Antimicrobial compositions, fibers or clothing, and films

Abstract

To provide a novel antimicrobial composition having a wider antimicrobial spectrum, and also to provide a fiber or clothing, and a film using the antimicrobial composition.SOLUTION: The antimicrobial composition includes a compound expressed by a general formula (1) or a salt thereof, or solvates thereof as an active ingredient. In the general formula (1), X1 denotes *-OR1, R1 denotes a hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent group, X2 denotes *-R2-OH, R2 denotes a hydrocarbon group having 1 to 10 carbon atoms, which may have a substituent group, * denotes a bonding hand to be bonded with a benzene ring, and n1 and n2 independently denote an integer of 1 to 5, and 2≤n1+n2≤6.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an antibacterial composition, a fiber or a clothing article, and a film.

Background Art

[0002] Conventionally, various antibacterial compositions have been used as therapeutic agents for bacterial infections or fungal infections. For example, Non-Patent Document 1 describes a therapeutic agent for fungal infections containing clotrimazole having antibacterial properties.

[0003] Also, various compounds having antibacterial properties are used as additives for maintaining the quality of food. Non-Patent Document 2 describes organic acids, polylysine, etc. having antibacterial properties as food additives.

Prior Art Documents

Non-Patent Documents

[0004]

Non-Patent Document 1

Non-Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] In recent years, antibacterial compositions showing antibacterial effects (i.e., a broad antibacterial spectrum) against many microbial species have been demanded. In this specification, "having a broad antibacterial spectrum" means having antibacterial properties against both bacteria and molds. The present invention aims to provide a new antibacterial composition with a broad antibacterial spectrum, as well as fibers or clothing items and films using the antibacterial composition.

Means for Solving the Problems

[0006] The present invention includes the following aspects. That is, the first aspect of the present invention is an antibacterial composition containing, as an active ingredient, one or more selected from the group consisting of a compound represented by the following general formula (1), a salt of the compound, a solvate of the compound, and a solvate of the salt of the compound.

[0007]

Chemical formula

[0009] , 21 is *-OR 1 where R 1 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. X 2 is *-R 2 -OH. R 2 is a hydrocarbon group having an optional substituent and having 1 to 10 carbon atoms. * is a bond that binds to the benzene ring. n1 and n2 are each independently an integer of 1 to 5, and 2 ≤ n1 + n2 ≤ 6.]

[0008] In the first aspect of the present invention, the compound in the general formula (1) is preferably a compound represented by the following general formula (1A).

Chemical formula

[0009] In a first aspect of the present invention, the antibacterial composition may be a pharmaceutical composition, a shelf-life improving composition, a food and beverage composition, an oral or skin hygiene product, an odor prevention or reduction agent, a cleaning composition, or a cosmetic composition.

[0010] Furthermore, a second aspect of the present invention is a textile or clothing containing the antibacterial composition of the first aspect.

[0011] Furthermore, a third aspect of the present invention is a film comprising at least a resin layer containing the antibacterial composition of the first aspect. [Effects of the Invention]

[0012] According to the present invention, it is possible to provide a novel antimicrobial composition with a broad antimicrobial spectrum, as well as fibers or clothing and films using the antimicrobial composition. [Brief explanation of the drawing]

[0013] [Figure 1] This figure shows the synthesis scheme of 4-[(3-methyl-2-buten-1-yl)oxy]benzenemethanol in Experimental Example 1. [Figure 2] This figure shows the NMR spectrum of the final standard synthesized in Experimental Example 1. [Modes for carrying out the invention]

[0014] In this specification and in the claims thereof, "alkyl group" includes linear, branched, and cyclic monovalent saturated hydrocarbon groups unless otherwise specified. Unless otherwise specified, the term "alkylene group" includes linear, branched, and cyclic divalent saturated hydrocarbon groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0015] (Antibacterial composition) The antibacterial composition according to this embodiment contains one or more active ingredients selected from the group consisting of a compound represented by the following general formula (1), a salt of the compound, a solvate of the compound, and a solvate of a salt of the compound.

