Anti-biofilm agent, Anti-biofilm coating composition, laminate, Anti-biofilm resin composition, and molded body

Abstract

To provide an anti-biofilm agent having high compatibility with a resin and high anti-biofilm properties, and having reduced influence on the appearance of an application target.SOLUTION: An anti-biofilm agent comprising a fatty acid metal salt of a fatty acid having 1 to 22 carbon atoms and a metal, wherein the metal is copper, bismuth, zinc, magnesium, cobalt, or a rare earth.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an anti-biofilm agent, an anti-biofilm coating composition, a laminate, an anti-biofilm resin composition, and a molded article. [Background technology]

[0002] A "biofilm" is a structure formed when microorganisms such as bacteria and mold attach to the surface of a material and produce polymeric substances such as polysaccharides on the surface. This structure known as a biofilm is likely to form in environments with a lot of moisture, such as kitchens, toilets, drains, and drainage pipes, where microorganisms can easily grow. The so-called "slimy" substance is also a biofilm, and is believed to be the cause of bad odors and other problems.

[0003] Once a biofilm is formed, it becomes difficult to sufficiently remove the viscous polymeric substances such as polysaccharides produced by microorganisms simply by washing with a cleaning solution or scrubbing. Therefore, an effective countermeasure against biofilms is to inhibit the formation of biofilms themselves, and various methods have been proposed (e.g., Patent Documents 1-4). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 56-150011 [Patent Document 2] Japanese Patent Application Publication No. 05-155726 [Patent Document 3] Japanese Patent Application Laid-Open No. 2012-072266 [Patent Document 4] Patent Publication No. 2021-046385 Summary of the Invention [Problem to be solved by the invention]

[0005] The anti-biofilm agent in Patent Document 1 uses a chlorine-based compound, which has the problem of corroding metals, for example, around the kitchen. Patent Document 2 uses the photocatalytic effect of a titanium oxide coating to suppress biofilm formation, but it cannot be applied to places where sunlight does not reach, and there is a problem that the titanium oxide causes surface opacity. Patent Document 3 uses polyamino acids as the active ingredient, but because these polyamino acids are highly water-soluble, there is a problem that they leach out from the application site. Patent Document 4 uses composite microparticles of polyamino acids and polycarboxylic acids to overcome the weaknesses of these polyamino acids, but there is a problem that they cause opacity on the application surface.

[0006] The problem to be solved by the present invention is to provide an anti-biofilm agent that has high compatibility with resins and high anti-biofilm properties, and that has a reduced effect on the appearance of the object to which it is applied. Another problem to be solved by the present invention is to provide an anti-biofilm coating composition that can be used to form an anti-biofilm coating without damaging the surface appearance. Another problem to be solved by the present invention is to provide a laminate and a molded article that can exhibit anti-biofilm properties without impairing the surface appearance. [Means for solving the problem]

[0007] As a result of intensive research to solve the above problems, the inventors discovered that an anti-biofilm agent containing a specific fatty acid metal salt exhibits high anti-biofilm properties while ensuring high compatibility with resins, and thus completed the present invention.

