Anti-biofilm agent, Anti-biofilm resin composition, Anti-biofilm coating material, and Anti-biofilm product

Abstract

The present invention provides an anti-biofilm agent, an anti-biofilm resin composition, and an anti-biofilm coating material that have an excellent anti-biofilm effect of suppressing the formation of a biofilm. The anti-biofilm agent, the anti-biofilm resin composition, and the anti-biofilm coating material according to the present invention contains a compound represented by formula (1) such that: while the compound represented by formula (1) is stably present on the surface of a base material, the compound exhibits excellent interactions with microorganisms and suppresses the adhesion of the microorganisms to the surface of the base material; and even if a microorganism is adhered to the surface of the base material, the proliferation of the microorganism on the surface of the base material can be suppressed, and the generation of a biofilm on the surface of the base material can be suppressed.

Description

Anti-biofilm agent, anti-biofilm resin composition, anti-biofilm paint, and anti-biofilm product

[0001] The present invention relates to an anti-biofilm agent, an anti-biofilm resin composition, an anti-biofilm paint, and an anti-biofilm product.

[0002] Biofilms are membranes that surround microorganisms and are formed when microorganisms attached to a substance secrete extracellular polysaccharides (EPS). EPS acts as a barrier to protect the microorganisms, acts as a transport route for the microorganisms to take in nutrients, and protects the microorganisms inside the biofilm from environmental changes and chemical substances.

[0003] Biofilms form not only in natural environments such as ponds and rivers, but also inside plant pipes, causing problems such as the introduction of foreign matter into products when the biofilms peel off. Furthermore, when biofilms form on wet components used in bathrooms, kitchens, and other areas, they can cause slime and foul odors, resulting in hygiene problems. Furthermore, when biofilms form on the inner surfaces of aquariums, they can adversely affect the organisms in the aquarium. Therefore, there is a need for methods to inhibit biofilm formation.

[0004] Patent Document 1 discloses a biofilm formation inhibitor containing palmitoleic acid as an active ingredient.

[0005] Patent Document 2 discloses a biofilm dispersant containing, as an active ingredient, a compound represented by a specific structural formula or a salt thereof.

[0006] Patent Document 3 discloses a method for obtaining antimicrobial, antiseptic and / or antifouling properties within or on the surface of an article and / or material for protection, in which a compound having a specific structural formula, or an adduct or salt thereof, is applied to the article and / or material.

[0007] Japanese Patent Laid-Open No. 10-101502 Japanese Patent Laid-Open No. 2020-117451 Special Publication No. 2013-503122

[0008] However, the biofilm formation inhibitors disclosed in Patent Documents 1 to 3 and the like are insufficient in their inhibitory effect on biofilm formation, and there is a demand for agents that have excellent anti-biofilm effects.

[0009] The present invention provides an anti-biofilm agent, an anti-biofilm resin composition, an anti-biofilm paint, and an anti-biofilm product that have an excellent anti-biofilm effect of suppressing biofilm formation.

[0010] The anti-biofilm agent of the present invention is characterized by containing a compound represented by formula (1). However, R 1 ~R 4 are each independently a hydrogen atom or an arbitrary substituent, and R 1 ~R 4 At least one of the substituents is an alkyl group having 4 or more carbon atoms, and R 5 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group.

[0011] The anti-biofilm resin composition of the present invention is characterized by containing the anti-biofilm agent and a synthetic resin.

[0012] The anti-biofilm paint of the present invention is characterized by containing the above-mentioned anti-biofilm agent, a binder resin, and a solvent.

[0013] The anti-biofilm product of the present invention is characterized by comprising a substrate and the anti-biofilm agent according to claim 1 or claim 2.

[0014] The anti-biofilm agent, anti-biofilm resin composition, and anti-biofilm paint of the present invention (hereinafter collectively referred to as the "anti-biofilm group") contain the compound shown in formula (1). Therefore, the compound shown in formula (1) is present stably on the surface of the substrate, exhibits excellent interaction with microorganisms, and inhibits the adhesion of microorganisms to the surface of the substrate. Even if microorganisms do adhere to the surface of the substrate, the formation of a biofilm on the surface of the substrate can be inhibited (anti-biofilm effect).

[0015] The anti-biofilm group of the present invention is characterized by comprising a compound represented by formula (1). However, R 1 ~R 4 are each independently a hydrogen atom or an arbitrary substituent, and R 1 ~R 4 At least one of the substituents is an alkyl group having 4 or more carbon atoms, and R 5 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group.

[0016] In the anti-biofilm agent, the content of the compound shown in formula (1) is preferably 50% by mass or more, more preferably 60% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, more preferably 90% by mass or more, more preferably 95% by mass or more, and more preferably 99% by mass or more.

[0017] To achieve an anti-biofilm effect, not only antibacterial activity but also other performances are required, such as inhibiting bacterial adhesion to the substrate surface, inhibiting EPS secretion even when bacteria adhere, and ensuring that the active ingredient does not dissolve in water and remains stable on the substrate surface. Therefore, the antibiofilm effect of conventional antibacterial agents does not necessarily correlate with the antibiofilm effect of antibiofilm agents, and antibiofilm agents do not necessarily exhibit antibiofilm effects. On the other hand, the antibiofilm group of the present invention, when configured as described above, exhibits the above performance and exhibits excellent antibiofilm effects.

[0018] Furthermore, recent studies have revealed that bis(-3'-5')-cyclic dimeric guanosine monophosphate (c-di-GMP, cyclic-di-GMP), a signaling molecule ubiquitously present in microorganisms, plays an important role as an intracellular second messenger involved in biofilm formation. Although the mechanism by which this occurs has not been clearly elucidated, the anti-biofilm group of the present invention is thought to control the intracellular concentration of cyclic-di-GMP and suppress biofilm formation.

[0019] [Compound Represented by Formula (1)] The anti-biofilm group contains a compound represented by formula (1) as an active ingredient.

[0020]

[0021] However, R 1 ~R 4 are each independently a hydrogen atom or an arbitrary substituent, and R 1 ~R 4 At least one of the substituents is an alkyl group having 4 or more carbon atoms, and R 5 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group.

