Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/74—Synthetic polymeric materials
  • A61K31/765—Polymers containing oxygen
  • A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/74—Synthetic polymeric materials
  • A61K31/785—Polymers containing nitrogen
• • 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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
• • 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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/12—Quaternary ammonium compounds
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/12—Antivirals
  • A61P31/14—Antivirals for RNA viruses
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate

Definitions

• the present invention relates to anti-coronavirus agents and the like. More specifically, it relates to anti-coronavirus agents and the like containing specific polymers (polymers, copolymers, amino group-containing copolymers).
• Patent Document 1 discloses that nanostructures composed of block copolymers containing specific ammonium moieties can be used as antiviral agents.
• Patent Literature 2 discloses that a fiber composition comprising a combination of silver amino acid, zinc amino acid, carboxyvinyl polymer, copper glutamate, etc. has antiviral properties against influenza virus.
• Non-Patent Document 1 describes that a specific polyamide polyamine compound has antiviral properties against various viruses.
• An object of the present invention is to provide an anti-coronavirus agent capable of exhibiting an anti-viral effect against novel coronaviruses and the like.
• At least one structural unit An anti-coronavirus agent (anti-coronavirus composition) containing a polymer comprising a).
• An anti-coronavirus agent anti-coronavirus composition containing a polymer comprising a.
• R 1 , R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
• R 4 to R 8 each independently represents a hydrogen atom or an organic group
• X represents a divalent linking group
• Y- represents an anion.
• Structural unit (a) comprises a structural unit derived from N-mono- or dialkylaminoalkyl (meth)acrylate, and structural unit (b) comprises a structural unit derived from (meth)acrylic acid alkyl ester [2]- The agent according to any one of [5].
• the ratio of the structural unit (a) is 50% by mass or more and the ratio of the structural unit (b) is 5% by mass or more relative to 100% by mass of the total structural units, and the Hildebrand solubility parameter of the polymer is 12. ⁇ 23 (MPa) 1/2 , the agent according to any one of [1] to [7].
• the agent according to any one of [1] to [9] which is in the form of an aqueous solution [eg, an aqueous solution with a pH of 2 to 11 (eg, 4 to 9)] containing the polymer.
• the present invention provides a structural unit represented by the following general formula (1), a structural unit that is a salt of the following general formula (1) (for example, a salt with an acid), and a structural unit represented by the following general formula (2): Polymers (polymers, copolymers, amino group-containing co- polymer).
• the present invention provides a structural unit represented by the following general formula (1), a structural unit that is a salt of the following general formula (1) (e.g., a salt with an acid), and a structural unit represented by the following general formula (2): At least one structural unit (a) selected from structural units [a structural unit (a) derived from an amino group-containing monomer], and another structural unit (b) represented by the following general formula (3) [ Structural unit (b) derived from a monomer containing a hydrocarbon group having 2 or more carbon atoms] and a polymer (polymer, copolymer, amino group-containing copolymer) containing an anti- It may be a coronavirus agent.
• a structural unit represented by the following general formula (1) a structural unit that is a salt of the following general formula (1) (e.g., a salt with an acid)
• a structural unit represented by the following general formula (2) At least one structural unit (a) selected from structural units [a structural unit (a) derived from an amino group-containing
• R 1 , R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
• R 4 to R 8 each Independently represents a hydrogen atom or an organic group having 1 to 12 carbon atoms
• X represents a divalent linking group.
• Y - represents an anion.
• asterisks represent general formula (1)
• general formula (2 ) represents an atom contained in another structural unit of the same or different type to which the structural unit represented by ) is bonded.
• R 1 , R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, X represents a divalent linking group, R 9 represents an optionally substituted hydrocarbon group having 2 or more carbon atoms, provided that the asterisk is the same or different other structural unit to which the structural unit represented by general formula (3) is bonded; represents the contained atoms.
• the copolymer anti-coronavirus agent, anti-viral agent
• the copolymer is used (applied and adhered to the application site) to disinfect or disinfect viruses (especially coronaviruses such as novel coronavirus). Methods of activation (viricidal) are included.
• the anti-coronavirus agent containing the polymer (amino group-containing copolymer) of the present disclosure has antiviral properties against coronaviruses, especially SARS-CoV-2.
• the polymer (amino group-containing copolymer) of the present disclosure can be used alone or as a composition with other compounds as a product having antiviral properties.
• the anti-coronavirus agent of the present disclosure includes a polymer having at least a specific structural unit [structural unit (a), structural unit derived from amino group-containing monomer].
• structural unit (a) structural unit derived from amino group-containing monomer.
• Polymers having such structural units tend to exert anti-coronavirus functions efficiently, probably because they tend to act on the envelope of coronaviruses.
• structural units having such structural units have an amino group or an ammonium base, they are often relatively safe (for example, have little skin irritation or skin sensitization).
• the polymer may have other structural units (structural units different from the structural unit (a)) in addition to the structural unit (a).
• an anti-coronavirus agent comprises a structural unit derived from an amino group-containing monomer, a specific structural unit [structural unit (b), a structural unit derived from a hydrophobic monomer ( It may be referred to as a hydrophobic unit, etc.)].
• the polymer of the present disclosure can, unexpectedly, exert an antiviral function, especially an anti-coronavirus function (exhibit a particularly excellent anti-coronavirus function).
• an anti-coronavirus function exhibit a particularly excellent anti-coronavirus function.
• the structural unit (a) and other structural units are clearly separated. Therefore, the penetration into the coronavirus by other structural units (hydrophobic moieties) (and the action and contact of the structural unit (a) on the envelope) is easily performed efficiently, and as described above, the structural unit (a ), it is thought that synergistic excellent anti-coronavirus function can be exhibited.
• the hydrophobic site can be efficiently penetrated into the envelope of minute coronaviruses, and the function can be exhibited more efficiently.
• the polymer may be referred to as a polymer, copolymer, or the like of the present disclosure.