[0008] That is, the present invention relates to the following anti-biofilm agents, etc. 1. An anti-biofilm agent comprising a fatty acid metal salt of a fatty acid having 1 to 22 carbon atoms and a metal, wherein the metal is copper, bismuth, zinc, magnesium, cobalt, or a rare earth. 2. The anti-biofilm agent according to 1, wherein the fatty acid is 2-ethylhexanoic acid, neodecanoic acid, isononanoic acid, naphthenic acid, lauric acid, stearic acid, palmitic acid, isostearic acid or oleic acid. 3. The anti-biofilm agent according to 1 or 2, wherein the metal is bismuth or a rare earth. 4. An anti-biofilm coating composition comprising the anti-biofilm agent according to any one of 1 to 3 and a binder resin. 5. The anti-biofilm coating composition according to 4, wherein the binder resin is one or more selected from the group consisting of acrylic resin, vinyl acetate resin, styrene resin, vinyl chloride resin, olefin resin, urethane resin, urea resin, urethane urea resin, epoxy resin, melamine resin, phenolic resin, polyester resin, alkyd resin, silicone resin, acrylonitrile / styrene copolymer resin, and acrylonitrile / butadiene copolymer resin. 6. The anti-biofilm coating composition according to 4 or 5, which contains the metal derived from the anti-biofilm agent in a range of 0.01 to 30 parts by mass per 100 parts by mass of resin solid content. 7. A laminate having a substrate and a coating layer of the anti-biofilm coating composition according to any one of 4 to 6. 8. An anti-biofilm resin composition comprising the anti-biofilm agent according to any one of 1 to 3 and a resin. 9. A molded body obtained by molding the anti-biofilm resin composition described in 8. [Effects of the Invention]

[0009] The present invention can provide an anti-biofilm agent that has high compatibility with resins, high anti-biofilm properties, and reduced impact on the appearance of the target to which it is applied. The present invention can provide an anti-biofilm coating composition that can be used to form an anti-biofilm coating without damaging the surface appearance. The present invention can provide a laminate and a molded article that can exhibit anti-biofilm properties without impairing the surface appearance. DETAILED DESCRIPTION OF THE INVENTION

[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. The compounds in this specification may be derived from fossil resources or biological resources.

[0011] [Anti-biofilm agent] The anti-biofilm agent of the present invention can suppress the formation of biofilms at the site where it is applied. Biofilms are primarily formed in moist or water-contacting environments, but the anti-biofilm agent of the present invention contains a fatty acid metal salt, and because fatty acid metal salts having a fatty chain are highly water-resistant, they can exert an anti-biofilm effect over a long period of time. Furthermore, fatty acid metal salts having a fatty chain have high compatibility with binder resins, so the anti-biofilm agent does not precipitate from the coating portion described below, damaging the appearance.

[0012] Biofilm-forming microorganisms are known to synthesize and release quorum-sensing (QS) signaling substances. These QS signaling substances detect the presence of other microorganisms, and when the signaling substances reach a certain concentration, the microorganisms stimulated by the signal produce polymeric substances such as polysaccharides and aggregate to form a biofilm. Therefore, inhibiting the synthesis and / or release of QS signaling substances is one key to suppressing biofilm formation.

[0013] Examples of microorganisms that form biofilms include Rhizobium, Pseudomonas, Sphingomonas, Sphingopyxis, Sphingobium, Brevundimonas, Blastomonas, Stenotrophomonas, and Porphyromonas. onas, Aeromonas, Klebsiella, Flavobacterium, Ochrobactrum, Methylobacterium, Fusobacterium, Brevibacterium, Burkholderia, Enterobacter, Acinetobacter Acinetobacter, Citrobacter, Aggregatibacter, Rhodobacter, Erwinia, Escherichia, Ralstonia, Salmonella, Serratia, Yersinia, Acidovorax, Prevotella Known examples of bacteria include gram-negative bacteria such as Staphylococcus (commonly known as "staphylococcus"), Streptococcus, Enterococcus, Bacillus, Lactobacillus, and Deinococcus.

[0014] The anti-biofilm agent of the present invention will be described below.

[0015] (Fatty acid metal salts) The anti-biofilm agent of the present invention contains a fatty acid metal salt of a fatty acid having 1 to 22 carbon atoms and a metal, and the metal is copper, bismuth, zinc, magnesium, cobalt, or a rare earth. Hereinafter, the fatty acid metal salt may be referred to as the "fatty acid metal salt of the present invention."

[0016] The fatty acid metal salt of the present invention is preferably a compound represented by the following general formula (1).

[0017] [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 copper, bismuth, zinc, magnesium, cobalt or a rare earth.

[0018] 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.

