WO2020203069A1 - Peinture pour la formation d'un film de revêtement antiviral, film de revêtement et film stratifié - Google Patents

Peinture pour la formation d'un film de revêtement antiviral, film de revêtement et film stratifié Download PDF

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Publication number
WO2020203069A1
WO2020203069A1 PCT/JP2020/009976 JP2020009976W WO2020203069A1 WO 2020203069 A1 WO2020203069 A1 WO 2020203069A1 JP 2020009976 W JP2020009976 W JP 2020009976W WO 2020203069 A1 WO2020203069 A1 WO 2020203069A1
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Prior art keywords
meth
mass
compound
coating film
film
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PCT/JP2020/009976
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English (en)
Japanese (ja)
Inventor
幹規 安藤
昌孝 毛利
大志 早田
朋和 長尾
中山　鶴雄
Original Assignee
リケンテクノス株式会社
株式会社Ｎｂｃメッシュテック
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Application filed by リケンテクノス株式会社, 株式会社Ｎｂｃメッシュテック filed Critical リケンテクノス株式会社
Priority to KR1020217031214A priority Critical patent/KR20210148148A/ko
Priority to CN202080027051.7A priority patent/CN113646392B/zh
Priority to JP2020538162A priority patent/JP6799200B1/ja
Publication of WO2020203069A1 publication Critical patent/WO2020203069A1/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
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • 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
    • C09D7/61—Additives non-macromolecular inorganic
    • 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 a paint capable of forming an antiviral coating film. More specifically, the present invention relates to a coating film capable of forming an antiviral coating film, a coating film formed by using the coating film, and a laminated film containing the coating film.
  • an antiviral agent capable of inactivating various viruses it is composed of iodine such as cuprous iodide (CuI) and elements of groups 8 to 15 of the 4th to 6th cycles of the periodic table.
  • An antiviral agent (see Patent Document 1) characterized by containing at least one type of iodide particles as an active ingredient, and a resin member using the antiviral agent (see Patent Document 2) have been proposed.
  • antiviral agents such as cuprous iodide (CuI) are added to paints, their antiviral properties are reduced, it is difficult to disperse the antiviral agents well in the paints, and they are formed. It was found that there are inconveniences such as insufficient transparency of the coating film to be applied.
  • a first object of the present invention is to provide a coating material capable of forming a coating film having antiviral properties.
  • a further object of the present invention is to provide a coating material having antiviral properties and capable of forming a coating film having excellent transparency.
  • A 100 parts by mass of polyfunctional (meth) acrylate;
  • B At least one compound selected from the group consisting of a monovalent copper compound and an iodide containing iodine in the 4th to 6th periods of the periodic table and elements of groups 8 to 15 0.1. ⁇ 150 parts by mass;
  • C1 A coating material for forming an antiviral coating film, which contains 0.1 to 20 parts by mass of a polyamine or a compound containing a polyamine structure. [3].
  • composition comprises the above component (A) polyfunctional (meth) acrylate and the above component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound in an amount of 100% by mass. , 100 parts by mass of the composition; (B) At least one compound 0.1 selected from the group consisting of a monovalent copper compound and an iodide containing iodine in the 4th to 6th periods of the periodic table and elements of groups 8 to 15.
  • a coating material for forming an antiviral coating which contains up to 150 parts by mass. [4]. At least one compound selected from the group consisting of the monovalent copper compound of the above component (B) and iodide containing iodine in the 4th to 6th periods of the periodic table and the elements of groups 8 to 15.
  • the laminated film according to item [5] above which satisfies the following characteristic (i): (I) When A Hong Kong influenza virus (A / Hong Kong / 8/68 (H3N2)) was allowed to act on the surface of the coating film of the laminated film at a temperature of 25 ° C. for 120 minutes, the logarithmic reduction value of the infectious titer was increased. 2 or more. [7].
  • the laminated film according to the above item [5] or [6] which satisfies the following characteristic (ii): (Ii)
  • the haze measured according to JIS K7136: 2000 is 2% or less. [8].
  • the coating film formed using the paint of the present invention has antiviral properties and is also excellent in transparency. Further, in the coating material of the present invention, the antiviral agent is well dispersed in the coating material, and the coating film can be formed industrially stably. Therefore, an article having a coating film formed on the surface using the coating film of the present invention, for example, a shatterproof film, a coating film as an infrared shielding film, or a window glass to which a laminated film containing the coating film is attached; display face plate protection. Smartphones, tablet terminals, etc.
  • the term "resin” is used as a term including a resin mixture containing two or more kinds of resins and a resin composition containing components other than the resin.
  • the term “film” is used interchangeably or interchangeably with “sheet”.
  • the terms “film” and “sheet” are used for those that can be industrially rolled up.
  • the term “board” is used for things that cannot be industrially rolled into rolls.
  • laminating a certain layer and another layer in order means directly laminating those layers and interposing one or more other layers such as an anchor coat between the layers. Includes both stacking.
  • the term "or more" related to a numerical range is used to mean a certain numerical value or a certain numerical value or more. For example, 20% or more means 20% or more than 20%.
