Antibacterial and antiviral agent, antibacterial and antiviral coating composition, laminate, antibacterial and antiviral resin composition and molded article

Abstract

Provided is an antibacterial-antiviral agent that has antibacterial-antiviral activity and that has a lesser effect on the appearance of an object to which the agent is applied. Specifically, this antibacterial-antiviral agent is a fatty acid metal salt and / or a metal complex. Metals of the fatty acid metal salt and the metal complex 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 a rare-earth element.

Description

[Technical field]

[0001] 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. [Background technology]

[0002] The spread of COVID-19 has rapidly increased people's awareness of hygiene. There is also a growing global need for "antibacterial and antiviral" products for daily necessities to reduce the possibility of infection with pathogens and viruses. For example, there is a strong demand for antibacterial and antiviral properties on surfaces such as the exterior and touch panels of smartphones, handrails, doorknobs, washbasins, various push buttons such as elevator buttons, and the interiors of public transportation, as these are expected to be used multiple times throughout the day.

[0003] As an antibacterial and antiviral agent, photocatalysts (TiO 2 These metals or metal compounds are directly applied to the target object, or mixed with a binder resin to form a coating composition, which is then applied to the target object. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2019-182846 A Summary of the Invention [Problem to be solved by the invention]

[0005] When inorganic metal compounds, which are conventional antibacterial and antiviral agents, are directly applied to the target, the color of the target changes, and the target has a rough texture. Even when a coating composition is made of an inorganic metal compound and a binder resin, the coating layer obtained from the coating composition has a cloudy color due to the inorganic metal compound, and when the binder resin is a transparent resin, the transparency is impaired. In addition, in a composition containing an inorganic metal compound, the inorganic compound is generally in powder form, so a dispersion treatment is required, which is a problem from the viewpoint of productivity.

[0006] The problem to be solved by the present invention is to provide an antibacterial and antiviral agent that has high compatibility with resins and antibacterial and antiviral activity, and has a reduced effect on the appearance of the target to which it is applied. [Means for solving the problem]

[0007] As a result of intensive research aimed at solving the above problems, the inventors have found that the effect on the appearance of an application target can be reduced by making the antibacterial and antiviral agent into the form of a fatty acid metal salt or a metal complex, and have completed the present invention.

[0008] That is, the present invention relates to an antibacterial and antiviral agent which is one or more selected from the group consisting of a fatty acid metal salt, a metal complex of a heteroatom-containing ligand and a metal ion, and a metal complex of a heteroatom-containing ligand and a fatty acid metal salt, wherein the metal of the fatty acid metal salt, the metal complex of a heteroatom-containing compound ligand and a metal ion, and the metal complex of a heteroatom-containing compound ligand and a 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 a rare earth. Effect of the Invention

[0009] The present invention can provide an antibacterial and antiviral agent that has high compatibility with resins and antibacterial and antiviral activity, and has a reduced effect on the appearance of the target object. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] An embodiment of the present invention will be described below. The present invention is not limited to the following embodiment, and can be implemented by making appropriate modifications within the scope that does not impair the effects of the present invention.

[0011] [Antibacterial and antiviral agents] The antibacterial and antiviral agent of the present invention is one or more types 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, wherein the metals in the fatty acid metal salts, the metal complexes of heteroatom-containing compound ligands and metal ions, and the metal complexes of heteroatom-containing compound ligands and fatty acid metal salts 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 a rare earth.

[0012] The antibacterial and antiviral agent of the present invention takes the form of a fatty acid metal salt or metal complex, and due to the antibacterial and antiviral properties of the metal and the high compatibility of the fatty acid or complex ligand with organic substances, it is considered that when added to a coating composition containing a binder resin, it imparts antibacterial and antiviral properties to the resulting coating layer and simultaneously reduces the effect on appearance, such as the impairment of transparency of the coating layer by the antibacterial and antiviral agent.

[0013] In the present invention, "antibacterial" means to include the effect of reducing the number of bacteria, the effect of inactivating bacteria, the effect of reducing the infectivity of bacteria, etc. Similarly, in the present invention, "antiviral" means to include the effect of reducing the number of viruses, the effect of inactivating viruses, the effect of reducing the infectivity of viruses, etc.

