WO2024084848A1 - Agent dispersant et composition de revêtement aqueuse - Google Patents

Agent dispersant et composition de revêtement aqueuse Download PDF

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Publication number
WO2024084848A1
WO2024084848A1 PCT/JP2023/032383 JP2023032383W WO2024084848A1 WO 2024084848 A1 WO2024084848 A1 WO 2024084848A1 JP 2023032383 W JP2023032383 W JP 2023032383W WO 2024084848 A1 WO2024084848 A1 WO 2024084848A1
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Prior art keywords
styrene
dispersant
parts
alkylene oxide
ammonium salt
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PCT/JP2023/032383
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English (en)
Japanese (ja)
Inventor
匠 北村
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サンノプコ株式会社
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Publication of WO2024084848A1 publication Critical patent/WO2024084848A1/fr

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    • 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
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/52—Natural or synthetic resins or their salts

Definitions

  • the present invention relates to a dispersant and a water-based coating composition.
  • a mixture with low volatile organic compound (VOC) content I. 10% to 80% by weight of an at least 50% salified copolymer of at least one ethylenically unsaturated, phenyl group-containing monomer and at least one ⁇ , ⁇ -unsaturated monocarboxylic acid and/or at least one ⁇ , ⁇ -unsaturated dicarboxylic acid, and optionally derivatives thereof, II.
  • VOC volatile organic compound
  • JP 2011-511142 A (WO2009/098025 Pamphlet)
  • An object of the present invention is to provide a dispersant which exhibits excellent dispersibility and which, when added to an aqueous coating agent, does not reduce the water resistance of the coating film obtained therefrom.
  • the dispersant of the present invention is characterized by comprising a styrene-maleic acid organic ammonium salt copolymer (A) and an alkylene oxide (having 2 to 4 carbon atoms; number of moles added: 3 to 50 moles) adduct (B) of at least one active hydrogen compound (having 4 to 18 carbon atoms) selected from the group consisting of alcohols, carboxylic acids, amines, and amides;
  • A styrene-maleic acid organic ammonium salt copolymer
  • alkylene oxide having 2 to 4 carbon atoms; number of moles added: 3 to 50 moles
  • adduct (B) of at least one active hydrogen compound (having 4 to 18 carbon atoms) selected from the group consisting of alcohols, carboxylic acids, amines, and amides;
  • the gist is that the active hydrogen compound has a branched alkyl chain having 4 to 18 carbon atoms.
  • the water-based coating composition of the present invention is characterized in that it contains a water-based coating agent and the above-mentioned dispersant.
  • the dispersant of the present invention exhibits excellent dispersibility and does not reduce the water resistance of the coating film obtained from the aqueous coating composition to which it is added.
  • the water-based coating composition of the present invention contains the above-mentioned dispersant, and therefore exhibits excellent dispersibility, resulting in a coating film with excellent water resistance.
  • the styrene-organic ammonium maleate copolymer (A) is not limited as long as it is a copolymer having styrene units (s) and organic ammonium maleate units (m) as constituent units, and a copolymer produced by a known method can be used.
  • a copolymer obtained by hydrolyzing a styrene-maleic anhydride copolymer and neutralizing it with an organic amine can be used.
  • Styrene-maleic anhydride copolymers can be produced by known methods, and are also readily available on the market.
  • XIRANE 1000 styrene-maleic anhydride resin, weight average molecular weight 5000, styrene 50 mol%, maleic anhydride 50 mol%, POLYSCOPE POLYMERS B.V.
  • XIRANE 2000 styrene-maleic anhydride resin, weight average molecular weight 6500, styrene 67 mol%, maleic anhydride 33 mol%, POLYSCOPE POLYMERS B.V.), SCOPE POLYMERS B.V.
  • XIRANE 3000 styrene-maleic anhydride resin, weight average molecular weight 10,000, styrene 75 mol%, maleic anhydride 25 mol%, POLYSCOPE POLYMERS B.V.
  • XIRANE 4000 styrene-maleic anhydride resin,
  • Organic amines include monoamines having 2 to 18 carbon atoms, such as primary amines (ethylamine, monoethanolamine, butylamine, propylamine, pentylamine, hexylamine, cyclohexylamine, aniline, benzylamine, 2-amino-2-methyl-1-propanol, and oleylamine); secondary amines (diethylamine, methylethylamine, diethanolamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, methylhexylamine, and dicyclohexylamine); and tertiary amines (triethylamine, triethanolamine, tripropylamine, dimethylpropylamine, tributylamine, tripentylamine, trihexylamine, dimethylcyclohexylamine, and tricyclohexylamine).