  • the term “below” for a numerical range is used to mean a certain number or less than a certain number. For example, 20% or less means 20% or less than 20%.
  • the " ⁇ " symbol for a numerical range is used to mean a certain numerical value, more than a certain numerical value and less than another certain numerical value, or another certain numerical value.
  • some other numerical value is a numerical value larger than a certain numerical value. For example, 10-90% means 10%, more than 10% and less than 90%, or 90%.
  • the upper limit and the lower limit of the numerical range can be arbitrarily combined, and the embodiment in which the arbitrary combination can be read can be read. For example, “usually 10% or more, preferably 20% or more. On the other hand, usually 40% or less, preferably 30% or less.” Or “usually 10 to 40%, preferably 20” related to the numerical range of a certain characteristic. From the description "is up to 30%.”, It can be read that a certain characteristic is 10 to 40%, 20 to 30%, 10 to 30%, or 20 to 40% in one embodiment.
  • antiviral means both to inactivate a virus (reduce or lose (inactivate) the infectivity of the virus) and to suppress the growth of the virus. Used as a term to include.
  • the coating material of the present invention comprises (A) polyfunctional (meth) acrylate; (B) monovalent copper compound, and iodine and groups 4 to 6 and 8 of the periodic table. It contains at least one compound selected from the group consisting of iodides containing elements of Group 15; and (C) amine compounds.
  • the paint of the present invention comprises (A) a polyfunctional (meth) acrylate; (B) a monovalent copper compound, and iodine and groups 4 to 6 and groups 8 to 15 of the periodic table. At least one compound selected from the group consisting of iodides containing Group elements; and (C1) polyamines or compounds containing a polyamine structure.
  • the coating material of the present invention comprises (A) a polyfunctional (meth) acrylate; (B) a monovalent copper compound, and iodine and groups 4 to 6 and groups 8 to 15 of the periodic table. It comprises at least one compound selected from the group consisting of iodides containing Group elements; as well as (C2) N-substituted (meth) acrylamide compounds or N-vinyllactam compounds.
  • the coating material of the present invention comprises (A) a polyfunctional (meth) acrylate; (B) a monovalent copper compound, and iodine and groups 4 to 6 and groups 8 to 15 of the periodic table.
  • the paint of the present invention may further contain (D) a leveling agent in one of the other embodiments.
  • the above-mentioned component (A) polyfunctional (meth) acrylate is a (meth) acrylate having two or more (meth) acryloyl groups in one molecule.
  • the above-mentioned component (A) polyfunctional (meth) acrylate polymerizes and cures with active energy rays such as ultraviolet rays and electron beams to form a coating film.
  • the component (A) polyfunctional (meth) acrylate functions to include the component (B) monovalent copper compound and the like, and the component (C) amine compound.
  • component (A) polyfunctional (meth) acrylate examples include diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and polyethylene glycol di (meth).
  • (Meta) acryloyl groups such as acrylate, 2,2'-bis (4- (meth) acryloyloxypolyethylene oxyphenyl) propane, and 2,2'-bis (4- (meth) acryloyloxypolypropylene oxyphenyl) propane.
  • Bifunctional reactive monomer containing (meth) acryloyl group such as trimethylolpropane tri (meth) acrylate, trimethylol ethanetri (meth) acrylate, and pentaerythritol tri (meth) acrylate; pentaerythritol tetra (Meta) acryloyl group-containing tetrafunctional reactive monomer such as (meth) acrylate; (meth) acryloyl group-containing hexafunctional reactive monomer such as dipentaerythritol hexaacrylate; (meth) acryloyl group-containing 8 such as tripentaerythritol acrylate Examples thereof include a functionally reactive monomer and a polymer (oligoform or prepolymer) containing one or more of these as a constituent monomer.
  • component (A) polyfunctional (meth) acrylate examples include polyurethane (meth) acrylate, polyester (meth) acrylate, polyacrylic (meth) acrylate, polyepoxy (meth) acrylate, and polyalkylene glycol poly (meth) acrylate. , And prepolymers or oligomers such as polyester (meth) acrylates, which are two or more, for example bifunctional, trifunctional, tetrafunctional, hexafunctional, or octafunctional (meth) in one molecule. Those having an acryloyl group can be mentioned.
  • the term (meth) acrylate means acrylate or methacrylate.
  • component (A) polyfunctional (meth) acrylate one or a mixture of two or more of these can be used.
  • (B) Monovalent copper compounds and the like
  • the above components (B) From the group consisting of monovalent copper compounds and iodides containing iodine and elements in the 4th to 6th periods and groups 8 to 15 of the periodic table. At least one compound selected serves to develop antiviral properties.
  • Examples of the monovalent copper compound include cuprous chloride (CuCl), cuprous bromide (CuBr), cuprous iodide (CuI), cuprous acetate (Cu (CH 3 COO)), and the like. Examples thereof include cuprous sulfide (Cu 2 S), cuprous thiocyanate (CuSCN), and cuprous oxide (Cu 2 O).
  • Examples of iodide containing the above iodine and the elements of groups 8 to 6 and groups 8 to 15 in the periodic table include copper, silver, antimony, iridium, germanium, tin, thallium, platinum, palladium, and bismuth. , Gold, iron, cobalt, nickel, zinc, indium, and iodide such as mercury.
