Antiviral agents and their uses

Abstract

This invention provides an antiviral agent with excellent heat resistance and its applications. [Solution] An antiviral agent comprising a fluorene compound having a fluorene skeleton as an active ingredient. The fluorene compound may include at least one selected from compounds having a 9,9-bisarylfluorene skeleton and compounds having a 9,9-bisalkylfluorene skeleton. The fluorene compound may include a compound of the following formula. TIFF2026090976000013.tif62161

Description

[Technical Field]

[0001] This disclosure relates to an antiviral agent containing a fluorene compound as an active ingredient and its uses [for example, an antiviral coating agent containing the antiviral agent and its coating layer, an antiviral polymer composition and its molded article; and a method for imparting antiviral properties]. [Background technology]

[0002] Quaternary ammonium salts often exhibit antibacterial and antiviral properties and are commonly used as antimicrobial and antiviral agents. Due to their high solvent solubility, quaternary ammonium salts can impart antibacterial and antiviral properties when applied as a coating liquid to substrates (such as glass and plastic). However, quaternary ammonium salts are known to undergo thermal decomposition at high temperatures due to Hoffmann elimination, which breaks the nitrogen atom bond. This makes them unsuitable not only for substrates requiring heat resistance but also for applications such as mixing (e.g., melt mixing) into polymer components at high temperatures, thus creating a need for improved heat resistance.

[0003] U.S. Patent No. 4,672,118 (Patent Document 1) discloses that certain pyridinium compounds, in which the N-position is substituted with an aromatic substituent to which a hydrophobic group is attached, exhibit high heat resistance. However, depending on the application or target, the heat resistance may not be sufficient.

[0004] Unlike organic compounds such as quaternary ammonium salts, antiviral agents containing silver (or silver ions) have been developed as inorganic compounds that exhibit high heat resistance. However, because the activity of silver (or silver ions) is too high, it can react with articles or substrates, causing discoloration or staining, and when applied to or mixed with transparent materials (transparent substrates or polymer components), it is prone to causing whitening or clouding of the transparent material. Therefore, its applications are greatly limited by its impact on appearance.

[0005] On the other hand, in order to improve the heat resistance or stability, which are weaknesses of organic compounds, and to expand their applications, it is known that they are combined with inorganic compounds to form inorganic-organic hybrid types. Takehisa Eiji, "Inorganic-Organic Hybrid Antibacterial and Antifungal Agents," Inorganic Materials, The Japan Society for Inorganic Materials, 1999, Vol. 6, No. 283, pp. 525-531 (Non-Patent Literature 1) describes that by intercalating organic guest compounds such as benzalkonium between layers of a layered, sparingly soluble phosphate host compound, discoloration can be prevented and heat resistance can be improved. However, even with such inorganic-organic hybrid types, heat resistance may not be sufficient depending on the application or target. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] U.S. Patent No. 4672118 [Non-patent literature]

[0007] [Non-Patent Document 1] Eiji Takehisa, "Inorganic-Organic Hybrid Antibacterial and Antifungal Agents," Inorganic Materials, The Japan Society for Inorganic Materials, 1999, Vol. 6, No. 283, pp. 525-531. [Overview of the project] [Problems that the invention aims to solve]

[0008] Therefore, the object of this disclosure is to provide an antiviral agent with excellent heat resistance and its applications. [Means for solving the problem]

[0009] As a result of diligent research to achieve the above objectives, the present inventors discovered that fluorene compounds exhibit not only high heat resistance but also excellent antiviral properties, thus completing the present invention (or this disclosure). That is, this disclosure may include the following embodiments, etc.

[0010] Appearance [1]: An antiviral agent containing a fluorene compound having a fluorene skeleton as an active ingredient.

[0011] Appearance [2] The antiviral agent according to embodiment [1], wherein the fluorene compound comprises at least one selected from a compound having a 9,9-bisarylfluorene skeleton, a compound having a 9,9-bisalkylfluorene skeleton, a compound having a 9-fluorenone skeleton, and a compound having a 9H-fluorene skeleton.

[0012] Appearance [3]: The antiviral agent according to embodiment [1] or [2], wherein the fluorene compound comprises at least one selected from compounds having a 9,9-bisarylfluorene skeleton and compounds having a 9,9-bisalkylfluorene skeleton.

[0013] Appearance [4]: The antiviral agent according to any one of embodiments [1] to [3], wherein the fluorene compound comprises at least one selected from a compound having a 9,9-bisarylfluorene skeleton represented by the following formula (1) and a compound having a 9,9-bisalkylfluorene skeleton represented by the following formula (2).

[0014] [ka]

[0015] (In the formula, R 1 represents a substituent, and m1 represents an integer from 0 to 8. Z 1a and Z 1b These independently show an arene ring, X 1a and X 1b p1a and p1b independently represent a heteroatom-containing functional group, and p1a and p1b independently represent integers greater than or equal to 1. R 3a and R 3brepresents a substituent independently, and m3a and m3b represent integers of 0 or more independently.)

[0016] [Chemical formula]

[0017] (In the formula, R 4 represents a substituent, m4 represents an integer from 0 to 8, A 2a and A 2b each independently represent an alkylene group which may have a substituent, X 2a and X 2b each independently represent a heteroatom-containing functional group.)

[0018] Aspect [5]: In the above formula (1), R 1 represents a hydrocarbon group, m1 represents an integer from 0 to 4, Z 1a and Z 1b each independently represent a C 6-18 arene ring, X 1a and X 1b each independently represent the group [-O-(A<00000thirteen>O) n1 -H] (wherein A 1 represents an alkylene group, n1 represents an integer of 0 or more.), the group [-C(=O)-R 2 ) [wherein R 2 represents a hydroxyl group, the group [-OR h (wherein R h represents a hydrocarbon group.), a halogen atom, an amino group or a substituted amino group.], an amino group or a substituted amino group, p1a and p1b each independently represent an integer from 1 to 2, R 3a and R 3b each independently represent a hydrocarbon group, m3a and m3b each independently represent an integer from 0 to 4; In the above formula (2), R 4 represents a hydrocarbon group, m4 represents an integer from 0 to 4, A 2a and A 2b This independently represents an alkylene group which may have a hydrocarbon group, X 2a and X 2b The base [-O-(A 3 O) n3 -H](where A 3 represents an alkylene group, and n3 represents an integer greater than or equal to 0. ), group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h ) represents a hydrocarbon group. ), a halogen atom, an amino group or a substituted amino group. ], an amino group or a substituted amino group, the antiviral agent according to embodiment [4].

[0019] Appearance [6]: The antiviral agent according to any one of embodiments [1] to [5], wherein the fluorene compound includes a compound having a symmetrical chemical structure with respect to the 9-position of the fluorene skeleton.

[0020] Appearance [7]: The antiviral agent according to any one of embodiments [1] to [6], wherein the molecular weight of the fluorene compound is 3000 or less.

[0021] Appearance [8]: The antiviral agent according to any one of embodiments [1] to [7], wherein the 5% weight loss temperature of the fluorene compound is 250°C or higher.

[0022] Appearance [9]: An antiviral agent according to any one of embodiments [1] to [8], which is an antiviral agent against enveloped viruses or non-enveloped viruses.

[0023] Appearance

[10] : An antiviral coating agent comprising the antiviral agent described in any of embodiments [1] to [9].

[0024] Appearance

[11] : A method for forming an antiviral coating layer containing the active ingredient on the surface of an article or substrate by coating it with the antiviral coating agent described in embodiment

[10] (a method for producing an antiviral coating layer).

[0025] Appearance

[12] : The antiviral coating layer according to embodiment

[11] .

[0026] Appearance

[13] : An antiviral polymer composition comprising an antiviral agent according to any one of embodiments [1] to [9] and a polymer component.

[0027] Appearance

[14] : An antiviral molded article comprising the antiviral polymer composition described in embodiment

[13] .

[0028] Appearance

[15] : A method for imparting antiviral properties to a polymer component by mixing an antiviral agent described in any of embodiments [1] to [9] with the polymer component.

[0029] Furthermore, this disclosure may achieve the following secondary objectives (or solve the following secondary problems):

[0030] In other words, another object of this disclosure is to provide an antiviral agent that exhibits excellent antiviral properties (antiviral activity) and a broad antiviral spectrum, and its applications.

[0031] Another object of this disclosure is to provide antiviral agents that exhibit high antiviral activity even at low concentrations, and applications thereof.

[0032] Another object of this disclosure is to provide antiviral agents and applications that can suppress coloring or discoloration of the subject matter (such as articles, substrates, or polymer components).

[0033] Another object of this disclosure is to provide an antiviral agent with excellent compatibility with polymer components and its applications.

[0034] In this specification and in the claims, the number of carbon atoms in a substituent is defined as C1, C6, C 10 These are sometimes used to indicate this. For example, an alkyl group with 1 carbon atom is called a "C1 alkyl group," and an aryl group with 6 to 10 carbon atoms is called a "C1 alkyl group." 6-10 It is indicated as "aryl group," etc.

[0035] In this specification and in the claims, “independently” means that the two components are independent components, Z 1a and Z 1b In the case of Z 1a and Z 1b This means that the two arene rings do not need to be the same, and they can be different from each other.

[0036] In this specification and in the claims, numerical ranges indicated as "X~Y" etc. may include the numerical values ​​X and Y. [Effects of the Invention]

[0037] This disclosure provides an antiviral agent with excellent heat resistance and its applications. [Modes for carrying out the invention]

[0038] The antiviral agent (virus removal agent) disclosed herein contains a fluorene compound having a fluorene skeleton as an active ingredient, and therefore exhibits antiviral properties (antiviral activity) despite being an organic compound. Therefore, it can be easily and efficiently manufactured, resulting in excellent productivity. Furthermore, the antiviral agent disclosed herein exhibits excellent antiviral properties and can also show a broad antiviral spectrum. Moreover, it can exhibit high antiviral activity even at low concentrations. In addition, it readily suppresses discoloration or staining of the target object (articles, substrates, or polymer components, etc.). It also tends to have excellent compatibility with polymer components.

[0039] [Fluorene compounds] The active ingredient, a fluorene compound, only needs to have a fluorene skeleton (fluorene ring) in its chemical structure, and may have a symmetric or asymmetric chemical structure with respect to the 9-position of the fluorene skeleton, preferably a symmetric chemical structure. A chemical structure symmetric with respect to the 9-position of the fluorene skeleton means a chemical structure that can be drawn symmetrically on paper, that is, a chemical structure in which the types of groups (hydrogen atoms or substituents) attached to the 9,9-position of the fluorene skeleton are the same, the types of groups attached to the 1,8-position are the same, the types of groups attached to the 2,7-position are the same, the types of groups attached to the 3,6-position are the same, and the types of groups attached to the 4,5-position are the same.

[0040] Furthermore, because the fluorene compound has excellent heat resistance and antiviral properties, and can be easily or efficiently produced by conventional methods, it is preferable that it contains at least one selected from compounds having a 9,9-bisarylfluorene skeleton (F1) [also called fluorene compound (F1)], compounds having a 9,9-bisalkylfluorene skeleton (F2) [also called fluorene compound (F2)], compounds having a 9-fluorenone skeleton (F3) [also called fluorene compound (F3)], and compounds having a 9H-fluorene skeleton (fluorene skeleton with the 9-position unsubstituted) (F4) [also called fluorene compound (F4)]. The fluorene compound may be used alone or in combination of two or more types.

[0041] (F1) Compounds having a 9,9-bisarylfluorene skeleton The fluorene compound (F1) can be any compound that has a 9,9-bisarylfluorene skeleton in its chemical structure, such as the compound represented by the following formula (1).

[0042] [ka]

[0043] (In the formula, R 1 represents a substituent, and m1 represents an integer from 0 to 8. Z 1a and Z1b These independently show an arene ring, X 1a and X 1b p1a and p1b independently represent a heteroatom-containing functional group, and p1a and p1b independently represent integers greater than or equal to 1. R 3a and R 3b (where m3a and m3b independently represent substituents, and m3a and m3b independently represent non-negative integers.)

[0044] In the above equation (1), R 1 Examples of substituents represented by [-OR] include halogen atoms, hydrocarbon groups, and groups. h ](wherein, R h (represents a hydrocarbon group), group [-SR h ](wherein, R h Examples include hydrocarbon groups, acyl groups, nitro groups, cyano groups, and substituted amino groups (mono or disubstituted amino groups).

