阅读说明：本技术 抗病毒用擦拭布 (Wiping cloth for anti-virus ) 是由 原美代子 于 2019-08-28 设计创作，主要内容包括：本发明的课题在于提供一种抗病毒活性优异且保存稳定性优异的抗病毒用擦拭布。本发明的抗病毒用擦拭布为具有基布及浸渗于上述基布的溶液剂的抗病毒用擦拭布,上述基布中的纤维素类纤维的含量相对于构成上述基布的纤维的总质量为70质量％以下,上述溶液剂为碱性,且包含pKa为7.0～15.0的化合物X及至少包括醇的溶剂,上述醇的含量相对于上述溶剂的总质量为40～100质量％。(The invention provides a wiping cloth for antivirus, which has excellent antivirus activity and excellent storage stability. The wiping cloth for resisting virus of the invention is a wiping cloth for resisting virus comprising a base cloth and a solution agent which is impregnated in the base cloth, wherein the content of cellulose fiber in the base cloth is less than 70 mass percent relative to the total mass of the fiber forming the base cloth, the solution agent is alkaline, and comprises a compound X with pKa of 7.0-15.0 and a solvent at least comprising alcohol, and the content of the alcohol is 40-100 mass percent relative to the total mass of the solvent.)

1. An anti-virus wiping cloth, which comprises a base cloth and a solution agent impregnated in the base cloth,

the content of cellulose-based fibers in the base fabric is 70 mass% or less with respect to the total mass of the fibers constituting the base fabric,

the solution is alkaline, and comprises a compound X with a pKa of 7.0-15.0 and a solvent at least comprising alcohol, wherein the content of the alcohol is 40-100% by mass relative to the total mass of the solvent.

2. The anti-viral wipe according to claim 1,

the compound X is a compound having a phenolic hydroxyl group.

3. The anti-viral wipe according to claim 1 or 2,

the content of the cellulose-based fiber is 30 mass% or less with respect to the total mass of the fiber.

4. The anti-virus wipe according to any one of claims 1 to 3,

the base fabric contains substantially no cellulose-based fibers.

5. The anti-virus wipe according to any one of claims 1 to 4,

the base fabric includes one or more synthetic fibers selected from the group consisting of polyolefin fibers, polyester fibers, vinylon fibers, and nylon fibers.

6. The anti-virus wipe according to any one of claims 1 to 5,

the fibers constituting the base fabric are synthetic fibers selected from the group consisting of polyolefin fibers, polyester fibers, and vinylon fibers.

7. The anti-virus wipe according to any one of claims 1 to 6,

the fibers constituting the base fabric are synthetic fibers selected from the group consisting of polyolefin fibers and polyester fibers.

8. The anti-virus wipe according to any one of claims 5 to 7,

the content of the synthetic fibers is 95 mass% or more with respect to the total mass of the fibers.

9. The anti-virus wipe according to any one of claims 1 to 8,

the alcohol includes an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms.

10. The anti-viral wipe according to claim 9,

the alcohol having 2or less carbon atoms includes ethanol, and the alcohol having 3or more carbon atoms includes isopropanol.

11. The anti-virus wipe according to any one of claims 1 to 10,

the solution also comprises a surfactant.

12. The anti-virus wipe according to any one of claims 1 to 11,

the solution also comprises a chelating agent.

Technical Field

The invention relates to an anti-virus wiping cloth.

Background

Norovirus is classified into the genus norovirus of the family caliciviridae, and is known as a pathogen causing food poisoning and the like. Recently, for the purpose of preventing infection with norwalk virus, there has been a demand for the development of wiping cloths in which a base cloth such as a nonwoven fabric is impregnated with a solution having an anti-norwalk virus activity.

For example, patent document 1 describes a norwalk virus-killing solution containing procyanidins (compounds having a phenolic hydroxyl group).

Patent document 1: japanese patent laid-open publication No. 2013-047196

The present inventors have prepared an antiviral solution containing a compound having a phenolic hydroxyl group with reference to patent document 1, and have made studies to produce a wipe cloth in which a base cloth (for example, nonwoven fabric) is impregnated with the solution, and as a result, they have found that antiviral activity may deteriorate after long-term storage depending on the material of the base cloth. In other words, it was found that there is still room for improvement in the storage stability of the anti-virus wiper.

On the other hand, there is a continuing need to further improve the antiviral activity of antiviral wipes.

Accordingly, an object of the present invention is to provide an antiviral wipe having excellent antiviral activity and excellent storage stability.

Disclosure of Invention

The present inventors have conducted extensive studies to solve the above problems, and as a result, have found that the above problems can be solved by adjusting the content of cellulose fibers in a base fabric, and have completed the present invention.

That is, the following configuration was found to solve the above problems.

[ 1] an anti-virus wiping cloth comprising a base cloth and a solution impregnated into the base cloth, wherein the anti-virus wiping cloth,

the content of the cellulose-based fibers in the base fabric is 70% by mass or less based on the total mass of the fibers constituting the base fabric,

the solution is alkaline, and contains a compound X having a pKa of 7.0 to 15.0 and a solvent containing at least an alcohol, and the content of the alcohol is 40 to 100% by mass relative to the total mass of the solvent.

[ 2] the anti-viral wipe according to [ 1], wherein the compound X is a compound having a phenolic hydroxyl group.

[ 3] the anti-viral wiping cloth according to [ 1] or [ 2], wherein the content of the cellulosic fiber is 30% by mass or less with respect to the total mass of the fiber.

[ 4] the anti-virus wiping cloth according to any one of [ 1] to [ 3], wherein the base cloth does not substantially contain the cellulose-based fiber.

[ 5] the anti-virus wiping cloth according to any one of [ 1] to [ 4], wherein the base cloth contains one or more synthetic fibers selected from the group consisting of polyolefin fibers, polyester fibers, vinylon fibers, and nylon fibers.

[ 6] the anti-virus wiping cloth according to any one of [ 1] to [ 5], wherein the fibers constituting the base cloth are synthetic fibers selected from the group consisting of polyolefin fibers, polyester fibers and vinylon fibers.

[ 7] the anti-virus wiping cloth according to any one of [ 1] to [ 6], wherein the fibers constituting the base cloth are synthetic fibers selected from the group consisting of polyolefin fibers and polyester fibers.

[ 8] the anti-virus wiping cloth according to any one of [ 5] to [ 7], wherein a content of the synthetic fiber is 95% by mass or more with respect to a total mass of the fiber.

[ 9] the antiviral wiping cloth according to any one of [ 1] to [ 8], wherein the alcohol includes an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms.

The antiviral wiping cloth according to [ 9], wherein the alcohol having 2or less carbon atoms includes ethanol, and the alcohol having 3or more carbon atoms includes isopropyl alcohol.

The antiviral wipe according to any one of [ 1] to [ 10], wherein the solution further contains a surfactant.

[ 12] the antiviral wipe according to any one of [ 1] to [ 11], wherein the solution further contains a chelating agent.

Effects of the invention

According to the present invention, an antiviral wipe having excellent antiviral activity and excellent storage stability can be provided.

Detailed Description

The present invention will be described in detail below.

The following description of the configuration conditions is made in accordance with a representative embodiment of the present invention, but the present invention is not limited to such an embodiment.

In the present specification, a numerical range represented by "to" means a range in which numerical values described before and after "to" are included as a lower limit value and an upper limit value.

In the present specification, when a plurality of substituents, linkers, and the like (hereinafter, referred to as "substituents" and the like) represented by specific symbols are present, or when a plurality of substituents and the like are simultaneously defined, the substituents and the like may be the same or different from each other. The same applies to the number of substituents and the like.

Further, in the present specification, in the notation of the group (atomic group), the notation that substitution and non-substitution are not marked means that not only a group having no substituent but also a group having a substituent is included. For example, "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).

[ wiping cloth for anti-virus ]

The anti-virus wiping cloth (hereinafter, also referred to as "wiping cloth") of the present invention has

A base cloth and an anti-virus wiping cloth impregnated with the solution,

the content of the cellulose-based fibers in the base fabric is 70% by mass or less based on the total mass of the fibers constituting the base fabric,

the solution is alkaline, and contains a compound X having a pKa of 7.0 to 15.0 and a solvent containing at least an alcohol, and the content of the alcohol is 40 to 100% by mass relative to the total mass of the solvent.

The wipe is excellent in antiviral activity (particularly antiviral activity against feline calicivirus (closely related species of norwalk virus)) due to the presence of the compound X having a pKa of 7.0 to 15.0. Further, the wiper is less likely to cause deterioration in antiviral activity after long-term storage (in other words, has excellent storage stability).

In addition, it has been confirmed that the wiping sheet is excellent in antibacterial activity against other viruses and microorganisms such as bacteria and fungi (for example, adenovirus, influenza virus, herpes virus, trichophyton, candida, aspergillus, escherichia coli, staphylococcus, and the like).

The mechanism of action of the present invention is not specifically defined, but the present inventors speculate as follows.

In the solution, a compound X having a pKa of 7.0 to 15.0 functions as an active ingredient (antiviral ingredient). It is presumed that, when the liquid solution is alkaline, anions formed by dissociation of hydrogen ions from the compound X (hereinafter, also referred to as "anions derived from the compound X". for example, when the compound X is a compound having a phenolic hydroxyl group, phenoxy anions are generated by dissociation of hydrogen ions) deprotonate acid groups present on the surface of the virus, and the virus is inactivated. The present inventors also considered that alcohol contained in a predetermined amount in the solvent is one of the main factors for making the solution agent excellent in antiviral activity (and further antiviral activity of the wipe).

The present inventors have now found that the anti-viral activity of a wiping cloth formed by using a base cloth containing a large amount of cellulose fibers is remarkably reduced after long-term storage. The reason for this is considered to be that the hydroxyl groups in the cellulose fibers adsorb anions derived from the compound X due to hydrogen bonding interaction, and the pH of the solution agent changes due to substitution of a pH adjuster (for example, an alkali such as sodium hydroxide) that can be contained in the solution agent with hydrogen atoms in the hydroxyl groups in the cellulose fibers, thereby relatively reducing the amount of anions derived from the compound X that are produced in the solution agent.

In contrast, the present inventors have found that when the content of the cellulose-based fibers in the base fabric is 70 mass% or less with respect to the total mass of the fibers, the decrease in antiviral activity can be suppressed even after long-term storage.

First, the prescription of the solution contained in the wiping cloth will be described below.

[ solution ]

< Compound X >

The above solution contains compound X.

The compound X has a pKa of 7.0 to 15.0 and is dissociated into hydrogen ions under alkaline conditions to be in an anionic state. When the compound X has a plurality of pKa (that is, when the compound X is an acid accompanied by multi-stage dissociation), at least one of the plurality of pKa may satisfy 7.0 to 15.0.

The pKa of the compound X is preferably 7.0 to 12.0.

Examples of the compound X include compounds having a phenolic hydroxyl group, a mercapto group, or an amino group as a functional group, and among them, compounds having a phenolic hydroxyl group are preferable in terms of their excellent stability in an anionic state and safety of materials.

When the compound X is a compound having a phenolic hydroxyl group, a mercapto group, or an amine group as a functional group, the pKa of the phenolic hydroxyl group, the mercapto group, or the amine group preferably satisfies 7.0 to 15.0.

When the compound X is a compound having a phenolic hydroxyl group, a mercapto group, or an amine group as a functional group, the number of the above functional groups in the compound X is not particularly limited, and may be one or more.

The "pKa value" in the present specification is a "pKa value" calculated using software (Chem Bio Draw Ultra var.12.0.(cambridge soft Corporation, USA)).

The content of the compound X (particularly, a compound having a phenolic hydroxyl group) in the solution is not particularly limited, but is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, and further preferably 0.2% by mass or more, based on the total mass of the solution, in order that the anti-viral activity of the wipe is more excellent. The upper limit is not particularly limited, but is preferably 5.0% by mass or less, more preferably 1.0% by mass or less, and further preferably 0.5% by mass or less.

One compound X (particularly, a compound having a phenolic hydroxyl group) may be used alone, or two or more compounds may be used in combination. When two or more compounds X (particularly, compounds having a phenolic hydroxyl group) are used in combination, the total content is preferably within the above range.

Specific examples of the compound X are described in detail below.

Compound having phenolic hydroxyl group

The compound having a phenolic hydroxyl group may have one phenolic hydroxyl group in one molecule, or may have two or more phenolic hydroxyl groups in one molecule.

In the present specification, the phenolic hydroxyl group means a hydroxyl group substituted for a hydrogen atom of an aromatic ring, preferably a hydroxyl group substituted for a hydrogen atom of a benzene ring.

In the present specification, among compounds having a phenolic hydroxyl group, a compound having one hydroxyl group substituted for a hydrogen atom of an aromatic ring is referred to as a "monophenol compound", and a compound having two or more hydroxyl groups substituted for a hydrogen atom of an aromatic ring is referred to as a "polyphenol compound". Examples of the monophenol compound include a compound E described later, a compound represented by the formula (1H), and a compound represented by the compound (2 Ai). Examples of the polyphenol compound include compounds a to D, compound F, and compound G described below.

Examples of the compound having a phenolic hydroxyl group include the following compounds a to D.

(Compound A)

The compound a is a compound having two or more residues (hereinafter also referred to as "residues of formula (1A)") of the compound represented by formula (1A) below, from which one or more hydrogen atoms other than hydrogen atoms in hydroxyl groups have been removed.

In the compound a, a plurality of the residues of formula (1A) may be directly bonded to each other, and a plurality of the residues of formula (1A) may be bonded via a linking group.

The two or more residues of formula (1A) in compound a may be the same as or different from each other.

The molecular weight of the compound A is not particularly limited, but is preferably 218 to 2000, more preferably 218 to 1500.

The number of residues of formula (1A) in compound A is preferably 2 to 10, more preferably 1 to 6.

In addition, compound a may be a polymer.

The polymer, compound a, preferably has a repeat unit comprising a residue of formula (1A).

The weight average molecular weight of the polymer, i.e., the compound A, is, for example, preferably 1000 to 100 ten thousand, and more preferably 5000 to 100 ten thousand.

In the present specification, when the specific compound is a polymer, the weight average molecular weight (Mw) is defined as a polystyrene equivalent value by GPC (Gel Permeation Chromatography).

[ chemical formula 1]

In the formula (1A), X¹¹～X¹⁴Each independently represents a nitrogen atom or-CR¹¹＝。R¹¹Represents a hydrogen atom or a substituent.

X¹¹～X¹⁴Is preferably-CR¹¹＝。

X¹¹～X¹⁴At least one preferably represents R¹¹Is a hydrogen atom or a group having a hydrogen atom, i.e. -CR¹¹＝。

When there are more than one-CR¹¹When not, a plurality of R¹¹May be the same as or different from each other.

As by R¹¹Specific examples of the substituent include a hydroxyl group, an alkyl group, an aryl group, a heterocyclic group (e.g., a non-aromatic heterocyclic ring, an aromatic heterocyclic ring, etc.), a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), a nitro group, a sulfo group, a phosphoric acid group, a cyano group, a nitro group, an amino group, an alkali metal oxy group (e.g., a sodium oxy group, a potassium oxy group, etc.), a sulfonic acid base (e.g., a sodium sulfonate group), a glycosyl group, a group having an ethenylene group (— C ═ C-), a group having an ethynylene group (— C ≡ C-), a group having an ether group (≡ O-), a group having an imino group (═ C ═ N-), a group having an ester group (— CO — O-) and ≡ O — CO-), and a group, Having a carbonyl group (═ CO-), having a phosphine oxide group (═ P (═ O) (+ -)₂) Having a phosphonate group (═ O) (-O-)₂) Having a phosphate group (═ O) (-O-)₂) A group having a sulfinyl group (═ O) -), a sulfonyl group (═ S) (═ O)₂-) group, group having amide group (-CO-NH-) and-NH-CO-), group having sulfonamide group (-SO-)₂-NH-and-NH-SO₂-) radical, radical having an azo group (. -N ═ N-), radical having a trialkoxysilyl group (. -Si (OR)^S1 ₃) Group having an ammonium group (. -N)⁺(-*)₃) Having a sulfonium group (— S)⁺(-*)₂) Having a phosphonium group (. -P)⁺(-*)₃) Having an oxonium radical (. -O)⁺(-*)₂) A group having a normal carbon group (— C)⁺(-*)₂) Having a halonium group (. -X)⁺-; x is a halogen atom) and a group in which they are combinedA group.