[0016] [ka] [In formula (1), X 1 is, *-OR 1 That is. R 1 X is a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. 2 is, *-R 2 -OH is R 2 is a hydrocarbon group having 1 to 10 carbon atoms, which may have substituents. * is a bond attached to a benzene ring. n1 and n2 are each independently integers from 1 to 5, such that 2 ≤ n1 + n2 ≤ 6.

[0017] The antibacterial composition according to this embodiment exhibits antibacterial properties by containing the above-mentioned active ingredient. In this specification, "antibacterial properties" means the property of killing microorganisms or inhibiting the growth of microorganisms. The microorganisms are not particularly limited, but examples include molds and bacteria.

[0018] In formula (1), X 1 In R 1 Examples of hydrocarbon groups include chain-like hydrocarbon groups having 1 to 20 carbon atoms, or alicyclic hydrocarbon groups having 3 to 20 carbon atoms. R 1 If is a linear hydrocarbon group, the linear hydrocarbon group may be linear or branched. The linear hydrocarbon group may be saturated or unsaturated. The number of carbon atoms in the linear hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, even more preferably 2 to 8, and particularly preferably 3 to 7. R 1When is an alicyclic hydrocarbon group, the alicyclic hydrocarbon group may be a polycyclic group or a monocyclic group. As a monocyclic alicyclic hydrocarbon group, a group obtained by removing one or more hydrogen atoms from a monocycloalkane is preferred. As a polycyclic alicyclic hydrocarbon group, a group obtained by removing one or more hydrogen atoms from a polycycloalkane is preferred. R 1 Examples of substituents in this compound include amino groups, hydroxyl groups, carboxyl groups, acyl groups, alkoxy groups, carbonyl groups, and halogen atoms. For n1, values ​​from 1 to 3 are preferred, with 1 being more preferred. In equation (1), when n1 is 2 or greater, there are multiple X 1 They may be the same or different from one another.

[0019] X 1 A group represented by the following general formula (X1A) is preferred.

[0020] [ka] [In formula (1A), R 11 R is an alkylene group or single bond having 1 to 3 carbon atoms. 12 , R 13 , R 14 Each of these is independently an alkyl group or hydrogen atom having 1 to 3 carbon atoms. * represents a bond attached to a benzene ring.

[0021] R 11 The preferred elements are a methylene group, an ethylene group, a trimethylene group, -CH2-CH(CH3)-, -CH(CH3)-CH2-, or a single bond; a methylene group, an ethylene group, or a single bond is more preferred; and a methylene group is even more preferred. R 12 The preferred group is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a hydrogen atom, more preferably a methyl group or a hydrogen atom, and even more preferably a hydrogen atom. R 13 and R 14 The preferred group is a methyl group, an ethyl group, or a hydrogen atom, with a methyl group being preferred.13 and R 14 They may be the same or they may be different.

[0022] In formula (1), X 2 In R 2 Examples of hydrocarbon groups include chain-like hydrocarbon groups having 1 to 10 carbon atoms, or alicyclic hydrocarbon groups having 3 to 10 carbon atoms. R 2 As for hydrocarbon groups in R, 1 An example is a hydrocarbon group from which one hydrogen atom has been removed. 2 When the compound is a linear hydrocarbon group, the number of carbon atoms in the linear hydrocarbon group is preferably 1 to 8, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 1. R 2 As substituents in this case, R 1 Similar examples include the above. R 2 Chain-like hydrocarbon groups are preferred, and saturated chain-like hydrocarbon groups are more preferred. For n2, values ​​from 1 to 3 are preferred, with 1 being more preferred. In equation (1), when n² is 2 or greater, there are multiple X 2 They may be the same or different from one another.

[0023] In formula (1), X 1 and X 2 The bonding position of the atom to the benzene ring is not particularly limited. If both n1 and n2 are 1, then X 2 X 1 The relative position may be ortho, meta, or para, with the para position being preferable.