  • Examples of iodides containing the above iodine and the elements of groups 8 to 15 and groups 8 to 15 in the cycle table include cuprous iodide (CuI), ferrous iodide (AgI), and three.
  • cuprous chloride (CuCl), cuprous bromide (CuBr), cuprous iodide (CuI), cuprous thiocyanate (CuSCN), and iodide Copper (AgI) and tin tetraiodide (SnI 4 ) are preferred.
  • cuprous iodide (CuI) is more preferable.
  • the copper compound or the like of the above component (B) one kind or a mixture of two or more kinds of these can be used.
  • the shape of the copper compound or the like of the above component (B) is not particularly limited.
  • the shape of the component (B) may be preferably particle-like (including spherical, fibrous, scaly, ribbon-like, etc.) from the viewpoint of paint applicability.
  • the average particle size of the component (B) is usually 10 ⁇ m or less, preferably 5 ⁇ m or less, more preferably 3 ⁇ m from the viewpoint of coating film forming property. Hereinafter, it may be more preferably 1 ⁇ m or less.
  • the average particle size of the copper compound or the like of the component (B) may be usually 300 nm or less, preferably 200 nm or less, and more preferably 120 nm or less when it is desired to impart a clean and transparent feeling to the coating film.
  • the average particle size it may be usually 1 nm or more from the viewpoint of productivity when producing the copper compound or the like of the above component (B).
  • the average particle size of the particles is the particle size in which the accumulation from the smaller particle is 50% by mass in the particle size distribution curve measured by the laser diffraction / scattering method.
  • the particle size distribution curve can be measured using, for example, a laser diffraction / scattering particle size analyzer “MT3200II” (trade name) manufactured by Nikkiso Co., Ltd.
  • the blending amount of the copper compound or the like of the component (B) includes 100 parts by mass of the component (A) polyfunctional (meth) acrylate (the following component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound). In the embodiment, it is resistant to the above component (A) polyfunctional (meth) acrylate and the following component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound (total 100 parts by mass).
  • the blending amount of the copper compound or the like of the component (B) is usually 150 parts by mass or less from the viewpoint of maintaining the coatability of the paint and the transparency of the coating film with respect to 100 parts by mass of the reference component. It may be preferably 100 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less, and most preferably 40 parts by mass or less.
  • the above-mentioned component (C) amine compound functions to ensure that the copper compound or the like of the above-mentioned component (B) acts as an antiviral agent and exhibits antiviral properties.
  • the component (C) amine compound is selected from the group consisting of polyamines, compounds containing polyamine structures, N-substituted (meth) acrylamide compounds, and N-vinyllactam compounds in one of the typical embodiments. It may be at least one amine compound.
  • (C1) Polyamine or Compound Containing Polyamine Structure As a preferable example of the above-mentioned component (C) amine compound, a compound containing (C1) polyamine or polyamine structure can be mentioned.
  • a polyamine is a hydrocarbon compound having two or more amino groups in the molecule.
  • a compound having a polyamine structure is a compound containing at least one hydrocarbon group containing two or more amino groups in the molecule.
  • the "hydrocarbon” referred to herein may be an aliphatic hydrocarbon, an aromatic hydrocarbon, or an aliphatic and aromatic hydrocarbon, or a mixture thereof, but is typically an aliphatic hydrocarbon. ..
  • polyamines are also present in viruses and are involved in the synthesis of nucleic acids and proteins. Therefore, the virus may stay in the vicinity of the polyamine of the component (C1) or the compound containing the polyamine structure, and as a result, the chance of contacting the copper compound of the component (B) as an antiviral agent may increase. Expect.
  • the amine value of the polyamine of the component (C1) or the compound containing the polyamine structure depends on the blending amount of the component (C1) from the viewpoint of antiviral property, but is usually 1 mgKOH / g or more, preferably 10 mgKOH / g. As described above, it may be more preferably 20 mgKOH / g or more, further preferably 30 mgKOH / g or more, and most preferably 40 mgKOH / g or more.
  • the amine value of the polyamine of the above component (C1) or the compound containing the polyamine structure depends on the blending amount of the above component (C1) from the viewpoint of the pot life of the paint, but is usually 500 mgKOH / g or less, preferably 500 mgKOH / g or less. It may be 200 mgKOH / g or less.
  • the amine value is the number of mg of potassium hydroxide (KOH: molecular weight 56.11) equivalent to the acid required to neutralize 1 g of the sample.
  • KOH potassium hydroxide
  • the amine value is calculated by dissolving 5 g of a sample in 50 mL of ethanol (95) and titrating with a 0.5 mol / L hydrochloric acid aqueous solution by an electric titration method (potentiometric titration).
  • the amine value of the polyamine or the compound containing the polyamine structure used in the examples of the present specification is a value calculated by this method by the supplier.
  • the blending amount of the polyamine of the component (C1) or the compound containing the polyamine structure includes 100 parts by mass of the component (A) polyfunctional (meth) acrylate (the following component (C2) N-substituted (meth) acrylamide compound and the like.
