WO2022264768A1 - Agent antibactérien-antiviral, composition de revêtement antibactérienne-antivirale, stratifié, composition de résine antibactérienne-antivirale et article moulé - Google Patents

Agent antibactérien-antiviral, composition de revêtement antibactérienne-antivirale, stratifié, composition de résine antibactérienne-antivirale et article moulé Download PDF

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Publication number
WO2022264768A1
WO2022264768A1 PCT/JP2022/021490 JP2022021490W WO2022264768A1 WO 2022264768 A1 WO2022264768 A1 WO 2022264768A1 JP 2022021490 W JP2022021490 W JP 2022021490W WO 2022264768 A1 WO2022264768 A1 WO 2022264768A1
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Prior art keywords
antibacterial
resin
antiviral
metal
fatty acid
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PCT/JP2022/021490
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English (en)
Japanese (ja)
Inventor
麻里 宇治川
聡子 伊東
宏明 中野
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Dic株式会社
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Priority to CN202280041698.4A priority Critical patent/CN117500376A/zh
Priority to JP2023501483A priority patent/JPWO2022264768A1/ja
Publication of WO2022264768A1 publication Critical patent/WO2022264768A1/fr
Priority to JP2023138804A priority patent/JP2023165705A/ja

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/06—Aluminium; Calcium; Magnesium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of 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
    • 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
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • 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
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Definitions

  • the present invention relates to an antibacterial and antiviral agent, an antibacterial and antiviral coating composition, a laminate, an antibacterial and antiviral resin composition, and a molded article.
  • Patent Document 1 As antibacterial and antiviral agents, photocatalyst-based ( TiO2 , etc.) and metal-based (Ag, etc.) are known (for example, Patent Document 1). are mixed to form a coating composition, and the composition is applied to an object to be applied.
  • the inorganic metal compound which is a conventional antibacterial and antiviral agent
  • the color of the application target changes and the texture of the application target becomes rough to the touch.
  • the coating layer obtained from the coating composition has a turbid color due to the inorganic metal compound.
  • a composition containing an inorganic metal compound requires a dispersing treatment because the inorganic compound is generally a powder, which poses a problem in terms of productivity.
  • the problem to be solved by the present invention is to provide an antibacterial and antiviral agent that has high compatibility with resins, antibacterial and antiviral activity, and has a reduced effect on the appearance of the object to which it is applied.
  • the present inventors found that the effect on the appearance of the application target can be reduced by making the antibacterial and antiviral agent in the form of a fatty acid metal salt or a metal complex. perfected the invention.
  • the present invention provides one or more selected from the group consisting of fatty acid metal salts, metal complexes of heteroatom-containing ligands and metal ions, and metal complexes of heteroatom-containing ligands and fatty acid metal salts.
  • An antibacterial and antiviral agent wherein the metal of the fatty acid metal salt, the metal complex of the heteroatom-containing compound ligand and the metal ion, and the metal complex of the heteroatom-containing compound ligand and the fatty acid metal salt is , each independently lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium , bismuth, lead, gold, platinum or rare earths.
  • an antibacterial and antiviral agent that has high compatibility with resins, antibacterial and antiviral activity, and has a reduced effect on the appearance of the object to which it is applied.
  • the antimicrobial antiviral agent of the present invention is selected from the group consisting of fatty acid metal salts, metal complexes of heteroatom-containing ligands and metal ions, and metal complexes of heteroatom-containing ligands and fatty acid metal salts.
  • the metal complex of the heteroatom-containing compound ligand and the metal ion, and the metal complex of the heteroatom-containing compound ligand and the fatty acid metal salt are each independently lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth , lead, gold, platinum or rare earths.
  • the antibacterial and antiviral agent of the present invention takes the form of a fatty acid metal salt or metal complex, and contains a binder resin due to the antibacterial and antiviral properties of the metal and the high compatibility with organic substances of the fatty acid or complex ligand.
  • a binder resin due to the antibacterial and antiviral properties of the metal and the high compatibility with organic substances of the fatty acid or complex ligand.
  • antibacterial means the effect of reducing the number of bacteria, the effect of inactivating bacteria, the effect of reducing the infectivity of bacteria, and the like.