[0045] In this specification and in the claims, R h The hydrocarbon groups represented by each symbol represent independent hydrocarbon groups, which may be identical or different from one another.

[0046] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0047] R 1 hydrocarbon group as (and R h The hydrocarbon group (as R) may be saturated or unsaturated hydrocarbon groups, aliphatic (including alicyclic) or aromatic hydrocarbon groups, and may be linear (linear or branched) or cyclic, or a combination of linear and cyclic structures. h The number of carbon atoms in the compound is not particularly limited, but may be as low as 20, for example, and preferably in the following increments: 1-16, 1-12, 1-10, 1-8, and 1-6.

[0048] Typical hydrocarbon groups include alkyl groups, cycloalkyl groups, aryl groups, and aralkyl groups.

[0049] Examples of alkyl groups (linear or branched alkyl groups) include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl groups. 1-10 Examples include alkyl groups, preferably C 1-6 Alkyl alkyl groups, more preferably C 1-4 It is an alkyl group.

[0050] Examples of cycloalkyl groups include cyclopentyl groups, cyclohexyl groups, and other C groups. 5-10 Examples include cycloalkyl groups.

[0051] Examples of aryl groups include phenyl groups, alkylphenyl groups, biphenylyl groups, naphthyl groups, etc. 6-12 Examples include aryl groups. Alkylphenyl groups include mono- or tri-C groups such as methylphenyl (or tolyl) and dimethylphenyl (or xylyl) groups. 1-4 Examples include alkylphenyl groups.

[0052] Examples of aralkyl groups include benzyl groups, phenethyl groups, and other C groups. 6-10 Aryl-C 1-4 Examples include alkyl groups.

[0053] The group [-OR h ] and base [-SR h In ], R h As a hydrocarbon group represented by R 1 Examples of hydrocarbon groups include those similar to the hydrocarbon groups exemplified above, including preferred embodiments, such as alkyl groups, cycloalkyl groups, aryl groups, and aralkyl groups. The aforementioned group [-OR h ] and base [-SR h For example, R h (R 1Groups corresponding to hydrocarbon groups as [-OR h include, for example, alkoxy groups, cycloalkyloxy groups, aryloxy groups, aralkyloxy groups, etc.; representative groups [-SR h include, for example, alkylthio groups, cycloalkylthio groups, arylthio groups, aralkylthio groups, etc.

[0054] Examples of alkoxy groups (linear or branched alkoxy groups) include C 1-10 alkoxy groups such as methoxy group, ethoxy group, propoxy group, n-butoxy group, isobutoxy group, t-butoxy group, etc. Examples of cycloalkyloxy groups include C 5-10 cycloalkyloxy groups such as cyclohexyloxy group. Examples of aryloxy groups include C 6-10 aryloxy groups such as phenoxy group. Examples of aralkyloxy groups include C 6-10 aryl-C 1-4 alkyloxy groups such as benzyloxy group.

[0055] Examples of alkylthio groups include C 1-10 alkylthio groups such as methylthio group, ethylthio group, propylthio group, n-butylthio group, t-butylthio group, etc. Examples of cycloalkylthio groups include C 5-10 cycloalkylthio groups such as cyclohexylthio group. Examples of arylthio groups include C 6-10 arylthio groups such as thiophenoxy group. Examples of aralkylthio groups include C 6-10 aryl-C 1-4 alkylthio groups such as benzylthio group.

[0056] Examples of acyl groups include C 1-12 acyl groups etc., for example, C 1-6 alkyl-carbonyl groups such as acetyl group etc.

[0057] Examples of the mono- or di-substituted amino group include a mono- or dialkylamino group, a mono- or diacylamino group, etc. Examples of the mono- or dialkylamino group include a mono- or diC 1-4 alkylamino group such as a mono- or dimethylamino group. Examples of the mono- or diacylamino group include a mono- or diC 1-7 acylamino group such as a mono- or diacetylamino group.

[0058] Typical R 1 includes a halogen atom, a hydrocarbon group, a group [-OR h (such as an alkoxy group), an acyl group, etc., and preferably a hydrocarbon group such as an alkyl group or an aryl group. Examples of the alkyl group (linear or branched alkyl group) include a C 1-6 alkyl group such as a methyl group, an ethyl group, a t-butyl group, etc., and a C 1-4 alkyl group such as a methyl group is preferred. Examples of the aryl group include a C 6-10 aryl group such as a phenyl group.

[0059] R 1 The substitution number m1 of is an integer from 0 to 8, for example, an integer of about 0 to 6, preferably, stepwise, an integer of 0 to 4, an integer of 0 to 2 (such as 0 or 1, etc.), more preferably 0 or 2, and particularly 0. When m1 is 2 or more, the types of two or more R 1 may be the same as or different from each other. Also, among the two benzene rings forming the fluorene skeleton, when R 1 is substituted on both benzene rings, the type of R 1 on one benzene ring and the type of R 1 on the other benzene ring may be different from each other or preferably the same. Also, the substitution position of R 1 is not particularly limited as long as it is at the 1- to 8-positions of the fluorene skeleton, and may be, for example, the 2-position, the 3-position, the 2,7-positions, etc.

[0060] Z 1a or Z 1bExamples of arene rings (aromatic hydrocarbon rings) represented by this formula include monocyclic arene rings such as benzene rings, and polycyclic arene rings. Examples of polycyclic arene rings include fused polycyclic arene rings (fused polycyclic aromatic hydrocarbon rings) and ring-aggregated arene rings (ring-aggregated aromatic hydrocarbon rings).

[0061] Examples of fused polycyclic arene rings include fused bicyclic arene rings, fused tricyclic arene rings, and other fused dicyclic to tetracyclic arene rings. Examples of fused bicyclic arene rings include naphthalene rings and indene rings. 9-16 Examples include arene rings. Examples of fused tricyclic arene rings include anthracene rings and phenanthrene rings. 14-20 Examples include arene rings. Preferred fused polycyclic arene rings include naphthalene rings and other fused polycyclic C rings. 10-14 It is an arene ring.

[0062] Examples of ring-assembled arene rings include bialene rings such as biphenyl rings, phenylnaphthalene rings, and binaphthyl rings; and telarene rings such as terphenyl rings (m-terphenyl rings, etc.). Preferred ring-assembled arene rings are bi or telarene rings (especially telarene rings), and more preferably biphenyl rings, m-terphenyl rings, etc. 12-18 It is a bi or telarene ring, and in particular a biphenyl ring.

[0063] In this specification and in the claims, "ring-assembled arene ring" means a ring in which two or more ring systems (arene ring systems) are directly connected by single or double bonds, and the number of bonds directly connecting the rings is one less than the number of ring systems. For example, as mentioned above, phenylnaphthalene rings and binaphthyl rings are classified as ring-assembled arene rings even though they have a fused polycyclic arene ring skeleton, and are clearly distinguished from "fused polycyclic arene rings" such as naphthalene rings (aring-assembled arene rings).

[0064] Z 1a ,Z 1b The arene ring represented by is preferably C6-18 An arene ring is an example, and more preferably C 6-14 C such as an arene ring, more preferably a benzene ring, naphthalene ring, or biphenyl ring. 6-12 Arene rings (e.g., benzene rings, naphthalene rings, etc.) 6-10 C11 (arene ring), and among them, naphthalene rings, biphenyl rings, etc. are considered to have superior antiviral properties even at low concentrations. 10-12 An arene ring is preferred, and a biphenyl ring is particularly preferred. Also, Z 1a and Z 1b The types may be the same or different from each other, but it is preferable that they be the same.

[0065] Note that Z is bonded at the 9-position of the fluorene ring. 1a and Z 1b The substitution position is not particularly limited; for example, Z 1a ,Z 1b If it is a benzene ring, it can be in any position, Z 1a ,Z 1b If it is a naphthalene ring, it is at either the 1-position (1-naphthyl) or the 2-position (2-naphthyl), preferably at the 2-position, Z 1a ,Z 1b If it is a biphenyl ring, it is at one of the 2-, 3-, or 4-positions, preferably at the 3-position.

[0066] X 1a or X 1b The heteroatom-containing functional group represented by may be any group containing at least one heteroatom. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms, with nitrogen atoms and oxygen atoms being preferred, and oxygen atoms being more preferably preferred. The number of heteroatoms in the heteroatom-containing functional group is, for example, an integer from 1 to 20, preferably in stages from 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, and 1 to 3, and more preferably 1 or 2.

[0067] X 1a ,X 1bExamples of heteroatom-containing functional groups represented by the group [-O-(A 1 O) n1 -H](wherein, A 1 represents an alkylene group, and n1 represents a non-negative integer. ), group [-C(=O)-R 2 ][wherein, R 2 is a hydroxyl group, group [-OR h ](wherein, R h represents a hydrocarbon group. ), a halogen atom, an amino group, or a substituted amino group. Examples include ], an amino group, a substituted amino group, etc.

[0068] Base [-O-(A 1 O) n1 -H] represents a hydroxyl group or a hydroxy(mono or poly)alkoxy group. 1 Examples of alkylene groups (linear or branched alkylene groups) represented by this symbol include ethylene, propylene (1,2-propanediyl), trimethylene, 1,2-butanediyl, and tetramethylene groups. 2-6 Examples include alkylene groups, preferably C 2-4 C such as an alkylene group, more preferably an ethylene group, a propylene group, etc. 2-3 Alkylene groups, particularly ethylene groups, are preferred.

[0069] Alkylene oxy group [-(A 1 The number of repetitions (number of added moles) n1 of the group [-O-(A)-] is 0 or greater, and can be selected from a range of approximately 0 to 15, preferably in the following increments: 0 to 10, 0 to 8, 0 to 6, 0 to 4, 0 to 2, 0 to 1, where the number of repetitions n1 is 0 (i.e., the group [-O-(A)-] 1 O) n1 If the group [-O-(A] is a phenolic hydroxyl group, it appears that the antiviral activity, especially against enveloped viruses such as influenza viruses, is more easily improved. Also, if the number of repetitions n1 is 1 or more, (i.e., the group [-O-(A] is a phenolic hydroxyl group) 1 O) n1If the -H group has an alcoholic hydroxyl group, it exhibits good compatibility with polymer components and is less prone to staining or discoloration. For example, it can be selected from a range of about 1 to 15, preferably in the following increments: 1 to 10, 1 to 8, 1 to 6, 1 to 4, 1 to 3, 1 to 2, with 1 being particularly preferred.

[0070] In this specification and in the claims, the "number of repetitions (number of added moles)" may be an integer, an average value (arithmetic mean, arithmetic mean), or an average number of added moles, and in either case, the preferred embodiment may be the same as the preferred range described above. When n1 is in a moderate range that is not too large, it tends to be easier to suppress the decrease in heat resistance and refractive index. Also, when n1 is 2 or more, 2 or more alkylene oxy groups [-(A 1 The types of O)-] may be different from each other, but it is preferable that they be the same.

[0071] Group [-C(=O)-R 2 ] is a carboxyl group (R 2 A group derived from a hydroxyl group or a carboxyl group (for example, R 2 is based on [-OR h ] is a carboxylic acid ester group, R 2 R is a halogen atom in the carboxylic acid halide group. 2 This corresponds to an amino group or a carboxyl amide group which is a substituted amino group. In the case of a carboxyl group, it may also be in the form of an acid anhydride or the like.

[0072] R 2 is based on [-OR h If ] then R h Examples of hydrocarbon groups represented by the above R 1 Examples include the hydrocarbon groups described as such, and similar groups including preferred embodiments. Also, R 2 As a base [-OR h ] is, for example, the R 1 The base described as [-OR h Examples include similar groups, including preferred embodiments. Representative group [-C(=O)-ORh Examples of alkoxycarbonyl groups include alkoxycarbonyl groups, cycloalkoxycarbonyl groups, aryloxycarbonyl groups, and aralkyloxycarbonyl groups, with alkoxycarbonyl groups being preferred. Examples of alkoxycarbonyl groups (linear or branched alkoxycarbonyl groups) include methoxycarbonyl groups, ethoxycarbonyl groups, propoxycarbonyl groups, n-butoxycarbonyl groups, isobutoxycarbonyl groups, t-butoxycarbonyl groups, etc. 1-10 Alkoxy-carbonyl group, preferably C 1-6 C such as an alkoxy-carbonyl group, more preferably a methoxycarbonyl group. 1-4 It is an alkoxy-carbonyl group.

