Antiviral agent

Abstract

To provide an antiviral agent having excellent antiviral performance.SOLUTION: An antiviral agent contains: a compound represented by formula (I), Zn(CnH2n-1O2)2, where n represents an integer from 6 to 10; and a compound represented by formula (II) in the figure, where R1 represents a linear or branched hydrocarbon having 8 to 18 carbon atoms, and R2 represents hydrogen or a linear or branched hydrocarbon having 8 to 18 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an antiviral agent. [Background technology]

[0002] Viruses such as influenza virus and norovirus cause various diseases, and therefore, for example, Patent Document 1 proposes antiviral agents. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication WO2021 / 200808 Summary of the Invention [Problem to be solved by the invention]

[0004] This antiviral agent is usually blended with resin and processed into antiviral finished products, but depending on the type of resin used in the finished product, the antiviral effect may not be fully realized. Therefore, there has been a demand for an antiviral agent that can demonstrate excellent antiviral performance regardless of the type of resin used in the finished product. [Means for solving the problem]

[0005] The present inventors have conducted extensive research to solve the above problems and have arrived at the present invention. (1) An antiviral agent containing a compound represented by formula (I) and a compound represented by formula (II). Zn(C n H 2n-1 O2)2(I) (n represents an integer between 6 and 10.) TIFF2025154153000001.tif2758 (R1 represents a straight-chain or branched hydrocarbon having 8 to 18 carbon atoms, and R2 represents hydrogen or a straight-chain or branched hydrocarbon having 8 to 18 carbon atoms.) (2) The above antiviral agent containing zinc octylate as the compound of formula (I). (3) The above antiviral agent containing monolauryl phosphate as the compound of formula (II). (4) The antiviral agent as described above, wherein the weight ratio of the compounds represented by formula (I) and formula (II) is in the range of 7:3 to 3:7. (5) The antiviral agent as described above, wherein the target virus is influenza virus and / or norovirus. (6) An antiviral preparation comprising the above antiviral agent and an oil-absorbing powder. (7) An antiviral processed product containing the above antiviral preparation. to provide. [Effects of the Invention]

[0006] According to the present invention, it is possible to provide an antiviral agent that exhibits excellent antiviral performance regardless of the type of resin in the antiviral processed product. BEST MODE FOR CARRYING OUT THE INVENTION

[0007] The antiviral agent of the present invention includes a compound represented by general formula (I). Zn(C n H 2n-1 O2)2(I) (n represents an integer between 6 and 10.) The compound may have any of a linear, branched, or cyclic structure. Specific examples include one or more compounds selected from the group consisting of zinc octoate, zinc 2-ethylhexanoate, and zinc versatate. Of these, zinc octoate and zinc 2-ethylhexanoate are preferred.

[0008] The antiviral agent of the present invention includes a compound represented by general formula (II). TIFF2025154153000002.tif2758 (R1 represents a straight-chain or branched hydrocarbon having 8 to 18 carbon atoms, and R2 represents hydrogen or a straight-chain or branched hydrocarbon having 8 to 18 carbon atoms.) The compound is a compound called a monoalkyl phosphate or a dialkyl phosphate, and the alkyl group may have either a linear or branched structure. Specific examples include one or more selected from the group consisting of monooctyl phosphate, mono-2-ethylhexyl phosphate, monodecyl phosphate, monolauryl phosphate, monomyristyl phosphate, monopalmityl phosphate, monostearyl phosphate, dioctyl phosphate, di-2-ethylhexyl phosphate, didecyl phosphate, dilauryl phosphate, dimyristyl phosphate, dipalmityl phosphate, and distearyl phosphate. Among these, monolauryl phosphate is preferred.

[0009] The antiviral agent of the present invention is prepared by adjusting the weight ratio of the compound represented by general formula (I) to the compound represented by general formula (II) to be preferably in the range of 5:95 to 95:5, more preferably in the range of 80:20 to 30:70, and even more preferably in the range of 70:30 to 30:70.