[0024] As the compound represented by the above general formula (1), the compound represented by the following general formula (1A) is preferred.

[0025] [ka] [In formula (1A), R11 R is an alkylene group or single bond having 1 to 3 carbon atoms. 12 , R 13 , R 14 Each of these is independently an alkyl group having 1 to 3 carbon atoms or a hydrogen atom. 21 This is an alkylene group having 1 to 3 carbon atoms.

[0026] R 11 , R 12 , R 13 , R 14 Preferred groups include those mentioned above in the general formula (X1A).

[0027] R 21 The preferred group is a methylene group, an ethylene group, a trimethylene group, -CH2-CH(CH3)-, or -CH(CH3)-CH2-, with a methylene group or an ethylene group being more preferred, and a methylene group being even more preferred.

[0028] In the compound represented by formula (1A), the relative positions of the two substituents on the benzene ring may be ortho, meta, or para, with the para position being preferable.

[0029] As the compound represented by the above general formula (1), the compound represented by the following chemical formula (1-1) is preferred. The CAS number of the compound represented by the following chemical formula (1-1) is 34593-47-0. The common name of the compound represented by the following chemical formula (1-1) is 4-[(3-methyl-2-buten-1-yl)oxy]benzenemethanol.

[0030] [ka]

[0031] The salts of the compounds represented by the above general formula (1) that may be included in the antimicrobial composition according to this embodiment are not particularly limited as long as the antimicrobial composition is effective, and examples include sodium salts, potassium salts, calcium salts, aluminum salts, zinc salts, magnesium salts, choline salts, ammonium salts, hydrochloride salts, sulfates, hydrobromide salts, hydroiodide salts, phosphates, nitrates, benzoates, methanesulfonates, 2-hydroxyethanesulfonates, p-toluenesulfonates, acetates, propaneates, oxalates, malons, succinates, glutarates, adipates, tartrates, maleates, fumarates, malates, mandelates, and the like.

[0032] The solvates of the compound represented by the above general formula (1) or its salts that may be included in the antimicrobial composition according to this embodiment are not particularly limited as long as the antimicrobial composition is effective, and examples include hydrates, organic solvent hydrates, etc.

[0033] The active ingredient contained in the antibacterial composition according to this embodiment may be either a natural product or a synthetic product.

[0034] <Other ingredients> The antibacterial composition according to this embodiment may contain other components in addition to the above-mentioned active ingredients. Other components are not particularly limited as long as they allow the antibacterial composition to exert its effect, and include, for example, excipients, bulking agents, binders, wetting agents, disintegrants, surfactants, lubricants, dispersants, buffers, preservatives, solubilizers, antiseptics, flavoring and deodorizing agents, stabilizers, pH adjusters, antioxidants, antiseptics, humectants, skin protectants, cooling agents, fragrances, colorants, chelating agents, antiperspirants, plant extracts, animal extracts, oily bases, emulsifiers, emulsifying stabilizers, powder components, polymer components, tackifiers, film-forming agents, shape-retaining agents, lubricants, etc., as described later.

[0035] <Content> The amount of active ingredient contained in the antibacterial composition according to this embodiment is not particularly limited as long as the antibacterial composition is effective, and can be appropriately adjusted according to the dosage form, etc., and may be, for example, 0.0001% by mass or more and 50% by mass or less, based on the total mass (100% by mass) of the antibacterial composition.

[0036] <Dosage Form> The dosage form of the antimicrobial composition according to this embodiment is not particularly limited as long as the effects of the present invention are achieved, and may be any dosage form such as liquid, powder, granules, or tablets. When the dosage form of the antimicrobial composition according to this embodiment is liquid, the amount of active ingredient contained in the antimicrobial composition according to this embodiment is not particularly limited as long as the antimicrobial composition is effective, and may be, for example, 0.1% by mass or more and 50% by mass or less, based on the total mass (100% by mass) of the antimicrobial composition.

