Antibacterial or antiviral agent

Abstract

The purpose of the present invention is to provide a novel antibacterial or antiviral agent capable of imparting an antibacterial or antiviral effect to spaces, articles, human bodies, and the like. An antibacterial or antiviral agent containing at least one compound selected from the group consisting of 2-cyclohexene-1-one, alpha-angelica lactone, 2-cyclopentene-1-one, (E, E)-2, 4-hexadienal, propionaldehyde, butyraldehyde, branched aldehydes having a molecular weight of 150 or less, and cyclic aldehydes.

Description

Technical Field

[0001] The present disclosure relates to an antibacterial or antiviral agent capable of imparting an antibacterial or antiviral effect to a space, an object, a human body, or the like. Background Art

[0002] The growth of bacteria and viruses can cause deterioration of the living environment, corruption, infection, etc., so countermeasures using antibacterial or antiviral agents are used. Conventional antibacterial or antiviral agents are mostly non-volatile, but volatile antibacterial or antiviral agents are also known.

[0003] Non-volatile antibacterial or antiviral agents need to be directly attached to or contained in an object for use. In contrast, volatile antibacterial or antiviral agents can be spread to every corner of the target space or the target object by simply being set in the target space or the space where the target object is located and volatilizing. This makes the antibacterial or antiviral effect spread to every corner of the target space or the target object, and is excellent in terms of ease of use.

[0004] In the past, as volatile antibacterial agents, diacetyl, thymol, (E)-2-hexenal, trans-2-hexenyl acetate, linalool, 1,8-cineole, acetoin (see Patent Document 1 for the above). 2-methylpropionic acid 2,2-dimethyl-1-(2-hydroxy-1-methylethyl)propyl ester or its derivatives (see Patent Document 2), capillaris diynone (Patent Document 3), etc. have been reported. In recent years, awareness of countermeasures against infectious diseases and awareness of cleanliness have increased, and further development of antibacterial or antiviral agents has been required. Prior art literature Patent Literature

[0005] Patent Document 1: Japanese Patent Application Publication No. 2001-29054 Patent Document 2: Japanese Patent Application Publication No. 2016-44153 Patent Document 3: Japanese Patent Application Publication No. 2015-39353 Summary of the invention Technical problem to be solved by the invention

[0006] The object of the present disclosure is to provide a new antibacterial or antiviral agent that can impart an antibacterial or antiviral effect to a space, an article, a human body, or the like. Technical solutions for solving technical problems

[0007] The present inventors have conducted in-depth research to solve the above technical problems, and found that 2-cyclohexene-1-one (Japanese original: 2-shikrohexen-1-one), α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched aldehydes with a molecular weight of 150 or less, and cyclic aldehydes have excellent antibacterial or antiviral effects and can be used as antibacterial or antiviral agents. In addition, the present inventors have found that the above compounds are volatile and can impart antibacterial or antiviral effects to objects even in the volatilized state. The present invention is completed by further repeated research based on these insights.

[0008] That is, the present disclosure provides inventions in the following disclosed aspects. Item 1. An antibacterial or antiviral agent, comprising as an active ingredient at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes having a molecular weight of 150 or less, and cyclic aldehydes. Item 2. An antibacterial or antiviral agent according to Item 1, wherein the active ingredient is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural. Item 3. An antibacterial or antiviral composition for use in a space, comprising the antibacterial or antiviral agent according to Item 1 or 2, and a solvent. Item 4. An antibacterial or antiviral composition for an article, comprising the antibacterial or antiviral agent according to Item 1 or 2, and a solvent. Item 5. The antibacterial or antiviral composition for an article according to Item 4, wherein the article is a fiber product. Item 6. Use of a compound for antibacterial or antiviral treatment of spaces or articles, wherein the compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes with a molecular weight of less than 150, and cyclic aldehydes. Item 7. The use according to Item 6, wherein the compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural. Item 8. Use of a composition for use as an antibacterial or antiviral composition for use in space, the composition comprising at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes with a molecular weight of less than 150, and cyclic aldehydes, and a solvent. Item 9. Use of a composition as an antibacterial or antiviral composition for an article, the composition comprising at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes having a molecular weight of less than 150, and cyclic aldehydes, and a solvent. Item 10. The use according to Item 9, wherein the article is a fiber product. Item 11. An antibacterial or antiviral method, which uses at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched chain aldehydes with a molecular weight of less than 150, and cyclic aldehydes to treat an object requiring antibacterial or antiviral properties. Item 12. The method according to Item 11, wherein the compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural. Item 13. The method according to Item 11 or 12, wherein the object to be treated with antibacterial or antiviral agents is a space. The space is treated with the compound. Item 14. The method according to Item 11 or 12, wherein the object to be treated with antibacterial or antiviral agents is an article. The article is treated with the compound. Item 15. The method according to Item 14, wherein the article is a fiber product. Effects of the Invention

[0009] According to the present disclosure, a novel antibacterial or antiviral agent is provided. In addition, the antibacterial or antiviral agent of the present disclosure can not only impart an antibacterial or antiviral effect to the space by volatilizing it in the space, but also impart an antibacterial or antiviral effect to objects present in the space and components that divide the space, thereby making the living space a hygienic environment in a simple way and reducing the risk of contracting an infection. In addition, since bacteria present in the living space are also the cause of bad odor, the antibacterial or antiviral agent of the present disclosure can prevent and remove bad odor, and can also create a comfortable living space. DETAILED DESCRIPTION

[0010] 1. Definition In the present disclosure, the expression "X to Y" related to a numerical range represents a numerical range of not less than X and not more than Y.