• the structural unit (a) (structural unit derived from amino group-containing monomer) is a structural unit of the following general formula (1), a salt of the following general formula (1) (e.g., a salt with an acid) It is represented by a certain structural unit and/or a structural unit of the following general formula (2).
• R 1 , R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
• R 4 to R 8 each independently represents a hydrogen atom or an organic group (eg, an organic group having 1 to 12 carbon atoms)
• X represents a divalent linking group.
• Y ⁇ represents an anion.
• an asterisk (*) is a structural unit represented by general formula (1), a structural unit that is a salt of general formula (1), or a structural unit that is a structural unit represented by general formula (2). Alternatively, it represents an atom contained in another heterogeneous structural unit.
• atoms contained in another structural unit of the same type means, for example, if the structural unit is represented by general formula (1), another structural unit represented by general formula (1) represents that it is an atom contained in, and "an atom contained in another heterogeneous structural unit” is, for example, if the structural unit is represented by general formula (1), it is represented by general formula (1) Represents an atom contained in a structural unit other than a structural unit.
• the structure derived from the amino group-containing monomer is, for example, an ethylenically unsaturated group and a primary to tertiary amino group represented by the following general formula (4), or an acid of a primary to tertiary amino group It can be formed by radical polymerization of a hydrate or a monomer having a quaternary ammonium base represented by the following general formula (5), but is not limited to this.
• R 4 to R 8 in general formulas (4) and (5) above are the same as R 4 to R 8 in general formulas (1) and (2) above.
• R 1 and R 2 may preferably be hydrogen atoms
• R 3 may preferably be a hydrogen atom or a methyl group.
• the organic group includes, for example, an organic group having 1 to 12 carbon atoms.
• organic groups having 1 to 12 carbon atoms include hydrocarbon groups [e.g., alkyl groups (e.g., methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, etc.
• C 1-12 alkyl groups preferably C 1-8 alkyl groups, more preferably C 1-4 alkyl groups, etc.
• alkenyl groups for example, C 2-12 alkenyl groups such as vinyl groups and allyl groups.
• group hydrocarbon group and the like.
• the organic group may have a substituent such as a hydroxy group or a halogen atom.
• R 4 , R 5 , R 6 , R 7 and R 8 may preferably be hydrogen atoms or hydrocarbon groups (eg, alkyl groups).
• R 4 and R 5 in formula (1), and R 6 , R 7 and R 8 in formula (2) may be the same or different, and the two may bind to each other or One and X may combine with each other to form a ring together with the nitrogen atom (N), or may not form a ring.
• the divalent linking group X is, for example, a direct bond, an ether group (or ether bond, -O-), a thioether group (or thioether bond, -S-), carbonyl Group containing group (carbonyl group, ester group, amide group, urethane group, etc.), hydrocarbon group [e.g., alkylene group or alkylidene group (e.g., methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, etc.
• alkylene group or alkylidene group e.g., methylene group, ethylene group, trimethylene group, propylene group, tetramethylene group, etc.
• C 1-20 alkylene group or alkylidene group preferably C 1-12 alkylene group or alkylidene group, more preferably C 1-8 alkylene group or alkylidene group, etc.
• a group in which two or more (plural) of these are bonded ⁇ for example , -C ( O) -O-R-
• R represents a hydrocarbon group (for example, an alkylene group such as an ethylene group or an alkylidene group)]. or an alkylidene group, etc.) and other groups, etc. ⁇ .
• the hydrocarbon group may have a substituent such as a hydroxy group and a halogen atom.
• an ether group, a thioether group, a carbonyl group, an ester group, an amide group, a urethane group, and the like usually do not directly form X, and are used as a group bonded to a hydrocarbon group or the like [further, the formula (1) or (2 ) (in other words, a hydrocarbon group or the like bonds to the nitrogen atom (N) of formula (1) or (2))] in many cases.
• the polymer may have one or more structural units (a).
• the structural unit derived from the amino group-containing monomer is formed, for example, by radically polymerizing the amino group-containing monomer.
• the amino group-containing monomer include N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, N,N-dialkylamino group-containing (meth)acrylates such as N,N-diethylaminopropyl (meth)acrylate, monomers obtained by adding a quaternizing agent to the above monomers, or hydrochloric acid, acetic acid, lactic acid, phosphoric acid, Neutralized products with acids such as citric acid, succinic acid, malic acid, etidronic acid, ascorbic acid, glutamic acid, aspartic acid; N,N-dimethylaminoethyl (meth)acrylamide, N,N-die
• the structural unit derived from the amino group-containing monomer is particularly an N-substituted aminoalkyl (meth)acrylate, for example, a structural unit derived from N,N-dimethylaminoethyl (meth)acrylate of the following general formula (6 ) is preferred.
• the structural unit (a) is an N-substituted aminoalkyl (meth)acrylate [for example, an N-mono- or dialkylaminoalkyl (meth)acrylate such as N,N-dimethylaminoethyl (meth)acrylate (for example, an N- mono- or di-C 1-4 alkylamino C 1-4 alkyl (meth)acrylate)]-derived structural units.
• N-substituted aminoalkyl (meth)acrylate for example, an N-mono- or dialkylaminoalkyl (meth)acrylate such as N,N-dimethylaminoethyl (meth)acrylate (for example, an N- mono- or di-C 1-4 alkylamino C 1-4 alkyl (meth)acrylate
• R 10 in the general formula (6) represents a hydrogen atom or a methyl group.
• the asterisk represents an atom contained in another structural unit of the same or different type to which the structural unit represented by general formula (6) is bonded.
• Most preferred are structural units derived from N,N-dimethylaminoethyl methacrylate.