[0014] In the present invention, the target bacteria for antibacterial treatment are not particularly limited, and may be either bacteria or fungi. Examples of bacteria include gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Salmonella, Moraxella, Legionella, etc.; gram-positive bacteria such as Staphylococcus aureus and Clostridium bacteria, etc. Examples of fungi include yeasts such as Candida, Rhodotorula, and baker's yeast; and molds such as red mold and black mold.

[0015] In the present invention, the viruses to be treated against are not particularly limited, and may be any of the known enveloped viruses (viruses having an envelope) and non-enveloped viruses (viruses not having an envelope).

[0016] Examples of the enveloped viruses include coronavirus, influenza virus, rubella virus, Ebola virus, measles virus, varicella-zoster virus, herpes virus, mumps virus, arbovirus, RS virus, SARS virus, hepatitis virus (e.g., hepatitis A 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, lyssavirus, etc.

[0017] Examples of the non-enveloped viruses include adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, polyomavirus, BK virus, rhinovirus, and feline calicivirus.

[0018] The antibacterial and antiviral agent of the present invention will be described below.

[0019] (Fatty acid metal salts) 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).

[0020] [ka] (In the 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 earth.

[0021] In the general formula (1), when n1 is an integer of 2 or more, a plurality of R 1 may be the same as or different from each other.

[0022] R 1 The alkyl group having 1 to 21 carbon atoms may be a straight-chain alkyl group, a branched alkyl group, or may contain an alicyclic structure.

[0023] R 1 The hydrogen atom or the alkyl group having 1 to 21 carbon atoms is R 1It corresponds to a carboxylic acid residue obtained by removing a carboxyl group (COOH) from a carboxylic acid having 1 to 22 carbon atoms represented by COOH. Examples of the 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, acrylic acid residue, methacrylic acid residue, octylic acid residue (2-ethylhexanoic acid residue), neodecanoic acid residue, naphthenic acid residue, isononanoic acid residue, tung oil acid residue, tall oil fatty acid residue, coconut oil fatty acid residue, soybean oil fatty acid residue, linseed oil fatty acid residue, safflower oil fatty acid residue, dehydrated castor oil fatty acid residue, tung oil fatty acid residue, lauric acid residue, myristic acid residue, palmitic acid residue, stearic acid residue, isostearic acid residue, and oleic acid residue.

[0024] R 1 From the viewpoint of adhesion to substrates described below, the alkyl group having 1 to 21 carbon atoms is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 11 carbon atoms. R 1 is preferably a formic acid residue, an acetic acid residue, a propionic acid residue, a butanoic acid residue, a pentanoic acid residue, a hexanoic acid residue, a 2-ethylbutyric acid residue, a heptanoic acid residue, an octanoic acid residue, a 2-ethylhexanoic acid residue, an isononanoic acid residue, a neodecanoic acid residue, a naphthenic acid residue, a stearic acid residue, or an oleic acid residue.

[0025] 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 a rare earth, preferably bismuth, neodymium, magnesium, cobalt, copper, silver, zinc, lead, yttrium, lanthanum, praseodymium, samarium or gadolinium, more preferably bismuth, neodymium, magnesium, cobalt, silver, copper, lead, yttrium, lanthanum, praseodymium, samarium or gadolinium. If the metal in the fatty acid metal salt is bismuth, neodymium, magnesium, lanthanum, gadolinium, or samarium, coloration due to the addition of an antibacterial and antiviral agent can be made less likely to occur.

[0026] In the present invention, rare earth refers to one or more elements selected from scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and lutetium (Lu).

[0027] n1 is M 1 This is a value determined by the ionic valence of the metal atom, for example, M 1 If is boron, n1 is 3, and M 1 If is cobalt, then n1 is 2.

[0028] The fatty acid metal salt which is the antibacterial and antiviral agent of the present invention also includes a form of fatty acid metal borate. The fatty acid metal borate is, for example, a compound represented by the following general formula (2).

[0029] [ka] (In the general formula (2), R 2 is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms, M 2 is boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum, or rare earth.

[0030] In the general formula (2), R 2 The alkyl group having 1 to 21 carbon atoms is R 1Similarly, in the general formula (2), M 2 The metal is M in the general formula (1). 1 is the same as the metal.

[0031] When a fatty acid metal salt is used as the antibacterial and antiviral agent of the present invention, a single fatty acid metal salt may be used alone, or two or more fatty acid metal salts having mutually different structures may be used.

[0032] The fatty acid metal salt can be produced by a known method, or a commercially available product may be used.