[0011] In the present disclosure, a branched aldehyde refers to an aldehyde having a branched carbon skeleton.

[0012] In the present disclosure, a cyclic aldehyde refers to a compound having a cyclic structure and an aldehyde group (—CH(═O)).

[0013] In the present disclosure, volatility means volatilization at normal temperature and pressure (20° C., 1 atmosphere).

[0014] In the present disclosure, antibacterial refers to reducing the activity of bacteria, killing bacteria or inhibiting their growth. In addition, in the present disclosure, antiviral refers to reducing the activity of viruses, causing virus reduction, reduced viral infectivity, or inhibition of viral growth. In the present disclosure, antibacterial or antiviral agents refer to substances used for antibacterial or antiviral purposes.

[0015] In the present disclosure, the antibacterial or antiviral composition for space refers to a composition used for treating a space with an antibacterial or antiviral agent for the purpose of antibacterial or antiviral treatment of the space.

[0016] In the present disclosure, the antibacterial or antiviral composition for articles refers to a composition used for treating articles with an antibacterial or antiviral agent for the purpose of treating the articles with antibacterial or antiviral agents.

[0017] In the present disclosure, the antibacterial or antiviral external composition refers to a composition to be applied to the skin for antibacterial or antiviral purposes.

[0018] In the present disclosure, the antibacterial or antiviral method refers to a method of imparting an antibacterial or antiviral effect to a subject requiring the antibacterial or antiviral effect.

[0019] In the present disclosure, a hard surface refers to a surface of a hard member such as resin, ceramic, or glass.

[0020] 2. Antibacterial or antiviral agents The antibacterial or antiviral agent of the present invention is characterized in that at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched chain aldehydes with a molecular weight of 150 or less, cyclic aldehydes, and (E,E)-2,4-hexadienal is used as an active ingredient. The antibacterial or antiviral agent of the present invention is described in detail below.

[0021] [Active ingredients] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is 2-cyclohexen-1-one (CAS 930-67-7). 2-cyclohexen-1-one is a kind of volatile cyclic ketone.

[0022] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is alpha-angelicalactone (CAS 591-12-8). α-Angelica lactone is a volatile lactone.

[0023] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is 2-cyclopenten-1-one (CAS 930-30-3). 2-Cyclopenten-1-one is a type of volatile cyclic ketone.

[0024] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is (E,E)-2,4-hexadienal (trans,trans-2,4-hexadienal; CAS 142-83-6). (E,E)-2,4-hexadienal is a type of volatile straight-chain aldehyde.

[0025] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is propionaldehyde (CAS 123-38-6). Propionaldehyde is a type of volatile straight-chain aldehyde.

[0026] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is butyraldehyde (CAS 123-72-8), which is a type of volatile straight-chain aldehyde.

[0027] In the antibacterial or antiviral agent of the present disclosure, one of the active ingredients is a branched aldehyde having a molecular weight of 150 or less. The branched aldehyde having a molecular weight of 150 or less is a volatile compound. The molecular weight of the branched aldehyde may be 150 or less, specifically, 72 to 150, preferably 72 to 120, and more preferably 85 to 110. Specific examples of branched-chain aldehydes having a molecular weight of 150 or less include 2-ethylbutanal (CAS 97-96-1), 2-methylbutanal (CAS 96-17-3), (E)-2-methyl-2-pentenal (CAS 14250-96-5), 2-methyl-2-pentenal (CAS 623-36-9), isovaleraldehyde (CAS 590-86-3), and melonal (CAS 106-72-9).

[0028] In the antibacterial or antiviral agent disclosed herein, one of the active ingredients is a cyclic aldehyde. Regarding the cyclic aldehyde, the aldehyde group may be directly bonded to the atoms constituting the cyclic structure, and the atoms constituting the cyclic structure may be bonded to the aldehyde group via one or more atoms. In addition, the cyclic structure in the cyclic aldehyde may be any of an alicyclic ring, a heterocyclic ring or an aromatic ring, and may also be any of a monocyclic ring or a polycyclic ring. The cyclic aldehyde used in the antibacterial or antiviral agent disclosed herein is preferably volatile. Specific examples of the volatile cyclic aldehydes include phenylacetaldehyde (CAS 122-78-1), furfural (CAS 98-01-1), benzaldehyde (CAS 100-52-7), triplal (CAS 68039-49-6), cinnamic aldehyde (CAS 104-55-2), anisaldehyde (CAS 123-11-5), 4-methylphenylacetaldehyde (CAS 104-09-6), 5-methylfurfural (CAS 620-02-2), 2-furancarboxaldehyde (CAS 64-11-6 ... 98-01-1), 2-pyrrolylcarbaldehyde (CAS1003-29-8), 3-thienylcarbaldehyde (CAS 498-62-4), p-tolualdehyde (CAS104-87-0), α-methylcinnamaldehyde (CAS122-40-7), etc.

[0029] In the antibacterial or antiviral agent disclosed herein, as an active ingredient, one can be selected from 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched chain aldehydes with a molecular weight of less than 150, and cyclic aldehydes and used alone, or two or more thereof can be used in combination.

[0030] Among these active ingredients, from the viewpoint of exerting a more excellent antibacterial or antiviral effect, preferred ones include: 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural, and more preferred ones include: 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, and (E,E)-2,4-hexadienal.

[0031] [Bacteria or viruses to be applied to] The antibacterial or antiviral agents of the present disclosure are capable of inhibiting the growth of a wide variety of bacteria or viruses.