[0037] <Application> The uses of the antibacterial composition according to this embodiment are not particularly limited as long as the effects of the present invention are achieved. For example, it can be used by incorporating it into pharmaceutical compositions, food compositions, quasi-drug compositions, oral or skin hygiene products, odor prevention or reduction agents, cleaning compositions, cosmetic compositions, or textile or clothing materials.

[0038] The antibacterial composition according to this embodiment can exhibit antibacterial properties against microorganisms such as bacteria and molds. The antibacterial composition according to this embodiment can exhibit antibacterial properties on objects in the living environment by being sprayed or applied to them. The objects of interest in the living environment are not particularly limited, but examples include daily necessities such as tableware, eyeglasses, watches, and mobile phones; office supplies such as desks and writing instruments; and items used in wet areas such as washrooms, kitchens, bathrooms, and toilets.

[0039] The antibacterial composition of the above embodiment may be a pharmaceutical composition, a composition for improving shelf life, a food and beverage composition, an oral or skin hygiene product, an odor prevention or reduction agent, a cleaning composition, or a cosmetic composition.

[0040] (Pharmaceutical composition) The antibacterial composition of the above embodiment may be a pharmaceutical composition. The aforementioned pharmaceutical composition may contain an effective amount of the active ingredient and a pharmaceutically acceptable carrier.

[0041] The pharmaceutical composition may be administered orally. In this case, examples of pharmaceutically acceptable carriers that may be included in the pharmaceutical composition include solvents such as sterile water and physiological saline; binders such as gelatin, corn starch, tragacanth gum, and gum arabic; excipients such as crystalline cellulose; and leavening agents such as alginic acid. By orally ingesting such a pharmaceutical composition, it is possible to effectively prevent and / or treat conditions such as gastritis, gastric ulcers, duodenal ulcers, atrophic gastritis, and gastric cancer caused by infection with Helicobacter pylori. Furthermore, it is possible to effectively prevent and / or treat conditions such as arteriosclerosis, liver damage, colon cancer, constipation, diarrhea, and weakened immunity caused by harmful bacteria present in the intestines, such as Clostridium perfringens, Staphylococcus aureus, Pseudomonas aeruginosa, Veillonella, and Escherichia coli.

[0042] Alternatively, the pharmaceutical composition may be administered transdermally. In this case, examples of pharmaceutically acceptable carriers that may be included in the pharmaceutical composition include oily bases, emulsifiers, emulsifying stabilizers, solubilizers, powder components, polymer components, tackifiers, film-forming agents, shape-retaining agents, lubricants, and the like. By ingesting such a pharmaceutical composition transdermally, it is possible to effectively prevent and / or treat skin bacterial infections caused by infections such as Staphylococcus and Streptococcus; and skin fungal infections caused by infections such as yeast, filamentous fungi, and dermatophytes.

[0043] (Composition for improving shelf life) The antibacterial composition of the above embodiment may be a composition for improving shelf life. The aforementioned shelf-life-extending composition may be contained inside food or beverages or other objects, or it may be applied from the outside by coating or spraying.

[0044] The foods and beverages to which the aforementioned shelf-life-enhancing composition is added are not particularly limited, but examples include beverages such as tea drinks, soft drinks, milk drinks, vegetable drinks, alcoholic beverages, and nutritional drinks; ingredients such as meat, fish, vegetables, grains, dairy products, egg products, and processed products thereof; and seasonings such as sauces, spices, oils, and herbs.

[0045] The shelf-life-enhancing composition according to this embodiment is typically used by adding it to food and beverages, and by suppressing the growth of microorganisms in the food and beverages, it is possible to suppress deterioration and spoilage of the food and beverages.

[0046] (Food and drink composition) The antibacterial composition of the above embodiment may be a food or beverage composition. The food and beverages in the aforementioned food and beverage composition are not particularly limited, but examples include those similar to the food and beverages exemplified in the composition for improving shelf life.