[0033] (Metal Complexes) 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 compounds in which a metal ion or a fatty acid metal salt and a heteroatom-containing ligand form a complex through a coordinate bond.

[0034] As the metal ion with which the heteroatom-containing ligand forms a metal complex, the same metal ion as that of the fatty acid metal salt explained as the antibacterial and antiviral agent of the present invention can be used. As the fatty acid metal salt in which the heteroatom-containing ligand forms a metal complex, the same fatty acid metal salts as those explained as the antibacterial and antiviral agent of the present invention can be used.

[0035] The heteroatom-containing ligand that forms the metal complex may be a ligand having one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and phosphorus in the molecule. Examples of 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'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenoxyethanol, , imidazole, 1-methylimidazole, 2-methylimidazole, 4-methylimidazole, 2,4-dimethylimidazole, 1,4-diethylimidazole, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-(N-phenyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropylmethyldimethoxysilane, tetramethylammonium hydroxide, 8-quinolinol , 5-chloro-8-quinolinol, 2,2'-bipyridyl and its derivatives, 2,2'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenol and its derivatives, 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-tert-octylphenol] and other amine compounds; trioctylmethylammonium chloride, trioctylmethylammonium acetate and other quaternary ammonium salts; trimethylphosphine, tributylphosphine, triphenylphosphine and other phosphine compounds; tetramethylphosphonium chloride, tetraethylphosphonium chloride, tetrapropylphosphonium chloride, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, trimethyl(2-hydroxypropyl)phosphonium chloride, triphenylphosphonium chloride, benzylphosphonium chloride and other phosphonium salts; thiolactic acid, 2-aminothiophenol, 2,2'-dithiodianiline and other sulfur-based compounds.

[0036] The heteroatom-containing ligand is preferably one or more amine ligands selected from 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'-bipyridyl and its derivatives, and 2,2'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenol and its derivatives.

[0037] The heteroatom-containing ligand that forms the metal complex may be of one type alone or of two or more types having mutually different structures.

[0038] In the metal complex, the ratio (molar ratio) of the metal ion or fatty acid metal salt to the heteroatom-containing ligand is, for example, in the range of 0.1 to 12 mol, preferably 0.3 to 10 mol, and more preferably 0.5 to 10 mol, of the heteroatom-containing ligand per 1 mol of the metal atom of the metal ion or fatty acid metal salt.

[0039] When the metal ion in the metal complex is an aluminum ion, the aluminum complex is preferably one or more selected from 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).

[0040] [ka] (In the general formulas (3-1) and (3-2), R 311 ~R 316 and R 321 ~R 326 are each independently an alkyl group having 1 to 22 carbon atoms or an alkoxy group having 1 to 22 carbon atoms.

[0041] R 311 ~R 316 and R 321 ~R 326 The alkylene group portion of the alkyl group having 1 to 22 carbon atoms and the alkoxy group having 1 to 22 carbon atoms may be linear or branched, or may contain an alicyclic structure. 311 ~R 316 and R 321 ~R 326 The alkyl group and the alkylene group portion of the alkoxy group preferably have 1 to 9 carbon atoms.

[0042] R 311 ~R 316 and R 321 ~R 326 The alkyl group having 1 to 22 carbon atoms is preferably a methyl group or an ethyl group.

[0043] R 311 ~R 316 and R 321 ~R 326 The alkoxy group having 1 to 22 carbon atoms is preferably a methoxy group, an ethoxy group, or an oleyloxy group.

[0044] Specific examples of aluminum chelate compounds include aluminum tris(acetylacetonate), aluminum tris(ethylacetoacetate), aluminum monoacetylacetonate bis(ethylacetoacetate), aluminum monoacetylacetonate bisoleylacetoacetate, ethylacetoacetate aluminum diisopropylate, and alkylacetoacetate aluminum diisopropylate.

[0045] The antibacterial and antiviral agent of the present invention is preferably a water-insoluble antibacterial and antiviral agent. When the antibacterial and antiviral agent is water-insoluble, the antibacterial and antiviral agent has excellent durability of antibacterial and antiviral properties even when exposed to water such as rain in daily life. In the present application, "water-insoluble" means that the amount of water required to dissolve 1 g of the antibacterial and antiviral agent at 20°C is 10 ml or more.

[0046] 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 antibacterial and antiviral agents, can be produced by a known method, and can be produced by reacting a simple metal or a fatty acid metal salt with a heteroatom-containing ligand. In addition, the metal complex may be a commercially available product.