[0022] In addition, when the compound represented by formula (1) has a plurality of hydroxyl groups directly bonded to the benzene ring in the molecule, R 1 ~R 5 must satisfy the above conditions.

[0023] In the compound represented by formula (1), at least one of the carbons adjacent to the carbon to which the hydroxyl group (phenolic hydroxyl group, —OH) is bonded has a substituent R 5 As the phenolic hydroxyl group, a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group is bonded, which promotes the interaction between the phenolic hydroxyl group and microorganisms, and the anti-biofilm group exhibits excellent anti-biofilm effects.

[0024] In the compound represented by formula (1), R 5 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group, and is preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom, since this improves the anti-biofilm effect of the anti-biofilm group.

[0025] Furthermore, in the compound represented by formula (1), R 1 ~R 4 At least one of the groups is an alkyl group having 4 or more carbon atoms, and this highly hydrophobic substituent can interact favorably with the hydrophobic portion of the microorganism.

[0026] The compound represented by formula (1) is a compound having a substituent R 1 ~R 5By replacing the group with a hydrogen atom or a specific substituent, it is presumed that the interaction between the phenolic hydroxyl group and the microorganism is promoted, thereby controlling the intracellular c-di-GMP concentration of the microorganism, and the anti-biofilm group exhibits excellent anti-biofilm effects.

[0027] In the compound represented by formula (1), R 1 ~R 4 At least one of the groups is an alkyl group having 4 or more carbon atoms. The alkyl group having 4 or more carbon atoms is preferably an alkyl group having 4 to 20 carbon atoms, more preferably an alkyl group having 4 to 18 carbon atoms, more preferably an alkyl group having 4 to 16 carbon atoms, more preferably an alkyl group having 4 to 14 carbon atoms, more preferably an alkyl group having 4 to 12 carbon atoms, more preferably an alkyl group having 4 to 10 carbon atoms, more preferably an alkyl group having 4 to 8 carbon atoms, and more preferably an alkyl group having 4 to 6 carbon atoms. R 1 ~R 4 When at least one of the groups is an alkyl group having 4 or more carbon atoms, the water resistance of the anti-biofilm group is improved, the interaction between the compound represented by formula (1) and the hydrophobic portion of the microorganism is improved, and the anti-biofilm group exhibits an excellent anti-biofilm effect. 1 ~R 4 When two or more of the alkyl groups are alkyl groups having 4 or more carbon atoms, the two or more alkyl groups having 4 or more carbon atoms may be the same or different.

[0028] The alkyl group having 4 or more carbon atoms is not particularly limited, and examples thereof include a tert-butyl group, an n-butyl group, an isobutyl group, a sec-butyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a tert-pentyl group, an n-hexyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a tert-pentyl group, an isohexyl group, an n-hexyl group, a sec-hexyl group, a heptyl group and its isomers, an octyl group and its isomers, a nonyl group and its isomers, a decyl group and its isomers, an undecyl group and its isomers, a tridecyl group and its isomers, and a tetradecyl group and its isomers. The alkyl group having 4 or more carbon atoms preferably has a branched chain, and is preferably a tert-butyl group, an isobutyl group, a sec-butyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a tert-pentyl group [CH3CH2C(CH3)2-], a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a tert-pentyl group. A tert-butyl group, an isobutyl group, a sec-butyl group, or a tert-pentyl group is more preferred, and a tert-butyl group or a tert-pentyl group is more preferred. The term "branched chain" refers to a structure in which, in the main chain constituting the longest carbon chain, a hydrogen atom bonded to a carbon atom constituting the main chain is replaced with a carbon chain having one or more carbon atoms. When an alkyl group having 4 or more carbon atoms has a branched chain, in addition to interacting with the hydrophilic portion of microorganisms via the phenolic hydroxyl group, it also easily interacts with the hydrophobic portion of microorganisms, thereby imparting excellent anti-biofilm effects to anti-biofilm groups.

[0029] In the compound shown in formula (1), the anti-biofilm effect of the anti-biofilm group is improved, so R 1 and R 3 It is preferable that either one or both of the following are alkyl groups having 4 or more carbon atoms. Examples of such compounds include the following formulas (3) to (10), (18) and (19). In formulas (3) to (10), any or all of the tert-butyl groups may be substituted with the above-mentioned alkyl groups having 4 or more carbon atoms. In formula (5), R 4may be an ethyl group, an n-propyl group, or an isopropyl group. 3 may be an ethyl group, an n-propyl group, or an isopropyl group. In formula (18), it may be a compound in which one or both tert-pentyl groups are substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (19), it may be a compound in which the dodecyl group is substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (19), R 4 may be an ethyl group, an n-propyl group, or an isopropyl group.

[0030]

[0031]

[0032]

[0033] In the compound shown in formula (1), the anti-biofilm effect of the anti-biofilm group is improved, so R 1 is an alkyl group having 4 or more carbon atoms, and R 3 or R 4 is preferably an alkyl group having 4 or more carbon atoms. Examples of such compounds represented by formula (1) include compounds represented by the following formulas (3), (5), (6) and (18). In formulas (3), (5) and (6), one or both of the tert-butyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (5), R 4 may be an ethyl group, an n-propyl group, or an isopropyl group. In formula (18), one or both of the tert-pentyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms.

[0034]

[0035]

[0036] The compound of formula (1) improves the anti-biofilm effect of the anti-biofilm group, and therefore (A)R 1 ~R 4Two of the substituents are alkyl groups having 4 or more carbon atoms, or (B) R 1 ~R 4 Among these, it is preferred that one of the substituents is an alkyl group having 4 or more carbon atoms, and one of the substituents is a substituent containing an aromatic ring having an alkyl group having 4 or more carbon atoms.

[0037] The aromatic ring includes not only a monocyclic aromatic ring but also a fused aromatic ring formed by condensing monocyclic aromatic rings. Examples of the aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, a biphenyl, and a phenoxyphenyl, with a benzene ring being preferred. The aromatic ring has one or more hydrogen atoms abstracted from either the aromatic ring or the fused aromatic ring, and is bonded to other atoms by a covalent bond.

