WO2023167055A1 - Antiviral agent - Google Patents
Antiviral agent Download PDFInfo
- Publication number
- WO2023167055A1 WO2023167055A1 PCT/JP2023/006177 JP2023006177W WO2023167055A1 WO 2023167055 A1 WO2023167055 A1 WO 2023167055A1 JP 2023006177 W JP2023006177 W JP 2023006177W WO 2023167055 A1 WO2023167055 A1 WO 2023167055A1
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- WIPO (PCT)
- Prior art keywords
- resin
- composition
- iminoctadine
- present
- antiviral
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
- C08K5/31—Guanidine; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present invention relates to antiviral agent compositions. More specifically, the present invention relates to an antiviral agent composition with excellent antiviral properties and uses thereof.
- This application claims priority to Japanese Patent Application No. 2022-32673 filed on March 3, 2022, the contents of which are incorporated herein.
- Viruses that adversely affect humans, animals or plants e.g. coronaviruses (SARS-CoV, SARS-CoV-2, MERS-CoV, HCoV-229E, HCoV-OC43, HCoV-NL63, HCoV-HKU1, etc.), type B Hepatitis virus, hepatitis C virus, hepatitis E virus, rabies virus, Ebola virus, AIDS virus, norovirus, poliovirus, rotavirus, Lassa fever virus, AIDS virus, West Nile virus, dengue fever virus, Japanese encephalitis virus, bird flu
- antiviral agents for preventing infection with viruses, human influenza virus, smallpox virus, herpes virus, and the like.
- US Pat. No. 5,900,000 discloses an anti-infective agent containing polyhexamethylene biguanide with an average molecular weight of 2,900-15,000.
- Patent Document 2 discloses a potash characterized by containing 0.05 to 0.5 wt% of a polyhexamethylene guanidine compound and 40 to 95 wt% of a lower alcohol or a mixture thereof, and having a pH in the range of 6 to 9. Compositions with virus-inactivating effects are disclosed.
- Non-Patent Document 4 teaches that among guanidine derivatives introduced with various substituents, only acyl derivatives exhibit antipoliovirus effects, and that the antipoliovirus effects of guanidine are structure-specific.
- Patent Document 5 discloses a method for treating tumor diseases and autoimmune diseases containing salts of guanidine derivatives such as undecylideneaminoguanidine acetate, undecylideneaminoguanidine lactate, undecylideneaminoguanidine enanthate and undecylideneaminoguanidine pelargonate. , discloses pharmaceutical preparations for the treatment of cardio-circulatory, infectious or viral diseases.
- Non-Patent Document 1 teaches guanidine salts and surfactants as virus inactivating agents.
- Non-Patent Document 2 discloses that urea and guanidine hydrochloride, which are known as protein denaturants, have a virus inactivating effect.
- Non-Patent Document 3 discloses a SARS-CoV-2 inactivation reagent containing guanidine thiocyanate as a main component.
- Patent Document 6 discloses 9-(2-hydroxyethoxymethyl)guanidine as an antiviral active agent.
- An object of the present invention is to provide an antiviral agent composition with excellent antiviral properties and uses thereof.
- An antiviral agent composition containing at least one selected from iminoctadine and salts thereof.
- a resin composition comprising the antiviral agent composition of [1] and a resin.
- a molded article containing the resin composition according to [2].
- the antiviral agent composition of the present invention exhibits excellent antiviral properties.
- a composition containing zinc pyrithione or polyhexamethylene biguanide and a resin has very low antiviral properties, but the resin composition, coating composition, adhesive composition or coating composition of the present invention exhibits good antiviral properties. have sex.
- the laminate of the present invention exhibits good antiviral properties.
- the molded article of the present invention has almost no effect on antiviral properties due to heat during molding, and exhibits good antiviral properties even in the shape of lumps, films, strands, filaments, fibers, and the like.
- the antiviral agent composition of the present invention contains at least one selected from iminoctadine and salts thereof (hereinafter sometimes referred to as iminoctadine compound).
- iminoctadine compound is also denoted as 1,1′-[iminodi(octamethylene)]diguanidine.
- iminoctadine salts used in the present invention include iminoctadine hydrochloride, iminoctadine albesilate, and iminoctadine acetate. Of these, iminoctadine albesilate or iminoctadine acetate are preferred.
- Iminoctazine acetate is also referred to as 1,1'-iminiodi(octamethylene)diguanidinium triacetate and is generally represented by the following structural formula.
- the amount of the iminoctadine compound contained in the antiviral agent composition of the present invention can be appropriately set according to the application. parts, more preferably 0.0005 to 75 parts by mass, still more preferably 0.0005 to 40 parts by mass, and particularly preferably 0.001 to 40 parts by mass.
- the antiviral agent composition of the present invention may contain a solvent.
- the solvent is preferably one capable of dispersing or dissolving the iminoctadine compound.
- Specific examples of solvents include water; ethylene glycol mono-n-butyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monobutyl ether, 2-ethylhexyl glycol, tripropylene glycol monomethyl ether, diethylene glycol monohexyl ether, Glycol ether solvents such as dipropylene glycol monomethyl ether and dipropylene glycol monobutyl ether; Organic acids such as formic acid, acetic acid, lactic acid, oxalic acid, citric acid, and benzoic acid; Methanol, ethanol, isopropyl alcohol, isobutyl alcohol, n- alcohols such as butanol; amines such as ethanolamine, dimethylamine and pyridine; amides such as di
- Hydrocarbons Halogenated hydrocarbons such as dichloromethane, carbon tetrachloride, chloroform, and chilichloroethylene; Acetonitrile; Mineral oil, synthetic hydrocarbon oil, synthetic ester oil, natural fat, natural fat derivative, ether oil, silicon oil, fluorine Oil etc. can be mentioned. These solvents can be used singly or in combination of two or more.
- the amount of the solvent contained in the antiviral agent composition of the present invention can be appropriately set according to the application. It is preferably 10 to 90 parts by mass, more preferably 30 to 90 parts by mass.
- the antiviral agent composition of the present invention can further contain components having antimicrobial properties other than the iminoctadine compound.
- components having antimicrobial properties include antibacterial components, bactericidal components, antiviral components, antifungal components, antiseptic components, antialgal components, and the like. These can be used individually by 1 type or in combination of 2 or more types.
- the antiviral agent composition of the present invention can further contain other ingredients depending on its purpose and application.
- Other ingredients include flame retardants, heat stabilizers, antioxidants, lubricants, antistatic agents, UV absorbers, colorants, dyes/pigments, release agents, heat shields, dispersants, and surfactants. . These can be used individually by 1 type or in combination of 2 or more types.
- the antiviral agent composition of the present invention can be formulated according to its purpose and application.
- Formulations of formulations include, for example, water suspensions, water emulsions, emulsions, liquids containing oils, pastes, powders, granules, microcapsules and the like.
- the antiviral agent composition of the present invention may be molded or granulated by known methods. Examples of molding or granulation methods include extrusion molding or extrusion granulation, stirring granulation, fluid bed granulation, tumbling granulation, spray granulation, compression granulation, and tableting.
- the liquid antiviral agent composition of the present invention can be added, mixed, applied, sprayed, impregnated, etc. with other materials.
- the solid antiviral agent composition of the present invention can be added, mixed, dispersed, adhered, etc. to other materials. By doing so, antiviral properties can be imparted to other materials.
- the antiviral agent composition of the present invention exhibits viral proliferation-suppressing and viral-killing effects. As a result, viral infection to humans, animals or plants can be prevented.
- viruses targeted by the antiviral agent composition of the present invention include Lassa fever virus, AIDS virus, West Nile virus, dengue fever virus, Japanese encephalitis virus, avian influenza virus, human influenza virus, smallpox virus, and herpes virus.
- papillomavirus Sindbis virus, coronavirus, SARS virus, norovirus, adenovirus, hepatitis B virus, Marburg virus, measles virus, rabies virus, poliovirus, rhinovirus, hepatitis A virus, rotavirus, hepatitis C Virus, Tobacco ring spot virus, Tobacco stem virus, Tobacco mosaic virus, Potato virus, Cucumber mosaic virus, Beet necrotic yellow vein virus, Capsicum mild mottle virus, Kidney bean mosaic virus, Kidney bean yellow mosaic virus, Peanut stunt Viruses, bacteriophages and the like can be mentioned.
- the resin composition of the present invention contains the antiviral agent composition of the present invention and a resin.
- the amount of the iminoctazine compound contained in the resin composition of the present invention can be appropriately set according to the application. is 0.0005 to 40 parts by mass, more preferably 0.001 to 20 parts by mass, and particularly preferably 0.001 to 5 parts by mass.
- the resin can be appropriately selected according to the application of the resin composition, the required performance, etc.
- resin is a resin in a broad sense, and includes elastomers, rubbers, etc., in addition to resins in a narrow sense.
- the resin in the present invention may be a thermoplastic resin, a thermosetting resin, or a photocurable resin.
- thermoplastic resins examples include styrene resins, acrylic resins, vinyl acetate resins, acrylonitrile copolymers, polyphenylene oxide resins, polysulfone resins, polyethersulfones, polyarylates, polyetherimides, polyamideimides, polyimides, and polymethacrylic acid.
- Thermosetting resins are those that are hardened by the progress of a polymerization reaction or a cross-linking reaction when heated.
- thermosetting resins include phenol resins, epoxy resins, melamine resins, urea resins, unsaturated polyester resins, alkyd resins, polyurethanes, thermosetting polyimides, and diallyl phthalate resins.
- the thermosetting resin may be a thermoplastic resin mixed with a vulcanizing agent, a curing agent, or a cross-linking agent.
- a photocurable resin is a resin that is cured by a polymerization reaction or a cross-linking reaction when irradiated with light such as ultraviolet rays.
- a desired monomer or oligomer is blended with a photoinitiator such as a photoradical generator, photocation generator, photoacid generator, or photobase generator.
- Monomers or oligomers that can be used in the photocurable resin are not particularly limited, and include (meth)acrylate monomers, (meth)acrylate oligomers, bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, cyclohexane di Methanol diglycidyl ether 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexanecarboxylate, 1,2-epoxy-4-(2-oxiranyl) of 2,2-bis(hydroxymethyl)-1-butanol Cyclohexane adducts; Oxetane compounds such as xylylene bisoxetane and 3-ethyl-3-hydroxymethyloxetane; Vinyl ether monomers such as cyclohexanedimethanol divinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovin
- resins include silicone, acrylic silicone, modified silicone, lacquer, glue, petroleum resin, and hydrogenated petroleum resin; starches such as rice, wheat, corn, potato, sweet potato, tapioca, and other natural products, or those made from and biodegradable plastics.
- the amount of the resin contained in the resin composition of the present invention can be appropriately set according to the application. 95 parts by mass, more preferably 50 to 90 parts by mass.
- the resin composition of the present invention is not particularly limited by the manufacturing method.
- it can be obtained by mixing an iminoctadine compound or the antiviral agent composition of the present invention, a resin, and, if necessary, a known resin additive by a known method.
- Additives for resins include antioxidants, heat deterioration inhibitors, light stabilizers, lubricants, release agents, polymer processing aids, antistatic agents, flame retardants, dyes and pigments, light diffusing agents, organic pigments, gloss Erasing agents, impact modifiers, phosphors, fillers, preservatives, anti-algae agents, pigment dispersants, plasticizers, drying accelerators, surfactants, anti-foaming agents, anti-skinning agents, low-temperature film-forming agents , film-forming aids, thickeners, leveling agents, dispersants, anti-settling agents, curing agents, curing aids, anti-freezing agents, and the like.
- a resin, and known additives for resins that are optionally used can be carried out using, for example, a kneader-ruder, a single-screw or multi-screw extruder, a mixing roll, and a Banbury mixer. It can be carried out using a known mixing device or kneading device such as.
- the liquid thermosetting resin or photocurable resin before curing can be mixed with the iminoctadine compound or the antiviral agent composition of the present invention and known resin additives used as necessary by tank blending.
- the resin composition of the present invention can be made into a desired shape by a known molding method. Further, the liquid resin composition of the present invention can be added, applied, sprayed, or impregnated into other materials. The solid resin composition of the present invention can be mixed and adhered to other materials.
- the molded article of the present invention contains the resin composition of the present invention.
- the molded article of the present invention can be obtained by shaping the resin composition of the present invention into a desired shape by a known molding method. Examples of molding methods include extrusion molding, injection molding, compression molding, blow molding, cast molding, lamination molding, lamination molding, and powder molding.
- the coating composition, adhesive composition or coating composition of the present invention contains an iminoctadine compound.
- the amount of the iminoctazine compound contained in the coating composition, adhesive composition or coating composition of the present invention can be appropriately set depending on the application.
- the coating composition, adhesive composition, or coating composition of the present invention contains, in addition to the iminoctadine compound, components that can be included in known coating compositions, adhesive compositions, or coating compositions (e.g., resins, solvents, , additives, etc.).
