Antibacterial and antiviral agents

Abstract

The present invention provides an antibacterial agent and an antiviral agent characterized by containing a pigment and a fatty acid metal salt, and an ink, a printed matter, a coating material, a coating, a plastic, a fiber, a film, a cosmetic and the like characterized by containing the antibacterial agent and the antiviral agent. It is found that an antibacterial agent or an antiviral agent containing a pigment and a fatty acid metal salt has an antibacterial and antiviral effect, and that a molded article containing the antibacterial agent or the antiviral agent also has an antibacterial and antiviral effect, and the above-mentioned problem can be solved.

Description

Technical Field

[0001] The present invention relates to antibacterial agents and antiviral agents. Background Art

[0002] In recent years, there has been a strong demand for maintaining the cleanliness of living spaces. In many households and public indoor areas, air purifiers, germicidal sprayers, etc. are installed to maintain a clean environment. However, beyond the simple air purification achieved by removing garbage and dust in the air, the high value-added achieved by imparting antibacterial, antiviral, allergen-removing, and deodorizing functions is also being promoted. As applications requiring such high added value, for example, fiber applications, plastic applications, coating applications, etc. can be cited.

[0003] In fiber applications, as methods for imparting antibacterial or antiviral properties, there are methods of mixing antibacterial agents or antiviral agents into fibers and methods of fixing a solution containing antibacterial agents or antiviral agents to the fiber surface. In the case of the method of mixing into fibers mentioned above, it is generally considered that the washing durability is high, but since it becomes high temperature during spinning, there is a possibility that organic antibacterial agents or antiviral agents may thermally decompose, and improvement in heat resistance is desired. On the other hand, in the case of the method of fixing to the fiber surface mentioned above, organic antibacterial agents or antiviral agents, such as quaternary ammonium salts, are usually used, but there is a problem that the antibacterial or antiviral properties decrease due to washing (Patent Document 1).

[0004] In coating applications, organic antibacterial agents or antiviral agents are used in the same way as in fiber applications. However, for acrylic / melamine-based coatings, etc., a curing process during heat treatment is required, and for organic antibacterial agents or antiviral agents with low heat resistance, there is a possibility of thermal deterioration of the surface to be treated and the object to be treated (Patent Document 2). From such a viewpoint, in applications where treatment is performed at high temperature, improvement in heat resistance is desired.

[0005] Regarding the content of antibacterial agents or antiviral agents, in any application, it is necessary to exhibit effects in a small amount, and how to efficiently expose antibacterial agents or antiviral agents on the surfaces of fibers, plastics, coatings, etc. has become an important technical issue. (Patent Documents 3, 4)

[0006] Prior Art Documents

[0007] Patent Documents

[0008] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2013-76188

[0009] Patent Document 2: Japanese Unexamined Patent Application Publication No. 2017-014401

[0010] Patent Document 3: Japanese Unexamined Patent Application Publication No. 2006-28453

[0011] Patent Document 4: Japanese Patent Application Laid-Open No. 2022-93225 Summary of the Invention

[0012] Problems to be Solved by the Invention

[0013] The problem to be solved by the present invention is to provide an antibacterial agent, an antiviral agent, and an ink, a printed matter, a coating material, a coating, a plastic, a fiber, a film, a cosmetic, etc. characterized by containing the antibacterial agent and the antiviral agent.

[0014] Means for Solving the Problems

[0015] The inventors et al. conducted in-depth research to solve the above problems and found that an antibacterial agent and an antiviral agent containing a pigment and a fatty acid metal salt have antibacterial and antiviral effects, and also found that a molded article containing the antibacterial agent and the antiviral agent also has antibacterial and antiviral effects, and can solve the above problems.

[0016] That is, the present invention includes the following.

[0017] [1] An antibacterial agent and an antiviral agent, characterized by containing an organic pigment or an inorganic pigment and a fatty acid metal salt.