[0038] Examples of compounds represented by formula (1) that satisfy the above (A) include compounds represented by the following formulae (3), (5), (6), and (18). In formulae (3), (5), and (6), one or both of the tert-butyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (5), R 4 may be an ethyl group, an n-propyl group, or an isopropyl group. In formula (18), one or both of the tert-pentyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms.

[0039]

[0040]

[0041] The substituent containing an aromatic ring having an alkyl group having 4 or more carbon atoms is preferably a substituent represented by formula (2).

[0042]

[0043] However, R 6 ~R 8 are each independently a hydrogen atom or an arbitrary substituent, and R 6 ~R 8 At least one of the substituents is an alkyl group having 4 or more carbon atoms.1 ~R 4 Since these are the same as the alkyl groups (including preferred alkyl groups) exemplified in R 1 ~R 4 and R 6 ~R 8 The examples of alkyl groups having 4 or more carbon atoms (including preferred alkyl groups) are the same, but may be the same or different. 9 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group, and is preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom, as these improve the anti-biofilm effect of the anti-biofilm group. Z is a sulfur atom, an oxygen atom, or a direct bond. Z is preferably a sulfur atom, as this improves the anti-biofilm effect of the anti-biofilm group. * is a bond and means a single bond.

[0044] R in the substituent shown in formula (2) 6 ~R 8 With regard to the substituents, it is preferable that the substituents other than the alkyl group having 4 or more carbon atoms are each independently a hydrogen atom, a hydroxyl group (-OH), or an alkyl group, since this improves the anti-biofilm effect of the anti-biofilm group. The number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1, since this imparts excellent water resistance to the anti-biofilm group and generates excellent interaction between the hydroxyl group (phenolic hydroxyl group, -OH) of the compound represented by formula (2) and microorganisms, thereby allowing the anti-biofilm group to exhibit excellent anti-biofilm effect.

[0045] In the compound represented by formula (2), R 6 is preferably an alkyl group having 4 or more carbon atoms, and R 6 is an alkyl group having 4 or more carbon atoms, and R 8 is preferably a hydroxyl group or an alkyl group. The anti-biofilm group exhibits excellent anti-biofilm effects. The number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1.

[0046] Examples of the compound represented by formula (1) that satisfies the above (B) include the compound represented by formula (4). In formula (4), one or both of the tert-butyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (4), R 4 and R 7 Each methyl group in may independently be an ethyl group, an n-propyl group, or an isopropyl group.

[0047]

[0048] R of the compound represented by formula (1) 1 ~R 4 In the substituents, it is preferable that the substituents other than the alkyl group having 4 or more carbon atoms are each independently a hydrogen atom, a hydroxyl group (—OH), or an alkyl group, since this improves the anti-biofilm effect of the anti-biofilm group. The number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 5 or less, more preferably 4 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1, since this imparts excellent water resistance to the anti-biofilm group while generating excellent interaction between the hydroxyl group of the compound represented by formula (1) and microorganisms, thereby allowing the anti-biofilm agent to exhibit excellent anti-biofilm effect. Examples of such compounds include compounds represented by formulas (3) to (10), (18), and (19). In formulas (3) to (10), any tert-butyl group may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (18), one or both tert-pentyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (19), the compound may be one in which the dodecyl group is substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formulas (3) to (10) and (19), the alkyl group other than the alkyl group having 4 or more carbon atoms may be an alkyl group having 3 or less carbon atoms (the number of carbon atoms in the alkyl group is more preferably 3 or less, more preferably 2 or 1, and still more preferably 1).

[0049] In the compound represented by formula (1), (C) R 1is an alkyl group having 4 or more carbon atoms, and R 3 is a hydroxyl group or an alkyl group having 3 or less carbon atoms, and R 2 and R 4 are each independently a hydrogen atom, a hydroxyl group, or an alkyl group (the number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 5 or less, more preferably 4 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1), or (D) R 1 is an alkyl group having 4 or more carbon atoms, and R 4 is a hydroxyl group or an alkyl group, and R 2 and R 3 are each independently a hydrogen atom, a hydroxyl group, or an alkyl group (the number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 5 or less, more preferably 4 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1), or (E)R 1 is an alkyl group having 4 or more carbon atoms, and R 3 is a hydroxyl group or an alkyl group having 3 or less carbon atoms, and R 2 is a hydrogen atom, and R 4 is preferably a hydrogen atom or an alkyl group having 4 or more carbon atoms. When the compound represented by formula (1) satisfies the above (C), (D), or (E), the anti-biofilm group exhibits an excellent anti-biofilm effect. In the above (C), R of the compound represented by formula (1) 3 In the above (D), the number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 5 or less, more preferably 4 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1. 4In the formula (6), the number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 8 or less, more preferably 6 or less, more preferably 5 or less, more preferably 4 or less, more preferably 3 or less, more preferably 2 or 1, and more preferably 1. As such compounds, for example, formulas (6), (8), (9) and (18) are preferred. In formulas (6), (8) and (9), any tert-butyl group may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formulas (6), (8) and (9), R 3 may be an alkyl group having 10 or less carbon atoms (excluding methyl group), or may be an ethyl group, an n-propyl group, or an isopropyl group. In formula (18), one or both tert-pentyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms. In formula (18), R 3 may be an alkyl group having 10 or less carbon atoms (excluding methyl), or may be an ethyl group, an n-propyl group, or an isopropyl group.

[0050]

[0051]

[0052] The compound of formula (1) improves the anti-biofilm effect of the anti-biofilm group, so R 1 is an alkyl group having 4 or more carbon atoms, and R 2 ~R 4 At least one (preferably one) of the substituents is an alkyl group having 4 or more carbon atoms, and R 2 ~R 4 Among R, it is preferred that the substituents other than the alkyl group having 4 or more carbon atoms are each independently a hydrogen atom, a hydroxyl group, or an alkyl group (the number of carbon atoms in the alkyl group is more preferably 3 or less, more preferably 2 or 1, and still more preferably 1), and R 1 is an alkyl group having 4 or more carbon atoms, and R 3 or R 4 is an alkyl group having 4 or more carbon atoms, and R 2 ~R 4It is more preferable that the substituents other than the alkyl group having 4 or more carbon atoms are each independently a hydrogen atom, a hydroxyl group, or an alkyl group (the number of carbon atoms in the alkyl group is more preferably 3 or less, more preferably 2 or 1, and even more preferably 1). As such a compound represented by formula (1), for example, compounds represented by the following formulas (3), (5), (6), and (18) are preferable. In addition, in formulas (3), (5), and (6), compounds in which one or both tert-butyl groups are substituted with the above-mentioned alkyl group having 4 or more carbon atoms may also be used. In formula (5), R 4 may be an ethyl group, an n-propyl group, or an isopropyl group. In formula (18), one or both of the tert-pentyl groups may be substituted with the above-mentioned alkyl group having 4 or more carbon atoms.