[0010] The antiviral agent of the present invention is typically used after being mixed with an oil-absorbing powder to form a powder formulation. The particle size of the powder is preferably in the range of 0.1 μm to 50 μm, more preferably 0.5 to 5 μm, as an average particle size on a volume basis. Examples of such powder include calcium silicate and silicon dioxide. Specific examples of such powder include Fluorite® R and Fluorite® RT (manufactured by Tomita Pharmaceutical Co., Ltd.), Toxil® NR (manufactured by Oriental Silicas Corporation), and Sunsphere® H-33 (manufactured by AGC Si-Tech Co., Ltd.). The oil-absorbing powder referred to here refers to a powder having an oil absorption of 1.5 to 5 mL / g, as measured according to JIS K5101-13-1.

[0011] Solvents can be used in the formulation, and examples of such solvents include monohydric alcohols such as ethanol, isopropanol, phenoxyethanol, and benzyl alcohol; glycol solvents such as ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, and butylene glycol; glycol ether solvents such as diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, and tripropylene glycol monomethyl ether; glycerin-based solvents such as glycerin and diglycerin; cyclic organic solvents such as N-methylpyrrolidone, N-ethylpyrrolidone, and γ-butyrolactone; sulfur-based solvents such as dimethyl sulfoxide; ester-based solvents such as phthalates, adipates, and sebacates; aromatic solvents such as methylnaphthalene, phenylxylylethane, and alkylbenzenes; aliphatic hydrocarbon solvents such as normal paraffin and isoparaffin; rapeseed oil, cottonseed oil, soybean oil, castor oil, turpene, and mineral spirits. These solvents may be used alone or in combination of two or more.

[0012] When preparing the formulation, surfactants, pH adjusters, antifoaming agents, rust inhibitors, viscosity adjusters, sequestering agents, light stabilizers, ultraviolet absorbers, antibacterial agents, etc. may be further added, either alone or in combination of two or more.

[0013] Examples of surfactants include nonionic surfactants such as polyoxyalkylene alkyl ethers, polyoxyalkylene allyl phenyl ethers, block copolymers of polyoxyethylene and polyoxypropylene, glycerin fatty acid esters, sorbitan fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, and polyoxyalkylene hydrogenated castor oil; anionic surfactants such as alkyl sulfate salts, alkyl ether sulfate salts, dialkyl sulfosuccinate salts, alkyl sulfonate salts, alkyl aryl sulfonate salts, fatty acid amide sulfonate salts, lignin sulfonate salts, alkyl naphthalene sulfonate salts, alkyl phosphate salts, alkyl ether phosphate salts, and naphthalene sulfonate formaldehyde condensate salts; cationic surfactants such as alkylamine salts and alkylammonium salts; and amphoteric surfactants such as glycine, betaine, and imidazoline types.

[0014] The antiviral agent or antiviral formulation of the present invention can be incorporated into substrates such as resin compounds, plastics such as films or sheets, coatings such as paints and surface treatment agents, adhesives, fibers such as woven fabrics and nonwoven fabrics, and paper, and can be used as antiviral processed products. According to the present invention, it can also be suitably used in processed products whose base material is polyethylene resin or polypropylene resin, for which the compound represented by general formula (I) alone is unlikely to exhibit antiviral effects. When the antiviral agent of the present invention is incorporated into an antiviral processed product, the amount of the antiviral agent incorporated is preferably 0.01 to 20 parts by weight per 100 parts of the base material of the antiviral processed product, and more preferably 0.1 to 10 parts by weight per 100 parts of the base material of the antiviral processed product.

[0015] By using the antiviral processed product of the present invention, it is possible to impart antiviral properties to components related to living environments such as wall materials, handrails, floor materials, wooden floor materials, kitchen counters, furniture, and wallpaper; textile products such as housings and filters for refrigerators and air conditioners; components related to electrical products such as protective films for image displays of portable electronic devices; components related to industrial products such as seats and floor mats for automobiles and trains; and components related to packaging such as wrapping paper and cardboard.