  • antiviral is meant to include the effect of reducing the number of viruses, the effect of inactivating viruses, the effect of reducing the infectivity of viruses, and the like.
  • the bacteria to be antibacterially treated in the present invention are not particularly limited, and may be either bacteria or fungi.
  • Bacteria include Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Salmonella, Moraxella, and Legionella; Gram-positive bacteria such as Staphylococcus aureus and Clostridium.
  • fungi include yeasts such as Candida, Rhodotorula and baker's yeast; molds such as red mold and black mold.
  • the virus to be antiviral is not particularly limited, and may be either a known enveloped virus (a virus having an envelope) or a non-enveloped virus (a virus without an envelope).
  • envelope virus examples include coronavirus, influenza virus, rubella virus, Ebola virus, measles virus, varicella-zoster virus, herpes virus, mumps virus, arbovirus, respiratory syncytial virus, SARS virus, hepatitis virus (e.g., A hepatitis virus, hepatitis B virus, hepatitis C virus, hepatitis D virus, hepatitis E virus, etc.), yellow fever virus, AIDS virus, rabies virus, hantavirus, dengue virus, Nipah virus, lyssa virus and the like.
  • hepatitis virus e.g., A hepatitis virus, hepatitis B virus, hepatitis C virus, hepatitis D virus, hepatitis E virus, etc.
  • yellow fever virus AIDS virus, rabies virus, hantavirus, dengue virus, Nipah virus, lyssa virus and the like.
  • non-enveloped viruses examples include adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, polyomavirus, BK virus, rhinovirus, feline calicivirus, and the like. is mentioned.
  • the antibacterial antiviral agent of the present invention will be described below.
  • the fatty acid metal salt which is the antibacterial and antiviral agent of the present invention, is, for example, a compound represented by the following general formula (1).
  • R 1 is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms, n1 is an integer ranging from 1 to 4; M 1 is lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, Bismuth, lead, gold, platinum or rare earths.
  • n1 is an integer of 2 or more
  • a plurality of R 1 may be the same or different.
  • the alkyl group having 1 to 21 carbon atoms for R 1 may be a straight-chain alkyl group, a branched alkyl group, or may contain an alicyclic structure.
  • a hydrogen atom or an alkyl group having 1 to 21 carbon atoms for R 1 is a carboxylic acid obtained by removing a carboxyl group (COOH) from a carboxylic acid having 1 to 22 carbon atoms represented by R 1 COOH used for producing a fatty acid metal salt.
  • carboxylic acid residue include formic acid residue, acetic acid residue, propionic acid residue, butanoic acid residue, pentanoic acid residue, hexanoic acid residue, 2-ethylbutyric acid residue, heptanoic acid residue, octanoic acid residue.
  • the alkyl group having 1 to 21 carbon atoms for R 1 is preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 11 carbon atoms, from the viewpoint of adhesion to a substrate, which will be described later. is.
  • R 1 is preferably formic acid residue, acetic acid residue, propionic acid residue, butanoic acid residue, pentanoic acid residue, hexanoic acid residue, 2-ethylbutyric acid residue, heptanoic acid residue, octanoic acid residue , 2-ethylhexanoic acid residue, isononanoic acid residue, neodecanoic acid residue, naphthenic acid residue, stearic acid residue or oleic acid residue.
  • M 1 is lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, Bismuth, lead, gold, platinum or rare earth, preferably bismuth, neodymium, magnesium, cobalt, copper, silver, zinc, lead, yttrium, lanthanum, praseodymium, samarium, gadolinium, more preferably bismuth, neodymium, magnesium , cobalt, silver, copper, lead, yttrium, lanthanum, praseodymium, samarium, and gadolinium.
  • the metal of the fatty acid metal salt is bismuth, neodymium, magnesium, lanthanum, gadolinium, or samarium, coloring due to the addition of the antibacterial and antiviral
  • rare earths are scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), and europium.
  • Sc scandium
  • Y yttrium
  • La cerium
  • Ce cerium
  • Pr praseodymium
  • Nd neodymium
  • promethium Pm
  • Sm samarium
  • Eu europium
  • Eu gadolinium
  • Tb terbium
  • Dy dysprosium
  • Ho holmium
  • Er erbium
  • Tm thulium
  • Yb ytterbium
  • Lu lutetium
  • n1 is a numerical value determined by the ion valence of the metal atom of M1. For example, n1 is 3 if M1 is boron, and n1 is 2 if M1 is cobalt.