  • 0.1 part by mass or more is usually preferable, from the viewpoint of surely expressing antiviral property with respect to 100 parts by mass in total of the above component (A) and the following component (C2). It may be 0.5 parts by mass or more, more preferably 1 part by mass or more, further preferably 2 parts by mass or more, and most preferably 3 parts by mass or more.
  • the blending amount of the polyamine of the component (C1) or the compound containing the polyamine structure is usually 20 parts by mass or less, preferably 15 parts by mass or less, with respect to 100 parts by mass of the reference component from the viewpoint of suppressing bleed whitening. , More preferably 10 parts by mass or less.
  • N- substituted (meth) acrylamide compound such as the component (C) an amine compound
  • C2 N- substituted (meth) acrylamide compound or N- vinyl lactam compound may be mentioned (C2) N- substituted (meth) acrylamide compound or N- vinyl lactam compound.
  • the "N-substituted (meth) acrylamide compound” means an N-substituted acrylamide compound or an N-substituted methacrylamide compound.
  • the component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound has polymerizability.
  • the above-mentioned component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound can be blended in a large amount in the coating material so as to surely exhibit antiviral properties.
  • the component (C2) N-substituted (meth) acrylamide compound is not particularly limited, but typically may be a compound having a structure represented by the following general formula (1).
  • R 1 represents a hydrogen atom or a methyl group.
  • R 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and
  • R 3 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or an amino group.
  • R 2 and R 3 together form a 5- or 6-membered hydrocarbon ring, which may have an oxygen atom as a ring member, together with the nitrogen atom to which they are bonded.
  • N-substituted (meth) acrylamide compound examples include N-methyl (meth) acrylamide, N-methylol (meth) acrylamide butyl ether, N-ethyl (meth) acrylamide, and Nn-propyl (meth).
  • (meth) acryloyl morpholine is preferable, and acryloyl morpholine is more preferable.
  • the component (C2) N-vinyllactam compound include N-vinyl-2-pyrrolidone and N-vinyl- ⁇ -caprolactam.
  • the component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound one kind or a mixture of two or more kinds thereof can be used.
  • the blending amount of the component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound is 100% by mass based on the sum of the component (A) polyfunctional (meth) acrylate and the component (C2). From the viewpoint of surely expressing the antiviral property, it is usually 1% by mass or more (99% by mass or less of the above component (A)), preferably 5% by mass or more (95% by mass or less of the above component (A)), more preferably 10. It may be mass% or more (90% by mass or less of the component (A)), more preferably 15% by mass or more (85% by mass or less of the component (A)).
  • the blending amount of the component (C2) N-substituted (meth) acrylamide compound or N-vinyllactam compound is such that the surface hardness of the formed coating film and the scratch resistance are higher than 100 parts by mass of the reference component.
  • it is usually 60% by mass or less (40% by mass or more of the above component (A)), preferably 50% by mass or less (50% by mass or more of the above component (A)), more preferably 45% by mass or less (the above component (A)). ) 55% by mass or more), more preferably 40% by mass or less (60% by mass or more of the above component (A)).
  • the coating material of the present invention preferably further contains (D) a leveling agent from the viewpoint of smoothing the surface of the coating film.
  • the component (D) leveling agent examples include acrylic leveling agents, silicone-based leveling agents, fluorine-based leveling agents, silicone-acrylic copolymer-based leveling agents, fluorine-modified acrylic-based leveling agents, and fluorine-modified silicone-based leveling agents.
  • a leveling agent in which a functional group for example, an alkoxy group such as a methoxy group or an ethoxy group, an acyloxy group, a halogen group, an amino group, a vinyl group, an epoxy group, a methacryloxy group, an acryloxy group, an isocyanate group, etc.
  • a silicone-acrylic copolymer system leveling agent is preferable.
  • the component (D) leveling agent one or a mixture of two or more of these can be used.
  • the blending amount of the above component (D) leveling agent is not particularly limited because it is an optional component.
  • the compounding amount of the component (D) leveling agent (if present) is 100 parts by mass of the component (A) polyfunctional (meth) acrylate (the embodiment containing the component (C2) N-substituted (meth) acrylamide compound and the like.
  • it is usually 0.01 part by mass or more, preferably 0. It may be 0.05 parts by mass or more, more preferably 0.1 parts by mass or more.
  • the blending amount of the component (D) leveling agent is usually 3 parts by mass or less, preferably 2 parts by mass or less, more preferably 2 parts by mass or less from the viewpoint of suppressing troubles due to bleeding out with respect to 100 parts by mass of the reference component. It may be 1 part by mass or less, more preferably 0.5 part by mass or less.
  • the coating material of the present invention is diluted to a concentration that is easy to apply, it may contain a solvent, if desired.
  • the solvent reacts with the component (A) polyfunctional (meth) acrylate, the component (B) copper compound, the component (C) amine compound, and other optional components, or self-reactions (deterioration) of these components. It is not particularly limited as long as it does not catalyze (promote) (including the reaction).
  • Examples of the solvent include 1-methoxy-2-propanol, 2-propanol, ethanol, ethyl acetate, n-butyl acetate, toluene, methyl ethyl ketone, methyl isobutyl ketone, diacetone alcohol, and acetone.