• the content of the structural unit (a) is the total structural unit (all monomers constituting the copolymer of the present disclosure Structural unit derived from body) 100% by mass, for example, 1% by mass or more (e.g., 2% by mass or more, 3% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass 25% by mass or more, 30% by mass or more, 35% by mass or more, 40% by mass or more, 45% by mass or more, 50% by mass or more), etc., and 100% by mass or less (e.g., less than 100% by mass , 99% by mass or less, 97% by mass or less, 96% by mass or less, 95% by mass or less, 94% by mass or less, 93% by mass or less, 92% by mass or less, 91% by mass or less, 90% by mass or less, 88% by mass or less , 85% by mass or more (e.g., 2% by mass or more, 3% by mass or more, 5% by mass
• the content of the structural unit (a) may form an appropriate range by combining the upper limit and the lower limit, for example, 1% by mass or more and 99% by mass or less, preferably 10% by mass or more and 97% by mass or less. , more preferably 36% by mass or more and 96% by mass or less, and most preferably 50% by mass or more and 95% by mass or less.
• the hydrophilic-hydrophobic balance is in an appropriate range, and the proportion of cationic sites that can act on the surface of the coronavirus and the proportion of hydrophobic sites that act on the envelope are appropriate.
• the anti-coronavirus performance of the anti-coronavirus agent of the present disclosure tends to improve, probably because the water-solubility of the coalescence is more likely to be maintained.
• ⁇ Structural unit (b) (structural unit derived from a monomer containing a hydrocarbon group having 2 or more carbon atoms)>
• the structural unit (b) [a structural unit derived from a monomer containing a hydrocarbon group having 2 or more carbon atoms (for example, containing in a side chain)] is, for example, a structural unit of the following general formula (3) is represented by
• R 1 , R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
• X represents a divalent linking group
• R 9 is a substituted represents a hydrocarbon group having 2 or more carbon atoms which may have a group.
• the asterisk represents an atom contained in another structural unit of the same or different type to which the structural unit represented by general formula (3) is bonded.
• the carbon-carbon double bond portion of the monomer having an ethylenically unsaturated group and a hydrocarbon group having 2 or more carbon atoms is carbon carbon Represents a structural unit replaced by a single bond.
• a hydrocarbon group having 2 or more carbon atoms may generally be a radically polymerizable group (e.g., an ethylenically unsaturated group) or may not be a radically polymerizable group, such as a saturated hydrocarbon group, an unsaturated It may be a hydrocarbon group (alkenyl group, etc.), an aromatic hydrocarbon group, etc., preferably a saturated hydrocarbon group (alkyl group, etc.).
• the monomer containing a hydrocarbon group having 2 or more carbon atoms may have at least one hydrocarbon group having 2 or more carbon atoms, and two or more (plural) hydrocarbon groups having 2 or more carbon atoms may have.
• hydrocarbon groups having 2 or more carbon atoms are linked via a suitable linking group (e.g., ether group, thioether group, ester group, amide group, etc.). good too.
• a suitable linking group e.g., ether group, thioether group, ester group, amide group, etc.
• R9 may form a ring together with X.
• structural units can be formed, for example, by radically polymerizing the monomers.
• the structural unit derived from the monomer containing a hydrocarbon group having 2 or more carbon atoms may have the same structure as the structural unit in which the carbon-carbon double bond portion is replaced with a carbon-carbon single bond. It may be a structural unit formed by a post-reaction.
• the structural unit of general formula (3) does not correspond to the structural unit (a). Therefore, for example, a monomer containing a hydrocarbon group having 2 or more carbon atoms may have a substituent such as a hydroxy group or a halogen atom as long as it contains a hydrocarbon group having 2 or more carbon atoms. , usually does not have any of the group represented by the formula (4), the salt of the group represented by the formula (4) (salt with an acid), and the group represented by the formula (5).
• the divalent linking group X is, for example, a direct bond, an ether group (or an ether bond, -O-), a group containing a carbonyl group (ester group, amide group, urethane group, etc.), A group in which these are bonded to a hydrocarbon group ⁇ e.g., an oxyalkylene group or an oxyalkylidene group [e.g., an oxymethylene group (-OCH 2 -), an oxyC 1-20 alkylene group such as an oxyethylene group, or an alkylidene group] ⁇ , etc.
• X is preferably an ester group or an amide group, more preferably an ester group.
• the polymer may have one or more structural units (b).
• the monomer containing a hydrocarbon group having 2 or more carbon atoms is not particularly limited, but an ester of (meth)acrylic acid and an alcohol optionally having a substituent (having a substituent aromatic vinyl monomers such as styrene; esters of unsaturated alcohols and carboxylic acids such as vinyl propionate and vinyl butyrate; alkyl vinyl ethers having 2 or more carbon atoms such as ethyl vinyl ether an addition reaction product of an unsaturated monomer having a cyclic ether-containing group having 2 to 8 carbon atoms such as 1-allyloxy-3-butoxypropan-2-ol and an alcohol having 1 to 20 carbon atoms; ethylene oxide of allyl alcohol adducts, ethylene oxide adducts of methallyl alcohol, ethylene oxide adducts of isoprenol, and other alkylene oxide adducts of unsaturated alcohols having 2 to 20 carbon atoms and their terminal hydrophobically modified products;
• the monomer containing a hydrocarbon group having 2 or more carbon atoms preferably contains at least one (meth)acrylic acid ester.
• the (meth)acrylic acid ester is preferably an ester of (meth)acrylic acid and a monoalcohol in which the hydrocarbon group of the monoalcohol has 2 to 20 carbon atoms.
• the carbon number of the hydrocarbon group of the monoalcohol is more preferably 2-16, still more preferably 2-12, and particularly preferably 2-8. When the number of carbon atoms in the hydrocarbon group is 2 to 20, the water-solubility and viscosity of the polymer can be set within suitable ranges, resulting in excellent handling.
• the hydrocarbon group has 2 to 12 carbon atoms, the production of the polymer is facilitated, and the polymer is excellent in safety as well as anti-coronavirus properties. Furthermore, when the number of carbon atoms in the hydrocarbon group is 2 to 8, not only is the polymer easy to produce, but it is also highly safe, has an increased affinity for coronavirus surface proteins, and has anti-coronavirus properties. will be further improved.