The foregoing indicates bonding sites.

In the above examples, R^S1Represents an alkyl group. When there are more than one R in a group^S1When a plurality of R^S1May be the same as or different from each other.

And, where possible, the substituent may also have a substituent.

The alkyl group may be linear, branched, or have a cyclic structure. The number of carbon atoms is preferably 1 to 20.

The number of carbon atoms of the aryl group is preferably 6 to 15, more preferably 6.

R¹¹For example, hydrogen atom or Hammett substituent constant σ is preferable_pA substituent greater than 0.

Hammett substituent constant sigma_pReference can be made to chem.rev.1991, 91, p 165-195.

In addition, the Hammett substituent constant σ_pSubstituents greater than 0 are, for example, preferably-CH ═ CH-CO-O-CH₂CH₃(σ_p0.03), to which has been further bonded a hammett substituent constant σ via a conjugated group such as an ethenylene group, an ethynylene group, an imino group, an azo group, an aryl group, or a heteroaryl group_pSubstituents greater than 0.

Wherein R is¹¹Preferably selected from allyloxy, arylazo, heteroarylazo, halogen atom, nitro, sulfo, alkanesulfonyl, arylsulfonyl, alkanesulfonyloxy, arylsulfonyloxy, cyano, nitro, alkynyl, perfluoroalkoxy, perfluoroalkyl, -CO-R^T1、-CO-O-R^T1、-O-CO-R^T1、-NH-CO-R^T1、-CO-NH-R^T1、-SO₂-NH-R^T1、-NH-SO₂-R^T1、-C(＝NR^T1)R^T2、-CH＝CH-R^T1and-P (═ O) R^T1R^T2Any one of the substituent groups T in the group or a hydrogen atom.

In the substituent group T, R^T1And R^T2Each independently represents a hydrogen atom or a substituent (for example, has an alkyl group (which may be a straight chain)The branched structure may have a cyclic structure. Carbon number is preferably 1 to 20)) or an ester group (for example, an alkyl group which may have an-ester-substituent. The substituent of the alkyl group is preferably a hydroxyl group and/or a carboxyl group), etc.).

In addition, R^T1And R^T2May be bonded to each other to form a ring.

The compound represented by the formula (1A) preferably has at least one R¹¹is-CR of any of substituent groups T¹¹＝。

Further, the compound A preferably has at least one R having any one of the substituent groups T¹¹More preferably, the residue of formula (1A) has two or more. More preferably, all of the residues of formula (1A) in compound A are R having any one of the substituent groups T¹¹The residue of the compound represented by the formula (1A).

In the formula (1A), when there is-CR¹¹Is equal to X¹¹～X¹⁴When a plurality of R¹¹May be the same or different from each other, and a plurality of R' s¹¹Each other (e.g., when X¹¹And X¹²is-CR¹¹Adjacent when R is ═ o¹¹Each other, X¹²And X¹³is-CR¹¹Adjacent when R is ═ o¹¹Each other, X¹³And X¹⁴is-CR¹¹Adjacent when R is ═ o¹¹Each other) may be bonded to each other to form a ring.

Plural R¹¹The rings formed by bonding to each other may be aromatic rings (for example, aromatic hydrocarbon rings and aromatic heterocyclic rings) or non-aromatic rings (for example, non-aromatic hydrocarbon rings and non-aromatic heterocyclic rings).

Further, a fused ring structure in which rings are fused may be further formed in the formed rings.

The formed ring is preferably a 5-membered ring or a 6-membered ring, or a combined polycyclic ring, and when each ring is a heterocyclic ring, the number of heteroatoms is preferably 1 to 5.

Examples of the hetero atom of the heterocyclic ring include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom. Among them, a nitrogen atom, a sulfur atom or an oxygen atom is preferable.

Examples of the ring to be formed include a benzene ring, a naphthalene ring, a chroman ring, a quinoline ring, a quinoxaline ring, an anthraquinone ring, a 3-cyclobutene-1, 2-dione ring, a dihydrofuran ring, a crotonolactone ring, a 4-cyclopenten-1, 2, 3-trione ring, a 2,4, 6-cycloheptatrien-1-one ring and a benzoquinone ring.

Such a ring may further have a substituent (a residue obtained by removing one hydrogen atom from a hydroxyl group of an alkyl group, a hydroxyl group, a cyano group, a carboxyl group, a sulfonic acid base, an alkyl ester alkylene group, and a saccharide (e.g., a disaccharide such as rutinose), etc., and these groups may further have a substituent, where possible).

Further, it is preferable that X is X in the case where the compound A has a residue (residue of formula (1A)) of the compound represented by formula (1A) from which one or more hydrogen atoms other than hydrogen atoms in hydroxyl groups have been removed¹¹～X¹⁴Has R with hydrogen atoms removed¹¹Of (a) to (CR)¹¹Is as follows. I.e. X¹¹～X¹⁴At least one of (A) preferably represents R¹¹Is a hydrogen atom or a group having a hydrogen atom¹¹＝。

R¹¹The position where the removed hydrogen atom exists in (2) is a bonding position of the residue of formula (1A) with another group. In addition, when removing R of hydrogen atom¹¹When it is a hydrogen atom, R¹¹Which itself is removed.

R with hydrogen atoms removed¹¹Preferably any one of the groups having a hydrogen atom in the substituent group T or a hydrogen atom, and more preferably-CO-O-R^T1or-O-CO-R^T1(wherein, at this time, R^T1Is a hydrogen atom or a substituent having a hydrogen atom).

As the residue of formula (1A), a group represented by the following formula (1-2A) is preferred.

[ chemical formula 2]

In the formula (1-2A), R^1-2Represents a hydrogen atom, a hydroxyl group or an alkoxy group (which may be linear)The branched structure may have a cyclic structure. The number of carbon atoms is preferably 10 to 20).

m^1-2Represents an integer of 1 to 3, preferably 1.

Denotes the bonding site.

The compound a is preferably a compound represented by the following formula (1-3A).

[ chemical formula 3]

In the formula (1-3A), R^1-2aAnd R^1-2bAnd R in the formula (1-2A)^1-2The meaning is the same. R^1-2aAnd R^1-2bMay be the same as or different from each other.

L^1-2aAnd L^1-2bEach independently represents a single bond or a 2-valent linking group. Examples of the 2-valent linking group include an ether group, a carbonyl group, an ester group, a thioester group, an amide group, a sulfonamide group, a thioether group and-SO₂-、-NR^A-(R^ARepresents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group. ) 2-valent hydrocarbon groups (e.g., alkylene, alkenylene, alkynylene, and arylene), heteroarylene groups, azo groups, and combinations thereof.

L^1-2aAnd L^1-2bEach independently preferably a single bond, an ester group, a vinylene group, or a combination thereof (e.g., -vinylene-ester-).

l^1-3Represents 0 or 1.

m^1-3Represents an integer of 2or more. m is^1-3For example, the amount is preferably 2 to 10, more preferably 2 to 6.

When m is^1-3When is 2, X^1-3Represents a single bond or a 2-valent linking group, when m^1-3When greater than 2, m is^1-3A valence linking group.

In the formula (1-3A), X^1-3A plurality of other groups are present, and the groups represented by the same reference numerals may be the same or different.

Wherein, when m^1-3When is 2, X^1-3Preferably a single bond or a 2-valent linking group represented by the following formula. In the formula, Rx²Represents a hydrogen atom, a halogen atom or an alkyl group (which may be linear, branched or have a cyclic structure). the number of carbon atoms is preferably 1 to 20. Ar represents an arylene group (preferably having 1 to 20 carbon atoms, more preferably a phenylene group, a naphthylene group or an anthracenylene group, and still more preferably an anthracenylene group). Is represented by^1-2aOr L^1-2bThe bonding position of (2).

[ chemical formula 4]

When m is^1-3When is 3, X^1-3Any of the 3-valent linking groups represented by the following formulae is preferred. In the formula, Rx³Represents a hydrogen atom, a halogen atom or an alkyl group (which may be linear, branched or have a cyclic structure). the number of carbon atoms is preferably 1 to 20, more preferably a methyl group). Is represented by^1-2aOr L^1-2bThe bonding position of (2).

[ chemical formula 5]

When m is^1-3When is 4, X^1-3A4-valent linking group represented by the following formula is preferred. Is represented by^1-2aOr L^1-2bThe bonding position of (2).

[ chemical formula 6]

When m is^1-3When is 5, X^1-3A5-valent linking group represented by the following formula is preferred. Is represented by^1-2aOr L^1-2bThe bonding position of (2).

[ chemical formula 7]

When m is^1-3When is 6, X^1-3A6-valent linking group represented by the following formula is preferred. Is represented by^1-2aOr L^1-2bThe bonding position of (2).

[ chemical formula 8]

When compound a is a polymer and has a repeating unit comprising a residue of formula (1A), compound a preferably has a repeating unit represented by the following formula.

The polymer may have a repeating unit other than the repeating unit represented by the following formula.

[ chemical formula 9]

In the formula, Rx^maRepresents a hydrogen atom, a halogen atom, an alkyl group (which may be linear, branched or have a cyclic structure) having preferably 1 to 20 carbon atoms, more preferably a methyl group, or a perfluoroalkyl group (which may be linear, branched or have a cyclic structure having preferably 1 to 20 carbon atoms, more preferably a trifluoromethyl group).

Lx represents a single bond or a 2-valent linking group. Definition of 2-valent linking group with L^1-2The definition of the 2-valent linking group is the same.

X represents a residue of formula (1A).

(Compound B)

The compound B is represented by the following formula (2B).

The compound B is a compound other than the compound a.

Specifically, compound B does not include forms having two or more residues of formula (1A).

The molecular weight of the compound B is preferably 110 to 2000, and more preferably 120 to 1500.

[ chemical formula 10]

In the formula (2B), X²¹～X²⁴Each independently represents a nitrogen atom or-CR²¹＝。

X²¹～X²⁴Is preferably-CR²¹＝。

-CR²¹R in ═ C²¹Represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group or a group represented by the formula (5B).

When there are more than one-CR²¹When not, a plurality of R²¹May be the same as or different from each other.

*-L²-R^2x (5B)

In the formula (5B), L²Represents an arylene group which may have a substituent, a heteroarylene group which may have a substituent, or a 2-valent linking group represented by any one of the following formulae (6B) to (9B). R^2xRepresents a hydrogen atom or a substituent. Denotes the bonding site. When a plurality of groups represented by the formula (5B) are present, the plurality of groups represented by the formula (5B) may be the same as or different from each other.

[ chemical formula 11]

In the formulae (6B) to (9B), R^2a～R^2dEach independently represents a hydrogen atom or a substituent. 1 is the same as in formula (5B). 2 denotes with R^2xThe bonding position of (2).

In the formula (9B), Q represents-CO-, -S (═ O)₂-、-O-、-S-、-SiR^2eR^2f-、-NR^2g-、-N＝CR^2h-、-CR²ⁱN-, -N-or-P (═ O) R^2l-。R^2e～R^2lEach independently represents a hydrogen atom or a substituent.

As by R^2xAnd R^2a～R^2jThe substituent represented by (1) includes the above-mentioned substituent represented by R¹¹The substituents are as exemplified in the description of the substituents.

Wherein, as R^2xAnd R^2a～R^2jExamples thereof include a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a carboxyl group, a nitro group, an alkyl group, an alkoxy group, an alkylamino group, an aryl group, an arylamido group, a nitroarylene group, an alkyl ester group, an aminoalkylene group, an alkylaminoalkylene group, an alkali metal oxy group (-ONa, OK, etc.), and a combination thereof (for example, an alkyl ester group having a hydroxyl group and a carboxyl group in the alkyl moiety).

The group represented by the formula (5B) may be linked to each other by a substituent in the group to form a ring.

The ring to be formed may be an aromatic ring (for example, an aromatic hydrocarbon ring or an aromatic heterocyclic ring) or a non-aromatic ring (for example, a non-aromatic hydrocarbon ring or a non-aromatic heterocyclic ring).

Further, a fused ring structure in which rings are fused may be further formed in the formed rings.

The formed ring is preferably a 5-membered ring or a 6-membered ring, or a combined polycyclic ring, and when each ring is a heterocyclic ring, the number of heteroatoms is preferably 1 to 5.

The hetero atom of the heterocyclic ring is preferably a nitrogen atom, a sulfur atom or an oxygen atom. Examples of the ring to be formed include chroman rings.

In the formula (2B), when a plurality of-CRs are present²¹Is equal to X²¹～X²⁴When a plurality of R²¹(e.g., X)²¹And X²²is-CR²¹Adjacent when R is ═ o²¹Each other, X²²And X²³is-CR²¹Adjacent when R is ═ o²¹Each other, X²³And X²⁴is-CR²¹Adjacent when R is ═ o²¹Each other) may be bonded to each other to form a ring.

Examples of the form in which the groups represented by formula (5B) are linked to each other to form a ring include a form in which compound B has a fused ring structure.

The fused ring structure may be a structure in which an aromatic ring or a non-aromatic ring is fused to a ring having hydroxyl groups adjacently arranged in formula (2B).

Examples of the fused ring include the above-mentioned rings as R¹¹And rings formed by bonding to each other.

R²¹For example, hydrogen atom or Hammett substituent constant σ is preferable_pA substituent greater than 0.

And, R²¹Preferably a hydrogen atom or any one of the above groups of substituents T.

The compound B preferably has at least one R of any one of the above-mentioned substituent groups T²¹。

And, X²¹～X²⁴Is also preferably R²¹Being hydroxy-CR²¹＝，X²¹And X²⁴Is also preferably R²¹Being hydroxy-CR²¹＝。

The compound B is preferably a compound represented by the following formula (2-2B) or a compound represented by the formula (2-3B).

[ chemical formula 12]

In the formula (2-2B), Rx^2-2Represents a hydrogen atom or a hydroxyl group.

R^2-2And R as defined above²¹The meaning is the same. R^2-2Preferably a group having a vinylidene group or any of the substituent groups T, more preferably-CO-R^T1、-CO-O-R^T1or-CO-NH-R^T1。

In the formula (2-3B), X^2-3represents-CH ═ or a nitrogen atom.

R^2-3aAnd R^2-3bEach independently of the above-mentioned R²¹The meaning is the same. R^2-3aAnd R^2-3bEach independently is preferably any one of the substituent groups T, more preferably-CO-R^T1、-CO-O-R^T1or-CO-NH-R^T1。

And, R^2-3aAnd R^2-3bMay be bonded to each other to form a ring. Examples of the ring thus formed include a plurality of R' s¹¹The rings formed by bonding to each other are preferably benzene rings.

(Compound C)

The compound C is represented by the following formula (3C).

The compound C is a compound other than the compound a and the compound B.

The molecular weight of the compound C is preferably 110 to 2000, more preferably 120 to 1500.

[ chemical formula 13]

In the formula (3C), X³¹～X³⁴Each independently represents a nitrogen atom or-CR³¹＝。R³¹Represents a substituent other than a hydroxyl group or a hydrogen atom.

X³¹～X³⁴At least one preferably represents-CR³¹Is as follows. When there are more than one R³¹When a plurality of R³¹May be the same as or different from each other.

X³¹～X³⁴Is preferably-CR³¹＝。

As R³¹With the exception of hydroxyl groups. In addition, R is not excluded³¹The substituent represented by (1) may have a form of a hydroxyl group (for example, hydroxyalkyl group) as a substituent.

As by R³¹Examples of the substituent include R in the formula (1A) other than the above-mentioned hydroxyl group¹¹The substituents shown are the groups described above.

When a plurality of-CRs is present in the formula (3C)³¹When not, a plurality of R³¹May be bonded to each other to form a ring.

As an example of the mode of forming a ring, the mode described above as R can be given¹¹Each otherForm a ring by bonding.

R³¹For example, hydrogen atom or Hammett substituent constant σ is preferable_pA substituent greater than 0.

And, R³¹Preferably a hydrogen atom or any one of the above groups of substituents T.

Compound C preferably has at least one R of any one of the above substituent groups T³¹。

The compound C is preferably a compound represented by the formula (3-2C).

