Method for imparting antiviral properties to cured product

Abstract

To provide a method for imparting antiviral properties to a cured product in which a cured product with excellent antiviral properties can be formed as a countermeasure to virus infection.SOLUTION: A method for imparting antiviral properties to a cured product in which antiviral properties are imparted to a cured product by using cationic polymerization initiator containing monosulfonium salt or iodonium salt. It is preferable that the cationic polymerization initiator have (CF3SO2)3C- or (C6F5)4B- as anion. It is also preferable that the cured product be formed by curing a composition containing the cationic polymerization initiator and a curable component. It is also preferable that the curable component contain epoxy compound. It is also preferable that the content of the cationic polymerization initiator be 0.1 pts.mass or more and 20 pts.mass or less in solid content 100 pts.mass of the composition.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for imparting antiviral properties to a cured product. [Background technology]

[0002] In recent years, viral infections have become a threat. For example, SARS-CoV-2, which emerged in 2019, spread worldwide in 2020, infecting more than 600 million people by December 2022 and causing many deaths. In addition, there were outbreaks of viral infections with a high risk of becoming severe, such as the severe acute respiratory syndrome coronavirus in 2002 and the Middle East respiratory syndrome coronavirus in 2012. In addition, there are regular outbreaks of infectious diseases caused by adenovirus, norovirus, influenza virus, etc.

[0003] As a countermeasure against viral infection, for example, attempts have been made to impart antiviral properties to the article, thereby reducing the number of viruses adhering to the article. Patent Document 1 proposes a thermosetting resin composition containing a specific quaternary ammonium salt as an antiviral agent. Patent Document 2 proposes a composition consisting of a resin, monovalent copper compound particles coated with a dispersant, and a hydrophilic compound. Patent Document 3 relates to a method for preparing an antiviral surface, and proposes a cured polymer composition containing one or more polymers and one or more photosensitizers (xanthene photosensitizers). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2023-002258 A [Patent Document 2] International Publication No. 2019 / 045110 [Patent Document 3] International Publication No. 00 / 78854 Summary of the Invention [Problem to be solved by the invention]

[0005] These products have the problem that the quaternary ammonium salt, copper compound particles, or photosensitizer may bleed out from the cured product, and the antiviral effect is not satisfactory. Also, there is a problem that the antiviral effect decreases when stored for a long period of time.

[0006] The present invention has been made in consideration of the above circumstances, and has an object to provide a method for imparting antiviral properties to a cured product, which can form a cured product having excellent antiviral properties as a countermeasure against viral infection. [Means for solving the problem]

[0007] Means for Solving the Problems The present inventors conducted intensive research into the causes of the above problems in order to solve the above problems, and as a result, discovered a method for imparting antiviral properties to a cured product by using a specific cationic polymerization initiator, thereby completing the present invention.

[0008] That is, the present disclosure provides a method for imparting antiviral property to a cured product, by using a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt to impart antiviral property to the cured product.

[0009] The cationic polymerization initiator has, as an anion, (CF3SO2)3C - or (C6F5)4B - It is preferred that the compound has the formula:

[0010] The cured product is preferably obtained by curing a composition containing the cationic polymerization initiator and a curable component.

[0011] The composition preferably contains an epoxy compound as the curable component.

[0012] The content of the cationic polymerization initiator in the composition is preferably 0.1 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the solid content of the composition.

[0013] Furthermore, the present invention provides a composition used for imparting antiviral properties to a cured product, the composition comprising a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt and a curable component. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The present disclosure relates to a method for imparting antiviral properties to a cured product. A method for imparting antiviral properties to a cured product will be described in detail below.

[0015] In the present disclosure, the number of carbon atoms in a group specifies the number of carbon atoms in the group after the substitution when a hydrogen atom in the group is replaced with a substituent. For example, when a hydrogen atom in an alkyl group having 1 to 20 carbon atoms is replaced, the number of carbon atoms of 1 to 20 refers to the number of carbon atoms after the hydrogen atom is replaced, not the number of carbon atoms before the hydrogen atom is replaced. In addition, in the present disclosure, the specification of the number of carbon atoms in a group in which a methylene group in a group having a certain number of carbon atoms is replaced with a divalent group specifies the number of carbon atoms in the group after the replacement.

[0016] In the present disclosure, the "solid content of the composition" refers to the content of all components in the composition excluding the solvent.

[0017] A. Composition First, a composition that imparts antiviral properties to a cured product will be described. The above-mentioned "antiviral property" refers to inactivating viruses and reducing the viral infectivity, and the "composition" in the present disclosure refers to a composition that can form a cured product that reduces the viral infectivity (the number of viruses that are infective against cells) by coming into contact with viruses. The above-mentioned virus infectivity is a value measured using the TCID50 method, and an effective value for exhibiting antiviral activity is a reduction rate (inactivation rate) of the virus infectivity of 95% or more, more preferably 99% or more.

[0018] Viruses that are targets of the above-mentioned antiviral properties include enveloped viruses that have a lipid bilayer membrane derived from the cell membrane of a host cell infected with the virus, and non-enveloped viruses that do not have such a lipid bilayer membrane. Examples of the enveloped viruses include Coronaviridae such as human coronavirus 229E, human coronavirus NL63, human coronavirus HKU1, human coronavirus OC43, SARS-CoV, SARS-CoV2, and MERS-CoV; Orthomyxoviridae such as influenza virus; Flaviviridae such as hepatitis C virus, Japanese encephalitis virus, and Zika virus; Paramyxoviridae such as measles virus and human respiratory syncytial virus; Rhabdoviridae such as rabies virus; Bunyaviridae such as Crimean-Congo hemorrhagic fever virus; Filoviridae such as Ebola virus and Marburg virus; Herpesviridae such as chickenpox and varicella-zoster virus; Poxviridae such as smallpox virus; Hepadnaviridae such as hepatitis B virus; Retroviridae such as human immunodeficiency virus and adult T-cell leukemia virus. Examples of the non-enveloped viruses include adenoviruses, coxsackieviruses, polioviruses, noroviruses, and rotaviruses.

[0019] From the viewpoint of excellent inhibitory effect on the infectivity titer, the composition is preferably directed to an enveloped virus, more preferably to a coronavirus, and further preferably to a human coronavirus.

[0020] The composition is characterized by including a cationic polymerization initiator. In addition, the composition preferably includes a curable component so as to be capable of forming a cured product having excellent antiviral properties. Each component of the above composition will now be described.

[0021] A1. Cationic polymerization initiator The cationic polymerization initiator is a compound capable of releasing a substance that initiates cationic polymerization, and is not particularly limited as long as it contains a monosulfonium salt or an iodonium salt, and any existing cationic polymerization initiator can be used. Examples of the cationic polymerization initiator include a photocationic polymerization initiator and a thermal cationic polymerization initiator.

[0022] (a) Photocationic polymerization initiator The photocationic polymerization initiator is a compound capable of releasing a substance that initiates cationic polymerization upon irradiation with light, and is not particularly limited as long as it contains a monosulfonium salt or an iodonium salt, and any existing photocationic polymerization initiator can be used.

[0023] (a-1) Monosulfonium salt The monosulfonium salt refers to a compound having one sulfonio group. The monosulfonium salt includes, for example, a compound represented by the following general formula (1).

[0024] [ka] (In general formula (1), R 1 represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 10 carbon atoms, an alkoxy group having from 1 to 10 carbon atoms, or a group represented by the following general formula (2): X - represents a monovalent counter anion corresponding to the cation moiety, R 2 , R 3 and R 4 each independently represents a halogen atom or an alkyl group having 1 to 10 carbon atoms, m1 is R 2 represents an integer between 0 and 4, m2 is R 3 represents an integer between 0 and 5, m3 is R 4 represents an integer between 0 and 5, R2 , R 3 or R 4 If there are multiple, multiple R 2 , R 3 or R 4 may be different groups.)

[0025] [ka] In the general formula (2), A represents an oxygen atom, a sulfur atom, or -CO-; R 21 , R 22 , R 23 , R 24 and R 25 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 10 carbon atoms, or an aromatic group having from 6 to 20 carbon atoms; * represents a bond.)

[0026] R in the above general formula (1) 1 , R 2 , R 3 and R 4 and R in general formula (2) 21 , R 22 , R 23 , R 24 and R 25 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0027] R in the above general formula (1) 1 , R 2 , R 3 and R 4 and R in general formula (2) 21 , R 22 , R 23 , R 24 and R 25 The alkyl group having 1 to 10 carbon atoms represented by the following formula may be linear or branched. Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 2-pentyl, 3-pentyl, n-hexyl, heptyl, 2-heptyl, 3-heptyl, octyl, 2-ethylhexyl, nonyl, and decyl groups.

[0028] R in the above general formula (1) 1 The alkoxy group having 1 to 10 carbon atoms represented by the formula (1) may be linear or branched. Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentyloxy group, an isopentyloxy group, a neopentyloxy group, a 2-pentyloxy group, a 3-pentyloxy group, a hexyloxy group, a heptyloxy group, a 2-heptyloxy group, a 3-heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, and a decyloxy group.

[0029] R in the above general formula (2) 21 , R 22 , R 23 , R 24 and R 25 An example of the aromatic group having 6 to 20 carbon atoms represented by the formula (1) is an aryl group. This aryl group may be linked to the benzene ring or another aryl group in formula (2) via a carbonyl group, an ester group, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination of these. In addition, some or all of the hydrogen atoms in the aryl group may be substituted with halogen atoms, cyano groups, or nitro groups. Examples of the aromatic group having 6 to 20 carbon atoms include a phenyl group, a tolyl group, a naphthyl group, a phenylcarbonyl group, a phenyl ester group, a phenyl ether group, a phenyl thioether group, etc. In these groups, some or all of the hydrogen atoms of the phenyl group may be substituted with a halogen atom, a cyano group, or a nitro group. For example, R in the above general formula (2) 21 , R 22 , R 23 , R 24 and R 25 Each of the aromatic groups having 6 to 20 carbon atoms, represented by the formula (I), can be independently -A'-Ph (Ph represents a phenyl group in which one or more hydrogen atoms on the ring may be substituted with a halogen atom, a cyano group, or a nitro group; A' represents a direct bond, -CO-, -COO-, -OCO-, -O-, or -S-).

[0030] In the compound represented by the above general formula (1), from the viewpoint of being able to easily produce a cured product having excellent antiviral properties, it is preferable that m1, m2, and m3 each independently represent an integer of 0 or more and 3 or less, More preferably, it is an integer between 0 and 2, More preferably, it is an integer of 0 to 1, It is particularly preferred that it is 0. In addition, from the viewpoint of making it possible to easily manufacture cured products with excellent antiviral properties, 1 is a compound represented by formula (2), R 21 , R 22 , R 24 and R 25 is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, More preferably, it is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. A hydrogen atom is particularly preferred.