- the components can impart to the respective composition properties suitable for coatings, adhesives or paints. Properties include fluidity, adhesiveness, coatability, film-forming properties, lamination properties, blister resistance, adhesion, adhesiveness, sealing properties, decorative properties, and the like. Such characteristics can be realized by appropriately selecting the type and amount of resin to be used, the type and amount of solvent, the type and amount of additive, and the like.
- the liquid coating composition of the present invention is applied onto a substrate by a coating method such as brush coating, roll coating, bar coating, or spray coating, and then dried and, if necessary, cured.
- the substrate can be coated by
- the solid coating composition of the present invention can be placed on a substrate by dusting, sheeting, filming, or the like, and the substrate can be coated by pressing, fusing or adhering. .
- the antiviral agent composition, resin composition, coating composition, adhesive composition, or coating composition of the present invention can be used for various purposes.
- Synthetic resin paints include phenol resin paints, phthalate resin paints (e.g. alkyd resin paints), maleic acid resin paints, urea resin paints, melamine resin paints, vinyl resin paints (e.g. vinyl acetate resin paints, vinyl chloride resin paints). paint, styrene resin paint, acrylic acid resin paint, polyvinyl butyral resin paint, etc.), epoxy resin paint, silicone resin paint, furan resin paint, polyester resin paint, urethane resin paint, nitrocellulose resin paint, amino resin paint, fluorine resin paint etc. can be mentioned.
- Water-based paints include water-based paints, emulsion oil paints, emulsion polymerization paints (for example, vinyl acetate resin emulsion polymerization paints, vinylidene chloride vinyl chloride copolymer emulsion polymerization paints, acrylic acid resin emulsion polymerization paints, styrene resin emulsion polymerization paints, synthetic rubber latex paint, etc.).
- emulsion oil paints for example, vinyl acetate resin emulsion polymerization paints, vinylidene chloride vinyl chloride copolymer emulsion polymerization paints, acrylic acid resin emulsion polymerization paints, styrene resin emulsion polymerization paints, synthetic rubber latex paint, etc.
- the resin composition, coating composition, or coating composition of the present invention can further contain a coupling agent.
- a coupling agent is a compound that bonds materials with different properties, mainly inorganic and organic materials.
- Examples of coupling agents include silane coupling agents, titanate coupling agents, aluminate coupling agents, and zirconate coupling agents.
- Silane coupling agents include 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane.
- ethoxysilane 3-glycidoxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, etc. can be mentioned.
- Titanate-based coupling agents include titanium alkoxides such as tetraisopropyl titanate, tetra-n-butyl titanate, tetrakis(2-ethylhexyloxy)titanium, titanium-i-propoxyoctylene glycolate; titanium acetylacetonate, titanium tetraacetyl Acetonate, di-i-propoxy bis(acetylacetonato)titanium, di-n-propoxy bis(acetylacetonato)titanium, di-n-butoxy bis(acetylacetonato)titanium, diethoxy bis(acetyl acetonate), titanium complexes such as propanedioxytitanium bis(ethylacetoacetate), and the like.
- titanium alkoxides such as tetraisopropyl titanate, tetra-n-butyl titanate, tetrakis(2-
- aluminate-based coupling agents include aluminum alcoholates such as aluminum isopropylate, mono-sec-butoxyaluminum diisopropylate, and aluminum ethylate; ethylacetoacetate aluminum diisopropylate, aluminum bisethylacetoacetate/monoacetyl Acetonate, aluminum tris (ethylacetoacetate), aluminum tris (acetylacetonate), diethoxy mono (acetylacetonate) aluminum, di-i-propoxy mono (acetylacetonate) aluminum, di-n-propoxy mono (acetylacetonate) ) aluminum, di-n-butoxymono(acetylacetonato)aluminum, ethoxybis(acetylacetonato)aluminum, i-propoxybis(acetylacetonato)aluminum, n-propoxybis(acetylacetonato)aluminum, n-butoxybis
- Zirconate-based coupling agents include zirconium tetrakis (acetylacetonate), di-n-butoxybis (acetylacetonate) zirconium, zirconium tetrakis (ethylacetoacetate), diethoxybis acetylacetonate zirconium, and di-i-propoxybis.
- the resin composition, coating composition, or coating composition of the present invention may further contain a filler.
- Fillers include carbon black, graphene, carbon nanotube, glass fiber, iron oxide, barite, talc, calcium carbonate, kaolin, clay, silica, titanium dioxide, alumina, zirconia, silicone resin fine particles, fluororesin fine particles, acrylic resin fine particles, Examples include urethane-based resin fine particles, silicone-modified urethane-based resin fine particles, polyethylene fine particles, and polycarbonate-based resin fine particles.
- the laminate of the present invention comprises a substrate and a layer of the resin composition, coating composition, adhesive composition or coating composition of the present invention laminated thereon.
- Substrates that can be used in the present invention are not particularly limited. Examples of base materials include buildings in general, building materials, metals, rubbers, wood materials, plastic products, fibers, cloth, paper, ceramics, concrete, blocks, and bricks.
- a layer composed of the resin composition, coating composition, adhesive composition, or coating composition of the present invention does not impair the appearance because the color tone does not easily change over time, and exhibits excellent antiviral properties.
- Lamination on the substrate can be performed by a known method. For example, multicolor extrusion molding, coated extrusion molding, adhesion, fusion bonding, coating, spraying, powder molding, in-mold molding, film insert molding and the like can be mentioned.
- Example 1 82.73 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved.
- a silane coupling agent 3-methacryloxypropyltrimethoxysilane
- organosilica sol amorphous silica 30%, N-methyl-2-pyrrolidone 70%
- aluminum (III) acetylacetonate 1.5 parts by mass
- 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved.
- composition A was applied to one side of a polyethylene terephthalate film (Lumirror (R) film (T60 transparent) 250 ⁇ m) of 148 mm ⁇ 210 mm using an automatic coating device (PI-1210: manufactured by Tester Sangyo Co., Ltd.). . After that, it was placed in a constant temperature bath at 100° C. and dried for 20 minutes. Next, the dried coating film was cured using an ultraviolet curing light source device (manufactured by Eyegraphics Co., Ltd.) to obtain a laminate in which a polyethylene terephthalate film and a film composed of non-volatile components of composition A were laminated.
- PI-1210 manufactured by Tester Sangyo Co., Ltd.
- the infectivity titer U was calculated in the same manner as above. From the calculated infectious titer T and infectious titer U, the antiviral activity value was calculated.
- the antiviral activity value is a value defined by the following formula.
- Antiviral activity value Log (infectious value U) - Log (infectious value T) The antiviral activity value against bacteriophage Q ⁇ was 4.8.
- the antiviral activity value was calculated in the same manner as described above, except that the bacteriophage ⁇ 6-containing solution was used instead of the bacteriophage Q ⁇ -containing solution, and the Pseudomonas syringae culture solution was used instead of the E. coli culture solution.
- the antiviral activity value against bacteriophage ⁇ 6 was 5.2.
- Example 2 83.56 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved.
- a silane coupling agent 3-methacryloxypropyltrimethoxysilane
- organosilica sol amorphous silica 30%, N-methyl-2-pyrrolidone 70%
- aluminum (III) acetylacetonate 1.5 parts by mass
- 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved.
- Example 3 85.23 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved.
- a silane coupling agent 3-methacryloxypropyltrimethoxysilane
- organosilica sol amorphous silica 30%, N-methyl-2-pyrrolidone 70%
- aluminum (III) acetylacetonate 1.5 parts by mass
- 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved.
- composition D was applied to one side of a polyethylene terephthalate film (Lumirror (R) film (T60 transparent) 250 ⁇ m) of 148 mm ⁇ 210 mm using an automatic coating device (PI-1210: manufactured by Tester Sangyo Co., Ltd.). . After that, it was placed in a constant temperature bath at 100° C. and dried for 1 minute to obtain a laminate in which a polyethylene terephthalate film and a film composed of non-volatile components of composition D were laminated.
- Antiviral evaluation was performed using bacteriophage ⁇ 6. The antiviral activity value against bacteriophage ⁇ 6 was 5.2.
- composition E 5.0 parts by mass of a polyhexamethylene biguanide preparation (containing 20% polyhexamethylene biguanide) (1 part as polyhexamethylene biguanide) was added and mixed to obtain a liquid composition E.
- a laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition E.
- Antiviral evaluation using bacteriophage Q ⁇ was performed.
- the antiviral activity value against bacteriophage Q ⁇ was 2.0.
- composition containing polyhexamethylene biguanide and resin has extremely low antiviral properties, but the composition of the present invention (Example) has good antiviral properties.
Abstract
The present invention provides an antiviral agent composition which exhibits excellent antiviral properties, and a use therefor. This antiviral agent composition contains iminoctadine or a salt thereof. The present invention prepares a composition (antiviral agent composition, resin composition, coating composition, coating material composition, etc.) by mixing an iminoctadine compound such as iminoctadine, iminoctadine alkyl benzenesulphonate, and iminoctadine acetate with a solvent, a resin and an additive. This composition can be molded into a desired shape, coated onto another substrate, and used when adhering.
Description
本発明は、抗ウイルス剤組成物に関する。より詳細に、本発明は、抗ウイルス性に優れる抗ウイルス剤組成物およびその用途に関する。本願は、２０２２年３月３日に出願された日本国特許出願第２０２２－３２６７３号に対し優先権を主張し、その内容をここに援用する。
The present invention relates to antiviral agent compositions. More specifically, the present invention relates to an antiviral agent composition with excellent antiviral properties and uses thereof. This application claims priority to Japanese Patent Application No. 2022-32673 filed on March 3, 2022, the contents of which are incorporated herein.
ヒト、動物または植物に悪影響を及ぼすウイルス、例えば、コロナウイルス（SARS-CoV、SARS-CoV-2、MERS-CoV、HCoV-229E、HCoV-OC43、HCoV-NL63、HCoV-HKU1など）、Ｂ型肝炎ウイルス、Ｃ型肝炎ウイルス、Ｅ型肝炎ウイルス、狂犬病ウイルス、エボラ出血熱ウイルス、ＡＩＤＳウイルス、ノロウイルス、ポリオウイルス、ロタウイルス、ラッサ熱ウイルス、エイズウイルス、西ナイルウイルス、デング熱ウイルス、日本脳炎ウイルス、鳥インフルエンザウイルス、人インフルエンザウイルス、天然痘ウイルス、ヘルペスウイルスなど、の感染を防ぐための抗ウイルス剤の開発が要望されている。
Viruses that adversely affect humans, animals or plants, e.g. coronaviruses (SARS-CoV, SARS-CoV-2, MERS-CoV, HCoV-229E, HCoV-OC43, HCoV-NL63, HCoV-HKU1, etc.), type B Hepatitis virus, hepatitis C virus, hepatitis E virus, rabies virus, Ebola virus, AIDS virus, norovirus, poliovirus, rotavirus, Lassa fever virus, AIDS virus, West Nile virus, dengue fever virus, Japanese encephalitis virus, bird flu There is a demand for the development of antiviral agents for preventing infection with viruses, human influenza virus, smallpox virus, herpes virus, and the like.
抗ウイルス剤として期待される物質が種々提案されている。
例えば、特許文献１は、平均分子量２９００～１５０００のポリヘキサメチレンビグアニドを含有する抗感染症薬剤を開示している。 Various substances expected as antiviral agents have been proposed.
For example, US Pat. No. 5,900,000 discloses an anti-infective agent containing polyhexamethylene biguanide with an average molecular weight of 2,900-15,000.
例えば、特許文献１は、平均分子量２９００～１５０００のポリヘキサメチレンビグアニドを含有する抗感染症薬剤を開示している。 Various substances expected as antiviral agents have been proposed.
For example, US Pat. No. 5,900,000 discloses an anti-infective agent containing polyhexamethylene biguanide with an average molecular weight of 2,900-15,000.
特許文献２は、０．０５～０．５ｗｔ％のポリヘキサメチレングアニジン系化合物および４０～９５ｗｔ％の低級アルコールまたはこれらの混合物を含み、ｐＨが６～９の範囲にあることを特徴としたカリシウイルス不活化効果を有する組成物を開示している。
Patent Document 2 discloses a potash characterized by containing 0.05 to 0.5 wt% of a polyhexamethylene guanidine compound and 40 to 95 wt% of a lower alcohol or a mixture thereof, and having a pH in the range of 6 to 9. Compositions with virus-inactivating effects are disclosed.
特許文献３および特許文献４は、置換アシルグアニジンに分類される一部の化合物が、多様なウイルスに対して抗ウイルス活性を有することを見出したと述べている。
非特許文献４は、種々の置換基を導入したグアニジン誘導体のうち、アシル誘導体のみが、抗ポリオウイルス効果を示し、グアニジンの抗ポリオウイルス効果が構造特異的であると教示している。 WO 2005/010003 and WO 2005/020003 state that some compounds classified as substituted acylguanidines have been found to have antiviral activity against a variety of viruses.