  • primary amines ethylamine, monoethanolamine, but
  • the molar ratio (s:m) of the styrene units (s) and the organic ammonium salt of maleic acid units (m) constituting the styrene-organic ammonium salt of maleic acid copolymer is preferably 80:20 to 40:60, more preferably 70:30 to 45:55, and particularly preferably 67:33 to 50:50. Within this range, the dispersibility and water resistance will be further improved.
  • the weight average molecular weight (Mw) of the styrene-maleic acid organic ammonium salt copolymer (A) is preferably 3,000 to 20,000, more preferably 4,000 to 15,000, and particularly preferably 6,000 to 12,000. Within this range, dispersibility and water resistance are further improved.
  • the weight average molecular weight (Mw) can be measured by gel permeation chromatography (GPC), for example, under the following conditions:
  • Measuring device HLC-8420GPC (Tosoh Corporation, "HLC” is a registered trademark of the company)
  • Column temperature: 40°C Solvent: methanol: ion-exchanged water: sodium acetate 800: 1200: 15 (weight ratio)
  • Standard material TSKgel standard polyethylene oxide (Tosoh Corporation, "TSKgel” is a registered trademark of the company.)
  • the active hydrogen compound having 4 to 18 carbon atoms is at least one selected from the group consisting of alcohols, carboxylic acids, amines and amides, and is not limited as long as the active hydrogen compound has a branched alkyl group having 4 to 18 carbon atoms and can chemically react with an alkylene oxide having 2 to 4 carbon atoms to form an alkylene oxide adduct of the active hydrogen compound.
  • the alcohols include branched monools with 4 to 18 carbon atoms, such as branched primary alcohols (2-methyl-1-propanol, 2-methyl-1-butanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, 3-ethyl-1-butanol, 3-methyl-1-butanol, 3,3-dimethyl-1-butanol, 2,3-dimethyl-1-butanol, 4,4-dimethyl-1-pentanol, 2,4,4-trimethyl-1-pentanol, 2-ethyl-1-hexanol, 2,2,4-trimethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isononanol, isodecanol, 2-methyl-1-undecanol, 12-methyl-1-tridecanol, isotridecanol, canol, 2-hexyl-1-decanol, isohexadecanol, 2-oc
  • Carboxylic acids include branched monocarboxylic acids having 4 to 18 carbon atoms, such as 2,2-dimethylpropanoic acid, 2-methylbutanoic acid, 4-methylpentanoic acid, 3,3-dimethylbutanoic acid, 2-methylhexanoic acid, 3,5,5-trimethylhexanoic acid, 2-ethylhexanoic acid, 2-methylpentadecanoic acid, and 2-methylheptadecanoic acid.
  • 2,2-dimethylpropanoic acid 2-methylbutanoic acid
  • 4-methylpentanoic acid 3,3-dimethylbutanoic acid
  • 2-methylhexanoic acid 3,5,5-trimethylhexanoic acid
  • 2-ethylhexanoic acid 2-methylpentadecanoic acid
  • 2-methylheptadecanoic acid 2-methylheptadecanoic acid
  • Amines include branched monoamines having 4 to 18 carbon atoms, such as branched primary amines (isobutylamine, isopentylamine, neopentylamine, 2-methylbutylamine, etc.); and branched secondary amines (methylisobutylamine, methylisopentylamine, methylneopentylamine, 2-methylbutylethylamine, etc.).
  • Amidations include branched monoamides having 4 to 18 carbon atoms, such as 2,2-dimethylpropanoic acid amide, isobutanoic acid amide, 2-methylbutanoic acid amide, 4-methylpentanoic acid amide, 3,3-dimethylbutanoic acid amide, 2-methylhexanoic acid amide, 3,5,5-trimethylhexanoic acid amide, 2-ethylhexanoic acid amide, 2-methylpentadecanoic acid amide, and 2-methylheptadecanoic acid amide.
  • Alkylene oxides having 2 to 4 carbon atoms include ethylene oxide, propylene oxide, and butylene oxide. Of these, from the viewpoint of dispersibility, it is preferable that ethylene oxide units are mainly contained, and the content (mol %) of ethylene oxide units is preferably 50 to 100, more preferably 60 to 100, and particularly preferably 80 to 100, based on the total number of moles of alkylene oxide units.
  • the number of moles of alkylene oxide (having 2 to 4 carbon atoms) added per mole of active hydrogen compound is preferably an integer between 3 and 50, more preferably an integer between 5 and 45, and particularly preferably an integer between 9 and 40. Within this range, the dispersibility is further improved.
  • the alkylene oxide adducts (B) of active hydrogen compounds can be obtained by known alkylene oxide addition reactions, or can be obtained from the market.
  • Product names include the Emulmin series (alkylene oxide adducts of alcohols, Sanyo Chemical Industries, Ltd., "Emulmin” is a registered trademark of the company), Sannonik series (alkylene oxide adducts of alcohols, Sanyo Chemical Industries, Ltd., “Sanonik” is a registered trademark of the company), Naroacty series (alkylene oxide adducts of alcohols, Sanyo Chemical Industries, Ltd., “Naroacty” is a registered trademark of the company), Puremeal series (alkylene oxide adducts of amines, Sanyo Chemical Industries, Ltd., "Puremeal” is a registered trademark of the company), and Ionette series (alkylene oxide adducts of carboxylic acids).
