Antibacterial and antiviral agent composition, article, and method for producing an article

Abstract

To disclose a composition that can give an article antibacterial and antiviral properties as a first effect as well as water absorbing properties or antibacterial and antiviral durability as a second effect.SOLUTION: An antibacterial and antiviral agent composition contains at least two compounds of a first compound represented by formula (1), a second compound, which is a cationic compound free of silicon and having a molecular weight of 1,500 or less, and a third compound, which is selected from the group consisting of a polymer having a constitutional unit such as (A-1), and a reaction condensate of polyalkylene polyamine or acid salt thereof and dicyandiamide.SELECTED DRAWING: None

Description

Technical Field

[0001] This application discloses an antibacterial and antiviral agent composition, an article, and a method for manufacturing the article.

Background Art

[0002] Patent Document 1 discloses a method for imparting antibacterial properties to synthetic fibers by treating the synthetic fibers with a quaternary ammonium salt in the presence of a sulfate surfactant. Patent Document 2 discloses a method for imparting antibacterial and water-absorbing properties to cellulose-based fibers by treating the cellulose-based fibers with an organosilicon quaternary ammonium salt and a glycidyl ether-based compound.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0004] In addition to antibacterial and antiviral properties as a first effect, there is a demand for an antibacterial and antiviral agent composition capable of imparting a second effect. In the prior art, for example, (i) there is room for improvement in the compatibility between antibacterial and antiviral properties and water-absorbing properties. Specifically, although an organosilicon quaternary ammonium salt can impart antibacterial and antiviral properties to an article, there is a problem that it tends to reduce the water-absorbing property of the article. Although it is possible to improve the initial water-absorbing property to some extent by using a surfactant or the like in combination with the organosilicon quaternary ammonium salt, in this case, the water-absorbing property tends to decrease when washed with water or the like.

[0005] Alternatively, in the prior art, for example, (ii) there is room for improvement in achieving both antibacterial and antiviral properties and their durability (durable antibacterial and antiviral properties). Specifically, even when an antibacterial and antiviral agent such as an organosilicon quaternary ammonium salt is attached to an article to exhibit antibacterial and antiviral properties, there is a problem that the antibacterial and antiviral properties are likely to decrease when the article is washed or the like.

[0006] This application discloses an antibacterial and antiviral agent composition capable of solving at least one of the above problems (i) and (ii).

Means for Solving the Problems

[0007] As one of the means for solving the above problems, this application provides an antibacterial and antiviral agent composition containing at least two compounds out of a first compound, a second compound, and a third compound. The first compound is a compound represented by the following general formula (1). The second compound has a cationic group, does not contain silicon, and has a molecular weight of 1,500 or less. The third compound is at least one selected from the group consisting of a polymer having a structural unit derived from at least one of the following general formulas (A-1) to (C-2), a reaction condensate of a polyalkylene polyamine or its acid salt and dicyandiamide, and a polymer represented by the following general formula (D). Antibacterial and antiviral agent composition is disclosed.

[0008]

Chemical Formula

[0009]

Chemical formula

[0010]

Chemical formula

[0011]

Chemical formula

[0012]

Chemical formula

[0013]

Chemical formula

[0014]

Chemical formula

[0015]

Chemical formula

[0016] In the antibacterial and antiviral agent composition of the present disclosure, The second compound may be an alkyl quaternary ammonium salt.

[0017] In the antibacterial and antiviral agent composition of the present disclosure, the second compound may be a compound represented by the following general formula (2).

[0018]

Chemical formula

[0019] As one of the means for solving the above problems, the present application discloses an article to which the antibacterial and antiviral agent composition of the above present disclosure is attached.

[0020] As one of the means for solving the above problems, the present application attaching the antibacterial and antiviral agent composition of the above present disclosure to an object to be imparted with antibacterial and antiviral properties to obtain an article having antibacterial and antiviral properties, including a method for manufacturing an article

Advantages of the Invention

[0021] ​​The antibacterial and antiviral agent composition of the present disclosure can impart excellent antibacterial and antiviral properties to articles, and can further impart at least one of water absorbency and durable antibacterial and antiviral properties.

Mode for Carrying Out the Invention

[0022] 1. Antibacterial and antiviral agent composition The antibacterial and antiviral agent composition of the present disclosure contains at least two types of compounds among a first compound, a second compound, and a third compound. Here, the first compound is a compound represented by the following general formula (1), the second compound has a cationic group, does not contain silicon, and has a molecular weight of 1,500 or less, and the third compound is a polymer having a structural unit derived from at least one of the following general formulas (A-1) to (C-2), a reaction condensate of a polyalkylene polyamine or an acid salt thereof and dicyandiamide, and a polymer represented by the following general formula (D). Here, "at least two types of compounds among the first compound, the second compound, and the third compound" means any one of those containing the first compound and the second compound, those containing the first compound and the third compound, those containing the second compound and the third compound, and those containing the first compound, the second compound, and the third compound.

[0023] 1.1 First form The antibacterial and antiviral agent composition according to the first form contains a first compound and a second compound. According to the antibacterial and antiviral agent composition according to the first form, for example, antibacterial and antiviral properties and water absorbency can be imparted to an article.

[0024] 1.1.1 First compound The first compound is a compound represented by the following general formula (1). As shown in formula (1), the first compound is a quaternary ammonium salt containing silicon. Such a quaternary ammonium salt has excellent antibacterial properties and excellent antiviral properties.

[0025]

Chemical formula

[0026] In formula (1), specific examples of R1 include a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, an un eicosyl group, a doeicosyl group, a trieicosyl group, a tetraeicosyl group and the like. R2 and R3 may be the same group as each other. Also, R5 to R7 may be the same group as each other. Z1 may be chlorine, bromine or other halogen, but particularly high performance can be expected when it is chlorine. The same applies to the halogen in formula (2).

[0027] Among the quaternary ammonium salts represented by the formula (1), specific examples of the methoxysilane-based quaternary ammonium salts include octadecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride, dodecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride, dodecyldiisopropyl(3-trimethoxysilylpropyl)ammonium chloride, tetradecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride, tetradecyldiethyl(3-trimethoxysilylpropyl)ammonium chloride, tetradecyldi-n-propyl(3-trimethoxysilylpropyl)ammonium chloride, pentadecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride, pentadecyldiethyl(3-trimethoxysilylpropyl)ammonium chloride, pentadecyldi-n-propyl(3-trimethoxysilylpropyl)ammonium chloride, hexadecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride, hexadecyldiethyl(3-trimethoxysilylpropyl)ammonium chloride, hexadecyldi-n-propyl(3-trimethoxysilylpropyl)ammonium chloride, octadecyldiethyl(3-trimethoxysilylpropyl)ammonium chloride, octadecyldi-n-propyl(3-trimethoxysilylpropyl)ammonium chloride, and the like. Among them, tetradecyldimethyl(3-trimethoxysilylpropyl)ammonium chloride has good antibacterial and antiviral properties.