Non-Patent Document 4 teaches that among guanidine derivatives introduced with various substituents, only acyl derivatives exhibit antipoliovirus effects, and that the antipoliovirus effects of guanidine are structure-specific.
非特許文献４は、種々の置換基を導入したグアニジン誘導体のうち、アシル誘導体のみが、抗ポリオウイルス効果を示し、グアニジンの抗ポリオウイルス効果が構造特異的であると教示している。 WO 2005/010003 and WO 2005/020003 state that some compounds classified as substituted acylguanidines have been found to have antiviral activity against a variety of viruses.
Non-Patent Document 4 teaches that among guanidine derivatives introduced with various substituents, only acyl derivatives exhibit antipoliovirus effects, and that the antipoliovirus effects of guanidine are structure-specific.
特許文献５は、ウンデシリデンアミノグアニジンアセテート、ウンデシリデンアミノグアニジンラクテート、ウンデシリデンアミノグアニジンエナンタート及びウンデシリデンアミノグアニジンペラルゴネートなどのグアニジン誘導体の塩を含有する、腫瘍疾患、自己免疫疾患、心臓－循環疾患、感染症又はウイルス性疾患の治療のための製薬学的調剤を開示している。
Patent Document 5 discloses a method for treating tumor diseases and autoimmune diseases containing salts of guanidine derivatives such as undecylideneaminoguanidine acetate, undecylideneaminoguanidine lactate, undecylideneaminoguanidine enanthate and undecylideneaminoguanidine pelargonate. , discloses pharmaceutical preparations for the treatment of cardio-circulatory, infectious or viral diseases.
非特許文献１は、ウイルス不活化剤としてグアニジン塩や界面活性剤を教示している。
非特許文献２は、タンパク質変性剤として知られている尿素や塩酸グアニジンがウイルス不活化作用を有することを開示している。 Non-Patent Document 1 teaches guanidine salts and surfactants as virus inactivating agents.
Non-Patent Document 2 discloses that urea and guanidine hydrochloride, which are known as protein denaturants, have a virus inactivating effect.
非特許文献２は、タンパク質変性剤として知られている尿素や塩酸グアニジンがウイルス不活化作用を有することを開示している。 Non-Patent Document 1 teaches guanidine salts and surfactants as virus inactivating agents.
Non-Patent Document 2 discloses that urea and guanidine hydrochloride, which are known as protein denaturants, have a virus inactivating effect.
非特許文献３は、グアニジンチオシアン酸塩を主要成分とするSARS-CoV-2不活化試薬を開示している。
Non-Patent Document 3 discloses a SARS-CoV-2 inactivation reagent containing guanidine thiocyanate as a main component.
特許文献６は、抗ウイルス活性薬として９－（２－ヒドロキシエトキシメチル）グアニジンを開示している。
Patent Document 6 discloses 9-(2-hydroxyethoxymethyl)guanidine as an antiviral active agent.
本発明の目的は、抗ウイルス性に優れる抗ウイルス剤組成物およびその用途を提供することである。
An object of the present invention is to provide an antiviral agent composition with excellent antiviral properties and uses thereof.
上記目的を達成するために検討した結果、以下の形態を包含する本発明を完成するに至った。
As a result of studies to achieve the above objectives, the present invention including the following forms has been completed.
〔１〕 イミノクタジン及びその塩から選ばれる少なくとも一つを含有する、抗ウイルス剤組成物。
〔２〕 〔１〕に記載の抗ウイルス剤組成物、および樹脂を含有する、樹脂組成物。
〔３〕 〔２〕に記載の樹脂組成物を含有して成る、成形体。 [1] An antiviral agent composition containing at least one selected from iminoctadine and salts thereof.
[2] A resin composition comprising the antiviral agent composition of [1] and a resin.
[3] A molded article containing the resin composition according to [2].
〔２〕 〔１〕に記載の抗ウイルス剤組成物、および樹脂を含有する、樹脂組成物。
〔３〕 〔２〕に記載の樹脂組成物を含有して成る、成形体。 [1] An antiviral agent composition containing at least one selected from iminoctadine and salts thereof.
[2] A resin composition comprising the antiviral agent composition of [1] and a resin.
[3] A molded article containing the resin composition according to [2].
本発明の抗ウイルス剤組成物は、優れた抗ウイルス性を奏する。亜鉛ピリチオンまたはポリヘキサメチレンビグアナイドと樹脂とを含有する組成物は抗ウイルス性が極めて低いが、本発明の樹脂組成物、被覆用組成物、接着剤組成物または塗料組成物は、良好な抗ウイルス性を有する。本発明の積層体は、良好な抗ウイルス性を奏する。
本発明の成形体は、成形時の熱などによる抗ウイルス性に対する影響がほとんどなく、例えば、塊形状、フィルム形状、ストランド形状、フィラメント形状、ファイバー形状などにおいても、良好な抗ウイルス性を奏する。 The antiviral agent composition of the present invention exhibits excellent antiviral properties. A composition containing zinc pyrithione or polyhexamethylene biguanide and a resin has very low antiviral properties, but the resin composition, coating composition, adhesive composition or coating composition of the present invention exhibits good antiviral properties. have sex. The laminate of the present invention exhibits good antiviral properties.
The molded article of the present invention has almost no effect on antiviral properties due to heat during molding, and exhibits good antiviral properties even in the shape of lumps, films, strands, filaments, fibers, and the like.
本発明の成形体は、成形時の熱などによる抗ウイルス性に対する影響がほとんどなく、例えば、塊形状、フィルム形状、ストランド形状、フィラメント形状、ファイバー形状などにおいても、良好な抗ウイルス性を奏する。 The antiviral agent composition of the present invention exhibits excellent antiviral properties. A composition containing zinc pyrithione or polyhexamethylene biguanide and a resin has very low antiviral properties, but the resin composition, coating composition, adhesive composition or coating composition of the present invention exhibits good antiviral properties. have sex. The laminate of the present invention exhibits good antiviral properties.
The molded article of the present invention has almost no effect on antiviral properties due to heat during molding, and exhibits good antiviral properties even in the shape of lumps, films, strands, filaments, fibers, and the like.
本発明の抗ウイルス剤組成物は、イミノクタジン及びその塩から選ばれる少なくとも一つ（以下、イミノクタジン化合物ということがある。）を含有するものである。
本発明に用いられるイミノクタジンは、１，１’－［イミノジ（オクタメチレン）］ジグアニジンとも表記される。
The antiviral agent composition of the present invention contains at least one selected from iminoctadine and salts thereof (hereinafter sometimes referred to as iminoctadine compound).
Iminoctazine used in the present invention is also denoted as 1,1′-[iminodi(octamethylene)]diguanidine.
本発明に用いられるイミノクタジンは、１，１’－［イミノジ（オクタメチレン）］ジグアニジンとも表記される。
Iminoctazine used in the present invention is also denoted as 1,1′-[iminodi(octamethylene)]diguanidine.
本発明に用いられるイミノクタジンの塩としては、イミノクタジン塩酸塩、イミノクタジンアルベシル酸塩、イミノクタジン酢酸塩などを挙げることができる。これらのうち、イミノクタジンアルベシル酸塩またはイミノクタジン酢酸塩が好ましい。
Examples of iminoctadine salts used in the present invention include iminoctadine hydrochloride, iminoctadine albesilate, and iminoctadine acetate. Of these, iminoctadine albesilate or iminoctadine acetate are preferred.
イミノクタジンアルベシル酸塩は、１，１’－イミニオジ（オクタメチレン）ジグアニジウム＝トリス（ドデシルベンゼンスルホネート）とも表記され、一般的に、下記の構造式で表わされる。
Iminoctadine albesilate is also abbreviated as 1,1′-iminiodi(octamethylene)diguanidinium=tris(dodecylbenzenesulfonate) and is generally represented by the following structural formula.
イミノクタジン酢酸塩は、１，１’―イミニオジ（オクタメチレン）ジグアニジウム＝トリアセテートとも表記され、一般的に、下記の構造式で表わされる。
Iminoctazine acetate is also referred to as 1,1'-iminiodi(octamethylene)diguanidinium triacetate and is generally represented by the following structural formula.
本発明の抗ウイルス剤組成物に含有するイミノクタジン化合物の量は、用途に応じて適宜設定することができ、例えば、抗ウイルス剤組成物１００質量部に対して、好ましくは０．０００１～７５質量部、より好ましくは０．０００５～７５質量部、さらに好ましくは０．０００５～４０質量部、特に好ましくは０．００１～４０質量部である。
The amount of the iminoctadine compound contained in the antiviral agent composition of the present invention can be appropriately set according to the application. parts, more preferably 0.0005 to 75 parts by mass, still more preferably 0.0005 to 40 parts by mass, and particularly preferably 0.001 to 40 parts by mass.
本発明の抗ウイルス剤組成物は、溶媒を含んでいてもよい。溶媒は、イミノクタジン化合物を分散又は溶解させることができるものが好ましい。溶媒の具体例としては、例えば、水； エチレングリコールモノｎ－ブチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノブチルエーテル、２-エチルヘキシルグリコール、トリプロピレングリコールモノメチルエーテル、ジエチレングリコールモノヘキシルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノブチルエーテル等のグリコールエーテル系の溶媒； 蟻酸、酢酸、乳酸、シュウ酸、クエン酸、安息香酸等の有機酸類； メタノール、エタノール、イソプロピルアルコール、イソブチルアルコール、ｎ－ブタノール等のアルコール類； エタノールアミン、ジメチルアミン、ピリジン等のアミン類； ジメチルホルムアミド、ジメチルアセトアミド、Ｎ－メチルピロリドン等のアミド類； アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、アセチルアセトン等のケトン類； ジエチルエーテル、ジメチルエーテル、テトラヒドロフラン等のエーテル類； エチルセロソルブ、ブチルセロソルブ、プロピレングリコールモノメチルエーテル等のヒドロキシエーテル類； 酢酸エチル、酢酸ブチル、乳酸エチル、乳酸ブチル等のエステル類； ヘキサン、ベンゼン、キシレン、トルエン等の炭化水素類； ジクロロメタン、四塩化炭素、クロロホルム、チリクロロエチレン等のハロゲン化炭化水素類； アセトニトリル； 鉱油、合成炭化水素油、合成エステル油、天然油脂、天然油脂誘導体、エーテル油、シリコン油、フッ素油等を挙げることができる。これらの溶媒は、１種単独で又は２種以上を組み合わせて、用いることができる。
The antiviral agent composition of the present invention may contain a solvent. The solvent is preferably one capable of dispersing or dissolving the iminoctadine compound. Specific examples of solvents include water; ethylene glycol mono-n-butyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monobutyl ether, 2-ethylhexyl glycol, tripropylene glycol monomethyl ether, diethylene glycol monohexyl ether, Glycol ether solvents such as dipropylene glycol monomethyl ether and dipropylene glycol monobutyl ether; Organic acids such as formic acid, acetic acid, lactic acid, oxalic acid, citric acid, and benzoic acid; Methanol, ethanol, isopropyl alcohol, isobutyl alcohol, n- alcohols such as butanol; amines such as ethanolamine, dimethylamine and pyridine; amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and acetylacetone; diethyl Ethers such as ether, dimethyl ether, and tetrahydrofuran; Hydroxy ethers such as ethyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; Esters such as ethyl acetate, butyl acetate, ethyl lactate, and butyl lactate; Hexane, benzene, xylene, toluene, etc. Hydrocarbons; Halogenated hydrocarbons such as dichloromethane, carbon tetrachloride, chloroform, and chilichloroethylene; Acetonitrile; Mineral oil, synthetic hydrocarbon oil, synthetic ester oil, natural fat, natural fat derivative, ether oil, silicon oil, fluorine Oil etc. can be mentioned. These solvents can be used singly or in combination of two or more.
本発明の抗ウイルス剤組成物に含有する溶媒の量は、用途に応じて適宜設定することができ、例えば、抗ウイルス剤組成物１００質量部に対して、好ましくは５～９０質量部、より好ましくは１０～９０質量部、さらに好ましくは３０～９０質量部である。
The amount of the solvent contained in the antiviral agent composition of the present invention can be appropriately set according to the application. It is preferably 10 to 90 parts by mass, more preferably 30 to 90 parts by mass.
本発明の抗ウイルス剤組成物は、イミノクタジン化合物以外の、抗微生物性等を有する成分をさらに含有することができる。抗微生物性等を有する成分としては、抗菌成分、殺菌成分、抗ウイルス成分、防黴成分、防腐成分、防藻成分などを挙げることができる。これらは１種単独で若しくは２種以上を組み合わせて用いることができる。
The antiviral agent composition of the present invention can further contain components having antimicrobial properties other than the iminoctadine compound. Examples of components having antimicrobial properties include antibacterial components, bactericidal components, antiviral components, antifungal components, antiseptic components, antialgal components, and the like. These can be used individually by 1 type or in combination of 2 or more types.