[ chemical formula 14]

In the formula (3-2C), R^3-2And R as defined above³¹The meaning is the same. R^3-2Preferably any one of the substituent groups T, more preferably-CO-R^T1、-CO-O-R^T1or-CO-NH-R^T1。

(Compound D)

The compound D is represented by the following formula (4D).

The compound D is a compound other than the compounds A to C.

The molecular weight of the compound D is preferably 110 to 2000, more preferably 120 to 1500.

[ chemical formula 15]

In the formula (4D), X⁴¹And X⁴²Each independently represents-CR⁴¹＝。R⁴¹Represents a hydrogen atom or a substituent.

There are two-CR⁴¹In the case of two-CR⁴¹May be the same as or different from each other.

Two R⁴¹At least one of them represents a substituent.

As by R⁴¹By substitution ofSimilarly, R in the formula (1A) is¹¹The substituents shown are the groups described above.

two-CR⁴¹They may be bonded to each other to form a ring.

That is, when X⁴¹And X⁴²is-CR⁴¹When two adjacent R⁴¹May be bonded to each other to form a ring.

The formed ring contains the vinylidene group in the formula (4D), but the formed ring is not limited to the non-aromatic ring. In addition, when a ring to which a ring is fused is also present in the formed ring (a ring including a vinylene group), the fused ring may be an aromatic ring.

R⁴¹For example, hydrogen atom or Hammett substituent constant σ is preferable_pA substituent greater than 0.

And, R⁴¹Preferably a hydrogen atom or any one of the above groups of substituents T.

The compound D preferably has at least one R of any one of the above-mentioned substituent groups T⁴¹。

The compound D is preferably a compound represented by the formula (4-2D).

[ chemical formula 16]

In the formula (4-2D), A^4-2And an alkylene group bonded at both ends to the vinylidene group in the formula to form a non-aromatic ring, wherein one or more methylene groups in the alkylene group may be substituted with an ether group, a carbonyl group, an ester group or a thioether group. The number of carbon atoms of the alkylene group is preferably 2 to 4. The above alkylene group is preferably an alkylene group in which one methylene group is substituted with an ether group.

R^4-2Is a hydrogen atom or a substituent, and is substituted with R as described above⁴¹The meaning is the same. R^4-2For example, any one of the substituent groups T or an alkyl group (preferably an alkyl group substituted with two hydroxyl groups) is preferable.

Specific examples of the compounds A to D are shown below.

[ chemical formula 17]

[ chemical formula 18]

[ chemical formula 19]

[ chemical formula 20]

[ chemical formula 21]

[ chemical formula 22]

As another embodiment of the compound having a phenolic hydroxyl group, the following compound E can be mentioned.

(Compound E)

The compound E is a compound represented by the following formula (1E).

[ chemical formula 23]

In the formula (1E), R¹¹Represents a substituent having a valence of 1. As by R¹¹To 1 valence ofThe substituent is not particularly limited, but examples thereof include an aliphatic group, an aryl group, a heteroaryl group and an aralkyl group.

Examples of the aliphatic group include a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkenyl group having 2 to 30 carbon atoms, a linear or branched alkynyl group having 2 to 30 carbon atoms, and an alicyclic hydrocarbon group having 3 to 30 carbon atoms. The above-mentioned linear or branched alkyl group having 1 to 30 carbon atoms, linear or branched alkenyl group having 2 to 30 carbon atoms, linear or branched alkynyl group having 2 to 30 carbon atoms and alicyclic hydrocarbon group having 3 to 30 carbon atoms are also disclosed as being-CH₂-may be substituted by heteroatoms. The kind of the hetero atom is not particularly limited, but may include an oxygen atom, a nitrogen atom, a sulfur atom, a selenium atom or a tellurium atom. Among them, the wiper is preferably made to have-Y in order to have more excellent antiviral activity¹-、-N(Ra)-、-C(＝Y²)-、-CON(Rb)-、-C(＝Y³)Y⁴-、-SOt-、-SO²N (Rc) -or a group combining them.

Y¹～Y⁴Each independently selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom and a tellurium atom. Among them, from the viewpoint of easier operation, oxygen atom is preferable. t represents an integer of 1 to 3. Ra, Rb and Rc each independently represent a hydrogen atom or an alkyl group, aryl group or heteroaryl group having 1 to 10 carbon atoms.

The straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms preferably has 1 to 20 carbon atoms. Specific examples thereof include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, 1-dimethylpropyl group, n-hexyl group, 2-ethylhexyl group, isohexyl group, heptyl group, octyl group, 3, 7-dimethyloctyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, arachidyl group (icosanyl group), eicosanyl group (eicosanyl group), heneicosanyl group (henicosanyl group), heneicosanyl group (docosanyl group), docosanyl group (docosanyl group), tricosanyl group (tricosanyl group), tetracosanyl group (tetracosanyl group), pentacosanyl group (pentacosanyl group), hexacosanyl group (hexacosanyl group), heptacosanyl group (heptacosanyl group), heptacosanyl group (octacosanyl group), octacosanyl group (octacosanyl group), Nonacosanyl (nonacosanyl) and triacontanol (triacontanyl).

The straight-chain or branched-chain alkenyl group having 2 to 30 carbon atoms preferably has 2 to 20 carbon atoms. Specifically, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, hexadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, hexacosenyl, heptacosenyl, octacosenyl, nonacosenyl, triacontenyl, octadecatrienyl, eicosenyl, docosenyl, butadienyl, pentadienyl, hexadienyl, and octadienyl groups.

In the straight-chain or branched-chain alkenyl group having 2 to 30 carbon atoms, the position of the unsaturated bond is not limited, and cis-and trans-isomers may be used. For example, octadecenyl includes oleyl (cis-9-octadecenyl) and elaiopcenyl (trans-9-octadecenyl), octadecadienyl includes linoleyl (cis, cis-9, 12-octadecadienyl) and octadecadienyl (trans, trans-9, 12-octadecadienyl), octadecatrienyl includes linolenyl (cis, cis-9, 12, 15-octadecatrienyl) and eicosatrienyl (trans, trans-9, 12, 15-octadecatrienyl), and hexadecenyl includes palmitoyl (cis-9-hexadecenyl).

The straight-chain or branched-chain alkynyl group having 2 to 30 carbon atoms preferably has 2 to 20 carbon atoms. Specifically, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecenyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl, eicosynyl, eicosenyl, heneicosyl (henicosyl), docosynyl, tricosyl, tetracosynyl, pentacosynyl, hexacosynyl, heptacosynyl, octacosynyl, nonacosynyl and triacontynyl.

The alicyclic hydrocarbon group having 3 to 30 carbon atoms may be any of monocyclic, polycyclic and crosslinked. Specific examples of the alicyclic hydrocarbon group include cyclopropane, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, 2-isopropyl-5-methylcyclohexane, cyclohexene, cyclohexadiene, cycloheptane, cycloheptene, cycloheptadiene, cyclooctane, cyclooctene, cyclooctadiene, cyclooctatriene, cyclononane, cyclodecane, cyclododecene, cyclodecadiene, cyclododecatriene, cycloundecane, cyclododecane, bicycloheptane, bicyclohexane, bicyclohexene, tricyclohexene, norcarane, norpinane, norcamphane, norbornene, norbornadiene, tricycloheptane, tricycloheptene, decahydronaphthalene, and adamantane.

Examples of the aryl group include aryl groups having 6 to 18 carbon atoms.

The aryl group may have a single ring structure or a condensed ring structure (condensed ring structure) in which two or more rings are condensed.

Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthryl group, a phenanthryl group, and a pyrenyl group, with a phenyl group or a naphthyl group being preferred, and a phenyl group being more preferred.

Examples of the heteroaryl group include heteroaryl groups having a monocyclic or polycyclic ring structure containing a heteroatom such as a sulfur atom, an oxygen atom, or a nitrogen atom.

The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably 3 to 18, more preferably 3 to 5.

The number of hetero atoms of the heteroaryl group is not particularly limited, but is preferably 1 to 10, more preferably 1 to 4, and still more preferably 1 to 2.

The number of ring members of the heteroaryl group is not particularly limited, but is preferably 3 to 8, more preferably 5 to 7, and further preferably 5 to 6.

Examples of the heteroaryl group include a furyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a pteridinyl group, a pyrazinyl group, a quinoxalinyl group, a pyrimidinyl group, a quinazolinyl group, a pyridazinyl group, a cinnolinyl group, a phthalazinyl group, a triazinyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, an imidazolyl group, a benzimidazolyl group, a pyrazolyl group, an indazolyl group, an isoxazolyl group, a benzisoxazolyl group, an isothiazolyl group, a benzisothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, a benzofuranyl group, a thienyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl.

Examples of the aralkyl group include groups in which one hydrogen atom of the linear or branched alkyl group having 1 to 30 carbon atoms is substituted with the aryl group or the heteroaryl group. Specific examples of the aralkyl group include a benzyl group, a phenethyl group and a naphthylmethyl group.

The aliphatic group, the aryl group, the heteroaryl group and the aralkyl group may have a substituent. The substituent is not particularly limited, and examples thereof include those exemplified in substituent group W described later, and alkyl groups (for example, carbon atoms are preferably 1 to 12), alkoxy groups (for example, carbon atoms are preferably 1 to 12), and hydroxyl groups are preferable.

In the formula (1E), X¹¹～X¹⁴Each independently represents a nitrogen atom or-CR¹²＝。

Wherein, at the point of higher antiviral activity, X¹¹～X¹⁴Any one of them preferably represents-CR¹²Or one or two represent a nitrogen atom, and in addition thereto represent-CR¹²Either of which more preferably represents-CR¹²＝。

R¹²Represents a 1-valent substituent other than a hydrogen atom or a hydroxyl group.

As by R¹²The 1-valent substituent other than the hydroxyl group is not particularly limited as long as it is other than the hydroxyl group, and examples thereof include those exemplified in substituent group W described laterAnd (C) a substituent (wherein, hydroxyl is excluded). As by R¹²The 1-valent substituent other than the hydroxyl group represented by (1) is preferably an alkyl group (for example, the number of carbon atoms is preferably 1 to 12), an alkenyl group (for example, the number of carbon atoms is preferably 2 to 12), an alkynyl group (for example, the number of carbon atoms is preferably 2 to 12), an alkoxy group (for example, the number of carbon atoms is preferably 1 to 12), a nitro group, a halogen atom, a carboxyl group, a cyano group, an alkoxycarbonyl group, an acyl group, a cyano group, an aryl group, a heteroaryl group, an amide group or a sulfonamide group, and more preferably an alkyl group, an alkenyl group, an alkynyl group or a halogen atom.

As R¹²Among them, a hydrogen atom is preferable.

In the formula (1), when a plurality of R's are present¹²When a plurality of R¹²May be the same or different.

(substituent group W)

Examples thereof include a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group (including a cycloalkyl group, a bicycloalkyl group and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkyl group), an alkynyl group, an aryl group, a heterocyclic group (including a heteroaryl group), a cyano group, a hydroxyl group, a nitro group, an alkoxy group, an aryloxy group, a siloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), an ammonium group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, an, Imide group, phosphine group, phosphinyl group, phosphinyloxy group, phosphinylamino group, phosphonyl group, silyl group, hydrazine group, ureido group, boronic acid group (-B (OH))₂) Sulfonic acid groups, carboxyl groups, phosphoric acid groups and other known substituents.

Each group exemplified by the substituent group W may be further substituted by a group exemplified in the substituent group W. For example, a halogen atom may be substituted with an alkyl group.

When X is present¹¹And X¹²represents-CR¹²When being equal, X¹¹R in (1)¹²And X¹²R in (1)¹²May be linked to form an aromatic ring or a non-aromatic ring.

When X is present¹³And X¹⁴represents-CR¹²When being equal, X¹³R in (1)¹²And X¹⁴R in (1)¹²May be linked to form an aromatic ring or a non-aromatic ring.

When X is present¹²And X¹⁴At least one of them represents-CR¹²When being equal, X¹²R in (1)¹²And X¹⁴R in (1)¹²With R¹¹May be linked to form a non-aromatic ring.

Examples of the non-aromatic ring include a lactone ring.

Examples of the aromatic ring include a benzene ring, a pyridine ring, a pyrrole ring, a furan ring, a thiophene ring, a thiazole ring, an oxazole ring, an imidazole ring, a naphthalene ring, a quinoline ring, an isoquinoline ring, a benzothiophene ring, an indole ring, a benzofuran ring, a benzimidazole ring, a benzothiazole ring, a benzoxazole ring and a benzimidazole ring.

Hereinafter, the compound represented by the formula (1E) is exemplified, but the present invention is not limited thereto.

[ chemical formula 24]

[ chemical formula 25]

[ chemical formula 26]

In addition, as other forms of the compound having a phenolic hydroxyl group, a compound having only a residue from which a hydrogen atom other than a hydrogen atom in one or more hydroxyl groups has been removed (hereinafter, also referred to as "compound F") among compounds represented by formula (1F) as an aromatic ring group of a 6-membered ring substituted with two or more hydroxyl groups, and a compound represented by formula (1G) (hereinafter, also referred to as "compound G") can be mentioned.

(Compound F)

The compound F is a compound represented by the formula (1F) as an aromatic ring group substituted with two or more hydroxyl groups, and has a residue obtained by removing only hydrogen atoms other than hydrogen atoms in one or more hydroxyl groups (hereinafter, also referred to as "residue of the formula (1F)").

Compound F has at least one residue of formula (1F).

The compound F may have only one residue of the formula (1F) in the compound, or may have two or more residues.

When the compound F has two or more residues of the formula (1F), the residues of the formula (1F) of the compound F may be directly bonded to each other, and a plurality of residues of the formula (1F) may also be bonded via a linking group.

The compound F may or may not be a polymer.

The molecular weight of the compound F which is not a polymer is preferably 110 to 2000, more preferably 120 to 1500.

The total number of residues of formula (1F) in the compound F which is not a polymer is preferably 1 to 10, more preferably 1 to 6.

The compound F which is a polymer preferably has a repeating unit comprising a residue of the formula (1F). The weight average molecular weight of the compound F which is a polymer is preferably 1000 to 100 ten thousand, more preferably 5000 to 100 ten thousand.

In the present specification, the weight average molecular weight (Mw) is defined as a polystyrene equivalent value based on GPC (Gel Permeationchromatography).

When the compound F has two or more residues of the formula (1F), the plural residues of the formula (1F) may be the same as or different from each other.

[ chemical formula 27]

In the formula (1F), X¹¹represents-C (OH), a nitrogen atom or-CR¹¹＝。

X¹²～X¹⁴Each independently represents-CR¹¹Or a nitrogen atom.

R¹¹Represents a substituent other than a hydroxyl group or a hydrogen atom.

As X¹¹Preferably, it is-C (OH) ═ or-CR¹¹More preferably, c (oh) is selected.

As X¹²～X¹⁴Is preferably-CR¹¹＝。

When there are more than one-CR¹¹When not, a plurality of R¹¹May be the same as or different from each other.

In the present specification, the term "substituent other than a hydroxyl group" may be any substituent other than "— OH", and a hydroxyl group may be included as a substituent included in the substituent. For example, with R¹¹The "substituent other than hydroxyl group" represented by (A) may be-CH₂(OH)。

As by R¹¹Specific examples of the substituent other than the hydroxyl group include a pyrylium ring, a benzopyrylium ring, a chromane ring, a pyridyl group, a pyrimidyl group, a pyrazinyl group, an oxazolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a cinnolinyl group, a pteridinyl group, etc., a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), a nitro group, a sulfo group, a phosphoric acid group, a cyano group, a nitro group, an amino group, an alkali metal oxy group (a sodyloxy group, a potassium oxy group, etc.), a sulfonic acid base (a sodium sulfonate group, etc.), a glycosyl group, a group having an ethenylene group (-C-) and a group having an ethynylene group (-C.ident.C-) A group having an ether group (. about.O-), a group having a thioether group (. about.S-), a group having an imino group (. about.C-. about.N-), a group having an ester group (. about.CO-O-) and-. about.O-CO-)Radicals, radicals having carbonyl groups (. -CO-), radicals having phosphine oxide groups (. -P (. -O) (. -)₂) Having a phosphonate group (═ O) (-O-)₂) Having a phosphate group (═ O) (-O-)₂) A group having a sulfinyl group (═ O) -, a group having a sulfonyl group (— SO)₂A radical having an amide group (-CO-N (-)₂And a group of-N (-) -CO-) having a sulfonamide group (-SO)₂-N(-*)₂and-N (-) -SO₂-) radical having azo groups (— N ═ N —), radical having trialkoxysilyl groups (— Si (OR)^S1 ₃) Group having an ammonium group (. -N)⁺(-*)₃) Having a sulfonium group (— S)⁺(-*)₂) Having a phosphonium group (. -P)⁺(-*)₃) Having an oxonium radical (. -O)⁺(-*)₂) A group having a normal carbon group (— C)⁺(-*)₂) Having a halonium group (. -X)⁺-; x halogen atom) and a group combining them.