[0031] X in the above general formula (1) - The monovalent counter anion represented by the formula (1) is a counter ion (anion) of an acid generated by irradiating the monosulfonium salt represented by the formula (1) with active energy rays (visible light, ultraviolet light, electron beam, X-ray, etc.), and is, for example, M(Y) a - , RfSO3 - , (RfSO2)3C - , (RfSO2)2N - , (Rf) b PF 6-b- , (Rx) c BY 4-c - etc. M represents a phosphorus atom, a boron atom, or an antimony atom; Y represents a halogen atom; Rf represents an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom; Rx represents a phenyl group or a phenyl group in which at least one hydrogen atom is substituted with a halogen atom, a trifluoromethyl group, a nitro group, or a cyano group; a is the number of Y's and is an integer of 4 to 6, b is the number of Rf and is an integer of 1 to 5, c is the number of Rx and represents an integer of 1 to 4.

[0032] M(Y)a - As an anion represented by the formula, for example, SbF6 - , PF6 - , BF4 - etc.

[0033] RfSO3 - As an anion represented by the formula, for example, CF3SO3 - , CF3CF2SO3 - , (CF3)2CFSO3 - , CF3CF2CF2SO3 - , (CF3)2CFCF2SO3 - , CF3CF2(CF3)CFSO3 - , (CF3)3CSO3 - , CF3CF2CF2CF2SO3 - etc.

[0034] (RfSO2)3C - As an anion represented by the formula (CF3SO2)3C, for example, - , (CF3CF2SO2)3C - , ((CF3)2CFSO2)3C -, (CF3CF2CF2SO2)3C - , ((CF3)2CFCF2SO2)3C - , (CF3CF2(CF3)CFSO2)3C - , ((CF3)3CSO2)3C - etc.

[0035] (RfSO2)2N - As an anion represented by the formula (CF3SO2)2N, for example, - , (CF3CF2SO2)2N - , ((CF3)2CFSO2)2N - , (CF3CF2CF2SO2)2N - , ((CF3)2CFCF2SO2)2N - , (CF3CF2(CF3)CFSO2)2N - , ((CF3)2CFCF2SO2)2N - , (CF3CF2(CF3)CFSO2)2N - , ((CF3)3CSO2)2N - etc.

[0036] (Rf) b PF 6-b - As an anion represented by the formula (CF3CF2)2PF4, for example, - , (CF3CF2)3PF3 - , ((CF3)2CF)2PF4 - , ((CF3)2CF)3PF3 - , (CF3CF2CF2)2PF4 - , (CF3CF2CF2)3PF3 - , ((CF3)2CFCF2)2PF4 - , ((CF3)2CFCF2)3PF3 - , (CF3CF2CF2CF2)2PF4 - or (CF3CF2CF2CF2)3PF3 - Examples of the anion include those represented by the following formula:

[0037] (Rx) c BY 4-c -As an anion represented by the formula (C6F5)4B - , ((CF3)2C6H3)4B - , (CF3C6H4)4B - , (C6F5)2BF2 - , C6F5BF3 - or (C6H3F2)4B - Examples of the anion include those represented by the following formula:

[0038] In the compound represented by the above general formula (1), the counter ion is preferably BF4 - , B(C6F5)4 - , SbF6 - , SbCl6 - , SbF4 - , FSO3 - , AsF6 - , PF6 - , CF3SO3 - , CF3(CF2)3SO3 - , (CF3SO2)3C - , (CF3SO2)2N - Preferably, B(C6F5)4 - , SbF6 - , SbCl6 - , SbF4 - , FSO3 - , AsF6 - , PF6 - , CF3SO3 - , CF3(CF2)3SO3 - , C(CF3SO2)3 - More preferably, B(C6F5)4 - , SbF6 - , SbCl6 - , SbF4 - , FSO3 - , AsF6 - , PF6 - , CF3SO3 - , CF3(CF2)3SO3 - , (CF3SO2)3C - It is more preferred that B(C6F5)4- , SbF6 - , PF6 - , CF3SO3 - , CF3(CF2)3SO3 - , (CF3SO2)3C - It is particularly preferred that B(C6F5)4 - or (CF3SO2)3C - It is most preferred that:

[0039] In the compound represented by the above general formula (1), the counter ion is preferably (RfSO2)3C from the viewpoint of easily producing a cured product having excellent antiviral properties. - Or (Rx) c BY 4-c - It is preferred that B(C6F5)4 - or (CF3SO2)3C - It is more preferable that:

[0040] Examples of the compound represented by the above general formula (1) include Triphenylsulfonium tetrafluoroborate, triphenylsulfonium tris(pentafluoroethyl)trifluorophosphate, triphenylsulfonium tetrakis(pentafluorophenyl)borate, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium tris(trifluoromethylsulfonyl)methanide, triphenylsulfonium bis(trifluoromethylsulfonyl)amide, diphenyl-4-methylphenylsulfonium tetrafluoroborate, diphenyl-4-methylphenylsulfonium tris(pentafluoroethyl)trifluorophosphate, diphenyl-4-methylphenylsulfonium tetrakis(pentafluorophenyl)borate, diphenyl-4-methylphenylsulfonium trifluoromethanesulfonate, diphenyl-4-methylphenylsulfonium hexafluoroantimonate, diphenyl-4-methylphenylsulfonium hexafluorophosphate, diphenyl Diphenyl-4-methylphenylsulfonium tris(trifluoromethylsulfonyl)methanide, diphenyl-4-methylphenylsulfonium bis(trifluoromethylsulfonyl)amide, tri-p-tolylsulfonium tetrafluoroborate, tri-p-tolylsulfonium tris(pentafluoroethyl)trifluorophosphate, tri-p-tolylsulfonium tetrakis(pentafluorophenyl)borate, tri-p-tolylsulfonium trifluoromethanesulfonate, tri-p-tolylsulfonium hexafluoroantimonate trifluoromethylsulfonium hexafluorophosphate, trifluoromethylsulfonium tris(trifluoromethylsulfonyl)methanide, trifluoromethylsulfonium bis(trifluoromethylsulfonyl)amide, diphenyl((4-phenylthio)phenyl)sulfonium tetrafluoroborate, diphenyl((4-phenylthio)phenyl)sulfonium tris(pentafluoroethyl)trifluorophosphate, diphenyl((4-phenylthio)phenyl)sulfonium tetrakis(pentafluorophenyl)borate,Diphenyl((4-phenylthio)phenyl)sulfonium = trifluoromethanesulfonate, diphenyl((4-phenylthio)phenyl)sulfonium = hexafluoroantimonate, diphenyl((4-phenylthio)phenyl)sulfonium = hexafluorophosphate, diphenyl((4-phenylthio)phenyl)sulfonium = tris(trifluoromethylsulfonyl)methanide, diphenyl((4-phenylthio)phenyl)sulfonium = bis(trifluoromethylsulfonyl)amide, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium = tetrafluoroborate, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium = tris(pentafluoroethyl)trifluorophosphate, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium = tetrakis(pentafluorophenyl)borate, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium = trifluoromethanesulfonate, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium = hexafluorophosphate Fluoroantimonate, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium hexafluorophosphate, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium tris(trifluoromethylsulfonyl)methanide, (4-benzoylphenyl)bis(4-fluorophenyl)sulfonium bis(trifluoromethylsulfonyl)amide, (4-phenoxyphenyl)diphenylsulfonium tetrafluoroborate, (4-phenoxyphenyl)diphenylsulfonium tetrakis Examples of the sulfonyl group include (4-phenoxyphenyl)diphenylsulfonium tris(pentafluorophenyl)borate, (4-phenoxyphenyl)diphenylsulfonium trifluoromethanesulfonate, (4-phenoxyphenyl)diphenylsulfonium hexafluoroantimonate, (4-phenoxyphenyl)diphenylsulfonium hexafluorophosphate, (4-phenoxyphenyl)diphenylsulfonium tris(trifluoromethylsulfonyl)methanide, and (4-phenoxyphenyl)diphenylsulfonium bis(trifluoromethylsulfonyl)amide.

[0041] Examples of commercial products of the compound represented by the above general formula (1) include TS-01, TS-91 (all manufactured by Sanwa Chemical Co., Ltd.), CPI-100P, CPI-101A, CPI-200K, CPI-100B, CPI-310B, CPI-310FG, VC-1S, VC-1FG, CPI-410S, CPI-410B, ES-1B (all manufactured by San-Apro Co., Ltd.); WPAG-336, WPAG-367, WPAG-370, WPAG- 469 (all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), TR-PAG-201 / 201S, TR-PAG-202 / 202S, TR-PAG-20101, TR-PAG-20108 (all manufactured by TRONLY); UVI-6992, UVI-6976 (all manufactured by The Dow Chemical Company); ADEKA ARCLES SP-170, ADEKA ARCLES SP-292, ADEKA ARCLES SP-295 (all manufactured by ADEKA Corporation), Ominicat 270 (manufactured by IGM Resins BV), and the like.

[0042] (a-2) Iodonium salts The iodonium salt may be any compound known as a photoacid generator, and examples thereof include compounds represented by the following general formula (3).

[0043] [ka] (In general formula (3), R 31 and R 32 each independently represents a halogen atom, an alkyl group having from 1 to 10 carbon atoms, or an alkoxy group having from 1 to 10 carbon atoms, X - represents a monovalent counter anion corresponding to the cation moiety, m4 is R 31 represents an integer between 0 and 5, m5 is R 32 represents an integer between 0 and 5, R 31 or R 32 If there are multiple, multiple R 31 or R 32may be different groups.)

[0044] R in the above general formula (3) 31 or R 32 The halogen atom represented by the formula (1) is R 1 Examples of halogen atoms include the same groups as those represented by the following formula (1):

[0045] R in the above general formula (3) 31 or R 32 The alkyl group having 1 to 10 carbon atoms represented by the formula (1) is R 1 Examples of the alkyl group include the alkyl group having 1 to 10 carbon atoms, represented by the following formula: In the above composition, from the viewpoint of easily producing a cured product with excellent antiviral properties, R 31 and R 32 However, each independently, It is preferably an alkyl group having 1 to 5 carbon atoms. More preferably, the alkyl group has 1 to 4 carbon atoms. More preferably, it is an alkyl group having 1 to 3 carbon atoms.

[0046] R in the above general formula (3) 31 or R 32 The alkoxy group having 1 to 10 carbon atoms represented by the formula (1) is R 1 and the like.

[0047] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, m4 and m5 are preferably integers of 1 or more and 3 or less. It is more preferable that the integer is 1 or more and 2 or less. It is more preferable that it is 1.

[0048] X in the above general formula (3) - The monovalent anion corresponding to the cation moiety represented by the formula (1) is X -may be the same group as The compound represented by the above general formula (3) is, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, X - But (RfSO2)3C - Or (Rx) c BY 4-c - It is preferred that (CF3SO2)3C - , (C6F5)4B - It is more preferable that: The definitions of Rf, Rx and Y are as follows: - The definitions of Rf, Rx and Y in the above formula (I) apply.