[0028] Among the quaternary ammonium salts represented by the formula (1), specific examples of the ethoxysilane-based quaternary ammonium salts include those obtained by substituting the trimethoxysilyl group with a triethoxysilyl group in those exemplified as the above methoxysilane-based quaternary ammonium salts.

[0029] 1.1.2 The second compound The second compound has a cationic group, does not contain silicon, and has a molecular weight of 1,500 or less. According to the findings of the present inventors, although the above-mentioned first compound imparts high antibacterial and antiviral properties to an article when attached to the article, it tends to inhibit the water absorption of the article. In contrast, by co-existing the second compound with the first compound as in the antibacterial and antiviral agent composition according to the first embodiment rather than using the first compound and the second compound alone, high antibacterial and antiviral properties can be achieved while water absorption is easily ensured. When the second compound is used alone, it falls off during washing and sufficient water absorption cannot be obtained after washing. However, by co-existing the first compound and the second compound, the fall-off during washing is suppressed and it remains after washing, so that sufficient water absorption can be obtained even after washing.

[0030] Examples of the cationic group constituting the second compound include an ammonium cation group and a polyoxyalkylene alkylammonium cation group. In particular, the second compound having an ammonium cation group can exhibit water absorption as well as antibacterial and antiviral properties. Examples of the ammonium cation group include a quaternary ammonium cation group.

[0031] The second compound does not contain silicon. By the second compound not containing silicon, the desired water absorption is easily ensured. The second compound may contain carbon, hydrogen and nitrogen, and may further contain oxygen, halogen, phosphorus, sulfur, etc.

[0032] The second compound has a molecular weight of 1,500 or less. The molecular weight of the second compound may be 1,000 or less or 800 or less. When the second compound has such a molecular weight, the desired water absorption is easily ensured. The lower limit of the molecular weight of the second compound is not particularly limited, and may be, for example, 200 or more.

[0033] From the perspective of further enhancing antibacterial and antiviral properties and water absorbency, the second compound may be an alkyl quaternary ammonium salt. The "alkyl quaternary ammonium salt" means a salt having a quaternary ammonium cation group, and at least one of the organic groups bonded to nitrogen is an alkyl group. The type of anion that is the counter ion of these ammonium cation groups is not particularly limited. For example, it may be monoalkyl phosphate, dialkyl phosphate, a halogen such as chlorine or bromine, methyl sulfate, ethyl sulfate, or an aromatic anion. Examples of the aromatic anion include p-toluenesulfonic acid, xylenesulfonic acid, benzoic acid, or alkylbenzenesulfonic acid, etc.

[0034] In the antibacterial and antiviral agent composition according to the first form, even when the second compound is a compound represented by the following general formula (2), the antibacterial and antiviral properties and water absorbency are further enhanced.

[0035] [Chemical formula] In formula (2), R8 is an alkyl group or an aryl group having 10 to 20 carbon atoms, R9 is a methyl group, an ethyl group, a propyl group, a butyl group, or a group represented by (AO) p H, AO is an alkylene oxide having 2 to 4 carbon atoms, p is an integer of 1 to 10, R 10 is a methyl group, an ethyl group, a benzyl group, or a hydroxyalkyl group having 2 to 4 carbon atoms, n is 1 or 2, m is 1 or 2, n + m is 3, l is 1 or 2, Z2 is monoalkyl phosphate, dialkyl phosphate, a halogen, methyl sulfate, ethyl sulfate, or an aromatic anion.

[0036] In formula (2), the number of carbon atoms of R8 may be 10 or more, or 12 or more, and may be 20 or less, or 18 or less.

[0037] In formula (2), when R9 is a methyl group, the antibacterial and antiviral properties are further improved.

[0038] In formula (2), R 10 is a hydroxyalkyl group having 2 to 4 carbon atoms, particularly a hydroxyethyl group, the antibacterial and antiviral properties are further improved.

[0039] In formula (2), when Z2 is a monoalkyl phosphate or a dialkyl phosphate, the antibacterial and antiviral properties are further improved. Examples of the alkyl group of the monoalkyl phosphate and the dialkyl phosphate include alkyl groups having 1 to 12 carbon atoms. Among them, an alkyl group having 1 to 6 carbon atoms is preferable, and an alkyl group having 2 to 4 carbon atoms is more preferable.

[0040] Specific examples of the compound represented by formula (2) include dodecyldimethylhydroxyethylammonium-butyl phosphate ester salt, tetradecyldimethylhydroxyethylammonium-butyl phosphate ester salt, dodecyldimethylhydroxyethylammonium-ethyl phosphate ester salt, tetradecyldimethylhydroxyethylammonium-ethyl phosphate ester salt, and the like. Among them, when dodecyldimethylhydroxyethylammonium-butyl phosphate ester salt is adopted, the durable water absorption is further improved together with the antibacterial and antiviral properties.

[0041] 1.1.3 Composition ratio In the antibacterial and antiviral agent composition according to the first form, the ratio of the first compound to the second compound is not particularly limited and may be appropriately determined according to the antibacterial property, antiviral property, and water absorption required for the article. For example, with the total of the first compound and the second compound being 100% by mass, the content of the first compound may be 30% by mass or more, or 40% by mass or more, and may also be 90% by mass or less, or 95% by mass or less.

[0042] 1.1.4 Adhesion amount In the antibacterial and antiviral agent composition according to the first embodiment, the ratio between the article and the total of the first compound and the second compound attached to the article is not particularly limited. For example, with respect to 100 parts by mass of the article, the total of the first compound and the second compound may be attached in an amount of 0.1 part by mass or more, or may be attached in an amount of 5 parts by mass or less.

[0043] 1.1.5 Optional Components The antibacterial and antiviral agent composition according to the first embodiment may contain other components in addition to the above antibacterial and antiviral agents. For example, the antibacterial and antiviral agent composition according to the first embodiment may contain a surfactant and water, or may contain a surfactant, an organic solvent, and water. Further, the antibacterial and antiviral agent composition according to the first embodiment may contain an acid component, an alkali component, a chelating agent, a preservative, etc. Alternatively, within a range where the desired water absorption is ensured, it may contain an antibacterial and antiviral compound other than the above-described compounds.

[0044] 1.2 Second Embodiment The antibacterial and antiviral agent composition according to the second embodiment contains at least one of the first compound and the second compound and a third compound. According to the antibacterial and antiviral agent composition according to the second embodiment, for example, antibacterial and antiviral properties and durability (durable antibacterial and antiviral properties) can be imparted to an article. Among them, according to the antibacterial and antiviral agent composition containing the second compound and the third compound, for example, antibacterial and antiviral properties, durability (durable antibacterial and antiviral properties), and water absorption can be imparted to an article. The first compound and the second compound are as described above.

[0045] The third compound is at least one selected from the group consisting of a polymer having a structural unit derived from at least one of the following general formulas (A-1) to (C-2), a reaction condensate of a polyalkylene polyamine or an acid salt thereof and dicyandiamide, and a polymer represented by the following general formula (D). Among them, a polymer containing a structural unit derived from at least one of the following general formulas (A-2) and (B-2) is preferable. The polymer may contain, for example, a structural unit derived from the following general formula (A-2) and a structural unit derived from the following general formula (B-2) in a molar ratio of 100:0 to 0:100, and more preferably in a ratio of 80:20 to 20:80. Incidentally, the polymer may have a structural unit other than those derived from at least one of the following general formulas (A-1), (A-2), (B-1), (B-2), (C-1) and (C-2), for example, a structural unit derived from triallylamine.