[0018] [2] The antibacterial agent and the antiviral agent according to [1], wherein the mass ratio of the organic pigment or the inorganic pigment to the fatty acid metal salt is the organic pigment or the inorganic pigment: fatty acid metal salt = 99:1 to 50:50.

[0019] [3] The antibacterial agent and the antiviral agent according to 1 or 2, wherein the organic pigment is at least one selected from iron phthalocyanine, copper phthalocyanine, soluble azo, insoluble azo, quinacridone, perylene, or diketopyrrolopyrrole.

[0020] [4] The antibacterial agent and the antiviral agent according to 1 or 2, wherein the inorganic pigment is at least one selected from iron(III) oxide or magnetite.

[0021] [5] The antibacterial and antiviral agent according to 1 or 2, characterized in that the fatty acid metal salt is represented by the following general formula (1).

[0022] [Chemical Formula 1]

[0023] (RCOO) n M (1)

[0024] (In the above general formula (1),

[0025] R is a hydrogen atom or a straight-chain alkyl group or a branched-chain alkyl group having 8 to 21 carbon atoms and may contain an alicyclic structure,

[0026] n is an integer in the range of 1 to 4. When n is an integer of 2 or more, the plurality of Rs may be the same as or different from each other.

[0027] M is lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or a rare earth.

[0028] [6] The antibacterial and antiviral agent according to [5], wherein the fatty acid metal salt is at least one selected from neodymium neodecanoate, lanthanum neodecanoate, and cobalt 2-ethylhexanoate.

[0029] [7] An ink, printed matter, coating, painting, plastic, fiber, film, and cosmetic, characterized by containing the antibacterial and antiviral agent according to any one of [1] to [6].

[0030] Advantages of the Invention

[0031] The antibacterial and antiviral agent of the present invention is water-insoluble, has antibacterial and antiviral effects, and has significantly higher performance in terms of heat resistance and light resistance compared to dye-based antibacterial pigments. In addition, it also has antibacterial and antiviral effects in applications such as inks, printed matters, coatings, paintings, plastics, fibers, films, and cosmetics, and can be used in a wide range of industrial fields.

[0032] Furthermore, the antibacterial and antiviral agent of the present invention exhibits the same pigment characteristics as conventional pigments, so it can be used in the same way as pigments, and coloring and imparting antibacterial and antiviral properties can be carried out simultaneously. Description of the Drawings

[0033] Figure 1 shows the SEM image of Composition 1.

[0034] Figure 2 is the result of elemental mapping based on SEM-EDS measurement performed at the same position and magnification as Figure 1 The white part indicates the distribution of neodymium. Detailed Description of the Invention

[0035] The embodiments of the present invention shown below only represent a part of the embodiments of the present invention, and are not limited to the described content as long as they do not deviate significantly from the gist.

[0036] Hereinafter, the antibacterial and antiviral agent of the present invention will be described.

[0037] [Organic Pigment]

[0038] ​​As the organic pigment used in the antibacterial agent and antiviral agent of the present invention, any well-known and commonly used substance can be used as long as it is a solid powder that is insoluble in water and in particulate form. For example, the following can be cited: phthalocyanine-based, quinacridone-based, perylene-based, diketopyrrolopyrrole-based, soluble azo-based, insoluble azo-based, anthraquinone-based, violanthrone-based, thioindigo-based, dioxazine-based, isoindolinone-based, isoindoline-based, quinophthalone-based pigments, etc. Phthalocyanine-based, quinacridone-based, perylene-based, diketopyrrolopyrrole-based, soluble azo-based, and insoluble azo-based are particularly preferred. These pigments can be used alone or in combination of two or more. When the organic pigment has high antibacterial and antiviral properties, the antibacterial agent and antiviral agent of the present invention exhibit particularly excellent antibacterial and antiviral effects and are preferred.