  • the fatty acid metal salt that is the antibacterial and antiviral agent of the present invention also includes the form of fatty acid metal borate.
  • the fatty acid borate metal salt is, for example, a compound represented by the following general formula (2).
  • R 2 is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms
  • M2 is boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or rare earths.
  • the alkyl group having 1 to 21 carbon atoms for R 2 is the same as the alkyl group having 1 to 21 carbon atoms for R 1 in general formula (1).
  • the metal of M2 is the same as the metal of M1 in the general formula ( 1 ).
  • a fatty acid metal salt When a fatty acid metal salt is used as the antibacterial and antiviral agent of the present invention, one type of fatty acid metal salt may be used alone, or two or more types of fatty acid metal salts having different structures may be used.
  • Fatty acid metal salts can be produced by known methods, and commercially available products may be used.
  • the metal complex of a heteroatom-containing ligand and a metal ion and the metal complex of a heteroatom-containing ligand and a fatty acid metal salt which are the antibacterial and antiviral agents of the present invention, are composed of a metal ion or a fatty acid metal salt and a heteroatom-containing ligand. It is a compound that forms a complex with a ligand through a coordinate bond.
  • the same metal ion as the metal of the fatty acid metal salt described as the antibacterial and antiviral agent of the present invention can be used.
  • the fatty acid metal salt in which a heteroatom-containing ligand forms a metal complex the same fatty acid metal salt as described for the antibacterial and antiviral agent of the present invention can be used.
  • a heteroatom-containing ligand that forms a metal complex may be a ligand having in its molecule one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and phosphorus.
  • the heteroatom-containing ligand include N-methylmorpholine, pyridine, 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0 ] nonene-5 (DBN), 1,4-diazabicyclo[2.2.2]octane (DABCO), 4-dimethylaminoamine (DMAP), dicyandiamide (DICY), tri-n-butylamine, dimethylbenzylamine, butylamine , 1,2-propanediamine, 1,2-cyclohexanediamine, octylamine, monoethanolamine, diethanolamine, triethanolamine, 2-[[(2-dimethylamino)ethyl]methylamino]ethanol, picolinic acid, 2, 2′-[
  • Heteroatom-containing ligands are preferably picolinic acid, 2- ⁇ [(2-dimethylamino)ethyl]methylamino ⁇ ethanol, 1,2-propanediamine, 1,2-cyclohexanediamine, monoethanolamine, diethanolamine, triethanolamine, imidazole, 1-methylimidazole, 2-methylimidazole, 4-methylimidazole, 2,4-dimethylimidazole, 1,4-diethylimidazole, 8-quinolinol, 5-chloro-8-quinolinol, 2,2 One or more amine ligands selected from '-bipyridyl and its derivatives, and 2,2'-[propane-1,2-diylbis(azanylylidenemethanilylidene)]diphenol and its derivatives.
  • heteroatom-containing ligands that form the metal complex may be of one type alone, or may be of two or more types having mutually different structures.
  • the ratio (molar ratio) of the metal ion or fatty acid metal salt and the heteroatom-containing ligand is such that the heteroatom-containing ligand is 0 per mol of the metal atom of the metal ion or fatty acid metal salt. .1 to 12 mol, preferably 0.3 to 10 mol, more preferably 0.5 to 10 mol.
  • the metal ion in the metal complex is an aluminum ion
  • the aluminum complex is preferably an aluminum chelate compound represented by the following general formula (3-1) and an aluminum chelate compound represented by the following general formula (3-2). It is one or more selected from compounds.
  • R 311 to R 316 and R 321 to R 326 are each independently an alkyl group having 1 to 22 carbon atoms or an alkoxy group having 1 to 22 carbon atoms.
  • the alkylene group portion of the alkyl group having 1 to 22 carbon atoms and the alkoxy group having 1 to 22 carbon atoms in R 311 to R 316 and R 321 to R 326 may be linear or branched, and may have an alicyclic structure. may include The number of carbon atoms in the alkylene group portion of the alkyl group and alkoxy group of R 311 to R 316 and R 321 to R 326 is preferably 1 to 9.
