) ⁇ 100/film thickness before rubbing test ( ⁇ m) Evaluation of solvent resistance is performed to quantitatively evaluate the degree of curability during low-temperature baking.
  • the hydroxyl value of the resin was measured in mg of potassium hydroxide required to neutralize the acetic acid bound to the hydroxyl group when 1 g of the resin was acetylated according to JIS K0070 (1992).
  • the number of mg of potassium hydroxide required to neutralize 1 g of the resin was measured according to JIS K0070 (1992).
  • the weight average molecular weight was measured by polystyrene conversion using gel permeation chromatography (GPC) "HLC-8220GPC" (manufactured by Tosoh Corporation) using tetrahydrofuran as the carrier.
  • the resulting preliminary dispersion was supplied to a dispersing machine Ultra Apex Mill UAM015 manufactured by Kotobuki Kogyo Co., Ltd. equipped with a centrifugal separator filled with 75% by volume of zirconia beads having a bead diameter of 0.30 mm ⁇ , and was rotated at a rotation speed of 9 m / s. Dispersion was carried out for 20 minutes.
  • the liquid after the dispersion treatment was supplied to an Ultra Apex Mill UAM015 filled with 75% by volume of zirconia beads having a bead diameter of 0.05 mm ⁇ , and dispersed at a rotation speed of 11 m/s for 90 minutes to obtain a solid concentration of 25% by mass.
  • a coloring agent dispersion DP-1 having a coloring agent/(resin+dispersant) (mass ratio) of 70/30 was obtained.
  • the mixture was stirred for 20 minutes with a mixer to obtain a preliminary dispersion.
  • the resulting preliminary dispersion was supplied to a dispersing machine Ultra Apex Mill UAM015 manufactured by Kotobuki Kogyo Co., Ltd. equipped with a centrifugal separator filled with 75% by volume of zirconia beads having a bead diameter of 0.30 mm ⁇ , and was rotated at a rotation speed of 9 m / s. Dispersion was carried out for 20 minutes.
  • the liquid after the dispersion treatment was supplied to an Ultra Apex Mill UAM015 filled with 75% by volume of zirconia beads having a bead diameter of 0.05 mm ⁇ , and dispersed at a rotation speed of 11 m/s for 90 minutes to obtain a solid concentration of 25% by mass. , to obtain a coloring agent dispersion DP-2 having a coloring agent/(resin+dispersant) (mass ratio) of 70/30.
  • the resulting preliminary dispersion was supplied to a dispersing machine Ultra Apex Mill UAM015 manufactured by Kotobuki Kogyo Co., Ltd. equipped with a centrifugal separator filled with 75% by volume of zirconia beads having a bead diameter of 0.50 mm ⁇ , and was rotated at a rotation speed of 12 m / s. Dispersion was carried out for 20 minutes. Subsequently, the liquid after the dispersion treatment was supplied to an Ultra Apex Mill UAM015 filled with 75% by volume of zirconia beads having a bead diameter of 0.05 mm ⁇ , and dispersed at a rotation speed of 8 m/s for 90 minutes until the solid content was 20% by mass. , to obtain a coloring agent dispersion DP-3 having a coloring agent/(resin+dispersant) (mass ratio) of 60/40.
  • the mixture was stirred for a minute to obtain a preliminary dispersion.
  • the obtained preliminary dispersion is supplied to a paint shaker (Toyo Seiki Seisakusho Co., Ltd.), dispersed for 3 hours using zirconia beads with a bead diameter of 1.0 mm ⁇ , and then filtered through a 5 ⁇ m filter to obtain a solid content concentration of 20.
  • the resulting preliminary dispersion was supplied to a dispersing machine Ultra Apex Mill UAM015 manufactured by Kotobuki Kogyo Co., Ltd. equipped with a centrifugal separator filled with 75% by volume of zirconia beads having a bead diameter of 0.30 mm ⁇ , and was rotated at a rotation speed of 9 m / s. Dispersion was carried out for 20 minutes. Subsequently, the liquid after the dispersion treatment was supplied to an Ultra Apex Mill UAM015 filled with 75% by volume of zirconia beads having a bead diameter of 0.05 mm ⁇ , and dispersed at a rotation speed of 11 m/s for 90 minutes to obtain a solid concentration of 25% by mass. , to obtain a coloring agent dispersion DP-8 having a coloring agent/(resin+dispersant) (mass ratio) of 70/30. Table 2 shows the compositions, dispersing conditions and conditions of Production Examples 5 to 12.
  • Example 1 To 31.43 g of the colorant dispersion (DP-1), 26.56 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and a blocked isocyanate whose blocking agent is an oxime-based blocking agent, coronate ( Registered trademark) BI-301 (manufactured by Tosoh Corporation, Solvesso (registered trademark) 100 (manufactured by Exxon Chemical Co., Ltd.) 75% by mass solution) is 6.43 g, and a silicone surfactant "BYK (registered trademark)" is used as a surfactant.
  • a silicone surfactant "BYK (registered trademark)" is used as a surfactant.
  • the resulting colored resin composition PC-1 is placed on an easy-adhesive layer of a polyester film (manufactured by Toray Industries, Inc., Lumirror (registered trademark) U48, film thickness: 100 ⁇ m), and a spinner (1H- DS) to form a coating film.
  • the coated film was dried by heating in an oven at 90° C. for 30 minutes to obtain a colored film C-1.
  • Table 4 shows the results of evaluating this colored film C-1 by the method described above.
  • Example 2 A colored resin composition PC-2 was obtained in the same manner as in Example 1 except that the coloring agent dispersion (DP-2) was used instead of the coloring agent dispersion (DP-1). The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-2. Table 4 shows the results.
  • Example 3 To 31.43 g of the colorant dispersion (DP-2), 26.56 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( Registered trademark) SBB-70P (manufactured by Asahi Kasei Corporation, PGMEA 70% by mass solution) 6.89 g, and a silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie) as a surfactant as a PGMEA 10% solution A solution of 0.20 g dissolved in 34.91 g of PGMEA was added to obtain a colored resin composition having a total solid concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solid content PC- got 3. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-3. Table 4 shows the results.
  • Example 4 To 31.43 g of the colorant dispersion (DP-2), 26.56 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate (registered trademark), which is an active methylene blocking agent, is used as a blocking agent.
  • DP-2 colorant dispersion
  • P-1 hydroxyl group- or acid group-containing resin
  • Duranate registered trademark
  • Example 5 A colored resin composition PC-5 was obtained in the same manner as in Example 3, except that the hydroxyl- or acid-containing resin (P-2) was used instead of the hydroxyl- or acid-containing resin (P-1). The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-5. Table 4 shows the results.
  • Example 6 22.92 g of the colorant dispersion (DP-3), 16.04 g of the colorant dispersion (DP-4), and 6.88 g of the colorant dispersion (DP-5) were added with a hydroxyl- or acid-containing resin.