[0047] [Coating composition] The coating composition of the present invention contains the antibacterial and antiviral agent of the present invention and a binder resin. Since the antibacterial and antiviral agent of the present invention has high compatibility with the binder resin, the coating layer obtained from the coating composition containing the antibacterial and antiviral agent of the present invention can reduce the impact on the appearance, such as the loss of transparency caused by the antibacterial and antiviral agent. In addition, the antibacterial and antiviral agent of the present invention can exhibit an adhesion promoting effect with the substrate, and the coating layer containing the antibacterial and antiviral agent of the present invention can exhibit high adhesion with the substrate. Therefore, in the laminate of the substrate and the coating layer laminated on the substrate, the coating layer exhibits antibacterial and antiviral properties, and at the same time, the substrate and the coating layer can exhibit high adhesion.

[0048] 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 may be contained in a range of 0.01 to 30 parts by mass per 100 parts by mass of the resin solid content, preferably in a range of 0.01 to 15 parts by mass per 100 parts by mass of the resin solid content, more preferably in a range of 0.01 to 10 parts by mass per 100 parts by mass of the resin solid content, and even more preferably in a range of 0.1 to 10 parts by mass per 100 parts by mass of the resin solid content. The term "resin solid content" as used herein means the total amount of solid content such as binder resin contained in the coating composition.

[0049] The coating composition of the present invention may contain one type of antibacterial and antiviral agent of the present invention, or two or more types of agents.

[0050] The binder resin contained in the coating composition of the present invention is not particularly limited, and any type of resin, such as an emulsion-based resin, a latex-based resin, a thermosetting resin, or an active energy ray-curable resin, can be used.

[0051] The binder resin may be either a water-based resin or a water-insoluble resin (solvent-based resin). In this application, the term "water-soluble resin" means that the amount of water required to dissolve 1 g of the resin at 20° C. is less than 10 ml. The term "water-insoluble resin" refers to a resin other than the above-mentioned "water-soluble resin."

[0052] Specific examples of binder resins include acrylic resin, vinyl acetate resin, styrene resin, vinyl chloride resin, olefin resin, urethane resin, urea resin, urethane urea resin, acrylic urethane resin, epoxy resin, melamine resin, phenol resin, polyester resin, alkyd resin, silicone resin, polyphenylene sulfide resin, acrylonitrile / styrene copolymer resin, acrylonitrile / butadiene copolymer resin, and acrylonitrile / butadiene / styrene copolymer (ABS) resin. The binder resin includes modified versions of the above resins, and for example, in the case of a phenolic resin, it also includes a rosin-modified phenolic resin.

[0053] The binder resin contained in the coating composition of the present invention may be one type alone or two or more types.

[0054] The content of the binder resin in the coating composition of the present invention is not particularly limited, and may be appropriately set within the range of, for example, 10 to 100% by mass based on the total mass of the resin solid content of the coating composition.

[0055] The coating composition of the present invention only needs to contain the antibacterial and 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-based medium.

[0056] Specific examples of the dispersion medium include water, 1-butanol, isobutanol, 1-pentanol, 2-methyl-2-pentanol, 3-methyl-3-pentanol, methyl ethyl ketone, methanol, ethanol, n-propyl alcohol, isopropyl alcohol and other monofunctional alcohols, 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- Diols such as nonanediol, 1,10-decanediol, 1,12-dodecanediol, propylene glycol, 1,2 butanediol, 3-methyl-1,3 butanediol, 1,2 pentanediol, 2-methyl-1,3 propanediol, 1,2 hexanediol, dipropylene glycol, and diethylene glycol; aromatic diols which are bisphenol A and alkylene oxide adducts having 2 or 3 carbon atoms (average molar addition number of 1 to 16) of bisphenol A; hydrogenated bisphenol A, etc. alicyclic diol polyoxypropylene-2,2-bis(4-hydroxyphenyl)propane, polyoxyethylene-2,2-bis(4-hydroxyphenyl)propane, cyclohexanediol, ethylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monoisobutyl ether, propylene glycol monomethyl ether, propylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, ethyl carbitol, γ-butyrolactone, and various fatty acids.

[0057] The dispersion medium contained in the coating composition of the present invention may be one type alone or two or more types.

[0058] The content of the dispersion medium in the coating composition of the present invention is not particularly limited, and may be appropriately set so that the solid content of the coating composition is in the range of 30 to 80 mass %, for example.