[0047] By ingesting such a food or beverage composition, it is possible to achieve the effects that would occur if the pharmaceutical composition were taken orally.

[0048] (Oral or skin hygiene products) The antibacterial composition of the above embodiment may be an oral or skin hygiene product. Examples of the aforementioned oral hygiene products include toothpaste, mouthwash, gum massage cream, lozenges, tablets, chewing gum, and dental floss. The aforementioned oral hygiene composition can exert an effect of killing or inhibiting the growth of microorganisms in the oral cavity. As a result, it can be effective in keeping the oral cavity clean, preventing bad breath, and preventing or treating tooth decay, periodontitis, gingivitis, etc.

[0049] Examples of the aforementioned skin hygiene products include, for example, cleansing tissues and towels for wiping hands, buttocks, feet, and the whole body, wet wipes, body soap, hand soap, soap, bath additives, bandages, hand cream and other body care products, skin care products such as facial cleansing foam, facial cleansing cream and acne preventatives, shaving cream, shaving lotion and shaving foam, etc. These skin hygiene products can act on microorganisms that adhere to the skin to keep the skin surface clean and are effective in suppressing inflammatory reactions of the skin.

[0050] (An agent for preventing or reducing unpleasant odors) The antibacterial composition of the above embodiment may also be an odor-preventing or odor-reducing agent. Examples of the odor-preventing or reducing agents include deodorant sprays, deodorant lotions, body odor preventatives, excrement deodorizers, toilet deodorizers, pet deodorizers, deodorizing sheets, clothing deodorizers, and sludge deodorizers. These odor-preventing or reducing agents can exert a killing or growth-inhibiting effect on microorganisms that come into contact with organic matter such as excrement and secretions. This makes it possible to effectively prevent or reduce odors generated by microorganisms.

[0051] (Cleaning composition) The antibacterial composition of the above embodiment may be a cleaning composition. Examples of the cleaning composition include instrument cleaning compositions such as medical instrument cleaning compositions and dishwashing and disinfection compositions. By cleaning instruments with the cleaning composition, it is possible to kill or inhibit the growth of microorganisms attached to the instruments. This makes it possible to clean the instruments.

[0052] (Cosmetic composition) The antibacterial composition of the above embodiment may be a cosmetic composition. Examples of the cosmetic composition include emulsions, ointments, creams, lotions, toners, face masks, foundations, face powders, blushes, lipsticks, mascaras, eyebrow products, eyeliners, eyeshadows, cleansers, nail polishes, and hair care products. The cosmetic composition can exert an effect of killing or inhibiting the growth of microorganisms on the skin surface and microorganisms mixed into the cosmetic composition. This makes it possible to keep the skin surface clean and also allows the cosmetic composition to exert an effect as a preservative.

[0053] The effective amount of the active ingredient contained in each composition of the embodiments described above is not particularly limited as long as each composition exhibits the effects of the present invention, and can be appropriately determined by those skilled in the art. Furthermore, the method and amount of use of each composition are not particularly limited, as long as each composition is effective against the target microorganism, and can be appropriately determined by those skilled in the art.

[0054] (Textiles or clothing) The fibers or clothing according to this embodiment contain the antibacterial composition according to the above embodiment.

[0055] Examples of the aforementioned fibers include plant fibers such as cotton and linen; animal fibers such as silk and wool; synthetic fibers such as nylon, polyester, acrylic, polyvinyl chloride, and polyurethane; semi-synthetic fibers such as acetate, triacetate, and promix; regenerated fibers such as rayon, cupro, and polynosic; and inorganic fibers such as glass and metal.

[0056] Examples of the aforementioned clothing items include shirts, trousers, underwear, socks, sportswear, hats, masks, carpets, bedding, bedding covers, medical white coats, and the like.

[0057] In the aforementioned fibers or garments, the active ingredient may be added to the material of the fiber or garment before molding and then spun. Alternatively, the active ingredient may be impregnated, sprayed, or coated onto the fiber or garment after molding. The aforementioned fibers or clothing items can exert an effect of killing or inhibiting the growth of microorganisms. This allows the fibers or clothing items to be kept clean.