[0049] Examples of the compound represented by the above general formula (3) include 4-isobutylphenyl-4'-methylphenyliodonium tetrafluoroborate, 4-isobutylphenyl-4'-methylphenyliodonium tetrakis(pentafluorophenyl)borate, 4-isobutylphenyl-4'-methylphenyliodonium trifluoromethanesulfonate, 4-isobutylphenyl-4'-methylphenyliodonium hexafluoroantimonate, 4-isobutylphenyl-4'-methylphenyliodonium hexafluorophosphate, 4-isobutylphenyl-4'- Methylphenyliodonium tris(trifluoromethylsulfonyl)methanide, 4-isobutylphenyl-4'-methylphenyliodonium bis(trifluoromethylsulfonyl)amide, Bis(dodecylphenyl)iodonium tetrafluoroborate, Bis(dodecylphenyl)iodonium trifluoromethanesulfonate, Bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, Bis(dodecylphenyl)iodonium trifluoromethanesulfonate, Bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate Bis(dodecylphenyl)iodonium hexafluoroantimonate, bis(dodecylphenyl)iodonium hexafluorophosphate, bis(dodecylphenyl)iodonium tris[fluorotris(trifluoromethylsulfonyl)]methanide, bis(dodecylphenyl)iodonium bis(trifluoromethylsulfonyl)amide, 4-isopropylphenyl-4'-methylphenyliodonium tetrafluoroborate, 4-isopropylphenyl-4'-methylphenyliodonium trifluoromethanesulfonate, 4 -isopropylphenyl-4'-methylphenyliodonium tetrakis(pentafluorophenyl)borate, 4-isopropylphenyl-4'-methylphenyliodonium trifluoromethanesulfonate, 4-isopropylphenyl-4'-methylphenyliodonium hexafluoroantimonate, 4-isopropylphenyl-4'-methylphenyliodonium hexafluorophosphate, 4-isopropylphenyl-4'-methylphenyliodonium tris(trifluoromethylsulfonyl)methanide,Examples of the iodonium salt include 4-isopropylphenyl-4'-methylphenyliodonium bis(trifluoromethylsulfonyl)amide, bis(4-tertbutylphenyl)iodonium tetrafluoroborate, bis(4-tertbutylphenyl)iodonium trifluoromethanesulfonate, bis(4-tertbutylphenyl)iodonium tetrakis(pentafluorophenyl)borate, bis(4-tertbutylphenyl)iodonium trifluoromethanesulfonate, bis(4-tertbutylphenyl)iodonium hexafluoroantimonate, bis(4-tertbutylphenyl)iodonium hexafluorophosphate, bis(4-tertbutylphenyl)iodonium tris(trifluoromethylsulfonyl)methanide, and bis(4-tertbutylphenyl)iodonium bis(trifluoromethylsulfonyl)amide.

[0050] Commercial examples of the organic iodonium salt represented by the above general formula (3) include Omnicat 250 (manufactured by IGM Resins BV), DPI-105, MPI-103, MPI-105, BBI-101, BBI-102, BBI-103, BBI-105 (all manufactured by Midori Chemical Co., Ltd.), PI2074 (manufactured by Solvay), TR-PAG-30101, TR-PAG-30201, TR-PAG-30401, TR-PAG-30408 ​​(manufactured by Dongguan GKEY Trading Co., Ltd.), and the like.

[0051] From the viewpoint of being able to easily produce a cured product with excellent antiviral properties, it is preferable that the composition contains 4-isobutylphenyl-4'-methylphenyl iodonium salt, 4-isopropylphenyl-4'-methylphenyl iodonium salt, bis(4-tert-butylphenyl)iodonium salt, bis(4-tert-butylphenyl)iodonium salt, or the like.

[0052] (a-3)Other The photocationic polymerization initiator in the above composition may contain a non-monosulfonium salt in addition to a monosulfonium salt or an iodonium salt. In this specification, a non-monosulfonium salt refers to a sulfonium salt that does not fall under the category of a monosulfonium salt. In the present invention, when a monosulfonium salt or an iodonium salt is used in combination with a non-monosulfonium salt, the amount of the non-monosulfonium salt used is preferably 1,000 parts by mass or less, and more preferably 500 parts by mass or less, per 100 parts by mass of the monosulfonium salt or the iodonium salt.

[0053] The composition may contain, in addition to the monosulfonium salt and the iodonium salt, other cationic photopolymerization initiators, such as nonionic cationic photopolymerization initiators. Examples of the nonionic photocationic polymerization initiator include compounds described in JP-A-2022-157602. Examples of commercially available nonionic photocationic polymerization initiators include WPAG-145, WPAG-149, WPAG-170, WPAG-199 (all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), D2963, F0362, M1209, M1245 (all manufactured by Tokyo Chemical Industry Co., Ltd.), ADEKA ARCLES SP-082, ADEKA ARCLES SP-103, ADEKA ARCLES SP-601, ADEKA ARCLES SP-606 (all manufactured by ADEKA Corporation), SIN-11 (manufactured by Sanbo Chemical Research Institute Co., Ltd.), NP-TM2, NP-SE10, NA-CS1 (all manufactured by San-Apro Co., Ltd.), and the like.

[0054] (b) Thermal cationic polymerization initiator The thermal cationic polymerization initiator is a compound that accelerates the curing reaction when the curing temperature is reached, and includes monosulfonium salt and iodonium salt compounds. Examples of the thermal cationic polymerization initiator include the thermal cationic polymerization initiator described in JP-A-2023-24144.

[0055] (c) Cationic polymerization initiator In the above composition, from the viewpoint of being able to easily produce a cured product having excellent antiviral properties, the cationic polymerization initiator is preferably a photocationic polymerization initiator.

[0056] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, the molecular weight of the above cationic polymerization initiator is It is preferable that the number is 200 or more and 3,000 or less. More preferably, it is 500 or more and 2,500 or less. It is more preferable that the number is 1,000 or more and 2,200 or less.

[0057] The content of the cationic polymerization initiator in the composition is not particularly limited. From the viewpoint of easily producing a cured product having excellent antiviral properties, for example, the content of the cationic polymerization initiator per 100 parts by mass of the curable component described later is It is preferably 0.1 parts by mass or more and 20 parts by mass or less, More preferably, the content is 0.5 parts by mass or more and 15 parts by mass or less. More preferably, the content is 1.0 part by mass or more and 10 parts by mass or less. It is particularly preferable that the content is 1.5 parts by mass or more and 5 parts by mass or less. In particular, it is preferred that the content of the monosulfonium salt or iodonium salt, which is a photocationic polymerization initiator, falls within the above-mentioned ranges per 100 parts by mass of the curable component.

[0058] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the cationic polymerization initiator in 100 parts by mass of the solid content of the composition is: It is preferably 0.1 parts by mass or more and 20 parts by mass or less, More preferably, the content is 0.5 parts by mass or more and 15 parts by mass or less. More preferably, the content is 1.0 part by mass or more and 12 parts by mass or less. It is particularly preferable that the amount is 1.5 parts by mass or more and 10 parts by mass or less. In particular, it is preferred that the content of the monosulfonium salt or iodonium salt, which is the photocationic polymerization initiator, falls within the above-mentioned ranges per 100 parts by mass of the solid content of the composition.

[0059] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the cationic polymerization initiator in 100 parts by mass of the composition is It is preferably 0.1 parts by mass or more and 20 parts by mass or less, More preferably, the content is 0.5 parts by mass or more and 15 parts by mass or less. More preferably, the content is 0.7 parts by mass or more and 12 parts by mass or less. It is particularly preferable that the content is 0.8 parts by mass or more and 10 parts by mass or less. In particular, it is preferred that the content of the monosulfonium salt or iodonium salt, which is the photocationic polymerization initiator, falls within the above-mentioned ranges per 100 parts by mass of the composition.

[0060] A2.Curing component The composition can form a cured product having excellent antiviral properties by including a curable component, such as an epoxy compound, an oxetane compound, or an acrylic compound.

[0061] (a) Epoxy compounds The epoxy compound can be a compound having an epoxy group. Compounds having an acrylic group or a methacrylic group are also considered to be epoxy compounds as long as they have an epoxy group. The epoxy compounds may be used in combination of two or more kinds. Examples of the epoxy compound include alicyclic epoxy compounds, aromatic epoxy compounds, and aliphatic epoxy compounds.

[0062] (a-1) Alicyclic epoxy compounds The above-mentioned alicyclic epoxy compound is a compound having at least one alicyclic epoxy group in the molecule, that is, a compound having a cycloalkene oxide structure. The above-mentioned alicyclic epoxy compound may have a plurality of cycloalkene oxide structures in one molecule. The compound having a cycloalkene oxide structure may have an epoxy group other than the cycloalkene oxide structure. In addition, the above-mentioned alicyclic epoxy compound may be used in combination of two or more kinds.

[0063] The cycloalkene oxide structure may be a structure in which an aliphatic ring and an epoxy ring share a part of the ring structure, such as a cyclohexene oxide structure or a cyclopentene oxide structure, which is obtained by epoxidizing a cyclohexene ring-containing compound or a cyclopentene ring-containing compound with an oxidizing agent. In the present disclosure, a compound having an aromatic ring is also considered to fall under the category of the above-mentioned alicyclic epoxy compound so long as it has a cycloalkene oxide structure.

[0064] Among the above-mentioned alicyclic epoxy compounds, examples of compounds having one of the above-mentioned cycloalkene oxide structures include 3,4-epoxycyclohexylmethyl acrylate, 3,4-epoxycyclohexylmethyl methacrylate, dicyclopentadiene diepoxide, dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, and 1,2-epoxy-2-epoxyethylcyclohexane.

[0065] Further, examples of the compound having two cycloalkene oxide structures include a compound having a structure in which two cycloalkene oxide structures are condensed directly or via a cycloalkane structure, and a compound having a structure in which two cycloalkene oxide structures are linked by a linking group. Preferred examples of the compound having a structure in which the above two cycloalkene oxide structures are condensed directly or via a cycloalkane structure include compounds represented by the following general formulas (2-1) to (2-4). Preferred examples of compounds having a structure in which the above two cycloalkene oxide structures are linked by a linking group include compounds represented by the following general formula (2-5). From the viewpoint of enabling easy production of a cured product having excellent antiviral properties, the composition preferably contains, as an alicyclic epoxy compound, one or more of the compounds represented by the following general formulas (2-1) to (2-5).

[0066] [ka]

[0067] (In general formula (2-1), R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 and R 50 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 20 carbon atoms, or an alkoxy group having from 1 to 20 carbon atoms.

[0068] [ka]

[0069] (In general formula (2-2), R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 , R64 , R 65 , R 66 , R 67 and R 68 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 20 carbon atoms, or an alkoxy group having from 1 to 20 carbon atoms.

[0070] [ka]

[0071] (In general formula (2-3), R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86 , R 87 and R 88 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 20 carbon atoms, or an alkoxy group having from 1 to 20 carbon atoms.

[0072] [ka]

[0073] (In general formula (2-4), R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 , R 100 , R 101 , R 102 , R 103 , R 104 , R 105 , R 106, R 107 and R 108 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 20 carbon atoms, or an alkoxy group having from 1 to 20 carbon atoms.

[0074] [ka]

[0075] (In general formula (2-5), R 111 , R 112 , R 113 , R 114 , R 115 , R 116 , R 117 , R 118 , R 119 , R 120 , R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 and R 128 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 20 carbon atoms, or an alkoxy group having from 1 to 20 carbon atoms, X 1 represents a single bond, an alkylene group having from 1 to 6 carbon atoms, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, or a group in which a plurality of these are linked together.