[0073] R 2 When the group is a halogen atom, examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. A typical group is [-C(=O)-R 2 ](wherein, R 2 This indicates a halogen atom. Examples include halocarbonyl groups such as chlorocarbonyl groups.

[0074] R 2 If is an amino group or a substituted amino group (mono or disubstituted amino group), the substituted amino group may be, for example, the R 1 Examples include the substituted amino group described above, and similar groups, including preferred embodiments. A representative group is [-C(=O)-R 2 ](wherein, R 2 This indicates an amino group or a substituted amino group. Examples of such groups include carbamoyl groups, mono- or dialkylcarbamoyl groups, and mono- or diacylcarbamoyl groups. Examples of mono- or dialkylcarbamoyl groups include mono- or didimethylcarbamoyl groups. 1-4 Examples include alkyl-carbamoyl groups. Mono- or diacylcarbamoyl groups include mono- or diacetylcarbamoyl groups, for example. 1-7 An example is the acyl-carbamoyl group.

[0075] X 1a ,X 1b When the heteroatom-containing functional group represented by is a substituted amino group (mono or disubstituted amino group), the substituted amino group is, for example, the R 1 Examples include the substituted amino groups described above, and similar groups, including preferred embodiments.

[0076] X 1a ,X 1b A preferred heteroatom-containing functional group represented by the group [-O-(A 1 O) n1 -H](wherein, A 1 represents an alkylene group, and n1 represents a non-negative integer. ), group [-C(=O)-R 2 ][wherein, R 2 is a hydroxyl group, group [-OR h ](wherein, R h represents a hydrocarbon group. ), an amino group or a substituted amino group. ], an amino group, a substituted amino group; more preferably a group [-O-(A 1 O) n1 -H](wherein, A 1 is C 2-6 This indicates an alkylene group, where n1 is an integer from 0 to 10. ) , group [-C(=O)-R 2 ][wherein, R 2 is the base [-OR h ](wherein, R h [-O-(A] represents a hydrocarbon group such as an alkyl group. ], an amino group, or a substituted amino group; more preferably, the group [-O-(A] is preferred due to its excellent antiviral properties. 1 O) n1 -H](wherein, A 1 is C 2-4 It represents an alkylene group, where n1 is an integer from 0 to 6. ) ), an amino group, a substituted amino group; among these, the group [-O-(A 1 O) n1 -H](wherein, A 1 is C 2-3 It represents an alkylene group, where n1 is an integer from 0 to 3. ), or an amino group; particularly preferably the group [-O-(A 1 O) n1 -H](wherein, A 1represents a C alkylene group such as an ethylene group, n1 represents an integer of 0 to 2, preferably n1 represents 0.) Also, in terms of having good compatibility with the polymer component and being easy to suppress coloring or discoloration, the group [-O-(A 2-3 O) 1 O) n1 -H] (where A 1 represents a C alkylene group such as an ethylene group, n1 represents an integer of 1 or more, preferably n1 represents an integer of 1 to 3, more preferably 1 or 2, particularly 1.) is preferred. The types of X 2-3 and X 1a may be different from each other, but are preferably the same. 1b The substitution numbers p1a and p1b of X

[0077] and X 1a and X 1b each represent an integer of 1 or more. Depending on the types of Z 1a and Z 1b etc., for example, they are integers of 1 to 10, preferably, in stages, integers of 1 to 6, integers of 1 to 4, integers of 1 to 3, more preferably 1 or 2, particularly 1. p1a and p1b may be different from each other, but are preferably the same. Also, when p1a is 2 or more, the types of 2 or more X 1a may be the same as or different from each other; when p1b is 2 or more, the types of 2 or more X 1b may be the same as or different from each other.

[0078] The substitution positions of the heteroatom-containing functional group represented by X 1a , X 1b with respect to Z 1a , Z 1b are not particularly limited, and they may be substituted at appropriate positions of Z 1a , Z 1b respectively. The substitution positions of X 1a , X 1b with respect to Z 1a , Z 1b are the substitution positions with respect to Z 1a , Z 1bIf is a benzene ring, the phenyl group bonded to the 9-position of the fluorene ring is preferably at the 2-, 3-, or 4-position, and most preferably at the 3- or 4-position, and especially at the 4-position. Also, Z 1a ,Z 1b When is a naphthalene ring, substitution often occurs at one of the 5-8 position positions of the naphthyl group bonded to the 9-position of the fluorene ring. For example, the 1- or 2-position of the naphthalene ring is substituted for the 9-position of the fluorene ring (substitution in the relationship of 1-naphthyl or 2-naphthyl), and it is preferable that this substitution occurs in the relationship of 1,5-position, 2,6-position, and especially the relationship of 2,6-position. Also, Z 1a ,Z 1b If X is a ring set of allene rings, 1a ,X 1b The substitution position is not particularly limited; for example, it may be substituted on the arene ring bonded to the 9-position of fluorene or on an arene ring adjacent to this arene ring. For example, Z 1a ,Z 1b is a biphenyl ring (or Z 1a ,Z 1b The benzene ring is 1, m3a and m3b are 1, R 3a ,R 3b If ( is a phenyl group), it is preferable that the 3-position of the biphenyl ring is bonded to the 9-position of fluorene, and the 6-position of the biphenyl ring is X 1a ,X 1b It is preferable to combine them.

[0079] R 3a or R 3b Examples of substituents represented by R 1 Examples include groups similar to the substituents described above. 3a ,R 3b Typical substituents represented are halogen atoms, hydrocarbon groups, and groups [-OR h Examples include C11 (alkoxy group, etc.) and acyl group, preferably hydrocarbon groups such as alkyl groups and aryl groups. Examples of alkyl groups (linear or branched alkyl groups) include C11, methyl group, ethyl group, t-butyl group, etc. 1-6 Examples include alkyl groups, such as methyl groups and C 1-4An alkyl group is preferred. Examples of the aryl group include a C 6-10 aryl group and the like. R 3a and R 3b may be different from each other, and it is preferred that they are the same. Also, when R 3a , R 3b is an aryl group, R 3a , R 3b may each form a ring-fused arene ring together with Z 1a , Z 1b .

[0080] The substitution numbers m3a and m3b of R 3a and R 3b may each be an integer of 0 or more, and can be appropriately selected according to the types of Z 1a , Z 1b , and may be, for example, an integer of about 0 to 6, preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and still more preferably 0 or 1 (for example, 0). m3a and m3b may be different from each other, but it is preferred that they are the same. Also, when m3a is 2 or more, the types of 2 or more R 3a may each be the same as or different from each other; when m3b is 2 or more, the types of 2 or more R 3b may each be the same as or different from each other.

[0081] The substitution positions of R 3a , R 3b are not particularly limited, and in Z 1a , Z 1b , it may be a position other than the bonding position with the 9-position of the fluorene ring and the bonding positions with X 1a , X 1b , and for example, it may be substituted or bonded to the ortho position (the carbon atom adjacent to the carbon atom to which X 1a , Z 1b is bonded) with respect to X 1a , X 1b in Z 1a , X 1b .

[0082] A typical fluorene compound (F1) is, for example, in formula (1) above, R 1 represents a hydrocarbon group, and m1 represents an integer from 0 to 4. Z 1a and Z 1b C is independent 6-18 Showing an arene ring, X 1a and X 1b The base [-O-(A 1 O) n1 -H](wherein, A 1 represents an alkylene group, and n1 represents a non-negative integer. ), group [-C(=O)-R 2 ][wherein, R 2 is a hydroxyl group, group [-OR h ](wherein, R h represents a hydrocarbon group. ), represents a halogen atom, an amino group, or a substituted amino group. ] represents an amino group or a substituted amino group, and p1a and p1b independently represent integers from 1 to 2. R 3a and R 3b m3a and m3b independently represent a hydrocarbon group, and are compounds in which m3a and m3b independently represent integers from 0 to 4;

[0083] Preferably, R 1 m1 represents an alkyl or aryl group, and m1 represents an integer from 0 to 3. Z 1a and Z 1b C is independent 6-14 Showing an arene ring, X 1a and X 1b The base [-O-(A 1 O) n1 -H](wherein, A 1 is C 2-6 This indicates an alkylene group, where n1 is an integer from 0 to 10. ) , group [-C(=O)-R 2 ][wherein, R 2 is a hydroxyl group, group [-OR h ](wherein, R h is C 1-6This represents an alkyl group such as an alkyl group. ), a halogen atom, an amino group, or a substituted amino group. ], an amino group, or a substituted amino group, where p1a and p1b independently represent integers from 1 to 2. R 3a and R 3b m3a and m3b are compounds that independently represent an alkyl or aryl group, and m3a and m3b are compounds that independently represent an integer between 0 and 3;

[0084] More preferably, R 1 is C 1-6 Alkyl or C 6-12 It indicates an aryl group, and m1 is an integer between 0 and 2. Z 1a and Z 1b These are independently C2 rings such as benzene rings, naphthalene rings, and biphenyl rings. 6-12 Showing an arene ring, X 1a and X 1b The base [-O-(A 1 O) n1 -H](wherein, A 1 is C 2-4 An alkylene group is indicated, where n1 is an integer from 0 to 3. An amino group or substituted amino group is indicated, where p1a and p1b represent 1. R 3a and R 3b C is independent 1-6 Alkyl or C 6-12 This compound exhibits an aryl group, and m3a and m3b independently represent integers between 0 and 2.

[0085] A specific example of a fluorene compound (F1) is, for example, in formula (1) above, X 1a ,X 1b The base [-O-(A 1 O) n1 -H](wherein, A 1 ∫ represents an alkylene group, and n1 represents 0. ) and p1a and p1b are 1 in 9,9-bis(hydroxyaryl)fluorenes (F1-1);X 1a ,X 1b The base [-O-(A 1 O)n1 -H](wherein, A 1 ) represents an alkylene group, and n1 represents an integer greater than or equal to 1 (for example, around 1 to 10). ) and p1a and p1b are 1. 9,9-Bis[hydroxy(poly)alkoxyaryl]fluorenes (F1-2);X 1a ,X 1b Examples include 9,9-bis(aminoaryl)fluorenes (F1-3) in which is an amino group or a substituted amino group and p1a and p1b are 1.

[0086] In this specification and in the claims, unless otherwise specified, "(poly)alkoxy" is used to mean both alkoxy groups and polyalkoxy groups.

[0087] Examples of 9,9-bis(hydroxyaryl)fluorenes (F1-1) include 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(alkyl-hydroxyphenyl)fluorene, 9,9-bis(aryl-hydroxyphenyl)fluorene, and 9,9-bis(hydroxynaphthyl)fluorene.

[0088] Examples of 9,9-bis(hydroxyphenyl)fluorene include 9,9-bis(4-hydroxyphenyl)fluorene.

[0089] Examples of 9,9-bis(alkyl-hydroxyphenyl)fluorene include 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorene, and other 9,9-bis[(mono or di)C 1-4 Examples include alkyl-hydroxyphenyl fluorene.

[0090] Examples of 9,9-bis(aryl-hydroxyphenyl)fluorene include 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-diphenylphenyl)fluorene, and other 9,9-bis((mono or di)C 6-10Examples include aryl-hydroxyphenyl ()fluorene.

[0091] Examples of 9,9-bis(hydroxynaphthyl)fluorene include 9,9-bis(6-hydroxy-2-naphthyl)fluorene and 9,9-bis(5-hydroxy-1-naphthyl)fluorene.

[0092] Examples of 9,9-bis[hydroxy(poly)alkoxyaryl]fluorenes (F1-2) include 9,9-bis[hydroxy(poly)alkoxyphenyl]fluorene, 9,9-bis[alkyl-hydroxy(poly)alkoxyphenyl]fluorene, 9,9-bis[aryl-hydroxy(poly)alkoxyphenyl]fluorene, and 9,9-bis[hydroxy(poly)alkoxynaphthyl]fluorene.

[0093] Examples of 9,9-bis[hydroxy(poly)alkoxyphenyl]fluorene include 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)phenyl]fluorene, and other 9,9-bis[hydroxy(mono or deca)C 2-4 Examples include alkoxyphenyl fluorene.