• the above hydrocarbon group is preferably an alkyl group (C 2-20 alkyl group, C 2-16 alkyl group, C 2-12 alkyl group, C 2-8 alkyl group, etc.) or alkenyl group, more preferably alkyl is the base.
• Structural unit (b) (or hydrophobic unit, for example, a monomer containing a hydrocarbon group having 2 or more carbon atoms) is a solubility parameter (Hildebrand solubility parameter) [in a homopolymer (homopolymer) (and 35 (MPa) 1/2 or less (e.g., 33 (MPa) 1/2 or less), preferably 32 (MPa) 1/2 or less (e.g., 30.8 (MPa) 1 /2 or less), more preferably 30 (MPa) 1/2 or less (e.g., 28.7 (MPa) 1/2 or less), still more preferably 28 (MPa) 1/2 or less (e.g., 26.7 (MPa) ) 1/2 or less), or 25 (MPa) 1/2 or less (for example, 24.6 (MPa) 1/2 or less).
• solubility parameter Hildebrand solubility parameter
• the (lower limit of) the solubility parameter of the structural unit (b) is not particularly limited, but is, for example, 5 (MPa) 1/2 or more (e.g., 8 (MPa) 1/2 or more, 10 (MPa) 1/2 or more , 10.3 (MPa) 1/2 or more).
• the solubility parameter as described above may be the value (average value) of the entire structural units (b).
• the solubility parameter of the structural unit (b) as a whole is, for example, the solubility parameter of each structural unit (b) (or each monomer) and each structural unit (b) (or each monomer) It can be calculated from the volume ratio of the polymer.
• the solubility parameter means the Hildebrand solubility parameter (SP value). You can refer to the calculated value.
• the (meth)acrylic acid ester a (meth)acrylic acid alkyl ester (alkyl (meth)acrylate) is preferable.
• a structural unit derived from ethyl (meth)acrylate and represented by the following general formula (7) is particularly preferable. Therefore, the structural unit (b) contains a structural unit derived from a (meth)acrylic acid alkyl ester [alkyl (meth)acrylate such as C 1-4 alkyl (meth)acrylate (ethyl (meth)acrylate, etc.)].
• R 10 represents a hydrogen atom or a methyl group.
• the asterisk represents an atom contained in another structural unit of the same or different type to which the structural unit represented by general formula (7) is bonded.
• Structural units derived from ethyl methacrylate are most preferred.
• the content of the structural unit (b) is the total structural unit (all monomers constituting the copolymer of the present disclosure Structural unit derived from body) 100% by mass, for example, 1% by mass or more (e.g., 2% by mass or more, 3% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass , 25% by mass or more, 30% by mass or more), etc., and 99% by mass or less (e.g., 97% by mass or less, 95% by mass or less, 90% by mass or less, 85% by mass or less, 80% by mass or less) , 75% by mass or less, 70% by mass or less, 65% by mass or less, 60% by mass or less, 55% by mass or less, 50% by mass or less, etc.).
• 1% by mass or more e.g., 2% by mass or more, 3% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass ,
• the content of the structural unit (b) may form an appropriate range by combining the upper limit and the lower limit, for example, 1% by mass or more and 99% by mass or less, preferably 3% by mass or more and 90% by mass % or less, more preferably 4% by mass or more and 70% by mass or less, and most preferably 5% by mass or more and 50% by mass or less. If the content ratio is within such a range, the polymer (copolymer) will have appropriate hydrophobicity, the anti-coronavirus performance will be improved, and there will be a tendency to exhibit high anti-virus performance.
• the polymer (copolymer) of the present disclosure may optionally be a structural unit derived from an amino group-containing monomer, a structural unit derived from a monomer containing a hydrocarbon group having 2 or more carbon atoms, a unit other than It may have a structural unit derived from a mer (also referred to as a structural unit derived from another monomer).
• Other monomers are not particularly limited as long as they do not have an amino group and can be copolymerized with an amino group-containing monomer and a monomer containing a hydrocarbon group having 2 or more carbon atoms. .
• the polymer contains the above structural unit (a) and structural unit (b) in an appropriate combination and ratio [for example, a monomer containing a hydrocarbon group having 2 or more carbon atoms) is polymerized in a preferred ratio] As long as the copolymer functions (for example, hydrophobicity) are sufficiently maintained.
• structural units derived from other monomers represent structural units in which at least one carbon-carbon double bond of the other monomer is replaced with a carbon-carbon single bond.
• the structural unit derived from other monomers may have the same structure as the structure in which at least one carbon-carbon double bond of the other monomer is replaced with a carbon-carbon single bond.
• the structural units are not limited to those formed by polymerization, and may be, for example, structural units formed by post-reaction after polymerization.
• Structural units derived from other monomers are not particularly limited, but unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, ⁇ -allyloxyacrylic acid and salts thereof; olefinic units such as propylene; monomer; vinyl halide such as vinyl chloride; methyl vinyl ether;
• the polymer may have one or more other structural units.
• the content of structural units derived from other monomers in the polymer (copolymer) of the present disclosure is the structural units derived from all monomers constituting the polymer (copolymer) of the present disclosure. It is less than 15% by mass with respect to 100% by mass. It is more preferably less than 10% by mass, still more preferably less than 5% by mass. These other monomers may be used alone or in combination of two or more.
• the polymer (copolymer) of the present disclosure preferably has a weight average molecular weight (Mw) of 4000 or more and 800000 or less, more preferably 6000 or more and 400000 or less, and 7000 or more and 80000 or less. is more preferred.
• Mw weight average molecular weight
• the anti-coronavirus performance of the anti-coronavirus agent of the present disclosure is further improved, and the formulation tends to be excellent in water solubility and dispersibility.
• the weight average molecular weight of the polymer (copolymer) of the present disclosure can be measured using a known technique. Specifically, the GPC method, the viscosity method, and the like can be mentioned.