The foregoing indicates bonding sites.

In the above examples, R^S1Represents an alkyl group. When there are more than one R in a group^S1When a plurality of R^S1May be the same as or different from each other.

The counter ion to the group having an ionic group in the examples is not particularly limited, and examples thereof include a halide ion and the like.

Further, the substituent may further have a substituent (may be a hydroxyl group without particular limitation) where possible.

The alkyl group in the above examples may be linear, branched, or have a cyclic structure. The number of carbon atoms is preferably 1 to 20.

The number of carbon atoms of the aryl group in the above examples is preferably 6 to 15, more preferably 6 to 10, and still more preferably 6.

Wherein R is¹¹Preferably hydrogen atom or Hammett substituent constant σ_pA substituent greater than 0.

Hammett substituent constant sigma_pCan refer to chem.rev.1991，91，p165-195。

As the Hammett substituent constant σ_pExamples of the substituent having a value greater than 0 include groups belonging to the substituent group T shown below. Namely, R¹¹Preferably a hydrogen atom or any one of the substituent groups T.

(substituent group T group)

Examples of the substituent T include alkoxycarbonyl, carboxyl, halogen atom, phosphoric acid group, perfluoroalkyl group, perfluoroaryl group, perfluoroalkoxy group, alkanesulfonyl group, alkanesulfonyloxy group, arylsulfonyl group, arylsulfonyloxy group, nitro group, cyano group, formyl group, alkylsulfinyl group, arylsulfinyl group, heteroarylsulfinyl group, arylazo group, heteroarylazo group, trialkoxysilyl group, -CO-R^S2、-O-CO-R^S2、-CO-NR^S2 ₂、-SO₂-NR^S2 ₂、-NR^S2(SO₂R^S2)、-N(SO₂R^S2)₂、-SO₂-NR^S2 ₂、-C(＝NR^S2)R^S2、-P(＝O)(OR^S2 ₂)、-C≡CR^S3、-N⁺R^S2 ₃、-S⁺R^S2 ₂、-P⁺R^S2 ₃、-O⁺R^S2 ₂、-C⁺R^S2 ₂、-X⁺R^S2Heteroaryl (e.g., pyridyl, pyrimidinyl, pyrazinyl, oxazolyl, imidazolyl, pyrazolyl, thiazolyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, cinnolinyl, or pteridinyl) and, relative to the aromatic ring in formula (la), at σ_pA group bonded at a position > 0) and a group combining them.

In the substituent group T, R^S2Represents a hydrogen atom or a substituent, preferably an alkyl group, an aryl group or a heteroaryl group. Wherein, the above R^S2Of the substituents represented by (a), sigma of the bonded group_pNot set to 0 or less. When there are more than one R in a group^S2When a plurality of R^S2May be the same as or different from each other.

In the substituent group T, R^S3Represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group. When there are more than one R in a group^S3When a plurality of R^S3May be the same as or different from each other.

Such as-CH-C (═ O) -O-CH₂CH₃(σ_p0.03), hammett substituent constant σ_pThe substituent having a value greater than 0 is preferably a group in which a Hammett substituent constant σ is further bonded via a conjugated group such as an ethenylene group, an ethynylene group, an imino group, an azo group, an aryl group or a heteroaryl group_pA substituent of a substituent (e.g., any one of the substituent T groups) greater than 0.

The alkyl group belonging to the substituent group T may be linear, branched or have a cyclic structure. The number of carbon atoms is preferably 1 to 20.

The number of carbon atoms of the aryl group belonging to the substituent group T is preferably 6 to 15, more preferably 6 to 10, and still more preferably 6.

When these groups can also have a substituent, they may have a substituent.

In the substituent group T, preferred are alkoxycarbonyl, -CO-NR^S2 ₂、-SO₂-NR^S2 ₂Acyl, alkanesulfonyl, arylsulfonyl, arylazo, heteroarylazo, cyano, formyl or carboxyl, more preferably alkoxycarbonyl, -CO-NR^S2 ₂Arylazo group or carboxyl group, more preferably alkoxycarbonyl group, -CO-NR^S2 ₂Arylazo group or carboxyl group.

X in the formula (1F)¹¹～X¹⁴At least one of which is-CR¹¹And in these-CR¹¹At least one of R¹¹Preferably hydrogen atom or Hammett substituent constant σ_pA substituent greater than 0.

X in the formula (1F)¹¹～X¹⁴More preferably represents a group having a Hammett substituent constant σ_pR of substituents greater than 0¹¹Of (a) to (CR)¹¹＝。

And, all of formula (1F) are represented by R¹¹A hydroxyl group represented byThe substituents other than the above-mentioned groups are preferably Hammett substituent constant σ_pA substituent greater than 0.

And, when a plurality of R exist in one compound represented by the formula (1F)¹¹When a plurality of R¹¹Each other (e.g. X)¹¹And X¹³is-CR¹¹Adjacent when R is ═ o¹¹Each other, X¹¹And X¹⁴is-CR¹¹Adjacent when R is ═ o¹¹Each other) may be connected to each other to form a ring.

The ring thus formed may be an aromatic ring (for example, an aromatic hydrocarbon ring or an aromatic heterocyclic ring) or a non-aromatic ring (for example, a non-aromatic hydrocarbon ring or a non-aromatic heterocyclic ring).

The ring to be formed may be a single ring or a plurality of rings.

The formed ring is preferably a 5-membered ring or a 6-membered ring, or a combined polycyclic ring, and when each ring is a heterocyclic ring, the number of heteroatoms is preferably 1 to 5.

Examples of the hetero atom of the heterocyclic ring include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom. Among them, a nitrogen atom, a sulfur atom or an oxygen atom is preferable.

The rings so formed are fused to the aromatic rings in formula (I) to form a fused ring structure.

As the condensed ring structure formed by the compound represented by the formula (1F), there may be mentioned, for example, an anthraquinone ring, a benzopyrylium ring, a xanthone ring, a chromane ring and a quinoline ring in which two hydroxyl groups are bonded to each other at a meta position in the aromatic ring in the formula.

Further, lichenin, bergenin, and the like can also be used as the compound represented by formula (1F) having a fused ring structure.

The ring to be formed may have a substituent (R as R) as long as the requirement of the present invention is not violated¹¹Examples of the substituent include the groups mentioned above).

Among them, the compound represented by the formula (1F) is preferably a compound represented by the formula (P).

[ chemical formula 28]

In the formula (P), R^P1Denotes the hydrogen atom or Hammett substituent constant σ_pA substituent greater than 0.

X^P1represents-C (OH), a nitrogen atom or-CR^P2＝。

X^P2～X^P3Each independently represents a nitrogen atom or-CR^P2＝。

R^P2Represents a substituent other than a hydroxyl group or a hydrogen atom, and the above-mentioned R¹¹The meaning is the same. R^P2For example, the same may be mentioned as R¹¹Groups which may be substituted for the description (e.g. hydrogen atoms, Hammett's substituent constant σ)_pSubstituents, alkyl and alkoxy groups larger than 0), preferably a hydrogen atom or a Hammett substituent constant σ)_pA substituent greater than 0.

When X is present^P1represents-CR^P2When is equal to R^P2And R^P1May be bonded to each other to form a ring. And, R^P2May be bonded to each other to form a ring, e.g. when X^P1And X^P3represents-CR^P2When not equal, two R^P2May be bonded to each other to form a ring. Examples of the mode of forming a ring include a plurality of R in the formula (1F)¹¹And bonded to each other to form a ring.

Hammett substituent constant sigma_pThe content of the substituent having a value greater than 0 is as described above, and examples thereof include any of the substituent groups T.

Among them, the compound represented by the formula (1F) is more preferably a compound represented by the formula (3F).

[ chemical formula 29]

In the formula (3F), R³¹Representing HamiltConstant of substituent σ_pA substituent greater than 0.

X³¹represents-C (OH), a nitrogen atom or-CR³²＝。

X³²～X³³Each independently represents a nitrogen atom or-CR³²＝。

R³²Denotes the hydrogen atom or Hammett substituent constant σ_pA substituent greater than 0.

R³¹And R³²May be bonded to each other to form a ring. For example, when X³¹represents-CR³²When not, the R³²And R³¹May be bonded to each other to form a ring. And, R³²May be bonded to each other to form a ring, e.g. when X³¹And X³³represents-CR³²When not equal, two R³²May be connected to each other to form a ring. As an example of a mode of forming a ring, a mode of forming a ring by bonding a plurality of R11 to each other in formula (1F) is similarly exemplified.

Further, since the compound represented by the formula (1F) is a residue (residue of the formula (1F)) obtained by removing a hydrogen atom other than a hydrogen atom in one or more hydroxyl groups from the compound represented by the formula (1F), X is a residue of the compound represented by the formula (1F)¹¹～X¹⁴At least one of them is preferably R having hydrogen atom removed¹¹Of (a) to (CR)¹¹Is as follows. I.e. X¹¹～X¹⁴At least one of (A) preferably represents R¹¹Is a hydrogen atom or a group having a hydrogen atom¹¹Is as follows. In other words, in the compound a, the compound represented by the formula (1F) is preferably a compound having one or more hydrogen atoms in addition to a hydroxyl group directly bonded to the aromatic ring in the formula. This also applies to the above-mentioned formulae (P) and (3F).

In the compound F, the "group other than the residue of the formula (1F)" to which the "residue of the formula (1F)" is bonded is not particularly limited, and may be a hydrogen atom.

However, when R in the formula (1F) has a hydrogen atom removed¹¹Of (a) to (CR)¹¹The "group other than the residue of formula (1F)" bonded to a site where a hydrogen atom removed from-CH is present is preferably a hydroxyl group (-OH) so as to be — CH ═And (3) outside.

Also, when the compound F has only one residue of the formula (1F), the compound represented by the formula (1F) preferably has only one R having a hydrogen atom removed therefrom¹¹Of (a) to (CR)¹¹Is (preferably-CH).

When the compound F has only one residue of the formula (1F), and R having a hydrogen atom removed in the formula (1F)¹¹Of (a) to (CR)¹¹Specific examples of the "group other than the residue of formula (1F)" bonded to a site where a hydrogen atom removed from-CH is present when-CH is present include the above-mentioned R¹¹The preferable ranges thereof are also the same. And the "group other than the residue of formula (1F)" and the other R present in formula (1F)¹¹May be bonded to each other to form a ring. Examples of the mode of forming a ring include a plurality of R in the formula (1F)¹¹And bonded to each other to form a ring.

When the compound F has only one residue of the formula (1F), the compound F is preferably a compound represented by the formula (Q1).

[ chemical formula 30]

X^q1represents-C (OH), a nitrogen atom or-CR^q1＝。X^q2～X^q4Each independently represents-CR^q1Or a nitrogen atom.

R^q1Represents a substituent other than the 6-membered aromatic ring group substituted with a hydroxyl group and two or more hydroxyl groups, or a hydrogen atom.

The definition of the aromatic ring group of the 6-membered ring substituted with two or more hydroxyl groups will be described in detail later.

As R^q1Examples thereof include hydrogen atoms or radicals other than R¹¹The substituent other than the hydroxyl group (excluding the group other than the aromatic ring group of the 6-membered ring substituted with a hydroxyl group and two or more hydroxyl groups) is preferably a Hami group other than the aromatic ring group of the 6-membered ring substituted with a hydroxyl group and two or more hydroxyl groupsSpecific substituent constant σ_pA substituent greater than 0 or a hydrogen atom.

As R^q1The substituent is preferably a substituent composed of the substituent group S described later or a hydrogen atom.

(substituent group S group)

Examples of the substituent S include alkoxycarbonyl, carboxyl, halogen atom, phosphoric acid group, perfluoroalkyl, perfluoroaryl, perfluoroalkoxy, alkanesulfonyl, alkanesulfonyloxy, arylsulfonyl, arylsulfonyloxy, nitro, cyano, formyl, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, arylazo, heteroarylazo, trialkoxysilyl, -CO-R^S4、-O-CO-R^S4、-CO-NR^S4 ₂、-SO₂-NR^S4 ₂、-NR^S4(SO₂R^S4)、-N(SO₂R^S4)₂、-SO₂-NR^S4 ₂、-C(＝NR^S4)R^S4、-P(＝O)(OR^S4 ₂)、-C≡CR^S4、-N⁺R^S4 ₃、-S⁺R^S4 ₂、-P⁺R^S4 ₃、-O⁺R^S4 ₂、-C⁺R^S4 ₂、-X⁺R^S4Heteroaryl (e.g., pyridyl, pyrimidinyl, pyrazinyl, oxazolyl, imidazolyl, pyrazolyl, thiazolyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, cinnolinyl, or pteridinyl) and, relative to the aromatic ring in formula (la), at σ_pA group bonded at a position > 0) and a group combining them.

In the substituent S group, R^S4Represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group. When there are more than one R in a group^S4When a plurality of R^S4May be the same as or different from each other.

When the group belonging to the substituent group S includes an alkyl group, the alkyl group may be linear, branched, or have a cyclic structure. The number of carbon atoms is preferably 1 to 20.

When the group belonging to the substituent group S contains an aryl group, the number of carbon atoms is preferably 6 to 15, more preferably 6 to 10, and further preferably 6.

When these groups may further have a substituent, they may have a substituent (as a hydroxyl group or as R)¹¹The group mentioned before the substituent group T, excluding groups other than the aromatic ring group of the 6-membered ring substituted with two or more hydroxyl groups).

In the substituent group S, preferred are alkoxycarbonyl, -CO-NR^S4 ₂、-SO₂-NR^S4 ₂Acyl, alkanesulfonyl, arylsulfonyl, arylazo, heteroarylazo, cyano, formyl or carboxyl, more preferably alkoxycarbonyl, -CO-NR^S4 ₂Arylazo group or carboxyl group, more preferably alkoxycarbonyl group, -CO-NR^S4 ₂Arylazo group or carboxyl group.

When there are more than one-CR^q1When not, a plurality of R^q1May be the same as or different from each other. Plural R^q1May be bonded to each other to form a ring.

Examples of the type of the ring to be formed include a plurality of R in the above formula (1E)¹¹A ring formed by connecting the rings to each other.

The aromatic ring group of the 6-membered ring substituted with two or more hydroxyl groups may have a valence of 1 or 2or more. Examples of the ring constituting the aromatic ring group having 6-membered rings include an aromatic hydrocarbon ring having 6-membered rings and an aromatic heterocyclic ring having 6-membered rings. The group contained in the 6-membered ring aromatic ring substituted with two or more hydroxyl groups as a part of the group also corresponds to the 6-membered ring aromatic ring group substituted with the two or more hydroxyl groups.

The compound represented by the formula (Q1) is preferably a compound represented by the formula (Q2).

[ chemical formula 31]

In the formula (Q2), R^q21Denotes a Hammett substituent constant [ sigma ] other than a 6-membered ring aromatic group substituted with a hydroxyl group and two or more hydroxyl groups_pA substituent greater than 0 or a hydrogen atom.

As R^q21Preferred is a substituent consisting of the group S of substituents or a hydrogen atom. The definitions and preferred modes of the group of substituents S are as described above.