[0019] R 1 The alkyl group having 1 to 21 carbon atoms may be a linear alkyl group, a branched alkyl group, or may contain an alicyclic structure. R 1 The alkyl group having 1 to 21 carbon atoms may have one or more carbon-carbon unsaturated bonds.

[0020] R 1 The hydrogen atom or alkyl group having 1 to 21 carbon atoms is used in the production of the fatty acid metal salt. 1It corresponds to a carboxylic acid residue obtained by removing the 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.

[0021] R 1 The alkyl group having 1 to 21 carbon atoms is preferably an alkyl group having 1 to 18 carbon atoms, and more preferably an alkyl group having 7 to 11 carbon atoms.

[0022] R 1 is preferably a 2-ethylhexanoic acid residue, a neodecanoic acid residue, an isononanoic acid residue, a naphthenic acid residue, a lauric acid residue, a stearic acid residue, a palmitic acid, an isostearic acid residue, or an oleic acid residue, and from the viewpoint of transparency, is more preferably a 2-ethylhexanoic acid residue, a neodecanoic acid residue, an isononanoic acid residue, a naphthenic acid residue, or an isostearic acid residue.

[0023] M 1 The rare earth element in this specification means 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).

[0024] M 1is preferably bismuth or a rare earth, more preferably bismuth, lanthanum or neodymium. 1 When the anti-biofilm agent is made of these metals, it is possible to suppress the coloring caused by the metal and ensure high transparency.

[0025] n1 is M 1 is a value determined by the ionic valence of the metal atom, for example, M 1 If is bismuth, n1 is 3, and M 1 If is neodymium, n1 is 3.

[0026] The fatty acid metal salt contained in the anti-biofilm agent of the present invention may be one type alone, or may be two or more types of fatty acid metal salts that are structurally different from each other.

[0027] The anti-biofilm agent of the present invention may contain the fatty acid metal salt of the present invention, and may, for example, consist essentially of the fatty acid metal salt of the present invention. Here, "consist essentially of" means that the content of the fatty acid metal salt is 90% by mass or more, 95% by mass or more, 98% by mass or more, or 100% by mass of the total amount of the anti-biofilm agent of the present invention.

[0028] The fatty acid metal salt of the present invention can be produced by a known method, and commercially available products may also be used.

[0029] (metal complexes) The fatty acid metal salt of the present invention may be in the form of a metal complex coordinated with a heteroatom-containing ligand.

[0030] The heteroatom-containing ligand that forms the metal complex may be a ligand that contains one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and phosphorus in the molecule. Examples of such heteroatom-containing ligands 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 alcohol, 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 amine compounds such as 5-chloro-8-quinolinol, 2,2'-bipyridyl and its derivatives, 2,2'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenol and its derivatives, and 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-tert-octylphenol]; quaternary ammonium salts such as trioctylmethylammonium chloride and trioctylmethylammonium acetate; phosphine compounds such as trimethylphosphine, tributylphosphine, and triphenylphosphine; phosphonium salts such as tetramethylphosphonium chloride, tetraethylphosphonium chloride, tetrapropylphosphonium chloride, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, trimethyl(2-hydroxypropyl)phosphonium chloride, triphenylphosphonium chloride, and benzylphosphonium chloride; and sulfur-based compounds such as thiolactic acid, 2-aminothiophenol, and 2,2'-dithiodianiline.

[0031] 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.

[0032] The heteroatom-containing ligand that forms the metal complex may be of one type alone or of two or more types that are different in structure from each other.

[0033] In the metal complex, the ratio (molar ratio) of the fatty acid metal salt to the heteroatom-containing ligand is, for example, in the range of 0.1 to 12 moles, preferably 0.3 to 10 moles, and more preferably 0.5 to 10 moles, of the heteroatom-containing ligand per mole of the metal atom of the fatty acid metal salt.