• the molecular weight distribution of the polymer (copolymer) of the present disclosure is preferably 1.1 or more, more preferably 1.2 or more, still more preferably 1.3 or more, preferably 5.0 or less, and 4.0 or less. is more preferable, and 3.0 or less is even more preferable.
• the solubility parameter (Hildebrand solubility parameter) of the polymer (copolymer) of the present disclosure is, for example, 8 (MPa) 1/2 or more (e.g., 10 (MPa) 1/2 or more), preferably 12 (MPa) 1/2 or more (e.g., 13 (MPa) 1/2 or more), more preferably 14 (MPa) 1/2 or more (e.g., 14.5 (MPa) 1/2 or more), still more preferably 15 (MPa) It may be about 1/2 or more.
• the solubility parameter (Hildebrand solubility parameter) (upper limit) of the polymer (copolymer) of the present disclosure is, for example, 30 (MPa) 1/2 or less (e.g., 28 (MPa) 1/2 or less, 26 ( MPa) 1/2 or less, 25 (MPa) 1/2 or less, 24 (MPa) 1/2 or less), preferably 23 (MPa) 1/2 or less (e.g., 22 (MPa) 1/2 or less), more It is preferably 21 (MPa) 1/2 or less (for example, 20.5 (MPa) 1/2 or less), more preferably 20 (MPa) 1/2 or less.
• the ⁇ d (dispersion term) in the Hansen solubility parameter of the polymer (copolymer) of the present disclosure is, for example, preferably 10 (MPa) 1/2 or more, more preferably 11 (MPa) 1/2 or more, and 12 ( MPa) 1/2 or more is more preferable, 21 (MPa) 1/2 or less is preferable, 20 (MPa) 1/2 or less is more preferable, and 19 (MPa) 1/2 or less is more preferable.
• the ⁇ p (polar term) in the Hansen solubility parameter of the polymer (copolymer) of the present disclosure is, for example, preferably 3.0 (MPa) 1/2 or more, and more preferably 4.0 (MPa) 1/2 or more. preferably 5.0 (MPa) 1/2 or more, more preferably 11.0 (MPa) 1/2 or less, more preferably 10.0 (MPa) 1/2 or less, 9.0 (MPa) 1 /2 or less is more preferable.
• ⁇ h (hydrogen bond term) in the Hansen solubility parameter of the polymer (copolymer) of the present disclosure for example, 3.0 (MPa) 1/2 or more is preferable, and 4.0 (MPa) 1/2 or more is More preferably, 5.0 (MPa) 1/2 or more is more preferable, 11.0 (MPa) 1/2 or less is preferable, 10.0 (MPa) 1/2 or less is more preferable, and 9.0 (MPa) 1/2 or less is more preferable.
• the Hansen solubility parameter is the solubility parameter introduced by Hildebrand divided into three components, the dispersion term ⁇ d, the polar term ⁇ p, and the hydrogen bonding term ⁇ h, and expressed in three-dimensional space.
• the dispersion term ⁇ d indicates the effect of nonpolar interaction
• the polar term ⁇ p indicates the effect of dipole force
• the hydrogen bond term ⁇ h indicates the effect of hydrogen bond force.
• the solubility parameters (Hildebrand solubility parameter, Hansen solubility parameter) of the polymer (copolymer) of the present disclosure are the monomers used in the polymer (copolymer) [monomers constituting the polymer (copolymer) It can be calculated from the solubility parameter of the solid (originating unit) and the volume ratio of each monomer.
• An example of the calculation method is the Hansen solubility parameter of a copolymer obtained by polymerizing 60 parts by mass of N,N-dimethylaminoethyl methacrylate and 40 parts by mass of ethyl methacrylate.
• the Hansen solubility parameters of N,N-dimethylaminoethyl methacrylate and ethyl methacrylate are respectively as follows.
• each Hansen solubility parameter of a copolymer obtained by polymerizing 60 parts by mass of N,N-dimethylaminoethyl methacrylate and 40 parts by mass of ethyl methacrylate is calculated as follows.
• Hansen Solubility Parameters of each monomer are values extracted from Hansen Solubility Parameters: A User's Handbook.
• the above solubility parameter is preferable in that it is easy to efficiently exert the anti-coronavirus function.
• the copolymer of the present disclosure may be a random copolymer, block copolymer, graft copolymer, or the like.
• the method for producing the polymer (copolymer) of the present disclosure is not particularly limited, but usually at least the raw material monomer of the structural unit (a) (for example, an amino group-containing monomer and a hydrocarbon group having 2 or more carbon atoms It is preferable to produce by polymerizing a monomer containing and optionally other monomers).
• the method for producing the polymer (copolymer) include solution polymerization, bulk polymerization, suspension polymerization, emulsion polymerization, living polymerization, graft polymerization, and the like, and are not particularly limited. However, solution polymerization is preferred.
• the solvent used at this time is not particularly limited, but water; monohydric alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, butanol, THF (tetrahydrofuran); glycerin, (poly)ethylene glycol, propylene glycol, 1, Polyhydric alcohols such as 3-butylene glycol and dipropylene glycol; Aromatic or aliphatic hydrocarbons such as benzene, toluene, xylene, cyclohexane and n-heptane; Esters such as ethyl acetate; Ketones such as acetone and methyl ethyl ketone amides such as dimethylformamide; and ethers such as diethyl ether and dioxane.
• monohydric alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, butanol, THF (tetrahydrofuran); glycerin, (poly
• one or more solvents selected from the group consisting of water and lower alcohols having 1 to 4 carbon atoms from the viewpoint of the solubility of the monomer component and the resulting polymer (copolymer) is preferably used.
• a polyhydric alcohol solvent such as propylene glycol or ethylene glycol may be added to water for polymerization.
• the solubility of the polymer can be enhanced, and the soap-free polymerization can be more sufficiently suppressed. This makes it possible to more sufficiently suppress the formation of polymers with poor water solubility and further improve the transparency of the solution.
• the solvent is water, ethyl alcohol, glycerin, 1,3-butanediol, or a combination of two or more thereof, it can be used directly as a raw material for an external preparation for skin without performing a solvent removal step.