[0032] There is no particular limitation on the type of bacteria to which the antibacterial or antiviral agent of the present invention is applied, and it can be any of Gram-positive bacteria or Gram-negative bacteria. Specifically, Gram-positive bacteria to which the antibacterial or antiviral agent of the present invention is applied include Staphylococcus aureus and other Staphylococci; Bacillus bacteria; Listeria bacteria; Alicyclobacillus bacteria, etc. In addition, Gram-negative bacteria to which the antibacterial or antiviral agent of the present invention is applied include Escherichia coli and other Escherichia bacteria; Klebsiella bacteria such as Klebsiella pneumoniae; Pseudomonas bacteria such as Pseudomonas aeruginosa; Salmonella bacteria; Vibrio bacteria; Acinetobacter bacteria, etc. Among these bacteria, Staphylococcus, Escherichia bacteria, and Klebsiella bacteria can be cited as preferred examples of the application objects of the antibacterial or antiviral agent of the present invention.

[0033] There is no particular limitation on the type of virus to which the antibacterial or antiviral agent of the present invention is applied, and it may be any of enveloped viruses or non-enveloped viruses. Specifically, as enveloped viruses to which the antibacterial or antiviral agent of the present invention is applied, influenza virus, coronavirus (HCoV-229E, HCoV-OC43, HCoV-NL63, HCoV-HKU1), new coronavirus (SARS-CoV-2), herpes virus, RS virus, etc. may be cited. In addition, as non-enveloped viruses to which the antibacterial or antiviral agent of the present invention is applied, feline calicivirus, norovirus, rotavirus, poliovirus, adenovirus, etc. may be cited. Among these viruses, influenza virus, feline calicivirus, and norovirus may be cited as preferred examples of the application objects of the antibacterial or antiviral agent of the present invention.

[0034] [Applicable objects, usage methods, etc.] The antibacterial or antiviral agent disclosed herein is used to impart an antibacterial or antiviral effect to an object by treating the object requiring antibacterial or antiviral effects. The object requiring antibacterial or antiviral effects includes not only spaces or articles where bacteria or viruses exist or are attached, but also spaces or articles where the attachment or proliferation of bacteria or viruses is required to be inhibited even if bacteria or viruses do not exist or are not attached.

[0035] Antibacterial or antiviral use of space By treating a space with the antibacterial or antiviral agent disclosed herein, an antibacterial or antiviral effect can be imparted not only to the space but also to the articles in the space. Articles in the space to which the antibacterial or antiviral effect is imparted include, for example, trash cans, sofas, chairs, tables, electrical appliances, sinks, toilets, bathtubs, washstands, curtains, carpets, bedding, clothes, shoes, leather products, storage furniture, wallpaper, doors, floors, windows, ceilings, and the like.

[0036] In order to treat a space using the antibacterial or antiviral agent disclosed herein, it is sufficient to volatilize or spray the antibacterial or antiviral agent disclosed herein in the space. When the antibacterial or antiviral agent disclosed herein is used for antibacterial or antiviral purposes in a space, the antibacterial or antiviral agent disclosed herein is mixed with a volatile solvent to prepare an antibacterial or antiviral composition for use in a space and provided.

[0037] The content of the antibacterial or antiviral agent of the present invention in the antibacterial or antiviral composition for use in space can be appropriately set according to the type, width, etc. of the space to be applied. For example, the amount of the compound can be 0.1% by weight to 99.9% by weight, preferably 1% by weight to 99.9% by weight, and more preferably 1% by weight to 80% by weight.

[0038] The solvent used in the antibacterial or antiviral composition for space use can be any solvent that can make the antibacterial or antiviral agent of the present invention soluble or dispersed and can evaporate at room temperature. Examples thereof include water, paraffins (light liquid isoparaffins, light liquid normal paraffins), 3-methoxy-3-methyl-1-butanol, propylene glycol monomethyl ether, etc. These solvents can be used alone or in combination of two or more. In the antibacterial or antiviral composition for space use, the content of the solvent can be the remainder other than the antibacterial or antiviral agent of the present invention and the additives added as needed.

[0039] In addition, in addition to the antibacterial or antiviral agent of the present invention, other additives may be included in the antibacterial or antiviral composition for use in space. Other additives that can be incorporated into the antibacterial or antiviral composition for use in space include, for example, surfactants, antioxidants, pH adjusters, fragrances, deodorants, disinfectants, ultraviolet absorbers, insecticides, insect repellents, repellents, gelling agents, and the like.

[0040] The shape of the antibacterial or antiviral composition for use in space is not particularly limited as long as the antibacterial or antiviral agent of the present invention can be volatilized or sprayed. For example, if it is allowed to volatilize by standing still, it can be in a liquid or gel state, and if it is allowed to spray, it can be in a liquid state.

[0041] In order to volatilize the antibacterial or antiviral composition for use in a space in the space, the antibacterial or antiviral composition for use in a space can be placed in the space in a volatilizable state in the same manner as the conventional stationary fragrance. In order to spray the antibacterial or antiviral composition for use in a space into the space, a spray container or an aerosol container can be used.

[0042] As the application object space of the antibacterial or antiviral composition for space, any space separated from the outdoors can be cited, for example: box spaces such as trash cans and shoe cabinets; indoor spaces such as living rooms, toilets, bathrooms, washrooms, entrances, closets; car interior spaces such as cars, buses, trucks, etc.; restaurants, factories, offices, meeting rooms, etc. The interior space of facilities. As a preferred example of a space for volatilizing the antibacterial or antiviral agent of the present invention, a trash can or a space where a trash can is set can be cited. Since trash cans are prone to breeding bacteria and also become the cause of bad odors, the bad odor can be prevented or removed by volatilizing the antibacterial or antiviral agent of the present invention in a trash can or a space where a trash can is set.