  • Example 7 To 45.83 g of the colorant dispersion (DP-6), 23.27 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 6.67 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 24.03 g of PGMEA was added to obtain a colored resin composition PC-7 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-7. Table 4 shows the results.
  • Example 8 A colored resin composition PC-8 was obtained in the same manner as in Example 3 except that the coloring agent dispersion (DP-7) was used instead of the coloring agent dispersion (DP-2). The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-8. Table 4 shows the results.
  • Example 9 To 18.86 g of the colorant dispersion (DP-2), 33.52 g of a 35% by mass solution of PGMEA of the hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 7.90 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Corporation), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 39.52 g of PGMEA was added to obtain a colored resin composition PC-9 having a total solids concentration of 22% by mass and a coloring material content of 15 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-9. Table 4 shows the results.
  • Example 10 To 56.57 g of the colorant dispersion (DP-2), 12.64 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 4.87 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Corporation), and 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 25.71 g of PGMEA was added to obtain a colored resin composition PC-10 having a total solids concentration of 22% by mass and a coloring material content of 45 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-10. Table 4 shows the results.
  • Example 11 To 12.57 g of the coloring material dispersion (DP-2), 37.00 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 8.41 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Corporation), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Corporation) as a surfactant, A solution dissolved in 41.82 g of PGMEA was added to obtain a colored resin composition PC-11 having a total solids concentration of 22% by mass and a coloring material content of 10 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-11. Table 4 shows the results.
  • Example 12 To 62.86 g of the colorant dispersion (DP-2), 9.16 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 4.37 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Corporation), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 23.41 g of PGMEA was added to obtain a colored resin composition PC-12 having a total solids concentration of 22% by mass and a coloring material content of 50 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-12. Table 4 shows the results.
  • Example 13 To 31.43 g of the colorant dispersion (DP-2), 17.37 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 11.49 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK Chemie) as a surfactant, A solution dissolved in 39.51 g of PGMEA was added to obtain a colored resin composition PC-13 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-13. Table 4 shows the results.
  • Example 14 To 31.43 g of the colorant dispersion (DP-2), 35.75 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-1), and Duranate ( 2.30 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 30.32 g of PGMEA was added to obtain a colored resin composition PC-14 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-14. Table 4 shows the results.
  • Example 15 To 31.43 g of the colorant dispersion (DP-2), 35.75 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-3), and Duranate ( 2.30 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 30.32 g of PGMEA was added to obtain a colored resin composition PC-15 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids.
  • Example 16 To 31.43 g of the colorant dispersion (DP-2), 35.75 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-4), and Duranate ( 2.30 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 30.32 g of PGMEA was added to obtain a colored resin composition PC-16 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids.
  • Example 17 To 31.43 g of the colorant dispersion (DP-2), 35.75 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-5), and Duranate ( 2.30 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 30.32 g of PGMEA was added to obtain a colored resin composition PC-17 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids.
  • Example 18 To 31.43 g of the colorant dispersion (DP-2), 35.75 g of a 35% by mass solution of PGMEA of a hydroxyl group- or acid group-containing resin (P-6), and Duranate ( 2.30 g of registered trademark) SBB-70P (manufactured by Asahi Kasei Co., Ltd.), 0.20 g of a PGMEA 10% by mass solution of silicone surfactant "BYK (registered trademark)" 333 (manufactured by BYK-Chemie Co., Ltd.) as a surfactant, A solution dissolved in 30.32 g of PGMEA was added to obtain a colored resin composition PC-18 having a total solids concentration of 22% by mass and a coloring material content of 25 parts by mass per 100 parts by mass of the total solids. The same evaluation as in Example 1 was performed using the obtained colored resin
  • Example 1 A colored resin composition PC-19 was obtained in the same manner as in Example 3 except that the colorant dispersion (DP-8) was used instead of the colorant dispersion (DP-2). The same evaluation as in Example 1 was performed using the obtained colored resin composition PC-19. Table 4 shows the results.
  • the colored resin compositions of Examples are excellent in viscosity stability and curability at low-temperature baking, and have high adhesion after the light resistance test and high-temperature, high-humidity test.
  • the colored resin composition of Comparative Example 1 has insufficient viscosity stability, and has low adhesion and adhesion after the light resistance test/high temperature and high humidity test.
  • the curability at the time of low-temperature firing is also insufficient.
  • the colored resin composition of Comparative Example 2 has insufficient viscosity stability and curability during low-temperature baking.
  • the colored resin composition of the present invention can be suitably used as a black decorative ink for forming a light-shielding film in the non-display area of the cover lens of an in-vehicle display or the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne une composition de résine colorée comprenant (A) une résine contenant un groupe hydroxyle ou un groupe acide, (B) un colorant, (C) un dispersant et (D) un isocyanate bloqué, le dispersant (C) étant un dispersant acrylique ayant un groupe basique. La composition de résine colorée peut durcir à de basses températures et présente une excellente stabilité de viscosité à température ordinaire. La composition de résine colorée, même après un essai de résistance à la lumière ou un essai à haute température et humidité élevée, conserve une adhésivité élevée.
PCT/JP2022/001701 2021-01-28 2022-01-19 Composition de résine colorée, film coloré et substrat décoratif WO2022163449A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202280007802.8A CN116568762A (zh) 2021-01-28 2022-01-19 着色树脂组合物、着色膜、装饰基板
KR1020237024062A KR20230136739A (ko) 2021-01-28 2022-01-19 착색 수지 조성물, 착색막, 장식 기판
JP2022504576A JPWO2022163449A1 (fr) 2021-01-28 2022-01-19