  • Examples include alkylene oxide adducts of alcohol, amine, or amide, Sanyo Chemical Industries, Ltd., "IONET” is a registered trademark of the company), Brownon series (alkylene oxide adducts of alcohol, amine, or amide, Aoki Oil & Fat Co., Ltd., “Brownon” is a registered trademark of the company), Finesurf series (alkylene oxide adducts of alcohol, Aoki Oil & Fat Co., Ltd., “Finesurf” is a registered trademark of the company), Safetycut series (alkylene oxide adducts of alcohol, Aoki Oil & Fat Co., Ltd.), Wondersurf series (alkylene oxide adducts of alcohol, Aoki Oil & Fat Co., Ltd., "Wondersurf” is a registered trademark of the company), and Nonion series (alkylene oxide adducts of alcohol or carboxylic acid, NOF Corporation).
  • IONET is a registered trademark of the company
  • the weight ratio (A:B) of the styrene-maleic acid organic ammonium salt copolymer (A) to the polyoxyalkylene compound (B) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, and particularly preferably 25:75 to 75:25. Within this range, the dispersibility and water resistance will be further improved.
  • the dispersant of the present invention is composed only of the styrene-maleic acid organic ammonium salt copolymer (A) and the alkylene oxide adduct of an active hydrogen compound (B), but may contain additives (defoamers, viscoelasticity modifiers, wetting agents, film-forming modifiers, etc.) and/or solvents to the extent that the effects of the present invention are not impaired.
  • Antifoaming agents include SN Defoamer 399, 1311, and 1315 (San Nopco Ltd.), viscoelasticity adjusting agents include SN Thickener 612, 621N, 617, and 618 (San Nopco Ltd.), wetting agents include SN Wet 125, 126, 366, S, FST2, L, 996, 980, and 984 (San Nopco Ltd.), and film forming adjusting agents include Kyowanol M (KH Neochem Co., Ltd., "Kyowanol" is a registered trademark of the company).
  • Solvents include water, ethylene glycol, propylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, and polyethylene glycol monobutyl ether.
  • the dispersant of the present invention is not limited in the manufacturing method as long as the styrene-maleic acid organic ammonium salt copolymer (A) and the alkylene oxide adduct of the active hydrogen compound (B) are uniformly mixed, and even if additives and/or a solvent are contained, it is sufficient that these are uniformly mixed. From the viewpoint of ease of manufacturing, it is preferable to manufacture using a solvent. Furthermore, the manufacturing may involve heating or cooling.
  • the active hydrogen compound is an amine having a branched alkyl group
  • the active hydrogen compound when mixing the styrene-maleic acid organic ammonium salt copolymer (A) and the alkylene oxide adduct of the active hydrogen compound (B) (the same applies after mixing), a part or all of the organic amine forming the salt of the styrene-maleic acid organic ammonium salt copolymer (A) and the alkylene oxide adduct (B) may undergo salt exchange.
  • the dispersant of the present invention is suitable for use in water-based coating agents (water-based paints, water-based inks, etc.), and when applied to water-based coating agents, the content (wt%) of the dispersant is preferably 0.01 to 10, and more preferably 0.05 to 5, based on the weight of the water-based coating agent. Within this range, even better dispersibility is exhibited.
  • the water-based coating agent preferably contains a water-based resin (emulsion or dispersion), pigment, water, and additives as necessary.
  • Water-based resins include acrylic resins, vinyl acetate resins, vinyl chloride resins, acrylic-styrene resins, silicone resins, urethane resins, epoxy resins, and fluororesins. Of these, acrylic resins, acrylic-styrene resins, and epoxy resins are preferred.
  • Pigments include inorganic pigments (calcium carbonate, titanium oxide, satin white, barium sulfate, talc, zinc oxide, gypsum, silica, ferrite, etc.) and organic pigments (carbon black, phthalocyanine blue, quinacridone red, isoindoline yellow, etc.).
  • additives include defoamers, dispersants (excluding the dispersants of the present invention), leveling agents, wetting agents, viscoelasticity adjusters, etc.
  • the water-based coating composition of the present invention can be produced by preparing an aqueous dispersion using the above-mentioned dispersant, pigment, water, and additives as necessary (grinding step), and then uniformly mixing the aqueous dispersion, aqueous resin, and additives as necessary (let-down step).
  • the above-mentioned dispersant may be added in the let-down step.
  • the above-mentioned dispersant and aqueous resin may be diluted with a solvent before use.
  • the dispersant of the present invention can be used for purposes other than water-based coating agents, and is also suitable for water-based pigment pastes and water-based ceramic slurries.