[0034] The metal complex of a fatty acid metal salt and a heteroatom-containing ligand can be produced by a known method, for example, by reacting a fatty acid metal salt with a heteroatom-containing ligand. Alternatively, a commercially available metal complex may be used.

[0035] [Coating composition] The coating composition of the present invention contains the anti-biofilm agent of the present invention and a binder resin. Since the anti-biofilm agent of the present invention has high compatibility with binder resins, the coating layer obtained from the coating composition containing the anti-biofilm agent of the present invention exhibits anti-biofilm properties while reducing the effects on the surface appearance of the coating layer, such as damage to the surface appearance due to precipitation of the anti-biofilm agent.

[0036] The content of the anti-biofilm 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 anti-biofilm agent may be contained in a range of 0.01 to 30 parts by mass per 100 parts by mass of resin solid content, preferably in a range of 0.01 to 20 parts by mass per 100 parts by mass of resin solid content, more preferably in a range of 0.05 to 10 parts by mass per 100 parts by mass of resin solid content, even more preferably in a range of 0.1 to 5 parts by mass per 100 parts by mass of resin solid content, and particularly preferably in a range of 0.1 to 3 parts by mass per 100 parts by mass of resin solid content. Here, the term "resin solid content" refers to the total amount of solid content such as binder resin other than the solvent contained in the coating composition.

[0037] The curing properties of the binder resin contained in the coating composition of the present invention are not particularly limited. For example, when the binder resin is an acrylic resin, the acrylic resin may be a thermosetting acrylic resin or an active energy ray-curable acrylic resin. The binder resin is not particularly limited in form, and may be an emulsion resin or a latex resin.

[0038] 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 resin at 20° C. is less than 10 ml. The term "water-insoluble resin" refers to a resin that is not one of the aforementioned "water-soluble resins."

[0039] 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 also includes modified versions of the above resins, and for example, in the case of phenolic resin, it also includes rosin-modified phenolic resin.

[0040] The binder resin contained in the coating composition of the present invention may be one type alone or two or more types.

[0041] 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 99.9 mass % of the total solid content of the coating composition.

[0042] The coating composition of the present invention only needs to contain the antibiofilm 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.

[0043] Specific examples of the dispersion medium include water, monofunctional alcohols such as 1-butanol, isobutanol, 1-pentanol, 2-methyl-2-pentanol, 3-methyl-3-pentanol, methyl ethyl ketone, methanol, ethanol, n-propyl alcohol, and isopropyl alcohol, various diols, polyhydric alcohols such as glycerin, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, and 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 adducts of bisphenol A with alkylene oxides having 2 or 3 carbon atoms (average number of added moles: 1 to 16); and hydrogenated bisphenol A. alicyclic diols such as 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.

[0044] The dispersion medium contained in the coating composition of the present invention may be one type alone or two or more types.

[0045] 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 falls within the range of 30 to 80% by mass, for example.

[0046] The coating composition of the present invention may further contain a plasticizer. Addition of a plasticizer to the coating composition can impart flexibility to the resulting coating layer and improve its ability to conform to the substrate.

[0047] 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, trimellitate esters, chlorinated paraffins, hydrocarbon oils, process oils, polyethers, epoxy plasticizers, and polyester plasticizers, 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.

[0048] The coating composition of the present invention may contain one type of plasticizer alone or two or more types of plasticizers.

[0049] 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.

[0050] The coating composition of the present invention may contain the anti-biofilm agent of the present invention, a binder resin, and optionally a dispersion medium and / or a plasticizer, and may also contain other additives to the extent that the effects of the present invention are not impaired. Examples of such other additives include pigments, matting agents, curing agents, curing accelerators, antifoaming agents, dispersants, leveling agents, thickeners, antioxidants, weathering agents, flame retardants, antistatic agents, lubricants, preservatives, and anti-biofilm agents other than the anti-biofilm agent of the present invention (e.g., isothiazolinone compounds, thiazolinone compounds, thiazole compounds, triazine compounds, urea compounds, imidazole compounds, benzimidazole compounds, pyridine compounds, zinc pyrithione compounds, and phenylphenol compounds).