[0094] Examples of 9,9-bis[alkyl-hydroxy(poly)alkoxyphenyl]fluorene include 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)-3,methylphenyl]fluorene, and other 9,9-bis[(mono or di)C 1-4 Alkyl-hydroxy(mono or deca)C 2-4 Examples include alkoxyphenyl fluorene.

[0095] Examples of 9,9-bis[aryl-hydroxy(poly)alkoxyphenyl]fluorene include 9,9-bis[C 6-10 aryl-hydroxy(mono to deca)C 2-4 alkoxy-phenyl]fluorene, such as 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene and 9,9-bis(4-(2-hydroxypropoxy)-3-phenylphenyl)fluorene.

[0096] Examples of 9,9-bis[hydroxy(poly)alkoxynaphthyl]fluorene include 9,9-bis[hydroxy(mono to deca)C 2-4 alkoxy-naphthyl]fluorene, such as 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene, 9,9-bis[5-(2-hydroxyethoxy)-1-naphthyl]fluorene, and 9,9-bis[6-(2-hydroxypropoxy)-2-naphthyl]fluorene.

[0097] Examples of 9,9-bis(aminoaryl)fluorenes (F1-3) include 9,9-bis(aminoC 6-12 aryl)fluorene, such as 9,9-bis(4-aminophenyl)fluorene.

[0098] Preferred fluorene compounds (F1) include 9,9-bis(hydroxyaryl)fluorenes (F1-1), 9,9-bis[hydroxy(poly)alkoxyaryl]fluorenes (F1-2), and 9,9-bis(aminoaryl)fluorenes (F1-3). Among them, from the viewpoint of being likely to exhibit antiviral properties even at low concentrations, 9,9-bis(hydroxyaryl)fluorenes (F1-1) are preferred. In addition to antiviral properties, 9,9-bis[hydroxy(poly)alkoxyaryl]fluorenes (F1-2) are preferred in terms of good compatibility with the polymer component and easy suppression of coloring or discoloration.

[0099] The total proportion of fluorene compounds (F1-1), (F1-2), and (F1-3) relative to the total amount of fluorene compound (F1) is, for example, 10 mol% or more (for example, 10 to 100 mol%), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, and more preferably substantially 100 mol%. Furthermore, the proportion of fluorene compound (F1-1) may be, for example, 10 mol% or more (e.g., 10 to 100 mol%) relative to the total fluorene compound (F1), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, or substantially 100 mol%; the proportion of fluorene compound (F1-2) may be, for example, 10 mol% or more (e.g., 10 to 100 mol%) relative to the total fluorene compound (F1), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, or substantially 100 mol%; and the proportion of fluorene compound (F1-3) may be, for example, 10 mol% or more (e.g., 10 to 100 mol%) relative to the total fluorene compound (F1), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, or substantially 100 mol%.

[0100] (F2) Compounds having a 9,9-bisalkylfluorene skeleton The fluorene compound (F2) can be any compound that has a 9,9-bisalkylfluorene skeleton in its chemical structure, such as the compound represented by the following formula (2).

[0101] [ka]

[0102] (In the formula, R 4 represents a substituent, and m4 represents an integer from 0 to 8. A 2a and A 2b This independently represents an alkylene group which may have substituents, X 2a and X 2b (These independently represent heteroatom-containing functional groups.)

[0103] In equation (2) above, R 4 Examples of substituents represented by R 1 Examples include groups similar to the substituents described above. 4 Typical substituents represented are halogen atoms, hydrocarbon groups, and groups [-OR h Examples of alkyl groups include alkoxy groups, acyl groups, and preferably hydrocarbon groups, more preferably alkyl groups, and especially aryl groups (particularly aryl groups). Examples of alkyl groups (linear or branched alkyl groups) include methyl groups, ethyl groups, t-butyl groups, etc. 1-6 Examples include alkyl groups, such as methyl groups and C 1-4 Alkyl groups are preferred. Examples of aryl groups include C such as phenyl groups. 6-10 Examples include aryl groups.

[0104] R 4 The number of substitutions m4 is an integer from 0 to 8, for example, an integer from about 0 to 6, preferably an integer from 0 to 4, an integer from 0 to 2 (for example, 0 or 1), more preferably 0 or 2, and especially 2. Note that if m4 is 2 or more, then 2 or more R 4 The types may be the same or different from each other. Also, of the two benzene rings that form the fluorene skeleton, both benzene rings may have R 4 If substitution occurs, then the R of one of the benzene rings 4 The type and the R of the other benzene ring 4 The types may be different from each other, but it is preferable that they be the same. Also, R 4 The substitution site is not particularly limited as long as it is at positions 1 to 8 of the fluorene skeleton, for example, it may be at positions 2, 3, 2,7, etc.

[0105] A 2a Or A 2bIn an alkylene group which may have substituents represented by , the alkylene group (linear or branched alkylene group) may be, for example, a methylene group, an ethylene group, a trimethylene group, a propylene group, a 1,2-butanediyl group, a 2-methylpropane-1,3-diyl group, etc. 1-8 Examples of alkylene groups include methylene groups, preferably methylene groups, ethylene groups, trimethylene groups, propylene groups, 2-methylpropane-1,3-diyl groups, etc. 1-6 An example is an alkylene group, more preferably C 1-4 It is an alkylene group, and more preferably C 1-3 Alkylene group or C 2-4 These are alkylene groups, and among them, C groups such as ethylene, propylene, and trimethylene. 2-3 Alkylene groups are preferred, and ethylene groups are particularly preferred.

[0106] A 2a and A 2b In this, each alkylene group (linear or branched alkylene group) may have one or more substituents, and examples of substituents include hydrocarbon groups such as cycloalkyl groups, aryl groups, and aralkyl groups, and carboxyl groups, preferably C 5-12 Hydrocarbon groups such as hydrocarbon groups, and more preferably aryl groups (e.g., phenyl groups such as C 6-10 The alkylene group is an aryl group. The number of substituents (substitutions) on the alkylene group is, for example, an integer of about 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and especially 0.

[0107] X 2a or X 2bThe heteroatom-containing functional group represented by may be any group containing at least one heteroatom. Examples of heteroatoms include nitrogen atoms, oxygen atoms, and sulfur atoms, with nitrogen atoms and oxygen atoms being preferred, and oxygen atoms being more preferably preferred. The number of heteroatoms in the heteroatom-containing functional group is, for example, an integer from 1 to 20, preferably in stages from 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, and 1 to 3, and more preferably 1 or 2, particularly 2.

[0108] X 2a ,X 2b Examples of heteroatom-containing functional groups represented by the group [-O-(A 3 O) n3 -H](wherein, A 3 represents an alkylene group, and n3 represents a non-negative integer. ), group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h represents a hydrocarbon group. ), a halogen atom, an amino group, or a substituted amino group. Examples include ], an amino group, a substituted amino group, etc.

[0109] Base [-O-(A 3 O) n3 -H] represents a hydroxyl group or a hydroxy(mono or poly)alkoxy group. 3 Examples of alkylene groups (linear or branched alkylene groups) represented by A include, for example, the above A 1 The same applies to the alkylene group exemplified as an example, including preferred embodiments.

[0110] Alkylene oxy group [-(A 3 The number of repetitions (number of added moles) n3 of O)-] should be 0 or greater, and can be selected from a range of approximately 0 to 15, preferably in the following increments: 0 to 10, 0 to 8, 0 to 6, 0 to 4, 0 to 2, 0 to 1, and especially 0.

[0111] In this specification and in the claims, the "number of repetitions (number of added moles)" may be an integer, an average value (arithmetic mean, arithmetic mean), or an average number of added moles, and in either case, the preferred embodiment may be the same as the preferred range described above. When n3 is in a moderate range that is not too large, it tends to be easier to suppress the decrease in heat resistance and refractive index. Also, when n3 is 2 or more, 2 or more alkylene oxy groups [-(A 3 The types of O)-] may be different from each other, but it is preferable that they be the same.

[0112] Group [-C(=O)-R 5 ] is a carboxyl group (R 5 A group derived from a hydroxyl group or a carboxyl group (for example, R 5 is based on [-OR h ] is a carboxylic acid ester group, R 5 R is a halogen atom in the carboxylic acid halide group. 5 This corresponds to an amino group or a carboxyl amide group which is a substituted amino group. In the case of a carboxyl group, it may also be in the form of an acid anhydride or the like.

[0113] R 5 is based on [-OR h If ] then R h Examples of hydrocarbon groups represented by the above R 1 Examples include the hydrocarbon groups described as such, and similar groups including preferred embodiments. Also, R 5 As a base [-OR h ] is, for example, the R 1 The base described as [-OR h Examples include similar groups, including preferred embodiments. Representative group [-C(=O)-OR h For example, the aforementioned group [-C(=O)-R 2 The base described as ] is [-C(=O)-OR h Similar groups include those mentioned above, including preferred embodiments.

[0114] R 5If is a halogen atom, the halogen atom is, for example, the R 2 Examples include halogen atoms listed as such, and a representative group is [-C(=O)-R 5 ](wherein, R 5 This indicates a halogen atom. Examples include halocarbonyl groups such as chlorocarbonyl groups.

[0115] R 5 If is an amino group or a substituted amino group (mono or disubstituted amino group), the substituted amino group may be, for example, the R 1 Examples include the substituted amino group described above, and similar groups, including preferred embodiments. A representative group is [-C(=O)-R 5 ](wherein, R 5 This represents an amino group or a substituted amino group.) For example, the group [-C(=O)-R 2 ](wherein, R 2 This indicates an amino group or a substituted amino group. Examples include groups similar to those described as (and preferred embodiments).

[0116] X 2a ,X 2b When the heteroatom-containing functional group represented by is a substituted amino group (mono or disubstituted amino group), the substituted amino group is, for example, the R 1 Examples include the substituted amino groups described above, and similar groups, including preferred embodiments.

[0117] X 2a ,X 2b A preferred heteroatom-containing functional group represented by the group [-O-(A 1 O) n1 -H](wherein, A 1 represents an alkylene group, and n1 represents an integer from 0 to 10. ) , group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h represents a hydrocarbon group. ), an amino group or a substituted amino group. ], an amino group, a substituted amino group; more preferably a group [-O-(A 1 O)n1 -H](wherein, A 1 is C 2-6 This indicates an alkylene group, where n1 is an integer from 0 to 3. ) , group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h [-C(=O)-R] represents a hydrocarbon group such as an alkyl group. , an amino group or a substituted amino group. , an amino group, a substituted amino group; more preferably, from the viewpoint of antiviral activity, the group [-C(=O)-R] 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h is C 1-10 It represents a hydrocarbon group such as a hydrocarbon group, an amino group or a substituted amino group; among these, the group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h is C 1-6 It represents an alkyl group such as an alkyl group, an amino group or a substituted amino group; in particular, the group [-C(=O)-R 5 ][wherein, R 5 is the base [-OR h ](wherein, R h is C 1-4 It shows alkyl groups such as alkyl groups. ) It is ]. In addition to its antiviral properties, it has good compatibility with polymer components and is easy to suppress staining or discoloration, so X 2a ,X 2b The heteroatom-containing functional group represented by is preferably an amino group or a substituted amino group, and more preferably an amino group. 2a and X 2b The types may be different from each other, but it is preferable that they be the same.

[0118] A typical fluorene compound (F2) is, for example, in formula (2) above, R 4 represents a hydrocarbon group, and m4 represents an integer from 0 to 4. A2a and A 2b This independently represents an alkylene group which may have a hydrocarbon group, X 2a and X 2b The base [-O-(A 3 O) n3 -H](wherein, A 3 represents an alkylene group, and n3 represents a non-negative integer. ), group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](where R h ) indicates a hydrocarbon group. ), a halogen atom, an amino group, or a substituted amino group. ], an amino group, or a substituted amino group is a compound;

[0119] Preferably, R 4 m4 represents an alkyl or aryl group, and m4 represents an integer from 0 to 3. A 2a and A 2b This independently represents an alkylene group which may have a hydrocarbon group such as an aryl group. X 2a and X 2b The base [-O-(A 3 O) n3 -H](wherein, A 3 is C 2-4 This indicates an alkylene group, where n3 is an integer from 0 to 3. ) , group [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](where R h This indicates a hydrocarbon group such as an alkyl group. It also indicates an amino group or a substituted amino group. This is a compound that indicates an amino group or a substituted amino group;

[0120] More preferably, R 4 is C 1-6 Alkyl or C 6-12 It indicates an aryl group, and m4 represents an integer from 0 to 2. A 2a and A 2b C is independent6-12 C which may have an aryl group 1-6 Showing an alkylene group, X 2a and X 2b The base [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h is C 1-6 It is a compound that shows an alkyl group such as an alkyl group, an amino group or a substituted amino group;

[0121] Particularly preferred, R 4 is C 1-4 Alkyl or C 6-10 It indicates an aryl group, and m4 represents an integer from 0 to 2. A 2a and A 2b C is independent 1-4 Showing an alkylene group, X 2a and X 2b The base [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group, group [-OR h ](wherein, R h is C 1-6 It is a compound that shows an alkyl group, such as an alkyl group.