[0039] [Phthalocyanine]

[0040] The phthalocyanine used in the present invention is not particularly limited, and well-known and commonly used phthalocyanines can be used. The phthalocyanine used in the present invention is represented by the general formula (2).

[0041] [Chemical formula 2]

[0042]

[0043] (In the formula, M represents a metal such as Cu, Fe, Zn, Co, Na, Mg, Al, Si, Ca, Ti, V, Mn, Ni, Cd, Sn, or their metal oxides or metal halides, or metal-free. R1 to R16 each independently represent a hydrogen atom, a halogen atom, a carboxyl group, a hydroxyl group, a carbonyl group, an alkoxy group, or a sulfonyl group.)

[0044] For example, in the case of general pigments, when phthalocyanine is metal-free, C.I. Pigment Blue 16 can be cited. When the central metal of phthalocyanine is copper, C.I. Pigment Blue 15, C.I. Pigment Blue 15:1, C.I. Pigment Blue 15:2, C.I. Pigment Blue 15:3, C.I. Pigment Blue 15:4, C.I. Pigment Blue 15:6, C.I. Pigment Blue 76, C.I. Pigment Green 7, C.I. Pigment Green 36 can be cited. When the central metal of phthalocyanine is zinc, C.I. Pigment Green 58, C.I. Pigment Green 59 can be cited. When the central metal of phthalocyanine is cobalt, C.I. Pigment Blue 75 can be cited. When the central metal of phthalocyanine is aluminum, C.I. Pigment Blue 79 can be cited, etc.

[0045] In addition, the central metal of phthalocyanine is preferably copper, iron, zinc, cobalt, sodium, magnesium, aluminum, silicon, calcium, titanium, vanadium, manganese, nickel, cadmium, tin or metal-free phthalocyanine. These metals and phthalocyanine rings can be unsubstituted or have halogen substituents. As the number of substituents (n), theoretically n = 0 to 16, but in order to exhibit the function as a pigment, it is preferably to have substituents that are insoluble in water or solvents to a certain extent.

[0046] Among the above-mentioned metal phthalocyanines, when using phthalocyanines with high antibacterial and antiviral properties, they exhibit particularly high antibacterial and antiviral properties, so they are preferred. As the central metal of phthalocyanines with high antibacterial and antiviral properties, for example, iron, cobalt, sodium, magnesium, aluminum, silicon, manganese, nickel, cadmium, and tin can be cited.

[0047] Among them, phthalocyanines with iron, sodium, magnesium, or cobalt as the central metal are preferred because of their high antibacterial and antiviral effects. Furthermore, phthalocyanine with iron as the central metal is particularly preferred in the present invention.

[0048] [Quinacridone]

[0049] The quinacridone used in the present invention is not particularly limited, and known and commonly used quinacridones can be used. For example, it is represented by the general formula (3).

[0050] [Chemical formula 3]

[0051]

[0052] (In the formula, R1 to R16 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, or a nitro group.)

[0053] For example, C.I. Pigment Violet 19, C.I. Pigment Red 122, Pigment Red 202, Pigment Red 207, Pigment Red 206, Pigment Red 209, etc. can be cited. Among them, C.I. Pigment Violet 19 is preferred.

[0054] [Perylene]

[0055] The perylene used in the present invention is not particularly limited, and known and commonly used perylenes can be used. For example, it is represented by the general formula (4).

[0056] [Chemical formula 4]

[0057]

[0058] (In the formula, R1 and R2 each independently represent a hydrogen atom, an alkyl group, or an aryl group.)

[0059] For example, C.I. Pigment Red 123, C.I. Pigment Red 149, C.I. Pigment Red 179, C.I. Pigment Red 178, C.I. Pigment Violet 29, C.I. Pigment Black 31, etc. can be cited. Among them, C.I. Pigment Red 179 is preferred.