[0051] The coating layer of the coating composition of the present invention may be a cured film obtained by curing the coating composition, or may be an uncured film of the coating composition. When the coating layer is a cured coating film of a coating composition, the coating composition of the present invention may be applied to the surface of a substrate, and the resulting coating film may be cured by a method suitable for the binder resin (thermal curing, active energy ray curing, etc.).

[0052] The coating composition can be applied by any known and commonly used coating method, such as a roll coater, electrostatic coating, bar coater, gravure coater, knife coater, dipping coating, or spray coating.

[0053] 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.

[0054] 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, etc. The resin substrate to be used may be subjected to a surface treatment such as a corona treatment.

[0055] [Resin composition] The resin composition of the present invention contains the anti-biofilm agent of the present invention and a resin. The resin composition containing the anti-biofilm agent of the present invention can be used not only for coating applications, but also for molding into a molded article that exhibits anti-biofilm properties.

[0056] The resin contained in the resin composition of the present invention can be the same as the binder resin contained in the coating composition of the present invention. Furthermore, the resin composition of the present invention can contain the same components as those that can be contained in the coating composition of the present invention.

[0057] 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.

[0058] The coating layer obtained using the coating composition of the present invention and the molded article obtained using the resin composition of the present invention can be used as a material with anti-biofilm properties and are suitable for use in humid areas where biofilms are likely to form.

[0059] Applications include bathroom components such as bathtubs, bathroom walls, and faucets; sanitary components such as sinks, basins, and toilet bowls; cooking components for kitchens and other areas; drainage components such as drain plugs, drain pipes, and drainage ditches; water storage and waterway equipment such as water tanks, reservoirs, pools, artificial ponds, and cooling circulating water channels; air conditioning equipment such as heat exchangers and drain pans; outdoor equipment such as signs, labels, and guardrails; and textile products such as clothing and towels. In addition to the above, it can also be applied to medical devices where biofilms are likely to form (e.g., endoscopes, catheters, and artificial dialysis machines).The anti-biofilm agent can also be used alone in body cleansers, toothpastes, oral care products, denture care products, contact lens cleaners, and other products. [Example]

[0060] The present invention will be specifically described below with reference to examples and comparative examples. The present invention is not limited to the following examples.

[0061] (Synthesis Example 1: Preparation of neodymium neodecanoate) 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. The neodymium content in the resulting neodymium neodecanoate was 8.8% by mass.

[0062] (Synthesis Example 2: Preparation of bismuth octoate) 330.6 parts by mass of octylic acid and 125.0 parts by mass of bismuth oxide were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 439.5 parts by mass of a bismuth octylate (bismuth 2-ethylhexanoate) solution was obtained. The bismuth content in the obtained bismuth octylate was 25% by mass.

[0063] (Example 1-2: Production of urethane resin coated substrate) Each coating composition was prepared by adding the anti-biofilm agent shown in Table 1 in the amount shown in Table 1 to a urethane resin (DIC Corporation's "Burnoc 16-416"). The prepared coating composition was applied to a 30 mm × 30 mm × 2 mm glass plate using an applicator to a wet film thickness of 152 μm, and the resulting coated substrate was dried overnight at room temperature and then further dried for 1 hour at 80 ° C to produce an anti-biofilm sample, which was a laminate of a urethane resin coating layer and a glass plate. Note that the urethane resin coating layers of Examples 1-2 were all clear and highly transparent. The following antibiofilm test was carried out using the prepared antibiofilm samples, and the results are shown in Table 1.