[0122] A specific example of a fluorene compound (F2) is, for example, in formula (2) above, X 2a ,X 2b The base is [-C(=O)-R 5 ][wherein, R 5 is a hydroxyl group or group [-OR h ](wherein, R h indicates a hydrocarbon group. ) indicates ] 9,9-bis(carboxyalkyl)fluorenes (F2-1);X 2a ,X 2b The base is [-C(=O)-R 5 ](wherein, R 5∫ indicates an amino group or a substituted amino group. Examples include 9,9-bis(carbamoylalkyl)fluorenes (F2-2), which are ∫

[0123] Examples of 9,9-bis(carboxyalkyl)fluorenes (F2-1) include 9,9-bis(carboxyalkyl)fluorene, 9,9-bis(carboxyalkyl)-diarylfluorene, or esters thereof.

[0124] Examples of 9,9-bis(carboxyalkyl)fluorene include 9,9-bis(2-carboxyethyl)fluorene, 9,9-bis(2-carboxypropyl)fluorene, and other 9,9-bis(carboxyC 1-6 Examples include alkyl fluorene.

[0125] Examples of 9,9-bis(carboxyalkyl)-diarylfluorenes include 9,9-bis(2-carboxyethyl)-2,7-diphenylfluorene, 9,9-bis(2-carboxyethyl)-2,7-di(2-naphthyl)fluorene, 9,9-bis(2-carboxyethyl)-2,7-di(1-naphthyl)fluorene, and 9,9-bis(2-carboxypropyl)-2,7-di(2-naphthyl)fluorene, etc. 1-6 Alkyl)-diC 6-12 Examples include aryl fluorene.

[0126] Examples of these esters include linear or branched alkyl esters, specifically methyl esters, ethyl esters, t-butyl esters, and other C13 esters. 1-6 Alkyl esters, preferably C 1-4 Alkyl esters are an example.

[0127] Examples of 9,9-bis(carbamoylalkyl)fluorenes (F2-2) include 9,9-bis(carbamoyl C 2-3 Alkyl)fluorene, 9,9-bis(alkylcarbamoyl C 2-3Examples include alkyl fluorene.

[0128] 9,9-bis(carbamoyl C) 2-3 Examples of alkyl)fluorenes include 9,9-bis(2-carbamoylethyl)fluorene, 9,9-bis(2-carbamoylpropyl)fluorene, and other 9,9-bis(carbamoyl C 1-6 Examples include alkyl fluorene.

[0129] 9,9-Bis(alkylcarbamoyl C) 2-3 Examples of alkyl)fluorenes include 9,9-bis[2-(N-methylcarbamoyl)ethyl]fluorene, 9,9-bis[2-(N-methylcarbamoyl)propyl]fluorene, 9,9-bis[2-(N-ethylcarbamoyl)ethyl]fluorene, 9,9-bis[2-(N-isopropylcarbamoyl)ethyl]fluorene, 9,9-bis[2-(N-isopropylcarbamoyl)propyl]fluorene, 9,9-bis[2-(N-butylcarbamoyl)ethyl]fluorene, 9,9-bis[ 9,9-bis[(mono or di)C]fluorene such as 2-(N,N-dimethylcarbamoyl)ethyl]fluorene, 9,9-bis[2-(N,N-dimethylcarbamoyl)propyl]fluorene, 9,9-bis[2-(N,N-diethylcarbamoyl)propyl]fluorene, 9,9-bis[2-(N,N-diisopropylcarbamoyl)ethyl]fluorene, 9,9-bis[2-(N,N-dibutylcarbamoyl)ethyl]fluorene, etc. 1-6 (Alkyl-carbamoyl)C 1-6 Examples include alkylfluorene.

[0130] Preferred fluorene compounds (F2) include 9,9-bis(carboxyalkyl)fluorenes (F2-1) and 9,9-bis(carbamoylalkyl)fluorenes (F2-2). Among these, 9,9-bis(carboxyalkyl)fluorenes (F2-1) are preferred from the viewpoint of antiviral activity, while 9,9-bis(carbamoylalkyl)fluorenes (F2-2) are preferred in addition to their antiviral activity, due to their good compatibility with polymer components and ease of suppressing discoloration or staining.

[0131] The total proportion of fluorene compounds (F2-1) and (F2-2) relative to the total amount of fluorene compound (F2) is, for example, 10 mol% or more (for example, 10 to 100 mol%), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, and more preferably substantially 100 mol%. Furthermore, the proportion of fluorene compound (F2-1) may be, for example, 10 mol% or more (e.g., 10 to 100 mol%) relative to the total fluorene compound (F2), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, or substantially 100 mol%; the proportion of fluorene compound (F2-2) may be, for example, 10 mol% or more (e.g., 10 to 100 mol%) relative to the total fluorene compound (F2), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, or substantially 100 mol%.

[0132] (F3)9-fluorenone skeleton compounds Fluorene compounds (F3) can be any compound that has a 9-fluorenone skeleton in its chemical structure, such as the compound represented by the following formula (3).

[0133] [ka]

[0134] (In the formula, R 6 (where 'm' indicates a substituent, and m6 represents an integer between 0 and 8.)

[0135] In equation (3) above, R 6 Examples of substituents represented by R 1 Examples include groups similar to the substituents described above. 6 Typical substituents represented are halogen atoms, hydrocarbon groups, and groups [-OR h Examples of alkyl groups include alkoxy groups, acyl groups, and preferably hydrocarbon groups, more preferably alkyl groups, and especially aryl groups (particularly aryl groups). Examples of alkyl groups (linear or branched alkyl groups) include methyl groups, ethyl groups, t-butyl groups, etc. 1-6 Examples include alkyl groups, such as methyl groups and C 1-4 Alkyl groups are preferred. Examples of aryl groups include C such as phenyl groups. 6-10 Examples include aryl groups.

[0136] R 6 The number of substitutions m6 is an integer between 0 and 8, for example, an integer between 0 and 6, preferably in stages below, an integer between 0 and 4, an integer between 0 and 2 (for example, 0 or 1), and more preferably 0 or 2. Note that if m6 is 2 or more, then 2 or more R 6 The types may be the same or different from each other. Also, of the two benzene rings that form the fluorene skeleton, both benzene rings may have R 6 If substitution occurs, then the R of one of the benzene rings 6 The type and the R of the other benzene ring 6 The types may be different from each other, but it is preferable that they be the same. Also, R 6 The substitution site is not particularly limited as long as it is at positions 1 to 8 of the fluorene skeleton, for example, it may be at positions 2, 3, 2,7, etc.

[0137] A typical fluorene compound (F3) is, for example, in formula (3) above, R 6 m6 represents a hydrocarbon group, and m6 is a compound representing an integer between 0 and 4; Preferably, R 6m6 represents an alkyl or aryl group, and m6 is an integer between 0 and 3; More preferably, R 6 is C 1-6 Alkyl or C 6-12 It is a compound exhibiting an aryl group, where m6 is an integer between 0 and 2; Particularly preferred, R 6 is C 1-4 Alkyl or C 6-10 This compound exhibits an aryl group, and m6 is an integer between 0 and 2.

[0138] Specific examples of fluorene compounds (F3) include, for instance, 9-fluorenone.

[0139] Compounds having a (F4)9H-fluorene skeleton Fluorene compounds (F4) can be any compound that has a 9H-fluorene skeleton (a fluorene skeleton with an unsubstituted 9-position) in its chemical structure, such as the compound represented by the following formula (4).

[0140] [ka]

[0141] (In the formula, R 7 (where represents a substituent, and m7 represents an integer between 0 and 8.)

[0142] In equation (4) above, R 7 Examples of substituents represented by R 1 Examples include groups similar to the substituents described above. 7 Typical substituents represented are halogen atoms, hydrocarbon groups, and groups [-OR h Examples of alkyl groups include alkoxy groups, acyl groups, and preferably hydrocarbon groups, more preferably alkyl groups, and especially aryl groups (particularly aryl groups). Examples of alkyl groups (linear or branched alkyl groups) include methyl groups, ethyl groups, t-butyl groups, etc. 1-6Examples include alkyl groups, such as methyl groups and C 1-4 Alkyl groups are preferred. Examples of aryl groups include C such as phenyl groups. 6-10 Examples include aryl groups.

[0143] R 7 The number of substitutions m7 is an integer between 0 and 8, for example, an integer between 0 and 6, preferably in stages below, an integer between 0 and 4, an integer between 0 and 2 (for example, 0 or 1), and more preferably 0 or 2. Note that if m7 is 2 or more, then 2 or more R 7 The types may be the same or different from each other. Also, of the two benzene rings that form the fluorene skeleton, both benzene rings may have R 7 If substitution occurs, then the R of one of the benzene rings 7 The type and the R of the other benzene ring 7 The types may be different from each other, but it is preferable that they be the same. Also, R 7 The substitution site is not particularly limited as long as it is at positions 1 to 8 of the fluorene skeleton, for example, it may be at positions 2, 3, 2,7, etc.

[0144] A typical fluorene compound (F4) is, for example, in formula (4) above, R 7 m7 represents a hydrocarbon group, and m7 is an integer between 0 and 4 in the compound; Preferably, R 7 m7 represents an alkyl or aryl group, and m7 is a compound representing an integer between 0 and 3; More preferably, R 7 is C 1-6 Alkyl or C 6-12 It is a compound exhibiting an aryl group, where m7 is an integer between 0 and 2; Particularly preferred, R 7 is C 1-4 Alkyl or C 6-10 This compound exhibits an aryl group, and m7 is an integer between 0 and 2.

[0145] Specific examples of fluorene compounds (F4) include, for instance, 9H-fluorene.

[0146] The antiviral agents of this disclosure may contain fluorene compounds alone or in combination of two or more. The fluorene compound is at least one selected from fluorene compounds (F1), (F2), and (F3) in terms of particularly excellent balance between heat resistance and antiviral properties; more preferably, at least one selected from fluorene compounds (F1) and (F2); in particular, it is preferable to include fluorene compound (F1).

[0147] The total amount of fluorene compounds (F1), (F2), (F3), and (F4) [preferably the total amount of fluorene compounds (F1), (F2), and (F3); more preferably the total amount of fluorene compounds (F1) and (F2); in particular, fluorene compound (F1)] is, for example, 10 mol% or more (for example, 10 to 100 mol%), preferably in stages, 50 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, and more preferably substantially 100 mol%.

[0148] Furthermore, fluorene compounds such as (F1) to (F4) may also be in the form of salts and / or solvates. For example, if a fluorene compound has a functional group (substituent) capable of forming a salt, such as a carboxyl group, amino group, or hydroxyl group, it may be in the form of a salt. Examples of salts include inorganic salts (e.g., hydrochloride, hydrobromide, sulfate, nitrate, phosphate, etc.); organic salts (e.g., carboxylates such as acetate, propionate, tartrate, fumarate, maleate, malate, citrate, methanesulfonate, p-toluenesulfonate, etc.); metal salts (e.g., alkali metal salts such as sodium salt, potassium salt, alkaline earth metal salts such as calcium salt, magnesium salt, etc.); amine salts (ammonium salts) [e.g., ammonium salt (NH4 +Examples include mono- or tetraalkylammonium salts, mono- or tetra(hydroxyalkyl)ammonium salts, and other mono- or tetrasubstituted ammonium salts; heterocyclic ammonium salts such as morpholinium salts, piperidinium salts, and pyrrolidinium salts.

[0149] Examples of solvents in the form of solvates include water; organic solvents such as ethanol, glycerol, and acetic acid.