• the monomer is neutralized as described in the section on the structural unit derived from the amino group-containing monomer.
• a neutralized product can be produced by polymerization, or a neutralized product can be produced by polymerizing unneutralized monomers and then neutralizing them by adding a predetermined acid.
• coronavirus is an enveloped virus with a positive single-stranded RNA genome and a nucleocapsid of helix symmetry. Coronaviruses of the present disclosure include coronaviruses that infect humans or non-human animals.
• coronaviruses examples include human coronavirus 229E, OC43, NL63, HKU-1, severe acute respiratory syndrome (SARS) coronavirus, Middle East respiratory syndrome (MERS) coronavirus, novel coronavirus (2019-nCoV, SARS-CoV-2) and the like.
• SARS severe acute respiratory syndrome
• MERS Middle East respiratory syndrome
• Coronaviruses that infect non-humans include porcine epidemic diarrhea virus (PEDV), porcine infectious gastroenteritis virus (TGEV), feline infectious peritonitis virus (FIPV), canine coronavirus (CCV), bovine coronavirus, and horses. Examples include coronavirus, infectious avian bronchitis virus (IBV), avian deltacoronavirus, porcine deltacoronavirus, and the like.
• the coronavirus of the present disclosure may be SARS-CoV-2, which is a virus belonging to the Coronaviridae family, which is the virus responsible for the novel coronavirus disease (COVID-19). be.
• mutant strains for example, spike proteins with mutations such as N501Y, L452R, E484Q, D614G, P681H, Y145H, A222V and E484K
• alpha strains, beta strains, gamma strains, delta strains, kappa strains, lambda strains, mu strains, omicron strains, etc. are known as currently known (publicly known) mutant strains.
• the targets of coronavirus agents include currently unknown mutant strains and new mutant strains that will mutate in the future.
• the anti-coronavirus agent of the present disclosure can be used for any target without particular limitation, but it may be used for the purpose of suppressing coronavirus infection in livestock and pets, and it is expected to have antiviral properties against coronaviruses that infect humans.
• SARS coronavirus, MERS coronavirus, and SARS-CoV-2 may be used as targets, and in recent years, the use of SARS-CoV-2 as a target can be expected to have the effect of suppressing infection. .
• the anti-coronavirus agent (composition, anti-coronavirus composition) of the present disclosure essentially contains the polymer (copolymer) of the present disclosure.
• the upper limit of the content of the polymer (copolymer) of the present disclosure in the anti-coronavirus agent of the present disclosure may be 100% by mass, and the lower limit is not particularly limited. It is preferably at least 0.01% by mass.
• Anti-coronaviral agents of the present disclosure may include solvents such as water, antibacterial agents, preservatives, and the like.
• the above-mentioned other components are not particularly limited as long as they do not inhibit the anti-coronavirus performance of the anti-coronavirus agent. and the like.
• the coronavirus agent of the present invention may further contain metal salts, metal oxides, metal hydroxides, etc. from the viewpoint of improving anti-coronavirus properties.
• the content of the other components is not particularly limited as long as it does not inhibit the anti-coronavirus performance of the anti-coronavirus agent. Preferably.
• a typical anti-coronavirus agent is in a form containing the polymer (copolymer) of the present disclosure and a solvent [eg, solution (especially aqueous solution)].
• a solvent eg, solution (especially aqueous solution)
• solvents examples include water, aqueous solvents [eg, alcohols (eg, methanol, ethanol, isopropanol, etc.), etc.], and may be mixed solvents.
• aqueous solvents eg, alcohols (eg, methanol, ethanol, isopropanol, etc.), etc.
• solvents may be mixed solvents.
• the concentration of the polymer (copolymer) is, for example, about 0.001% by mass or more, preferably 0.005% by mass or more, and more preferably about 0.01% by mass or more. may be It can be used after being diluted as appropriate, and the upper limit of the concentration is not particularly limited. It may be 10% by mass or less, 5% by mass or less, 3% by mass or less, 2% by mass or less, or 1% by mass or less.
• the pH for example, pH at 25 ° C.
• the pH is not particularly limited, and may be in the acidic range, the neutral range, or the alkaline range.
• the (weak) acidic to (weak) alkaline range such as 3 to 11, 4 to 10, 5 to 9, 6 to 8, 3 to 8, 3 to 7, 4 to 8, 4.5 ⁇ 7.5, 5 ⁇ 7, 4 ⁇ 6.5, etc. may be used.
• the pH may be, for example, 11 or less, 10 or less, or 9 or less.
• Such a pH is preferable in that the polymer tends to exhibit sufficient water solubility and the amount that can effectively act in an aqueous solution is reduced.
• the lower limit of the pH may be 2 or more, 3 or more, or 4 or more. Such a lower limit is preferable in that the degree of cationization can be appropriately adjusted and the hydrophobic site can efficiently act on the envelope.
• such a pH is suitable from the viewpoint of stability when blended into prescriptions and irritation when in contact with the living body.
• the anti-coronavirus agent of the present invention may optionally include additive components, such as oily bases, which are generally blended in pharmaceuticals, quasi-drugs, cosmetics, laundry detergents, sundries such as packs and sheet masks, and sanitary products.
• additive components such as oily bases, which are generally blended in pharmaceuticals, quasi-drugs, cosmetics, laundry detergents, sundries such as packs and sheet masks, and sanitary products.
• agents moisturizing agents, texture improvers, surfactants, polymers, thickening/gelling agents, solvents, propellants, antioxidants, reducing agents, oxidizing agents, preservatives/antibacterial agents other than the antiseptic and antibacterial agents of the present invention agents, chelating agents, pH adjusters, acids, alkalis, powders, inorganic salts, ultraviolet absorbers, whitening agents, vitamins and their derivatives, anti-inflammatory agents, anti-inflammatory agents, hair growth agents, blood circulation promoters, stimulation agents, hormones, anti-wrinkle agents, anti-aging agents, tightening agents, cooling agents, warming agents, wound healing accelerators, stimulant relievers, analgesics, cell activators, plant/animal/microorganism extracts, antipruritic agents, Keratin exfoliating/dissolving agents, antiperspirants, cooling agents, astringents, enzymes, nucleic acids, fragrances, pigments, colorants, dyes, pigments, various types of water, and the like can
• the anti-coronaviral agent of the present disclosure can be used as an additive for the purpose of imparting antiviral properties.