  • the coating material of the present invention is not particularly limited, but may further contain (or may not include) the following optional components.
  • the optional component include a polymerizable compound other than the above component (A) and the above component (C2) such as methyl (meth) acrylate and styrene, an antiviral agent other than the above component (B), an antibacterial agent, and an erasing agent.
  • the blending amount of the optional component may be usually 10 parts by mass or less, or about 0.01 to 10 parts by mass, with the polyfunctional (meth) acrylate as 100 parts by mass.
  • the paint of the present invention can be obtained by mixing and stirring these components.
  • the laminated film of the present invention includes an antiviral coating film formed using the paint of the present invention.
  • an antiviral coating film formed by using the coating film of the present invention usually constitutes the surface of at least one side of the laminated film.
  • the laminated film of the present invention typically has a layer of an antiviral coating film and a resin film formed by using the coating film of the present invention, and a surface that becomes a surface in an actual use state is the above-mentioned antiviral property. It is composed of a coating film.
  • the actual use state is a state in which the laminated film of the present invention is used as a member of various articles (for example, a state in which a shatterproof film is attached to a window glass or the like; a decorative sheet is a surface of the article. (The state used for the decoration of).
  • the paint of the present invention has been described above.
  • the method for forming the antiviral coating film using the coating material of the present invention is not particularly limited, and a known web coating method can be used. Examples of the above method include rod coating, roll coating, gravure coating, reverse coating, roll brushing, dip coating, spray coating, spin coating, air knife coating, and die coating.
  • a rod coat is preferable from the viewpoint of making the thickness of the antiviral coating film uniform, and a rod coat using a Mayer bar as a rod (hereinafter, may be abbreviated as "Meyer bar method"). ) Is more preferable.
  • the thickness of the antiviral coating film is not particularly limited and may be any thickness as desired.
  • the thickness of the antiviral coating film is usually 0.1 ⁇ m or more, preferably 0.5 ⁇ m or more, more preferably 1 ⁇ m or more, still more preferably 1.5 ⁇ m, from the viewpoint of antiviral property, weather resistance, and scratch resistance. That may be the above.
  • it is usually 60 ⁇ m or less, preferably 30 ⁇ m or less, more preferably 20 ⁇ m or less, still more preferably 10 ⁇ m or less. You can.
  • the normal and preferable range group of the thickness of the antiviral coating film in the laminated film described here also applies to the case where the coating film constitutes a part or all of the surface of the article as a single layer film.
  • the layer of the resin film is made of an arbitrary resin film and is a layer serving as a film base material for forming the antiviral coating film.
  • the resin film include polyvinyl chloride resins; polyester resins such as aromatic polyesters and aliphatic polyesters; polyolefin resins such as polyethylene, polypropylene, and polymethylpentene; acrylic resins; polycarbonate resins; poly.
  • (Meta) acrylicimide-based resin polystyrene, acrylonitrile-butadiene-styrene copolymer resin (ABS resin), styrene / ethylene / butadiene / styrene copolymer, styrene / ethylene / propylene / styrene copolymer, and styrene / ethylene -Styrene resins such as ethylene / propylene / styrene copolymers; cellulose resins such as cellophane, triacetyl cellulose, diacetyl cellulose, and acetyl cellulose butyrate; polyvinylidene chloride resins; fluororesins such as vinylidene fluoride In addition, resin films such as polyvinyl alcohol, ethylene vinyl alcohol, polyether ether ketone, nylon, polyamide, polyimide, polyurethane, polyetherimide, polysul
  • the thickness of the resin film is not particularly limited and can be any thickness as desired.
  • the thickness of the resin film is usually preferably 10 ⁇ m or more from the viewpoint of handleability and conforming to the standard as a glass shatterproof film. May be 30 ⁇ m or more, more preferably 50 ⁇ m or more.
  • the thickness of the resin film in this application may be usually 250 ⁇ m or less, preferably 150 ⁇ m or less, and more preferably 100 ⁇ m or less from the viewpoint of economy.
  • the thickness of the resin film may be usually 200 ⁇ m or more, preferably 300 ⁇ m or more, and more preferably 400 ⁇ m or more. Further, the thickness of the resin film in this application may be usually 1500 ⁇ m or less, preferably 1000 ⁇ m or less, and more preferably 700 ⁇ m or less from the viewpoint of meeting the demand for thinning of the article.
  • An anchor is placed on the antiviral coating film-forming surface of the resin film before the antiviral coating film is formed in order to enhance the adhesion between the resin film layer and the antiviral coating film.
  • a coat may be formed.
  • the resin film and the antiviral coating film may be directly laminated without forming an anchor coat.
  • the resin film preferably has high transparency.
  • a transparent resin film having high transparency and no coloring is more preferable.
  • the total light transmittance of the transparent resin film may be usually 80% or more, preferably 85% or more, more preferably 88% or more, and further preferably 90% or more. Higher total light transmittance is preferable.
  • the total light transmittance is measured according to JIS K7136: 2000.
  • the turbidity meter "NDH2000" (trade name) of Nippon Denshoku Industries Co., Ltd. can be used.