X^q21represents-C (OH), a nitrogen atom or-CR^q22＝。

X^q22～X^q23Each independently represents a nitrogen atom or-CR^q22＝。

R^q22Represents a substituent other than the 6-membered aromatic ring group substituted with a hydroxyl group and two or more hydroxyl groups or a hydrogen atom, and the above-mentioned R^q1The meaning is the same. Wherein, as R^q22Preferably, the substituent constant σ is a Hammett substituent constant other than the aromatic ring group of the 6-membered ring substituted with a hydroxyl group and two or more hydroxyl groups_pSubstituents or hydrogen atoms greater than 0, more preferably substituents or hydrogen atoms consisting of the group of substituents S. The definitions and preferred modes of the group of substituents S are as described above.

When X is present^q21represents-CR^q22When is equal to R^q22And R^q21May be bonded to each other to form a ring. And, R^q22May be bonded to each other to form a ring, e.g. when X^q21And X^q23represents-CR^q22When not equal, two R^q22May be bonded to each other to form a ring. Examples of the type of the ring to be formed include a plurality of R in the above formula (1F)¹¹A ring formed by connecting the rings to each other.

When the compound F has m residues of the formula (1F), the number of the 6-membered aromatic ring groups substituted with two or more hydroxyl groups of the compound F is m. In addition, m represents a positive integer.

When the compound F has two or more residues of the formula (1F), the residue of the formula (1F) is preferably a group represented by the following formula (1-2F).

[ chemical formula 32]

In the formula (1-2F), X^1-2represents-CR^1-2Nitrogen atom or c (oh).

R^1-2And R in the formula (1F)¹¹The meaning is the same.

Denotes the bonding site.

When the compound F has two or more residues of the formula (1F), the compound F is preferably a compound represented by the following formula (A1F).

[ chemical formula 33]

In the formula (A1F), X^1-2And X in the formula (1-2F)^1-2The meaning is the same.

L^1-2Represents a single bond or a 2-valent linking group. Examples of the 2-valent linking group include an ether group, a carbonyl group, an ester group, a thioester group, an amide group, a sulfonamide group, a thioether group and-SO₂-、-NR^A-(R^ARepresents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group. ) 2-valent hydrocarbon groups (e.g., alkylene, alkenylene, alkynylene, and arylene), heteroarylene groups, azo groups, and combinations thereof.

Wherein L is^1-2Preferably a single bond, an ester group (preferably an ester group represented by-CO-O-and having a carbon atom in the group directly bonded to the aromatic ring in the formula) or an amide group (preferably an amide group represented by-CO-NH-and having a carbon atom in the group directly bonded to the aromatic ring in the formula).

m^z1Represents an integer of 2or more.

m^z1Preferably 2 to 10.

When m is^z1When it is 2, Z represents a single bond or a 2-valent linking group, and when m is^z1When more than 2, Z represents m^z1A valence linking group.

Wherein, when m^z1When it is 2, Z is preferably a single bond or a 2-valent linking group represented by the following formula. In the formula, Rx²Represents a hydrogen atom, a halogen atom or an alkyl group (which may be linear, branched or have a cyclic structure). the number of carbon atoms is preferably 1 to 20. Ar represents an arylene group (preferably having 1 to 20 carbon atoms, more preferably a phenylene group, a naphthylene group or an anthracenylene group, and still more preferably an anthracenylene group). Is represented by^1-2The bonding position of (2).

[ chemical formula 34]

When m is^z1In the case of 3, Z is preferably any of 3-valent linking groups represented by the following formulae. In the formula, Rx³Represents a hydrogen atom, a halogen atom or an alkyl group (which may be linear, branched or have a cyclic structure). the number of carbon atoms is preferably 1 to 20, more preferably a methyl group). Is represented by^1-2The bonding position of (2).

[ chemical formula 35]

When m is^z1In the case of 4, Z is preferably any of 4-valent linking groups represented by the following formulae. Is represented by^1-2The bonding position of (2).

[ chemical formula 36]

When m is^z1In the case of 5, Z is preferably a 5-valent linking group represented by the following formula. Is represented by^1-2The bonding position of (2).

[ chemical formula 37]

When m is^z1In the case of 6, Z is preferably a 6-valent linking group represented by the following formula. Is represented by^1-2The bonding position of (2).

[ chemical formula 38]

When the compound F is a polymer and has a repeating unit containing a residue of the formula (1F), the compound F preferably has a repeating unit represented by the following formula.

The polymer may have a repeating unit other than the repeating unit represented by the following formula.

[ chemical formula 39]

In the formula, Rx^maRepresents a hydrogen atom, a halogen atom, an alkyl group (which may be linear, branched or have a cyclic structure) having preferably 1 to 20 carbon atoms, more preferably a methyl group, or a perfluoroalkyl group (which may be linear, branched or have a cyclic structure having preferably 1 to 20 carbon atoms, more preferably a trifluoromethyl group).

Lx represents a single bond or a 2-valent linking group. Definition of 2-valent linking group with L^1-2The definition of the 2-valent linking group is the same.

X represents a residue of formula (1F).

As described above, the compound F has only a residue in which a hydrogen atom other than a hydrogen atom in one or more hydroxyl groups is removed in the compound represented by formula (1F) as an aromatic ring group of a 6-membered ring substituted with two or more hydroxyl groups.

That is, the compound F is an aromatic ring group having 6-membered rings substituted with two or more hydroxyl groups, and has only one of the hydroxyl groups disposed meta to each other with respect to all other hydroxyl groups.

In other words, the compound a does not have a 6-membered ring aromatic ring group substituted with two or more hydroxyl groups and a 6-membered ring aromatic ring group in which two hydroxyl groups are arranged at the ortho-position or the para-position to each other.

The aromatic ring group having 6 members is an aromatic ring group having 6 members in the form included in the polycyclic group, and for example, the compound a does not have a residue obtained by removing a hydrogen atom other than a hydrogen atom in one or more hydroxyl groups from 1, 2-dihydroxynaphthalene, 1, 4-dihydroxynaphthalene or1, 2, 4-trihydroxynaphthalene.

In contrast to the 6-membered aromatic ring group in which two hydroxyl groups are arranged at ortho-or para-positions to each other, which is oxidized to form a quinone body, the 6-membered aromatic ring group in which two hydroxyl groups are arranged at meta-positions to each other (residue of formula (1F)) is less likely to form a quinone body when the hydroxyl groups are arranged, and therefore, is more chemically stable than the 6-membered aromatic ring group in which two hydroxyl groups are arranged at ortho-or para-positions to each other. Therefore, the compound F has only the residue of formula (1F) as the 6-membered aromatic ring group substituted with two or more hydroxyl groups, and thus the storage stability of the solution is improved. By introducing a Hammett substituent constant σ into an aromatic ring group (residue of the formula (1F)) of a 6-membered ring in which two hydroxyl groups are arranged in meta positions to each other_pAnd the substituent group is more than 0, so that the storage stability of the solution is further improved.

(Compound G)

The compound G is a compound represented by the formula (2G). Since the compound G is also a 6-membered aromatic ring group in which all the hydroxyl groups are in the meta-position, it is chemically stable and has excellent storage stability.

[ chemical formula 40]

The compound F and the compound G are exemplified below, but the compounds are not limited to the following.

[ chemical formula 41]

[ chemical formula 42]

[ chemical formula 43]

[ chemical formula 44]

[ chemical formula 45]

[ chemical formula 46]

[ chemical formula 47]

[ chemical formula 48]

In the above compounds, Me represents a methyl group, Et represents an ethyl group, and Glu represents a glucose residue.

Other examples of the compound having a phenolic hydroxyl group include a compound represented by the following formula (1H) and a compound represented by the following compound (2 Ai).

(Compound represented by the formula (1H))

[ chemical formula 49]

In the above formula (1H), X¹¹Represents a nitrogen atom or-CR¹¹＝。

R is as defined above¹¹Represents a hydrogen atom, a hydroxyl group, and a 1-valent substituent other than an alkoxycarbonyl group.

As by R¹¹The 1-valent substituent is not particularly limited, but examples thereof include substituents exemplified in substituent group T2 shown below (except for hydroxyl group and alkoxycarbonyl group).

(substituent group T2)

Examples of the heteroaryl group include an alkyl group (preferably an alkyl group having 1 to 20 carbon atoms), an alkenyl group (preferably an alkenyl group having 2 to 20 carbon atoms), an alkynyl group (preferably an alkynyl group having 2 to 20 carbon atoms), an aryl group (preferably an aryl group having 6 to 26 carbon atoms), a heteroaryl group (preferably a heteroaryl group having 2 to 20 carbon atoms; more preferably a heteroaryl group having a 5-or 6-membered ring having at least one oxygen atom, sulfur atom or nitrogen atom; examples of the heteroaryl group include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, an oxazolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a cinnolinyl group and a pteridinyl group), an alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms), an aryloxy group (preferably an aryloxy group having 6 to 26 carbon atoms), and a heteroaryloxy group (preferably a heteroaryloxy group having 2 to 20, Heteroaryloxy of a 5-or 6-membered ring of a sulfur atom, a nitrogen atom. ) An alkylthio group (preferably an alkylthio group having 1 to 20 carbon atoms), an arylthio group (preferably an arylthio group having 6 to 26 carbon atoms), or a heteroarylthio group (preferably a heteroarylthio group having 2 to 20 carbon atoms). More preferably a 5-or 6-membered ring having at least one oxygen atom, sulfur atom, nitrogen atom. ) An aralkyl group (preferably an aralkyl group having 7 to 25 carbon atoms), an amino group (preferably an amino group, alkylamino group or arylamino group having 0 to 20 carbon atoms, for example, an amino group, N-dimethylamino group, N-diethylamino group, N-ethylamino group, anilino group, etc.), a hydroxyl group, a sulfonic acid group, a carboxyl group, a phosphoric acidA halogen atom (preferably fluorine, chlorine, bromine or iodine), a nitro group, a cyano group, a formyl group, a perfluoroalkyl group (preferably a perfluoroalkyl group having 1 to 20 carbon atoms), a perfluoroaryl group (preferably a perfluoroaryl group having 6 to 26 carbon atoms), a perfluoroalkoxy group (preferably a perfluoroalkyl group having 1 to 20 carbon atoms), an alkoxycarbonyl group (-CO)₂R¹¹¹) Acyl (-COR)¹¹²) Acyloxy (-OCOR)¹¹³) Sulfonamide (-SO)₂NR¹¹⁴R¹¹⁵) Phosphonic acid ester group (-PO (OR)¹¹⁶) (OH) OR-PO (OR)¹¹⁷)₂) Trialkoxysilyl (-Si (OR)¹¹⁸)₃) Amide (-CONR)¹¹⁹R¹²⁰，-NR¹²¹COR¹²²) Ammonium (-N)⁺R¹²³ ₃) Sulfonium group (-S)⁺R¹²⁴R¹²⁵) Phosphonium (-P)⁺R¹²⁶R¹²⁷) Oxygen onium group (-O)⁺R¹²⁸R¹²⁹) N-carbon radical (-C)⁺R¹³⁰R¹³¹) And a halonium group (-X)⁺R¹³²: x represents a halogen atom. ) Imino (-C ═ NR)¹³³) Alkanesulfonyl (-SO)₂R¹³⁴) Alkanesulfonyloxy (-OSO)₂R¹³⁵) Alkyl sulfinyl (-SOR)¹³⁶) Aryl or heteroarylsulfonyl (-SO)₂Ar), aryl or heteroaryl sulfonyloxy (-OSO)₂Ar), aryl or heteroarylsulfinyl (-osaar), and aryl or heteroarylazo (-N ═ N-Ar), and the like.

R is as defined above¹¹¹～R¹¹⁸Each independently represents a 1-valent substituent. As by R¹¹¹～R¹¹⁸The 1-valent substituent(s) is (are) preferably an aliphatic hydrocarbon group (which may be linear, branched or cyclic), an aryl group (preferably an aryl group having 6 to 26 carbon atoms) or a heteroaryl group (preferably a heteroaryl group having 2 to 20 carbon atoms; more preferably a 5-or 6-membered ring having at least one oxygen atom, sulfur atom or nitrogen atom).

R is as defined above¹¹⁹～R¹³³Each independently represents a hydrogen atom or a 1-valent substituent.

As by R¹¹⁹～R¹³³Specific examples of the substituent having a valence of 1 include the above-mentioned R¹¹¹～R¹¹⁸The substituent exemplified above is a substituent represented by a 1-valent substituent.

R is as defined above¹³⁴～R¹³⁶Each independently represents an aliphatic hydrocarbon group (which may be linear, branched, or cyclic).

Ar represents an aryl group (preferably an aryl group having 6 to 26 carbon atoms) or a heteroaryl group (preferably a heteroaryl group having 2 to 20 carbon atoms; more preferably a heteroaryl group having a 5-or 6-membered ring having at least one oxygen atom, sulfur atom or nitrogen atom).

And, in these substituent groups T2, R¹¹⁹～R^133、R¹³⁴～R¹³⁶And each group exemplified in Ar may be further substituted with a group exemplified in the substituent group T2 described above.

When the substituent is an acidic group or a basic group, a salt thereof can be formed.

When the compound, the substituent, the linking group, or the like includes an alkyl group, an alkylene group, an alkenyl group, an alkenylene group, an alkynyl group, an alkynylene group, or the like, they may be linear, branched, or cyclic, and may be substituted or unsubstituted, as described above.

In addition, there will not be R¹¹The above-mentioned substituents represent the case of the hydroxyl group and the alkoxycarbonyl group exemplified in the substituent group T2. However, when the hydroxyl group and the alkoxycarbonyl group exemplified in the substituent group T2 are bonded to a residue obtained by removing one or more hydrogen atoms from the substituent group exemplified in the substituent group T2 to form a substituent, the substituent is represented as R¹¹The substituents indicated above are allowed.

As R in the above formula (1H)¹¹The 1-valent substituent(s) is (are) preferably an alkyl group (preferably an alkyl group having 1 to 20 carbon atoms), an alkenyl group (preferably an alkenyl group having 2 to 20 carbon atoms), an alkynyl group (preferably an alkynyl group having 2 to 20 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms), a sulfonic acid group or a salt thereof, a carboxyl group or a salt thereof, a phosphoric acid group or a salt thereof, a halogen atom (preferably fluorine, chlorine, bromine or iodine), an acetal group, a nitro group, or an aryl group or a heteroaromatic groupAzoyl (-N ═ N-Ar).

These groups may also be substituted with the groups exemplified in the substituent group T2 described above. When the alkyl group, alkenyl group, alkynyl group, or aryl group or heteroaryl azo group has a substituent, specific examples of the substituent include a hydroxyl group, an alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms), a sulfonic acid group or a salt thereof, a carboxyl group or a salt thereof, a phosphoric acid group or a salt thereof, an amino group (preferably an amino group having 0 to 20 carbon atoms), and a halogen atom.

X is above¹²～X¹⁵Each independently represents a nitrogen atom or-CR¹²＝。

R is as defined above¹²Represents a 1-valent substituent other than a hydrogen atom or a hydroxyl group.

As by R¹²The 1-valent substituent(s) represented by (a) is not particularly limited, but examples thereof include the substituents exemplified in the substituent group T2 (excluding a hydroxyl group).

As R in the above formula (1H)¹²The 1-valent substituent(s) represented by (1) is preferably an alkyl group (preferably an alkyl group having 1 to 20 carbon atoms), an alkenyl group (preferably an alkenyl group having 2 to 20 carbon atoms), an alkynyl group (preferably an alkynyl group having 2 to 20 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms), a sulfonic acid group or a salt thereof, a carboxyl group or a salt thereof, a phosphoric acid group or a salt thereof, a halogen atom (preferably fluorine, chlorine, bromine or iodine), an acetal group, a nitro group, an amino group (preferably an amino group having 0 to 20 carbon atoms), or an aryl group or a heteroarylazo group (-N-Ar).

These groups may also be substituted with the groups exemplified in the substituent group T2 described above. When the alkyl group, alkenyl group, alkynyl group, or aryl group or heteroaryl azo group has a substituent, specific examples of the substituent include a hydroxyl group (excluding a phenolic hydroxyl group) and an alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms), a sulfonic acid group or a salt thereof, a carboxyl group or a salt thereof, a phosphoric acid group or a salt thereof, and a halogen atom.

In addition, when X¹³Or X¹⁴represents-CR¹²When is equal to R¹²Groups other than carboxyl groups are preferred.