[0150] The molecular weight of fluorene compounds such as fluorene compounds (F1) to (F4) is not particularly limited, but may be, for example, 3000 or less (e.g., 166 to 2000), preferably in the following increments: 1500 or less (e.g., 180 to 1200), 1000 or less (e.g., 200 to 900), 800 or less (e.g., 250 to 750), 700 or less (e.g., 300 to 650), and 600 or less. When the molecular weight is within a moderate range that is not too large, it is easier to improve compatibility or dispersibility with solvents (or dispersion media) and polymer components, and the appearance of the coating layer (coating film) and molded articles of polymer compositions (injection molded articles, etc.) tends to be good. In addition, when the molecular weight is within a moderate range that is not too large, the fluorene compound tends to bleed out more easily to the surface of the coating layer and molded articles, so the antiviral performance tends to be high. When the molecular weight is within a moderate range, not too small, it tends to improve heat resistance.

[0151] Furthermore, the 5% weight loss temperature (Td5) of fluorene compounds such as fluorene compounds (F1) to (F4) may be, for example, around 250°C or higher (e.g., around 280 to 500°C), and preferably, in stages, 300°C or higher (e.g., 320 to 450°C), 350 to 450°C, 360 to 440°C, 370 to 430°C, 380 to 420°C, and 390 to 410°C. Thus, fluorene compounds have high heat resistance. Therefore, they can be effectively used as antiviral agents while suppressing decomposition even in high-temperature environments.

[0152] In this specification and in the claims, the 5% weight loss temperature can be measured by the method described in the examples below.

[0153] The fluorene compound may be crystalline or amorphous.

[0154] The fluorene compound may be a commercially available product or may be manufactured according to or in accordance with known methods. Specifically, the fluorene compound (F1) may be, for example, R 1 and the 9-fluorenone compounds corresponding to m1 (e.g., 9-fluorenone, etc.), and Z 1a ,Z 1b , X 1a ,X 1b , p1a, p1b, R 3a ,R 3b These can be produced by reacting arene ring-containing compounds corresponding to m3a and m3b (e.g., phenol, naphthol, hydroxybiphenyl, 2-phenoxyethanol, 2-naphthoxyethanol, aniline, etc.) in the presence of a catalyst (e.g., an acid catalyst such as sulfuric acid) or a co-catalyst (thiols such as 3-mercaptopropionic acid); the fluorene compound (F2) can be produced, for example, R 4 And 9H-fluorene compounds (such as 9H-fluorene) corresponding to m4, and A 2a ,A 2b and X 2a ,X 2b It may also be produced by reacting a corresponding compound [for example, (meth)acrylic acids ((meth)acrylic acid, (meth)acrylic acid esters, (meth)acrylamide, etc.), halogenated alkanoic acids (for example, bromoalkanoic acid esters such as methyl bromoacetate and methyl bromobutyrate, etc.)] under predetermined conditions (for example, under basic conditions).

[0155] [Antiviral agents] Fluorene compounds are suitable as active ingredients in antiviral agents because they possess antiviral properties (antiviral activity). In this specification and in the claims, "antiviral" includes suppressing viral replication, killing (or eliminating), removing or weakening (or reducing) viruses, and reducing the infectivity of viruses.

[0156] Fluorene compounds are effective antiviral agents against enveloped viruses (viruses with an envelope) and / or non-enveloped viruses (viruses without an envelope).

[0157] Enveloped viruses (viruses that have an envelope) include, for example, orthomyxoviruses [e.g., influenza viruses (types A, B, C, etc.), togotoviruses, etc.], matonaviruses (rubiviruses such as rubella virus), paramyxoviruses (morbilliviruses such as measles virus, rubraviruses such as mumps virus, henipaviruses such as nipah virus, etc.), pneumoviruses (orthopneumoviruses such as respiratory syncytial virus), and herpesviruses [herpes simplex virus, varicella virus (varicella-zoster virus, etc.)]. Examples include alphaherpesviruses, coronaviruses (such as the SARS virus), hepadnaviruses (such as orthohednaviruses like the hepatitis B virus), flaviviruses (such as hepathiviruses like the hepatitis C virus, yellow fever virus, dengue virus, and Japanese encephalitis virus), deltaviruses (such as the hepatitis D virus), retroviruses (such as the human immunodeficiency virus), rhabdoviruses (such as lyssaviruses like the rabies virus), filoviruses (such as the Ebola virus), and bunyaviruses (such as the hantavirus).

[0158] Examples of non-enveloped viruses (viruses that do not have an envelope) include caliciviruses [e.g., norovirus, sapovirus, vegivirus (feline calicivirus, etc.), lagowvirus, nebovirus], picornaviruses (hepatoviruses such as hepatitis A virus, enteroviruses, poliovirus, coxsackievirus, enteroviruses such as echovirus, cardioviruses such as encephalomyocarditis virus, rhinovirus, etc.), hepeviruses (hepatitis E virus, etc.), adenoviruses (mastoadenoviruses such as human adenovirus, etc.), reoviruses (rotavirus, etc.), papillomaviruses (human papillomavirus, etc.), and parvoviruses (erythroviruses such as human parvovirus, etc.).

[0159] Viruses possess genes, which are contained within an outer shell protein called a capsid. Therefore, viruses can be broadly classified not only based on whether or not the capsid is covered by an envelope, but also based on whether their genes are DNA or RNA.

[0160] Specifically, enveloped viruses, whose genes are DNA, include herpesviruses and hepatitis B virus; non-enveloped viruses, whose genes are DNA, include adenoviruses, human papillomaviruses and human parvoviruses; enveloped viruses, whose genes are RNA, include orthomyxoviruses such as influenza virus, rubella virus, measles virus, mumps virus, nipah virus, coronavirus, hepatitis C virus, hepatitis D virus, respiratory syncytial virus (RSV), human immunodeficiency virus, yellow fever virus, dengue virus, lyssavirus (rabies virus, etc.), Ebola virus, and hantavirus; and non-enveloped viruses, whose genes are RNA, include norovirus, sapovirus, caliciviruses such as feline calicivirus, hepatitis A virus, enterovirus, poliovirus, coxsackievirus, echovirus, encephalomyocarditis virus, rhinovirus, hepatitis E virus, and rotavirus.

[0161] The antiviral agents disclosed herein exhibit a broad antiviral spectrum and are not particularly limited in their target viruses. For example, they are highly effective against both enveloped viruses (especially orthomyxoviruses such as influenza virus) and non-enveloped viruses (especially caliciviruses such as feline calicivirus). They are particularly effective against enveloped viruses such as orthomyxoviruses (especially influenza virus) and non-enveloped viruses such as caliciviruses (especially feline calicivirus).

[0162] The virus may also be an arbovirus (yellow fever virus, dengue virus, or Japanese encephalitis virus).

[0163] The antiviral agents of this disclosure may consist solely of a fluorene compound (the first active ingredient), and may optionally include, in addition to the fluorene compound, other or conventional antiviral agents as a second active ingredient. The second active ingredient may be included alone or in combination of two or more.

[0164] The proportion of the fluorene compound (first active ingredient) to the total active ingredients may be, for example, about 10% by mass or more, preferably in stages of 30% by mass or more, 50% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, and preferably substantially 100% by mass.

[0165] The antiviral agent disclosed herein may be in various dosage forms (formulation forms) in addition to the fluorene compound as the active ingredient, depending on its purpose and use. The dosage form is not particularly limited and examples include liquid preparations such as suspensions, wettable powders, flowables, dispersants, emulsions, and oils; solid preparations such as powders, granules, fine granules (or powder-granules), powders, microcapsules, microspheres, and foaming agents; semi-solid preparations such as pastes and creams; and sprays, aerosols, fumigants, and vaporizers. These dosage forms may be prepared by conventional methods, or depending on the type of dosage form, they may be prepared by dispersing the active ingredient on various carriers such as liquid carriers and solid carriers, or they may be prepared without including these carriers.

[0166] The liquid carrier may be a conventional solvent (solvent or dispersion medium), for example, a polar solvent or a nonpolar solvent. Examples of the liquid carrier include water; alkanols (for example, methanol, ethanol, lower alkanols such as n-propanol, isopropanol, and n-butanol); polyhydric alcohols (for example, mono- or polyalkylene glycols such as ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-butanediol, 1,4-butanediol, and 1,5-pentanediol); mono- or polyalkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether (or methyl cellosolve), ethylene glycol monoethyl ether (or ethyl cellosolve), ethylene glycol monobutyl ether (or butyl cellosolve), diethylene glycol monomethyl ether (or methyl carbitol), diethylene glycol monoethyl ether (or ethyl carbitol), and triethylene glycol monobutyl ether; ketones (for example, acetone, methyl ethyl Chain ketones such as lucetone and methyl isobutyl ketone; ethers (e.g., chain ethers such as diethyl ether, cyclic ethers such as dioxane and tetrahydrofuran); esters (e.g., monocarboxylic acid esters, specifically acetate esters such as ethyl acetate, butyl acetate, isobutyl acetate, and 3-methyl-3-methoxybutyl acetate; dicarboxylic acid esters, specifically alkane dicarboxylic acid esters such as dimethyl succinate, dimethyl glutarate, and dimethyl adipate; cyclic esters such as γ-butyrolactone); carbonates (cyclic carbonates such as propylene carbonate); hydrocarbons (e.g., aromatic hydrocarbons such as benzene, toluene, xylene, methylnaphthalene, dimethylnaphthalene, isopropylnaphthalene, diisopropylnaphthalene, ethylbiphenyl, diethylbiphenyl, and solvent naphtha); halogenated hydrocarbons (e.g., chlorinated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride); nitriles such as acetonitrile;Examples of liquid carriers include amides (e.g., linear amides such as dimethylformamide and dimethylacetamide, and cyclic amides such as N-methyl-2-pyrrolidone); and sulfoxides such as dimethyl sulfoxide. These liquid carriers may be used individually or in combination of two or more. Preferred liquid carriers may include water, lower alkanols, mono- or polyalkylene glycols, ketones, and carbonates such as propylene carbonate.

[0167] As the solid carrier, conventional solid carriers used for antiviral agents and the like may be used. Examples of the solid carrier include mineral powders (e.g., diatomaceous earth, mica, clay, kaolin, talc, silica, bentonite, talc powder, pyrophyllite powder, and other talc-like substances, fine clay powder, calcium carbonate, etc.); sulfur powder; urea powder; and plant-based powders such as wood flour and starch. These solid carriers may be used as excipients, binders, disintegrants, lubricants, and / or fillers. These solid carriers may be used alone or in combination of two or more types.

[0168] The aerosol agent can be manufactured by diluting the active ingredient with a suitable solvent as needed and filling it into a container together with a propellant. Examples of solvents include the liquid carriers described above. Examples of propellants include chlorofluorocarbons (CFCs), CFC substitutes, liquefied natural gas, nitrogen gas, and dimethyl ether.

[0169] Furthermore, the antiviral agent of this disclosure may or may not contain various additives as needed, such as conventional additives such as stabilizers (antioxidants, ultraviolet absorbers, light stabilizers, etc.), buffers, emulsifiers, dispersants, spreading agents, wetting agents, penetrating agents, humectants, water removers, defoaming agents, thickeners, flow aids, anticaking agents, flocculants, ultraviolet scattering agents, colorants (or colorants), fragrances, chelating agents, etc.

[0170] In the antiviral agent of this disclosure, the content of the active ingredient is not particularly limited, but may be, for example, 0.0001 to 100% by mass (for example, 0.001 to 50% by mass) of the total antiviral agent, and other components such as carriers and additives (components other than the active ingredient) may be included in a range that does not significantly affect the antiviral effect or stability, and may not necessarily be included.

[0171] [Uses of antiviral agents, etc.] The antiviral agent disclosed herein can be widely used in various fields requiring antiviral effects (e.g., industrial, cleaning, medical, food, etc.). Examples of applications include application to non-human objects (e.g., articles or substrates), specifically, coating the surface of an article or substrate, or compounding or mixing it with an article or substrate (forming an article or substrate with a composition containing the antiviral agent). This allows for the imparting of antiviral properties (antiviral processing) to the article or substrate. That is, it can exert an antiviral effect against viruses already attached to or about to be attached to the article or substrate, and further, against viruses already attached to or about to be attached to materials that come into contact with the article or substrate.

[0172] The material of the article or base material is not particularly limited and includes, for example, organic materials such as wood, resin or rubber (e.g., polymer components described later), and inorganic materials such as glass, ceramics, and metal.