[0053]

[0054]

[0055] The constituent atoms constituting the compound represented by formula (1) preferably do not contain atoms other than carbon, oxygen, hydrogen, nitrogen, and sulfur atoms. The compound represented by formula (1) is preferably composed of only three or more atoms selected from the group consisting of carbon, oxygen, hydrogen, nitrogen, and sulfur atoms, and more preferably composed of only carbon, oxygen, and hydrogen atoms, or only carbon, oxygen, hydrogen, nitrogen, and sulfur atoms. When the compound represented by formula (1) is composed of the above constituent atoms, the anti-biofilm group exhibits an excellent anti-biofilm effect. The compound represented by formula (1) preferably does not contain a halogen atom, since the anti-biofilm group exhibits an excellent anti-biofilm effect.

[0056] The solubility of the compound represented by formula (1) in water at 25°C is preferably 0.08 g / 100 mL or less, more preferably 0.07 g / 100 mL or less, more preferably 0.06 g / 100 mL or less, more preferably 0.05 g / 100 mL or less, more preferably 0.04 g / 100 mL or less, more preferably 0.03 g / 100 mL or less, and more preferably 0.02 g / 100 mL or less. When the solubility of the compound represented by formula (1) in water at 25°C is 0.08 g / 100 mL or less, the anti-biofilm effect of the anti-biofilm group is improved.

[0057] The solubility (g / 100 mL) of the compound represented by formula (1) in water at 25°C refers to the mass (g) of the compound represented by formula (1) that can be dissolved in 100 mL of water, and refers to the mass (g) of the compound represented by formula (1) dissolved in 100 mL of water in a saturated aqueous solution at 25°C. Specifically, the solubility of the compound represented by formula (1) in water at 25°C refers to a value measured at 25°C in accordance with OECD Chemicals Testing Guideline No. 105 (Water Solubility).

[0058] The molecular weight of the compound represented by formula (1) is preferably 150 or more, more preferably 160 or more, more preferably 170 or more, more preferably 180 or more, more preferably 190 or more, more preferably 200 or more, and more preferably 205 or more. The molecular weight of the compound represented by formula (1) is preferably 500 or less, more preferably 450 or less, more preferably 430 or less, more preferably 410 or less, more preferably 400 or less, more preferably 390 or less, more preferably 380 or less, and more preferably 370 or less. When the molecular weight of the compound represented by formula (1) is within the above range, the anti-biofilm group exhibits excellent anti-biofilm effect.

[0059] [Anti-biofilm agent] The anti-biofilm agent contains a compound represented by formula (1) as an active ingredient. The anti-biofilm agent may contain additives (e.g., pigments, plasticizers, hardeners, extenders, fillers, antioxidants, thickeners, surfactants, etc.) as needed. The anti-biofilm agent has an anti-biofilm effect against various microorganisms due to the action of the compound represented by formula (1).

[0060] Here, the anti-biofilm effect refers to the effect of suppressing the adhesion of microorganisms to the surface of a substrate and, even if microorganisms do adhere to the surface of the substrate, suppressing the formation of a biofilm on the surface of the substrate. The anti-biofilm agent may have an anti-biofilm activity value of 55 or higher against any microorganism.

[0061] The anti-biofilm activity value can be measured, for example, as follows: 5 parts by mass of the anti-biofilm agent and 95 parts by mass of polypropylene are melt-kneaded and mixed at 220°C for 10 minutes to prepare an anti-biofilm resin composition.

[0062] The obtained anti-biofilm resin composition is press-molded to obtain a sheet-shaped synthetic resin molded product having an average thickness of 1 mm as an anti-biofilm product, while the polypropylene alone is press-molded to obtain a sheet-shaped synthetic resin molded product having an average thickness of 1 mm as an unprocessed product.

[0063] The antibiofilm activity value of the obtained antibiofilm product and the unprocessed product is measured in accordance with ISO 4768, for example, as follows.

[0064] The antibiofilm product, which was a flat square with a side of 3 cm and attached to a flat square glass plate with a side of 4 cm, was placed in a sterilized container, and then 2 x 10 3 A test bacterial solution of Staphylococcus epidermidis (ATCC 35984) adjusted to CFU / mL was added and cultured at 35°C for 48 hours to form a biofilm. After culture, the anti-biofilm product attached to the glass plate was stained with a crystal violet solution, the surface was washed with purified water, and the stained biofilm was wiped off with a water-soluble nonwoven fabric.

[0065] The obtained water-soluble nonwoven fabric is added to 5 mL of a 1% aqueous solution of sodium dodecyl sulfate and dissolved by shaking to obtain a solution. The absorbance (Wtreated) at 590 nm of the obtained solution is measured using a microplate reader. The same procedure as above is also carried out on an untreated product having a flat square shape with sides of 3 cm attached to a 4 cm square glass plate with sides of 4 cm, and the absorbance (Wuntreated) at 590 nm is measured, and the antibiofilm activity value is then calculated using the following formula: Antibiofilm activity value (%) = (1 - Wtreated / Wuntreated) x 100

[0066] The antibiofilm activity value of the antibiofilm agent is preferably 55 or more, more preferably 58 or more, more preferably 59 or more, more preferably 60 or more, more preferably 65 or more, more preferably 70 or more, more preferably 75 or more, and more preferably 78 or more.

[0067] The microorganism is not particularly limited as long as it is a microorganism that forms a biofilm, and may be a prokaryote such as a bacterium, or a eukaryote such as a yeast or a mold. The bacterium may be either a gram-positive bacterium or a gram-negative bacterium.