[0076] In general formula (2-5), the above-mentioned "group in which a plurality of these are linked" may refer to a group in which groups other than alkylene groups selected from alkylene groups, carbonyl groups, ether bonds, ester bonds, carbonate groups, and amide groups are linked together so that they are not adjacent to each other. In addition, two or more of the same type of groups may be combined, such as ester bond-alkylene group-ester bond-alkylene group.

[0077] R in the above general formula (2-1) 41 ~R 50R in the above general formula (2-2) 51 ~R 68 R in the above general formula (2-3) 71 ~R 88 R in the above general formula (2-4) 91 ~R 108 and R in the above general formula (2-5) 111 ~R 128 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0078] R in the above general formula (2-1) 41 ~R 50 R in the above general formula (2-2) 51 ~R 68 R in the above general formula (2-3) 71 ~R 88 R in the above general formula (2-4) 91 ~R 108 and R in the above general formula (2-5) 111 ~R 128 Examples of the alkyl group having 1 to 20 carbon atoms, represented by the formula (I), include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, a pentyl group, an isopentyl group, a tert-pentyl group, a hexyl group, a 2-hexyl group, a 3-hexyl group, a heptyl group, a 2-heptyl group, a 3-heptyl group, an isoheptyl group, a tert-heptyl group, an octyl group, an isooctyl group, Examples of the aryl group include an ethyl group, a tert-octyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a decyl group, an n-undecyl group, a 1-methyldecyl group, an n-dodecyl group, a 4-ethyloctyl group, a 1,3,5,7-tetramethyloctyl group, a tridecyl group, a 1-hexylheptyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, and an n-eicosyl group.

[0079] R in the above general formula (2-1) 41 ~R 50 R in the above general formula (2-2) 51 ~R 68 R in the above general formula (2-3) 71 ~R 88R in the above general formula (2-4) 91 ~R 108 and R in the above general formula (2-5) 111 ~R 128 Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an amyloxy group, an isoamyloxy group, a tert-amyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, an isooctyloxy group, a 2-ethylhexyloxy group, a tert-octyloxy group, a nonyloxy group, an isononyloxy group, a decyloxy group, a methyl ... Examples of such groups include an n-alkyloxy group, an isodecyloxy group, an n-undecyloxy group, a 1-methyldecyloxy group, an n-dodecyloxy group, a 4-ethyloctyloxy group, a 1,3,5,7-tetramethyloctyloxy group, an n-tridecyloxy group, a 1-hexylheptyloxy group, an n-tetradecyloxy group, an n-pentadecyloxy group, an n-hexadecyloxy group, an n-heptadecyloxy group, an n-octadecyloxy group, and an n-eicosyloxy group.

[0080] X in the above formula (2-5) 1 Examples of the alkylene group having 1 to 6 carbon atoms represented by the formula (1) include a methylene group, a methylmethine group, an isopropylidene group, a dimethylmethine group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, etc. Some or all of the hydrogen atoms in the alkylene group may be substituted with fluorine atoms.

[0081] X in the above formula (2-5) 1 is a group in which a plurality of groups selected from an alkylene group having 1 to 6 carbon atoms, a carbonyl group, an ether bond, an ester bond, a carbonate group, and an amide group are linked together, X 1 The total number of carbon atoms in the group can be 2 or more and 20 or less. From the viewpoint of easily producing a cured product having excellent antiviral properties, X in the above formula (2-5) 1is preferably a group in which an alkylene group having 1 to 6 carbon atoms is linked to an ester bond, more preferably a group in which an alkylene group having 1 to 4 carbon atoms is linked to an ester bond, and particularly preferably a group in which an alkylene group having 1 to 4 carbon atoms is linked to a single-bonded oxygen atom in an ester bond. In addition, X in the above formula (2-5) 1 is a single bond, X 1 is directly bonded to the carbon atoms to which the carbon atoms are linked. Examples of compounds in which two cycloalkene oxide rings are bonded by such a single bond include compounds represented by the following general formula (2-6).

[0082] [ka]

[0083] Examples of methods for producing the compounds represented by the above general formulas (2-1) to (2-5) include the methods described in Japanese Patent Nos. 5,226,162 and 5,979,631. Among the compounds represented by the above general formula (2-1), examples of commercially available compounds include THI-DE (manufactured by ENEOS Corporation). Among the compounds represented by the above general formula (2-2), a commercially available example is DE-102 (manufactured by ENEOS Corporation). Among the compounds represented by the above general formula (2-3), a commercially available example is DE-103 (manufactured by ENEOS Corporation). Among the compounds represented by the above general formula (2-5), commercially available ones include, for example, Celloxide 2021P, Celloxide 2081P, Celloxide (registered trademark) 8000 (all manufactured by Daicel Corporation), CYRACURE UVR-6128 (manufactured by The Dow Chemical Company), and the like.

[0084] From the viewpoint of easily producing a cured product having excellent antiviral properties, the number of epoxy groups in the alicyclic epoxy compound is preferably It is preferable that the number is 2 or more and 5 or less. More preferably, it is 2 or more and 3 or less. It is more preferable that it is 2. The epoxy number of the alicyclic epoxy compound includes the number of cycloalkene oxide structures and epoxy groups other than the cycloalkene oxide structures.

[0085] In the above composition, from the viewpoint of enabling easy production of a cured product with excellent antiviral properties, it is preferred that the alicyclic epoxy compound contains a compound having a structure in which two cycloalkene oxide structures are directly condensed or a compound having a structure in which two cycloalkene oxide structures are linked via a linking group.

[0086] From the viewpoint of enabling a cured product having excellent antiviral properties to be easily produced, it is preferable that the alicyclic epoxy compound in the composition includes at least one selected from the compounds represented by general formulas (2-1), (2-2), (2-3), (2-4), and (2-5), It is more preferable that the composition contains at least one selected from the compounds represented by the above general formulas (2-1), (2-2) and (2-5), It is more preferable that the composition contains at least one of the compounds represented by the general formulas (2-1) and (2-5), It is particularly preferable that the compound represented by the above general formula (2-5) is contained.

[0087] R in the above general formula (2-1) 41 ~R 50 R in the above general formula (2-2) 51 ~R 68 R in the above general formula (2-3) 71 ~R 88 R in the above general formula (2-4) 91 ~R 108 and R in the above general formula (2-5) 111 ~R 128From the viewpoint of enabling easy production of a cured product with excellent antiviral properties, each of the radicals is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and particularly preferably all of them are hydrogen atoms.

[0088] X in the above general formula (2-5) 1 is preferably a single bond, an alkylene group having from 1 to 6 carbon atoms, an ester bond, or a group in which an alkylene group having from 1 to 6 carbon atoms is linked to an ester bond, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, It is more preferable that the alkylene group is a single bond or a group in which an ester bond is linked to an alkylene group having from 1 to 6 carbon atoms. It is more preferable that the alkylene group is a single bond or a group in which an ester bond is linked to an alkylene group having from 1 to 5 carbon atoms. A group in which an alkylene group having 1 to 4 carbon atoms is linked to an ester bond is particularly preferred.

[0089] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, the molecular weight of the alicyclic epoxy compound is It is preferable that the ratio is 100 or more and 500 or less. More preferably, it is 110 or more and 300 or less, More preferably, it is 120 or more and 280 or less, It is particularly preferable that the ratio is 130 or more and 270 or less. It is most preferable that the ratio is 140 or more and 260 or less.

[0090] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, the epoxy equivalent of the alicyclic epoxy compound is Preferably, it is 50 g / eq. or more and 200 g / eq. or less. More preferably, it is 60 g / eq. or more and 150 g / eq. or less. It is more preferable that the elastic modulus is 70 g / eq. or more and 130 g / eq. or less.

[0091] When the composition contains the alicyclic epoxy compound, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the content of the alicyclic epoxy compound in 100 parts by mass of the curable component is It is preferably 10 parts by mass or more and 99 parts by mass or less, More preferably, the content is 20 parts by mass or more and 95 parts by mass or less. More preferably, the content is 30 parts by mass or more and 93 parts by mass or less. It is particularly preferable that the content is 35 parts by mass or more and 91 parts by mass or less. The most preferred range is 40 parts by weight or more and 90 parts by weight or less.

[0092] When the composition contains the alicyclic epoxy compound, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the content of the alicyclic epoxy compound per 100 parts by mass of the solid content of the composition is: It is preferably 10 parts by mass or more and 99 parts by mass or less, More preferably, the content is 20 parts by mass or more and 95 parts by mass or less. More preferably, the content is 30 parts by mass or more and 93 parts by mass or less. It is particularly preferable that the content is 35 parts by mass or more and 90 parts by mass or less. The most preferred range is 40 parts by weight or more and 85 parts by weight or less.

[0093] When the composition contains the alicyclic epoxy compound, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the content of the alicyclic epoxy compound in 100 parts by mass of the composition is It is preferably 10 parts by mass or more and 99 parts by mass or less, More preferably, the content is 20 parts by mass or more and 95 parts by mass or less. More preferably, the content is 30 parts by mass or more and 93 parts by mass or less. It is particularly preferable that the content is 35 parts by mass or more and 90 parts by mass or less. The most preferred range is 40 parts by weight or more and 85 parts by weight or less.

[0094] (a-2) Aromatic epoxy compounds The aromatic epoxy compound refers to an epoxy compound that contains an aromatic ring and does not contain a cycloalkene oxide structure. The aromatic epoxy compound may have a plurality of epoxy groups. The aromatic epoxy compound may be used in combination of two or more kinds. The aromatic ring constituting the aromatic epoxy compound is not particularly limited as long as it is a ring having aromaticity, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. In the above composition, from the viewpoint of being able to easily produce a cured product with excellent antiviral properties, the above aromatic ring is preferably a benzene ring.

[0095] Examples of the aromatic epoxy compounds include glycidyl ethers of monohydric phenols such as phenol, cresol, and butylphenol, or alkylene oxide adducts thereof; polyglycidyl ethers of polyhydric phenols having at least one aromatic ring or alkylene oxide adducts thereof; phenol novolac type epoxy compounds; glycidyl ethers of phenols having two or more phenolic hydroxyl groups, such as resorcinol, hydroquinone, and catechol; polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, such as benzenedimethanol, benzenediethanol, and benzenedibutanol; polyglycidyl esters of polybasic aromatic compounds having two or more carboxylic acids, such as phthalic acid, terephthalic acid, and trimellitic acid; glycidyl esters of benzoic acids, such as benzoic acid, toluic acid, and naphthoic acid; and epoxidized products of styrene oxide or divinylbenzene. Examples of the alkylene oxide used in the alkylene oxide adduct include ethylene oxide and propylene oxide.

[0096] From the viewpoint of enabling easy production of a cured product having excellent antiviral properties, the composition preferably contains a compound represented by the following general formula (2-7) or general formula (2-8) as the aromatic epoxy compound.

[0097] [ka]

[0098] (In general formula (2-7), R 130 and R 131 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, r1 and r2 each independently represent a number of 0 to 5, X 2 represents a divalent aromatic hydrocarbon group having an aromatic ring.