  • the yellowness index of the transparent resin film may be usually 5 or less, preferably 3 or less, more preferably 2 or less, and further preferably 1 or less. The lower the yellowness index, the better.
  • the yellowness index can be measured using a chromaticity meter "SolidSpec-3700" (trade name) manufactured by Shimadzu Corporation in accordance with JIS K7105: 1981.
  • the transparent resin film examples include cellulose ester resins such as triacetyl cellulose; polyester resins such as polyethylene terephthalate; cyclic hydrocarbon resins such as ethylene norbornene copolymers; polymethyl methacrylate, polyethyl methacrylate, and the like. And acrylic resins such as vinylcyclohexane and methyl (meth) acrylate copolymers; aromatic polycarbonate resins; polyolefin resins such as polypropylene and 4-methyl-pentene-1; polyamide resins; polyarylate resins; Examples thereof include polymer-type urethane acrylate-based resins; and films such as polyimide-based resins. These films include non-stretched films, uniaxially stretched films, and biaxially stretched films. Further, these films include a multilayer film in which one or more of these are laminated in two or more layers.
  • the resin film may be colored or opaque. It may be well or transparent.
  • the laminated film of the present invention reduces the logarithmic titer of the infectious titer when the surface of the coating film and A Hong Kong influenza virus (A / Hong Kong / 8/68 (H3N2)) are allowed to act at a temperature of 25 ° C. for 120 minutes.
  • the value may be preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more. From the viewpoint of antiviral property, it is preferable that the logarithmic reduction value of the infectious titer is high.
  • the logarithmic reduction value of the infectious titer is measured according to the measuring method (i) antiviral property of the following Examples.
  • the haze of the laminated film of the present invention may be usually 3% or less, preferably 2% or less, and more preferably 1% or less. A low haze is preferable from the viewpoint of obtaining a clean and transparent feeling.
  • the total light transmittance of the laminated film of the present invention may be usually 80% or more, preferably 85% or more, more preferably 88% or more, still more preferably 90% or more. Higher total light transmittance is preferable.
  • the total light transmittance and haze are measured according to JIS K7136: 2000. Examples of the device used for the measurement include the turbidity meter "NDH2000" (trade name) of Nippon Denshoku Industries Co., Ltd.
  • FIG. 1 is a conceptual diagram of a cross section showing an example of the laminated film of the present invention.
  • the laminated film of the embodiment shown in FIG. 1 is used as an infrared shielding film.
  • the laminated film of the present embodiment has an antiviral coating film 1, a first anchor coat 2, and a transparent thermoplastic resin formed by using the coating film of the present invention in order from the side of the surface that becomes the surface in an actual use state. It has a film layer 3, a second anchor coat 4, a coating film 5 having an infrared shielding function, and an adhesive layer 6.
  • FIG. 2 is a conceptual diagram of a cross section showing another example of the laminated film of the present invention.
  • the laminated film of the embodiment shown in FIG. 2 is used as a decorative sheet.
  • the laminated film of the present embodiment has an antiviral coating film 1 formed by using the coating film of the present invention, a transparent thermoplastic resin film layer 3, and a printing layer in order from the side of the surface that becomes the surface in an actual use state. 7. It has a layer 8 of a thermoplastic resin film that is colored and has a hiding property, and a pressure-sensitive adhesive layer 6.
  • Articles of the present invention include antiviral coatings formed using the paints of the present invention.
  • an antiviral coating film formed by using the paint of the present invention usually constitutes a part or all of the surface of the article.
  • the article of the present invention is an article in which the laminated film of the present invention is used as a member in a typical embodiment (for example, a window glass to which a shatterproof film is attached, furniture decorated with a decorative sheet). You can.
  • the article of the present invention covers part or all of the surface of a three-dimensionally shaped substrate of the article (eg, housing of an electrical product, instrument panel of an automobile, etc.).
  • An antiviral coating film may be formed using the coating material of the present invention.
  • the coating film may be formed by directly coating the substrate, or may be formed by laminating a single layer or a laminated film containing the coating film.
  • a dip coating, a spray coating, a spin coating, an air knife coating or the like is used as a method for forming an antiviral coating film on a part or all of the surface of the substrate by using the coating material of the present invention.
  • Examples thereof include a method of forming a coating film by repeatedly applying the coating material of the present invention once or twice or more.
  • the method for molding the substrate include so-called three-dimensional molding methods such as membrane press molding, pressure press molding, vacuum molding, and vacuum pressure air molding; injection molding, blow molding, etc. of the thermoplastic resin. And a method of extrusion molding; and a method of injecting a curable resin into a mold having a desired shape and curing the resin.
  • Antiviral property (i-1) Measurement of infectious titer of antiviral film The test was performed according to the method of ISO 21702 “Measurement of antiviral activity on plastic and non-porous surfaces”. Specifically, a 5 cm ⁇ 5 cm test piece is collected from a laminated film (antiviral film), placed in a plastic cave, and on the surface of the antiviral coating film of the test piece, A Hong Kong influenza virus ( 100 ⁇ L of A / Hong Kong / 8/68 (H3N2)) virus solution (hereinafter sometimes referred to as “stock solution”) was added dropwise and allowed to act at room temperature (25 ° C.) for 120 minutes.