[0068] Examples of Gram-positive bacteria include bacteria of the genus Bacillus (e.g., Bacillus coagulans, Bacillus anthracis, Bacillus atrophaeus, Bacillus cereus, Bacillus megaterium, Bacillus pumilus, Bacillus subtilis, etc.), bacteria of the genus Clostridium (e.g., Clostridium botulinum, Clostridium difficile, Clostridium perfringens, Clostridium sporogenes, Clostridium tetani, etc.), bacteria of the genus Enterococcus (e.g., Enterococcus faecalis, Enterococcus faecium, etc.), and bacteria of the genus Lactobacillus (e.g., Lactobacillus brevis, Lactobacillus fructivorans, Lactobacillus plantarum, etc.), Mycobacterium bacteria (e.g., Mycobacterium bovis, Mycobacterium leprae, Mycobacterium terrae, Mycobacterium tuberculosis, etc.), Propionibacterium bacteria (e.g., Propionibacterium acnes, etc.), Staphylococcus bacteria (e.g., Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus lugdunensis, Staphylococcus saprophyticus, etc.), Streptococcus bacteria (e.g., Streptococcus mitis, Streptococcus Streptococcus mutansoralis, Streptococcus pneumoniae, Streptococcus pyogenes, etc.

[0069] Examples of Gram-negative bacteria include Bordetella bacteria (e.g., Bordetella pertussis), Campylobacter bacteria (e.g., Campylobacter jejuni), Enterobacter bacteria (e.g., Enterobacter cloacae), Escherichia bacteria (e.g., Escherichia coli), Fusobacterium bacteria (e.g., Fusobacterium nucleatum), Helicobacter bacteria (e.g., Helicobacter pylori), Klebsiella bacteria (e.g., Klebsiella pneumoniae), and Neisseria bacteria (e.g., Neisseria gonorrhoeae). meningitidis, etc.), Pseudomonas bacteria (e.g., Pseudomonas aeruginosa, Pseudomonas putida, etc.), Salmonella bacteria (e.g., Salmonella enterica serovar Typhi, Salmonella enterica serovar Paratyphi A, Salmonella enterica serovar Typhimurium, Salmonella enterica serovar Enteritidis, etc.), Serratia bacteria (e.g., Serratia marcescens, etc.), Vibrio bacteria (e.g., Vibrio cholerae, Vibrio parahaemolyticus, etc.), etc.

[0070] The anti-biofilm agent may be used by adhering (supporting) it to the surface of base particles. By adhering the anti-biofilm agent to the surface of the base particles, the anti-biofilm agent can be more uniformly dispersed in the substrate. Furthermore, the surface area of ​​the anti-biofilm agent can be increased. Therefore, sufficient contact between the anti-biofilm agent and microorganisms can be ensured, allowing the anti-biofilm effect of the anti-biofilm agent to be fully exerted.

[0071] The base particles to which the anti-biofilm agent adheres are not particularly limited as long as they do not inhibit the anti-biofilm effect of the anti-biofilm agent. The base particles may be either resin particles or inorganic particles. The base particles may be used alone or in combination of two or more types.

[0072] Examples of synthetic resins constituting the resin particles include styrene-based resins, acrylic-based resins, urethane-based resins, vinyl chloride-based resins, ABS resins, and synthetic rubbers such as styrene-butadiene rubber (SBR) and nitrile-butadiene rubber (NBR), with styrene-based resins and acrylic resins being preferred. In the present invention, "synthetic resin" refers to a compound having a molecular main chain mainly composed of covalent bonds and a molecular weight of 10,000 or more.

[0073] The styrene-based resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, styrene-based monomers such as styrene, methylstyrene, ethylstyrene, i-propylstyrene, dimethylstyrene, chlorostyrene, and bromostyrene, and copolymers containing, as monomer units, a styrene-based monomer and one or more vinyl monomers copolymerizable with the styrene-based monomer.

[0074] Examples of vinyl monomers copolymerizable with styrene-based monomers include acrylic monomers such as acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, acrylic acid esters (methyl acrylate, ethyl acrylate, butyl acrylate, etc.), methacrylic acid esters (methyl methacrylate, ethyl methacrylate, butyl methacrylate, etc.), maleic anhydride, and acrylamide.

[0075] The acrylic resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, acrylic monomers such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and pentyl (meth)acrylate, and copolymers containing, as monomer units, an acrylic monomer and one or more vinyl monomers copolymerizable with the acrylic monomer. Note that (meth)acrylate means acrylate or methacrylate.

[0076] Examples of vinyl monomers copolymerizable with acrylic monomers include acrylonitrile, methacrylonitrile, maleic anhydride, and acrylamide.

[0077] The inorganic material constituting the inorganic particles is not particularly limited, and examples thereof include zeolite, hydrotalcite, calcium carbonate, calcium citrate, magnesium carbonate, and magnesium hydroxide.

[0078] The synthetic resin constituting the resin particles preferably contains an aromatic ring skeleton, which attracts the hydrophobic moiety of the compound represented by formula (1) attached to the surface of the resin particles and orients the hydroxyl groups (phenolic hydroxyl groups) of the compound represented by formula (1) outward, thereby enabling the anti-biofilm agent to more effectively exert its anti-biofilm effect.

[0079] The aromatic ring skeleton may be a monocyclic aromatic ring or may be a fused monocyclic aromatic ring (fused aromatic ring). The aromatic ring is not particularly limited, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, biphenyl, and phenoxyphenyl. The aromatic ring is formed by removing (pulling out) one or more hydrogen atoms from either the aromatic ring or the fused aromatic ring, and is bonded to other atoms via a covalent bond.

[0080] The amount of the anti-biofilm agent attached to the base particles is preferably 1 part by mass or more, more preferably 5 parts by mass or more, more preferably 7 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the base particles. When the amount of the anti-biofilm agent attached is 1 part by mass or more, the anti-biofilm agent can be uniformly attached to the surface of the base particles, and the anti-biofilm effect of the anti-biofilm agent can be more effectively exerted.