本発明の抗ウイルス剤組成物は、その目的および用途に応じて、他の成分をさらに含有することができる。他の成分としては、難燃剤、熱安定剤、酸化防止剤、滑性剤、帯電防止剤、紫外線吸収剤、着色剤、染料／顔料、離型剤、遮熱剤、分散剤、界面活性剤、ｐＨ調整剤、消泡剤、防錆剤、粘度調整剤、金属封鎖剤、摩擦調整剤、フィラー、ラック貝殻虫の殻などを挙げることができる。これらは１種単独で若しくは２種以上を組み合わせて用いることができる。
The antiviral agent composition of the present invention can further contain other ingredients depending on its purpose and application. Other ingredients include flame retardants, heat stabilizers, antioxidants, lubricants, antistatic agents, UV absorbers, colorants, dyes/pigments, release agents, heat shields, dispersants, and surfactants. . These can be used individually by 1 type or in combination of 2 or more types.
本発明の抗ウイルス剤組成物は、その目的および用途に応じて、製剤化することができる。製剤の剤型としては、例えば、水懸濁剤、水乳濁剤、乳剤、油剤などを含む液剤、ペースト剤、粉剤、粒剤、マイクロカプセルなどを挙げることができる。
本発明の抗ウイルス剤組成物は、公知の方法によって成形または造粒してもよい。成形若しくは造粒の方法としては、押出成形若しくは押出造粒、攪拌造粒、流動層造粒、転動造粒、噴霧造粒、圧縮造粒若しくは打錠成形などを挙げることができる。 The antiviral agent composition of the present invention can be formulated according to its purpose and application. Formulations of formulations include, for example, water suspensions, water emulsions, emulsions, liquids containing oils, pastes, powders, granules, microcapsules and the like.
The antiviral agent composition of the present invention may be molded or granulated by known methods. Examples of molding or granulation methods include extrusion molding or extrusion granulation, stirring granulation, fluid bed granulation, tumbling granulation, spray granulation, compression granulation, and tableting.
本発明の抗ウイルス剤組成物は、公知の方法によって成形または造粒してもよい。成形若しくは造粒の方法としては、押出成形若しくは押出造粒、攪拌造粒、流動層造粒、転動造粒、噴霧造粒、圧縮造粒若しくは打錠成形などを挙げることができる。 The antiviral agent composition of the present invention can be formulated according to its purpose and application. Formulations of formulations include, for example, water suspensions, water emulsions, emulsions, liquids containing oils, pastes, powders, granules, microcapsules and the like.
The antiviral agent composition of the present invention may be molded or granulated by known methods. Examples of molding or granulation methods include extrusion molding or extrusion granulation, stirring granulation, fluid bed granulation, tumbling granulation, spray granulation, compression granulation, and tableting.
液体状の本発明の抗ウイルス剤組成物は、他の材料に、添加、混合、塗布、噴霧、含浸などをさせることができる。固体状の本発明の抗ウイルス剤組成物は、他の材料に、添加、混合、散布、付着などをさせることができる。このようにすることによって、他の材料に、抗ウイルス性を付与することができる。
The liquid antiviral agent composition of the present invention can be added, mixed, applied, sprayed, impregnated, etc. with other materials. The solid antiviral agent composition of the present invention can be added, mixed, dispersed, adhered, etc. to other materials. By doing so, antiviral properties can be imparted to other materials.
本発明の抗ウイルス剤組成物は、ウイルスの増殖抑制効果およびウイルスの殺滅効果を奏する。その結果、ヒト、動物または植物へのウイルス感染を防止できる。
本発明の抗ウイルス剤組成物が対象とするウイルスとしては、例えば、ラッサ熱ウイルス、エイズウイルス、西ナイルウイルス、デング熱ウイルス、日本脳炎ウイルス、鳥インフルエンザウイルス、人インフルエンザウイルス、天然痘ウイルス、ヘルペスウイルス、パピローマウイルス，シンドビスウイルス，コロナウイルス、ＳＡＲＳウイルス、ノロウイルス、アデノウイルス、Ｂ型肝炎ウイルス、マールブルグウイルス、麻しんウイルス、狂犬病ウイルス、ポリオウイルス、ライノウイルス、Ａ型肝炎ウイルス、ロタウイルス、Ｃ型肝炎ウイルス、タバコ輪点ウイルス、タバコ茎えそウイルス、タバコモザイクウイルス、ジャガイモウイルス、キュウリモザイクウイルス、ビートえそ性葉脈黄化ウイルス、トウガラシマイルドモットルウイルス、インゲンマメモザイクウイルス、インゲンマメ黄斑モザイクウイルス、ピーナッツスタントウイルス、バクテリオファージなどを挙げることができる。 INDUSTRIAL APPLICABILITY The antiviral agent composition of the present invention exhibits viral proliferation-suppressing and viral-killing effects. As a result, viral infection to humans, animals or plants can be prevented.
Examples of viruses targeted by the antiviral agent composition of the present invention include Lassa fever virus, AIDS virus, West Nile virus, dengue fever virus, Japanese encephalitis virus, avian influenza virus, human influenza virus, smallpox virus, and herpes virus. , papillomavirus, Sindbis virus, coronavirus, SARS virus, norovirus, adenovirus, hepatitis B virus, Marburg virus, measles virus, rabies virus, poliovirus, rhinovirus, hepatitis A virus, rotavirus, hepatitis C Virus, Tobacco ring spot virus, Tobacco stem virus, Tobacco mosaic virus, Potato virus, Cucumber mosaic virus, Beet necrotic yellow vein virus, Capsicum mild mottle virus, Kidney bean mosaic virus, Kidney bean yellow mosaic virus, Peanut stunt Viruses, bacteriophages and the like can be mentioned.
本発明の抗ウイルス剤組成物が対象とするウイルスとしては、例えば、ラッサ熱ウイルス、エイズウイルス、西ナイルウイルス、デング熱ウイルス、日本脳炎ウイルス、鳥インフルエンザウイルス、人インフルエンザウイルス、天然痘ウイルス、ヘルペスウイルス、パピローマウイルス，シンドビスウイルス，コロナウイルス、ＳＡＲＳウイルス、ノロウイルス、アデノウイルス、Ｂ型肝炎ウイルス、マールブルグウイルス、麻しんウイルス、狂犬病ウイルス、ポリオウイルス、ライノウイルス、Ａ型肝炎ウイルス、ロタウイルス、Ｃ型肝炎ウイルス、タバコ輪点ウイルス、タバコ茎えそウイルス、タバコモザイクウイルス、ジャガイモウイルス、キュウリモザイクウイルス、ビートえそ性葉脈黄化ウイルス、トウガラシマイルドモットルウイルス、インゲンマメモザイクウイルス、インゲンマメ黄斑モザイクウイルス、ピーナッツスタントウイルス、バクテリオファージなどを挙げることができる。 INDUSTRIAL APPLICABILITY The antiviral agent composition of the present invention exhibits viral proliferation-suppressing and viral-killing effects. As a result, viral infection to humans, animals or plants can be prevented.
Examples of viruses targeted by the antiviral agent composition of the present invention include Lassa fever virus, AIDS virus, West Nile virus, dengue fever virus, Japanese encephalitis virus, avian influenza virus, human influenza virus, smallpox virus, and herpes virus. , papillomavirus, Sindbis virus, coronavirus, SARS virus, norovirus, adenovirus, hepatitis B virus, Marburg virus, measles virus, rabies virus, poliovirus, rhinovirus, hepatitis A virus, rotavirus, hepatitis C Virus, Tobacco ring spot virus, Tobacco stem virus, Tobacco mosaic virus, Potato virus, Cucumber mosaic virus, Beet necrotic yellow vein virus, Capsicum mild mottle virus, Kidney bean mosaic virus, Kidney bean yellow mosaic virus, Peanut stunt Viruses, bacteriophages and the like can be mentioned.
本発明の樹脂組成物は、本発明の抗ウイルス剤組成物と樹脂とを含有するものである。
The resin composition of the present invention contains the antiviral agent composition of the present invention and a resin.
本発明の樹脂組成物に含有するイミノクタジン化合物の量は、用途に応じて適宜設定することができ、例えば、樹脂組成物１００質量部に対して、好ましくは０．０００１～７０質量部、より好ましくは０．０００５～４０質量部、さらに好ましくは０．００１～２０質量部であり、特に好ましくは０．００１～５質量部である。
The amount of the iminoctazine compound contained in the resin composition of the present invention can be appropriately set according to the application. is 0.0005 to 40 parts by mass, more preferably 0.001 to 20 parts by mass, and particularly preferably 0.001 to 5 parts by mass.
樹脂は、樹脂組成物の用途、求められる性能等に応じて、適宜選択することができる。本発明において樹脂は、広義の樹脂であり、狭義の樹脂以外に、エラストマー、ゴムなどを包含する。本発明における樹脂は、熱可塑性の樹脂であっても、熱硬化性の樹脂であっても、光硬化性の樹脂であってもよい。
The resin can be appropriately selected according to the application of the resin composition, the required performance, etc. In the present invention, resin is a resin in a broad sense, and includes elastomers, rubbers, etc., in addition to resins in a narrow sense. The resin in the present invention may be a thermoplastic resin, a thermosetting resin, or a photocurable resin.
熱可塑性樹脂としては、例えば、スチレン系樹脂、アクリル樹脂、酢酸ビニル樹脂、アクリロニトリル共重合体、ポリフェニレンオキサイド樹脂、ポリスルホン樹脂、ポリエーテルスルホン、ポリアリレート、ポリエーテルイミド、ポリアミドイミド、ポリイミド、ポリメタクリル酸メチル、アクリロニトリル－スチレン共重合体樹脂、アクリロニトリル－スチレン－Ｎ－置換マレイミド三元共重合体、アクリロニトリル－ブタジエン－スチレン共重合体樹脂、スチレン－無水マレイン酸共重合体樹脂、スチレン－無水マレイン酸－Ｎ－置換マレイミド共重合体樹脂、ポリカーボネート樹脂、ポリブチレンテレフタレート樹脂、ポリエチレン（直鎖状低密度ポリエチレン、低密度ポリエチレン、高密度ポリエチレンなど）、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリ塩化ビニル、ポリプロピレン、スチレン－ブタジエン－スチレンブロック共重合体およびその水添物、スチレン－ブタジエンゴム、アクリロニトリル－ブタジエンゴム、ポリブタジエン、ポリイソプレン、スチレン－イソプレン－スチレンブロック共重合体およびその水添物、ポリオレフィン系エラストマー、ポリエステル系エラストマー、ポリスチレン、アクリル樹脂、メタクリル酸メチル－スチレン共重合体、アクリロニトリル－スチレン－メタクリル酸メチル共重合体、ポリアセタール樹脂、変性ポリフェニレンエーテル樹脂、エチレン－酢酸ビニル共重合体、ポリフェニレンスルフィド樹脂、ポリフェニルスルホン、ポリエーテルケトン、ポリエーテルエーテルケトン、ポリエーテル、シクロオレフィンポリマー、液晶ポリエステル樹脂、液晶ポリマー、ポリアミド、フッ素樹脂、ポリビニルピロリドン、天然ゴム、ブチルゴム、ポリイソブチレン、ポリサルファイドなどを挙げることができる。
Examples of thermoplastic resins include styrene resins, acrylic resins, vinyl acetate resins, acrylonitrile copolymers, polyphenylene oxide resins, polysulfone resins, polyethersulfones, polyarylates, polyetherimides, polyamideimides, polyimides, and polymethacrylic acid. Methyl, acrylonitrile-styrene copolymer resin, acrylonitrile-styrene-N-substituted maleimide terpolymer, acrylonitrile-butadiene-styrene copolymer resin, styrene-maleic anhydride copolymer resin, styrene-maleic anhydride- N-substituted maleimide copolymer resin, polycarbonate resin, polybutylene terephthalate resin, polyethylene (linear low density polyethylene, low density polyethylene, high density polyethylene, etc.), polyethylene terephthalate, polybutylene terephthalate, polyvinyl chloride, polypropylene, styrene -butadiene-styrene block copolymer and hydrogenated products thereof, styrene-butadiene rubber, acrylonitrile-butadiene rubber, polybutadiene, polyisoprene, styrene-isoprene-styrene block copolymer and hydrogenated products thereof, polyolefin elastomer, polyester Elastomer, polystyrene, acrylic resin, methyl methacrylate-styrene copolymer, acrylonitrile-styrene-methyl methacrylate copolymer, polyacetal resin, modified polyphenylene ether resin, ethylene-vinyl acetate copolymer, polyphenylene sulfide resin, polyphenylsulfone , polyether ketone, polyether ether ketone, polyether, cycloolefin polymer, liquid crystal polyester resin, liquid crystal polymer, polyamide, fluororesin, polyvinylpyrrolidone, natural rubber, butyl rubber, polyisobutylene, polysulfide, and the like.