[0060] [Diketopyrrolopyrrole]

[0061] The diketopyrrolopyrrole used in the present invention is not particularly limited, and known and commonly used diketopyrrolopyrroles can be used. For example, it is represented by the general formula (5).

[0062] [Chemical formula 5]

[0063]

[0064] (In the formula, each of R1 to 10 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, or an amino group.)

[0065] For example, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 272, C.I. Pigment Orange 71, C.I. Pigment Orange 73, etc. may be cited. Among them, C.I. Pigment Red 254 is preferred.

[0066] [Soluble azo]

[0067] The soluble azo used in the present invention is not particularly limited, and a publicly known and commonly used soluble azo can be used. For example, it is represented by General Formulas (6) and (7).

[0068] [Chemical Formula 6]

[0069]

[0070]

[0071] (In the formula, each of R1 to 9 independently represents a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, a nitro group, etc. M represents barium, calcium, strontium, manganese, aluminum, or iron.)

[0072] [Chemical Formula 7]

[0073]

[0074] (In the formula, each of R1 to 10 independently represents a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, a nitro group, etc. M represents barium, calcium, strontium, manganese, aluminum, or iron.)

[0075] For example, C.I. Pigment Red 53:1, C.I. Pigment Red 53:2, C.I. Pigment Red 53:3, C.I. Pigment Red 49:1, C.I. Pigment Red 49:2, C.I. Pigment Red 49:3, C.I. Pigment Red 50:1, C.I. Pigment Red 57:1, C.I. Pigment Red 48:1, C.I. Pigment Red 48:2, C.I. Pigment Red 48:3, C.I. Pigment Red 48:4, C.I. Pigment Red 52:1, C.I. Pigment Red 63:1, C.I. Pigment Red 63:2, C.I. Pigment Red 64:1, C.I. Pigment Red 58:2, C.I. Pigment Red 58:4, C.I. Pigment Red 243, C.I. Pigment Red 61, C.I. Pigment Red 60:1, etc. may be cited. Among them, C.I. Pigment Red 48:1 is preferred.

[0076] [Insoluble azo]

[0077] Insoluble azo can be classified into β-naphthol series, naphthol AS series, pyrazolone series, acetoacetanilide series, benzimidazolone series, etc. The insoluble azo used in the present invention is not particularly limited, and publicly known and commonly used insoluble azo can be used. Among them, the acetoacetanilide series is preferred, and the bis-azo yellow series is further preferred. For example, the β-naphthol series is represented by the general formula (8).

[0078] [Chemical formula 8]

[0079]

[0080]

[0081] (In the formula, R1 to R10 each independently represent a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, or a nitro group.)

[0082] The naphthol AS series is represented by the general formula (9).

[0083] [Chemical formula 9]

[0084]

[0085] (In the formula, R1 to R15 each independently represent a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, or a nitro group.)

[0086] The pyrazolone series is represented by the general formula (10).

[0087] [Chemical formula 10]

[0088]

[0089] (In the formula, R1 to R9 each independently represent a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, or a nitro group.)

[0090] The acetoacetanilide series mono-azo type is represented by the general formula (11).

[0091] [Chemical formula 11]

[0092]

[0093] (In the formula, R1 to R10 each independently represent a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, or a nitro group.)

[0094] The acetoacetanilide series bis-azo type is represented by the general formula (12).

[0095] [Chemical formula 12]

[0096]

[0097] (In the formula, each of R1 to R8 independently represents a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, a nitro group, etc. Each of A and B independently represents an aryl group, etc. C represents -CnHn+2 (n is 0 or more), -O-CnHn+2-O- (n is 1 or more).)

[0098] The benzimidazolone series is represented by the general formula (13).

[0099] [Chemical formula 13]

[0100]

[0101] (In the formula, each of R1 to R13 independently represents a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, or a nitro group.)