[0046] 1.2.1 General formulas (A-1) to (C-2) When the antibacterial and antiviral agent composition according to the second embodiment contains, as the third compound, a polymer having a structural unit derived from at least one of the following general formulas (A-1) to (C-2), it can impart antibacterial and antiviral properties and their durability to an article.

[0047] [Chemical formula] (In the formula, R 21 represents a hydrogen atom or a methyl group, R 22 represents an alkylene group or a hydroxyalkylene group having 1 to 4 carbon atoms, R 23 may be the same or different and represents an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms, -Y- represents -O- or -N(H)-, X p- represents a p-valent anion, and p is an arbitrary natural number.)

[0048] [Chemical formula] (In the formula, R 24 may be the same or different and represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms, and X p- represents a p-valent anion, and p is an arbitrary natural number.)

[0049] In general formula (A-1), from the viewpoint of further improving the antiviral property and its durability of the textile product, R 22 is preferably an alkylene group and hydroxyalkylene group having 1 to 2 carbon atoms, more preferably an alkylene group having 1 to 2 carbon atoms. Further, from the viewpoint of further improving the antiviral property and its durability of the textile product, R 23 is preferably an alkyl group and hydroxyalkyl group having 1 to 2 carbon atoms, more preferably an alkyl group having 1 to 2 carbon atoms.)

[0050] In general formulas (A-1) and (A-2), as the anion represented by X p- , there is no particular limitation as long as it can form an anion that forms a counter ion with a quaternary ammonium ion. For example, ions of monovalent or polyvalent carboxylic acids such as formic acid, acetic acid, propionic acid, gluconic acid, lactic acid, fumaric acid, maleic acid, adipic acid, alkyl phosphate ions, alkyl sulfate ions, halide ions (for example, fluoride ions, chloride ions, bromide ions, iodide ions), hydrogen sulfate ions, sulfate ions, nitrate ions, dihydrogen phosphate ions, hydrogen phosphate ions, etc. can be mentioned. Among them, from the viewpoint of further improving the antiviral property of the textile product, halide ions, alkyl sulfate ions having 1 to 2 carbon atoms, carboxylate ions, alkyl phosphate ions, nitrate ions are preferable, and halide ions, alkyl sulfate ions having 1 to 2 carbon atoms are more preferable. In the anion represented by X p- , p may be an arbitrary natural number, but from the viewpoint of further improving the antiviral property of the textile product, p is preferably an integer of 1 to 3, more preferably 1 or 2, and still more preferably 1.)

[0051] Specific examples of the compound represented by the general formula (A-1) include [2-((meth)acryloyloxy)ethyl]trimethylammonium sulfate, [2-((meth)acryloyloxy)ethyl]trimethylammonium chloride, (3-(meth)acrylamidopropyl)trimethylammonium chloride, and the like. Commercially available products include, for example, DMAEA-Q (2-(acryloyloxy)ethyltrimethylammonium chloride), DMAPAA-Q (3-acrylamidopropyl)trimethylammonium chloride) (manufactured by Kojin Co., Ltd.), Brenmer (registered trademark) QA (N,N,N,-trimethyl-N-(2-hydroxy-3-methacryloyloxypropyl)ammonium chloride) (manufactured by NOF Corporation), and the like.

[0052] The compound represented by the general formula (A-1) can be used alone or in combination of two or more.

[0053] In the general formula (A-2), R 24 From the viewpoint of further improving the antiviral property and its durability of the textile product, an alkyl group and a hydroxyalkyl group having 1 to 2 carbon atoms are preferable, and an alkyl group having 1 to 2 carbon atoms is more preferable.

[0054] Specific examples of the compound represented by the general formula (A-2) include diallyldimethylammonium chloride, diallyldiethylammonium chloride, and the like. Commercially available products include, for example, DADMAC (diallyldimethylammonium chloride, manufactured by Daiso Co., Ltd.), and the like.

[0055] The compound represented by the general formula (A-2) can be used alone or in combination of two or more.

[0056]

Chemical formula

[0057] [Chemical formula] (In the formula, R 28 represents a hydrogen atom, an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms.)

[0058] In the compound represented by the general formula (B-1), R 25 , R 26 , R 27 may be the same as R 21 , R 22 , R 23 in the general formula (A-1), respectively.)

[0059] Specific examples of the compound represented by the general formula (B-1) include dimethylaminoethyl (meth)acrylate and diethylaminoethyl (meth)acrylate. Commercially available products include, for example, Acryester DM (dimethylaminoethyl methacrylate), Acryester DE (diethylaminoethyl methacrylate) (both manufactured by Mitsubishi Chemical Corporation), and Aron (registered trademark) DA (dimethylaminoethyl acrylate) (manufactured by Toagosei Co., Ltd.).

[0060] The compound represented by the general formula (B-1) can be used alone or in combination of two or more.)

[0061] In the general formula (B-2), R 28 is preferably a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, or a hydroxyalkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, from the viewpoint of further improving the antiviral property and its durability of the textile product.)

[0062] Specific examples of the compound represented by the general formula (B-2) include, for example, diallylamine, methyldiallylamine, and the like.

[0063] The compound represented by the general formula (B-2) can be used alone or in combination of two or more.

[0064]

Chemical formula

[0065]

Chemical formula

[0066] In the general formulas (C-1) and (C-2), R 29 and R 30 are preferably a hydrogen atom, an alkyl group having 1 to 2 carbon atoms and a hydroxyalkyl group, and more preferably a hydrogen atom and an alkyl group having 1 to 2 carbon atoms, from the viewpoint of further improving the antiviral property and its durability of the textile product.

[0067] In the general formula (C-2), the anion represented by X p- is not particularly limited as long as it can form a counterion with a quaternary ammonium ion, and may be the same as or different from those in the general formulas (A-1) and (A-2). Specific examples of the anion are as described above.

[0068] The compounds represented by general formulas (C-1) and (C-2) can each be used alone or in combination of two or more.

[0069] 1.2.2 Reaction condensate of polyalkylene polyamine or its acid salt and dicyandiamide In the antibacterial and antiviral agent composition according to the second form, as the third compound, instead of or together with the polymer having the structural units according to the above general formulas (A-1) to (C-1), when it contains a reaction condensate of polyalkylene polyamine or its acid salt and dicyandiamide (having a structure derived from polyalkylene polyamine or its acid salt and a structure derived from dicyandiamide), antibacterial and antiviral properties and their durability can also be imparted to the article. Further, in the antibacterial and antiviral agent composition according to the second form, an acid salt of a Group II metal in the periodic table of elements may be used in combination with the above reaction condensate.

[0070] As the polyalkylene polyamine, linear polyamines such as diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and iminobispropylamine are preferred. These polyalkylene polyamines may be their salts, for example, salts such as hydrochloric acid, sulfuric acid, formic acid, and acetic acid.