  • H3N2 Hong Kong influenza virus
  • the upper surface of the test piece was covered with a polyethylene terephthalate film (size 4 cm ⁇ 4 cm).
  • 10 mL of SCDLP medium was added, and the virus was washed out by pipetting to stop the action.
  • the amount of virus solution after concentration to become 10 -2 to 10 -5 stock solution each action of virus solution after each action, the 10 2 to 10 5 times the amount of the dropped solution (100 [mu] L) Dilute with MEM diluted solution (until the same concentration as the above), and add the sample solution (5 types of undiluted solution, virus solution 10-2 , 10-3 , 10-4 , and 10-5 ). Created.
  • sample solution 100 ⁇ L of the sample solution was inoculated into MDCK cells (Madin-Darby canine kidney cell) cultured in a 6-well plate petri dish, and allowed to stand for 60 minutes to adsorb the virus to the MDCK cells.
  • MDCK cells Mesdin-Darby canine kidney cell
  • a 0.7 mass% agar medium was layered, and after culturing at a temperature of 34 ° C. and 5% CO 2 for 48 hours using an incubator, formalin fixation and methylene blue staining were performed, and the number of plaques formed was counted. From the results of each sample solution, the common logarithm of the virus infectious titer (PFU (Plaque-forming unit) /0.1 mL) was calculated.
  • PFU Plaque-forming unit
  • (I-2) Production of control film
  • the following component (A-1) 154 parts by mass (100 parts by mass in terms of solid content), the following component (C1-1) 5 parts by mass, the following component (D-1) 1 part by mass ( (0.1 part by mass in terms of solid content), 3 parts by mass of the following component (E-1), 140 parts by mass of the following component (E-2), and 60 parts by mass of the following component (E-3) are mixed and stirred to form a control film.
  • a paint for forming a coating film was obtained.
  • the paint was applied onto one side of Toray Industries, Inc.'s 50 ⁇ m-thick double-sided easy-adhesive biaxially stretched polyethylene terephthalate resin film “Lumirror” (trade name) using a Mayer bar coating device.
  • the film was applied so as to have a thickness of 2 ⁇ m after curing, dried, and cured by irradiation with ultraviolet rays to form a coating film to obtain a control film.
  • logarithm reduction value The difference between the common logarithm of the infectious titer of the control film and the common logarithm of the infectious value of the antiviral film (hereinafter, may be referred to as “logarithm reduction value”) is the antiviral property. Calculated as an index.
  • the logarithmic reduction value of 3 means that the infectious titer of the antiviral film was 1/1000 of the infectious titer of the control film.
  • Pencil hardness According to JIS K5600-5-4: 1999, using the pencil "Uni” (trade name) of Mitsubishi Pencil Co., Ltd. under the condition of 200 g load, about the surface of the antiviral coating film of the antiviral film. Pencil hardness was measured.
  • Category 2 The coating was peeled off along the edges of the cut and / or at the intersection. The area affected by the cross-cut portion clearly exceeded 5% but never exceeded 15%.
  • Category 3 The coating film was partially or wholly peeled off along the edges of the cut, and / or various parts of the eye were partially or wholly peeled off. The area affected by the cross-cut portion clearly exceeded 15% but never exceeded 35%.
  • Category 4 The coating film was partially or wholly peeled along the edge of the cut, and / or several eyes were partially or wholly peeled. The area affected by the cross-cut portion clearly exceeded 35% but did not exceed 65%.
  • Category 5 When the degree of peeling exceeded Category 4, it was classified as this category.
  • B Monovalent copper compounds, etc.
  • B-1 Commercially available cuprous iodide (CuI) powder (manufactured by Wako Pure Chemical Industries, Ltd.) is pre-dispersed in ethanol, then crushed and dispersed by a bead mill. A cuprous iodide slurry having an average particle size of 120 nm was obtained. This was adjusted to a solid content of 11% by mass.
  • CuI cuprous iodide
  • C' Comparative component (C'-1) Dispersant and phosphate ester "DISPERBYK-110" (trade name) of Big Chemie Japan Co., Ltd. Contains no polyamine structure. Solid content 52% by mass.
  • D Leveling agent (D-1) Silicone / acrylic copolymerization system leveling agent "Disparon NSH-8430HF” (trade name) of Kusumoto Kasei Co., Ltd. Solid content 10% by mass.
  • E Other Ingredients
  • E-1 Phenylketon-based Photopolymerization Initiator (1-Hydroxycyclohexylphenylketon) "SB-PI714" (trade name) of Soho Kogyo Co., Ltd. Solid content 100% by mass.
  • E-2) Methyl isobutyl ketone.
  • E-3) 1-methoxy-2-propanol.
  • Example 1 Preparation of paint for forming an antiviral coating film 154 parts by mass of the above component (A-1) (100 parts by mass in terms of solid content), 100 parts by mass of the above component (B-1) (11 parts by mass in terms of solid content) , 5 parts by mass of the above component (C1-1), 1 part by mass of the above component (D-1) (0.1 part by mass in terms of solid content), 3 parts by mass of the above component (E-1), and the above component (E-2). ) 140 parts by mass and 60 parts by mass of the above component (E-3) were mixed and stirred to obtain a coating material for forming an antiviral coating film.