[0016] Antiviral performance means that even if a virus adheres to the surface, the viral infectivity is reduced, thereby reducing the infectivity.

[0017] The antiviral agent of the present invention is effective against influenza viruses and noroviruses, and is particularly effective against influenza viruses. The antiviral agent of the present invention is also expected to be useful in controlling viruses such as coronaviruses, rhinoviruses, respiratory syncytial viruses, adenoviruses, and enteroviruses. [Example]

[0018] The present invention will be specifically explained below with reference to examples, but the present invention is not limited to these examples.

[0019] Unless otherwise specified, all parts are by weight and all percentages are by weight.

[0020] Example 1 60 parts of dodecyl phosphate (manufactured by Fujifilm Wako Chemical Co., Ltd.; the rest is omitted) was heated to 50°C and then mixed with 26 parts of zinc 2-ethylhexanoate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.; zinc octoate purity 99%; the rest is omitted) to obtain the antiviral agent of the present invention (zinc octoate content: 25.7%, monolauryl phosphate content: 60%, zinc octoate:monolauryl phosphate=3:7). Furthermore, this antiviral agent was mixed with 14 parts of Fluorite R (calcium silicate, average particle size 35 μm, manufactured by Tomita Pharmaceutical Co., Ltd., the rest omitted) to obtain an antiviral preparation of the present invention.

[0021] Example 2 38 parts of dodecyl phosphate was heated to 50°C and mixed with 48 parts of zinc 2-ethylhexanoate to obtain the antiviral agent of the present invention (zinc octoate content: 47.5%, monolauryl phosphate content: 38%, zinc octoate:monolauryl phosphate = 5.6:4.4). This antiviral agent was mixed with 14 parts of Fluorite R to obtain the antiviral preparation of the present invention.

[0022] Example 3 21 parts of dodecyl phosphate was heated to 50°C and mixed with 48 parts of zinc 2-ethylhexanoate to obtain the antiviral agent of the present invention (zinc octoate content: 48.5%, monolauryl phosphate content: 24%, zinc octoate:monolauryl phosphate = 6.7:3.3). This antiviral agent was mixed with 31 parts of Fluorite R to obtain the antiviral agent.

[0023] Example 4 28 parts of dodecyl phosphate was heated to 50°C and mixed with 45 parts of zinc 2-ethylhexanoate to obtain the antiviral agent of the present invention (zinc octoate content: 44.6%, dodecyl phosphate content: 28%, zinc octoate:dodecyl phosphate=6.1:3.9). This antiviral agent was mixed with 27 parts of Sunsphere H-33 (AGC Si-Tech Co., Ltd., silicic anhydride, average particle size 3.7 μm) to obtain the antiviral formulation of the present invention.

[0024] Example 5 33 parts of ADK STAB AX-71 (ADEKA CORPORATION, a mixture of monostearyl phosphate and distearyl phosphate) was heated to 80°C and mixed with 53.6 parts of zinc 2-ethylhexanoate to obtain an antiviral agent of the present invention (zinc octoate content: 53.1%, mixture of mono- and distearyl phosphates: 33%, zinc octoate:mixture of monostearyl phosphate and distearyl phosphate=6.2:3.8). This antiviral agent was mixed with 13.4 parts of Fluorite R to obtain an antiviral formulation of the present invention.

[0025] Comparative Example 1 An antiviral preparation was obtained by mixing 80 parts of zinc 2-ethylhexanoate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., zinc octylate purity 99%) with 20 parts of Fluorite R (zinc octylate content: 79.2%).

[0026] Comparative Example 2 70 parts of dodecyl phosphate (manufactured by Fujifilm Wako Chemical Co., Ltd.) was heated to 50°C to melt, and mixed with 30 parts of Fluorite R to obtain an antiviral preparation.