[0071] The acid salt of the Group II metal may be a salt of beryllium, magnesium, calcium, strontium, barium, radium, zinc, cadmium, or mercury, and particularly salts of zinc, calcium, or magnesium, particularly chlorides, sulfates, formates, nitrates, etc. are preferred.

[0072] 1.2.3 General formula (D) In the antibacterial and antiviral agent composition according to the second form, as the third compound, instead of or together with the polymer having the structural units according to the above general formulas (A-1) to (C-1) and the above reaction condensate, when it contains a polymer represented by the following general formula (D), antibacterial and antiviral properties and their durability can also be imparted to the article.

[0073] [Chemical formula]

[0074] In formula (D), R 31 is an alkylene group having 1 to 4 carbon atoms, R 32 is a methyl group or an ethyl group, R 33 is a methyl group or an ethyl group, R 34 is an alkylene group having 3 or 4 carbon atoms, R 35 is a methyl group or an ethyl group, R 36 is a methyl group or an ethyl group, R 37 is an alkylene group having 1 to 4 carbon atoms, Z 31 is a halogen, and k is an arbitrary natural number.

[0075] 1.2.4 Composition ratio In the antibacterial and antiviral agent composition according to the second form, the ratio of the first compound, the second compound, and the third compound is not particularly limited and may be appropriately determined according to the antibacterial property, antiviral property, durability, etc. required for the article. For example, with the total of the first compound, the second compound, and the third compound being 100% by mass, the content of the third compound may be 10% by mass or more, 15% by mass or more, or 25% by mass or more, and may also be 99% by mass or less.

[0076] 1.2.5 Adhesion amount In the antibacterial and antiviral agent composition according to the second form, the ratio between the article and the total of the first compound, the second compound, and the third compound attached to the article is not particularly limited. For example, with respect to 100 parts by mass of the article, the total of the first compound, the second compound, and the third compound may adhere in an amount of 0.1 part by mass or more, 0.2 part by mass or more, or 0.3 part by mass or more, and may also adhere in an amount of 5 parts by mass or less, 4 parts by mass or less, or 3 parts by mass or less.

[0077] 1.2.6 Optional components The antibacterial and antiviral agent composition according to the second embodiment may contain other components in addition to the above-described first compound and / or second compound and the third compound. For example, the antibacterial and antiviral agent composition according to the second embodiment may contain a surfactant and water, or may contain a surfactant, an organic solvent, and water. Further, the antibacterial and antiviral agent composition according to the second embodiment may contain an acid component, an alkaline component, a chelating agent, a preservative, etc. Alternatively, within the range where desired properties are ensured, it may contain antibacterial and antiviral compounds other than the above-described compounds.

[0078] 2. Articles An article to which the above-described antibacterial and antiviral agent composition of the present disclosure is attached is excellent in antibacterial and antiviral properties, and is also excellent in water absorption or durable antibacterial and antiviral properties.

[0079] The type of the article is not particularly limited, and any article that requires antibacterial and antiviral properties may be used. Specific examples of the article include, for example, textile products. Alternatively, the antibacterial and antiviral agent composition of the present disclosure may be applied to articles other than textile products.

[0080] When the article is a textile product, the type of fiber constituting the textile product is not particularly limited, and it may be a natural fiber or a chemical fiber. Specific examples of the fiber include natural fibers such as cotton, hemp, silk, and wool, semi-synthetic fibers such as rayon and acetate, synthetic fibers such as polyamide (nylon, etc.), polyester, polyurethane, and polypropylene, and composite fibers and blended fibers thereof. Examples of polyamide include nylon 6 and nylon 6,6. Examples of polyester include polyethylene terephthalate, polytrimethylene terephthalate, and polylactic acid. The fiber may be in the form of yarn, knitted fabric (including interlock knitting), woven fabric (including interlacing), non-woven fabric, paper, wood, etc. The fiber may be dyed. The fiber may have some modification treatment on its surface.

[0081] 3. Method for manufacturing an article The technology of the present disclosure also has an aspect as a method for manufacturing an article having antibacterial and antiviral properties. That is, the method for manufacturing an article of the present disclosure includes attaching the antibacterial and antiviral agent composition of the present disclosure to an object to which antibacterial and antiviral properties are to be imparted to obtain an article having antibacterial and antiviral properties. As described above, the object may be a fiber, and the article may be a fiber product.

[0082] The method for attaching the above antibacterial and antiviral agent composition to an article is not particularly limited. For example, in the method of the present disclosure, the object may be brought into contact with a treatment liquid containing the antibacterial and antiviral agent composition to attach the antibacterial and antiviral agent composition to the object. The timing of treatment with the treatment liquid is not particularly limited.

[0083] The treatment liquid may be, for example, one containing the above first compound and second compound, or one containing at least one of the above first compound and second compound and a third compound. Further, the treatment liquid may contain other components such as an acid component, an alkali component, a surfactant, a chelating agent, and a preservative. The pH of the treatment liquid is not particularly limited, but may be, for example, 2 or more and 7 or less. When the antibacterial and antiviral agent composition of the present disclosure is in a liquid state, the liquid composition may be used as the treatment liquid as it is.

[0084] Specific examples of the method for treating an object with a treatment liquid include padding treatment, dipping treatment, spraying treatment, coating treatment, and the like. At this time, the treatment conditions such as the concentration of the treatment liquid and the heat treatment after application may be appropriately adjusted in consideration of various conditions such as the purpose and performance. After treating the object with the treatment liquid, a cleaning treatment such as washing with water may be performed to remove excess antibacterial and antiviral agents. Further, when the treatment liquid contains water, a drying treatment may be performed to remove the water after adhering the treatment liquid to the object. The drying method is not particularly limited, and either a dry heat method or a moist heat method may be used. The drying temperature and drying time are also not particularly limited. For example, drying may be performed at room temperature to 200°C for 10 seconds to several days. The drying temperature may be 40 to 130°C, and the drying time may be 20 seconds to 10 minutes. If necessary, heat treatment may be performed at a temperature of 100 to 190°C for about 10 seconds to 5 minutes after drying. The temperature of the heat treatment may be 130 to 190°C, and the time of the heat treatment may be 30 seconds to 5 minutes.

[0085] 4. Effects As described above, the antibacterial and antiviral agent composition of the present disclosure can impart excellent antibacterial properties, antiviral properties, and water absorbency to an article by containing a second compound together with the first compound. Alternatively, the antibacterial and antiviral agent composition of the present disclosure can impart excellent antibacterial and antiviral properties to an article by containing at least one of the first compound and the second compound and the third compound, and the article also has excellent durable antibacterial and antiviral properties.

Examples

[0086] Hereinafter, while showing examples, the effects and the like of the technology of the present disclosure will be described in more detail, but the technology of the present disclosure is not limited to the following examples.

[0087] 1. First form 1.1 Preparation of the first compound The first compound used in this example is as follows.