[0099] [ka]

[0100] (In general formula (2-8), R 132 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 133 , R 134 , R 135 , R 136 and R 137 each independently represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, or an alkoxy group having from 1 to 4 carbon atoms, r3 represents a number between 0 and 5.)

[0101] R in the above general formula (2-7) 130 ~R 131 R in the above general formula (2-8) 132 ~R 137 The alkyl group having 1 to 4 carbon atoms represented by the formula (2-1) is R 41 In the alkyl group having 1 to 20 carbon atoms, represented by the formula (I) and the like, groups having a specific number of carbon atoms can be mentioned.

[0102] R in the above general formula (2-8) 133 ~R 137 The halogen atom represented by the formula (2-1) is R41 Examples of halogen atoms include the same groups as those represented by the following formula (1):

[0103] R in the above general formula (2-8) 133 ~R 137 The alkoxy group having 1 to 4 carbon atoms represented by the formula (2-1) is R 41 In the alkoxy group having 1 to 20 carbon atoms, represented by the formula (I) or (II), groups having a specific number of carbon atoms can be mentioned.

[0104] X in the above general formula (2-7) 2 Examples of the divalent aromatic hydrocarbon group having an aromatic ring represented by the formula (I) include a group in which two hydrogen atoms have been removed from an aromatic ring, and a group in which a group in which two hydrogen atoms have been removed from an aromatic ring is linked to an alkylene group. In order to facilitate the production of a cured product having excellent antiviral properties, it is preferable that the aromatic ring in the divalent aromatic hydrocarbon group having an aromatic ring is a benzene ring.

[0105] Examples of the divalent aromatic hydrocarbon group having an aromatic ring include groups represented by the following formulas (2-9), (2-10) and (2-11). In the formula, * represents X in the above general formula (2-7). 2 represents the bonding position of the oxygen atom linked to the

[0106] [ka]

[0107] X in the above general formula (2-7) 2 The number of carbon atoms in the alkyl group is preferably 6 or more and 20 or less. More preferably, the number is 6 or more and 18 or less. It is preferable that the number is 10 or more and 16 or less. By setting the value within the above-mentioned range, the composition can form a cured product that exhibits superior antiviral properties.

[0108] Commercially available products of the aromatic epoxy compounds include, for example, Denacol EX-201 (manufactured by Nagase ChemteX); Oxol PG-100, Oxol EG-200, Oxol EG-280, Oxol CG-500 (all manufactured by Osaka Gas Chemicals Co., Ltd.); Epicron 830, Epicron 835, Epicron EXA-830LVP, Epicron HP4032D, Epicron HP4700 (all manufactured by DIC Corporation); EPOX MK R710, EPOX MK R1710 (both manufactured by Air Water); ADEKA RESIN EP-4000, ADEKA RESIN EP-4100E, ADEKA RESIN EP-4900, ADEKA RESIN ED-509E (all manufactured by ADEKA Corporation); and Examples include YX-4000 (manufactured by Mitsubishi Chemical).

[0109] From the viewpoint of easily producing a cured product having excellent antiviral properties, the molecular weight of the aromatic epoxy compound in the composition is It is preferable that the number is 100 or more and 1,000 or less. More preferably, it is 150 or more and 600 or less, More preferably, it is 180 or more and 500 or less, It is particularly preferable that the ratio is 190 or more and 480 or less. It is most preferable that the ratio is 180 or more and 460 or less.

[0110] From the viewpoint of easily producing a cured product having excellent antiviral properties, the composition preferably has an epoxy equivalent of the aromatic epoxy compound of It is preferable that the elastic modulus is 50 g / eq. or more and 500 g / eq. or less. More preferably, it is 70 g / eq. or more and 400 g / eq. or less. More preferably, the elastic modulus is 100 g / eq. or more and 300 g / eq. or less. It is particularly preferable that the elastic modulus is 130 g / eq. or more and 250 g / eq. or less. It is most preferable that the elastic modulus is 150 g / eq. or more and 230 g / eq. or less.

[0111] When the composition contains the aromatic epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the aromatic epoxy compound in 100 parts by mass of the curable component is It is preferably 1 part by mass or more and 99 parts by mass or less, More preferably, the content is 3 parts by mass or more and 90 parts by mass or less. It is more preferable that the content is 5 parts by mass or more and 85 parts by mass or less.

[0112] When the composition contains the aromatic epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the aromatic epoxy compound in 100 parts by mass of the solid content of the composition is: It is preferably 1 part by mass or more and 99 parts by mass or less, More preferably, the content is 5 parts by mass or more and 70 parts by mass or less. More preferably, the content is 8 parts by mass or more and 50 parts by mass or less. It is particularly preferable that the amount is 10 parts by mass or more and 30 parts by mass or less.

[0113] When the composition contains the aromatic epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the aromatic epoxy compound in 100 parts by mass of the composition is It is preferably 1 part by mass or more and 99 parts by mass or less, More preferably, the content is 5 parts by mass or more and 70 parts by mass or less. More preferably, the content is 8 parts by mass or more and 50 parts by mass or less. It is particularly preferable that the amount is 10 parts by mass or more and 30 parts by mass or less.

[0114] (a-3) Aliphatic epoxy compounds The aliphatic epoxy compound refers to an epoxy compound that does not have a cycloalkene oxide structure and an aromatic ring. The aliphatic epoxy compound may have a plurality of epoxy groups (not having a cycloalkene oxide structure) in one molecule. In addition, the aliphatic epoxy compound may be used in combination of two or more kinds.

[0115] Examples of such aliphatic epoxy compounds include aliphatic ring-containing epoxy compounds and chain aliphatic epoxy compounds.

[0116] The aliphatic ring-containing epoxy compound refers to an aliphatic epoxy compound having an aliphatic ring such as an aliphatic hydrocarbon ring or an aliphatic heterocycle. The aliphatic hydrocarbon ring may be any ring-forming atom that is carbon atom only and does not have aromaticity. In addition, the aliphatic hydrocarbon ring may have one or more hydrogen atoms substituted with a linear or branched alkyl group having 1 to 4 carbon atoms. Examples of such aliphatic hydrocarbon rings include monocyclic aliphatic hydrocarbon rings such as cycloheptane and cyclohexane; A structure in which multiple monocyclic aliphatic hydrocarbon rings are bonded together via a single bond, an alkylene group having from 1 to 4 carbon atoms, a carbonyl group, an ether bond, an ester bond, a carbonate group or an amide group, or a group in which multiple of these are linked together; Examples of the ring include a polycyclic aliphatic hydrocarbon ring having a structure in which two or more monocyclic aliphatic hydrocarbon rings, such as an isobornyl ring, an adamantane ring, a dicyclopentene ring, a dicyclopentane ring, a tricyclodecane ring, a norbornene ring, and a norbornane ring, share one or two or more carbon atoms in the ring.

[0117] The aliphatic heterocycle may be any ring-forming atom that includes an atom other than a carbon atom and does not have aromaticity. Examples of the aliphatic heterocycle include a pyrrolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring, a homopiperidine ring, a homopiperazine ring, a tetrahydropyridine ring, a tetrahydroquinoline ring, a tetrahydroisoquinoline ring, a tetrahydrofuran ring, a tetrahydropyran ring, a dihydrobenzofuran ring, a tetrahydrocarbazole ring, a caprolactam ring, an isocyanuric ring, and a hydantoin ring.

[0118] In the above composition, from the viewpoint of being able to easily produce a cured product having excellent antiviral properties, it is preferable that the aliphatic ring-containing epoxy compound includes a compound represented by the following general formula (2-12).

[0119] [ka] (In general formula (2-12), R 138 and R 139 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, r4 and r5 each independently represent a number of 0 to 5, X 3 represents a divalent aliphatic hydrocarbon ring-containing group.

[0120] Above R 138 and R 139 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (1) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.

[0121] In order to easily produce a cured product having excellent antiviral properties, the composition is characterized in that r4 and r5 are each independently selected from the group consisting of: It is preferably an integer between 0 and 3, More preferably, it is an integer between 0 and 2, More preferably, it is an integer of 0 to 1, It is particularly preferred that it is 0.

[0122] Above X 3 Examples of the group containing a divalent aliphatic hydrocarbon ring represented by the formula (I) include a group in which two hydrogen atoms have been removed from an aliphatic hydrocarbon ring, and a group in which two hydrogen atoms have been removed from an aliphatic hydrocarbon ring are combined with an alkylene group.

[0123] In order to facilitate the production of a cured product having excellent antiviral properties, the divalent aliphatic hydrocarbon ring-containing group in the composition is preferably a group represented by, for example, formula (2-13), (2-14), or (2-15) below. In the following formulas (2-13), (2-14) and (2-15), * represents X in the above general formula (2-12). 3 represents the bonding position of the oxygen atom linked to the

[0124] [ka]

[0125] From the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the composition is Above X 3 The number of carbon atoms in the formula is preferably 6 or more and 20 or less, More preferably, it is 6 or more and 18 or less. It is more preferable that the number is 10 or more and 16 or less.

[0126] The chain aliphatic epoxy compound refers to an aliphatic epoxy compound that does not have an aliphatic hydrocarbon ring, an aromatic ring, or a cycloalkene oxide structure. From the viewpoint of enabling easy production of a cured product having excellent antiviral properties, the composition preferably contains, for example, a compound represented by the following general formula (2-16) as the chain aliphatic epoxy compound.

[0127] [ka]

[0128] (In the above general formula (2-16), L represents a single bond or a methylene group; R 140 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 141 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, Each r6 independently represents a number of 0 to 5, t represents a number between 1 and 4.)

[0129] Above R 140 The alkyl group having 1 to 4 carbon atoms represented by the formula (2-1) is R 41 In the alkyl group having 1 to 20 carbon atoms, such as those represented by the formula (I) and (II), examples include groups having a specific number of carbon atoms.

[0130] Above R 141 The alkyl group having 1 to 20 carbon atoms represented by the formula (2-1) is R 41 The alkyl groups having 1 to 20 carbon atoms are the same as those represented by R 141 If there are multiple R 141 may be the same group or different groups.

[0131] In the above composition, when the above t is a number of 2 or more and 3 or less, from the viewpoint of easily producing a cured product with excellent antiviral properties, 141 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, More preferably, it is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. A hydrogen atom or an alkyl group having 1 to 2 carbon atoms is more preferable.

[0132] In the above composition, when the above t is 1, from the viewpoint of easily producing a cured product having excellent antiviral properties, 141 teeth, It is preferably an alkyl group having 10 to 15 carbon atoms. More preferably, the alkyl group has 11 to 14 carbon atoms. More preferably, it is an alkyl group having 12 to 13 carbon atoms.

[0133] In the above composition, from the viewpoint of easily producing a cured product having excellent antiviral properties, r6 is Preferably, it is a number between 0 and 3, More preferably, it is a number between 0 and 2, More preferably, it is a number between 0 and 1, It is particularly preferred that it is 0.