[0081] The amount of the anti-biofilm agent attached to the base particles is preferably 1000 parts by mass or less, more preferably 800 parts by mass or less, more preferably 600 parts by mass or less, and even more preferably 400 parts by mass or less, per 100 parts by mass of the base particles. When the amount of the anti-biofilm agent attached is 1000 parts by mass or less, the anti-biofilm agents do not bond to each other, and the anti-biofilm agent is efficiently arranged on the surface of the base particles, improving the anti-biofilm effect.

[0082] The method for attaching the anti-biofilm agent to the surface of the base particle is not particularly limited, and may be, for example, by the adhesive strength of the anti-biofilm agent, or by using a binder resin to adhere the anti-biofilm agent to the surface of the base particle. However, since this allows the anti-biofilm effect of the anti-biofilm agent to be effectively exerted, it is preferable that the anti-biofilm agent be attached to the surface of the base particle by the adhesive strength of the anti-biofilm agent itself.

[0083] The anti-biofilm agent is used by being contained in a substrate to which an anti-biofilm effect is to be imparted, and the substrate containing the anti-biofilm agent exhibits an anti-biofilm effect as an anti-biofilm product.

[0084] The substrate for containing the anti-biofilm agent is not particularly limited as long as it is capable of containing the anti-biofilm agent, and examples include water supply and drainage pipes, kitchen utensils and kitchen components, washroom utensils and washroom components, bathroom utensils and bathroom components, toilet utensils and toilet components, cleaning supplies and components for cleaning equipment, cooking utensils and components for cooking equipment, water storage supplies and components for water storage equipment, humidifiers and components for humidifier equipment, air conditioning supplies and components for air conditioning equipment, water treatment supplies and components for water treatment equipment, agricultural supplies and components for agricultural equipment, fishing supplies and components for fishing equipment, components for manufacturing equipment, components for river and port facilities, components for water utilization equipment, and components for civil engineering facilities.

[0085] Methods for incorporating an anti-biofilm agent into the substrate include a method of mixing the anti-biofilm agent into a molded body that constitutes the substrate, and a method of applying a paint or the like containing the anti-biofilm agent to the surface of the substrate, thereby coating the surface of the substrate with a coating film containing the anti-biofilm agent.

[0086] [Anti-biofilm resin composition] The anti-biofilm resin composition contains the compound represented by the above formula (1) and a synthetic resin. The anti-biofilm resin composition can be obtained by mixing the compound represented by the above formula (1) and the synthetic resin in a known manner.

[0087] The anti-biofilm resin composition can be used in a general-purpose synthetic resin molding method to obtain an anti-biofilm product containing a substrate containing a synthetic resin and an anti-biofilm agent containing the compound shown in formula (1) contained in the substrate. Examples of general-purpose synthetic resin molding methods include extrusion molding, injection molding, and blow molding. The anti-biofilm resin composition containing a synthetic resin and an anti-biofilm agent containing the compound shown in formula (1) can be used as a synthetic resin molding masterbatch, and the synthetic resin molding masterbatch can be mixed with a synthetic resin as a raw material to produce an anti-biofilm product using a general-purpose synthetic resin molding method.

[0088] The synthetic resin constituting the substrate is not particularly limited, and examples thereof include thermoplastic resins (e.g., polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyvinyl acetate, polyurethane, Teflon (registered trademark), acrylonitrile butadiene styrene resin, acrylonitrile styrene resin, acrylic resin, polyvinyl alcohol, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyester, polyethylene terephthalate, polybutylene terephthalate, cyclic polyolefin, polyphenylene sulfide, polytetrafluoroethylene, polysulfone, polyethersulfone, polyarylate, polyether ether ketone, thermoplastic polyimide, polyamide imide, etc.), and thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea resin, unsaturated polyester resin, alkyd resin, silicone resin, polyurethane, thermosetting polyimide, etc.). The synthetic resins may be used alone or in combination of two or more.

[0089] The content of the compound represented by the formula (1) in the anti-biofilm resin composition (except when used as a synthetic resin molding masterbatch) is more preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, more preferably 1 part by mass or more, and more preferably 2 parts by mass or more, relative to 100 parts by mass of the synthetic resin. The content of the compound represented by the formula (1) in the anti-biofilm resin composition is more preferably 90 parts by mass or less, more preferably 80 parts by mass or less, more preferably 20 parts by mass or less, and more preferably 10 parts by mass or less, relative to 100 parts by mass of the synthetic resin. When the content of the compound represented by the formula (1) in the anti-biofilm resin composition is 0.1 parts by mass or more, the anti-biofilm effect of the anti-biofilm resin composition can be improved. When the content of the compound represented by the formula (1) in the anti-biofilm resin composition is 90 parts by mass or less, the compound represented by the formula (1) is more likely to be uniformly dispersed without agglomeration without affecting the physical properties of the synthetic resin, thereby improving the anti-biofilm effect.

[0090] The anti-biofilm resin composition can be used as a masterbatch for synthetic resin molding. The synthetic resin used in the masterbatch for synthetic resin molding can be any of the synthetic resins exemplified as the synthetic resin constituting the substrate. Only one type of synthetic resin may be used, or two or more types may be used in combination.

[0091] The content of the compound represented by the formula (1) in the synthetic resin molding masterbatch is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and more preferably 20 parts by mass or more, relative to 100 parts by mass of the synthetic resin. The content of the compound represented by the formula (1) in the synthetic resin molding masterbatch is preferably 900 parts by mass or less, more preferably 800 parts by mass or less, more preferably 600 parts by mass or less, more preferably 400 parts by mass or less, more preferably 200 parts by mass or less, and more preferably 100 parts by mass or less, relative to 100 parts by mass of the synthetic resin.

[0092] The anti-biofilm resin composition, particularly the synthetic resin molding masterbatch, may contain an antioxidant. The antioxidant is not particularly limited, and examples thereof include phosphorus-based antioxidants, phenol-based antioxidants, and thioether-based antioxidants. When the anti-biofilm resin composition further contains an antioxidant, the heat resistance of the resulting anti-biofilm resin composition and anti-biofilm product is further improved, and an anti-biofilm product with excellent appearance can be obtained over a long period of time.