  • Examples 2-7 A laminated film was formed and physical property tests / evaluations were carried out in the same manner as in Example 1 except that the coating composition was changed as shown in Table 1. In each case, a laminated film having a good appearance could be stably produced. The above tests (i) to (ix) were performed. The results are shown in Table 1.
  • the coating material of the present invention it was considered that the above-mentioned component (B) as an antiviral agent was well dispersed in the coating material. Further, the coating film formed by using the coating film of the present invention has antiviral properties and is also excellent in transparency. Further, the adhesion to the film substrate, heat aging resistance, and moisture heat resistance were also good. On the other hand, the antiviral property of the example not containing the above component (C) was not sufficient.
  • the above (i-2) is used as a control film in accordance with JIS Z2801: 2010 to cover the surface of the coating film.
  • the antibacterial activity value of Staphylococcus aureus was measured under the condition that the bacterial solution was dropped onto the film, and the value was 4.5.
  • the antibacterial activity value of Escherichia coli was measured and found to be 5.8.
  • the laminated film of Example 1 is treated with the light resistance treatment category 1 of SIAA (Antibacterial Product Technology Council)
  • the above (i-2) is used as a control film in accordance with JIS Z2801: 2010, and the surface of the coating film is used.
  • the antibacterial activity value of Staphylococcus aureus was measured under the condition that the bacterial solution was dropped onto the film, and the value was 3.6. Similarly, when the antibacterial activity value for Escherichia coli was measured, the value was 4.3. Therefore, it was considered that a laminated film having a coating film formed by using the paint of the present invention can obtain the antibacterial mark of SIAA (Antibacterial Product Technology Council).
  • SIAA Antibacterial Product Technology Council
  • the above-mentioned antibacterial activity value is usually 2 or more, preferably 2.5 or more, more preferably 3 or more, and further preferably 3. From the viewpoint of acquiring the antibacterial mark of SIAA (Antibacterial Product Technology Council). It may be 5 or more. Higher antibacterial activity values are preferred.
  • the SEK mark textile product certification standard JEC301 No. 1 of the Japan Textile Evaluation Technology Council, except that the test sample size was 200 cm 2 and the measurement time (leaving time) was 24 hours.
  • Chapter 6-4 Deodorant Test 21.
  • the odor reduction rate (unit:%) of hydrogen sulfide was measured according to the detector tube method of the deodorant test, and the value was 66%.
  • the odor reduction rate of acetic acid was measured, the value was 60%.
  • the odor reduction rate of ammonia was measured, the value was 52%.
  • the odor reduction rate of acetaldehyde was measured and found to be 26%.
  • the odor reduction rate may be usually 20% or more, preferably 50% or more, more preferably 60% or more, still more preferably 70% or more from the viewpoint of deodorizing performance. The higher the odor reduction rate is, the more preferable.
  • the laminated film (antiviral film) having a coating film formed by using the coating film of the present invention is not only useful for antiviral use but also for antibacterial use and deodorant use.
  • Anti-virus coating film 2 First anchor coat 3: Layer of transparent thermoplastic resin film 4: Second anchor coat 5: Coating film having infrared shielding function 6: Adhesive layer 7: Printing layer 8 : Layer of thermoplastic resin film that is colored and has concealing properties

Abstract

La présente invention concerne une peinture qui est destinée à la formation d'un film de revêtement antiviral et qui contient (A) un (méth)acrylate polyfonctionnel ; (B) au moins un composé choisi dans le groupe constitué par les composés du cuivre monovalent et les iodures contenant de l'iode et un élément des quatrième à sixième périodes et des groupes 8 à 15 du tableau périodique ; et (C) au moins un composé amine choisi dans le groupe constitué par les polyamines, les composés contenant une structure polyamine, les composés (méth)acrylamides N-substitués et les composés N-vinyl-lactames. Le composé qui est le composant (B) peut contenir de l'iodure de cuivre(I). L'invention concerne également un film stratifié comprenant un film de revêtement formé à l'aide de la peinture, le film de revêtement formant au moins une surface du film stratifié. (i) Il est préférable que lorsque le virus de la grippe A de Hong Kong (A/Hong Kong/8/68 (H3N2)) est appliqué sur la surface du film de revêtement du film stratifié à une température de 25 °C pendant 120 minutes, la valeur de réduction logarithmique de son titre infectieux est supérieure ou égale à 2.
PCT/JP2020/009976 2019-04-04 2020-03-09 Peinture pour la formation d'un film de revêtement antiviral, film de revêtement et film stratifié WO2020203069A1 (fr)

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CN202080027051.7A CN113646392B (zh) 2019-04-04 2020-03-09 抗病毒涂膜形成用涂料、涂膜以及层压膜
JP2020538162A JP6799200B1 (ja) 2019-04-04 2020-03-09 抗ウイルス性塗膜形成用塗料、塗膜、及び積層フィルム

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