[0059] The coating composition of the present invention may further contain a plasticizer. By adding a plasticizer to the coating composition, it is possible to impart flexibility to the resulting coating layer and improve its conformability to the substrate.

[0060] The plasticizer is not particularly limited, and examples thereof include phthalate esters, non-aromatic dibasic acid esters, aliphatic esters, esters of polyalkylene glycols, phosphate esters, trimellitic acid esters, chlorinated paraffin, hydrocarbon oils, process oils, polyethers, epoxy plasticizers, polyester plasticizers, and the like, with phthalate esters being preferred. Specific examples of plasticizers include dibutyl phthalate, diheptyl phthalate, di(2-ethylhexyl) phthalate, dioctyl phthalate, dioctyl adipate, dioctyl sebacate, dibutyl sebacate, isodecyl succinate, tricresyl phosphate, tributyl phosphate, epoxidized soybean oil, and benzyl epoxy stearate.

[0061] The coating composition of the present invention may contain one type of plasticizer alone or two or more types of plasticizers.

[0062] The content of the plasticizer in the coating composition of the present invention is not particularly limited, and may be appropriately set within the range of, for example, 0.1 to 50 parts by mass per 100 parts by mass of the resin solid content of the coating composition.

[0063] The coating composition of the present invention only needs to 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. Examples of such other additives include pigments, matting agents, curing agents, curing accelerators, defoamers, dispersants, leveling agents, thickeners, antioxidants, weather resistance agents, flame retardants, antistatic agents, lubricants, preservatives, etc.

[0064] The coating composition of the present invention is applied to the surface of a substrate, and the resulting coating film is subjected to a curing method (such as heat curing or active energy ray curing) suitable for the binder resin, thereby forming a coating layer.

[0065] Regarding the method for applying the coating composition, any known and commonly used coating method can be used, such as a roll coater, electrostatic coating, a bar coater, a gravure coater, a knife coater, dipping coating, spray coating, and the like.

[0066] 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, nonwoven fabric, gypsum board, wooden board, and resin substrate.

[0067] Specific examples of 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: unstretched 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-based resin film, cyclic olefin-based resin film, polyimide resin film, polyvinyl fluoride resin film, polyvinylidene fluoride resin film, ethylene-vinyl acetate copolymer film, and the like. The resin substrate used may be subjected to a surface treatment such as a corona treatment.

[0068] [Resin composition] The resin composition of the present invention contains the antibacterial and 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 applications, but also for molding into a molded article that exhibits antibacterial and antiviral properties.

[0069] The resin contained in the resin composition of the present invention may be the same as the binder resin contained in the coating composition of the present invention. In addition, the resin composition of the present invention may contain the same components as those that can be contained in the coating composition of the present invention.

[0070] The resin composition of the present invention can be molded by any molding method suitable for the resin used, including melt molding methods such as injection molding, extrusion molding, pressure molding (press molding), compressed air molding, and vacuum molding, and casting methods.

[0071] The coating layer obtained by using the coating composition of the present invention and the molded article obtained by 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. The applicable uses are wide-ranging, including the exterior of smartphones, the exterior of personal computers, touch panels, handrails, doorknobs, washstands, push buttons such as elevator buttons, interior furnishings (wallpaper, flooring, etc.), various packaging materials, various textile products, and medical equipment (medical gloves, medical glasses, etc.). EXAMPLES

[0072] The present invention will be specifically described below with reference to examples and comparative examples. However, the present invention is not limited to the following examples.

[0073] (Synthesis Example 1: Preparation of fatty acid metal salt (Cu)) 217.1 parts by mass of neodecanoic acid and 36.0 parts by mass of sodium hydroxide were reacted at 80° C., and 100.0 parts by mass of copper sulfate was further added and reacted at 80° C. The by-product sodium sulfate was washed with water, and then dehydrated under reduced pressure at 130° C., and 76.2 parts by mass of petroleum hydrocarbon was added to obtain 301.6 parts by mass of a neodecanoic acid copper solution (fatty acid metal salt (Cu)). The copper content in the obtained fatty acid metal salt (Cu) was 8% by mass.

[0074] (Synthesis Example 2: Preparation of fatty acid metal salt (Co)) 319.0 parts by mass of 2-ethylhexanoic acid and 100.0 parts by mass of cobalt hydroxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 134.2 parts by mass of a petroleum hydrocarbon was added to obtain 502.3 parts by mass of a 2-ethylhexanoic acid cobalt solution (fatty acid metal salt (Co)). The cobalt content in the obtained fatty acid metal salt (Co) was 12% by mass.