  • the alkyl group having 1 to 22 carbon atoms of R 311 to R 316 and R 321 to R 326 is preferably methyl group or ethyl group.
  • the alkoxy group having 1 to 22 carbon atoms of R 311 to R 316 and R 321 to R 326 is preferably methoxy group, ethoxy group or oleyloxy group.
  • aluminum chelate compounds include aluminum tris(acetylacetonate), aluminum tris(ethylacetoacetate), aluminum monoacetylacetonate bis(ethylacetoacetate), aluminum monoacetylacetonate bisoleylacetoacetate, ethylacetoacetate.
  • the antimicrobial antiviral agent of the present invention is preferably a water-insoluble antimicrobial antiviral agent. Since the antibacterial and antiviral agent is water-insoluble, the antibacterial and antiviral properties are excellent in persistence even when it is exposed to water such as daily rain.
  • water-insoluble means that the amount of water required to dissolve 1 g of the antibacterial/antiviral agent at 20°C is 10 ml or more.
  • Metal complexes of heteroatom-containing ligands and metal ions and metal complexes of heteroatom-containing ligands and fatty acid metal salts which are antibacterial and antiviral agents, can be produced by known methods, It can be produced by reacting a metal salt with a heteroatom-containing ligand. Moreover, the said metal complex may use a commercial item.
  • the coating composition of the present invention contains the antibacterial antiviral agent of the present invention and a binder resin. Since the antibacterial antiviral agent of the present invention has high compatibility with the binder resin, the transparency of the coating layer obtained from the coating composition containing the antibacterial antiviral agent of the present invention is impaired by the antibacterial antiviral agent. It is possible to reduce the influence on the appearance such as.
  • the antibacterial and antiviral agent of the present invention can exhibit an effect of promoting adhesion to substrates, and the coating layer containing the antibacterial and antiviral agent of the present invention can exhibit high adhesion to substrates. Therefore, in the laminate of the base material and the coating layer laminated on the base material, the coating layer exhibits antibacterial and antiviral properties, and at the same time, the base material and the coating layer can exhibit high adhesion.
  • the content of the antibacterial and antiviral agent of the present invention in the coating composition of the present invention is not particularly limited, and for example, the metal derived from the antibacterial and antiviral agent is in the range of 0.01 to 30 parts by weight per 100 parts by weight of the resin solid content. It is preferably contained in the range of 0.01 to 15 parts by mass with respect to 100 parts by mass of the resin solid content, more preferably in the range of 0.01 to 10 parts by mass with respect to 100 parts by mass of the resin solid content and more preferably in the range of 0.1 to 10 parts by mass per 100 parts by mass of the solid content of the resin.
  • resin solid content means the total amount of solid content such as binder resin contained in the coating composition.
  • the antibacterial and antiviral agent of the present invention contained in the coating composition of the present invention may be one type alone, or two or more types.
  • the binder resin contained in the coating composition of the present invention is not particularly limited, and for example, any type of emulsion resin, latex resin, thermosetting resin, and active energy ray-curable resin can be used.
  • the binder resin may be either a water-based resin or a water-insoluble resin (solvent-based resin).
  • water-soluble resin means that the amount of water required to dissolve 1 g of resin at 20°C is less than 10 ml.
  • Water-insoluble resin refers to a resin that is not the aforementioned “water-soluble resin”.
  • binder resins include acrylic resins, vinyl acetate resins, styrene resins, vinyl chloride resins, olefin resins, urethane resins, urea resins, urethane urea resins, acrylic urethane resins, epoxy resins, melamine resins, phenol resins, and polyester resins. , alkyd resins, silicone resins, polyphenylene sulfide resins, acrylonitrile/styrene copolymer resins, acrylonitrile/butadiene copolymer resins and acrylonitrile/butadiene/styrene copolymer (ABS) resins.
  • the binder resin includes those obtained by modifying the above resins. For example, if it is a phenol resin, it also includes a rosin-modified phenol resin.
  • the binder resin contained in the coating composition of the present invention may be one type alone, or two or more types.
  • the content of the binder resin in the coating composition of the present invention is not particularly limited, and may be appropriately set, for example, in the range of 10 to 100% by mass with respect to the total resin solid content mass of the coating composition.