[0088] Compound 1A: In the following general formula (1), a compound wherein R1 is an alkyl group having 14 carbon atoms, R2 is a methyl group, R3 is a methyl group, R4 is a propylene group, R5 is a methyl group, R6 is a methyl group, R7 is a methyl group, and Z1 is chlorine.

[0089] Compound 1B: In the following general formula (1), a compound wherein R1 is an alkyl group having 18 carbon atoms, R2 is a methyl group, R3 is a methyl group, R4 is a propylene group, R5 is an ethyl group, R6 is an ethyl group, R7 is an ethyl group, and Z1 is chlorine.

[0090] Compound 1C: In the following general formula (1), a compound wherein R1 is an alkyl group having 18 carbon atoms, R2 is a methyl group, R3 is a methyl group, R4 is a propylene group, R5 is a methyl group, R6 is a methyl group, R7 is a methyl group, and Z1 is chlorine.

[0091]

Chemical formula

[0092] The synthesis conditions for Compounds 1A to 1C were as follows. As is clear from the following synthesis conditions, Compounds 1A to 1C were each used as a solution containing 40% by weight of the compound.

[0093] 1.1.1 Synthesis conditions for Compound 1A 199 parts by mass of trimethoxysilylpropyl chloride, 240 parts by mass of dimethyltetradecylamine, and 539 parts by mass of triethylene glycol monomethyl ether were placed in a reaction vessel and reacted at 150 °C for 20 hours under a nitrogen atmosphere to obtain 1100 parts by mass of a solution containing 40% by weight of tetradecyl[3-(trimethoxysilyl)propyl]dimethylammonium chloride.

[0094] 1.1.2 Synthesis conditions for Compound 1B 240 parts by mass of triethoxysilylpropyl chloride, 298 parts by mass of dimethyloctadecylamine, and 606 parts by mass of ethanol were placed in a reaction vessel and reacted at 150 °C for 20 hours under a nitrogen atmosphere to obtain 1342 parts by mass of a solution containing 40% by weight of octadecyl[3-(triethoxysilyl)propyl]dimethylammonium chloride.

[0095] 1.1.3 Synthesis conditions of Compound 1C 199 parts by mass of trimethoxysilylpropyl chloride, 298 parts by mass of dimethyloctadecylamine, and 744 parts by mass of ethanol were placed in a reaction vessel and reacted at 150 °C for 20 hours under a nitrogen atmosphere to obtain 1204 parts by mass of a solution containing 40% by weight of octadecyl[3-(trimethoxysilyl)propyl]dimethylammonium chloride.

[0096] 1.2 Preparation of the second compound The second compound used in this example is as follows. The following Compounds 2A to 2D have a cationic group, do not contain silicon, and have a molecular weight of 1,500 or less.

[0097] Compound 2A: In the following general formula (2), R8 is an alkyl group having 12 carbon atoms, R9 is a methyl group, R 10 is a hydroxyethyl group, n is 1, m is 2, l is 1, and Z2 is a mixture of Compound α which is butyl phosphate and Compound β in which R8 is an alkyl group having 12 carbon atoms, R9 is a methyl group, R 10 is a hydroxyethyl group, n is 1, m is 2, l is 2, and Z2 is dibutyl phosphate (the molar ratio of Compound α to Compound β is 1:1).

[0098] Compound 2B: In the following general formula (2), R8 is an alkyl group having 18 carbon atoms, R9 is a methyl group, R 10 is a methyl group, n is 1, m is 2, l is 1, and Z2 is a compound in which Z2 is chlorine.

[0099] Compound 2C: In the following general formula (2), R8 is an alkyl group having 12 carbon atoms, R9 is a methyl group, R 10 is a benzyl group, n is 1, m is 2, l is 1, and Z2 is chlorine.

[0100] Compound 2D: In the following general formula (2), R8 is an alkyl group having 10 carbon atoms, R9 is a methyl group, R 10 is a methyl group, n is 2, m is 1, l is 1, and Z2 is chlorine.

[0101]

Chemical formula

[0102] The synthesis conditions for Compounds 2A to 2D were as follows. As is clear from the following synthesis conditions, Compounds 2A to 2D were each used as a solution containing 15% by weight of the compound.

[0103] 1.2.1 Synthesis conditions for Compound 2A 143 parts by mass of an alkyl phosphate ester having a monomer / dimer mixing ratio of about 1 / 1 adjusted from 3 moles of n-butanol and 1 mole of phosphoric anhydride and 500 parts by mass of water were charged into a reaction vessel, and 260 parts by mass of dodecyldimethylamine was added for neutralization. 100 parts by mass of ethylene oxide was charged into this neutralized product and reacted at 100 °C for 3 hours to obtain 1000 parts by mass of a composition containing 50.0% by mass of dodecyldimethylhydroxyethylammonium-butyl phosphate salt. This was adjusted so that the dodecyldimethylhydroxyethylammonium-butyl phosphate salt was 15% by weight.

[0104] 1.2.2 Synthesis conditions for Compound 2B 297 parts by mass of stearyldimethylamine was charged into a reaction vessel. 50 parts by mass of methyl chloride was added, and after reacting at 80 °C for 2 hours, 653 parts by mass of water was added to obtain 1000 parts by mass of a composition containing 34.7% by mass of stearyltrimethylammonium chloride. This was adjusted so that the stearyltrimethylammonium chloride became 15% by weight.

[0105] 1.2.3 Synthesis conditions of Compound 2C 213 parts by mass of dimethyllaurylamine was charged into a reaction vessel. 127 parts by mass of benzyl chloride was added dropwise at 60 °C, and after reacting at 60 °C for 2 hours, 660 parts by mass of water was added to obtain 1000 parts by mass of a composition containing 34% by mass of dimethylbenzyllaurylammonium chloride. This was adjusted so that the dimethylbenzyllaurylammonium chloride became 15% by weight.

[0106] 1.2.4 Synthesis conditions of Compound 2D 311 parts by mass of didecylmethylamine was charged into a reaction vessel. 50.5 parts by mass of methyl chloride was charged and reacted at 80 °C for 2 hours, and then 638 parts by mass of water was added to obtain 1000 parts by mass of a composition containing 36.2% by mass of didecyldimethylammonium chloride. This was adjusted so that the didecyldimethylammonium chloride became 15% by weight.

[0107] 1.2.5 Synthesis conditions of comparative compound As a comparative compound of the above second compound, the following Compound 3 was prepared. The following Compound 3 is a polymer compound having a cationic group and not containing silicon, but having a molecular weight of more than 1,500. Also for Compound 3, as in Compounds 2A to 2D, the compound was used as a 15% by weight solution.

[0108] Compound 3: In the following general formula (3), R 11 is an ethylene group, R 12 is a methyl group, R 13 is a methyl group, R 14 is a propylene group, R 15 is a methyl group, R 16 is a methyl group, R17 A polymer compound in which 17 is an ethylene group and the weight average molecular weight is 30,000.

[0109]

Chemical formula

[0110] 1.3 Preparation of treatment liquid (antibacterial and antiviral agent composition) The above-mentioned first compound and second compound were mixed with a solvent, etc. at a predetermined ratio shown in Tables 1 and 2 below to obtain a treatment liquid.