[0102] For example, C.I. Pigment Red 3, C.I. Pigment Orange 5, C.I. Pigment Red 5, C.I. Pigment Red 146, C.I. Pigment Violet 50, C.I. Pigment Blue 25, C.I. Pigment Orange 13, C.I. Pigment Yellow 74, C.I. Pigment Yellow 12, C.I. Pigment Yellow 13, C.I. Pigment Yellow 14, C.I. Pigment Yellow 17, C.I. Pigment Yellow 55, C.I. Pigment Yellow 83, C.I. Pigment Yellow 180, C.I. Pigment Yellow 154, C.I. Pigment Red 185, etc. can be cited. Among them, C.I. Pigment Yellow 180 is preferred.

[0103] Phthalocyanine-based and condensed polycyclic-based pigments are mostly called crude pigments (crude pigments) in many cases. After manufacturing, they mostly have large particle sizes and particle non-uniformity, and have poor dispersibility depending on the application. Therefore, in order to make the particle size and crystal form into the desired particle size and crystal form, it is necessary to perform a further step of pigmentation as needed.

[0104] The various pigments used in the present invention exhibit crystalline properties rather than molecular properties through pigmentation. A band gap is generated by having crystalline properties, and the transfer of electrons for the reaction is carried out through the valence electron band and the conduction band. In the presence of multiple pigments, the movement of electrons required for the reaction, such as hopping conduction, can move between the pigments even in the presence of a resin, so that electrons can be injected and received by specific functional groups such as bacteria.

[0105] On the other hand, in the case of dyes, a decomposition reaction is carried out through a redox reaction, that is, a molecule jumps from the HOMO to the LUMO, or a specific atom contacts a specific functional group such as bacteria.

[0106] That is, the pigment has a crystalline nature, so that the antibacterial and antiviral effects are not only limited to the range in contact with the pigment, but can also extend to a range slightly away from the pigment. Specifically, in the case of dyes, the antibacterial property disappears when the dye is covered with resin in a coating film or the like, but in the case of pigments, even when the pigment is slightly covered with resin in a coating film or the like, the antibacterial and antiviral effects can be maintained.

[0107] For example, among the metal species of phthalocyanine, it is assumed that the metal species that are prone to oxidation-reduction of metal ions in an electrochemical reaction have higher antibacterial and antiviral properties than the metal species that are prone to oxidation-reduction of the phthalocyanine ring.

[0108] The pigment can be in the form of particles or needles, and there is no particular limitation on the shape. There is also no particular limitation on the particle size and aspect ratio. Generally, the micronized and refined pigment preferably has an average particle size of 20 to 300 nm and an aspect ratio of about 1 to 10, and more preferably an average particle size of 20 to 200 nm and an aspect ratio of about 1 to 5.

[0109] [Inorganic Pigment]

[0110] As the inorganic pigments used in the antibacterial and antiviral agents of the present invention, metal compounds such as titanium, zinc, lead, chromium, iron, cobalt, cadmium, copper, etc., high-carbon substances represented by carbon black, metal powders such as aluminum, copper, etc., and nanoparticles of gold, silver, etc. can be cited. There is no particular limitation, and publicly known and commonly used inorganic pigments can be used. In addition, when classified according to the use characteristics, it can be classified into extender pigments, white pigments, colored pigments, and pearlescent pigments, and they can be used without particular limitation. Examples of extender pigments include clay minerals and silica, examples of white pigments include titanium dioxide, and examples of colored pigments include pigments such as iron oxide, ultramarine, Prussian blue, and carbon black. Among the aforementioned inorganic pigments, iron oxide is particularly preferred. These pigments can be used alone or in combination of two or more.

[0111] The iron oxide used in the present invention is not particularly limited, and publicly known and commonly used iron oxide can be used. Black iron oxide refers to magnetite, expressed as Fe 3 O 4 (or FeOFe 2 O 3 ), red iron oxide refers to iron(III) oxide, expressed as Fe 2 O 3 , and yellow iron oxide refers to ferrous hydroxide, expressed as Fe 2 O 3 ·H 2 O (or FeOOH). Among the aforementioned iron oxides, black iron oxide and red iron oxide are particularly preferred.