  • the coating composition of the present invention only needs to contain the antimicrobial antiviral agent of the present invention and a binder resin, and may further contain a dispersion medium.
  • the dispersion medium is added for the purpose of adjusting the viscosity of the coating composition, and may be either an aqueous medium or an oil medium.
  • dispersion media include water, 1-butanol, isobutanol, 1-pentanol, 2-methyl-2-pentanol, 3-methyl-3-pentanol, methyl ethyl ketone, methanol, ethanol, and n-propyl alcohol.
  • monofunctional alcohols such as isopropyl alcohol, various diols, polyhydric alcohols such as glycerin, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, propylene glycol, 1,2-butanediol, 3-methyl-1,3-butanediol, 1,2 Diols such as pentanediol, 2-methyl-1,3-propanediol, 1,2-hexanediol, dipropylene glycol and diethylene glycol, bisphenol A, alkylene oxides having 2 or 3 carbon atoms of bisphenol A (average addition mole number of 1 or more 16 or less) adduct
  • the dispersion medium contained in the coating composition of the present invention may be one type alone, or two or more types.
  • the content of the dispersion medium in the coating composition of the present invention is not particularly limited.
  • the coating composition of the invention may further contain a plasticizer.
  • a plasticizer By adding a plasticizer to the coating composition, flexibility can be imparted to the resulting coating layer, and conformability to the substrate can be improved.
  • the plasticizer is not particularly limited, and examples thereof include phthalates, non-aromatic dibasic acid esters, aliphatic esters, esters of polyalkylene glycol, phosphates, trimellitates, chlorinated paraffins, and hydrocarbons. system oils, process oils, polyethers, epoxy plasticizers, polyester plasticizers, etc., preferably phthalates.
  • plasticizers include dibutyl phthalate, diheptyl phthalate, di(2-ethylhexyl) phthalate, dioctyl phthalate, dioctyl adipate, dioctyl sebacate, dibutyl sebacate, isodecyl succinate, tricresyl phosphate, tributyl phosphate, epoxy oxidized soybean oil, benzyl epoxystearate, and the like.
  • the plasticizer contained in the coating composition of the present invention may be one type alone, or two or more types.
  • the content of the plasticizer in the coating composition of the present invention is not particularly limited, and may be appropriately set, for example, within the range of 0.1 to 50 parts by mass with respect to 100 parts by mass of the resin solid content of the coating composition.
  • the coating composition of the present invention may contain the antibacterial and antiviral agent of the present invention, a binder resin, and optionally a dispersion medium and/or a plasticizer, and may contain other additives within a range that does not impair the effects of the present invention.
  • additives include pigments, matting agents, curing agents, curing accelerators, antifoaming agents, dispersants, leveling agents, thickeners, antioxidants, weathering agents, flame retardants, antistatic agents, lubricants, Preservatives and the like are included.
  • a coating layer is formed by applying the coating composition of the present invention to the substrate surface and applying a curing method (thermal curing, active energy ray curing, etc.) suitable for the binder resin to the resulting coating film. be able to.
  • a curing method thermal curing, active energy ray curing, etc.
  • any known coating method can be used, for example, roll coater, electrostatic coating, bar coater, gravure coater, knife coater, dipping coating, spray coating, and the like. method.
  • the substrate to be coated is not particularly limited, and examples thereof include paper, synthetic paper, steel plate, aluminum foil, glass, wood, woven fabric, knitted fabric, non-woven fabric, gypsum board, wood board, resin substrate, and the like. .
  • the resin substrate include polyethylene terephthalate (PET) film, polystyrene film, polyamide film, polyacrylonitrile film, polyethylene film (LLDPE: low density polyethylene film, HDPE: high density polyethylene film), polypropylene film (CPP: Non-oriented polypropylene film, OPP: biaxially oriented polypropylene film), polyvinyl alcohol film, ethylene-vinyl alcohol copolymer film, polycarbonate film, polyethylene terephthalate film, polymethyl methacrylate film, polystyrene film, polyester film, polyolefin film, epoxy resin Film, melamine resin film, triacetyl cellulose resin film, polyvinyl alcohol film, ABS resin film, norbornene resin film, cyclic olefin resin film, polyimide resin film, polyvinyl fluoride resin film, polyvinylidene fluoride resin film, ethylene-acetic acid A vinyl copolymer film and the like can be mentioned.