[0111] 1.4 Imparting antibacterial and antiviral properties to articles 1.4.1 Reference Examples 1 to 8 Cotton knit (basis weight 165 g / m 2 , manufactured by Shikisya Co., Ltd.) or polyester knit (basis weight 120 g / m 2 , manufactured by Shikisya Co., Ltd.) was immersed in the above treatment liquid, treated at a squeezing rate of 90% (cotton) or 110% (polyester), and then heat-treated at 130 °C for 2 minutes to obtain a fiber product having antibacterial and antiviral properties.

[0112] 1.4.2 Comparative Examples 1 and 2 In the preparation of the treatment liquid, the first compound was mixed instead of the second compound (without mixing the second compound and increasing the first compound accordingly), and the treatment was carried out in the same manner as in the examples except that a treatment liquid having the composition shown in Table 2 was used to obtain a fiber product having antibacterial and antiviral properties. Reference The treatment was carried out in the same manner as in the examples, and a fiber product having antibacterial and antiviral properties was obtained.

[0113] 1.4.3 Comparative Example 3 In the preparation of the treatment liquid, the second compound was mixed instead of the first compound (without mixing the first compound and increasing the second compound accordingly), and the treatment was carried out in the same manner as in the examples except that a treatment liquid having the composition shown in Table 2 was used to obtain a fiber product having antibacterial and antiviral properties. Reference The treatment was carried out in the same manner as in the examples, and a fiber product having antibacterial and antiviral properties was obtained.

[0114] 1.4.4 Comparative Example 4 According to the method described in Patent Document 1 (Japanese Unexamined Patent Publication No. 62-177284), a fiber product having antibacterial properties was obtained. Specifically, a treatment liquid was prepared so that Compound 1C was 30 g / L and the sodium sulfate ester of lauryl alcohol ethylene oxide 3-mole adduct was 5 g / L, and a treatment bath was prepared. Cotton knit or polyester knit was immersed in the treatment bath, treated at a squeezing ratio of 90% (cotton) or 110% (polyester), and then heat-treated at 130°C for 2 minutes to obtain a fiber product having antibacterial and antiviral properties.

[0115] 1.4.5 Comparative Example 5 According to the method described in Patent Document 2 (International Publication No. 2012 / 014762), a fiber product having antibacterial properties was obtained. Specifically, a treatment liquid was prepared so that Compound 1C was 30 g / L and ethylene glycol diglycidyl ether was 10 g / L, and a treatment bath was prepared. Cotton knit or polyester knit was immersed in the treatment bath, treated at a squeezing ratio of 90% (cotton) or 110% (polyester), and then heat-treated at 130°C for 2 minutes to obtain a fiber product having antibacterial and antiviral properties.

[0116] 1.4.6 Comparative Example 6 Cotton knit or polyester knit itself was used without immersion in the treatment liquid.

[0117] 1.4.7 Comparative Example 7 Except that the third compound was mixed instead of the second compound in the preparation of the treatment liquid and a treatment liquid having the composition shown in Table 2 was used, Reference The treatment was carried out in the same manner as in the example to obtain a fiber product having antibacterial and antiviral properties.

[0118] 1.5 Washing The fiber product was washed according to the JIS L1930 (2014) C4G method. As the detergent, a JAFET standard compounded detergent (Textile Evaluation Technology Council) was used, and the detergent concentration of the washing liquid was used at 1.33 g / L. Repeated washing was carried out 10 times to confirm the change in water absorption.

[0119] 1.6 Evaluation of antibacterial property The antibacterial activity value was measured by the JIS L1902 (2015) quantitative test (8.2 liquid absorption method of bacteria), and the antibacterial performance of the textile product before washing was evaluated. Staphylococcus aureus NBRC12732 and Klebsiella pneumoniae NBRC13277 were used as the test bacteria. The results are shown in Tables 1 and 2 below. The higher the activity value shown in Tables 1 and 2, the better the antibacterial property.

[0120] 1.7 Evaluation of antiviral property The antiviral activity value was measured according to JIS L1922 (2016), and the antiviral performance of the textile product before washing was evaluated. Influenza A virus (H3N2) ATCC VR-1679 was used as the test virus. The antiviral activity value was evaluated as log(Va) - log(Vc). The results are shown in Tables 1 and 2 below. Similar to the antibacterial property, the higher the activity value shown in Tables 1 and 2, the better the antiviral property.

[0121] 1.8 Evaluation of water absorbency According to JIS L1907 (2020) (7.11 dropping method), one drop of water (about 12 mg) was dropped onto the test cloth, and the time (seconds) until the reflection by the water drop disappeared was measured to evaluate the water absorbency. The smaller the numerical value, the higher the water absorbency.

[0122] [Table 1]

[0123] [Table 2]

[0124] As is clear from the results shown in Tables 1 and 2, when a fiber product is treated with a composition containing a first compound and a second compound, the fiber product has high antibacterial and antiviral properties, high water absorbency, and the water absorbency is maintained before and after washing ( Reference Examples 1 to 8).

[0125] On the other hand, when the antibacterial and antiviral agent composition does not contain the second compound, water absorbency cannot be ensured (Comparative Examples 1 and 2).

[0126] In addition, when the antibacterial and antiviral agent composition does not contain the first compound, the antiviral property in the fiber product decreases, and the water absorbency is lost after washing (Comparative Example 3).

[0127] In addition, when melamine resin, sulfate surfactant, or polyacrylic acid / acrylic ethyl copolymer is used instead of the second compound, water absorbency cannot be ensured (Comparative Examples 4 and 5).

[0128] In addition, cotton knit and polyester knit themselves have no antibacterial or antiviral properties (Comparative Example 6).

[0129] Furthermore, when Compound 3 with a molecular weight exceeding 1,500 is used instead of the second compound, the initial and durable water absorbency decreases (Comparative Example 7).

[0130] From the above, it can be said that an antibacterial and antiviral agent composition that satisfies the following requirements can impart excellent antibacterial, antiviral, and water absorbency properties to an article. (1) The antibacterial and antiviral agent composition contains a predetermined first compound represented by the above formula (1). (2) The antibacterial and antiviral agent composition contains a second compound having a cationic group, not containing silicon, and having a molecular weight of 1,500 or less.

[0131] 2. Second form 2.1 Preparation of the third compound The details of the third compound used in this example are as follows.

[0132] Compound 3A: In the following general formula (D), R 31 is an ethylene group, R 32 is a methyl group, R 33 is a methyl group, R 34 is a propylene group, R 35 is a methyl group, R 36 is a methyl group, R 37 is an ethylene group and Z 31 is chlorine, and it is a polymer compound with a weight-average molecular weight of 30,000.