[0043] Antibacterial or antiviral use of articles By treating an article with the antibacterial or antiviral agent of the present disclosure, an antibacterial effect or an antiviral effect can be imparted to the article.

[0044] In order to treat an article with the antibacterial or antiviral agent of the present invention, the article can be coated or sprayed with the antibacterial or antiviral agent of the present invention. When the antibacterial or antiviral agent of the present invention is used for the antibacterial or antiviral purpose of an article, the antibacterial or antiviral agent of the present invention is mixed with a solvent to prepare an antibacterial or antiviral composition for the article.

[0045] The content of the antibacterial or antiviral agent of the present invention in the antibacterial or antiviral composition for articles can be appropriately set according to the space of application, the type of article, etc., and for example, the amount of the compound can be 0.1% by weight to 99.9% by weight, preferably 1% by weight to 99.9% by weight, and more preferably 1% by weight to 80% by weight.

[0046] As the solvent used in the antibacterial or antiviral composition for articles, any solvent can be used as long as it can make the antibacterial or antiviral agent of the present invention soluble or dispersible, for example, water, ethanol, propanol, etc. These solvents can be used alone or in combination of two or more. In the antibacterial or antiviral composition for articles, the content of the solvent can be the remaining part other than the antibacterial or antiviral agent of the present invention and the additives added as needed.

[0047] In addition, in addition to the antibacterial or antiviral agent of the present invention, other additives may be included in the antibacterial or antiviral composition for articles. Other additives that can be incorporated into the volatile antibacterial or antiviral composition include, for example, surfactants, antioxidants, pH adjusters, fragrances, deodorants, disinfectants, ultraviolet absorbers, insecticides, insect repellents, repellents, etc.

[0048] In order to facilitate coating or spraying on the article to be applied, the antibacterial or antiviral composition for articles can be impregnated with a fabric such as a nonwoven fabric and provided in the form of a wipe, or can be provided in the form of a spray or aerosol.

[0049] Examples of articles to which the antibacterial or antiviral composition can be applied include: fiber products such as cloth sofas, bedding, clothes, curtains, masks, diapers, wet wipes, carpets, etc.; hard surfaces such as toilets, bathtubs, washbasins, sinks, tiles, glass, etc.; architectural structures such as wallpaper, doors, handrails, floors, windows, ceilings, etc.; trash cans, chairs, tables, electrical appliances, storage furniture, shoe cabinets, shoes, leather products, etc.

[0050] A preferred example of an article to which the antibacterial or antiviral agent of the present disclosure is applied is a trash can. Since trash cans are prone to bacterial growth and cause bad odors, bad odors can be prevented or removed by treating trash cans with the antibacterial or antiviral agent of the present disclosure.

[0051] Moreover, as another preferable example of the article to which the antibacterial or antiviral agent of the present disclosure is applied, a fiber product can be mentioned.

[0052] In addition, as another preferred example of an article to which the antibacterial or antiviral agent of the present invention is applied, a hard surface, in particular a hard surface made of plastic, can be cited. As a preferred method for treating a hard surface with the antibacterial or antiviral agent of the present invention, propionaldehyde and / or butyraldehyde can be cited as the antibacterial or antiviral agent of the present invention.

[0053] Antibacterial or antiviral uses for the body The antibacterial or antiviral agent of the present disclosure can impart an antibacterial or antiviral effect to the skin by being applied to the skin, thereby making the skin hygienic.

[0054] When the antibacterial or antiviral agent of the present disclosure is applied to the skin, it may be provided as an antibacterial or antiviral composition for external use containing the antibacterial or antiviral agent of the present disclosure.

[0055] The content of the antibacterial or antiviral agent of the present disclosure in the antibacterial or antiviral external composition can be appropriately set according to the formulation form of the external composition, and for example, the amount of the compound can be 0.1% to 50% by weight, preferably 0.1% to 30% by weight, and more preferably 0.1% to 10% by weight.

[0056] The antibacterial or antiviral external composition can be formulated by combining additives and bases with the antibacterial or antiviral agent disclosed herein. As long as the antibacterial or antiviral external composition can be applied to the skin, it can be any formulation form of external skin medicines, cosmetics, skin cleansers, etc. As the formulation form of the antibacterial or antiviral external composition, specifically, it can be cited: external skin medicines such as creams, detergents, gels, emulsions, liquids, ointments, patches, liniments, aerosols, aqueous ointments, facial masks, hand gels, finger disinfectants, etc.; cosmetics such as aqueous ointments, creams, emulsions, lotions, detergents, facial masks, gels, etc.; skin cleansers such as shower gels, shampoos, rinses, and wet wipes for wiping, etc.

[0057] ・Applications for the purpose of improving storage quality or durability The antibacterial or antiviral agent of the present disclosure can function as a preservative by being added to a product requiring antibacterial or antiviral properties, and can also improve the shelf life or durability of the product.

[0058] The types of products requiring antibacterial or antiviral properties are not particularly limited, and examples thereof include foods, pharmaceuticals, cosmetics, fiber products, resin products, and paper products.

[0059] The content of the antibacterial or antiviral agent of the present disclosure in the product can be appropriately set according to the type of the product, and for example, the amount of the compound can be 0.1% to 50% by weight, preferably 0.1% to 30% by weight, and more preferably 0.1% to 10% by weight.