[0027] Comparative Example 3 49 parts of zinc 2-ethylhexanoate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., zinc octoate purity 99%) and 39 parts of Phosphanol (registered trademark) LP-700 (manufactured by Toho Chemical Industry Co., Ltd., polyoxyethylene phenyl ether phosphate) were mixed, and then further mixed with 12 parts of Fluorite R to obtain an antiviral preparation (zinc octoate content: 48.5%, polyoxyethylene phenyl ether phosphate content: 39%).

[0028] [Preparation of polyethylene sheet] 34 parts of SUMIKATHENE (registered trademark) FV405 (polyethylene, manufactured by Sumitomo Chemical Co., Ltd.) was melted at 140°C using a Laboplastomill, to which 1.36 parts of each of the antiviral preparations from the Examples and Comparative Examples (4% by weight as antiviral agent concentration) was added and kneaded for 5 minutes. The mixture was then pressed for 3 minutes in a press molding machine heated to 170°C and cooled to obtain a polyethylene sheet. A blank sample was prepared by melting, pressing, and cooling under the same conditions without adding the antiviral agent, and this was used as the standard for evaluating the antiviral activity value.

[0029] [Antiviral test of polyethylene sheets] Antiviral testing of each sheet was performed in accordance with ISO 21702. First, the aforementioned polyethylene sheet samples were cut into 50 mm x 50 mm pieces to obtain test pieces. The test pieces were placed in plastic petri dishes, and 0.4 mL of the test influenza virus suspension was dropped onto the approximate center of each test piece. A 40 mm x 40 mm polyethylene film was placed over the test piece to cover the entire virus suspension, and the test piece was stored at 25°C and 95% humidity for 24 hours. The test influenza virus suspension sandwiched between the test piece and the polyethylene film was then washed out with SCDLP medium. A dilution series of this washed-out solution was prepared using the serial dilution method with E-MEM medium. The influenza virus infectivity of the resulting diluted solutions was measured using plaque assay on MDCK cells. The antiviral activity value was calculated by subtracting the logarithm of the infectivity value of the drug-added sample from the logarithm of the infectivity value of the blank sample.

[0030] In the antiviral test for each sheet described above, the test virus was changed from influenza virus to feline calicivirus, and the feline calicivirus infectivity titer was measured by the plaque assay method using CRFK cells. As above, the antiviral activity value was calculated by subtracting the logarithm of the infectivity titer of the drug-added sample from the logarithm of the infectivity titer of the blank sample. The measurement results for the polyethylene sheet samples are shown in Table 1.

[0031] [Table 1] TIFF2025154153000003.tif4072 [Industrial Applicability]

[0032] Because the antiviral agent of the present invention has excellent antiviral properties, it is possible to impart antiviral performance to members related to living environments such as wall materials, handrails, floor materials, wooden floor materials, kitchen counters, furniture, and wallpaper by using antiviral processed products containing the antiviral agent.

Claims

1. An antiviral agent comprising a compound represented by formula (I) and a compound represented by formula (II). Zn(C ｎ H ２ｎ－１ O ２ ) ２ (I) (n represents an integer of 6 to 10.) (R1 represents a straight or branched chain hydrocarbon having 8 to 18 carbon atoms, and R2 represents hydrogen or a straight or branched chain hydrocarbon having 8 to 18 carbon atoms.)

2. 2. The antiviral agent according to claim 1, wherein the compound represented by formula (I) is zinc octoate.

3. 2. The antiviral agent according to claim 1, wherein the compound represented by formula (II) is monolauryl phosphate.

4. 2. The antiviral agent according to claim 1, wherein the weight ratio of the compound represented by formula (I) to the compound represented by formula (II) is in the range of 7:3 to 3:

7.

5. The antiviral agent according to any one of claims 1 to 3, wherein the virus to be controlled is an influenza virus and / or a norovirus.

6. An antiviral preparation comprising the antiviral agent according to any one of claims 1 to 3 and a powder having oil-absorbing properties.

7. An antiviral processed product containing the antiviral preparation according to claim 6.

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