[0133]

Chemical formula

[0134] Compound 3B: Charge diallylamine (manufactured by Hiroei Chemical Co., Ltd.) (435 parts by mass) and ion-exchanged water (100 parts by mass) into a reaction vessel, and charge while dropping 35% industrial hydrochloric acid (465 parts by mass) to obtain Composition 1 containing 60% by mass of diallylamine hydrochloride. Charge Composition 1 (175 parts by mass), DADMAC (manufactured by Daiso Co., Ltd., diallyldimethylammonium chloride (non-volatile content 65% by mass)) (430 parts by mass), ion-exchanged water (382 parts by mass), and ammonium persulfate (13 parts by mass) as a polymerization initiator into another reaction vessel, and react at 80 - 90 °C for 4 hours in the presence of nitrogen gas to obtain Composition 2 (solution of Compound 3B) containing a polymer as Compound 3B.

[0135] Compound 3C: A reaction vessel was charged with methacrylate DMA-200 (dimethylaminoethyl methacrylate, manufactured by Sanyo Chemical Industries, Ltd., 110 parts by mass, 0.70 mol), isopropyl alcohol (50 parts by mass), and dimethyl sulfate (90 parts by mass, 0.71 mol) as a quaternizing agent was added dropwise over 6 hours at 60 to 70 °C in the presence of nitrogen gas. Then, the reaction was carried out at 60 to 70 °C for 1 hour to obtain Composition 3 containing 80% by mass of the compound represented by the following general formula (A-1). The Composition 3 (250 parts by mass), ion-exchanged water (500 parts by mass), and potassium persulfate (1.5 parts by mass) as a polymerization initiator were charged, and the reaction was carried out at 80 to 90 °C for 4 hours in the presence of nitrogen gas. Then, 250 parts by mass of ion-exchanged water was added to obtain Composition 4 (solution of Compound 3C) containing 20% by mass of a predetermined polymer.

[0136] [Chemical formula]

[0137] Compound 3D: The above Composition 3 (235 parts by mass, 188 parts by mass in terms of non-volatile content), methacrylate DMA-200 (10 parts by mass) as the compound represented by the following general formula (B-1), ion-exchanged water (753 parts by mass), and potassium persulfate (1.5 parts by mass) as a polymerization initiator were charged, and the reaction was carried out at 80 to 90 °C for 4 hours in the presence of nitrogen gas. Then, Denacol EX-830 (trade name, manufactured by Nagase ChemteX Corporation, polyethylene glycol diglycidyl ether (molecular weight 482)) (2 parts by mass) as a crosslinking agent having a glycidyl group was charged and reacted at 75 to 80 °C for 4 hours to obtain Composition 5 (solution of Compound 3D) containing 20% by mass of a predetermined polymer.

[0138] [Chemical formula]

[0139] To 206 parts by mass of diethylenetriamine, 128 parts by mass of ammonium chloride was gradually added while stirring at 60 to 140 °C. Further, the temperature was raised to 160 °C, and 4 parts by mass of zinc chloride and 218 parts by mass of dicyandiamide were added. The mixed reactant was heated at 230 to 250 °C for 2 hours for condensation to obtain 450 parts by mass of a pale yellow reaction condensate, and then a solution containing 45% by mass of the reaction condensate (solution of Compound 3E) was obtained.

[0140] 2.2 Preparation of treatment liquid (antibacterial and antiviral agent composition) At least one of the above-mentioned first compound and second compound and the above-mentioned third compound were mixed with a solvent or the like in a predetermined ratio shown in Table 3 below to obtain a treatment liquid.

[0141] 2.3 Imparting antibacterial and antiviral properties to articles 2.3.1 Examples 9 to 13. Reference Example 14. Example 15~ 16, Comparative Example 8 A knit made of 50% / 50% polyester / cotton (white cloth, basis weight 200 g / m 2 ) was immersed in the above treatment liquid, treated at a squeezing rate of 100%, then heat-treated at 130 °C for 2 minutes for drying, and further heat-treated at 150 °C for 1 minute to obtain a fiber product having antibacterial and antiviral properties.

[0142] 2.3.2 Comparative Example 9 The treatment liquid was adjusted so that the solution of Compound 2A was 40 g / L, Unicarezine 380-K (melamine resin: manufactured by Union Chemical) was 1.5 g / L, and Unicacatalyst P-3 (catalyst: manufactured by Union Chemical) was 0.5 g / L, and a treatment bath was prepared. A knit made of 50% / 50% polyester / cotton (white cloth, basis weight 200 g / m 2 ) was immersed in the treatment bath, treated at a squeezing rate of 100%, then heat-treated at 130 °C for 2 minutes for drying, and further heat-treated at 150 °C for 1 minute to obtain a fiber product having antibacterial and antiviral properties.

[0143] 2.3.3 Comparative Example 10 The treatment solution was adjusted so that the solution of Compound 2A was 40 g / L and the sodium sulfate ester of the 3-mole adduct of lauryl alcohol ethylene oxide was 5 g / L, and a treatment bath was prepared. A knit made of 50% polyester / 50% cotton (white cloth, basis weight 200 g / m 2 ) was immersed in the treatment bath, treated at a squeezing rate of 100%, then heat-treated at 130 °C for 2 minutes and dried, and further heat-treated at 150 °C for 1 minute to obtain a fiber product having antibacterial and antiviral properties.

[0144] 2.4 Washing The fiber product was washed according to the JIS L1930 (2014) C4G method. As the detergent, a JAFET standard compounded detergent (Fiber Evaluation Technology Council) was used, and the detergent concentration of the washing solution was used at 1.33 g / L. Repeated washing was performed 10 times to confirm the change in water absorption.

[0145] 2.5 Evaluation of antibacterial property and durable antibacterial property The antibacterial activity value was measured by the JIS L1902 (2015) quantitative test (8.2 bacterial liquid absorption method), and the antibacterial performance of the fiber product before and after washing was evaluated. As the test bacteria, Staphylococcus aureus NBRC12732 and Klebsiella pneumoniae NBRC13277 were used. The results are shown in Table 3 below. The higher the activity value shown in Table 3, the better the antibacterial property.

[0146] 2.6 Evaluation of antiviral property and durable antiviral property The antiviral activity value was measured according to JIS L1922 (2016), and the antiviral performance of the fiber product before and after washing was evaluated. As the test virus, Influenza A virus (H3N2) ATCC VR-1679 was used. The antiviral activity value was evaluated as log(Va) - log(Vc). The results are shown in Table 3 below. Similar to the antibacterial property, the higher the activity value shown in Table 3, the better the antiviral property. In JIS, when the antiviral activity value is 2.0 or more, it is considered effective, but even when the activity value is less than 2.0, the virus decreases. In this example, it is determined that there is an antiviral effect even when the activity value is 1.4.

[0147] 2.7 Evaluation of water absorbency In accordance with JIS L1907(2020)(7.11 dropping method), one drop of water (about 12 mg) was dropped onto the test cloth, and the time (seconds) until the reflection by the water drop disappeared was measured to evaluate the water absorbency. The smaller the value, the higher the water absorbency.

[0148]

Table 3

[0149] As is clear from the results shown in Table 3, when a fiber product is treated with a composition containing at least one of the first compound and the second compound and the third compound, the fiber product has high antibacterial and antiviral properties, and the antibacterial and antiviral properties are maintained after washing, that is, it has excellent durable antibacterial and antiviral properties (Examples 9 to 13. Reference Example 14. Example 15~ 16). Further, when a fiber product is treated with a composition containing the second compound and the third compound, the fiber product has high antibacterial and antiviral properties, and the antibacterial and antiviral properties are maintained after washing, and also has high water absorbency (Examples 9 to 13. Reference Example 14, Example 16).