[0093] The content of the antioxidant in the anti-biofilm resin composition (except when used as a masterbatch for synthetic resin molding) is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, more preferably 0.03 parts by mass or more, and more preferably 0.05 parts by mass or more, per 100 parts by mass of synthetic resin. The content of the antioxidant in the anti-biofilm resin composition (except when used as a masterbatch for synthetic resin molding) is preferably 0.5 parts by mass or less, more preferably 0.4 parts by mass or less, and more preferably 0.3 parts by mass or less, per 100 parts by mass of synthetic resin.

[0094] The content of the antioxidant in the synthetic resin molding masterbatch is preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, and even more preferably 0.8 parts by mass or more, per 100 parts by mass of the synthetic resin. The content of the antioxidant in the synthetic resin molding masterbatch is preferably 4 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 2 parts by mass or less, per 100 parts by mass of the synthetic resin.

[0095] The synthetic resin molding masterbatch is preferably in the form of resin pellets because of its excellent moldability. By melting and molding the resin pellets, an anti-biofilm product (synthetic resin molded product) with excellent anti-biofilm effects can be obtained.

[0096] The shape of the resin pellets is not particularly limited, and examples thereof include spherical, cylindrical, and prismatic shapes. From the viewpoint of pellet shape stability, a cylindrical shape is preferred. The maximum length dimension of the resin pellets is preferably 1 mm or more, more preferably 3 mm or more. The maximum length dimension of the resin pellets is preferably 10 mm or less, more preferably 7 mm or less.

[0097] The synthetic resin molding masterbatch can be used by mixing with other resin materials. The other resin materials may be resin pellets. The synthetic resin molding masterbatch and the other resin materials are mixed to obtain a mixed resin material, and then the mixed resin material is molded to obtain an anti-biofilm product (synthetic resin molded article) with excellent anti-biofilm effects.

[0098] [Anti-biofilm paint] The anti-biofilm paint contains an anti-biofilm agent containing the compound shown in formula (1) above and a paint. The anti-biofilm paint can be obtained by mixing the anti-biofilm agent containing the compound shown in formula (1) above with a paint in a known manner. The anti-biofilm paint can be obtained by mixing the anti-biofilm agent with a paint. The coating film formed from the anti-biofilm paint exhibits excellent anti-biofilm effects.

[0099] As the paint, conventionally known paints can be used. Any of hydrophobic paints, hydrophilic paints, and water-based paints can be used. Hydrophobic paints are not particularly limited, and examples thereof include oil-based paints (e.g., blended paints, oil varnishes, etc.), cellulose paints, and synthetic resin paints. Paints also include photocurable paints that polymerize upon irradiation with radiation such as ultraviolet light to produce a binder. Hydrophilic paints are not particularly limited, and examples thereof include aqueous urethane paints, aqueous silicone paints, aqueous fluorine paints, and aqueous inorganic paints. Water-based paints contain an aqueous solvent and a binder, as described below.

[0100] The paint contains a binder, and the binder is not particularly limited as long as it can adhere the anti-biofilm agent to the surface of the substrate. Examples of binders include synthetic resin binders such as urethane resins such as one-component urethane resins and two-component urethane resins, silicone resins, acrylic resins, urethane acrylate resins, polyester resins, unsaturated polyester resins, alkyd resins, vinyl acetate resins, vinyl chloride resins, epoxy resins, and epoxy acrylate resins, with vinyl chloride resins being preferred.

[0101] The paint may contain additives such as pigments, plasticizers, curing agents, extenders, fillers, antioxidants, and thickeners, as long as the additives do not impair the paint's physical properties. Examples of methods for incorporating the anti-biofilm agent into paint include supplying the anti-biofilm agent, the paint, and additives added as needed to a dispersing device and uniformly mixing them. Examples of dispersing devices include a high-speed mill, a ball mill, and a sand mill.

[0102] The paint contains a solvent such as an aqueous solvent or an organic solvent to adjust the viscosity. The aqueous solvent is not particularly limited, and examples thereof include water, lower alcohols (e.g., alcohols having 1 to 5 carbon atoms such as methanol, ethanol, propanol, and butanol), and mixtures of water and lower alcohols. The organic solvent is not particularly limited, and examples thereof include alcohols excluding lower alcohols, toluene, xylene, methyl ethyl ketone, acetone, ethyl acetate, benzene, and isopropyl alcohol. The solvents may be used alone or in combination.

[0103] The content of the compound represented by formula (1) in the anti-biofilm paint is preferably 0.1% by mass or more, more preferably 1% by mass or more, and more preferably 2% by mass or more. The content of the compound represented by formula (1) in the anti-biofilm paint is preferably 10% by mass or less, more preferably 7% by mass or less, and more preferably 5% by mass or less. When the content of the compound represented by formula (1) is 0.1% by mass or more, the coating film formed from the anti-biofilm paint exhibits excellent anti-biofilm effect. When the content of the compound represented by formula (1) is 10% by mass or less, the coatability of the anti-biofilm paint and the appearance of the resulting coating film are improved.

[0104] The present invention will be described in more detail below using examples, but the present invention is not limited thereto. Specific numerical values ​​of the blending ratios (content ratios), physical property values, parameters, etc. used in the following description can be replaced with the upper limit values ​​(numeric values ​​defined as "equal to or less than") or lower limit values ​​(numeric values ​​defined as "equal to or greater than") of the corresponding blending ratios (content ratios), physical property values, parameters, etc. described in the "Summary of the Invention."