熱硬化性樹脂は、加熱することによって、重合反応若しくは架橋反応が進行して、硬化するものである。熱硬化性樹脂としては、フェノール樹脂、エポキシ樹脂、メラミン樹脂、ユリア樹脂、不飽和ポリエステル樹脂、アルキド樹脂、ポリウレタン、熱硬化性ポリイミド、ジアリルフタレート樹脂などを挙げることができる。熱硬化性樹脂は、熱可塑性樹脂に、加硫剤、硬化剤または架橋剤を配合してなるものであってもよい。
Thermosetting resins are those that are hardened by the progress of a polymerization reaction or a cross-linking reaction when heated. Examples of thermosetting resins include phenol resins, epoxy resins, melamine resins, urea resins, unsaturated polyester resins, alkyd resins, polyurethanes, thermosetting polyimides, and diallyl phthalate resins. The thermosetting resin may be a thermoplastic resin mixed with a vulcanizing agent, a curing agent, or a cross-linking agent.
光硬化性樹脂は、紫外線などの光を照射することによって、重合反応若しくは架橋反応が進行して、硬化するものである。例えば、光ラジカル発生剤、光カチオン発生剤、光酸発生剤、光塩基発生剤などの光開始剤を所望のモノマーまたはオリゴマーに配合してなるものである。光硬化性樹脂に用い得るモノマーまたはオリゴマーは特に制限されず、（メタ）アクリレートモノマー、（メタ）アクリレートオリゴマー、ビスフェノールＡジグリシジルエーテル、水添ビスフェノールＡジグリシジルエーテル、ビスフェノールＦジグリシジルエーテル、シクロヘキサンジメタノールジグリシジルエーテル３，４－エポキシシクロヘキシルメチル－３’，４’－エポキシシクロヘキサンカルボキシレート、２，２－ビス（ヒドロキシメチル）－１－ブタノールの１，２－エポキシ－４－（２－オキシラニル）シクロヘキサン付加物； キシリレンビスオキセタン、３－エチル－３－ヒドロキシメチルオキセタンなどのオキセタン化合物； シクロヘキサンジメタノールジビニルエーテル、２－エチルヘキシルビニルエーテル、シクロヘキサンジメタノールモノビニルエーテル、４－ヒドロキシブチルビニルエーテルなどのビニルエーテルモノマーなどを挙げることができる。
A photocurable resin is a resin that is cured by a polymerization reaction or a cross-linking reaction when irradiated with light such as ultraviolet rays. For example, a desired monomer or oligomer is blended with a photoinitiator such as a photoradical generator, photocation generator, photoacid generator, or photobase generator. Monomers or oligomers that can be used in the photocurable resin are not particularly limited, and include (meth)acrylate monomers, (meth)acrylate oligomers, bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, cyclohexane di Methanol diglycidyl ether 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexanecarboxylate, 1,2-epoxy-4-(2-oxiranyl) of 2,2-bis(hydroxymethyl)-1-butanol Cyclohexane adducts; Oxetane compounds such as xylylene bisoxetane and 3-ethyl-3-hydroxymethyloxetane; Vinyl ether monomers such as cyclohexanedimethanol divinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovinyl ether, 4-hydroxybutyl vinyl ether, etc. can be mentioned.
その他の樹脂として、シリコーン、アクリルシリコーン、変性シリコーン、漆、膠、石油樹脂、水添石油樹脂； 米・小麦・トウモロコシ・ジャガイモ、サツマイモ、タピオカなどの澱粉およびその他の天然物またはそれらなどを原料とした生分解性プラスチックなどを挙げることができる。
Other resins include silicone, acrylic silicone, modified silicone, lacquer, glue, petroleum resin, and hydrogenated petroleum resin; starches such as rice, wheat, corn, potato, sweet potato, tapioca, and other natural products, or those made from and biodegradable plastics.
本発明の樹脂組成物に含有する樹脂の量は、用途に応じて適宜設定することができ、例えば、樹脂組成物１００質量部に対して、好ましくは５～９９質量部、より好ましくは３０～９５質量部、さらに好ましくは５０～９０質量部である。
The amount of the resin contained in the resin composition of the present invention can be appropriately set according to the application. 95 parts by mass, more preferably 50 to 90 parts by mass.
本発明の樹脂組成物は、製造方法によって、特に制限されない。例えば、イミノクタジン化合物若しくは本発明の抗ウイルス剤組成物と、樹脂と、必要に応じて公知の樹脂用添加剤とを、公知の方法で混ぜ合わせることによって、得ることができる。樹脂用添加剤としては、酸化防止剤、熱劣化防止剤、光安定剤、滑剤、離型剤、高分子加工助剤、帯電防止剤、難燃剤、染顔料、光拡散剤、有機色素、艶消し剤、耐衝撃性改質剤、蛍光体、フィラー、防腐剤、防藻剤、顔料分散剤、可塑剤、乾燥促進剤、界面活性剤、消泡剤、皮張り防止剤、低温造膜剤、造膜助剤、増粘剤、レベリング剤、分散剤、沈降防止剤、硬化剤、硬化助剤、凍結防止剤などを挙げることができる。
The resin composition of the present invention is not particularly limited by the manufacturing method. For example, it can be obtained by mixing an iminoctadine compound or the antiviral agent composition of the present invention, a resin, and, if necessary, a known resin additive by a known method. Additives for resins include antioxidants, heat deterioration inhibitors, light stabilizers, lubricants, release agents, polymer processing aids, antistatic agents, flame retardants, dyes and pigments, light diffusing agents, organic pigments, gloss Erasing agents, impact modifiers, phosphors, fillers, preservatives, anti-algae agents, pigment dispersants, plasticizers, drying accelerators, surfactants, anti-foaming agents, anti-skinning agents, low-temperature film-forming agents , film-forming aids, thickeners, leveling agents, dispersants, anti-settling agents, curing agents, curing aids, anti-freezing agents, and the like.
イミノクタジン化合物若しくは本発明の抗ウイルス剤組成物と、樹脂と、必要に応じて用いる公知の樹脂用添加剤との混合は、例えば、ニーダールーダー、単軸または多軸押出機、ミキシングロール、バンバリーミキサーなどの公知の混合装置または混練装置を使用して行なうことができる。硬化前の液状の熱硬化性樹脂や光硬化性樹脂は、タンクブレンドによって、イミノクタジン化合物若しくは本発明の抗ウイルス剤組成物および必要に応じて用いる公知の樹脂用添加剤と混ぜ合わせることができる。
Mixing of the iminoctadine compound or the antiviral agent composition of the present invention, a resin, and known additives for resins that are optionally used can be carried out using, for example, a kneader-ruder, a single-screw or multi-screw extruder, a mixing roll, and a Banbury mixer. It can be carried out using a known mixing device or kneading device such as. The liquid thermosetting resin or photocurable resin before curing can be mixed with the iminoctadine compound or the antiviral agent composition of the present invention and known resin additives used as necessary by tank blending.
本発明の樹脂組成物は、公知の成形法によって所望の形状にすることができる。また、液体状の本発明の樹脂組成物は、他の材料に、添加、塗布、噴霧、含浸させることができる。固体状の本発明の樹脂組成物は、他の材料に、混合、付着させることができる。
The resin composition of the present invention can be made into a desired shape by a known molding method. Further, the liquid resin composition of the present invention can be added, applied, sprayed, or impregnated into other materials. The solid resin composition of the present invention can be mixed and adhered to other materials.
本発明の成形体は、本発明の樹脂組成物を含有して成るものである。本発明の成形体は、本発明の樹脂組成物を公知の成形法によって所望の形状にすることによって得ることができる。成形法としては、押出成形法、射出成形法、圧縮成形法、ブロー成形法、キャスト成形法、積層成形法、積層造形法、粉体成形法などを挙げることができる。
The molded article of the present invention contains the resin composition of the present invention. The molded article of the present invention can be obtained by shaping the resin composition of the present invention into a desired shape by a known molding method. Examples of molding methods include extrusion molding, injection molding, compression molding, blow molding, cast molding, lamination molding, lamination molding, and powder molding.
本発明の被覆用組成物、接着剤組成物または塗料組成物は、イミノクタジン化合物を含有するものである。
The coating composition, adhesive composition or coating composition of the present invention contains an iminoctadine compound.
本発明の被覆用組成物、接着剤組成物または塗料組成物に含有するイミノクタジン化合物の量は、用途に応じて適宜設定することができ、例えば、被覆用組成物、接着剤組成物または塗料組成物１００質量部に対して、好ましくは０．０００１～７０質量部、より好ましくは０．０００５～４０質量部、さらに好ましくは０．００１～２０質量部、特に好ましくは０．００１～５質量部である。
The amount of the iminoctazine compound contained in the coating composition, adhesive composition or coating composition of the present invention can be appropriately set depending on the application. Preferably 0.0001 to 70 parts by mass, more preferably 0.0005 to 40 parts by mass, still more preferably 0.001 to 20 parts by mass, particularly preferably 0.001 to 5 parts by mass based on 100 parts by mass of the substance is.
本発明の被覆用組成物、接着剤組成物または塗料組成物は、イミノクタジン化合物以外に、公知の被覆用組成物、接着剤組成物または塗料組成物に含めることができる成分（例えば、樹脂、溶媒、添加剤など）を含有することができる。該成分は、それぞれの組成物に、被覆材、接着剤または塗料に適する特性を付与するものであることができる。特性としては、流動性、粘着性、塗布性、成膜性、積層性、耐ブリスタ性、密着性、接着性、封止性、装飾性などを挙げることができる。このような特性は、使用する樹脂の種類や量、溶媒の種類や量、添加剤の種類や量などを、適宜、選定することによって、実現できる。
The coating composition, adhesive composition, or coating composition of the present invention contains, in addition to the iminoctadine compound, components that can be included in known coating compositions, adhesive compositions, or coating compositions (e.g., resins, solvents, , additives, etc.). The components can impart to the respective composition properties suitable for coatings, adhesives or paints. Properties include fluidity, adhesiveness, coatability, film-forming properties, lamination properties, blister resistance, adhesion, adhesiveness, sealing properties, decorative properties, and the like. Such characteristics can be realized by appropriately selecting the type and amount of resin to be used, the type and amount of solvent, the type and amount of additive, and the like.
本発明の液体状の被覆用組成物は、基材の上に、刷毛塗り、ロールコート、バーコート、スプレーコートなどの塗布法によって、載せて、次いで、乾燥させ、必要に応じて硬化させることによって、基材を被覆することができる。
本発明の固体状の被覆用組成物は、基材の上に、粉散布、シート掛け、フィルム掛けなどによって、載せて、圧着、融着若しくは接着することによって、基材を被覆することができる。 The liquid coating composition of the present invention is applied onto a substrate by a coating method such as brush coating, roll coating, bar coating, or spray coating, and then dried and, if necessary, cured. The substrate can be coated by
The solid coating composition of the present invention can be placed on a substrate by dusting, sheeting, filming, or the like, and the substrate can be coated by pressing, fusing or adhering. .
本発明の固体状の被覆用組成物は、基材の上に、粉散布、シート掛け、フィルム掛けなどによって、載せて、圧着、融着若しくは接着することによって、基材を被覆することができる。 The liquid coating composition of the present invention is applied onto a substrate by a coating method such as brush coating, roll coating, bar coating, or spray coating, and then dried and, if necessary, cured. The substrate can be coated by
The solid coating composition of the present invention can be placed on a substrate by dusting, sheeting, filming, or the like, and the substrate can be coated by pressing, fusing or adhering. .
本発明の抗ウイルス剤組成物、樹脂組成物、被覆用組成物、接着剤組成物、または塗料組成物は、種々の用途に、利用することができる。例えば、浴室の内装材、フロアマット、壁用シート、壁紙、障子紙、床材、手すり材、天井材、不燃木材、シーリング剤、コーキング剤、封止剤、接着剤（アクリル系、オレフィン系、ウレタン系、エポキシ系、天然系）、塗料（油性塗料、酒精塗料、ＮＡＤ塗料、電着塗料、粉体塗料、セルロース塗料、合成樹脂塗料、水性塗料、漆系塗料、ゴム系塗料、ウレタン系塗料、シリコーン系塗料など）、 集成材、化粧合板およびその他の木質材、合成木材、疑似木材、再生木材、断熱材、遮熱材、石膏ボード、その他の建材； フィルム、シート； 樹脂系サイディング、窯業系サイディング、タイル、ひさし材、屋根材、外壁材等の建築物の外装材； 澱粉糊、紙用塗工液、塗料、接着剤、補修剤、セラミック材料、セメント混和剤、金属加工油;
織布、不織布などを挙げることができる。 The antiviral agent composition, resin composition, coating composition, adhesive composition, or coating composition of the present invention can be used for various purposes. For example, bathroom interior materials, floor mats, wall sheets, wallpaper, shoji paper, floor materials, handrail materials, ceiling materials, incombustible wood, sealants, caulking agents, sealing agents, adhesives (acrylic, olefin, Urethane, epoxy, natural), paint (oil paint, alcohol paint, NAD paint, electrodeposition paint, powder paint, cellulose paint, synthetic resin paint, water-based paint, lacquer paint, rubber paint, urethane paint , silicone paint, etc.), laminated wood, decorative plywood and other wood materials, synthetic wood, simulated wood, recycled wood, heat insulating materials, heat shielding materials, gypsum boards, other building materials; films, sheets; resin-based siding, ceramics Exterior materials for buildings such as siding, tiles, eaves, roofing, and exterior wall materials; Starch paste, paper coating liquid, paint, adhesive, repair agent, ceramic material, cement admixture, metalworking oil;
A woven fabric, a nonwoven fabric, etc. can be mentioned.