  • the resin base material
  • the resin composition of the present invention contains the antimicrobial antiviral agent of the present invention and a resin.
  • the resin composition containing the antibacterial and antiviral agent of the present invention can be used not only for coating purposes, but also can be molded into a molded article exhibiting antibacterial and antiviral properties.
  • the same resin as the binder resin contained in the coating composition of the present invention can be used.
  • the resin composition of the present invention can contain the same components as the coating composition of the present invention can contain.
  • a molding method suitable for the resin to be used may be adopted. casting method.
  • the coating layer obtained using the coating composition of the present invention and the molded article obtained using the resin composition of the present invention can be suitably used as a material having antibacterial and antiviral activity in places where human hands touch.
  • Applications include smartphone exteriors, computer exteriors, touch panels, handrails, doorknobs, washstands, push buttons such as elevator buttons, interior goods (wallpaper, flooring, etc.), various packaging materials, various textile products, medical equipment (medical gloves, medical glasses, etc.).
  • fatty acid metal salt (Y) that is yttrium 2-ethylhexanoate
  • fatty acid metal salt (Pb) that is lead 2-ethylhexanoate and fatty acid metal salt (Ag) that is silver 2-ethylhexanoate (yttrium 2-ethylhexanoate manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd., lead 2-ethylhexanoate manufactured by DIC Corporation, and silver 2-ethylhexanoate manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.).
  • Example 1-13 and Comparative Example 1-2 Production of urethane urea resin coated substrate
  • a urethane urea resin (“Barnock EPL-925” manufactured by DIC Corporation) was added with the antibacterial and antiviral agents shown in Tables 1 and 2 so that the metal content of the antibacterial and antiviral agent was 1% by mass of the solid content of the urethane urea resin. were mixed respectively to prepare coating compositions.
  • no antibacterial and antiviral agent was added, and in Comparative Example 2, the same amount of silver inorganic compound (Novaron IV1000 (Novaron IV1000 ( Toagosei Co., Ltd.)) was added to prepare each coating composition.
  • the obtained coating substrate is dried at room temperature for 12 hours, and further dried at 80 ° C. for 60 minutes, A urethane-urea resin-coated substrate comprising a urethane-urea resin coating layer and a glass substrate was produced.
  • Example 14-16 and Comparative Example 3 Production of water-based acrylic resin coating substrate
  • Water-based acrylic resin (“Boncoat CG-6150” manufactured by DIC Corporation) was added with the antibacterial and antiviral agents shown in Table 3 so that the metal content of the antibacterial and antiviral agent was 1% by mass of the solid content of the water-based acrylic resin. were blended to prepare each coating composition. After applying the prepared coating composition to a glass substrate using an applicator so that the wet film thickness is 152 ⁇ m, the obtained coating substrate is dried at room temperature for 12 hours, and further dried at 80 ° C. for 60 minutes, A water-based acrylic resin coating substrate was prepared comprising a water-based acrylic resin coating layer and a glass substrate.
  • Example 17 and Comparative Example 4 Production of urethane acrylate resin coating substrate
  • a urethane acrylate resin (“Luxidia 17-806" manufactured by DIC Corporation) was blended with the antibacterial and antiviral agent shown in Table 4 so that the metal content of the antibacterial and antiviral agent was 1% by mass of the solid content of the urethane acrylate resin.
  • a photoinitiator Irgacure 184 was blended so as to be 5% by mass of the resin solid content, and diluted with a solvent to prepare coating compositions.
  • the obtained coating substrate was dried at 60° C. for 5 minutes, and exposed to an irradiation dose of 200 mJ under a nitrogen atmosphere. /cm 2 to produce a coating substrate consisting of a urethane acrylate resin coating layer and a glass substrate.
  • Comparative Examples 1, 3, and 4 were blank test pieces that did not substantially contain antibacterial and antiviral agents, Examples 1-17 and Comparative Example 2 were antibacterial and antiviral coating test pieces, and the following antibacterial Viral and antibacterial tests were performed. The results are shown in Tables 1-4.