In the formula (1H), R is plural¹²Each other and R¹¹And R¹²May be joined to form a ring structure. When a plurality of R¹²Each other or R¹¹And R¹²When they are linked to each other to form a ring structure, the ring structure may be an aromatic ring or a non-aromatic ring. Further, a hetero atom may be contained.

The kind of the hetero atom is not particularly limited, but may include an oxygen atom, a nitrogen atom, a sulfur atom, a selenium atom or a tellurium atom. Among them, the wiper is preferably made to have-Y in order to have more excellent antiviral activity¹-、-N(Ra)-、-C(＝Y²)-、-CON(Rb)-、-C(＝Y³)Y⁴-、-SOt-、-SO₂N (Rc) -or a group combining them.

Y¹～Y⁴Each independently selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom and a tellurium atom. Among them, oxygen atom or sulfur atom is preferable in view of easier operation. t represents an integer of 1 to 3. Ra, Rb and Rc each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an acyl group having 1 to 10 carbon atoms, an aryl group having 6 to 16 carbon atoms or a heteroaryl group having 2 to 13 carbon atoms.

And, when a plurality of R' s¹²Each other or R¹¹And R¹²When they are linked to each other to form a ring structure, the ring structure may have a substituent (for example, a substituent exemplified in substituent group T2).

And, in the formula (1H), when there are plural R' s¹²The two or more may be the same or different.

Among the compounds represented by the formula (1H), X is preferred at a point where the antiviral activity is high¹¹represents-CR¹¹Is ═ and X¹²～X¹⁵All represent-CR¹²Is ═ or X¹¹～X¹⁵One or two of them represent a nitrogen atom, and in addition thereto represent-CR¹¹or-CR¹²＝。

The compound represented by the formula (1H) is preferably a compound containing only one phenolic hydroxyl group.

(Compound (2Ai))

The compound (2Ai) corresponds to a compound represented by the following formula (2i) which contains two or more residues from which hydrogen atoms other than hydrogen atoms in one or two hydroxyl groups have been removed (hereinafter, also referred to as "residue of formula (2 i)").

The compound (2Ai) may have a structure in which a plurality of residues of the formula (2i) are directly bonded to each other, or may have a structure in which a plurality of residues of the formula (2i) are bonded to each other via a linking group. The plural residues of formula (2i) present in compound (2Ai) may be the same as or different from each other.

In the compound (2Ai), the number of the residues of the formula (2i) is not particularly limited, but is preferably 2 to 10000.

The molecular weight (weight average molecular weight when having a molecular weight distribution) of the compound (2Ai) is not particularly limited, but is preferably 185 to 100 ten thousand, more preferably 185 to 50 ten thousand. In addition, when the compound (2Ai) is a polymer, the weight average molecular weight (Mw) is defined as a polystyrene equivalent based on gpc (gel polymerization chromatography).

Hereinafter, the residue of formula (2i) will be described first.

[ chemical formula 50]

In the above formula (2i), X²¹Represents a nitrogen atom or-CR²¹＝。R²¹Represents a 1-valent substituent other than a hydrogen atom or a hydroxyl group.

As by R²¹The 1-valent substituent(s) represented by (a) is not particularly limited, but examples thereof include the substituents exemplified in the substituent group T (except for a hydroxyl group).

X²²～X²⁵Each independently represents a nitrogen atom or-CR²²＝。R²²Represents a hydrogen atom or a substituent having a valence of 1 other than a hydroxyl group.

As by R²²The 1-valent substituent(s) represented by (a) is not particularly limited, but examples thereof include the substituents exemplified in the substituent group T (except for a hydroxyl group).

In addition, in the formula (2i)Plural R²²Each other and R²¹And R²²May be joined to form a ring structure. When a plurality of R²²Each other or R²¹And R²²When they are linked to each other to form a ring structure, the ring structure may be an aromatic ring or a non-aromatic ring. Further, a hetero atom may be contained.

The kind of the hetero atom is not particularly limited, but examples thereof include an oxygen atom, a nitrogen atom, a sulfur atom, a selenium atom and a tellurium atom.

And, in the formula (2i), when there are a plurality of R²²The two or more may be the same or different.

Among the compounds represented by the formula (2i), X is preferred at a point where the antiviral activity is high²¹represents-CR²¹Is ═ and X²²～X²⁵Any one of them represents-CR²²Is ═ or X²¹～X²⁵One or two of them represent a nitrogen atom, and in addition thereto represent-CR²¹or-CR²²＝。

The compound represented by the above formula (2i) forms a residue by removing a hydrogen atom other than a hydrogen atom in one or both of the hydroxyl groups, which is clearly shown in the formula. In other words, in the compound represented by the above formula (2i), X²¹～X²⁵One or two of them represents-CH ═ or X²¹～X²⁵One or two of them represent a group having a hydrogen atom or-CR²¹or-CR²²Is as follows. That is, the compound represented by the above formula (2i) forms a residue by removing one or two hydrogen atoms described above.

The compound represented by the above formula (2i) is preferably:

·X²¹～X²⁵at least one or two of them represent-CH ═ and a residue is formed by removing a hydrogen atom in the above-mentioned one or two-CH ═ s;

·X²¹-CR²¹＝、X²²represents-CR²²By removing one or two of the above R²¹And the above R²²Hydrogen atoms in the ring structures formed by the mutual connection to form residues;

·X²²and X²³All represent-CR²²And by removing one or two of these two R²²The hydrogen atoms of the ring structures formed by the mutual connection form residues.

Among them, the compound represented by the above formula (2i) is preferably X²¹～X²⁵At least one or two of them represent-CH ═ and a residue is formed by removing a hydrogen atom in the above-mentioned one or two-CH ═ s.

In formula (2i), the solution is preferably not a glycoside, because the solution has more excellent antiviral properties.

Next, the compound (2Ai) will be described.

As described above, the compound (2Ai) may have a structure in which a plurality of residues of formula (2i) are directly bonded to each other, or may have a structure in which a plurality of residues of formula (2i) are bonded via a linking group.

When the compound (2Ai) has a structure in which a plurality of residues of the formula (2i) are bonded via a linking group, it is preferably a compound represented by the following formula (2A-1i), a compound represented by the following formula (2A-2i), a compound represented by the following formula (2A-3i), or a polymer containing a repeating unit represented by the following formula (2A-4 i).

(Compound represented by the following formula (2A-1 i))

[ chemical formula 51]

In the above formula (2A-1i), Y²¹Represents a group represented by the following formula (2-1i), a group represented by the following formula (2-2i), or a group represented by the following formula (2-3 i). Further, the group represented by the following formula (2-1i), the group represented by the following formula (2-2i) and the group represented by the following formula (2-3i) are residues formed from the compound represented by the above formula (2i), and X²¹～X²⁵At least one of the above-mentioned groups represents-CH ═ and corresponds to a residue in which a hydrogen atom in the above-mentioned-CH ═ is removed.

[ chemical formula 52]

In addition, in the group represented by the above formula (2-1i), the group represented by the above formula (2-2i) and the group represented by the above formula (2-3i), X is²¹～X²⁵And X in the above formula (2i)²¹～X²⁵The meaning is the same.

In the above formula (2A-1i), M²¹Represents a p-valent linking group. That is, the formula (2A-1i) corresponds to a compound having p groups represented by the formula (2-1i), the formula (2-2i), or the formula (2-3 i).

p represents an integer of 2or more, preferably 2 to 10, more preferably 2 to 6.

As with M²¹The linker group is not particularly limited, but examples thereof include the following linker groups.

A 2-valent linking group

With M²¹The 2-valent linking group is not particularly limited, but examples thereof include a 2-valent hydrocarbon group (which may be a 2-valent saturated hydrocarbon group, or a 2-valent aromatic hydrocarbon group, the 2-valent saturated hydrocarbon group may be linear, branched or cyclic, and preferably has 1 to 20 carbon atoms, and examples thereof include an alkylene group, and the 2-valent aromatic hydrocarbon group may have 5 to 20 carbon atoms, and may include a phenylene group, and in addition thereto, an alkenylene group (which preferably has 2 to 20 carbon atoms), an alkynylene group (which preferably has 2 to 20 carbon atoms), a 2-valent heterocyclic group, -O-, -S-, -SO-, -O-, -S-, -C-O-, and the like₂-、-NR^A-, -CO-, - (C ═ O) O-, and a combination of two or more of them. Herein, R is^ARepresents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms), an acyl group (preferably having 2 to 12 carbon atoms), an aryl group (preferably having 1 to 16 carbon atoms) or a heteroaryl group (preferably having 2 to 13 carbon atoms).

The heterocyclic ring and the heteroaryl group are preferably 5 to 7-membered rings having at least one nitrogen atom, oxygen atom, sulfur atom or selenium atom in the ring structure, and more preferably 5 to 6-membered rings.

The above-mentioned 2-valent linking group may be further substituted. The substituent is not particularly limited, but examples thereof include the substituents exemplified in the substituent group T.

A linking group having a valence of 3or more

With M²¹The linking group having a valence of 3or more is not particularly limited, but examples thereof include a carbon atom, a silicon atom, a nitrogen atom, a p-valent aliphatic hydrocarbon ring, a p-valent aromatic hydrocarbon ring and a p-valent heterocyclic ring.

The number of carbon atoms contained in the aliphatic hydrocarbon ring is preferably 3 to 15, more preferably 3 to 10, and still more preferably 5 to 10.

The number of carbon atoms contained in the aromatic hydrocarbon ring is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10.

The heterocyclic ring is preferably a 5-to 7-membered ring having at least one nitrogen atom, oxygen atom, sulfur atom or selenium atom in the ring structure, and more preferably a 5-to 6-membered ring.

As with M²¹Specific examples of the connecting group having a valence of 3or more include groups represented by the following formulae (M1) to (M11).

In the following formulae (M1) to (M11), L represents²⁴～L⁶⁹Each independently represents a single bond or a 2-valent linking group. As by L²⁴～L⁶⁹The 2-valent linking group is not particularly limited, but examples thereof include those represented by the formula M²¹The 2-valent linking groups are the same.

R^BRepresents a substituent having a valence of 1. As by R^BThe 1-valent substituent(s) represented by (a) is not particularly limited, but examples thereof include the substituents exemplified in the substituent group T.

q represents an integer of 1 to 3, and more preferably 1 or 2.

Is represented by the above Y²¹The connection position of (2).

[ chemical formula 53]

[ chemical formula 54]

(Compound represented by the following formula (2A-2 i))

[ chemical formula 55]

In the above formula (2A-2i), Y²²And Y²³And Y in the above formula (2A-1i)²¹The meaning is the same.

L²¹And L²²Represents a single bond or a 2-valent linking group. As by L²¹And L²²With M in the above formula (2A-1i)²¹The 2-valent linking groups are the same. As L²¹And L²²The group is preferably a 2-valent linking group, preferably an alkylene group having 1 to 10 carbon atoms, and more preferably an alkylene group having 1 to 3 carbon atoms.

Z²¹Is a residue formed from a compound represented by the above formula (2i), X²¹～X²⁵Two of them represent at least-CH ═ and are preferably residues in which hydrogen atoms in the two above-mentioned-CH ═ are removed. As with Z²¹Examples of the residue represented by (1) include those represented by the following formula (2-4 i).

[ chemical formula 56]

In addition, in the group represented by the above formula (2-4i), X²¹、X²²And X²⁵And X in the above formula (2i)²¹～X²⁵The meaning is the same.

r represents an integer of 1 to 6. R is preferably 1 to 4, more preferably 1 or 2.

(Compound represented by the following formula (2A-3 i))

[ chemical formula 57]

In the above formula (2A-3i), Z²²And Z in the above formula (2A-2i)²¹The meaning is the same, and the preferred mode is the same.

L²³Represents a single bond or a 2-valent linking group. As by L²³With M in the above formula (2A-1i)²¹The 2-valent linking groups are the same. As L²³The alkyl group is preferably a 2-valent linking group, preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms.

s represents an integer of 1 to 6. R is preferably 1 to 4, more preferably 1 or 2.

(Polymer comprising repeating units represented by the following formula (2A-4 i))

[ chemical formula 58]

In the above formula (2A-4i), R²³～R²⁵Each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

Y²⁴And Y in the above formula (2A-1i)²¹The meaning is the same.

L⁷²Represents a single bond or a 2-valent linking group. As by L⁷²With M in the above formula (2A-1i)²¹The 2-valent linking groups are the same. As L⁷²Preferably a single bond, -CO₂-、-CONR^A-, -O-, an alkylene group having 1 to 10 carbon atoms or a 2-valent linking group combining these groups, more preferably a single bond, -CO₂-、-CONR^A-, -O-, an alkylene group having 1 to 3 carbon atoms, or a 2-valent linking group in which these groups are combined. R is as defined above^ARepresents a hydrogen atomAn alkyl group (preferably having 1 to 10 carbon atoms), an aryl group (preferably having 6 to 10 carbon atoms) or a heteroaryl group (preferably having 2 to 13 carbon atoms). The heteroaryl group is preferably a 5 to 7-membered ring having at least one nitrogen atom, oxygen atom, sulfur atom or selenium atom in the ring structure, and more preferably a 5 to 6-membered ring.

The above-mentioned 2-valent linking group may be further substituted. The substituent is not particularly limited, but examples thereof include the substituents exemplified in the substituent group T2.

As the compound having a phenolic hydroxyl group, the following compounds can be mentioned. In the following exemplary compounds, n and m represent molar ratios.

[ chemical formula 59]

[ chemical formula 62]

[ chemical formula 63]

[ chemical formula 64]

[ chemical formula 65]

[ chemical formula 66]

[ chemical formula 67]

[ chemical formula 68]

[ chemical formula 69]

[ chemical formula 70]

[ chemical formula 71]

[ chemical formula 72]

[ chemical formula 73]

[ chemical formula 74]

[ chemical formula 75]

[ chemical formula 76]

[ chemical formula 77]

[ chemical formula 78]

[ chemical formula 79]

[ chemical formula 80]

[ chemical formula 81]

[ chemical formula 82]

The compound having a phenolic hydroxyl group preferably contains at least one selected from the group consisting of a polyphenol compound, a compound represented by formula (1H), and a compound represented by compound (2Ai), and more preferably contains at least one selected from the group consisting of a compound represented by formula (1H) and a compound represented by compound (2Ai), in view of more excellent antiviral properties.