[0134] When the composition contains the aliphatic epoxy compound, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the content of the aliphatic epoxy compound in 100 parts by mass of the curable component is It is preferably 0.5 parts by mass or more and 80 parts by mass or less, More preferably, the content is 0.8 parts by mass or more and 70 parts by mass or less. More preferably, the content is 1 part by mass or more and 60 parts by mass or less, It is particularly preferable that the content is 1.2 parts by mass or more and 50 parts by mass or less, It is most preferable that the content is 1.5 parts by weight or more and 45 parts by weight or less.

[0135] When the composition contains the aliphatic epoxy compound, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the content of the aliphatic epoxy compound per 100 parts by mass of the solid content of the composition is: It is preferably 1 part by mass or more and 60 parts by mass or less, More preferably, the content is 2 parts by mass or more and 55 parts by mass or less. More preferably, the content is 3 parts by mass or more and 50 parts by mass or less. It is particularly preferable that the content is 4 parts by mass or more and 45 parts by mass or less.

[0136] When the composition contains the aliphatic epoxy compound, from the viewpoint of making it possible to easily produce a cured product having excellent antiviral properties, the content of the aliphatic epoxy compound in 100 parts by mass of the composition is: It is preferably 1 part by mass or more and 60 parts by mass or less, More preferably, the content is 2 parts by mass or more and 55 parts by mass or less. More preferably, the content is 3 parts by mass or more and 50 parts by mass or less. It is particularly preferable that the content is 4 parts by mass or more and 45 parts by mass or less.

[0137] (a-4) Epoxy compounds In the composition, the epoxy compound preferably contains an alicyclic epoxy compound, and at least one of an aromatic epoxy compound and an aliphatic epoxy compound. This is because the composition can form a cured product that exhibits superior antiviral properties.

[0138] When the composition contains an alicyclic epoxy compound and at least one of an aromatic epoxy compound and an aliphatic epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the alicyclic epoxy compound in 100 parts by mass of the epoxy compound is It is preferably 10 parts by mass or more and 95 parts by mass or less, More preferably, the content is 30 parts by mass or more and 90 parts by mass or less. More preferably, the content is 40 parts by mass or more and 85 parts by mass or less. It is particularly preferable that the content is 50 parts by mass or more and 80 parts by mass or less.

[0139] When the composition contains an alicyclic epoxy compound and an aromatic epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the aromatic epoxy compound in 100 parts by mass of the epoxy compound is It is preferably 5 parts by mass or more and 90 parts by mass or less, More preferably, the content is 10 parts by mass or more and 70 parts by mass or less. More preferably, the content is 15 parts by mass or more and 50 parts by mass or less. It is particularly preferable that the content is 20 parts by mass or more and 35 parts by mass or less.

[0140] When the composition contains an alicyclic epoxy compound and an aliphatic epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the aliphatic epoxy compound in 100 parts by mass of the epoxy compound is It is preferably 1 part by mass or more and 50 parts by mass or less, More preferably, the content is 2 parts by mass or more and 40 parts by mass or less. More preferably, the content is 3 parts by mass or more and 30 parts by mass or less, It is particularly preferable that the amount is 3 parts by mass or more and 20 parts by mass or less.

[0141] From the viewpoint of being able to easily produce a cured product having excellent antiviral properties, the composition preferably contains the alicyclic epoxy compound, the aromatic epoxy compound and the aliphatic epoxy compound in a total amount per 100 parts by mass of the curable component, It is preferably 30 parts by mass or more, More preferably, it is 40 parts by mass or more, More preferably, it is 50 parts by mass or more, It is even more preferable that the amount is 60 parts by mass or more, It is particularly preferable that the amount is 70 parts by mass or more. It is particularly preferable that the amount is 80 parts by mass or more. It is particularly preferable that the amount is 90 parts by mass or more. It is particularly preferable that the amount is 99 parts by mass or more. It is most preferable that 100 parts by mass, i.e., the total amount of the curable components, is an epoxy compound.

[0142] When the composition contains the epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the epoxy compound in 100 parts by mass of the solid content of the composition is: It is preferably 30 parts by mass or more and 99 parts by mass or less, More preferably, the content is 50 parts by mass or more and 98 parts by mass or less. More preferably, the content is 55 parts by mass or more and 98 parts by mass or less. It is particularly preferable that the content is 60 parts by mass or more and 98 parts by mass or less.

[0143] When the composition contains the epoxy compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the epoxy compound in 100 parts by mass of the composition is It is preferably 30 parts by mass or more and 99 parts by mass or less, More preferably, the content is 50 parts by mass or more and 98 parts by mass or less. It is preferably 55 parts by mass or more and 98 parts by mass or less, and particularly The content is preferably 60 parts by mass or more and 98 parts by mass or less.

[0144] (b) Oxetane Compounds The above-mentioned oxetane compound refers to a compound having an oxetane group and not having an epoxy group. Compounds having an acrylic group or a methacrylic group are also considered to be oxetane compounds as long as they have an oxetane group and not having an epoxy group. The above-mentioned oxetane compounds may be used in combination of two or more kinds. Examples of the oxetane compound include aromatic oxetane compounds and aliphatic oxetane compounds.

[0145] (b-1) Aromatic oxetane compounds The aromatic oxetane compound refers to an oxetane compound containing an aromatic ring. The aromatic ring is not particularly limited as long as it is a ring having aromaticity, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. In the composition, the aromatic ring is preferably a benzene ring. This is because the composition used in the method of the present disclosure can form a cured product that exhibits superior antiviral properties. The aromatic oxetane compound may have a hydrogen atom substituted with a halogen atom, and may have a silyl group, an ether group, or a thioether group.

[0146] Examples of the aromatic oxetane compound include xylylene bisoxetane, bisphenol A bisoxetane, bisphenol F bisoxetane, bisphenol S bisoxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 1,4-bis[(3-ethyloxetan-3-yl)methoxy]benzene, 1,4-bis[[(3-ethyloxetan-3-yl)methoxy]methyl]benzene, 1,3-bis[(3-ethyloxetan-3-yl)methoxy]methyl]benzene, Examples of such bis[(3-ethyloxetan-3-yl)methoxy]benzene include 1,2-bis[(3-ethyloxetan-3-yl)methoxy]benzene, 4,4'-bis[(3-ethyloxetan-3-yl)methoxymethyl]biphenyl, 2,2'-bis[(3-ethyl-3-oxetanyl)methoxy]biphenyl, and 3,3',5,5'-tetramethyl[4,4'-bis(3-ethyloxetan-3-yl)methoxy]biphenyl.

[0147] (b-2) Aliphatic oxetane compounds The aliphatic oxetane compound is an oxetane compound that does not have an aromatic ring. The aliphatic oxetane compound may have a hydrogen atom substituted with a halogen atom or a hydroxyl group. The aliphatic oxetane compound may have a silyl group, an ether group, or a thioether group.

[0148] Examples of the aliphatic oxetane compound include 3-ethyl-3-oxetanemethanol, di(1-ethyl-3-oxetanyl)methyl ether, 3-ethyl-3-(hexyloxymethyl)oxetane, 3-ethyl-3-n-octyloxymethyloxetane, 3-ethyl-3-dodecyloxymethyloxetane, 3-ethyl-3-(3,7-dodecadienyloxymethyl)oxetane, 3-ethyl-3-n-butyloxymethyloxetane, 3-ethyl-3-{[3-(triethoxysilyl)propoxy]methyl}oxetane, and 3-ethyl-3-cyclohexyloxymethyloxetane. Examples include 2-methoxy-3,3-dimethyloxetane, 1,2-bis[2-{(1-ethyl-3-oxetanyl)methoxy}ethylthio]ethane, and 2,4,6-tris[(3-ethyloxetan-3-yl)methyl]cyanuric acid.

[0149] (c) Acrylic compounds The acrylic compound refers to a compound having an acrylic group or a methacrylic group and not having an epoxy group. In order to obtain good curability of the composition used in the method of the present disclosure, the acrylic compound is preferably a compound having a total of 2 or more functional acrylic and methacrylic groups. Examples of the acrylic compound include polyfunctional (meth)acrylates and polyfunctional (meth)acrylate oligomers. In the present disclosure, (meth)acrylate includes both methacrylate and acrylate.

[0150] Examples of bifunctional (meth)acrylates include (poly)ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 4,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, pentaerythritol di(meth)acrylate, neopentyl glycol dimethacrylate, 3-methyl-1,5 pentanediol diacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, dimethylol tricyclodecane diacrylate, and dicyclopentanyl diacrylate.

[0151] Examples of trifunctional (meth)acrylates include trimethylolpropane tri(meth)acrylate, ethylene oxide-modified trimethylolpropane tri(meth)acrylate, propylene oxide-modified trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, alkyl-modified dipentaerythritol tri(meth)acrylate, tris(2-acryloxyethyl)isocyanurate, and ε-caprolactone-modified tris(2-acryloxyethyl)isocyanurate.

[0152] Examples of the tetrafunctional (meth)acrylate include pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, and alkyl-modified dipentaerythritol tetra(meth)acrylate.

[0153] Examples of the pentafunctional (meth)acrylate include dipentaerythritol penta(meth)acrylate and alkyl-modified dipentaerythritol penta(meth)acrylate.

[0154] Examples of the hexafunctional (meth)acrylate include dipentaerythritol hexa(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0155] From the viewpoint of enabling a cured product with excellent antiviral properties to be easily produced, the composition preferably contains, as the acrylic compound, a compound represented by the following general formula (2-17), which has a skeleton derived from dipentaerythritol and has a total functionality of three or more acrylic and methacrylic groups.

[0156] [ka]

[0157] Above R 201 , R 202 , R203 , R 204 , R 205 and R 206 each independently represents a hydrogen atom, an acryl group, or a methacryl group, provided that the total number of acryl groups and methacryl groups is at least 3.

[0158] The above composition is preferably selected from the group consisting of R 201 , R 202 , R 203 , R 204 , R 205 and R 206 It is more preferable that at least four of the groups are acrylic or methacrylic groups, and particularly Preferably, 5 or 6 are acrylic or methacrylic groups.

[0159] In the composition, the acrylic compound may be an acrylic resin such as a polymer of a monomer selected from an acrylic acid ester and a methacrylic acid ester, or a copolymer of a plurality of such monomers. The acrylic resin may be modified with an oligomer such as polyisoprene, polybutadiene, polyurethane, or polyether. Examples of acrylic resins modified with oligomers include epoxy (meth)acrylate, urethane (meth)acrylate, polyester (meth)acrylate, and polyether (meth)acrylate. In addition, some of the hydrogen atoms in the acrylic resin may be substituted with halogen atoms such as chlorine, fluorine, or bromine.