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-011665 2021-01-28
JP2021011665 2021-01-28

Publications (1)

Publication Number Publication Date
WO2022163449A1 true WO2022163449A1 (fr) 2022-08-04

Family

ID=82653401

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/001701 WO2022163449A1 (fr) 2021-01-28 2022-01-19 Composition de résine colorée, film coloré et substrat décoratif

Country Status (5)

Country Link
JP (1) JPWO2022163449A1 (fr)
KR (1) KR20230136739A (fr)
CN (1) CN116568762A (fr)
TW (1) TW202235456A (fr)
WO (1) WO2022163449A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009169221A (ja) * 2008-01-18 2009-07-30 Seiko Epson Corp カラーフィルター用インクセット、カラーフィルターの製造方法、カラーフィルター、画像表示装置、および、電子機器
JP2013249426A (ja) * 2012-06-01 2013-12-12 Kansai Paint Co Ltd 塗料組成物及び塗装物品
JP2015172103A (ja) * 2014-03-11 2015-10-01 Dic株式会社 導電性インキ組成物、導電性パターンの製造方法及び導電性回路
JP2016138229A (ja) * 2015-01-29 2016-08-04 株式会社シマノ インクジェット印刷用インク
JP2016200615A (ja) * 2015-04-07 2016-12-01 東レ株式会社 積層パターンの製造方法、積層パターン形成基板及びタッチパネル
JP2017134147A (ja) * 2016-01-26 2017-08-03 東レ株式会社 感光性樹脂組成物、それを用いた膜、タッチパネル、硬化パターン付き基板の製造方法、および積層パターン付き基板の製造方法
WO2018155500A1 (fr) * 2017-02-23 2018-08-30 日立化成株式会社 Encre pour impression à jet d'encre
WO2019059359A1 (fr) * 2017-09-25 2019-03-28 東レ株式会社 Composition de résine colorée, film coloré, filtre coloré, et dispositif d'affichage à cristaux liquides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200832065A (en) * 2006-08-11 2008-08-01 Sumitomo Chemical Co Polymerizable resin composition
JP2015108049A (ja) * 2013-12-04 2015-06-11 関西ペイント株式会社 ちぢみ模様塗膜を形成可能な塗料組成物
JP6520091B2 (ja) * 2013-12-16 2019-05-29 Jsr株式会社 着色組成物、着色硬化膜及び表示素子