[0064] (Anti-biofilm test) The antibiofilm activity test was carried out in accordance with ISO 4768: 2023. Specifically, the following procedure was carried out to calculate the antibiofilm activity value R. The prepared antibiofilm sample and the unprocessed glass plate sample were placed in a sterilized container (sterilized at 80°C for 15 minutes using a dry heat sterilizer), and a test solution of Staphylococcus epidermidis (ATCC 35984) was added to the container. In this state, the container was heated to 35°C and cultured for 48 hours to allow biofilm formation on the two samples. After the incubation, the unfixed cells were washed off, and the biofilms formed on the samples were stained with crystal violet solution for 30 minutes. The stained biofilms were then wiped off with a water-soluble nonwoven fabric and collected. The water-soluble nonwoven fabric used to wipe off the biofilms was dissolved, and the absorbance of the resulting solutions was measured at 590 nm using a spectrophotometer. The absorbance of the biofilm formed on the anti-biofilm sample was calculated as W treated , the absorbance of the biofilm formed on the raw sample is W untreated The antibiofilm activity value R [%] was calculated using the following formula. R=(1-W treated / W untreated ) x 100

[0065] [Table 1]

[0066] Regarding the metal content in Table 1, the numbers indicate the percentage of metal content derived from fatty acid metal salts. For example, in Example 1, this means that the content of neodymium derived from neodymium neodecanoate was 0.88 mass % of the total resin solid content of the coating composition.

[0067] If the anti-biofilm activity value is positive, it is judged to have anti-biofilm properties, and if it does not have anti-biofilm properties, it is a negative value. The results in Table 1 show that the anti-biofilm agent of the present invention has high anti-biofilm properties.

[0068] (Example 3-4: Production of acrylic resin coated substrate) An acrylic resin ("Acrydic A-166" manufactured by DIC Corporation) was used instead of the urethane resin, and the anti-biofilm agent shown in Table 2 was added in the amount shown in Table 2 to prepare each coating composition. Using the prepared coating composition, anti-biofilm samples, which were laminates of an acrylic resin coating layer and a glass plate, were produced in the same manner as in Examples 1-2, and the anti-biofilm properties were evaluated. The results are shown in Table 2. Note that the acrylic resin coating layers of Examples 3-4 were all clear and highly transparent.

[0069] [Table 2]

[0070] Regarding the metal content in Table 2, the numbers indicate the percentage of metal content derived from fatty acid metal salts. For example, in Example 3, the content of bismuth derived from bismuth octoate was 0.31% by mass of the total resin solid content of the coating composition.

[0071] If the anti-biofilm activity value is positive, it is determined that the agent has anti-biofilm properties, and if it does not have anti-biofilm properties, it is a negative value. The results in Table 2 show that the anti-biofilm agent of the present invention has high anti-biofilm properties.

Claims

1. An anti-biofilm agent containing a fatty acid metal salt of a fatty acid having 1 to 22 carbon atoms and a metal, The anti-biofilm agent, wherein the metal is copper, bismuth, zinc, magnesium, cobalt, or a rare earth.

2. The anti-biofilm agent according to claim 1, wherein the fatty acid is 2-ethylhexanoic acid, neodecanoic acid, isononanoic acid, naphthenic acid, lauric acid, stearic acid, palmitic acid, isostearic acid, or oleic acid.

3. The anti-biofilm agent according to claim 1 , wherein the metal is bismuth or a rare earth.

4. An anti-biofilm coating composition comprising the anti-biofilm agent according to any one of claims 1 to 3 and a binder resin.

5. The anti-biofilm coating composition according to claim 4, wherein the binder resin is one or more 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.

6. The anti-biofilm coating composition according to claim 4, containing the metal derived from the anti-biofilm agent in a range of 0.01 to 30 parts by mass per 100 parts by mass of resin solids.

7. A laminate having a coating layer of the anti-biofilm coating composition according to claim 4 and a substrate.

8. An anti-biofilm resin composition comprising the anti-biofilm agent according to any one of claims 1 to 3 and a resin.

9. A molded article obtained by molding the anti-biofilm resin composition according to claim 8.

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