[0075] (Synthesis Example 3: Preparation of fatty acid metal salt (Nd)) 224.8 parts by mass of neodecanoic acid and 60.0 parts by mass of neodymium oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 306.9 parts by mass of cyclohexane was added to obtain 570.0 parts by mass of a neodymium neodecanoate solution (fatty acid metal salt (Nd)). The neodymium content in the obtained fatty acid metal salt (Nd) was 8.8% by mass.

[0076] (Synthesis Example 4: Preparation of fatty acid metal salt (Bi)) 330.6 parts by mass of 2-ethylhexanoic acid and 125.0 parts by mass of bismuth oxide were reacted at 130° C., and then dehydrated under reduced pressure at 130° C. to obtain 439.5 parts by mass of a bismuth 2-ethylhexanoate solution (fatty acid metal salt (Bi)). The bismuth content in the obtained fatty acid metal salt (Bi) was 25% by mass.

[0077] (Synthesis Example 5: Preparation of fatty acid metal salt (Mg)) 461.4 parts by mass of 2-ethylhexanoic acid, 71.9 parts by mass of magnesium hydroxide, and 411.4 parts by mass of petroleum hydrocarbon were reacted at 110°C, and after dehydration under reduced pressure at 90°C, 35.9 parts by mass of butyl diglycol was added to obtain 1000 parts by mass of magnesium 2-ethylhexanoate solution (fatty acid metal salt (Mg)). The magnesium content in the obtained fatty acid metal salt (Mg) was 3.0% by mass.

[0078] (Synthesis Example 6: Preparation of fatty acid metal salt (La)) 83.1 parts by mass of neodecanoic acid and 21.5 parts by mass of lanthanum oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 107.6 parts by mass of cyclohexane was added to obtain 208.5 parts by mass of lanthanum neodecanoate solution (fatty acid metal salt (La)). The lanthanum content in the obtained fatty acid metal salt (La) was 8.8% by mass.

[0079] (Synthesis Example 7: Preparation of fatty acid metal salt (Pr)) 166.6 parts by mass of neodecanoic acid and 45.0 parts by mass of praseodymium oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 220.0 parts by mass of cyclohexane was added to obtain 422.0 parts by mass of a praseodymium neodecanoate solution (fatty acid metal salt (Pr)). The praseodymium content in the obtained fatty acid metal salt (Pr) was 8.8% by mass.

[0080] (Synthesis Example 8: Preparation of fatty acid metal salt (Sm)) 137.1 parts by mass of neodecanoic acid and 37.6 parts by mass of samarium oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 196.3 parts by mass of cyclohexane was added to obtain 364.7 parts by mass of a samarium neodecanoate solution (fatty acid metal salt (Sm)). The samarium content in the obtained fatty acid metal salt (Sm) was 8.8% by mass.

[0081] (Synthesis Example 9: Preparation of fatty acid metal salt (Gd)) 149.3 parts by mass of neodecanoic acid and 43.0 parts by mass of gadolinium oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 230.2 parts by mass of cyclohexane was added to obtain 415.1 parts by mass of a gadolinium neodecanoate solution (fatty acid metal salt (Gd)). The gadolinium content in the obtained fatty acid metal salt (Gd) was 8.8% by mass.

[0082] (Synthesis Example 10: Preparation of fatty acid metal salt (Nd2)) 192.8 parts by mass of 2-ethylhexanoic acid and 60.0 parts by mass of neodymium oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 338.5 parts by mass of cyclohexane was added to obtain 581.6 parts by mass of a neodymium 2-ethylhexanoate solution (fatty acid metal salt (Nd2)). The neodymium content in the obtained fatty acid metal salt (Nd2) was 8.8% by mass.

[0083] (Synthesis Example 11: Preparation of metal complex (Mn)) 50 parts by mass of 8-hydroxyquinoline was added to a solution of 291 parts by mass of manganese neodecanoate solution (Mn: 6.5% by mass) and 1235 parts by mass of benzyl alcohol, and the mixture was reacted at 50° C. for 1 hour to obtain 1576 parts by mass of a complex solution of manganese neodecanoate and 8-hydroxyquinoline (metal complex (Mn)). The manganese content in the obtained metal complex (Mn) was 1.2% by mass.