Compounds X other than the Compound having a phenolic hydroxyl group

Examples of the compound X other than the above-mentioned compound having a phenolic hydroxyl group include compounds having a mercapto group and compounds having an amino group as a functional group, and specific examples thereof include thioglycerol, thiophenol, phenylmethanethiol, 2, 3-butanedithiol, butanethiol, 2-butanethiol, cyclohexanethiol, cyclopentanethiol, 1, 2-ethanedithiol, 2, 3-dimercaptopropanol, 2, 5-dimethyl-3-furanthiol, 3-dimethylbutylthiol, dodecanethiol, ethanethiol, 2- (ethylthio) phenol, 2-thiofurancarbinol, heptanethiol, hexadecanethiol, 1, 6-hexanedithiol, 3-methylbutylthiol, 2-propylthiol, 3- [ (2-mercapto-1-methylpropyl) thio ] -2-butanol, and the like, 3-hydroxy-2-butanethiol, 2-methoxyphenylthiol, 2-hydroxyethylthiol, 3-mercaptohexanol, pyrazinylmethanethiol, (2or3or10) -pinane thiol, 4-methoxy-2-methyl-2-butanethiol, methanethiol, 2-methyl-3-furanthiol, 2-methyl-3-tetrahydrofuranethiol, 2-methyl-4, 5-dihydroxy-3-furanthiol, (4-tolyl) methanethiol, 3-methyl-2-butanethiol, 2-methylbutylthiol, 2-methyl-2-propylthiol, 2-naphthalenethiol, 1, 9-nonanedithiol, 1, 8-octanedithiol, octanethiol, 2-hydroxyethanethiol, 3-mercaptohexanol, pyrazinylmethanethiol, (2or3or10) -pinanethiol, 4-methoxy-2-butanethiol, methanethiol, 2-, 2,4,4,6, 6-pentamethyl-2-heptanethiol, 2-pentanethiol, 2-phenylenethiol, 1-p-menthene-8-thiol, 1, 2-propanedithiol, propanethiol, 2-pyrazinylethylthiol, 2-pyrazinylmethanethiol, grapefruit thiol, 2-thienylmethylmercaptan, 2-thiophenethiol, 1- (2-thienyl) ethanethiol, thiogeranol, thio-linalool, 2-methylphenylthiol, 1, 4-butanedithiol, 2-mercaptobenzothiazole, 3- { [ 2-methyl- (2or4), 5-dihydro-3-furyl ] thio } -2-methyltetrahydrofuran-3-thiol, 2-mercaptothiazoline, 3-mercapto-2-methylbutanol, 3-mercapto-2-methylpentanol, 3-mercapto-3-methylbutanol, 4-ethoxy-2-methyl-2-butanethiol, ethanedithiol, hexanthiol, 2-methylpropanethiol, mercaptoacetaldehyde acetal (mercaptoacetyl) diethyl mercaptan, 3-methyl-2-butenethiol, 1-dimethylheptanethiol, 2, 6-dimethylthiophenol, (S) -1-methoxy-3-heptanethiol, 1, 3-propanethiol, 1-phenylethanethiol, 5-methyl-2-thiofurancarbinol, methanediol, 4-mercapto-4-methyl-2-pentanone, bis (1-mercaptopropyl) sulfide, methyl-2-butenethiol, 1, 6-dimethylthiophenol, 2-methyl-2-butenethiol, 2-, 1, 1-propanedithiol, 3-pentanethiol, 3-hydroxy-2-methylbutylthiol, 2-heptanethiol, isopentylamine, trimethylamine, butylamine, 4-amino-5, 6-dimethylthieno [2,3-D ] pyrimidin-2 (1H) -one, 3- [ (4-amino-2, 2-dioxido-1H-2, 1, 3-benzothiadiazin-5-yl) oxy ] -2, 2-dimethyl-N-propylpropionamide, 4-diethoxy-1-butylamine, 3- (methylthio) propylamine, and butylamine, etc.

< solvent >

The above solution contains a solvent.

The content of the solvent in the solution is not particularly limited, and is preferably 0.01 to 99.8% by mass, and more preferably 0.1 to 99.7% by mass, based on the total mass of the solution. The solid component described above means a component from which the solvent in the solution agent is removed. The solid content was calculated as the solid content even when the solid content was in the form of liquid.

In the solution of the present invention, the content of the alcohol (when a plurality of types are present, the total content thereof) is 40% by mass or more based on the total mass of the solvent, and preferably more than 50% by mass, more preferably 60% by mass or more, in view of more excellent antiviral activity. The upper limit of the alcohol content is not particularly limited, but is, for example, 100 mass% or less, preferably 80 mass% or less, based on the total mass of the solvent.

One kind of alcohol may be used alone, or two or more kinds may be used in combination. When two or more alcohols are used in combination, the total content is preferably within the above range.

In the present specification, the alcohol means a compound having an alcoholic hydroxyl group, and does not include a compound having a phenolic hydroxyl group.

The alcohol is not particularly limited, but is preferably, for example, a linear, branched or cyclic alcohol (including ether alcohol) having 1 to 20 carbon atoms.

Specifically, methanol, ethanol, n-propanol, isopropanol, polyethylene glycol, propylene glycol monoacetate, glycerol, n-butanol, 2-butanol, isobutanol, t-butanol, 1, 3-butanediol, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, dipropylene glycol, n-pentanol, 2-pentanol, 3-pentanol, t-pentanol, isoamyl alcohol, 2-methylbutanol, 3-methyl-2-butanol, 3-methyl-2-butenal, 3-methyl-3-butenal, 1-penten-3-ol, n-hexanol, octanol, 2-ethyl-1-hexanol, decanol, linalool, geraniol, lauryl alcohol, myristyl alcohol, benzyl alcohol, phenethyl alcohol, cinnamyl alcohol, 3-methoxypropanol, methyl ethyl alcohol, methyl ethyl alcohol, methyl butyl alcohol, methyl, Methoxy methoxyethanol, ethylene glycol mono-n-butyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol mono-n-butyl ether, tetraethylene glycol mono-n-butyl ether, dipropylene glycol monobutyl ether, citronellol, terpineol, hydroxycitronellal dimethyl acetal, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diacetone alcohol, ethylene glycol monoisopropyl ether, and diethylene glycol monomethyl ether.

From the viewpoint of safety, the alcohol may be a food additive, preferably methanol, ethanol, propanol, isopropanol, polyethylene glycol, propylene glycol monoacetate, n-butanol, 2-butanol, 1, 3-butanediol, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, dipropylene glycol, 2-methyl-1-butanol, 1-decanol, 1-penten-3-ol, 2-ethyl-1-hexanol, 2-pentanol, 3-methyl-2-butanol, 3-methyl-2-butenal, 3-methyl-3-butenal, isoamyl alcohol, isobutanol, benzyl alcohol, citronellol, terpineol, hydroxycitronellal or hydroxycitronellal dimethyl acetal.

In order to reduce the variation in antiviral activity value, the solvent preferably contains an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms as the alcohol, in other words, both an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms.

It is considered that an alcohol having 3or more carbon atoms is more fat-soluble than an alcohol having 2or less carbon atoms, and it is easier to remove a virus itself and an organic substance (for example, dirt) containing the virus. Therefore, it is considered that when the solution contains both an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms, the variation in antiviral activity value becomes smaller.

When an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms are used in combination, the mass ratio of the mass of the alcohol having 3or more carbon atoms to the mass of the alcohol having 2or less carbon atoms in the solution (mass of the alcohol having 3or more carbon atoms/mass of the alcohol having 2or less carbon atoms) is preferably 0.01 to 0.9, more preferably 0.03 to 0.5, and still more preferably 0.03 to 0.4.

The solvent may comprise a compound other than an alcohol.

Examples of the compound other than the alcohol include water and an organic solvent (except for the alcohol).

The organic solvent is not particularly limited, but examples thereof include acetone, methyl ethyl ketone, cyclohexane, benzene, ethyl acetate, isoamyl acetate, isopropyl acetate, geranyl acetate, cyclohexyl acetate, citronellyl acetate, cinnamyl acetate, terpinyl acetate, phenylethyl acetate, butyl acetate, benzyl acetate, methyl acetate, linalyl acetate, butyric acid, ethyl butyrate, heptyl butyrate, isoamyl butyrate, cyclohexyl butyrate, dichloroethane, tetrahydrofuran, toluene, ethylene glycol dimethyl ether, acetylacetone, cyclohexanone, ethylene glycol monomethyl ether acetate, ethylene glycol ethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether acetate, 2-methylpropionaldehyde, 2-methylbutyraldehyde, 3-methyl-2-butenal, 3-methylbutyraldehyde, methyl butyraldehyde, methyl ethyl acetate, isoamyl acetate, butyl acetate, benzyl acetate, methyl acetate, linalyl acetate, butyl butyrate, ethyl butyrate, heptyl butyrate, isoamyl, Perillaldehyde, acetaldehyde, ethyl acetoacetate, isoamyl acetate, isovaleraldehyde, isobutanol, isopropyl acetate, isopropyl myristate, isoamyl isovalerate, ethyl lactate, ethyl heptanoate, octanal, ethyl octanoate, octanal, octanoic acid, ethyl octanoate, n-octanal, formic acid, isoamyl formate, geranyl formate, citronellyl formate, cinnamaldehyde, ethyl carneate, methyl carneate, citral, citronellal, diisopropyl ether, diisopropyl disulfide, diethyl ether, diethyl tartrate, diethyl pyrocarbonate, decanal, ethyl decanoate, triacetin, triethyl citrate, toluene, nonanolide, valeraldehyde, p-methylacetophenone, p-methoxybenzaldehyde, castor oil, isoamyl phenylacetate, isobutyl phenylacetate, ethyl phenylacetate, butyraldehyde, propionaldehyde, propionic acid, isoamyl propionate, ethyl propionate, Benzyl propionate, hexane, heptane, benzaldehyde, eucalyptol, ionone, terpinyl acetate, methyl amyl cinnamaldehyde, brominated vegetable oil, acetic acid, dimethyl dicarbonate, ethyl lactate, thermally oxidized soybean oil, esters of thermally oxidized soybean oil and glycerol, and liquid paraffin.

Among these, from the viewpoint of safety, preferred are food additives, and preferred are acetone, methyl ethyl ketone, ethyl acetate, isoamyl acetate, isopropyl acetate, geranyl acetate, cyclohexyl acetate, citronellyl acetate, cinnamyl acetate, terpinyl acetate, phenylethyl acetate, butyl acetate, benzyl acetate, methyl acetate, linalyl acetate, butyric acid, ethyl butyrate, heptyl butyrate, isoamyl butyrate, cyclohexyl butyrate, 2-methylpropionaldehyde, 2-methylbutyraldehyde, 3-methyl-2-butenal 3-methylbutyraldehyde, perillaldehyde, acetaldehyde, ethyl acetoacetate, isoamyl acetate, isovaleraldehyde, isobutanol, isopropyl acetate, isopropyl myristate, isovalerate, ethyl lactate, ethyl heptanoate, caprylic acid, ethyl caprylate, n-caprylic aldehyde, formic acid, ethyl acetate, isopropyl acetate, lauryl acetate, 3-methyl-2-butenal acetate, 3-methylbutyraldehyde, 3-methyl-methylbutyraldehyde, isoamyl formate, geranyl formate, citronellyl formate, cinnamaldehyde, ethyl carneate, methyl carneate, citral, citronellal, diisopropyl ether, diisopropyl disulfide, diethyl ether, diethyl tartrate, diethyl pyrocarbonate, decanal, ethyl decanoate, triacetin, triethyl citrate, toluene, nonalactone, valeraldehyde, p-methylacetophenone, p-methoxybenzaldehyde, castor oil, isoamyl phenylacetate, isobutyl phenylacetate, ethyl phenylacetate, butyraldehyde, propionaldehyde, propionic acid, isoamyl propionate, ethyl propionate, benzyl propionate, hexane, heptane, benzaldehyde, eucalyptol, ionone, terpinyl acetate, methyl amyl cinnamaldehyde, brominated vegetable oil, acetic acid, dimethyl dicarbonate, ethyl lactate, thermally oxidized soybean oil, and esters of glycerol or liquid paraffin.

< surfactant >

The above solution preferably contains a surfactant. The wiping cloth obtained by impregnating the base cloth with the solution containing the surfactant has less wiping marks and more excellent cleaning performance.

The surfactant is not particularly limited, but examples thereof include anionic surfactants, cationic surfactants, amphoteric surfactants, and the like, and nonionic surfactants.

Examples of the anionic surfactant include higher fatty acid salts such as potassium stearate and potassium behenate; alkyl ether carboxylates such as sodium lauryl ether carboxylate (hereinafter abbreviated as "POE"); N-acetyl-L-glutamate such as N-stearoyl-L-glutamic acid monosodium salt; higher alkyl sulfate salts such as sodium lauryl sulfate and sodium potassium lauryl sulfate; alkyl ether sulfate salts such as POE lauryl sulfate triethanolamine and POE lauryl sulfate sodium; n-acyl sarcosinates such as sodium lauroyl sarcosinate; higher fatty acid amide sulfonates such as N-myristoyl-N-methyltaurate; alkyl phosphates such as sodium stearate; alkyl ether sodium phosphates such as POE oleyl ether sodium phosphate and POE stearyl ether sodium phosphate; sulfosuccinates such as sodium di-2-ethylhexyl sulfosuccinate, sodium monolauroyl monoethanolamine polyoxyethylene sulfosuccinate, and sodium lauryl polypropylene glycol sulfosuccinate; alkyl benzene sulfonates such as linear dodecyl benzene sulfonic acid sodium salt, linear dodecyl benzene sulfonic acid and dodecyl diphenyl ether disulfonic acid; cholates such as sodium deoxycholate, sodium lithocholate, and sodium cholate; higher fatty acid ester sulfates such as sodium hydrogenated coconut oil fatty acid glycerol sulfate.

Examples of the cationic surfactant include alkyltrimethylammonium salts such as stearyltrimethylammonium chloride and lauryltrimethylammonium chloride; dialkyl dimethyl ammonium salts such as distearyl dimethyl ammonium chloride; alkylpyridinium salts such as poly (N, N-dimethyl-3, 5-methylpiperidine) chloride and cetylpyridinium chloride; alkyl quaternary ammonium salts; alkyl dimethyl benzyl ammonium salts; an alkylisoquinolinium salt; a dialkyl morpholinium salt; POE alkylamine; an alkylamine salt; polyamine fatty acid derivatives; a pentanol fatty acid derivative; benzalkonium chloride; benzethonium chloride; and the like.

Examples of the amphoteric surfactant include laurylaminoacetoacetic acid propylbetaine; alkyl betaine salts such as coconut oil alkyl betaine and palm kernel oil fatty acid amidopropyl betaine.

The nonionic surfactant is preferably a compound having more than 20 carbon atoms, and examples thereof include ester-type surfactants such as mono-, di-or polyglycerin fatty acid esters, propylene glycol fatty acid monoesters, sorbitan fatty acid esters, and sucrose fatty acid esters; ether types such as polyoxyethylene alkyl ether, polyalkylene alkyl ether and polyoxyethylene polyoxypropylene glycol (manufactured by Kao Corporation, EMULGEN SERIES, etc.); ester ether types such as fatty acid polyethylene glycol and fatty acid polyoxyethylene sorbitan; alkanolamide type such as fatty acid alkanolamide.

Specific examples of the nonionic surfactant include polyethylene glycol monolauryl ether, polyethylene glycol monostearyl ether, polyethylene glycol monocetyl ether, polyethylene glycol monolauryl ester, polyethylene glycol monostearyl ester, and the like.

One kind of surfactant may be used alone, or two or more kinds may be used in combination.

When the solution contains a surfactant, the content of the surfactant (when a plurality of surfactants are present, the total amount thereof) is preferably 0.01 to 2% by mass, more preferably 0.05 to 2% by mass, and still more preferably 0.05 to 1% by mass, based on the total mass of the solution.

< alkali >

The above solution preferably contains an alkali. The base is a component that functions as a pH adjuster. The content of the alkali in the solution is not particularly limited, but is preferably 0.01 to 5% by mass based on the total mass of the solution in order to obtain a wipe having more excellent antiviral activity.

One kind of the base may be used alone, or two or more kinds may be used in combination. When two or more bases are used in combination, the total content is preferably within the above range.

The base is not particularly limited, and examples thereof include metal alkoxides (e.g., sodium methoxide and sodium ethoxide), metal oxides (e.g., calcium oxide and magnesium oxide), metal hydroxides (e.g., calcium hydroxide, magnesium hydroxide, potassium hydroxide, sodium hydroxide, lithium hydroxide, aluminum hydroxide, rubidium hydroxide, cesium hydroxide, strontium hydroxide, barium hydroxide, europium (II) hydroxide, and thallium (I) hydroxide), quaternary ammonium hydroxides, organic bases (e.g., guanidine derivatives, diazabicyclo and diazabicyclononene), phosphazene bases, phosphorus-containing bicyclic organic nonionic superbases, and basic amino acids such as lysine and arginine.

Among them, sodium hydroxide, potassium hydroxide, calcium hydroxide, or tetrabutylammonium hydroxide in water are preferable from the viewpoint of safety.

< chelating agent >

The above-mentioned solution preferably contains a chelating agent. The chelating agent is a component for preventing metal ions as impurities contained in the base fabric and the solution component from precipitating as salts such as carbonate and oxide. When the solution agent contains a chelating agent, the wiping cloth obtained by impregnating the base cloth with the solution agent containing a chelating agent has less uneven wiping and more excellent cleaning performance.

The chelating agent is not particularly limited, and examples thereof include edetate salts such as ethylenediaminetetraacetic acid, calcium disodium ethylenediaminetetraacetate, and disodium ethylenediaminetetraacetate; l-tartrate salts such as L-tartaric acid, L-potassium tartrate and L-sodium tartrate; citrate salts such as citric acid, isopropyl citrate, stearyl citrate, triethyl citrate, calcium citrate, monopotassium citrate, and tripotassium citrate; gluconate such as gluconic acid, calcium gluconate and sodium gluconate; polyphosphate such as polyphosphoric acid, ammonium polyphosphate, calcium polyphosphate, potassium polyphosphate, sodium polyphosphate and the like; metaphosphates such as metaphosphoric acid, potassium metaphosphate, and sodium metaphosphate; phosphates such as phosphoric acid, potassium hydrogen phosphate, sodium hydrogen phosphate, potassium phosphate, and sodium phosphate.