[0060] When the product is a food, medicine or cosmetic, the antibacterial or antiviral agent of the present invention can be used as an additive. In addition, when the product is a fiber product, a resin product or a paper product, the antibacterial or antiviral agent of the present invention can be added to the raw materials used in their manufacture. Example

[0061] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited to these examples.

[0062] Test Example 1: Evaluation of antibacterial activity against bacteria smeared on agar medium 1. Test materials and test methods In this test, volatile substances and test strains are placed in a closed space without contact, and the antibacterial effect exerted by the volatilization of the test sample is evaluated. The specific test materials and test methods are as follows.

[0063] (1) Test strains As test strains, Staphylococcus aureus (Staphylococcus aureus NBRC12732) and Escherichia coli (Escherichia coli NBRC3972) were prepared.

[0064] (2) Preparation of test bacterial solution The test strain cultured on SCD agar medium was scraped with a 10 μl disposable inoculation loop to collect a scraped loop of colonies, added to 10 mL of sterile saline and stirred thoroughly to prepare a test bacterial suspension. Next, the number of bacteria in the test bacterial suspension was measured by the colony forming unit (CFU) counting method (smear plate culture method), and the test bacterial suspension was diluted with sterile saline to prepare about 1.0×10 7 cfu / mL of the test bacterial solution.

[0065] (3) Preparation of test bacterial plates 0.1 mL of each test bacterial solution was applied to an SCD plate medium (a petri dish with a diameter of 9.0 cm and a height of 2.0 cm was used) to prepare a test bacterial plate. The test bacterial plate was prepared immediately before the antibacterial test described below.

[0066] (4) Assembly of test vessel The outer bottom of glass petri dish B (2.6 cm in diameter, 1.2 cm in height) was adhered and fixed to the center of the inner bottom of glass petri dish A (8.5 cm in diameter, 3.0 cm in height) with double-sided tape to prepare a test container.

[0067] (5) Preparation of test samples The original solution (100%) of each volatile substance shown in Tables 1 and 2, and the diluted solution obtained by diluting the solution with isoalkane to the concentration shown in Tables 1 and 2 were used as test samples.

[0068] (6) Antibacterial test 1 ml of the test sample was added to the glass culture dish B of the test container. Then, the test bacteria plate was placed in the test container in such a way that the inner bottom of the glass culture dish A of the test container and the inner bottom of the culture dish of the test bacteria plate (the SCD flat culture medium side coated with the test bacteria solution) were placed opposite each other, and the surrounding was wrapped and sealed with a sealing film in such a way that there was no gap at the interface between the test container and the test bacteria plate, thereby leaving the test sample and the test strain in a non-contact state in a closed space, and incubated at 37°C for 24 hours. In addition, as a control, incubation was carried out under the same conditions as above except that the test sample was not added to the glass culture dish B. After 24 hours, the proliferation degree of the test strain in the test bacteria plate was visually confirmed, and the antibacterial effect was evaluated according to the following judgment criteria. <Criteria for judging antibacterial effects> A: No colonies were formed on the test plate, and the proliferation of bacteria was completely inhibited. B: Although colony formation was observed on the test bacterial plate, the colony formation was significantly suppressed compared with the control, and the bacterial growth inhibition effect was confirmed. C: Colonies were observed throughout the test plate, and the number of colonies formed was comparable to that of the control, and bacterial growth was not inhibited.

[0069] 2. Test results The results are shown in Tables 1 and 2. In the case of the volatile substances of Comparative Examples 1 to 12, no antibacterial effect was confirmed against Staphylococcus aureus and Escherichia coli, whereas 2-cyclohexene-1-one, α-angelica lactone, propionaldehyde, butyraldehyde, 2-cyclopentene-1-one, branched chain aldehydes with a molecular weight of 150 or less, cyclic aldehydes, or (E,E)-2,4-hexadienal were able to exhibit excellent antibacterial effects against Staphylococcus aureus and Escherichia coli by volatilization (Examples 1 to 12).

[0070] [Table 1] The original Japanese text of “1-(2-furanyl)-ethanone” is “1-(2-furanyl)-ethanone”. In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out.

[0071] [Table 2] In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out.

[0072] Test Example 2: Evaluation of antibacterial effect on fiber surface 1. Test materials and test methods In this test, after the fiber sheet is left to stand in an environment where volatile substances are volatilized, the fiber sheet is left to stand in contact with the test strain to evaluate the antibacterial effect of the fiber sheet. Specific test materials and test methods are as follows.

[0073] (1) Test strains As test strains, Klebsiella pneumoniae (NBRC13277) and Staphylococcus aureus (NBRC12732) were prepared.

[0074] (2) Preparation of test bacterial solution Take 1 platinum inoculation loop of the test strain cultured on SCD agar medium, suspend it in 20 mL NB liquid medium, and shake culture at 37°C for 18 to 24 hours. Take 0.4 mL of the shaking culture solution and culture solution, suspend it in 20 mL NB liquid medium, and shake culture at 37°C for 2 to 4 hours. Then, measure the number of bacteria in the culture solution by the colony forming unit (CFU) counting method (smear plate culture method), dilute the culture solution with 1 / 20 NB liquid medium, and prepare 1.0 to 3.0 × 10 5 cfu / mL of the test bacterial solution.

[0075] (3) Preparation of test samples The original solution (100%) of each volatile substance shown in Table 3 and the diluted solution obtained by diluting the original solution with isoalkane to the concentration shown in Table 3 were used as test samples.