[0173] Examples of articles or base materials include industrial products or their raw materials used in various fields, such as building materials; equipment or fixtures for designated facilities; vehicle-related products; textiles or textile products; furniture, home appliances or office automation equipment; tableware or cooking utensils; containers or packaging materials; daily necessities or miscellaneous goods; paints or inks; adhesives or sealants; resin or rubber products (for example, molded articles in various shapes such as rods, films, blocks, and special shapes, specifically polyvinyl alcohol films, polyvinyl chloride films, etc.; resins or rubber latex, etc.); or composite materials combining these.

[0174] Examples of the aforementioned building materials include gypsum board, roofing materials, wall materials, flooring materials, joinery, coating paper, wallpaper or wall coverings, exterior floor coverings, windows, screens, doors, doorknobs, handrails, shelves, kitchen counters, sinks, washbasins, mirrors, bathtubs, toilets, sealing materials, tiles, ducts (such as vents, air vents or air inlets), pipes (such as water pipes), drains or drains, rain gutters, fences, and so on.

[0175] Examples of equipment or fixtures for the aforementioned designated facilities include equipment or fixtures that can be used by an unspecified number of people in various facilities such as public facilities (parks, schools, nurseries, government offices, community centers, libraries, museums, civic halls, roads, etc.), public transportation (trains, buses, airplanes, ships, etc.), offices, shops or restaurants, hospitals, etc. Specifically, these include benches, playground equipment, escalator belts, straps, handrails, seats or cushions, automatic ticket gates, and operation panels (or touch panels) or switch components for various devices (elevators, automatic ticket machines, vending machines, ATMs, touch-panel digital signage, heated toilet seats, etc.).

[0176] Examples of the aforementioned vehicle-related products include steering wheels, levers, pedals, saddles, seats, various control panels (or switch components), car air conditioners or their filters, and interior parts.

[0177] The aforementioned fibers include conventional fibers such as natural fibers, synthetic fibers, and other organic and inorganic fibers. Fiber products formed from fibers may be fiber structures such as threads, strings, ropes, nets, and fabrics (woven fabrics, knitted fabrics, nonwoven fabrics, etc.), or processed products using these fiber structures, such as clothing (for example, coats, jackets, trousers, skirts, dress shirts, knit shirts, blouses, sweaters, cardigans, nightwear, underwear, diapers, supporters). Examples include tarpaulins, socks, tights, stockings, gloves, hats, scarves, mufflers, neck wraps, stoles, clothing linings, clothing interlinings, clothing padding, work clothes, uniforms, sportswear, swimwear, school uniforms, etc.), fabric products (for example, curtains, rugs, mats, carpets, rugs, tablecloths, cushion covers, etc.), bedding (for example, blankets, futon fabrics, futon stuffing, futon covers, pillowcases, bedspreads, sheets, etc.), masks, handkerchiefs, towels, dishcloths, rags, and disposable nonwoven fabrics.

[0178] Examples of furniture, home appliances, or office automation equipment include desks, chairs, sofas, shelves, ventilation fans, electric fans, air circulators, air conditioning equipment, humidifiers, dehumidifiers, air purifiers, vacuum cleaners, filters for various devices, refrigerators, microwave ovens, dishwashers, washing machines, hair dryers, personal computers and their peripherals, tablet devices, smartphones, mobile phones, and remote controls or switch components for various devices.

[0179] Examples of tableware or cooking utensils include plates, cups, chopsticks, spoons, forks, knives, cutting boards, bowls, strainers, frying pans, pots, kettles, blenders, spatulas, turners, ladles, tongs, and spoons.

[0180] Examples of containers or packaging materials include bottles, glass bottles, food containers, lunch boxes, containers, freezer bags, packaging packs, packaging bags, packaging films, envelopes, and cardboard boxes.

[0181] Examples of daily necessities or miscellaneous goods include wet wipes or wet sheets, floor wipers, mops, trash cans, sanitary boxes, masks, bandages, adhesive bandages, toothbrushes, plastic bags, plastic gloves, plastic wrap, lunch box containers, drain nets, sink strainers, sponges, hoses, hangers, clothes pegs, shoes, sandals, slippers, rain gear (umbrellas, rainwear, etc.), outdoor equipment (tents, tarps, etc.), paper products, books, stationery, screen protectors, remote control covers, toys or hobby items (game consoles, puzzles, dolls, models, clay, balls, etc.).

[0182] (Antiviral coating agent) This disclosure includes an antiviral coating agent (also simply referred to as the coating agent) containing the antiviral agent; a method of coating an article or substrate with the antiviral coating agent to form an antiviral coating layer containing the active ingredient on the surface of the article or substrate; and an antiviral coating layer (also simply referred to as the coating layer) formed by the method described above.

[0183] The form of the coating agent is not particularly limited and may be liquid, solid, or semi-solid, but liquid is preferred. The coating agent may consist only of the antiviral agent, or it may further contain, in addition to the antiviral agent, a solvent or dispersion medium (for example, the solvent or dispersion medium exemplified as the liquid carrier), a binder component (for example, a polymer component described later), conventional additives used in coating agents or paints, etc.

[0184] Commonly used additives include, for example, fillers, dehydrating agents, wetting agents, stabilizers (antioxidants, ozone degradation inhibitors, UV absorbers, heat stabilizers, light stabilizers, etc.), plasticizers, softeners, lubricants, mold release agents, thickeners, antistatic agents, flame retardants, dispersants, surfactants, colorants, rust-inhibiting pigments, viscosity modifiers, preservatives, fungicides, antibacterial agents, coupling agents, defoamers, anti-settling agents, anti-skinning agents, polymerization inhibitors, leveling agents, thixotropic agents, color separation inhibitors, and matting agents. These additives can be used individually or in combination of two or more.

[0185] The coating agent may also be prepared by adding the antiviral agent to a conventional paint (for example, a water-based paint).

[0186] The proportion of the active ingredient in the coating agent may be appropriately selected depending on the manner of use, the type of article or substrate to which it is applied, and the period for which the antiviral effect is expected, and is, for example, about 0.001 to 100% by mass of the total coating agent.

[0187] The coating layer containing the active ingredient, which includes a fluorene compound, may be formed by coating an article or substrate with a coating agent. The coating method is not particularly limited as long as it can form a coating layer on the surface of the article or substrate. Examples include applying it to the surface of the article or substrate, spraying it onto the surface of the article or substrate, or immersing the article or substrate, and may be selected depending on the type of article or substrate and the type of coating agent. If necessary, the article or substrate may be pretreated (e.g., with a primer) before coating, and if necessary, a drying treatment may be performed after coating to form the coating layer.

[0188] The coating layer should contain at least an active ingredient including a fluorene compound. The proportion of the active ingredient in the coating layer may be appropriately selected depending on the mode of use, the type of article or substrate to which it is applied, and the period for which the antiviral effect is expected, and is, for example, 0.01 to 100% by mass of the entire coating layer, preferably in stages, 0.01 to 20% by mass, 0.01 to 10% by mass, and 0.01 to 5% by mass.

[0189] Furthermore, the coating layer (or active ingredient) may be fixed (adhered to or integrated) with the surface of the article or substrate, but it is not necessarily required to be fixed.

[0190] (Antiviral polymer composition) This disclosure includes an antiviral polymer composition (also simply referred to as a polymer composition) comprising the antiviral agent and a polymer component; an antiviral molded article (also simply referred to as a molded article) comprising this antiviral polymer composition; and a method of mixing the antiviral agent with the polymer component to impart antiviral properties to the polymer component.

[0191] In a polymer composition (and its molded article), the active ingredient containing the fluorene compound may be embedded or dispersed within the polymer component, and is preferably present on at least a portion of the surface of the polymer composition (and its molded article).

[0192] The polymer component is not particularly limited as long as it is a high-molecular-weight compound; for example, it may be a resin component or a rubber component. These polymer components may be used individually or in combination of two or more types.

[0193] The resin component may be a thermoplastic resin or a curable resin (thermo- or photocurable resin). These resin components can be used individually or in combination of two or more types.

[0194] Examples of thermoplastic resins include polyolefin resins such as chain olefin resins (polyethylene resins, polypropylene resins, etc.), cyclic olefin resins, and chlorinated polyolefin resins; styrene resins such as polystyrene, styrene-methyl methacrylate copolymer (MS resin), styrene-acrylonitrile copolymer (AS resin), high-impact polystyrene (HIPS), acrylonitrile-butadiene-styrene copolymer (ABS resin), and methyl methacrylate-butadiene-styrene copolymer (MBS resin); and polymethyl methacrylate (PMM). A) (meth)acrylic resins such as (meth)acrylic acid-(meth)acrylic acid ester copolymer; vinyl acetate resins such as polyvinyl acetate (PVAc), polyvinyl alcohol (PVA), polyvinyl acetal (polyvinyl formal (PVF), polyvinyl butyral (PVB), etc.); vinyl chloride homopolymer (PVC); vinyl chloride resins such as vinyl chloride-vinyl acetate copolymer; vinylidene chloride resins such as vinylidene chloride-vinyl chloride copolymer, vinylidene chloride-acrylonitrile copolymer; polytetrafluoroethylene (PTFE), etc. Fluororesins; Polyester resins such as polyalkylene arylate resins, polyarylate resins, liquid crystalline polyester (LCP), alkyd resins, and bisphenol-type (e.g., bisphenol A type) polycarbonate resins; Polyamide resins such as aliphatic polyamide resins, aromatic polyamide resins, or aramid resins; Polyacetal resins such as polyacetal resin (POM); Polyphenylene ether resins such as polyphenylene ether (PPE); Polyether ketone (PEK), polyether ether ketone (PEEK), polyether ketone Polyetherketone resins such as phenyletone ketone (PEKEKK); phenoxy resins; polyketone resins such as aliphatic polyketone resins; polyphenylene sulfide resins such as polyphenylene sulfide (PPS); polysulfone resins such as polysulfone (PSF) and polyethersulfone (PES); cellulose esters such as nitrocellulose, cellulose acetate, and cellulose acetate propionate; cellulose ethers such as ethylcellulose; thermoplastic polyimide resins such as polyetherimide (PEI) and polyamideimide;Examples include polyether nitrile resins; thermoplastic elastomers (TPEs) [e.g., polystyrene-based TPEs, polyolefin-based TPEs (TPOs), polydiene-based TPEs, chlorine-based TPEs, fluorine-based TPEs, polyurethane-based TPEs (TPUs), polyester-based TPEs (TPEEs), polyamide-based TPEs (TPAs), etc.]. These thermoplastic resins may be used individually or in combination of two or more types.

[0195] Examples of curable resins (thermal or photocurable resins) include phenolic resins; amino resins such as melamine resins, urea resins, and benzoguanamine resins; furan resins; silicone resins; epoxy resins such as bisphenol A type epoxy resins; unsaturated polyester resins; vinyl ester resins; polyurethane resins; and polyimide resins. These curable resins may be used individually or in combination of two or more types.

[0196] Examples of rubber components include diene rubber, olefin rubber, acrylic rubber (ACM, ANM), butyl rubber (IIR), epichlorohydrin rubber (CO), polysulfide rubber (OT, EOT), urethane rubber (U), silicone rubber (Q), fluororubber (FFKM, FKM), and sulfur-containing rubber. These rubbers may be used individually or in combination of two or more. Examples of the diene rubber include natural rubber (NR), epoxidized natural rubber, polybutadiene [e.g., butadiene rubber (BR), 1,2-polybutadiene (VBR), etc.], isoprene rubber (IR), chloroprene rubber (CR), acrylonitrile-butadiene rubber (NBR), and styrene-butadiene rubber (SBR). These diene rubbers may also be hydrogenated rubbers (e.g., hydrogenated BR, hydrogenated NBR, hydrogenated SBR, etc.). Examples of the aforementioned olefin-based rubbers include ethylene-propylene rubber (EPM), ethylene-propylene-diene rubber (EPDM), ethylene-butene rubber, ethylene-1-butene-diene rubber, propylene-1-butene-diene rubber, polyisobutylene rubber, isobutylene-isoprene rubber (IIR or butyl rubber), ethylene-vinyl acetate rubber, maleic acid-modified ethylene-propylene rubber (M-EPM), chlorosulfonated polyethylene (CSM), chlorinated polyethylene (CM), and maleic acid-modified chlorinated polyethylene (M-CM). Examples of diene units (non-conjugated diene units) that may be contained in olefin-based rubbers such as EPDM include dicyclopentadiene, 1,4-hexadiene, cyclooctadiene, methylenenorbornene, and units derived from ethylidenenorbornene.