• it can be used for pharmaceuticals, quasi-drugs, cosmetics, miscellaneous goods such as packs and sheet masks, laundry detergents, sanitary products, and the like.
• it can be added according to a formulation method suitable for each use.
• it can be a solution dissolved in various solvents, an emulsified state, a gel state, a foam state, a spray state, or a state in which a sheet is impregnated.
• the anti-coronavirus agent of the present disclosure may be applied to a substrate to form a film having anti-coronavirus properties, and a laminate having an anti-coronavirus effect may be obtained.
• the type of base material is not particularly limited as long as it plays a role in supporting the anti-coronavirus agent.
• the substrate may constitute a part of various devices (for example, a front plate).
• the shape of the substrate is not particularly limited, but includes plate-like, film-like, sheet-like, tube-like, fibrous, and particulate shapes.
• the morphology of the substrate surface on which the anti-coronavirus film is placed is not particularly limited, and includes flat surfaces, concave surfaces, convex surfaces, combinations thereof, and the like.
• Materials constituting the substrate are not particularly limited, and examples thereof include wood, metal, glass, ceramics, and plastic (resin). Among them, plastic is preferable in terms of handleability. In other words, a resin substrate is preferred.
• methods for applying an anti-coronavirus agent to the surface of a substrate include a spray method, a wire bar coating method, an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, an inkjet method, and a die coating method. be done.
• a method of using the anti-coronavirus agent of the present disclosure to suppress the growth of coronavirus or a method of suppressing coronavirus is a preferred embodiment, and it is particularly preferred to use the anti-coronavirus agent for SARS-CoV-2.
• the antiviral activity value of the anti-coronavirus agent of the present disclosure is preferably 1 or more (especially more than 1), more preferably 1.5 or more, even more preferably 2 or more, and may be 3 or more.
• the antiviral activity value of the present disclosure can be calculated by measuring the virus infectivity titer by the plaque method and using the following formula.
• Antiviral activity value Log (virus infectivity titer of control) - Log (viral infectivity titer of anti-coronaviral agent)
• the control can be selected as appropriate, and examples thereof include water, saline, buffer solutions (eg, PBS), and the like.
• the above antiviral activity value may be achieved in a relatively short period of time (eg, within 10 minutes, 20 minutes, 30 minutes, etc.).
• the antiviral activity value as described above may be maintained for a long period of time, for example, for a long period of time (e.g., 1 hour or more, 1.5 hours or more, 2 hours or more, 6 hours or more, 12 hours or more, 1 day or more, 3 days or more, 7 days or more, 10 days or more, etc.).
• a long period of time e.g., 1 hour or more, 1.5 hours or more, 2 hours or more, 6 hours or more, 12 hours or more, 1 day or more, 3 days or more, 7 days or more, 10 days or more, etc.
• ⁇ Method for measuring solid content of polymer About 1 g of the obtained polymer solution was weighed and dried in a hot air dryer at 200° C. for 15 minutes. The mass of the residue was defined as the solid content, and the ratio to the mass before drying was expressed in %. ⁇ pH measurement method> The value at 25° C. was measured with a pH meter (“F-72” manufactured by Horiba Ltd.).
• Monomer solution 1 consisting of, ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., referred to as EMA) monomer solution 2 consisting of 40.0 g, 2,2'-azobis (2-methylpropionamidine) dihydrochloride (Fujifilm
• An aqueous initiator solution consisting of 36.6 g of a 3% aqueous solution (V-50 manufactured by Wako Pure Chemical Industries, Ltd.) was dropped from separate dropping nozzles. Dropping of the monomer solutions 1 and 2 and the aqueous initiator solution was started at the same time, and the monomer solution 1 was dropped for 180 minutes, the monomer solution 2 for 170 minutes, and the aqueous initiator solution for 210 minutes.
• the reaction solution was kept at 90° C. for an additional 30 minutes for aging to complete the polymerization. got The resulting copolymer had a solid content of 19.8%, a pH of 9.0 and a weight average molecular weight of 48,000. Pure water and citric acid monohydrate were added to the obtained copolymer 1 and stirred to prepare a 2% copolymer aqueous solution having a pH of 6.
• Monomer solution 1 consisting of, ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., referred to as EMA) monomer solution 2 consisting of 40.0 g, 2,2'-azobis (2-methylpropionamidine) dihydrochloride (Fujifilm
• aqueous initiator solution consisting of 27.9 g of a 10% aqueous solution (V-50 manufactured by Wako Pure Chemical Industries, Ltd.) was dropped from separate dropping nozzles. Dropping of the monomer solutions 1 and 2 and the aqueous initiator solution was started at the same time, and the monomer solution 1 was dropped for 180 minutes, the monomer solution 2 for 170 minutes, and the aqueous initiator solution for 210 minutes.
• the reaction solution was kept at 90° C. for an additional 30 minutes for aging to complete the polymerization. got The obtained copolymer had a solid content of 19.8%, a pH of 9.1 and a weight average molecular weight of 20,000. Pure water and citric acid monohydrate were added to the obtained copolymer 2 and stirred to prepare a 2% copolymer aqueous solution having a pH of 6.
• a monomer solution 1 consisting of, a monomer solution 2 consisting of 10.0 g of ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., referred to as EMA), and 32.7 g of acetic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 2, 2 '-Azobis(2-methylpropionamidine) dihydrochloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., referred to as V-50) 26.4 g of a 2.5% aqueous solution of initiator was dropped from separate dropping nozzles. did.