[0076] (4) Preparation of treated and untreated fibers of test samples At the inner bottom of glass culture dish A (8.5cm in diameter, 3.0cm in height), 0.4g of cut cotton cloth (2cm×2cm square) and glass culture dish B (2.6cm in diameter, 1.2cm in height) were placed side by side, 0.5mL of test sample was added to the inside of glass culture dish B, and glass culture dish A was covered, so that the test sample and cotton cloth were in a non-contact state in a confined space. In this state, the test sample was allowed to stand at room temperature for 30 minutes to obtain the test sample treated fiber. The test sample treated fiber was made before the antibacterial test described later was about to be carried out. In addition, 0.4g of cotton cloth (2cm×2cm square) not subjected to the above treatment was prepared as untreated treated fiber.

[0077] (5) Antibacterial test Place the test sample treated fiber or untreated fiber in a vial, further inoculate 200 μL of the test bacterial solution evenly on the entire test sample treated fiber or untreated fiber, close the lid of the vial, and let it stand at 37°C for 24 hours. Next, add 20 mL of SCDLP liquid culture medium to the vial, stir it thoroughly, and disperse the bacteria in the SCDLP liquid culture medium to obtain a bacterial dispersion. Then, the number of bacteria in the bacterial dispersion is measured by the colony forming unit (CFU) counting method (smear plate culture method), and the antibacterial activity value is calculated according to the following formula. [Number 1] Antimicrobial activity value = Log 10 (Bacteria count when using untreated fiber) - Log 10 (Bacteria count when fiber is treated with test sample)

[0078] Based on the numerical value of the antimicrobial activity value, the antimicrobial effect was evaluated according to the following criteria. <Criteria for judging antibacterial effects> A: Antibacterial activity value is 3.0 or above (has high antibacterial effect) B: Antibacterial activity value is 2.0 or more and less than 3.0 (has antibacterial effect) C: Antibacterial activity value is less than 2.0 (no antibacterial effect)

[0079] 2. Test results The results are shown in Table 3. The fibers left in a space where the volatile substances of Comparative Examples 1 to 12 were volatilized had no antibacterial effect on Streptococcus pneumoniae and Staphylococcus aureus. In contrast, the fibers left in a space where 2-cyclohexene-1-one, α-angelica lactone, propionaldehyde, butyraldehyde, 2-cyclopentene-1-one, branched chain aldehydes with a molecular weight of 150 or less, cyclic aldehydes, or (E,E)-2,4-hexadienal were volatilized had excellent antibacterial effects on Streptococcus pneumoniae and Staphylococcus aureus (Examples 1 to 12).

[0080] [Table 3] In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out. The "*" in the table refers to the results obtained under the condition that the time for which the test sample and the cotton cloth were kept in a non-contact state in a closed space was changed to 3 hours when preparing the test sample treated fibers.

[0081] Test Example 3: Evaluation of antibacterial effect on hard surfaces (1) 1. Test materials and test methods In this test, a polyvinyl chloride plate is left to stand in an environment where volatile substances are volatilized, and then the plate is left to stand in contact with a test strain to evaluate the antibacterial effect of the plate. Specific test materials and test methods are as follows.

[0082] (1) Test strains As test strains, Escherichia coli NBRC3972 and Staphylococcus aureus NBRC12732 were prepared.

[0083] (2) Preparation of test bacterial solution Take one platinum loop of the test strain cultured on SCD agar medium at 34°C to 36°C for 16 to 24 hours, dilute the culture solution with 1 / 500 NB liquid medium, and prepare 2.5 to 10×10 5 cfu / mL of the test bacterial solution.

[0084] (3) Preparation of test samples The original solution (100%) of each volatile substance shown in Table 4 and the diluted solution obtained by diluting the original solution with isoalkane to the concentration shown in Table 4 were used as test samples.

[0085] (4) Preparation of test sample treated and untreated plates At the inner bottom of glass culture dish A (8.5cm in diameter, 3.0cm in height), a cut polyvinyl chloride plate (4.8cm×4.8cm square) and glass culture dish B (2.6cm in diameter, 1.2cm in height) are placed side by side, 0.5mL of test sample is added to the inside of glass culture dish B, and glass culture dish A is covered, so that the test sample and cotton cloth are in a non-contact state in a closed space. In this state, it is allowed to stand at room temperature for 30 minutes to obtain a test sample treatment plate. The test sample treatment plate is made before the antibacterial test described later is about to be carried out. In addition, a polyvinyl chloride plate (4.8cm×4.8cm square) that has not been treated as described above is prepared as an untreated treatment plate.

[0086] (5) Antibacterial test 400 μL of the test bacterial solution was inoculated uniformly on the entire surface of the test sample treated plate or the untreated plate, covered with a sealing film (4 cm × 4 cm square), and left to stand at 35 ° C and relative humidity above 90% RH for 24 hours. Then, the test sample treated plate or the untreated plate was transferred to a vinyl bag covered with a sealing film, 10 mL of SCDLP liquid culture medium was added, and the outside of the vinyl bag was fully rubbed manually to disperse the bacteria in the SCDLP liquid culture medium to obtain a bacterial dispersion. Then, the number of bacteria in the bacterial dispersion was measured by the colony forming unit (CFU) counting method (smear plate culture method), and the antibacterial activity value was calculated according to the following formula. [Number 2] Antimicrobial activity value = Log 10 (Bacterial count when using untreated plates) - Log 10 (Bacterial count when using a test sample treatment plate)