[0160] Commercially available products of the urethane (meth)acrylate oligomer include, for example, Beamset 102, 502H, 505A-6, 510, 550B, 551B, 575, 575CB, EM-90, and EM92 (all manufactured by Arakawa Chemical Industries, Ltd.); Photomer 6008 and 6210 (all manufactured by San Nopco Co., Ltd.); NK Oligo U-2PPA, U-4HA, U-6HA, H-15HA, UA-32PA, U-324A, U-4H, and U-6H (all manufactured by Shin-Nakamura Chemical Co., Ltd.); Aronix M-1100, M-1200, M-1210, M-1310, M-1600, and M-1960 (all manufactured by Toa Gosei Co., Ltd.); AH-600, AT606, and U A-306H (manufactured by Kyoeisha Chemical Co., Ltd.); Kayarad UX-2201, UX-2301, UX-3204, UX-3301, UX-4101, UX-6 101, UX-7101 (manufactured by Nippon Kayaku Co., Ltd.); Shiko UV-1700B, UV-3000B, UV-6100B, UV-6300B, UV-7000, UV-2010B (manufactured by Nippon Gosei Kagaku Kogyo Co., Ltd.); Art Resin UN-1255, UN-5200, HDP-4T, HMP-2, UN-901T, UN-3320HA, UN-3320HB, UN-3320HC, UN-3320HS, H-61, HDP-M20 (manufactured by Negami Kogyo Co., Ltd.); Ebecryl 6700, 204, 205, 220, 254, 1259, 1290K, 1748, 2002, 2220, 4833, 4842, 4866, 5129, 6602, 8301 (all manufactured by Daicel UCB Ltd.).

[0161] Examples of commercially available epoxy (meth)acrylate oligomers include "CCR-1179" (cresol novolac F type epoxy acrylate), "ZAR-2000" (acid-modified bisphenol type epoxy acrylate: reaction product of bisphenol A type epoxy resin, acrylic acid, and succinic anhydride), "ZFR-1491H" (acid-modified bisphenol type epoxy acrylate: reaction product of bisphenol F type epoxy resin, acrylic acid, and acid anhydride), "ZFR-1533H" (acid-modified bisphenol type epoxy acrylate: reaction product of bisphenol F type epoxy resin, acrylic acid, and tetrahydrophthalic anhydride), "ZCR-1569H" (acid-modified biphenyl type epoxy acrylate: reaction product of biphenyl type epoxy resin, acrylic acid, and acid anhydride), and "PR-300CP" (cresol novolac type epoxy resin, acrylic acid, and acid anhydride) manufactured by Showa Denko K.K.

[0162] When the composition contains the acrylic compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the acrylic compound in 100 parts by mass of the curable component is It is preferably 80 parts by mass or more, More preferably, it is 90 parts by mass or more, More preferably, it is 95 parts by mass or more, It is particularly preferable that the amount is 98 parts by mass or more, It is particularly preferable that the amount is 99 parts by mass or more. It is most preferable that 100 parts by mass, i.e., the total amount of the hardenable component, is an acrylic compound.

[0163] When the composition contains the acrylic compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the acrylic compound in 100 parts by mass of the solid content of the composition is It is preferably 70 parts by mass or more and 99 parts by mass or less, More preferably, the content is 80 parts by mass or more and 97 parts by mass or less. More preferably, the content is 85 parts by mass or more and 96 parts by mass or less. It is particularly preferably from 90 parts by mass to 94 parts by mass.

[0164] When the composition contains the acrylic compound, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the acrylic compound in 100 parts by mass of the composition is It is preferably 10 parts by mass or more and 99 parts by mass or less, More preferably, the content is 20 parts by mass or more and 80 parts by mass or less. More preferably, the content is 30 parts by mass or more and 70 parts by mass or less. It is particularly preferable that the content is 40 parts by mass or more and 60 parts by mass or less. The most preferred range is 45 parts by weight or more and 50 parts by weight or less.

[0165] (d) Curable component From the viewpoint of enabling a cured product having excellent antiviral properties to be easily produced, the total content of the epoxy compound, the oxetane compound, and the acrylic compound contained as curable components in the composition is, based on 100 parts by mass of the solid content of the composition, It is preferably 80 parts by mass or more and 99.9 parts by mass or less, More preferably, the content is 85 parts by mass or more and 99 parts by mass or less. More preferably, the content is 88 parts by mass or more and 98 parts by mass or less. It is particularly preferably from 90 parts by mass to 97.5 parts by mass.

[0166] A3.Other ingredients The composition contains the cationic polymerization initiator and the curable component, and may further contain other components, if necessary. Examples of the other components include various additives such as other polymerizable compounds excluding the above-mentioned curable components; photoradical polymerization initiators, thermal radical polymerization initiators; stabilizers; inorganic compounds; coupling agents; solvents; curing accelerators; leveling agents; colorants such as pigments and dyes; defoamers; thickeners; thixotropic agents; surfactants; flame retardants; plasticizers; antioxidants; polymerization inhibitors; ultraviolet absorbers; antistatic agents; flow adjusters; and adhesion promoters.

[0167] (a) Other polymerizable compounds The composition may contain other polymerizable compounds other than the epoxy compound, the oxetane compound, and the acrylic compound. The other polymerizable compounds are not particularly limited and may be used as long as they are components that are cured by energy ray irradiation. For example, vinyl ether compounds may be mentioned. The vinyl ether compound may be a compound having a vinyl ether structure and not having an epoxy group, an acryl group, or an oxetanyl group. Examples of the vinyl ether compound include compounds described in JP-A-2022-42418.

[0168] (b) Photoradical polymerization initiator When the composition contains the acrylic compound, from the viewpoint of promoting polymerization of the acrylic compound, the composition preferably contains a photoradical polymerization initiator. The type of the photoradical polymerization initiator is not particularly limited, and a conventionally known photoradical polymerization initiator can be used. Examples of the photoradical polymerization initiator include compounds described in JP-A-2022-049375.

[0169] When the composition contains the photoradical polymerization initiator, from the viewpoint of easily producing a cured product having excellent antiviral properties, the content of the photoradical polymerization initiator is, relative to 100 parts by mass of the acrylic compound, It is preferably 0.001 parts by mass or more and 10 parts by mass or less, More preferably, the content is 0.01 parts by mass or more and 5 parts by mass or less. It is particularly preferable that the content is 0.03 part by mass or more and 1 part by mass or less.

[0170] (c) Leveling agent The composition preferably further contains a leveling agent. The leveling agent can have the function of adjusting the fluidity of the composition used in the method of the present disclosure and making the coating film obtained by applying the composition flatter. The leveling agent can be used without particular limitation as long as it can reduce the surface tension of the composition and impart surface orientation. The composition preferably contains a silicone-based compound as a leveling agent, because the composition has a large effect of lowering the surface tension, and this makes it easier to improve repelling and dents in the coating film.

[0171] Examples of the silicone-based compound include silicone, silicone-modified acrylic, polyether-modified polydimethylsiloxane, polyetherester-modified hydroxyl-containing polydimethylsiloxane, polyester-modified hydroxyl-containing polydimethylsiloxane, and polyether-modified polydimethylsiloxane.

[0172] Commercially available leveling agents containing the above silicone-based compounds include: DOWSIL SH-29PA, FZ-2105, 67ADDITIVE, 8618ADDITIVE, 3ADDITIVE, 56ADDITIVE (all manufactured by Dow Corning Toray Co., Ltd.); TEGO Flow 425, TEGO Glide 100, TEGO Glide 110, TEGO Glide 432 (all manufactured by Evonik); F-251, F-253, F-410, F-430, F-444, F-477, F-510, F-551-A, F-552, F-553 , F-554, F-555-A, F-556, F-558, F-559, F-560, F-561, F-562, F-563, F-565 , F-568, F-569, F-570, F-571, F-575, F-576, R-01, R-40, R-40-LM, R-41, R-41-LM, RS-72-A, RS-75-A, RS-75-NS, RS-78, RS-90, DS-21 (manufactured by DIC Corporation); BYK-300, BYK-306, BYK-307, BYK-310, BYK-315, BYK-313, BYK-320, BYK-322, BYK -323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-337, BYK-341, BYK-344, BYK-347 , BYK-348, BYK-349, BYK-370, BYK-375, BYK-377, BYK-378, BYK-UV3500, BYK-UV3510, BYK-UV3570, BYK-3550, BYK-SILCLEAN3700, BYK-SILCLEAN3720 (manufactured by BYK); Polyflow KL-400X, Polyflow KL-400HF, Polyflow KL-401, Polyflow KL-402, Polyflow KL-403, Polyflow KL-404 (all manufactured by Kyoeisha Chemical Co., Ltd.) Examples of the antibacterial agent include KP-323, KP-341, KP-104, KP0110, and KP-112 (all manufactured by Shin-Etsu Chemical Co., Ltd.).

[0173] (d) Solvent The composition may contain a solvent to dissolve the cationic photopolymerization initiator, the curable component, etc. Examples of the solvent include those that do not correspond to either the cationic photopolymerization initiator or the curable component, are liquid at 25°C under atmospheric pressure, and can disperse or dissolve each component in the composition. In addition, the solvent is preferably one that does not react with the curable component contained in the composition, since it has little adverse effect on the cured product of the composition. Specific examples of the solvent include those described in International Publication No. WO2019 / 159953. In addition, in the composition, the solvent may be used alone, or a mixed solvent in which two or more of the solvents are mixed can be used.

[0174] A4.Blending method The method for producing the composition may be any method capable of forming a composition containing the desired amounts of each of the above components, and may include a method using a known mixing means. For example, the composition may be produced by mixing each component using a mixer such as a homodisper, homomixer, universal mixer, planetary mixer, kneader, or three-roll mixer.

[0175] A5.Application The use of the composition is not particularly limited, but it can be used in applications where conventional epoxy resin compositions or (meth)acrylate resin compositions are used. In particular, it is suitable for applications where human body contact is assumed, particularly applications where hand and finger contact is assumed. For example, it is suitable for a wide range of applications such as packaging materials, furniture, home appliances, automobile-related parts, building materials, office supplies, school supplies, sports goods, toys, leather products, toiletries, kitchenware, nursing care products, medical equipment, transportation equipment, and toiletry products, as well as surface coatings thereof. In particular, building materials, office supplies, toiletries, kitchenware, and medical equipment are suitable. Examples of the building materials include wallpaper, wall boards, wall materials, floor materials, handrails, sliding doors, paper screens, and shoe cabinets. The office supplies include file covers, clear files, ring files, calculators, clipboards, finger cots, and the like. Examples of the office automation equipment include keyboard covers, printers, FAX machines, and touch panels of multifunction machines. Examples of the automobile-related members include meter display panels, inner surfaces of glass, steering wheels, glove boxes, sun visors, navigation systems, and ETCs. The furniture includes tables, sofas, mattresses, chairs, desk chairs, curtains, etc. Examples of the toiletries include toothbrushes, toothpaste containers, containers for shampoo, conditioner, body soap, etc., hairbrushes, hair dryers, razors, etc. Examples of the kitchen utensils include cutting boards (including antibacterial cutting boards and antiviral cutting boards); sink mats; and kitchen gloves. It can also be suitably used in various other fields such as other product fields (e.g., sporting goods, school supplies, writing implements, toys, plastic miscellaneous goods), medical and welfare service fields (materials and products used in hospitals, nursing homes, public facilities, etc.), etc.

[0176] B. Cured product Next, the cured product will be described. The cured product is a cured product of the above-mentioned composition.

[0177] Since the method of the present disclosure uses the above-mentioned composition, it is possible to provide a cured product with excellent antiviral properties. The composition of the cured product can be the same as that described in the above section "A. Composition," and therefore a description thereof will be omitted here. The uses of the cured product may be the same as those described in the section "A. Composition" above.