[0105] The compounds used in the production of the anti-biofilm agents of the Examples and Comparative Examples are shown below. [Compounds shown in formula (1)] 2,4-di-t-butylphenol [formula (3)] 4,4'-thiobis(6-tert-butyl-m-cresol) [formula (4)] 4,6-di-tert-butyl-m-cresol [formula (5)] 2,5-di-tert-butylhydroquinone [formula (6)] 2-amino-4-t-butylphenol [formula (7)] 2-tert-butyl-p-cresol [formula (8)] 6-tert-butyl-2,4-xylenol [formula (9)] 2-t-butylphenol [formula (10)] 2,5-di-tert-pentylhydroquinone [formula (18)] 2-dodecyl-p-cresol [formula (19)]

[0106]

[0107]

[0108]

[0109] [Other compounds] Methylenedisalicylic acid [Formula (11)] 2-Isopropyl-5-methylphenol [Formula (12)] 2,6-di-tert-butyl-p-cresol [Formula (13)] N,N'-bis{2-[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]ethyl}oxamide [Formula (14)] Pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) [Formula (15)] N,N'-bis-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionylhexamethylenediamine [Formula (16)] 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione [formula (17)]

[0110]

[0111] The solubility in water at 25°C and molecular weight of the compound represented by formula (1) above and other compounds are shown in Table 1. In Table 1, "solubility in water at 25°C" is expressed as "water solubility." In Table 1, "<X" (X is a number) means that the value is smaller than X.

[0112] Examples 1 to 10 and Comparative Examples 1 to 7 Antibiofilm agents containing 100% by mass of the compound represented by formula (1) shown in Table 1 or other compounds as the active ingredient were prepared.

[0113] An anti-biofilm resin composition was prepared by melt-kneading 5 parts by mass of the anti-biofilm agent and 95 parts by mass of polypropylene (trade name "Novalock PP BC6C" manufactured by Japan Polypropylene Corporation) at 220°C for 10 minutes.

[0114] The obtained anti-biofilm resin composition was press-molded to obtain a sheet-shaped synthetic resin molded body having an average thickness of 1 mm as an anti-biofilm product.

[0115] The polypropylene alone was press-molded to obtain a sheet-like synthetic resin molded product having an average thickness of 1 mm as an unprocessed product.

[0116] The antibiofilm activity values ​​of the obtained antibiofilm product and the untreated product were measured in accordance with ISO 4768 as follows, and the results are shown in Table 1.

[0117] (Anti-biofilm activity value) A flat square anti-biofilm product with a side of 3 cm attached to a flat square glass plate with a side of 4 cm was placed in a sterilized container, and then 2 × 10 3A test bacterial solution of Staphylococcus epidermidis (Staphylococcus epidermidis ATCC35984) adjusted to CFU / mL was added and cultured at 35 ° C for 48 hours to form a biofilm. After culture, the anti-biofilm product attached to the glass plate was stained with a crystal violet solution, the surface was washed with purified water, and the stained biofilm was wiped off with a water-soluble nonwoven fabric. The resulting water-soluble nonwoven fabric was added to 5 mL of a 1% aqueous solution of sodium dodecyl sulfate and dissolved by shaking to obtain a solution. The absorbance (W treated) at 590 nm of the resulting solution was measured using a microplate reader. The same procedure as above was also performed on an untreated product with a flat square shape and 3 cm sides attached to a 4 cm square glass plate. The absorbance (W untreated) at 590 nm was measured, and the anti-biofilm activity value was calculated using the following formula. Antibiofilm activity value (%) = (1 - Wtreated / Wuntreated) x 100

[0118]

[0119] (Cross-reference to related applications) This application claims priority to Japanese Patent Application No. 2024-128482, filed on August 2, 2024, the disclosure of which is incorporated herein by reference in its entirety.

[0120] The anti-biofilm agent, anti-biofilm resin composition and anti-biofilm paint of the present invention are stable on the surface of a substrate, exhibit excellent interaction with microorganisms, and inhibit the adhesion of microorganisms to the surface of the substrate. Even if microorganisms do adhere to the surface of the substrate, they can inhibit the proliferation of microorganisms on the surface of the substrate and inhibit the formation of a biofilm on the surface of the substrate.

Claims

1. An anti-biofilm agent comprising a compound represented by formula (1). However, R 1 ~R 4 are each independently a hydrogen atom or an arbitrary substituent, and R 1 ~R 4 At least one of the substituents is an alkyl group having 4 or more carbon atoms, and R 5 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group.

2. In the above formula (1), R 1 and R 3 The anti-biofilm agent according to claim 1, characterized in that either one or both of the above is an alkyl group having 4 or more carbon atoms.

3. R ​​in the above formula (1) 1 ~R 4 The anti-biofilm agent according to claim 1 or 2, characterized in that the substituents other than the alkyl group having 4 or more carbon atoms are each independently a hydrogen atom, a hydroxyl group, or an alkyl group.

4. R in the above formula (1) 1 ~R 4 The anti-biofilm agent according to claim 1 or 2, characterized in that one of the substituents is an alkyl group having 4 or more carbon atoms, and one of the substituents is a substituent containing an aromatic ring having an alkyl group having 4 or more carbon atoms.

5. The anti-biofilm agent according to claim 4, characterized in that the substituent containing an aromatic ring having an alkyl group with 4 or more carbon atoms is a substituent shown in formula (2). However, R 6 ~R 8 are each independently a hydrogen atom or an arbitrary substituent, and R 6 ~R 8 At least one of the substituents is an alkyl group having 4 or more carbon atoms, and R 9 is a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group, and Z is a sulfur atom, an oxygen atom, or a direct bond.

6. R of the compound shown in formula (1) above 1 ~R 4 The anti-biofilm agent according to claim 1 or 2, characterized in that at least one of the alkyl groups having 4 or more carbon atoms is a tert-butyl group.

7. An anti-biofilm agent according to claim 1 or 2, characterized in that the solubility of the compound represented by formula (1) in water at 25°C is 0.08 g / 100 mL or less.

8. An anti-biofilm agent according to claim 1 or 2, characterized in that the molecular weight of the compound represented by formula (1) is 150 or more and 500 or less.

9. An anti-biofilm agent according to claim 1 or 2, characterized in that the constituent atoms of the compound shown in the above formula (1) do not contain any atoms other than carbon atoms, oxygen atoms, hydrogen atoms, nitrogen atoms and sulfur atoms.

10. An anti-biofilm resin composition comprising the anti-biofilm agent according to claim 1 or 2 and a synthetic resin.

11. An anti-biofilm paint comprising the anti-biofilm agent according to claim 1 or 2, a binder, and a solvent.

12. An anti-biofilm product comprising a substrate and the anti-biofilm agent according to claim 1 or 2.

Images