The chelating agent may be used alone or in combination of two or more. When the solution contains a chelating agent, the content of the chelating agent (when a plurality of chelating agents are present, the total content thereof) is preferably 0.01 to 2% by mass, and more preferably 0.02 to 1.5% by mass, based on the total mass of the solution.

< other ingredients >

The solution agent may contain other components than those described above as long as the effect of the present invention is exhibited. Examples of such components include bactericides, disinfectants, antibacterial agents, emulsifiers, ultraviolet absorbers, humectants, thickeners/gelling agents, pH buffers, preservatives, perfumes, and coloring matters.

The above solution exhibits alkalinity.

The pH of the solution is not particularly limited, but is, for example, preferably 8.0 or more, more preferably 9.5 to 14.0, and still more preferably 10.0 to 12.0, in view of the more excellent antiviral activity of the wipe.

The pH can be measured using a bench-top pH meter "F-72S" (manufactured by HORIBA, Ltd.) using a pH electrode "6337-10D" (manufactured by HORIBA, Ltd.). The specific measurement method is described later.

In the present specification, pH means a value at 25 ℃.

< method for producing solution >

The solution can be prepared by appropriately mixing the respective components. The mixing order of the above components is not particularly limited.

[ Basebatch ]

The fibers constituting the base fabric are not particularly limited, and examples thereof include natural fibers, synthetic fibers, semi-synthetic fibers, regenerated fibers, and the like.

The fibers constituting the base fabric may be used alone or in combination of two or more.

The natural fibers are not particularly limited, and examples thereof include cellulose fibers such as cotton fibers, flax fibers, and pulp fibers; wool; silk, etc.

The synthetic fibers are not particularly limited, and examples thereof include vinylon fibers; vinylidene fibers; polyester fibers such as polyethylene terephthalate fibers, polybutylene terephthalate fibers, polytrimethylene terephthalate fibers and copolyester fibers; polyolefin fibers such as polyethylene fibers and polypropylene fibers; polyamide fibers such as nylon 6 fibers, nylon 66 fibers, nylon 610 fibers, and nylon 46 fibers; acrylic fibers such as polyacrylonitrile fibers; a polyurethane fiber; polyvinyl chloride fibers; aramid fibers; benzoic acid fibers; polyvinyl chloride fibers; phenolic resin fibers; polyvinyl fluoride fibers, and the like.

The semi-synthetic fibers are not particularly limited, and examples thereof include acetate fibers, triacetate fibers, and protein copolymer fibers.

The regenerated fiber is not particularly limited, and examples thereof include rayon, polynosic fiber, cuprammonium fiber, and lyocell fiber.

The fibers constituting the base fabric preferably include synthetic fibers, and more preferably include at least one kind of synthetic fibers selected from the group consisting of polyolefin fibers (preferably polyethylene fibers or polypropylene fibers), polyester fibers (preferably polyethylene terephthalate fibers), vinylon fibers, and nylon fibers, in view of the fact that the storage stability of the wiping cloth is more excellent.

The content of the synthetic fibers in the fibers constituting the base fabric is, for example, 30 mass% or more, preferably 80 mass% or more, and more preferably 95 mass% or more, based on the total mass of the fibers. The upper limit of the content of the synthetic fiber is, for example, 100 mass% or less with respect to the total mass of the fiber.

Among the fibers constituting the base fabric, synthetic fibers selected from the group consisting of polyolefin fibers (preferably polyethylene fibers or polypropylene fibers), polyester fibers (preferably polyethylene terephthalate fibers) and vinylon fibers are preferable, and synthetic fibers selected from the group consisting of polyolefin fibers (preferably polyethylene fibers or polypropylene fibers) and polyester fibers (preferably polyethylene terephthalate fibers) are more preferable.

The content of the cellulose-based fiber (when there are a plurality of types, the total content thereof) in the fibers constituting the base fabric is 70 mass% or less based on the total mass of the fibers, and is preferably 30 mass% or less in view of further excellent storage stability of the wiping cloth. Among these, in terms of more excellent storage stability of the wiping cloth, it is more preferable that the fibers constituting the base cloth do not substantially contain cellulose-based fibers. The term "substantially not included" means 5% by mass or less, more preferably 3% by mass or less, and still more preferably 1% by mass or less, based on the total mass of the fibers. The lower limit is not particularly limited, but may be 0 mass%.

Cellulose-based fibers mean fibers containing cellulose or derived from cellulose. Specific examples of the cellulose fibers include pulp fibers, rayon fibers, polynosic fibers, cuprammonium fibers, lyocell fibers, acetate fibers, diacetate fibers, triacetate fibers, cotton fibers, and flax fibers.

The type of the base fabric is not particularly limited, but examples thereof include woven fabric, nonwoven fabric, and knitted fabric, and among them, nonwoven fabric is preferable.

Further, the mass per unit area (mass per unit area) of the base fabric is preferably 100g/m²The following. The amount of impregnation when impregnating the base fabric with the solution is preferably 1 time or more relative to the mass of the base fabric.

[ method for producing wiping cloth ]

The method for impregnating the base fabric with the solution is not particularly limited. For example, the following methods can be mentioned: the base cloth wound in a roll form is placed in a bottle container so that the roll surface thereof is in contact with the bottom of the bottle container, and a solution is dropped from the upper roll surface side of the base cloth wound in a roll form, thereby impregnating the base cloth with the solution.

[ use of wiping cloths ]

The use of the wiping cloth is not particularly limited.

Since the wipe has an effect of inactivating viruses belonging to the family Caliciviridae, the family Orthomyxoviridae, the family Coronaviridae, and the family herpesviridae, the use of the wipe is preferably an application of acting on the viruses to reduce the activity of the viruses. Further, examples of viruses belonging to the family Caliciviridae include viruses belonging to the genus Norwalk virus, the genus Hosta virus, the genus Leporivirus, the genus Nebulivirus and the genus Rhabdoviridae, and the like, wherein the wiping cloth exhibits a superior inactivating effect on viruses belonging to the genus Norwalk virus and viruses belonging to the genus Rhabdoviridae. That is, the wiping cloth is preferably used for resisting norwalk virus, i.e., reducing the activity of norwalk virus by acting on norwalk virus.

The wiping cloth can be used as an antibacterial wiping cloth against microorganisms such as bacteria and fungi (for example, escherichia coli, staphylococcus, trichophyton, candida, aspergillus, and the like).

Examples

Hereinafter, the present invention will be described in further detail with reference to examples. The materials, the amounts used, the ratios, the contents of the treatments and the procedures described in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited to the examples shown below.

Wipes were produced using the solutions prepared by the following methods, and antiviral activity was evaluated. In addition, feline calicivirus was used in the evaluation of antiviral activity. Among them, feline calicivirus is widely known for verifying the non-activating effect of a drug on norwalk virus.

[ preparation of wiping cloth of example 1]

[ solution preparation method ]

In a glass container filled with 4-hydroxy-benzoic acid (corresponding to compound X (a compound having a phenolic hydroxyl group)) and disodium ethylenediaminetetraacetate (corresponding to a chelating agent.), alcohol (73 g of ethanol and 3g of isopropanol) was added to dissolve 4-hydroxy-benzoic acid and disodium ethylenediaminetetraacetate in the alcohol. Then, water and a 1mol/L aqueous solution of sodium hydroxide were added to the glass container so that the total amount of water became 24g and the pH of the solution preparation became 11.5, and the solution preparation used in example 1 was obtained at the blending amount shown in Table 1.

In addition, the measurement of pH was carried out by the following method.

< measurement of pH of solution >

The measurement was carried out after using a pH meter (product name "pH Water quality Analyzer LAQUA F-72S", manufactured by HORIBA, Ltd.) and a pH electrode (product name "6377-10D", manufactured by HORIBA, Ltd.) and correcting the pH with a pH standard solution. After the sample liquid is adjusted to a liquid temperature of 25 ℃, the electrode is immersed in the sample liquid and is left for about 1-2 minutes, and the pH value when the value is stable is read. The results are shown in table 1.

[ production of wiping cloth ]

Wiping cloths were produced using the above solutions. Specifically, a nonwoven fabric composed of 50 mass% of rayon fibers, 30 mass% of polyethylene terephthalate (PET) fibers, and 20 mass% of polyolefin fibers (a mixed fiber of PP fibers and PE fibers) was impregnated with the solution in an amount of 400 mass% of the nonwoven fabric, and the wipe cloth of example 1 was obtained.

The control sample-use wiping cloth of example 1 was obtained in the same manner except that sterilized distilled water was used instead of the solution agent.

[ various evaluations ]

< evaluation of antiviral Activity of wiper after production >

The wiping test was performed on the produced wiping cloth of example 1, with reference to "method for testing the sterilization performance of wet wipes (revised version 11/16/2015)" specified by japan society for health and materials industry.

Specifically, a virus solution obtained by culturing Feline calicivirus (ATCC VR-782) in MEM (minimum Essential media) medium was inoculated into a test carrier (stainless steel plate) in accordance with "method for testing the sterilization performance of wet wipes (modified from 11/16/2015)" prescribed by the Japan sanitary materials industries Association, dried, and wiped with a weight wrapped with the wipe cloth of example 1. Subsequently, the test vector was placed in 20mL of SCDLP medium, and the remaining virus was eluted from the test vector as a virus solution for the test substance. A virus solution for a control test body was obtained in the same manner as described above, except that the wipe for a control test body of example 1 was used instead of the wipe for a test body of example 1. Then, 0.1mL of the virus solution for the test body was inoculated into CRFK cells cultured on an agar medium, and adsorbed at 37 ℃ for 1 hour. Then, the test solution on the CRFK cells was washed and cultured for 2 to 3 days in an agar medium. After the cultivation, the number of clarke formed on the agar medium was counted, and the infection titer was calculated and used as "infection titer of wiping cloth". In addition, the infection titer of the prepared test specimen was calculated in the same manner as described above except that the virus liquid for the test specimen was used instead of the virus liquid for the test specimen, and the calculated infection titer was used as the "infection titer of the control wipe". The results are shown in table 1.

Formula 2: antiviral activity value ═ a-B

A above represents the usual log values for the infectious titer of the control wipe.

The above B represents a common logarithmic value of the infection titer of the wipe.

(evaluation criteria)

"AA": has antiviral activity value of 4.0 or more

"A": has antiviral activity value of 3.5 or more and less than 4.0

"B": has antiviral activity value of 3.0-3.5

"C": has antiviral activity value of 2.5 or more and less than 3.0

"D": has antiviral activity value less than 2.5

< evaluation of wiping cloth after 6 months storage >

The prepared wiper cloth of example 1 and the wiper cloth for the control test specimen of example 1 were placed in a sealed container and stored in a dark room for 6 months.

(quantification of the content of active ingredient, evaluation of pH)

Liquid components were squeezed from the wiping cloths of example 1 after 6 months of storage, and the content of the active ingredients in the liquid components (content of the active ingredients (% by mass) with respect to the total mass of the liquid components) was quantified by HPLC (high performance liquid chromatography). Further, by the above method, the pH of the liquid component was measured. The results are shown in table 1. The active ingredient as used herein means a compound having a phenolic hydroxyl group (containing phenoxy anion formed by dissociation of the phenolic hydroxyl group).

(evaluation of antiviral Activity of wiping cloth after 6 months storage)

The anti-viral activity was evaluated by the same method as the above < evaluation of anti-viral activity of wiper after preparation > using the wiper of example 1 and the wiper for control test body of example 1 stored for 6 months. The results are shown in table 1.

[ production of wiping cloths of examples 2 to 22 and comparative examples 1 to 3]

Wipes were produced according to the compositions and formulations shown in table 1 by the same method as in example 1, and the same evaluations as in example 1 were carried out.

Table 1 is shown below.

In addition, abbreviations used in table 1 are as follows.

"PET" polyethylene terephthalate

'PP' polypropylene

Polyethylene "PE

"VN" vinylon

NY nylon

Further, the "surfactant" used in Table 1 was polysorbate 20 (polyoxyethylene sorbitan monolaurate, "EMASO LL-120V" manufactured by Kao Corporation).

Also, the "chelating agent" used in table 1 is disodium ethylenediaminetetraacetic acid.

In table 1, "content (mass%) of active ingredient" in the column of the solution formulation indicates the content of active ingredient with respect to the total mass of the solution. In examples 2 to 9, examples 11 to 22, and comparative examples 1 to 3, the effective component was a compound having a phenolic hydroxyl group (phenoxy anion formed by dissociation of a hydrogen atom from a phenolic hydroxyl group). In example 10, the compound was a compound having a mercapto group (a plasma formed by dissociation of a hydrogen atom from a mercapto group).

In table 1, the method of measuring "pKa of active ingredient" in the column of the solution formulation is as described above. When the compound X as an active ingredient has a plurality of pKa values (that is, when the compound X is an acid with multi-stage dissociation), at least one of the plurality of pKa values may satisfy 7.0 to 15.0, and one of the pKa values in the range of 7.0 to 15.0 is described in table 1. In Table 1, the pKa values in examples 2 to 9, examples 11 to 22 and comparative examples 1 to 3 correspond to the pKa values at the time of dissociation of a hydrogen atom from a phenolic hydroxyl group in the compound X as an active ingredient. The pKa value in example 10 corresponds to the pKa of the compound X, which is an active ingredient, when a hydrogen atom is dissociated from a mercapto group.

The "fiber composition" in the column of the base fabric (nonwoven fabric) in table 1 indicates the content (mass%) of each fiber with respect to the total mass of the fibers.

In table 1, "content (mass%) of cellulosic fibers" in the column of the base fabric (nonwoven fabric) represents content (mass%) of cellulosic fibers with respect to the total mass of fibers.

In table 1, the "content (mass%) of the active ingredient" in the evaluation column indicates the content of the active ingredient with respect to the total mass of the liquid ingredients.

The weight average molecular weight (Mw: polystyrene equivalent) of the active ingredient used in example 5 in Table 1 was 5,000.

The "remaining amount" in the solvent column in table 1 represents a value obtained by removing the contents (% by mass) of the active ingredient, the surfactant, the chelating agent, and the pH adjuster (sodium hydroxide) from the total mass of the solution.

As is clear from the results in table 1, the wipes of examples are excellent in antiviral activity and storage stability.

Further, from the comparison of examples 4 to 12, it was confirmed that the antiviral property is more excellent when the compound X as an active ingredient is a compound having a phenolic hydroxyl group.

Further, it was confirmed from the comparison between examples 1 to 3 and examples 12 to 14 that the storage stability is more excellent when the content of the cellulose-based fiber is 30 mass% or less with respect to the total mass of the fiber (preferably, when the cellulose-based fiber is not substantially contained in the fiber).

Further, from comparison between examples 12 to 15 and example 16, it was confirmed that the storage stability was more excellent when the fibers constituting the base fabric were synthetic fibers selected from the group consisting of polyolefin fibers, polyester fibers and vinylon fibers. In particular, from comparison between examples 12 to 14 and example 15, it was confirmed that when the fibers constituting the base fabric were synthetic fibers selected from the group consisting of polyolefin fibers and polyester fibers, the pH of the solution in the wiping cloth was not easily lowered, and the storage stability was more excellent.

From the comparison of example 20 with example 22, it can be confirmed that the wipe is more excellent in antiviral activity when the solution contains a chelating agent.

From a comparison of example 13 with example 19, it can be confirmed that the wipe is more excellent in antiviral activity when the solution contains a surfactant.

From a comparison among examples 12, 20, and 21, it was confirmed that the wiping cloth was more excellent in antiviral activity when the solution agent contained an alcohol having 2or less carbon atoms and an alcohol having 3or more carbon atoms. Further, from a comparison between example 12 and example 20, it can be confirmed that the anti-viral activity of the wipe is more excellent when the alcohol content in the solution is 60 mass% or more with respect to the total mass of the solvent.