[0197] The polymer composition (or its molded article) may contain at least an active ingredient comprising a fluorene compound. The proportion of the active ingredient in the polymer composition (or its molded article) may be appropriately selected depending on the mode of use or application, the period for which the antiviral effect is expected, etc., and is, for example, 0.01 to 100% by mass, preferably in stages, 0.01 to 20% by mass, 0.01 to 10% by mass, and 0.01 to 5% by mass, relative to the total amount of the active ingredient (particularly the fluorene compound) and polymer components.

[0198] The polymer composition may optionally contain conventional additives, such as fillers or reinforcing agents, colorants such as dyes and pigments, conductive agents, flame retardants, flame retardant aids, plasticizers, lubricants, stabilizers (antioxidants, UV absorbers, heat stabilizers, etc.), mold release agents, antistatic agents, dispersants, compatibilizers, flow regulators, leveling agents, defoamers, surface modifiers, stress reducers, carbon materials, etc. These additives may be used individually or in combination of two or more.

[0199] The proportion of the additive may be, for example, 50% by mass or less, 0 to 30% by mass, or 1 to 10% by mass relative to the polymer component.

[0200] The polymer composition can be prepared by mixing an antiviral agent (particularly a fluorene compound as an active ingredient), a polymer component, and other components such as additives as needed. For example, it may be prepared by mixing using conventional methods such as dry mixing or melt kneading (for example, the polymer composition may be in the form of pellets), or by impregnating the antiviral agent with the polymer component (for example, by impregnating it with fibers or fibrous structures as polymer components).

[0201] The molded article may contain at least the polymer composition, and its shape is not particularly limited and can be selected according to the application, etc. For example, it may be in the form of pellets, one-dimensional structures such as linear (fibrous or thread-like) or rod-like structures, two-dimensional structures such as film-like, sheet-like, or plate-like structures, three-dimensional structures such as block-like or hollow (tubular or tubular) structures, or composite or complex shapes that combine these shapes.

[0202] The molded article can be manufactured using conventional molding methods with the polymer composition, depending on the type of resin, the shape and application of the molded article, for example, injection molding, compression molding, transfer molding, lamination molding, FRP molding, casting, powder molding, extrusion molding, blow molding, lamination, casting, calendering, foam molding, 3D printing, etc.

[0203] Furthermore, the molded article may be a composite molded article comprising a polymer composition portion formed from a polymer composition and other constituent members. The proportion of the polymer composition (polymer composition portion) in the molded article is not particularly limited and may be, for example, 10 to 100% by mass or 20 to 80% by mass.

[0204] The molded article may be an industrial product or its raw material used in the various fields exemplified as the article or base material. [Examples]

[0205] The present disclosure will be described in more detail below based on examples, but the present disclosure is not limited to these examples. Various evaluation methods and raw materials used are also shown below.

[0206] [Evaluation Method] (5% weight loss temperature) Thermogravimetric analysis - Using a differential thermal analyzer (TG-DTA) (Rigaku Corporation "TG-DTA8122"), the temperature at which the mass of the sample decreased by 5% (5% weight loss temperature Td5) was measured under a nitrogen atmosphere and a heating rate of 10°C / min.

[0207] (Confirmation test of the effect of suppressing enveloped viruses) Antiviral Processing Agents: Evaluated according to the methods described below, in accordance with the Anti-Technical Standards Association's standards.

[0208] 10 8 TCID 50 Influenza virus (ATCC VR-1679) adjusted to / mL was used as the test virus suspension.

[0209] In a microtube containing a stirring bar, the fluorene compound [1 mg, 10 mg, 30 mg, or 50 mg], which is the test substance, and 0.05 mL of dimethyl sulfoxide (DMSO) were added. Further, 0.85 mL of sterile water and 0.1 mL of the test virus suspension were mixed and stirred for 24 hours to prepare the mixed solutions (test samples) listed in Table 1 below, with test substance concentrations of 0.1 w / v%, 1 w / v%, 3 w / v%, or 5 w / v%.

[0210] [Table 1]

[0211] 50 μL of the obtained test sample solution was mixed with 450 μL of a drug inactivator (SCDLP liquid medium, Eiken Chemical Co., Ltd.) to inactivate the drug. This inactivated mixture was then used to create 10-fold serial dilutions using a dilution medium (E-MEM, Fujifilm Wako Pure Chemical Industries, Ltd.) and used in TCID with host cells (MDCK cells, ATCC CCL-34). 50 The viral infectivity titer was measured using the median tissue culture infectious dose method.

[0212] On the other hand, the viral infectivity titer was measured for the control test samples listed in Table 1, in the same manner as above except that fluorene compounds were not added. Based on the viral infectivity titer, the antiviral activity value (or viral suppression activity value) (Mv) was calculated using the following formula.

[0213] Antiviral activity value (Mv) = Ig(Vb) - Ig(Vc)

[0214] [In the formula, Ig(Vb) is the viral infectivity titer of the control test sample solution listed in Table 1 [TCID] 50 The logarithmic value of [TCID / mL] is shown, and Ig(Vc) represents the viral infectivity titer of each test sample solution at the test sample concentrations listed in Table 1. 50 This shows the common logarithm of [ / mL].

[0215] A value of approximately "1" or higher for antiviral activity (Mv) was considered to indicate an effect in suppressing enveloped viruses, and a value of approximately "2" or higher was considered to indicate a more practical effect in suppressing enveloped viruses.

[0216] (Confirmation test of non-enveloped virus suppression effect) Antiviral Technology Association Method: The evaluation was performed according to the method described below, in accordance with the standards for antiviral processing agents. Specifically, the influenza virus in the test virus suspension was replaced with feline calicivirus (ATCC VR-782), the E-MEM in the dilution medium was replaced with RPMI-1640 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and the MDCK host cells were replaced with CRFK cells (ATCC CCL-94). The virus suppression effect confirmation test was then conducted in the same manner as the "Confirmation Test for Enveloped Virus Suppression Effect" described above. Based on the measured viral infectivity titer, the antiviral activity value (Mv) was calculated using the above calculation formula.

[0217] A non-enveloped virus inhibitory effect was determined when the antiviral activity value (Mv) was approximately "1" or higher, and a non-enveloped virus inhibitory effect was determined when it was approximately "2" or higher.

[0218] [Fluorene compounds] BCF:9,9-Bis(4-hydroxy-3-methylphenyl)fluorene BOPPF: 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene BNF:9,9-Bis(6-hydroxy-2-naphthyl)fluorene BPEF:9,9-Bis[4-(2-hydroxyethoxy)phenyl]fluorene BNEF:9,9-Bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene BAF:9,9-bis(4-aminophenyl)fluorene DNFDP-m:9,9-bis[2-(methoxycarbonyl)ethyl]-2,7-di(2-naphthyl)fluorene AAD-FL:9,9-Bis[2-(carbamoyl)ethyl]fluorene 9-Fluorenone 9H-Fluorine The chemical structures of each fluorene compound are shown below.

[0219] [ka]

[0220] The 5% weight loss temperature and antiviral activity values ​​(Mv) against enveloped and non-enveloped viruses for each fluorene compound are summarized in Tables 2 and 3 below.

[0221] [Table 2]

[0222] [Table 3]

[0223] As is clear from the results in Tables 2-3, all of the fluorene compounds in the examples not only exhibited high heat resistance, but also showed excellent antiviral activity against enveloped and non-enveloped viruses even at low concentrations of about 0.1-1 w / v%. Among these examples, BCF (Example 1), BOPPF (Example 2), BNF (Example 3), BNEF (Example 5), BAF (Example 6), DNFDP-m (Example 7), and 9-fluorenone (Example 9) [preferably BCF (Example 1), BOPPF (Example 2), BNF (Example 3), and BAF (Example 6); more preferably BOPPF (Example 2) and BNF (Example 3)] showed relatively high antiviral activity even at a low concentration of 0.1 w / v%. [Industrial applicability]

[0224] The antiviral agent disclosed herein is useful as it exhibits excellent antiviral properties. For example, it can impart excellent antiviral properties to various industrial products and materials.

Claims

1. An antiviral agent containing a fluorene compound having a fluorene skeleton as an active ingredient.

2. The antiviral agent according to claim 1, wherein the fluorene compound comprises at least one selected from a compound having a 9,9-bisarylfluorene skeleton, a compound having a 9,9-bisalkylfluorene skeleton, a compound having a 9-fluorenone skeleton, and a compound having a 9H-fluorene skeleton.

3. The antiviral agent according to claim 1, wherein the fluorene compound comprises at least one selected from compounds having a 9,9-bisarylfluorene skeleton and compounds having a 9,9-bisalkylfluorene skeleton.

4. The antiviral agent according to claim 1, wherein the fluorene compound comprises at least one selected from a compound having a 9,9-bisarylfluorene skeleton represented by the following formula (1) and a compound having a 9,9-bisalkylfluorene skeleton represented by the following formula (2). 【Chemistry 1】 (In the formula, R １ represents a substituent, and m1 represents an integer from 0 to 8. Z １ａ and Z １ｂ These independently show an arene ring, X １ａ and X １ｂ p1a and p1b independently represent a heteroatom-containing functional group, and p1a and p1b independently represent an integer of 1 or more. R ３ａ and R ３ｂ (where m3a and m3b independently represent substituents, and m3a and m3b independently represent integers greater than or equal to 0.) 【Chemistry 2】 (In the formula, R ４ represents a substituent, and m4 represents an integer from 0 to 8. A ２ａ and A ２ｂ each independently represents an alkylene group which may have a substituent, X ２ａ and X ２ｂ (These independently represent heteroatom-containing functional groups.)

5. In the above formula (1), R １ represents a hydrocarbon group, and m1 represents an integer from 0 to 4. Z １ａ and Z １ｂ C is independent ６－１８ Showing an arene ring, X １ａ and X １ｂ The base [-O-(A １ O) ｎ１ -H] (wherein, A １ represents an alkylene group, and n1 represents an integer greater than or equal to 0. ), group [-C(=O)-R ２ ] [wherein, R ２ is a hydroxyl group, group [-OR ｈ ] (wherein, R ｈ represents a hydrocarbon group. ), represents a halogen atom, an amino group, or a substituted amino group. ] represents an amino group or a substituted amino group, and p1a and p1b independently represent integers from 1 to 2. R ３ａ and R ３ｂ m3a and m3b independently represent an integer from 0 to 4; In the above formula (2), R ４ represents a hydrocarbon group, and m4 represents an integer from 0 to 4. A ２ａ and A ２ｂ This independently represents an alkylene group which may have a hydrocarbon group, X ２ａ and X ２ｂ The base [-O-(A ３ O) ｎ３ -H] (wherein, A ３ represents an alkylene group, and n3 represents an integer greater than or equal to 0. ), group [-C(=O)-R ５ ] [wherein, R ５ is a hydroxyl group, group [-OR ｈ ] (wherein, R ｈ The antiviral agent according to claim 4, wherein the group represents a hydrocarbon group, a halogen atom, an amino group, or a substituted amino group.

6. The antiviral agent according to any one of claims 1 to 5, wherein the fluorene compound includes a compound having a symmetrical chemical structure with respect to the 9-position of the fluorene skeleton.

7. The antiviral agent according to any one of claims 1 to 5, wherein the molecular weight of the fluorene compound is 3000 or less.

8. The antiviral agent according to any one of claims 1 to 5, wherein the 5% weight loss temperature of the fluorene compound is 250°C or higher.

9. An antiviral agent according to any one of claims 1 to 5, which is an antiviral agent against enveloped viruses or non-enveloped viruses.

10. An antiviral coating agent comprising the antiviral agent described in any one of claims 1 to 5.

11. A method for forming an antiviral coating layer containing the active ingredient on the surface of an article or substrate by coating it with the antiviral coating agent described in claim 10.

12. The antiviral coating layer according to claim 11.

13. An antiviral polymer composition comprising an antiviral agent according to any one of claims 1 to 5 and a polymer component.

14. An antiviral molded article comprising the antiviral polymer composition described in claim 13.

15. A method for imparting antiviral properties to a polymer component by mixing an antiviral agent according to any one of claims 1 to 5 with the polymer component.

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