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009169221A (ja) * 2008-01-18 2009-07-30 Seiko Epson Corp カラーフィルター用インクセット、カラーフィルターの製造方法、カラーフィルター、画像表示装置、および、電子機器
JP2013249426A (ja) * 2012-06-01 2013-12-12 Kansai Paint Co Ltd 塗料組成物及び塗装物品
JP2015172103A (ja) * 2014-03-11 2015-10-01 Dic株式会社 導電性インキ組成物、導電性パターンの製造方法及び導電性回路
JP2016138229A (ja) * 2015-01-29 2016-08-04 株式会社シマノ インクジェット印刷用インク
JP2016200615A (ja) * 2015-04-07 2016-12-01 東レ株式会社 積層パターンの製造方法、積層パターン形成基板及びタッチパネル
JP2017134147A (ja) * 2016-01-26 2017-08-03 東レ株式会社 感光性樹脂組成物、それを用いた膜、タッチパネル、硬化パターン付き基板の製造方法、および積層パターン付き基板の製造方法
WO2018155500A1 (fr) * 2017-02-23 2018-08-30 日立化成株式会社 Encre pour impression à jet d'encre
WO2019059359A1 (fr) * 2017-09-25 2019-03-28 東レ株式会社 Composition de résine colorée, film coloré, filtre coloré, et dispositif d'affichage à cristaux liquides

Also Published As

Publication number Publication date
JPWO2022163449A1 (fr) 2022-08-04
TW202235456A (zh) 2022-09-16
CN116568762A (zh) 2023-08-08
KR20230136739A (ko) 2023-09-26

Similar Documents

Publication Publication Date Title
CN101410734B (zh) 滤色片的制造方法和滤色片
US20130309448A1 (en) Coating based on polyurethane for display regions
JP6380723B1 (ja) 感光性着色組成物、硬化物、着色スペーサー、画像表示装置
JPWO2016143878A1 (ja) 着色スペーサー形成用感光性着色組成物、硬化物、着色スペーサー、画像表示装置
WO2009119546A1 (fr) Dispersant et composition de pigment, substance de dispersion de pigment, et encre pour jet d’encre utilisant le dispersant
TWI608057B (zh) 彩色濾光片用藍色顏料分散組合物及含有其之彩色濾光片用藍色顏料分散抗蝕劑組合物
JP5136273B2 (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP2016164623A (ja) 感光性着色組成物、硬化物、着色スペーサー、及び画像表示装置
TWI703192B (zh) 著色樹脂組成物
TW201522528A (zh) 黑矩陣用顏料分散物及含有其之黑矩陣用顏料分散光阻組成物
US7611572B2 (en) Pixel-forming colorant compositions and their use
JP2016167030A (ja) 感光性着色組成物、硬化物、着色スペーサー、及び画像表示装置
TW200933213A (en) Color filter ink, color filter ink set, color filter, image display device, and electronic device
CN101691459A (zh) 滤色片用墨液、滤色片用墨液组、滤色片、图像显示装置及电子设备
US20060283353A1 (en) Ink for color filter
JP2006273942A (ja) 塗料および塗膜
JP4334273B2 (ja) カラーフィルター用インクジェットインク用エポキシ樹脂組成物、カラーフィルターの製造方法、カラーフィルター、及び表示パネル
WO2022163449A1 (fr) Composition de résine colorée, film coloré et substrat décoratif
JP2011148910A (ja) インクジェット記録用インク組成物、及びカラーフィルター基板
JP2012184414A (ja) 着色組成物、およびカラーフィルタ並びにその製造方法
CN117716265A (zh) 着色树脂组合物、着色膜和装饰基板
JP2005225700A (ja) 錫含有酸化インジウム微粒子と透明導電膜形成用塗料及び透明導電膜並びに表示装置、透明導電膜の製造方法
JP2022112699A (ja) 着色樹脂組成物、遮光膜、加飾基板及び加飾フィルム
JP4815851B2 (ja) 着色組成物
CN102040886A (zh) 喷墨用着色组合物、滤色器以及液晶显示装置

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2022504576

Country of ref document: JP

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22745672

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 202280007802.8

Country of ref document: CN

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 22745672

Country of ref document: EP

Kind code of ref document: A1