織布、不織布などを挙げることができる。 The antiviral agent composition, resin composition, coating composition, adhesive composition, or coating composition of the present invention can be used for various purposes. For example, bathroom interior materials, floor mats, wall sheets, wallpaper, shoji paper, floor materials, handrail materials, ceiling materials, incombustible wood, sealants, caulking agents, sealing agents, adhesives (acrylic, olefin, Urethane, epoxy, natural), paint (oil paint, alcohol paint, NAD paint, electrodeposition paint, powder paint, cellulose paint, synthetic resin paint, water-based paint, lacquer paint, rubber paint, urethane paint , silicone paint, etc.), laminated wood, decorative plywood and other wood materials, synthetic wood, simulated wood, recycled wood, heat insulating materials, heat shielding materials, gypsum boards, other building materials; films, sheets; resin-based siding, ceramics Exterior materials for buildings such as siding, tiles, eaves, roofing, and exterior wall materials; Starch paste, paper coating liquid, paint, adhesive, repair agent, ceramic material, cement admixture, metalworking oil;
A woven fabric, a nonwoven fabric, etc. can be mentioned.
合成樹脂塗料としては、フェノール樹脂塗料、フタル酸樹脂塗料（例えば、アルキド樹脂塗料など）、マレイン酸樹脂塗料、尿素樹脂塗料、メラミン樹脂塗料、ビニル樹脂塗料（例えば、酢酸ビニル樹脂塗料、塩化ビニル樹脂塗料、スチレン樹脂塗料、アクリル酸樹脂塗料、ポリビニルブチラール樹脂塗料など）、エポキシ樹脂塗料、シリコーン樹脂塗料、フラン樹脂塗料、ポリエステル樹脂塗料、ウレタン樹脂塗料、ニトロセルロース樹脂塗料、アミノ樹脂塗料、フッ素樹脂塗料などを挙げることができる。
Synthetic resin paints include phenol resin paints, phthalate resin paints (e.g. alkyd resin paints), maleic acid resin paints, urea resin paints, melamine resin paints, vinyl resin paints (e.g. vinyl acetate resin paints, vinyl chloride resin paints). paint, styrene resin paint, acrylic acid resin paint, polyvinyl butyral resin paint, etc.), epoxy resin paint, silicone resin paint, furan resin paint, polyester resin paint, urethane resin paint, nitrocellulose resin paint, amino resin paint, fluorine resin paint etc. can be mentioned.
水性塗料としては、水性ペイント、エマルション油ペイント、乳化重合塗料（例えば、酢酸ビニル樹脂乳化重合塗料、塩化ビニリデン塩化ビニル共重合体乳化重合塗料、アクリル酸樹脂乳化重合塗料、スチレン樹脂乳化重合塗料、合成ゴムラテックス塗料など）などを挙げることができる。
Water-based paints include water-based paints, emulsion oil paints, emulsion polymerization paints (for example, vinyl acetate resin emulsion polymerization paints, vinylidene chloride vinyl chloride copolymer emulsion polymerization paints, acrylic acid resin emulsion polymerization paints, styrene resin emulsion polymerization paints, synthetic rubber latex paint, etc.).
本発明の樹脂組成物、被覆用組成物、または塗料組成物は、カップリング剤をさらに含有することができる。カップリング剤は、性質の異なる材料、主には無機材料と有機材料を結合させる化合物である。カップリング剤としては、シランカップリング剤、チタネート系カップリング剤、アルミネート系カップリング剤、ジルコネート系カップリング剤などを挙げることができる。
シランカップリング剤としては、２－（３，４－エポキシシクロヘキシル）エチルトリメトキシシラン、３－グリシドキシプロピルメチルジメトキシシラン、３－グリシドキシプロピルトリメトキシシラン、３－グリシドキシプロピルメチルジエトキシシラン、３－グリシドキシプロピルトリエトキシシラン、３－メタクリロキシプロピルメチルジメトキシシラン、３－メタクリロキシプロピルトリメトキシシラン、３－メタクリロキシプロピルメチルジエトキシシラン、３－メタクリロキシプロピルトリエトキシシラン等を挙げることができる。 The resin composition, coating composition, or coating composition of the present invention can further contain a coupling agent. A coupling agent is a compound that bonds materials with different properties, mainly inorganic and organic materials. Examples of coupling agents include silane coupling agents, titanate coupling agents, aluminate coupling agents, and zirconate coupling agents.
Silane coupling agents include 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane. ethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, etc. can be mentioned.
シランカップリング剤としては、２－（３，４－エポキシシクロヘキシル）エチルトリメトキシシラン、３－グリシドキシプロピルメチルジメトキシシラン、３－グリシドキシプロピルトリメトキシシラン、３－グリシドキシプロピルメチルジエトキシシラン、３－グリシドキシプロピルトリエトキシシラン、３－メタクリロキシプロピルメチルジメトキシシラン、３－メタクリロキシプロピルトリメトキシシラン、３－メタクリロキシプロピルメチルジエトキシシラン、３－メタクリロキシプロピルトリエトキシシラン等を挙げることができる。 The resin composition, coating composition, or coating composition of the present invention can further contain a coupling agent. A coupling agent is a compound that bonds materials with different properties, mainly inorganic and organic materials. Examples of coupling agents include silane coupling agents, titanate coupling agents, aluminate coupling agents, and zirconate coupling agents.
Silane coupling agents include 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane. ethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, etc. can be mentioned.
チタネート系カップリング剤としては、テトライソプロピルチタネート、テトラ－ｎ－ブチルチタネート、テトラキス（２－エチルヘキシルオキシ）チタン、チタニウム－ｉ－プロポキシオクチレングリコレート等のチタンアルコキシド；チタンアセチルアセトナート、チタンテトラアセチルアセトナート、ジ－ｉ－プロポキシ・ビス（アセチルアセトナート）チタン、ジ－ｎ－プロポキシ・ビス（アセチルアセトナート）チタン、ジ－ｎ－ブトキシ・ビス（アセチルアセトナート）チタン、ジエトキシ・ビス（アセチルアセトナート）チタン、プロパンジオキシチタンビス（エチルアセトアセテート）等のチタン錯体等が挙げられる。
Titanate-based coupling agents include titanium alkoxides such as tetraisopropyl titanate, tetra-n-butyl titanate, tetrakis(2-ethylhexyloxy)titanium, titanium-i-propoxyoctylene glycolate; titanium acetylacetonate, titanium tetraacetyl Acetonate, di-i-propoxy bis(acetylacetonato)titanium, di-n-propoxy bis(acetylacetonato)titanium, di-n-butoxy bis(acetylacetonato)titanium, diethoxy bis(acetyl acetonate), titanium complexes such as propanedioxytitanium bis(ethylacetoacetate), and the like.
アルミネート系カップリング剤としては、例えば、アルミニウムイソプロピレート、モノ－ｓｅｃ－ブトキシアルミニウムジイソプロピレート、アルミニウムエチレート等のアルミニウムアルコレート；エチルアセトアセテートアルミニウムジイソプロピレート、アルミニウムビスエチルアセトアセテート・モノアセチルアセトナート、アルミニウムトリス（エチルアセトアセテート）、アルミニウムトリス（アセチルアセトナート）、ジエトキシモノ（アセチルアセトナート）アルミニウム、ジ－ｉ－プロポキシモノ（アセチルアセトナート）アルミニウム、ジ－ｎ－プロポキシモノ（アセチルアセトナート）アルミニウム、ジ－ｎ－ブトキシモノ（アセチルアセトナート）アルミニウム、エトキシビス（アセチルアセトナート）アルミニウム、ｉ－プロポキシビス（アセチルアセトナート）アルミニウム、ｎ－プロポキシビス（アセチルアセトナート）アルミニウム、ｎ－ブトキシビス（アセチルアセトナート）アルミニウム等のアルミニウム錯体；環状アルミニウムオリゴマー等が挙げられる。
Examples of aluminate-based coupling agents include aluminum alcoholates such as aluminum isopropylate, mono-sec-butoxyaluminum diisopropylate, and aluminum ethylate; ethylacetoacetate aluminum diisopropylate, aluminum bisethylacetoacetate/monoacetyl Acetonate, aluminum tris (ethylacetoacetate), aluminum tris (acetylacetonate), diethoxy mono (acetylacetonate) aluminum, di-i-propoxy mono (acetylacetonate) aluminum, di-n-propoxy mono (acetylacetonate) ) aluminum, di-n-butoxymono(acetylacetonato)aluminum, ethoxybis(acetylacetonato)aluminum, i-propoxybis(acetylacetonato)aluminum, n-propoxybis(acetylacetonato)aluminum, n-butoxybis(acetyl acetonate), aluminum complexes such as aluminum; cyclic aluminum oligomers, and the like.
ジルコネート系カップリング剤としては、ジルコニウムテトラキス（アセチルアセトナート）、ジ－ｎ－ブトキシビス（アセチルアセトナート）ジルコニウム、ジルコニウムテトラキス（エチルアセトアセテート）、ジエトキシビスアセチルアセトナートジルコニウム、ジ－ｉ－プロポキシビス（アセチルアセトナート）ジルコニウム、ジ－ｎ－プロポキシビス（アセチルアセトナート）ジルコニウム、トリ－ｎ－ブトキシモノエチルアセトアセテートジルコニウム、トリ－ｎ－ブトキシモノアセチルアセトナートジルコニウム等が挙げられる。
Zirconate-based coupling agents include zirconium tetrakis (acetylacetonate), di-n-butoxybis (acetylacetonate) zirconium, zirconium tetrakis (ethylacetoacetate), diethoxybis acetylacetonate zirconium, and di-i-propoxybis. (acetylacetonato)zirconium, di-n-propoxybis(acetylacetonato)zirconium, tri-n-butoxymonoethylacetoacetatezirconium, tri-n-butoxymonoacetylacetonatozirconium and the like.
本発明の樹脂組成物、被覆用組成物、または塗料組成物は、更にフィラーを含有することができる。フィラーとしては、カーボンブラック、グラフェン、カーボンナノチューブ、ガラス繊維、酸化鉄、バライト、タルク、炭酸カルシウム、カオリン、クレー、シリカ、二酸化チタン、アルミナ、ジルコニア、シリコーン樹脂微粒子、フッ素樹脂微粒子、アクリル樹脂微粒子、ウレタン系樹脂微粒子、シリコーン変性ウレタン系樹脂微粒子、ポリエチレン微粒子、ポリカーボネート系樹脂微粒子などを挙げることができる。
The resin composition, coating composition, or coating composition of the present invention may further contain a filler. Fillers include carbon black, graphene, carbon nanotube, glass fiber, iron oxide, barite, talc, calcium carbonate, kaolin, clay, silica, titanium dioxide, alumina, zirconia, silicone resin fine particles, fluororesin fine particles, acrylic resin fine particles, Examples include urethane-based resin fine particles, silicone-modified urethane-based resin fine particles, polyethylene fine particles, and polycarbonate-based resin fine particles.
本発明の積層体は、基材と、それに積層された本発明の樹脂組成物、被覆用組成物、接着剤組成物または塗料組成物からなる層とを有するものである。
本発明に用い得る基材は、特に限定されない。基材としては、例えば、建築物全般、建築資材、金属、ゴム、木質材、プラスチック製品、繊維、布、紙、セラミクス、コンクリート、ブロック、レンガなどを挙げることができる。本発明の樹脂組成物、被覆用組成物、接着剤組成物または塗料組成物からなる層は、色調が経日変化し難いので外観を損なわず、且つ優れた抗ウイルス性を示す。基材への積層は、公知の方法で行うことができる。例えば、多色押出成形法、被覆押出成形法、接着法、融着法、塗布法、噴霧法、粉体成形法、インモールド成形法、フィルムインサート成形法などを挙げることができる。 The laminate of the present invention comprises a substrate and a layer of the resin composition, coating composition, adhesive composition or coating composition of the present invention laminated thereon.
Substrates that can be used in the present invention are not particularly limited. Examples of base materials include buildings in general, building materials, metals, rubbers, wood materials, plastic products, fibers, cloth, paper, ceramics, concrete, blocks, and bricks. A layer composed of the resin composition, coating composition, adhesive composition, or coating composition of the present invention does not impair the appearance because the color tone does not easily change over time, and exhibits excellent antiviral properties. Lamination on the substrate can be performed by a known method. For example, multicolor extrusion molding, coated extrusion molding, adhesion, fusion bonding, coating, spraying, powder molding, in-mold molding, film insert molding and the like can be mentioned.