[0058] (film) The film according to this embodiment comprises at least a resin layer containing the antibacterial composition according to the above embodiment.

[0059] The resin used as the material for the resin layer is not particularly limited as long as the effects of the present invention are achieved, and examples include polyethylene, polypropylene, polybutylene, polyphenylene, polystyrene, polyester, polyvinyl alcohol, olefin, polyarylate, polyether, polyalkylene terephthalate, polyacrylic acid, polyamide, polyimide, polyaminobismaleimide, bismaleimide, cellulose, cellulose acetate, cellulose acetate butyrate, ethylcellulose, celluloid, carboxymethylcellulose, epoxy, melamine, acrylonitrile butadiene styrene, cresol, casein, epoxy, phenol, polycarbonate, diallyl phthalate, polytetrafluoroethylene, polyurethane, vinyl acetate, vinyl chloride, silicone, urea, and the like.

[0060] The film according to this embodiment may be a multilayer film comprising layers other than the resin layer containing the antibacterial composition. Examples of other layers include layers known to those skilled in the art, such as a base layer, an outer layer, and a sealant layer (see, for example, International Publication No. 2008 / 139593 and Japanese Patent Application Publication No. 2017-019237).

[0061] If the film according to this embodiment includes a layer other than the resin layer containing the antibacterial composition, the resin layer containing the antibacterial composition is preferably a sealant layer. When the resin layer containing the antibacterial composition is a sealant layer, the active ingredients contained in the sealant layer can exhibit antibacterial properties in the object packaged in the film.

[0062] In the film according to this embodiment, the ratio of the content of the active ingredient to the total mass of the resin layer containing the antibacterial composition is not particularly limited as long as antibacterial properties are exhibited in the object packaged by the film, but may be, for example, 0.0001% by mass or more and 10% by mass or less.

[0063] The packaging comprising the film according to this embodiment can exhibit antibacterial properties against its contents. Examples of contents include food products.

[0064] <Target bacteria> In the embodiments described above, examples of microorganisms that exhibit antibacterial properties with the antibacterial composition include molds and bacteria.

[0065] The molds mentioned in this embodiment are not particularly limited as long as they are molds that exhibit antibacterial properties, and examples include the genera Aspergillus, Penicillium, Cladosporium, Eurotium, Mucor, Scopulariopsis, Wallemia, Alternaria, Fusarium, Geotrichum, Phialophora, Colletotrichum, Ulocladium, Phoma, Arthrinium, Aureobasidium, Trichoderma, Rhizoctonia, Neurospora, Arthrinium, Rhizopus, Cunninghamella, and Curvularia. Among these, the control method according to this embodiment is useful against one or more species of fungus selected from the group consisting of the genera Aspergillus, Penicillium, and Cladosporium.

[0066] The bacteria are not particularly limited as long as the control method according to this embodiment exhibits antibacterial properties, and include, for example, Escherichia, Staphylococcus, Streptococcus, Enterococcus, Micrococcus, Corynebacterium, Bacillus, Listeria, Peptococcus, Peptostreptococcus, Clostridium, Eubacterium, Propionibacterium, Lactobacillus, Neisseria, Branhamella, Haemophilus, Bordetella, Citrobacter, Salmonella, Shigella, and Klebsi. ella, Enterobacter, Serratia, Hafnia, Proteus, Morganella, Providencia, Yersinia, Campylobacter, Vibrio, Aeromonas, Pseudomonas, Xanthomonas, Acinetobacter, Flavobacteri Examples include the genus Um, Brucella, Legionella, Veillonella, Bacteroides, Fusobacterium, Mycobacterium, Actinomyces, Nocardia, Treponema, Leptspira, Mycoplasma, Rickettsia, Chlamydia, and the like. Among these, the control method according to this embodiment is useful against one or more bacteria selected from the group consisting of the genera Escherichia and Staphylococcus. [Examples]

[0067] The present invention will be described below with reference to examples, but the present invention is not limited to the following examples.