[0087] Based on the numerical value of the antimicrobial activity value, the antimicrobial effect was evaluated according to the following criteria. <Criteria for judging antibacterial effects> A: Antibacterial activity value is 3.0 or above (has high antibacterial effect) B: Antibacterial activity value is 2.0 or more and less than 3.0 (has antibacterial effect) C: Antibacterial activity value is less than 2.0 (no antibacterial effect)

[0088] 2. Test results The results are shown in Table 4. The polyvinyl chloride plates that were placed in a space where the volatile substances of Comparative Examples 3 to 5 were volatilized did not show an antibacterial effect on Escherichia coli or Staphylococcus aureus. In contrast, the polyvinyl chloride plates that were placed in a space where 2-methyl-2-pentenal was volatilized were able to exert an excellent antibacterial effect on Escherichia coli (Example 9). In addition, the polyvinyl chloride plates that were placed in a space where propionaldehyde, butyraldehyde, and 2-methyl-2-pentenal were volatilized were able to exert an excellent antibacterial effect on Staphylococcus aureus (Examples 3, 4, and Example 9).

[0089] [Table 4] In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out.

[0090] Test Example 4: Evaluation of antibacterial effect on hard surfaces (2) 1. Test materials and test methods In this test, after the polyurethane plate is left to stand in an environment where volatile substances are volatilized, the plate is left to stand in contact with the test strain to evaluate the antibacterial effect of the plate. The test materials and test methods are the same as those in the above-mentioned Test Example 3 except that a polyurethane plate (4.8 cm×4.8 cm square) is used instead of a polyvinyl chloride plate.

[0091] 2. Test results The results are shown in Table 5. The polyurethane plates standing in a space where the volatile substances of Comparative Examples 3 to 5 are volatilized have no antibacterial effect on Escherichia coli or Staphylococcus aureus. In contrast, the polyurethane plates standing in a space where 2-cyclohexene-1-one, propionaldehyde, butyraldehyde, 2-cyclopentene-1-one, branched chain aldehydes with a molecular weight of 150 or less, or (E,E)-2,4-hexadienal are volatilized can exert an excellent antibacterial effect on Escherichia coli (Example 1, Examples 3 to 8, and Example 12). In addition, the polyurethane plates standing in a space where 2-cyclohexene-1-one, α-angelica lactone, propionaldehyde, butyraldehyde, branched chain aldehydes with a molecular weight of 150 or less, or (E,E)-2,4-hexadienal are volatilized can exert an excellent antibacterial effect on Staphylococcus aureus (Examples 1 to 4, Examples 6 to 8, and Example 12).

[0092] [Table 5] In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out. The "*" in the table are the results obtained under the condition that the time for which the test sample and the polyurethane plate were kept in a non-contact state in the closed space was changed to 3 hours when the test sample treated plate was prepared.

[0093] Test Example 5: Evaluation of antiviral effect on fiber surface 1. Test materials and test methods In this test, after the fiber sheet is left to stand in an environment where volatile substances are volatilized, the fiber sheet is left to stand in contact with a test virus to evaluate the antiviral effect of the fiber sheet. Specific test materials and test methods are as follows.

[0094] (1) Test virus As test strains, influenza virus (influenza A virus (H1N1); virus strain: ATCC VR-1469, host cell: MDCK (NBL-2) cells) and feline calicivirus (Feline calicivirus; virus strain: ATCC VR-782, host cell: CRFK cells) were prepared.

[0095] (2) Preparation of test virus solution The prepared host cells were inoculated with a test strain solution diluted with EMEM (-), cultured overnight at 37°C in the presence of 5% CO2, and then the supernatant separated by centrifugation was recovered to prepare 1.0×10 7 pfu / mL~1.0×10 8 Next, the obtained virus suspension was diluted 10 times with sterile purified water to prepare a test virus solution.

[0096] (3) Preparation of test samples The original solution (100%) of each volatile substance shown in Table 6 and the diluted solution obtained by diluting the original solution with isoalkane to the concentration shown in Table 6 were used as test samples.

[0097] (4) Preparation of treated and untreated fibers of test samples At the inner bottom of glass culture dish A (8.5cm in diameter, 3.0cm in height), 0.4g of cut cotton cloth (2cm×2cm square) and glass culture dish B (2.6cm in diameter, 1.2cm in height) were placed side by side, 0.5mL of test sample was added to the inside of glass culture dish B, and glass culture dish A was covered, so that the test sample and cotton cloth were in a non-contact state in a confined space. In this state, the test sample was allowed to stand at room temperature for 30 minutes to obtain the test sample treated fiber. The test sample treated fiber was made before the antibacterial test described later was about to be carried out. In addition, 0.4g of cotton cloth (2cm×2cm square) not subjected to the above treatment was prepared as untreated treated fiber.