[0084] In addition to the above, commercially available fatty acid metal salts, yttrium 2-ethylhexanoate (Y), lead 2-ethylhexanoate (Pb), and silver 2-ethylhexanoate (Ag), were prepared (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.).

[0085] (Examples 1-13 and Comparative Examples 1-2: Production of urethane urea resin coated substrate) An antibacterial and antiviral agent shown in Tables 1 and 2 was mixed with a urethane urea resin (DIC Corporation's "Burnoc EPL-925") so that the metal content of the antibacterial and antiviral agent was 1 mass% of the solid content of the urethane urea resin, to prepare each coating composition. In Comparative Example 1, no antibacterial and antiviral agent was added, and in Comparative Example 2, a silver inorganic compound (Novalon IV1000 (Toagosei Co., Ltd.)) was added in the same amount as the solid content (NV.51 mass%) of the fatty acid metal salt (Cu) added in Example 1, to prepare each coating composition. The prepared coating composition was applied onto a glass substrate using an applicator to a wet film thickness of 152 μm, and the resulting coated substrate was then dried at room temperature for 12 hours and then further dried at 80° C. for 60 minutes to produce a urethane urea resin coated substrate consisting of a urethane urea resin coating layer and a glass substrate.

[0086] (Examples 14-16 and Comparative Example 3: Preparation of Water-Based Acrylic Resin Coated Substrate) The antibacterial and antiviral agents shown in Table 3 were each mixed into an aqueous acrylic resin ("Boncoat CG-6150" manufactured by DIC Corporation) so that the metal content of the antibacterial and antiviral agent was 1 mass% of the solid content of the aqueous acrylic resin, to prepare coating compositions. The prepared coating compositions were applied to a glass substrate using an applicator to a wet film thickness of 152 μm, and the resulting coated substrate was dried at room temperature for 12 hours and then further dried at 80° C. for 60 minutes to produce an aqueous acrylic resin coated substrate consisting of an aqueous acrylic resin coating layer and a glass substrate.

[0087] (Example 17 and Comparative Example 4: Production of urethane acrylate resin coated substrate) The antibacterial and antiviral agents shown in Table 4 were blended into a urethane acrylate resin ("Luxidia 17-806" manufactured by DIC Corporation) so that the metal content of the antibacterial and antiviral agent was 1% by mass of the solid content of the urethane acrylate resin, and a photoinitiator Irgacure 184 was further blended therein so that the metal content was 5% by mass of the solid content of the resin, followed by dilution with a solvent to prepare coating compositions. The prepared coating compositions were applied to a glass substrate using a bar coater to a wet film thickness of 30 μm, and the resulting coated substrate was dried at 60° C. for 5 minutes and exposed to a dose of 200 mJ / cm under a nitrogen atmosphere. 2 The resin was cured with a solvent such as ethyl acetate or ethyl alcohol to produce a coated substrate consisting of a urethane acrylate resin coating layer and a glass substrate.

[0088] The produced coated substrates were subjected to the following antiviral and antibacterial tests, with Comparative Examples 1, 3, and 4 being blank test pieces substantially not containing an antibacterial or antiviral agent, and Examples 1-17 and Comparative Example 2 being antibacterial and antiviral coated test pieces. The results are shown in Tables 1-4.

[0089] (Antiviral test) The antiviral evaluation was conducted against bacteriophage Qβ, using the film adhesion method of JIS R 1706:2020 as a reference. The virus was inoculated onto the surfaces of the blank test piece and the antibacterial and antiviral coated test piece for 4 hours at 25°C in a dark place. The antiviral activity value was calculated using the following formula from the bacteriophage Qβ infectivity value after 4 hours of reaction on the blank test piece and the antibacterial and antiviral coated test piece. The results are shown in Table 1. An antiviral activity value of 2.0 or higher is evaluated as having an antiviral effect. V = Log(A / B) = Log(A) - Log(B) V: Antiviral activity value Log(A): Common logarithm of the infectivity value after 4 hours of reaction on a blank test piece Log(B): Common logarithm of the infectivity value after 4 hours of reaction of the antibacterial and antiviral coating test piece

[0090] (Antibacterial Test) Antibacterial evaluation was performed using a San-ai Biochecker FC (manufactured by San-ai Oil Co., Ltd.). Well water that had been left at room temperature for one week was dropped onto the medium surface of the San-ai Biochecker, brought into contact with the coating layer of the coating substrate, and fixed with masking tape. This sample was cultured at 30°C for two days, and samples that formed colonies on either medium were marked with an ×, and samples that did not form colonies on either medium were marked with an ○.