[0068] [Experimental Example 1] The compound represented by the above chemical formula (1-1) (i.e., 4-[(3-methyl-2-buten-1-yl)oxy]benzenemethanol) was synthesized by the method described below. The synthesis scheme is shown in Figure 1.

[0069] 5 g of 4-hydroxybenzaldehyde (Tokyo Chemical Industries H0198) was placed in an Ar-substituted two-necked flask, to which 20 mL of anhydrous acetone and 9.68 g of potassium carbonate were added, and then 4.28 g of 1-chloro-3-methyl-2-butene (Tokyo Chemical Industries C1290) was added, and the mixture was stirred at room temperature for 20 hours.

[0070] Next, the solid obtained by filtration was washed with acetone and dissolved in ethyl acetate. The resulting ethyl acetate solution was dehydrated with magnesium sulfate, the magnesium sulfate was removed by filtration, and the solution was concentrated using an evaporator. The resulting concentrate was purified by silica gel column chromatography to obtain 1.88 g of 4-(3-methyl-2-butenyloxy)benzaldehyde.

[0071] Next, 10.9 ml of ethanol was added to 1.2 g of 4-(3-methyl-2-butenyloxy)benzaldehyde, and then 0.72 g of sodium borohydride was added at 5°C and the mixture was stirred for 5 hours. Next, methylene chloride and water were added to the reaction solution and liquid-liquid extraction was performed. Water was then added again to the methylene chloride phase and liquid-liquid extraction was performed once more. After dehydration by adding magnesium sulfate to the recovered methylene chloride phase, the magnesium sulfate was removed by filtration. The resulting filtrate was concentrated using an evaporator to obtain 0.99 g of the final standard.

[0072] The final sample was analyzed by NMR. The resulting NMR spectrum is shown in Figure 2. The analysis results were as follows: 4-[(3-methyl-2-buten-1-yl)oxy]benzenemethanol: 1H-NMR (CDCl3,600MHz):7.27(d,2H,C-2),6.91(d,2H,C-3),5.49(m,1H,CH=),4.60(d,2H,-O-CH 2),4.50(d,2H,CH2-OH),1.80(brs,3H,trans-CH3),1.74(brs,3H,cis-CH3),1.52(m,1H,CH2-OH)

[0073] Analysis confirmed that the final standard was the compound represented by the above chemical formula (1-1) (i.e., 4-[(3-methyl-2-buten-1-yl)oxy]benzenemethanol).

[0074] [Experimental Example 2] The compound represented by the above chemical formula (1-1) synthesized in Experimental Example 1 (i.e., 4-[(3-methyl-2-buten-1-yl)oxy]benzenemethanol) was used to evaluate its antimicrobial activity against mold.

[0075] The compound represented by the above chemical formula (1-1) was dissolved in methanol to prepare a 10% by mass methanol solution, which was designated as Example 1. In addition, 10% by mass methanol solutions were prepared for triacetin and 2,6-diisopropylnaphthalene, respectively, and these were designated as Comparative Example 1 and Comparative Example 2.

[0076] (Antibacterial test against mold) <Antibacterial Test A-1> Antimicrobial tests were conducted against Aspergillus niger. Potato dextrose agar was added dropwise to each well of a 12-well plate at a concentration of 2 ml each. Before the medium solidified, the three concentrations of 10% by mass methanol solutions described above were added dropwise. The final concentrations of the reagents in each medium were 6400 ppm, 3200 ppm, 1600 ppm, 800 ppm, 400 ppm, 200 ppm, and 100 ppm. Next, the solidified agar is mixed with a spore solution of Aspergillus oryzae (1 x 10⁻¹⁰ bacteria). 65 μL of cfu / ml was inoculated. The plate was covered and incubated at 25°C for 72 hours. A control sample was also prepared with 5 μL of methanol added.