  • the antiviral evaluation was performed on bacteriophage Q ⁇ with reference to the film adhesion method of JIS R 1706:2020.
  • the virus inoculation action conditions on the surface of the blank test piece and the surface of the antibacterial and antiviral coated test piece were 4 hours at 25°C in the dark.
  • the antiviral activity value was calculated using the following formula from the bacteriophage Q ⁇ infectivity after 4 hours of reaction in the blank test piece and the antibacterial and antiviral coated test piece. Table 1 shows the results. If the antiviral activity value is 2.0 or more, it is evaluated as having an antiviral effect.
  • the antibacterial evaluation was performed using Sanai Biochecker FC (manufactured by Sanai Oil Co., Ltd.). Well water, which had been allowed to stand at room temperature for one week in advance, was dripped onto the medium surface of the San Biochecker, brought into contact with the coating layer of the coating substrate, and fixed with a masking tape. This sample was cultured at 30° C. for 2 days, and x was given when colonies were formed in any medium, and ⁇ was given when colonies were not formed in any medium.
  • the coating layer does not contain an antibacterial antiviral agent (the coating layer consists only of a binder resin). It was found that by adding the antibacterial and antiviral agent of the invention, antibacterial properties were obtained without impairing transparency.
  • the antibacterial and antiviral agent of Comparative Example 2 is a silver inorganic compound, Novaron IV1000 (manufactured by Toagosei Co., Ltd.), and since the antibacterial and antiviral agent of Comparative Example 2 is an inorganic compound, it is not compatible with urethane urea resin. , used a disper in the composition preparation to disperse the antibacterial and antiviral agents. In Comparative Example 2, cloudiness was observed in the coating layer obtained, indicating that the transparency of the coating layer was impaired.
  • Examples 18-19 and Comparative Example 5 Production of printed matter
  • a paint composition was prepared by adding the agent so that the amount of metal in the base paint was 0.5 mass % of the solid content of the base paint.
  • the prepared coating composition was printed on a corona-treated biaxially oriented polypropylene film (hereinafter referred to as OPP film) using a gravure proofing machine equipped with a gravure plate having a plate depth of 35 ⁇ m, and dried at 45° C. to obtain a printed material.
  • OPP film corona-treated biaxially oriented polypropylene film

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Abstract

L'invention concerne un agent antibactérien-antiviral qui a une activité antibactérienne-antivirale et qui a un effet moindre sur l'aspect d'un objet sur lequel l'agent est appliqué. En particulier, cet agent antibactérien-antiviral est un sel métallique d'acide gras et/ou un complexe métallique. Les métaux du sel métallique d'acide gras et du complexe métallique sont chacun indépendamment le lithium, le sodium, le potassium, le rubidium, le césium, le bore, le magnésium, l'aluminium, le calcium, le manganèse, le fer, le cobalt, le nickel, l'étain, l'antimoine, le cuivre, l'argent, le zinc, le molybdène, le vanadium, le strontium, le zirconium, le baryum, le bismuth, le plomb, l'or, le platine ou un élément des terres rares.
PCT/JP2022/021490 2021-06-15 2022-05-26 Agent antibactérien-antiviral, composition de revêtement antibactérienne-antivirale, stratifié, composition de résine antibactérienne-antivirale et article moulé WO2022264768A1 (fr)

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JP2023501483A JPWO2022264768A1 (fr) 2021-06-15 2022-05-26
JP2023138804A JP2023165705A (ja) 2021-06-15 2023-08-29 抗菌抗ウイルス剤、抗菌抗ウイルス性コーティング組成物、積層体、抗菌抗ウイルス性樹脂組成物および成形体

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WO2024122293A1 (fr) * 2022-12-08 2024-06-13 Dic株式会社 Agent de revêtement pour substrat en papier ou substrat en plastique et substrat en papier, substrat en plastique, récipient et matériau d'emballage ayant une couche de revêtement dudit agent de revêtement
WO2024128107A1 (fr) * 2022-12-13 2024-06-20 Dic株式会社 Mélange maître, composition de résine, article moulé et ses procédés de production
WO2024128008A1 (fr) * 2022-12-13 2024-06-20 Dic株式会社 Agent antibactérien et agent antiviral

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