[0091] (Transparency test) The transparency of the coating layer of the produced coated substrate was visually confirmed and evaluated according to the following criteria. ○: No turbidity observed ×: Turbidity is observed

[0092] [Table 1]

[0093] [Table 2]

[0094] [Table 3]

[0095] [Table 4]

[0096] In Tables 1-4, in Comparative Examples 1, 3, and 4, the coating layer did not contain an antibacterial and antiviral agent (the coating layer consisted of only a binder resin), and in comparison, in Examples 1-17 of the present application, it was found that by adding the antibacterial and antiviral agent of the present invention, antibacterial properties were obtained without impairing transparency. The antibacterial and antiviral agent of Comparative Example 2 was Novalon IV1000 (manufactured by Toagosei Co., Ltd.), an inorganic silver compound, and since the antibacterial and antiviral agent of Comparative Example 2 is an inorganic compound, it is not compatible with the urethane urea resin, and a disperser was used to prepare the composition in order to disperse the antibacterial and antiviral agent. In Comparative Example 2, cloudiness was confirmed in the obtained coating layer, and it was found that the transparency of the coating layer was impaired.

[0097] (Examples 18-19 and Comparative Example 5: Production of printed matter) A coating composition was prepared by adding the antibacterial and antiviral agent shown in Table 5 to a base coating containing 15.0 g of urethane urea resin, 30.0 g of white ink mill base, and 36.0 g of a mixed organic solvent (EtAc / IPA = 60 / 40 (mass ratio)) such that the metal amount of the antibacterial and antiviral agent was 0.5 mass% of the solids content of the base coating. 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 with a plate depth of 35 μm, and dried at 45° C. to obtain a print. The obtained print was evaluated as follows.

[0098] (Adhesion evaluation) The produced prints were left to stand for one day, after which cellophane tape was applied to the printed surface and then quickly peeled off, and the appearance of the print film was visually evaluated according to the following criteria. A: The printing film did not peel off at all. B: 50-80% of the printed film remained on the film. C: Less than 50% of the printed film remained on the film.

[0099] [Table 5]

[0100] The results in Table 5 show that the adhesion of the coating layer to the substrate is improved by adding the antibacterial and antiviral agent of the present invention.

Claims

1. An antibacterial and antiviral coating composition comprising an antibacterial and antiviral agent which is a fatty acid metal salt and a binder resin, the metal of the fatty acid metal salt is bismuth, manganese, neodymium, magnesium, lanthanum, praseodymium, samarium or gadolinium; The antibacterial and antiviral coating composition, wherein the fatty acid of the fatty acid metal salt is propionic acid, butanoic acid, pentanoic acid, hexanoic acid, 2-ethylbutyric acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, isononanoic acid or neodecanoic acid.

2. 2. The antibacterial and antiviral coating composition according to claim 1, wherein the binder resin is at least one selected from the group consisting of acrylic resins, vinyl acetate resins, styrene resins, vinyl chloride resins, olefin resins, urethane resins, urea resins, urethane urea resins, epoxy resins, melamine resins, phenolic resins, polyester resins, alkyd resins, silicone resins, acrylonitrile / styrene copolymer resins, and acrylonitrile / butadiene copolymer resins.

3. 3. The antibacterial and antiviral coating composition according to claim 1, wherein the metal derived from the antibacterial and antiviral agent is contained in an amount of 0.01 to 30 parts by mass per 100 parts by mass of resin solids.

4. A laminate having a coating layer of the antibacterial and antiviral coating composition according to any one of claims 1 to 3 and a substrate.

5. The laminate of claim 4, wherein the coating layer is transparent.

6. An antibacterial and antiviral resin composition containing an antibacterial and antiviral agent which is a fatty acid metal salt and a resin, the metal of the fatty acid metal salt is bismuth, manganese, neodymium, magnesium, lanthanum, praseodymium, samarium or gadolinium; The antibacterial and antiviral resin composition, wherein the fatty acid of the fatty acid metal salt is propionic acid, butanoic acid, pentanoic acid, hexanoic acid, 2-ethylbutyric acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, isononanoic acid or neodecanoic acid.

7. A molded article obtained by molding the antibacterial and antiviral resin composition according to claim 6.

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