  • the weight average molecular weight (Mw) was measured by gel permeation chromatography (GPC) under the above conditions (hereinafter the same).
  • styrene-maleic anhydride resin 2: XIRANE 2000, weight average molecular weight 6500, styrene 67 mol%, maleic anhydride 33 mol%, POLYSCOPE POLYMERS B
  • a monomer solution was prepared by dissolving 104 parts (1 mol part) of styrene and 98 parts (1 mol part) of maleic anhydride in 200 parts of methyl ethyl ketone, and an initiator solution was prepared by dissolving 0.8 parts (3.5 ⁇ 10-3 mol parts) of an oil-soluble azo polymerization initiator (V-601, Wako Pure Chemical Industries, Ltd., Fuji Film Corporation) in 100 parts of methyl ethyl ketone.
  • V-601 Wako Pure Chemical Industries, Ltd., Fuji Film Corporation
  • a 40% aqueous solution (yellow liquid) of styrene-maleic acid organic ammonium salt copolymer (A4: weight average molecular weight 10,000) was obtained in the same manner as in Production Example 1, except that "styrene-maleic anhydride resin (1)” was replaced with “styrene-maleic anhydride copolymer (3)".
  • styrene-maleic anhydride copolymer (4: yellow solid, styrene 50 mol %, maleic anhydride 50 mol %, weight average molecular weight 10,000) was obtained in the same manner as in Production Example 4, except that the amount of the oil-soluble azo polymerization initiator (V-601, Wako Pure Chemical Industries, Ltd.) was changed from 0.8 parts (3.5 ⁇ 10 ⁇ 3 mol parts) to 0.5 parts (2.2 ⁇ 10 ⁇ 3 mol parts).
  • V-601 Wako Pure Chemical Industries, Ltd. oil-soluble azo polymerization initiator
  • a 40% aqueous solution of styrene-maleic acid organic ammonium salt copolymer (A5: weight average molecular weight 12,000) was obtained in the same manner as in Production Example 1, except that "styrene-maleic anhydride resin (1)” was changed to "styrene-maleic anhydride resin (4)".
  • an active hydrogen compound B5: BROWNON EH-30, 2-ethylhexyl alcohol/EO 30 mol adduct, Aoki Oil & Fat Co., Ltd., "BROWNON” is a registered trademark of the company
  • B6 active hydrogen compound
  • an antifoaming agent SN DEFORMER 399, San Nopco Co., Ltd.
  • the dispersion slurry was then left to stand in a water tank at 25°C for 15 minutes, and the viscosity was measured using a TVB15 viscometer (Toki Sangyo Co., Ltd., 25°C, 60 rpm). Then, 0.1 parts of the evaluation sample was added, mixed for 5 minutes, and the dispersion slurry was left to stand in a water tank at 25°C for 15 minutes, and the viscosity was measured in the same manner. This operation was repeated until the slurry viscosity was 100 mPa ⁇ s or less, and the amount of addition (evaluation sample consumption x 100/total amount of water and titanium oxide;%) was calculated from the total amount of evaluation sample (dispersant) consumed, and shown in the table below. The smaller the amount added, the better the dispersibility.
  • Preparation of acrylic styrene emulsion color paste and coating sample (1) 30 parts of carbon black (MA-8, Mitsubishi Chemical Corporation), 20 parts of evaluation sample (dispersant), 35 parts of water and glass beads (diameter 2 mm) were placed in a glass bottle and shaken with a paint shaker for 180 minutes to prepare a color paste, and then 20 parts of the color paste and 80 parts of acrylic styrene emulsion (ACRONAL 7659, BASF, concentration 50% by weight, "ACRONAL” is a registered trademark of BASF Societas Europea) were uniformly mixed to prepare a water-based coating composition (1; acrylic styrene emulsion color paste), which was then coated on a glass plate using a 6-mil applicator and dried at 40°C for 3 hours to prepare a coating sample (1).
  • ACRONAL 7659 BASF, concentration 50% by weight
  • Preparation of acrylic emulsion paint and coating sample (2) Using the raw material composition shown in Table 3, grinding and letdown were performed using an Excel Auto Homogenizer equipped with an impeller-type blade to prepare a water-based coating composition (2; acrylic emulsion paint). Subsequently, the water-based coating composition (2) was applied onto a glass plate using a 6-mil applicator and dried at 25°C for 24 hours to prepare a coating sample (2).
  • Dispersibility 1 Dispersibility by gloss value The gloss value (60°) of each of the coating samples (2) was measured using a gloss meter and is shown in the table below. The higher this value, the better the dispersibility.
  • the dispersant of the present invention has superior dispersibility compared to the comparative dispersant, and the aqueous coating composition using the dispersant of the present invention has superior water resistance compared to the aqueous coating composition using the comparative dispersant, and the appearance of the coating film obtained by applying the aqueous coating composition was not impaired.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Paints Or Removers (AREA)