[0098] (5) Antiviral test Place the test sample treated fiber or untreated fiber in a vial, further inoculate 200 μL of the test virus liquid evenly on the entire test sample treated fiber or untreated fiber, close the lid of the vial, and let it stand at 25°C for 18 hours. Next, add 20 mL of SCDLP liquid culture medium to the vial, stir it thoroughly, and disperse the bacteria in the SCDLP liquid culture medium to obtain a virus dispersion. Then, add 0.1 mL of the virus dispersion to 0.9 mL of EMEM (-), measure the number of plaques by plaque assay, and calculate the antiviral activity value according to the following formula. [Number 3] Antimicrobial activity value = Log 10 (Number of viruses when using untreated fiber) - Log 10 (Number of viruses when fiber is treated with test sample)

[0099] Based on the numerical value of the antiviral activity value, the antibacterial effect was evaluated according to the following criteria. <Criteria for judging antiviral effects> A: Antiviral activity value is 3.0 or above (high antiviral effect) B: Antiviral activity value is 2.0 or more and less than 3.0 (has antiviral effect) C: Antiviral activity value is less than 2.0 (no antiviral effect)

[0100] 2. Test results The results are shown in Table 6. The fiber sheets left in a space where the volatile substances of Comparative Examples 3 to 5 were volatilized did not show antiviral effects on influenza virus and feline calicivirus. In contrast, the fiber sheets left in a space where 2-cyclohexene-1-one, α-angelica lactone, propionaldehyde, butyraldehyde, 2-cyclopentene-1-one, branched chain aldehydes with a molecular weight of 150 or less, cyclic aldehydes, or (E,E)-2,4-hexadienal were volatilized were able to exhibit excellent antibacterial effects on influenza virus (Examples 1 to 12). In addition, the fiber sheets placed in a space where 2-cyclohexene-1-one, α-angelica lactone, propionaldehyde, 2-cyclopentene-1-one, 2-ethylbutyraldehyde, (E)-2-methyl-2-pentenal, cyclic aldehydes, or (E,E)-2,4-hexadienal are volatilized can exert excellent antibacterial effects on feline calicivirus (Examples 1 to 3, Example 5, Example 6, Example 8, and Examples 10 to 12).

[0101] [Table 6] In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out. The "*" in the table refers to the results obtained under the condition that the time for which the test sample and the cotton cloth were kept in a non-contact state in a closed space was changed to 3 hours when preparing the test sample treated fibers.

[0102] Test Example 6: Evaluation of antiviral effect on hard surfaces 1. Test materials and test methods In this test, after the polyurethane plate is left standing in an environment where volatile substances are volatilized, the plate is left standing in contact with the test virus to evaluate the antiviral effect of the plate. The test materials and test methods are the same as those in the above-mentioned Test Example 5, except that a polyurethane plate (4.8 cm × 4.8 cm square) is used instead of the fiber sheet and the amount of the test virus solution placed in the vial is changed to 400 μL.

[0103] 2. Test results The results are shown in Table 7. The polyurethane plates standing in a space where the volatile substances of Comparative Examples 3 to 5 are volatilized have no confirmed antiviral effect on influenza virus and feline calicivirus. In contrast, the polyurethane plates standing in a space where α-angelica lactone, propionaldehyde, butyraldehyde, branched aldehydes with a molecular weight of less than 150, or (E,E)-2,4-hexadienal are volatilized can exert excellent antibacterial effects on influenza virus (Examples 2 to 4, Examples 6 to 9, and Example 12). Moreover, the polyurethane plates standing in a space where propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, or (E,E)-2,4-hexadienal are volatilized can exert excellent antibacterial effects on feline calicivirus (Example 3, Example 4, Examples 6 to 8, and Example 12).

[0104] [Table 7] In the table, the volatile substances indicated as "(10% DPG)" were used in a state diluted to 10% with dipropylene glycol as a stock solution (100%). In the table, “—” means the test was not carried out. The "*" in the table are the results obtained under the condition that the time for which the test sample and the polyurethane plate were kept in a non-contact state in the closed space was changed to 3 hours when the test sample treated plate was prepared.

Claims

1. An antibacterial or antiviral agent, characterized in that The compound comprises at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched chain aldehydes having a molecular weight of 150 or less, and cyclic aldehydes.

2. The antibacterial or antiviral agent according to claim 1, wherein The compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural.

3. An antibacterial or antiviral composition for use in space, characterized in that: Contains the antibacterial or antiviral agent according to claim 1 or 2 and a solvent.

4. An antibacterial or antiviral composition for articles, characterized in that: Contains the antibacterial or antiviral agent according to claim 1 or 2 and a solvent.

5. The antibacterial or antiviral composition for articles according to claim 4, wherein: The article is a fiber product.

6. A compound for use as an antibacterial or antiviral agent in spaces or articles, wherein the compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes with a molecular weight of less than 150, and cyclic aldehydes.

7. The use according to claim 6, wherein The compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural.

8. A composition for use as an antibacterial or antiviral composition for use in space, the composition comprising at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes with a molecular weight of less than 150, and cyclic aldehydes, and a solvent.

9. Use of a composition as an antibacterial or antiviral composition for an article, the composition comprising at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched-chain aldehydes having a molecular weight of 150 or less, and cyclic aldehydes, and a solvent.

10. The use according to claim 9, wherein The article is a fiber product.

11. An antibacterial or antiviral method, characterized in that: An object requiring antibacterial or antiviral properties is treated using at least one compound selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, branched chain aldehydes having a molecular weight of 150 or less, and cyclic aldehydes.

12. The method according to claim 11, wherein: The compound is at least one selected from the group consisting of 2-cyclohexene-1-one, α-angelica lactone, 2-cyclopentene-1-one, (E,E)-2,4-hexadienal, propionaldehyde, butyraldehyde, 2-ethylbutyraldehyde, 2-methylbutyraldehyde, (E)-2-methyl-2-pentenal, 2-methyl-2-pentenal, phenylacetaldehyde, and furfural.

13. The method according to claim 11 or 12, wherein: The object that requires antibacterial or antiviral is space. The space is treated with the compound.

14. The method according to claim 11 or 12, wherein: The object to be antibacterial or antiviral is an article. The article is treated with the compound.

15. The method according to claim 14, wherein: The article is a fiber product.

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