本発明に用い得る基材は、特に限定されない。基材としては、例えば、建築物全般、建築資材、金属、ゴム、木質材、プラスチック製品、繊維、布、紙、セラミクス、コンクリート、ブロック、レンガなどを挙げることができる。本発明の樹脂組成物、被覆用組成物、接着剤組成物または塗料組成物からなる層は、色調が経日変化し難いので外観を損なわず、且つ優れた抗ウイルス性を示す。基材への積層は、公知の方法で行うことができる。例えば、多色押出成形法、被覆押出成形法、接着法、融着法、塗布法、噴霧法、粉体成形法、インモールド成形法、フィルムインサート成形法などを挙げることができる。 The laminate of the present invention comprises a substrate and a layer of the resin composition, coating composition, adhesive composition or coating composition of the present invention laminated thereon.
Substrates that can be used in the present invention are not particularly limited. Examples of base materials include buildings in general, building materials, metals, rubbers, wood materials, plastic products, fibers, cloth, paper, ceramics, concrete, blocks, and bricks. A layer composed of the resin composition, coating composition, adhesive composition, or coating composition of the present invention does not impair the appearance because the color tone does not easily change over time, and exhibits excellent antiviral properties. Lamination on the substrate can be performed by a known method. For example, multicolor extrusion molding, coated extrusion molding, adhesion, fusion bonding, coating, spraying, powder molding, in-mold molding, film insert molding and the like can be mentioned.
本発明の実施形態を以下の実施例に基づいて説明する。ただし、本発明は、これら実施例によって制限されるものでない。
Embodiments of the present invention will be described based on the following examples. However, the present invention is not limited by these examples.
実施例１
エチレングリコールモノｎ－ブチルエーテル８２．７３質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し溶解させた。これにイミノクタジンアルベシル酸塩水和剤（ベルクート（登録商標）フロアブル；イミノクタジンアルベシル酸塩３０％含有）３．３３質量部（イミノクタジンアルベシル酸塩として１質量部）を添加し、混合することにより液状の組成物Ａを得た。 Example 1
82.73 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved. 3.33 parts by mass of iminoctadine albesilate wettable powder (Berkut (registered trademark) flowable; containing 30% iminoctadine albesilate) (1 part by mass as iminoctadine albesilate) is added to this and mixed. A liquid composition A was obtained.
エチレングリコールモノｎ－ブチルエーテル８２．７３質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し溶解させた。これにイミノクタジンアルベシル酸塩水和剤（ベルクート（登録商標）フロアブル；イミノクタジンアルベシル酸塩３０％含有）３．３３質量部（イミノクタジンアルベシル酸塩として１質量部）を添加し、混合することにより液状の組成物Ａを得た。 Example 1
82.73 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved. 3.33 parts by mass of iminoctadine albesilate wettable powder (Berkut (registered trademark) flowable; containing 30% iminoctadine albesilate) (1 part by mass as iminoctadine albesilate) is added to this and mixed. A liquid composition A was obtained.
自動塗工装置（ＰＩ－１２１０：テスター産業社製）を用いて、１４８ｍｍ×２１０ｍｍのポリエチレンテレフタレートフィルム（ルミラー(Ｒ)フィルム（T60透明）２５０μｍ）の片側全面に、組成物Ａを約３ｍＬ塗布した。その後、１００℃の恒温槽に入れ２０分間乾燥させた。次いで、紫外線硬化用光源装置（アイグラフィックス社製）を用いて乾燥塗膜を硬化させ、ポリエチレンテレフタレートフィルムと組成物Ａの不揮発成分からなる膜とが積層されてなる積層体を得た。
About 3 mL of composition A was applied to one side of a polyethylene terephthalate film (Lumirror (R) film (T60 transparent) 250 μm) of 148 mm × 210 mm using an automatic coating device (PI-1210: manufactured by Tester Sangyo Co., Ltd.). . After that, it was placed in a constant temperature bath at 100° C. and dried for 20 minutes. Next, the dried coating film was cured using an ultraviolet curing light source device (manufactured by Eyegraphics Co., Ltd.) to obtain a laminate in which a polyethylene terephthalate film and a film composed of non-volatile components of composition A were laminated.
（バクテリオファージＱβを用いた抗ウイルス性評価）
切り出された５０ｍｍ四方の積層体をシャーレに入れ、積層体の組成物Ａからなる膜（抗ウイルス層）の上に、バクテリオファージＱβ含有液０．１ｍＬを載せ、その上に４０ｍｍ四方のポリプロピレンフィルムを被せて、評価対象とポリプロピレンフィルムとの間にバクテリオファージＱβ含有液を展開させた。シャーレに蓋をした。シャーレを約２５℃の暗所に４時間放置した。その後、積層体をＳＣＤＬＰブイヨン培地（栄研化学社製）１０ｍＬに浸漬した。
次に、培地をサンプリングし、ＳＭ緩衝液（成分＝ 蒸留水、濃度0.1M NaCl、濃度8mM MgSO4・7H2O、濃度50mM Tris-HCl（pH＝7.5）、濃度0.01％ ゼラチン）により希釈した。得られた希釈液１ｍＬに大腸菌培養液０．１５ｍＬを加え、３７℃で２４時間培養した。プラーク数を目視にて計測し、感染価Ｔを算出した。
なお、感染価は、下記の式で定義される値である。
感染価 ＝ プラーク数 × 希釈倍率 (Antiviral evaluation using bacteriophage Qβ)
Put the cut-out 50 mm square laminate in a petri dish, place 0.1 mL of a bacteriophage Qβ-containing solution on the film (antiviral layer) made of composition A of the laminate, and place a 40 mm square polypropylene film thereon. was covered, and a bacteriophage Qβ-containing liquid was developed between the object to be evaluated and the polypropylene film. I put a lid on the petri dish. The petri dish was left in a dark place at about 25°C for 4 hours. After that, the laminate was immersed in 10 mL of SCDLP bouillon medium (manufactured by Eiken Chemical Co., Ltd.).
Next, the medium was sampled and diluted with SM buffer (Components = distilled water, concentration 0.1 M NaCl, concentration 8 mM MgSO4.7H2O , concentration 50 mM Tris-HCl (pH = 7.5), concentration 0.01% gelatin). . 0.15 mL of E. coli culture was added to 1 mL of the obtained diluted solution, and cultured at 37° C. for 24 hours. The number of plaques was visually counted, and the infectious titer T was calculated.
The infectivity titer is a value defined by the following formula.
Infectious titer = number of plaques × dilution factor
切り出された５０ｍｍ四方の積層体をシャーレに入れ、積層体の組成物Ａからなる膜（抗ウイルス層）の上に、バクテリオファージＱβ含有液０．１ｍＬを載せ、その上に４０ｍｍ四方のポリプロピレンフィルムを被せて、評価対象とポリプロピレンフィルムとの間にバクテリオファージＱβ含有液を展開させた。シャーレに蓋をした。シャーレを約２５℃の暗所に４時間放置した。その後、積層体をＳＣＤＬＰブイヨン培地（栄研化学社製）１０ｍＬに浸漬した。
次に、培地をサンプリングし、ＳＭ緩衝液（成分＝ 蒸留水、濃度0.1M NaCl、濃度8mM MgSO4・7H2O、濃度50mM Tris-HCl（pH＝7.5）、濃度0.01％ ゼラチン）により希釈した。得られた希釈液１ｍＬに大腸菌培養液０．１５ｍＬを加え、３７℃で２４時間培養した。プラーク数を目視にて計測し、感染価Ｔを算出した。
なお、感染価は、下記の式で定義される値である。
感染価 ＝ プラーク数 × 希釈倍率 (Antiviral evaluation using bacteriophage Qβ)
Put the cut-out 50 mm square laminate in a petri dish, place 0.1 mL of a bacteriophage Qβ-containing solution on the film (antiviral layer) made of composition A of the laminate, and place a 40 mm square polypropylene film thereon. was covered, and a bacteriophage Qβ-containing liquid was developed between the object to be evaluated and the polypropylene film. I put a lid on the petri dish. The petri dish was left in a dark place at about 25°C for 4 hours. After that, the laminate was immersed in 10 mL of SCDLP bouillon medium (manufactured by Eiken Chemical Co., Ltd.).
Next, the medium was sampled and diluted with SM buffer (Components = distilled water, concentration 0.1 M NaCl, concentration 8 mM MgSO4.7H2O , concentration 50 mM Tris-HCl (pH = 7.5), concentration 0.01% gelatin). . 0.15 mL of E. coli culture was added to 1 mL of the obtained diluted solution, and cultured at 37° C. for 24 hours. The number of plaques was visually counted, and the infectious titer T was calculated.
The infectivity titer is a value defined by the following formula.
Infectious titer = number of plaques × dilution factor
積層体の代わりにガラス板を用いて上記と同じ方法で感染価Ｕを算出した。算出された感染価Ｔと感染価Ｕから、抗ウイルス活性値を算出した。
なお、抗ウイルス活性値は、下記の式で定義される値である。
抗ウイルス活性値 ＝ Ｌｏｇ（感染価Ｕ）－Ｌｏｇ（感染価Ｔ）
バクテリオファージＱβに対する抗ウイルス活性値は４．８であった。 Using a glass plate instead of the laminate, the infectivity titer U was calculated in the same manner as above. From the calculated infectious titer T and infectious titer U, the antiviral activity value was calculated.
The antiviral activity value is a value defined by the following formula.
Antiviral activity value = Log (infectious value U) - Log (infectious value T)
The antiviral activity value against bacteriophage Qβ was 4.8.
なお、抗ウイルス活性値は、下記の式で定義される値である。
抗ウイルス活性値 ＝ Ｌｏｇ（感染価Ｕ）－Ｌｏｇ（感染価Ｔ）
バクテリオファージＱβに対する抗ウイルス活性値は４．８であった。 Using a glass plate instead of the laminate, the infectivity titer U was calculated in the same manner as above. From the calculated infectious titer T and infectious titer U, the antiviral activity value was calculated.
The antiviral activity value is a value defined by the following formula.
Antiviral activity value = Log (infectious value U) - Log (infectious value T)
The antiviral activity value against bacteriophage Qβ was 4.8.
（バクテリオファージφ６を用いた抗ウイルス性評価）
バクテリオファージＱβ含有液の代わりにバクテリオファージφ６含有液を用い、大腸菌培養液の代わりにPseudomonas syringae培養液を用いた以外は上記と同じ方法で抗ウイルス活性値を算出した。
バクテリオファージφ６に対する抗ウイルス活性値は５．２であった。 (Antiviral evaluation using bacteriophage φ6)
The antiviral activity value was calculated in the same manner as described above, except that the bacteriophage φ6-containing solution was used instead of the bacteriophage Qβ-containing solution, and the Pseudomonas syringae culture solution was used instead of the E. coli culture solution.
The antiviral activity value against bacteriophage φ6 was 5.2.
バクテリオファージＱβ含有液の代わりにバクテリオファージφ６含有液を用い、大腸菌培養液の代わりにPseudomonas syringae培養液を用いた以外は上記と同じ方法で抗ウイルス活性値を算出した。
バクテリオファージφ６に対する抗ウイルス活性値は５．２であった。 (Antiviral evaluation using bacteriophage φ6)
The antiviral activity value was calculated in the same manner as described above, except that the bacteriophage φ6-containing solution was used instead of the bacteriophage Qβ-containing solution, and the Pseudomonas syringae culture solution was used instead of the E. coli culture solution.
The antiviral activity value against bacteriophage φ6 was 5.2.
〔実施例２〕
エチレングリコールモノｎ－ブチルエーテル８３．５６質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し溶解させた。これにイミノクタジン酢酸塩製剤（べフラン原体４０（日本曹達社製）：イミノクタジン酢酸塩４０％含有）２．５０質量部（イミノクタジン酢酸塩として１質量部）を添加し、混合することにより液状の組成物Ｂを得た。
組成物Ａを組成物Ｂに変えた以外は実施例１と同じ方法で、積層体を得た。
バクテリオファージＱβを用いた抗ウイルス性評価を行った。バクテリオファージＱβに対する抗ウイルス活性値は５．３であった。 [Example 2]
83.56 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved. To this, 2.50 parts by mass of iminoctadine acetate preparation (Befuran TG 40 (manufactured by Nippon Soda Co., Ltd.): containing 40% iminoctadine acetate) (1 part by mass as iminoctadine acetate) is added and mixed to form a liquid. A composition B was obtained.
A laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition B.
Antiviral evaluation using bacteriophage Qβ was performed. The antiviral activity value against bacteriophage Qβ was 5.3.
エチレングリコールモノｎ－ブチルエーテル８３．５６質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し溶解させた。これにイミノクタジン酢酸塩製剤（べフラン原体４０（日本曹達社製）：イミノクタジン酢酸塩４０％含有）２．５０質量部（イミノクタジン酢酸塩として１質量部）を添加し、混合することにより液状の組成物Ｂを得た。
組成物Ａを組成物Ｂに変えた以外は実施例１と同じ方法で、積層体を得た。
バクテリオファージＱβを用いた抗ウイルス性評価を行った。バクテリオファージＱβに対する抗ウイルス活性値は５．３であった。 [Example 2]
83.56 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved. To this, 2.50 parts by mass of iminoctadine acetate preparation (Befuran TG 40 (manufactured by Nippon Soda Co., Ltd.): containing 40% iminoctadine acetate) (1 part by mass as iminoctadine acetate) is added and mixed to form a liquid. A composition B was obtained.
A laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition B.
Antiviral evaluation using bacteriophage Qβ was performed. The antiviral activity value against bacteriophage Qβ was 5.3.
〔実施例３〕
エチレングリコールモノｎ－ブチルエーテル８５．２３質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し溶解させた。これにイミノクタジンアルベシル酸塩水和剤（ベルクート（登録商標）フロアブル；イミノクタジンアルベシル酸塩３０％含有）０．８３質量部（イミノクタジンアルベシル酸塩として０．２５質量部）を添加し、混合することにより液状の組成物Ｃを得た。
組成物Ａを組成物Ｃに変えた以外は実施例１と同じ方法で、積層体を得た。
バクテリオファージφ６を用いた抗ウイルス性評価を行った。バクテリオファージφ６に対する抗ウイルス活性値は５．２であった。 [Example 3]
85.23 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved. To this, 0.83 parts by mass of iminoctadine albesilate wettable powder (Berkut (registered trademark) flowable; containing 30% iminoctadine albesilate) (0.25 parts by mass as iminoctadine albesilate) is added and mixed. Thus, a liquid composition C was obtained.
A laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition C.
Antiviral evaluation was performed using bacteriophage φ6. The antiviral activity value against bacteriophage φ6 was 5.2.
エチレングリコールモノｎ－ブチルエーテル８５．２３質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し溶解させた。これにイミノクタジンアルベシル酸塩水和剤（ベルクート（登録商標）フロアブル；イミノクタジンアルベシル酸塩３０％含有）０．８３質量部（イミノクタジンアルベシル酸塩として０．２５質量部）を添加し、混合することにより液状の組成物Ｃを得た。
組成物Ａを組成物Ｃに変えた以外は実施例１と同じ方法で、積層体を得た。
バクテリオファージφ６を用いた抗ウイルス性評価を行った。バクテリオファージφ６に対する抗ウイルス活性値は５．２であった。 [Example 3]
85.23 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and dissolved. To this, 0.83 parts by mass of iminoctadine albesilate wettable powder (Berkut (registered trademark) flowable; containing 30% iminoctadine albesilate) (0.25 parts by mass as iminoctadine albesilate) is added and mixed. Thus, a liquid composition C was obtained.
A laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition C.
Antiviral evaluation was performed using bacteriophage φ6. The antiviral activity value against bacteriophage φ6 was 5.2.
〔実施例４〕
イミノクタジンアルベシル酸塩水和剤（ベルクート（登録商標）フロアブル；イミノクタジンアルベシル酸塩３０％含有）３．３３質量部（イミノクタジンアルベシル酸塩として１質量部）と水性ニス（アクリルエマルション樹脂塗料、株式会社アサヒペン製）９６．６７質量部とを混ぜ合わせて液状の組成物Ｄを得た。
自動塗工装置（ＰＩ－１２１０：テスター産業社製）を用いて、１４８ｍｍ×２１０ｍｍのポリエチレンテレフタレートフィルム（ルミラー(Ｒ)フィルム（T60透明）２５０μｍ）の片側全面に、組成物Ｄを約３ｍＬ塗布した。その後、１００℃の恒温槽に入れ１分間乾燥させ、ポリエチレンテレフタレートフィルムと組成物Ｄの不揮発成分からなる膜とが積層されてなる積層体を得た。
バクテリオファージφ６を用いた抗ウイルス性評価を行った。バクテリオファージφ６に対する抗ウイルス活性値は５．２であった。 [Example 4]
Iminoctadine albesilate wettable powder (Berkut (registered trademark) flowable; containing 30% iminoctadine albesilate) 3.33 parts by mass (1 part by mass as iminoctadine albesilate) and water-based varnish (acrylic emulsion resin paint, stock) Asahipen Co., Ltd.) was mixed with 96.67 parts by mass to obtain a liquid composition D.
About 3 mL of composition D was applied to one side of a polyethylene terephthalate film (Lumirror (R) film (T60 transparent) 250 μm) of 148 mm × 210 mm using an automatic coating device (PI-1210: manufactured by Tester Sangyo Co., Ltd.). . After that, it was placed in a constant temperature bath at 100° C. and dried for 1 minute to obtain a laminate in which a polyethylene terephthalate film and a film composed of non-volatile components of composition D were laminated.
Antiviral evaluation was performed using bacteriophage φ6. The antiviral activity value against bacteriophage φ6 was 5.2.
イミノクタジンアルベシル酸塩水和剤（ベルクート（登録商標）フロアブル；イミノクタジンアルベシル酸塩３０％含有）３．３３質量部（イミノクタジンアルベシル酸塩として１質量部）と水性ニス（アクリルエマルション樹脂塗料、株式会社アサヒペン製）９６．６７質量部とを混ぜ合わせて液状の組成物Ｄを得た。
自動塗工装置（ＰＩ－１２１０：テスター産業社製）を用いて、１４８ｍｍ×２１０ｍｍのポリエチレンテレフタレートフィルム（ルミラー(Ｒ)フィルム（T60透明）２５０μｍ）の片側全面に、組成物Ｄを約３ｍＬ塗布した。その後、１００℃の恒温槽に入れ１分間乾燥させ、ポリエチレンテレフタレートフィルムと組成物Ｄの不揮発成分からなる膜とが積層されてなる積層体を得た。
バクテリオファージφ６を用いた抗ウイルス性評価を行った。バクテリオファージφ６に対する抗ウイルス活性値は５．２であった。 [Example 4]
Iminoctadine albesilate wettable powder (Berkut (registered trademark) flowable; containing 30% iminoctadine albesilate) 3.33 parts by mass (1 part by mass as iminoctadine albesilate) and water-based varnish (acrylic emulsion resin paint, stock) Asahipen Co., Ltd.) was mixed with 96.67 parts by mass to obtain a liquid composition D.
About 3 mL of composition D was applied to one side of a polyethylene terephthalate film (Lumirror (R) film (T60 transparent) 250 μm) of 148 mm × 210 mm using an automatic coating device (PI-1210: manufactured by Tester Sangyo Co., Ltd.). . After that, it was placed in a constant temperature bath at 100° C. and dried for 1 minute to obtain a laminate in which a polyethylene terephthalate film and a film composed of non-volatile components of composition D were laminated.
Antiviral evaluation was performed using bacteriophage φ6. The antiviral activity value against bacteriophage φ6 was 5.2.
〔比較例１〕
エチレングリコールモノｎ－ブチルエーテル８１．０６質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し、溶解させた。これに、ポリヘキサメチレンビグアナイド製剤（ポリヘキサメチレンビグアナイド２０％含有）５．０質量部（ポリヘキサメチレンビグアナイドとして１部）を添加し、混合することにより液状の組成物Ｅを得た。
組成物Ａを組成物Ｅに変えた以外は実施例１と同じ方法で、積層体を得た。
バクテリオファージＱβを用いた抗ウイルス性評価を行った。バクテリオファージＱβに対する抗ウイルス活性値は２．０であった。 [Comparative Example 1]
81.06 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and allowed to dissolve. To this, 5.0 parts by mass of a polyhexamethylene biguanide preparation (containing 20% polyhexamethylene biguanide) (1 part as polyhexamethylene biguanide) was added and mixed to obtain a liquid composition E.
A laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition E.
Antiviral evaluation using bacteriophage Qβ was performed. The antiviral activity value against bacteriophage Qβ was 2.0.
エチレングリコールモノｎ－ブチルエーテル８１．０６質量部に、シランカップリング剤（３－メタクリロキシプロピルトリメトキシシラン）８．７４質量部、オルガノシリカゾル（アモルファスシリカ３０％、Ｎ－メチル－２－ピロリドン７０％）３．５質量部、アルミニウム（III）アセチルアセトネート１．５質量部、および２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノプロパン－１－オン０．２質量部を添加し、溶解させた。これに、ポリヘキサメチレンビグアナイド製剤（ポリヘキサメチレンビグアナイド２０％含有）５．０質量部（ポリヘキサメチレンビグアナイドとして１部）を添加し、混合することにより液状の組成物Ｅを得た。
組成物Ａを組成物Ｅに変えた以外は実施例１と同じ方法で、積層体を得た。
バクテリオファージＱβを用いた抗ウイルス性評価を行った。バクテリオファージＱβに対する抗ウイルス活性値は２．０であった。 [Comparative Example 1]
81.06 parts by mass of ethylene glycol mono-n-butyl ether, 8.74 parts by mass of a silane coupling agent (3-methacryloxypropyltrimethoxysilane), organosilica sol (amorphous silica 30%, N-methyl-2-pyrrolidone 70% ) 3.5 parts by mass, aluminum (III) acetylacetonate 1.5 parts by mass, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one 0.2 parts by mass added and allowed to dissolve. To this, 5.0 parts by mass of a polyhexamethylene biguanide preparation (containing 20% polyhexamethylene biguanide) (1 part as polyhexamethylene biguanide) was added and mixed to obtain a liquid composition E.
A laminate was obtained in the same manner as in Example 1, except that composition A was changed to composition E.
Antiviral evaluation using bacteriophage Qβ was performed. The antiviral activity value against bacteriophage Qβ was 2.0.
以上のとおり、ポリヘキサメチレンビグアナイドと樹脂とを含有する組成物（比較例１）は抗ウイルス性が極めて低いが、本発明の組成物（実施例）は、良好な抗ウイルス性を有する。
As described above, the composition containing polyhexamethylene biguanide and resin (Comparative Example 1) has extremely low antiviral properties, but the composition of the present invention (Example) has good antiviral properties.
Claims (3)
- イミノクタジン及びその塩から選ばれる少なくとも一つを含有する、抗ウイルス剤組成物。 An antiviral agent composition containing at least one selected from iminoctadine and salts thereof.
- 請求項１に記載の抗ウイルス剤組成物、および樹脂を含有する、樹脂組成物。 A resin composition containing the antiviral agent composition according to claim 1 and a resin.
- 請求項２に記載の樹脂組成物を含有する、成形体。 A molded article containing the resin composition according to claim 2.
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| JP2022032673 | 2022-03-03 | ||
| JP2022-032673 | 2022-03-03 |
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| WO2023167055A1 true WO2023167055A1 (en) | 2023-09-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/JP2023/006177 WO2023167055A1 (en) | 2022-03-03 | 2023-02-21 | Antiviral agent |
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| WO (1) | WO2023167055A1 (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178801A (en) * | 1984-02-24 | 1985-09-12 | Dainippon Ink & Chem Inc | Guanidine fungicide for agriculture and horticulture |
| JPS6239503A (en) * | 1985-08-13 | 1987-02-20 | Dainippon Ink & Chem Inc | Industrial preservative |
| JP2007508234A (en) * | 2003-06-26 | 2007-04-05 | バイオトロン・リミテッド | Antiviral acylguanidine compounds and methods |
| JP2008543886A (en) * | 2005-06-24 | 2008-12-04 | バイオトロン リミテッド | Antiviral compounds and methods |
| JP2013014551A (en) * | 2011-07-05 | 2013-01-24 | Settsu Seiyu Kk | Composition for virus inactivation |
| JP2017105723A (en) * | 2015-12-09 | 2017-06-15 | サラヤ株式会社 | Composition having calicivirus inactivation effect |
| JP2022189422A (en) * | 2021-06-11 | 2022-12-22 | 日本曹達株式会社 | Industrial pest control composition |
-
2023
- 2023-02-21 WO PCT/JP2023/006177 patent/WO2023167055A1/en unknown
- 2023-02-23 TW TW112106775A patent/TW202346482A/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178801A (en) * | 1984-02-24 | 1985-09-12 | Dainippon Ink & Chem Inc | Guanidine fungicide for agriculture and horticulture |
| JPS6239503A (en) * | 1985-08-13 | 1987-02-20 | Dainippon Ink & Chem Inc | Industrial preservative |
| JP2007508234A (en) * | 2003-06-26 | 2007-04-05 | バイオトロン・リミテッド | Antiviral acylguanidine compounds and methods |
| JP2008543886A (en) * | 2005-06-24 | 2008-12-04 | バイオトロン リミテッド | Antiviral compounds and methods |
| JP2013014551A (en) * | 2011-07-05 | 2013-01-24 | Settsu Seiyu Kk | Composition for virus inactivation |
| JP2017105723A (en) * | 2015-12-09 | 2017-06-15 | サラヤ株式会社 | Composition having calicivirus inactivation effect |
| JP2022189422A (en) * | 2021-06-11 | 2022-12-22 | 日本曹達株式会社 | Industrial pest control composition |
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|---|---|
| TW202346482A (en) | 2023-12-01 |
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