[0178] The method for producing the cured product may be any method capable of curing the composition. The method for producing the cured product may be the method described later in "C. Method for imparting antiviral properties to the cured product."

[0179] C. Method for imparting antiviral properties to a cured product Next, a method for imparting antiviral properties to the above-mentioned cured product will be described. The method for imparting antiviral properties to a cured product is characterized in that, when the cationic polymerization initiator is a photocationic polymerization initiator, it includes a curing step of irradiating the composition with active energy rays.

[0180] It is presumed that by irradiating the composition with active energy rays, the cationic photopolymerization initiator in the composition generates cations, which then cure the composition, thereby imparting antiviral properties to the cured product obtained. One of the features of the method disclosed herein is that it has been found that a specific cationic photopolymerization initiator can impart sufficient antiviral properties to the cured product. When the composition uses a thermal cationic polymerization initiator instead of a photo-cationic polymerization initiator, the composition is heated. In this case, the heating temperature may be the same as the curing temperature when a thermal cationic polymerization initiator is used, which will be described later.

[0181] (a) Curing process This step is a step of curing the composition. This step may be a method capable of polymerizing at least one of the epoxy compound, the acrylic compound, and other polymerizable compounds among the curable components in the composition. For example, when a photocationic polymerization initiator is used as the cationic polymerization initiator, a method of irradiating the coating film formed by applying the composition with active energy rays to polymerize the composition may be mentioned.

[0182] Examples of the light source of the active energy ray include high-energy rays such as electromagnetic wave energy having a wavelength of 2,000 angstroms or more and 7,000 angstroms or less, electron beams, X-rays, and radiation, which are obtained from ultra-high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, mercury vapor arc lamps, xenon arc lamps, carbon arc lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light-emitting diodes, and CRT light sources, etc. The light source used in this step is preferably an ultra-high pressure mercury lamp, a mercury vapor arc lamp, a carbon arc lamp, a xenon arc lamp, a light-emitting diode, or the like that emits light with a wavelength of 300 or more and 450 or less, since this makes it easier to control the curing reaction of the composition.

[0183] The amount of irradiation with the active energy rays is not particularly limited and can be appropriately determined depending on the composition of the composition. From the viewpoint of preventing deterioration of the composition, the amount of irradiation is set to 100 mJ / cm at 365 nm. 2 More than 2,000mJ / cm 2 It is preferable that:

[0184] In this step, the curing method may be any method that includes a method of irradiating the coating film with active energy rays, and may also be used in combination with a method of heating the coating film.

[0185] Examples of the method for heating the coating film include a method using a hot plate or other hot plate, an atmospheric oven, an inert gas oven, a vacuum oven, and a hot air circulation oven. When the coating film is heated, the heating temperature is not particularly limited, but from the viewpoint of easy control of the curing reaction of the composition, it is preferably 50°C or higher and 200°C or lower, and more preferably 60°C or higher and 150°C or lower. The time for heating the coating film is not particularly limited, but from the viewpoint of improving productivity, it is preferably from 10 seconds to 60 minutes, more preferably from 20 seconds to 10 minutes, and even more preferably from 30 seconds to 3 minutes.

[0186] On the other hand, when a thermal cationic polymerization initiator is used as the cationic polymerization initiator, the curing temperature is preferably 100° C. or higher and 250° C. or lower, and more preferably 120° C. or higher and 175° C. or lower.

[0187] (b) Other processes The method of the present disclosure may include other steps, as required. The other steps include, for example, a coating step of coating the composition onto a substrate prior to the above-mentioned "(a) curing step". In the coating step, the composition can be applied to a substrate by any known method, such as using a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing methods, and dipping.

[0188] The substrate can be appropriately selected depending on the application of the cured product, and is not particularly limited, and any substrate that is commonly used can be used. Examples of the substrate include metal materials, polymeric materials, wood materials, paper materials, and inorganic materials.

[0189] Examples of the metal material include iron, copper, aluminum, titanium, tinplate, stainless steel, mild steel, plated steel, coated steel sheet, and galvanized steel sheet.

[0190] Examples of the polymeric material include cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, and nitrocellulose; polyamide (nylon); polyurethane; epoxy resin; polycarbonate; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; styrene-based resins such as polystyrene and ABS resin; olefin-based resins such as polyethylene, polypropylene, and polymethylpentene; vinyl-based resins such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; acrylic resins such as polymethyl methacrylate and polyacrylate; polycarbonate; engineering plastics such as amorphous polyarylate, polysulfone, polyethersulfone, polyphenylene sulfide, polyether ether ketone, polyimide, polyetherimide, and fluororesin; and cyclic polymers such as norbornene resin and cycloolefin polymer (COP).

[0191] Examples of the wood material include wood, plywood, particle board, and MDF.

[0192] Examples of the paper material include plain paper, reinforced paper, resin-impregnated paper, and cardboard.

[0193] Examples of the inorganic material include gypsum board and calcium silicate board.

[0194] D. Composition used to impart antiviral properties to the cured product The present invention can also provide a composition containing a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt and a curable component, which is used to impart antiviral properties to a cured product. The above items A to C are used for this composition without any particular limitations. Specifically, this composition can be used as a composition for forming an antiviral coating or a composition for forming an antiviral resin molding.

[0195] E.Other The invention of this disclosure includes the following inventions [1] to [7]. [1] A method for imparting antiviral properties to a cured product, comprising imparting antiviral properties to the cured product by using a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt. [2] The cationic polymerization initiator has, as an anion, (CF3SO2)3C - , (C6F5)4B - The method according to claim 1, comprising: [3] The method according to [1] or [2], wherein the cured product is obtained by curing a composition containing the cationic polymerization initiator and a curable component. [4] The method according to [3], wherein the curable component comprises an epoxy compound. [5] The method according to [3], wherein the content of the cationic polymerization initiator is 0.1 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the solid content of the composition. [6] A composition used to impart antiviral properties to a cured product, comprising a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt and a curable component. [7] The composition according to [6] for use in a human body contact member.

[0196] The present disclosure is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any embodiment that has substantially the same configuration as the technical idea described in the claims of the present disclosure and exhibits similar effects is included in the technical scope of the present disclosure. EXAMPLES

[0197] [Examples 1 to 3] The components were mixed according to the formulation shown in Table 1 below to obtain a composition. The amounts in the tables are in parts by mass of each component. The components used are shown below.

[0198] Cationic Polymerization Initiator The compounds represented by A1 to A3 below were used as the monosulfonium salt or iodonium salt, which is a photocationic polymerization initiator, and the compound represented by a1 below was used as a comparative compound for evaluation.

[0199] [ka]

[0200] A1: (Onium salt-based photocationic polymerization initiator, iodonium salt, anion is B(C6F5)4 - ) A2: (Onium salt-based photocationic polymerization initiator, sulfonium salt, anion is (CF3SO2)3C - (a mixture of disulfonium salt and monosulfonium salt in a mass ratio of 50:50) A3: (Onium salt-based photocationic polymerization initiator, sulfonium salt, anion is B(C6F5)4 - ) a1: (onium salt-based photocationic polymerization initiator, sulfonium salt, anion is PF6 - )

[0201] (2) Curable component As the curable components, the following B1 to B4 were used for evaluation.

[0202] [ka]

[0203] B1: Celloxide 2021P (manufactured by Daicel Corporation, alicyclic epoxy compound, compound represented by the above general formula (2-5)) B2: Diglycidyl ether of bisphenol A, aromatic epoxy compounds, compounds represented by the above general formula (2-7) B3: 4-tert-butyl glycidyl ether, aromatic epoxy compounds, and compounds represented by the above general formula (2-8) B4: Epolite M-1230 (manufactured by Kyoritsu Chemical Co., Ltd.), acyclic aliphatic epoxy compounds, and compounds represented by the above general formula (2-16)

[0204] <Antiviral> In accordance with the international industrial standard ISO 21702, an antiviral test was conducted against human coronaviruses to evaluate the inactivation rate (%). The antiviral test was conducted according to the following procedure. Each composition was coated on a PET film (Toyobo A4360) and exposed to a 365 nm LED light source (1,000 mW / cm 2 ) at 500mJ / cm 2 A cured product was obtained by exposure to light (coating film thickness: 5 μm). The obtained cured product was cut into a size of 5 cm wide x 5 cm long to prepare a measurement sample. A PET film was cut into a size of 5 cm width x 5 cm length to prepare an unprocessed test piece. A specific amount of human coronavirus virus fluid was dropped onto the obtained measurement samples and untreated test pieces, which were then covered with a 4 cm square film and left to stand in an environment of 25°C for 24 hours. After standing, the viruses on the measurement sample and the untreated test piece were washed and collected, and the virus infectivity was measured. The inactivation rate (%) was calculated according to the following formula. R = {1-(At / Ut)} x 100 R: Inactivation rate (%) Ut: Virus infectivity of untreated test specimen after 24 hours (PFU / cm 2 ) At: Virus infectivity of test specimen after 24 hours (PFU / cm 2 )

[0205] The antiviral test was performed twice for each measurement sample, and the inactivation rate (%) was calculated using the average viral infectivity value. The results are shown in Table 1 below. An inactivation rate of 95% or higher is considered to be an antiviral effect.

[0206] [Table 1]

[0207] From Comparative Example 1, when the cationic polymerization initiator was neither a monosulfonium salt nor an iodonium salt, the inactivation rate (%) was insufficient. In contrast, from Examples 1 to 3, it was confirmed that the cured products of all the compositions of the examples had an inactivation rate (%) of 95% or more and exhibited excellent antiviral properties. It was also confirmed that the cured products of Examples 1 to 3 did not suffer from problems such as bleeding.

[0208] In addition, when an antiviral test (ISO21702) was performed on a sample prepared by dissolving the cationic polymerization initiator A1 and PMMA (Sumitomo Chemical Co., Ltd.'s "Sumipex LG") in a toluene solution, applying the solution to a PET film (Toyobo Cosmoshine A4360, Toray DuPont Co., Ltd.), and drying at 80°C for 1 minute, no antiviral properties were confirmed. Therefore, although the cationic polymerization initiator itself cannot exhibit antiviral properties, the method disclosed herein can obtain a cured product having excellent antiviral properties by curing the composition by irradiating it with active energy rays.

Claims

1. A method for imparting antiviral property to a cured product, comprising imparting antiviral property to the cured product by using a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt.

2. The cationic polymerization initiator has, as an anion, (CF ３ SO ２ ) ３ C － Or (C ６ F ５ ) ４ B － 2. The method of claim 1, comprising:

3. The method according to claim 1 , wherein the cured product is obtained by curing a composition containing the cationic polymerization initiator and a curable component.

4. The method of claim 3 , wherein the hardenable component comprises an epoxy compound.

5. The method according to claim 3, wherein the content of the cationic polymerization initiator is 0.1 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the solid content of the composition.

6. A composition used for imparting antiviral properties to a cured product, the composition comprising a cationic polymerization initiator containing a monosulfonium salt or an iodonium salt, and a curable component.

7. The composition according to claim 6 for use in a body contact member.

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