Abstract

L'objectif de la présente invention est de fournir un agent dispersant qui présente une excellente aptitude à la dispersion et qui ne détériore pas la résistance à l'eau d'un film de revêtement résultant même lorsque l'agent dispersant est ajouté à un agent de revêtement aqueux. La présente invention est un agent dispersant caractérisé en ce qu'il comprend : (A) un copolymère styrène-sel d'ammonium organique d'acide maléique ; et (B) un produit d'addition d'oxyde d'alkylène (le nombre d'atomes de carbone : 2 à 4, la quantité d'oxyde d'alkylène ajoutée : 3 à 50 moles) d'au moins un composé d'hydrogène actif (le nombre d'atomes de carbone : 4 à 18) sélectionné parmi le groupe constitué des alcools, des acides carboxyliques, des amines et des amides, le composé d'hydrogène actif ayant une chaîne alkyle ramifiée ayant 4 à 18 atomes de carbone. Le rapport molaire en constituants (s:m) entre les unités styrène (s) et les unités sel d'ammonium d'acide maléique (m) constituant le copolymère styrène-sel d'ammonium d'acide maléique est de préférence de 80:20 à 40:60. Le rapport pondéral en teneur (A:B) entre le copolymère styrène-sel d'ammonium d'acide maléique (A) et le composé polyoxyalkylène (B) est de préférence de 10:90 à 90:10.
PCT/JP2023/032383 2022-10-18 2023-09-05 Agent dispersant et composition de revêtement aqueuse WO2024084848A1 (fr)

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JP2022-166875 2022-10-18
JP2022166875A JP2024059282A (ja) 2022-10-18 2022-10-18 分散剤及び水系コーティング組成物

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03250077A (ja) * 1990-02-28 1991-11-07 Pentel Kk 水性顔料組成物
JPH08120101A (ja) * 1994-10-26 1996-05-14 Matsushita Electric Works Ltd フッ素樹脂プリプレグの製造方法
JP2003226892A (ja) * 2002-02-06 2003-08-15 Dai Ichi Kogyo Seiyaku Co Ltd 非イオン界面活性剤
WO2022044525A1 (fr) * 2020-08-31 2022-03-03 日信化学工業株式会社 Agent de dispersion, élément de dispersion, composition d'encre et son procédé de fabrication
WO2023286481A1 (fr) * 2021-07-15 2023-01-19 サンノプコ株式会社 Dispersant et composition de revêtement à base d'eau

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03250077A (ja) * 1990-02-28 1991-11-07 Pentel Kk 水性顔料組成物
JPH08120101A (ja) * 1994-10-26 1996-05-14 Matsushita Electric Works Ltd フッ素樹脂プリプレグの製造方法
JP2003226892A (ja) * 2002-02-06 2003-08-15 Dai Ichi Kogyo Seiyaku Co Ltd 非イオン界面活性剤
WO2022044525A1 (fr) * 2020-08-31 2022-03-03 日信化学工業株式会社 Agent de dispersion, élément de dispersion, composition d'encre et son procédé de fabrication
WO2023286481A1 (fr) * 2021-07-15 2023-01-19 サンノプコ株式会社 Dispersant et composition de revêtement à base d'eau

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