[0077] <Antibacterial Test A-2> An antibacterial test was conducted against Penicillium citrinum. The spore extract of Penicillium citrinum (bacterial count 1 × 10⁶) was used. 6 A sample (cfu / ml) was prepared and an antibacterial test was performed in the same manner as for Aspergillus oryzae.

[0078] An antibacterial test was conducted against the black mold (Cladosporium sphaerospermum). The black mold spore extract (bacterial count 1 × 10⁻⁶) was used. 6 A sample (cfu / ml) was prepared and an antibacterial test was performed in the same manner as for Aspergillus oryzae.

[0079] (Evaluation method) The plates were visually inspected after culturing, and the lowest concentration at which no mycelium was detected was evaluated as the minimum inhibitory concentration. The results are shown in Table 1.

[0080] [Table 1]

[0081] The minimum inhibitory concentrations for both triacetin and 2,6-diisopropylnaphthalene were over 6400 ppm. In contrast, the minimum inhibitory concentration for the compound represented by the above chemical formula (1-1) was 200-400 ppm. From the above results, it was confirmed that the compound represented by the above chemical formula (1-1) exhibits antibacterial activity against molds such as Aspergillus niger, Penicillium fuciformis, and Black mold.

[0082] [Experimental Example 3] The compound represented by the above chemical formula (1-1), synthesized in Experimental Example 1, was used to evaluate its antibacterial activity against bacteria.

[0083] (Antibacterial test against bacteria) <Antibacterial Test B-1> Antimicrobial tests were conducted against Escherichia coli. Standard agar medium was added dropwise to each well of a 12-well plate (2 ml each). Before the medium solidified, the three 10% methanol solutions of different concentrations prepared in Experimental Example 2 were added dropwise. The final concentrations of the reagents in each medium were set in the same manner as in Experimental Example 2. Next, the solidified agar is mixed with a bacterial solution of E. coli (bacterial count 1 x 10⁻¹⁰). 6 5 μL of cfu / ml was inoculated. The plate was covered and incubated at 35°C for 24 hours. A control sample was also prepared with 5 μL of methanol added.

[0084] <Antibacterial Test B-2> An antibacterial test was conducted against Staphylococcus aureus. (Bacterial count: 1 × 10⁶) 6 A sample (cfu / ml) was prepared and subjected to antimicrobial testing in the same manner as for E. coli.

[0085] The cultured plates were visually inspected, and the lowest concentration at which no colonies were observed was evaluated as the minimum inhibitory concentration.

[0086] [Table 2]

[0087] The minimum inhibitory concentrations for both triacetin and 2,6-diisopropylnaphthalene were over 6400 ppm. In contrast, the minimum inhibitory concentration for the compound represented by the above chemical formula (1-1) was 400-800 ppm. From the above results, it was confirmed that the compound represented by the above chemical formula (1-1) exhibits antibacterial activity against bacteria such as Escherichia coli and Staphylococcus aureus. [Industrial applicability]

[0088] According to the present invention, it is possible to provide a novel antimicrobial composition with a broad antimicrobial spectrum, as well as fibers or clothing and films using the antimicrobial composition. This antimicrobial composition is suitable for applications that suppress the growth of microorganisms such as bacteria and molds on objects in living spaces.

Claims

1. An antimicrobial composition containing, as an active ingredient, one or more selected from the group consisting of a compound represented by the following chemical formula (1-1), a salt of the compound, a solvate of the compound, and a solvate of a salt of the compound. 【Chemistry 1】

2. The antibacterial composition according to claim 1, which is a pharmaceutical composition, a composition for improving shelf life, a food and beverage composition, an oral or skin hygiene product, an odor prevention or reduction agent, a cleaning composition, or a cosmetic composition.

3. A textile or clothing item comprising the antibacterial composition described in claim 1.

4. A film comprising at least a resin layer containing the antibacterial composition described in claim 1.

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