• EMA ethyl methacrylate
• V-50 2, 2 '-Azobis(2-methylpropionamidine) dihydrochloride
• a monomer solution 1 consisting of, a monomer solution 2 consisting of 10.0 g of ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., referred to as EMA), and 32.7 g of acetic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 2, 2 '-Azobis(2-methylpropionamidine) dihydrochloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., referred to as V-50) 5.0% aqueous initiator solution consisting of 42.4 g of aqueous solution was dropped from separate dropping nozzles. did.
• the monomer solutions 1 and 2 acetic acid, and the aqueous initiator solution started dropping at the same time, and the monomer solution 1 was dropped for 180 minutes, the monomer solution 2 for 180 minutes, the acetic acid for 180 minutes, and the aqueous initiator solution for 210 minutes. .
• the reaction solution was kept at 90° C. for 30 minutes for maturation, and after polymerization was completed, 214.2 g of pure water was added to obtain copolymer 4.
• the obtained copolymer had a solid content of 20.4%, a pH of 5.7 and a weight average molecular weight of 18,000. Pure water was added to the obtained copolymer 4 and stirred to prepare a 2% copolymer aqueous solution.
• Monomer solution 1 consisting of, ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., referred to as EMA) monomer solution 2 consisting of 20.0 g, 2,2'-azobis (2-methylpropionamidine) dihydrochloride (Fujifilm
• aqueous initiator solution consisting of 34.2 g of a 3% aqueous solution (V-50 manufactured by Wako Pure Chemical Industries, Ltd.) was dropped from separate dropping nozzles.
• the monomer solutions 1 and 2 and the aqueous initiator solution started dropping at the same time, the monomer solution 1 was dropped for 180 minutes, the monomer solution 2 for 180 minutes, and the aqueous initiator solution for 210 minutes. After the completion of all dropping, the reaction solution was kept at 90° C. for an additional 30 minutes for aging to complete the polymerization. got The resulting copolymer had a solid content of 26.6%, a pH of 9.5 and a weight average molecular weight of 52,000. Pure water and citric acid monohydrate were added to the obtained copolymer 5 and stirred to prepare a 2% copolymer aqueous solution having a pH of 6.
• Monomer solution 1 consisting of, ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., referred to as EMA) monomer solution 2 consisting of 20.0 g, 2,2'-azobis (2-methylpropionamidine) dihydrochloride (Fujifilm
• aqueous initiator solution consisting of 37.7 g of a 10% aqueous solution (V-50 manufactured by Wako Pure Chemical Industries, Ltd.) was dropped from separate dropping nozzles.
• the monomer solutions 1 and 2 and the aqueous initiator solution started dropping at the same time, the monomer solution 1 was dropped for 180 minutes, the monomer solution 2 for 180 minutes, and the aqueous initiator solution for 210 minutes. After the completion of all dropping, the reaction solution was kept at 90° C. for an additional 30 minutes for aging to complete the polymerization. got The resulting copolymer had a solid content of 26.3%, a pH of 9.2 and a weight average molecular weight of 15,000. Pure water and citric acid monohydrate were added to the obtained copolymer 6 and stirred to prepare a 2% copolymer aqueous solution having a pH of 6.
• compositions and solubility parameters [Hildebrand solubility parameter (SP value), Hansen solubility parameter (HSP value, ⁇ p, ⁇ h, ⁇ )] of the copolymers obtained in Production Examples 1 to 6 are shown in the table below. Hansen Solubility Parameters of each monomer used values extracted from Hansen Solubility Parameters: A User's Handbook.
• Anti-coronavirus test 1 Antiviral testing was performed according to ASTM E1052—Standard Test Method for Evaluating Activity of Fungicides against Viruses in Suspensions—. A purified novel coronavirus (SARS-CoV-2) was used as the test virus solution.
• SARS-CoV-2 novel coronavirus
• Example 1 0.1 ml of the test virus solution and 0.9 ml of the test solution were mixed and gently shaken at room temperature for a certain period of time. Thereafter, 9.0 ml of SCDLP medium was added to prepare a 10-fold dilution series, which was added to Vero E6 cells (ATCC CCL-1586) as host cells and cultured for 3 days. The virus infectivity titer after the action was determined by the plaque method.
• the 2% aqueous copolymer solution obtained in Production Example 1 was further diluted with water so that the polymer (copolymer) concentration was 0.1% by mass as a test solution, and PBS (phosphate buffered saline) was added. water) was used as a control.
• PBS was prepared by dissolving 8 g of sodium chloride, 0.2 g of potassium chloride, 1.44 g of disodium hydrogen phosphate, and 0.24 g of potassium dihydrogen phosphate in water, adjusting the pH to 7.4, and making up to 1 L. (same below).
• the antiviral activity value was derived from the following formula.
• Antiviral activity value Log (virus infectivity value of control) - Log (virus infectivity value of test solution of Example 1)
• Table 2 shows the virus infectivity value and antiviral activity value of the test solution of Example 1.
• Example 1 of the present invention had an antiviral activity value of 2.0 after 1 hour, confirming that it had a sufficient anti-coronavirus effect.
• the anti-coronavirus agent of the present disclosure has an increased anti-virus activity value as the elapsed time increases, and can maintain its anti-coronavirus effect.
• Anti-coronavirus test 2 Antiviral testing was performed according to ASTM E1052—Standard Test Method for Evaluating Activity of Fungicides against Viruses in Suspensions—. Porcine coronavirus (PED) was used as the test virus solution.
• PED Porcine coronavirus
• Table 3 shows the virus infectivity value and antiviral activity value of each test solution in Examples 2-7.
• copolymers used in Examples 1 to 7 have anti-coronavirus effects, as described above, as well as water-soluble properties and compatibility with various other ingredients (cosmetics or cosmetic ingredients, etc.) ( Ease of formulation, dispersibility), moisturizing properties when applied to the skin, etc., were also good, and water resistance and antifouling properties when applied to the application (formed coating film) were also excellent.

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