[0150] On the other hand, when the antibacterial and antiviral agent composition does not contain the third compound, durable antiviral properties cannot be ensured (Comparative Example 8).

[0151] Further, even when melamine resin or sulfate surfactant is used instead of the third compound, durable antiviral properties cannot be ensured (Comparative Examples 9 and 10).

[0152] Also, polyester / cotton knit itself has no antibacterial or antiviral properties (Comparative Example 11).

[0153] From the above, it can be said that an antibacterial and antiviral agent composition that satisfies the following requirements can impart excellent antibacterial and antiviral properties and durability (durable antibacterial and antiviral properties) to an article. (1) The antibacterial and antiviral agent composition contains at least one of a predetermined first compound represented by the above formula (1) and a second compound having a cationic group, not containing silicon, and having a molecular weight of 1,500 or less. (2) The antibacterial and antiviral agent composition contains at least one third compound selected from the group consisting of a polymer having a structural unit derived from at least one of the above general formulas (A-1) to (C-2), a reaction condensate of a polyalkylene polyamine or an acid salt thereof and dicyandiamide, and a polymer represented by the above general formula (D).

Claims

1. An antibacterial and antiviral agent composition containing a first compound and a third compound, wherein the first compound is a compound represented by the following general formula (1), and the third compound is at least one selected from the group consisting of a polymer having a structural unit derived from at least one of the following general formulas (A-1) to (C-2), a reaction condensate of a polyalkylene polyamine or its acid salt and dicyandiamide, and a polymer represented by the following general formula (D). An antibacterial and antiviral agent composition. 【Chemical 1】 In formula (1), R １ is an alkyl group having 10 to 22 carbon atoms, R ２ is a methyl group, an ethyl group, a propyl group or a butyl group, R ３ is a methyl group, an ethyl group, a propyl group or a butyl group, R ４ is an alkylene group having 2 to 4 carbon atoms, R ５ is a methyl group or an ethyl group, R ６ is a methyl group or an ethyl group, R ７ is a methyl group or an ethyl group, Z １ is a halogen. [Chemical 2] (wherein R ２１ represents a hydrogen atom or a methyl group, R ２２ represents an alkylene group or a hydroxyalkylene group having 1 to 4 carbon atoms, R ２３ may be the same or different and represents an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms, -Y- represents -O- or -N(H)-, X ｐ－ represents a p-valent anion, and p is an arbitrary natural number.) [Chemical Formula 3] (wherein R ２４ may be the same or different and represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms, and X ｐ－ represents a p-valent anion, and p is an arbitrary natural number.) 【Chemical Formula 4】 (In the formula, R ２５ represents a hydrogen atom or a methyl group, R ２６ represents an alkylene group or a hydroxyalkylene group having 1 to 4 carbon atoms, R ２７ may be the same or different and represents an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms, and -Z- represents -O- or -N(H)-.) 【Chemical Formula 5】 (wherein R ２８ represents a hydrogen atom, an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms). 【Chemical Formula 6】 (wherein R ２９ may be the same or different and represents a hydrogen atom, an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms). 【Chemical Formula 7】 (wherein R ３０ may be the same or different and represents a hydrogen atom, an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms, and X ｐ－ represents a p-valent anion, and p is an arbitrary natural number.) [Chemical Formula 8] (wherein, R ３１ is an alkylene group having 1 to 4 carbon atoms, R ３２ is a methyl group or an ethyl group, R ３３ is a methyl group or an ethyl group, R ３４ is an alkylene group having 3 or 4 carbon atoms, R ３５ is a methyl group or an ethyl group, R ３６ is a methyl group or an ethyl group, R ３７ is an alkylene group having 1 to 4 carbon atoms, Z ３１ is a halogen, and k is an arbitrary natural number.)

2. An antibacterial and antiviral agent composition containing a second compound and a third compound, wherein the second compound is a compound represented by the following general formula (2), and the third compound is at least one selected from the group consisting of a polymer having a structural unit derived from at least one of the following general formulas (A-1) to (C-2), a reaction condensate of a polyalkylene polyamine or its acid salt and dicyandiamide, and a polymer represented by the following general formula (D). An antibacterial and antiviral agent composition. 【Chemical Formula 9】 In formula (2), R8 is an alkyl group or aryl group having 10 to 20 carbon atoms, R9 is a methyl group, ethyl group, propyl group, butyl group or a group represented by (AO)p H, AO is an alkylene oxide having 2 to 4 carbon atoms, and p is an integer from 1 to 10, R10 is a hydroxyalkyl group having 2 to 4 carbon atoms, n is 1 or 2, m is 1 or 2, n + m is 3, l is 1 or 2, Z2 is monoalkyl phosphate or dialkyl phosphate. 【Chemical Formula 10】 (In the formula, R21 represents a hydrogen atom or a methyl group, R22 represents an alkylene group or hydroxyalkylene group having 1 to 4 carbon atoms, R23 may be the same or different and represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms, -Y- represents -O- or -N(H)-, Xp- represents a p-valent anion, and p is an arbitrary natural number.) 【Chemical 11】 (In the formula, R24 may be the same or different and represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or hydroxyalkenyl group having 2 to 4 carbon atoms, Xp- represents a p-valent anion, and p is an arbitrary natural number.) 【Chemical 12】 (In the formula, R25 represents a hydrogen atom or a methyl group, R26 represents an alkylene group or a hydroxyalkylene group having 1 to 4 carbon atoms, R27 may be the same or different and represents an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms, and -Z- represents -O- or -N(H)-.) 【Chemical 13】 (In the formula, R28 represents a hydrogen atom, an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms.) 【Chemical Formula 14】 (In the formula, R29 may be the same or different and represents a hydrogen atom, an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms.) 【Chemical 15】 (In the formula, R30 may be the same or different and represents a hydrogen atom, an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, or an alkenyl group or a hydroxyalkenyl group having 2 to 4 carbon atoms, Xp− represents a p-valent anion, and p is an arbitrary natural number.) 【Chemical 16】 (In the formula, R31 is an alkylene group having 1 to 4 carbon atoms, R32 is a methyl group or an ethyl group, R33 is a methyl group or an ethyl group, R34 is an alkylene group having 3 or 4 carbon atoms, R35 is a methyl group or an ethyl group, R36 is a methyl group or an ethyl group, R37 is an alkylene group having 1 to 4 carbon atoms, Z31 is a halogen, and k is an arbitrary natural number.)

3. An article to which the antibacterial and antiviral agent composition according to claim 1 or 2 is attached. Article.

4. Attaching the antibacterial and antiviral agent composition according to claim 1 or 2 to an object to be imparted with antibacterial and antiviral properties to obtain an article having antibacterial and antiviral properties. A method for manufacturing an article, comprising:

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