[0112] For example, C.I. Pigment Black 11, C.I. Pigment Red 101, C.I. Pigment Red 102, C.I. Pigment Brown 6, C.I. Pigment Yellow 42, C.I. Pigment Yellow 43, etc. can be cited. Among them, C.I. Pigment Black 11 and C.I. Pigment Red 101 are preferred.

[0113] The pigments of the present invention can be used alone with organic pigments or inorganic pigments, or they can be used in combination.

[0114] [Fatty acid metal salt]

[0115] Regarding the fatty acid metal salts used in the antibacterial agents and antiviral agents of the present invention, as the metal types, they are lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or rare earths. Among them, in the present invention, neodymium, lanthanum, and cobalt have high antibacterial and antiviral effects and are preferred in the present invention.

[0116] The fatty acid metal salts used in the antibacterial agents and antiviral agents of the present invention are, for example, compounds represented by the following general formula (14).

[0117] [Chemical formula 14]

[0118] (RCOO) n M (14)

[0119] (In the above general formula (14),

[0120] R is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms,

[0121] n is an integer in the range of 1 to 4,

[0122] M is lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or rare earth.)

[0123] In the above general formula (14), when n is an integer of 2 or more, the plurality of Rs may be the same or different from each other.

[0124] The alkyl group having 1 to 21 carbon atoms of R may be a straight-chain alkyl group, a branched-chain alkyl group, or may contain an alicyclic structure.

[0125] The alkyl group having 1 to 21 carbon atoms in R corresponds to a carboxylic acid residue obtained by removing a carboxyl group (COOH) from a carboxylic acid having 2 to 22 carbon atoms represented by RCOOH used in the production of a fatty acid metal salt. Examples of such a carboxylic acid residue include an acetic acid residue, a propionic acid residue, a butyric acid residue, a valeric acid residue, an acrylic acid residue, a methacrylic acid residue, an octanoic acid residue (2-ethylhexanoic acid residue), a neodecanoic acid residue, a naphthenic acid residue, an isononanoic acid residue, an eleostearic acid residue, a tall oil fatty acid residue, a coconut oil fatty acid residue, a soybean oil fatty acid residue, a linseed oil fatty acid residue, a safflower oil fatty acid residue, a dehydrated castor oil fatty acid residue, a tung oil fatty acid residue, a lauric acid residue, a myristic acid residue, a palmitic acid residue, a stearic acid residue, an isostearic acid residue, an oleic acid residue, etc.

[0126] From the viewpoint of the substrate adhesion described later, the alkyl group having 1 to 21 carbon atoms in R is preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 11 carbon atoms, and still more preferably an acetic acid residue, a propionic acid residue, a butyric acid residue, a valeric acid residue, a 2-ethylhexanoic acid residue, an isononanoic acid residue, a neodecanoic acid residue, and a naphthenic acid residue.

[0127] M is lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum, or a rare earth element. It is preferably bismuth, neodymium, magnesium, cobalt, copper, silver, or zinc, and more preferably bismuth, neodymium, or magnesium.

[0128] If the metal of the fatty acid metal salt is bismuth, neodymium, or magnesium, it is possible to make coloring caused by the addition of an antibacterial agent or an antiviral agent difficult to occur.

[0129] It should be noted that in the present invention, the rare earth element refers to one or more selected from scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and lutetium (Lu).

[0130] n is a value determined by the valence of the metal atom of M. For example, if M is boron, n is 3, and if M is cobalt, n is 2.

[0131] The fatty acid metal salt as the antibacterial agent and antiviral agent of the present invention also includes a form of a fatty acid borate metal salt. This fatty acid borate metal salt is, for example, a compound represented by the following general formula (15).

[0132] [Chemical formula 15]

[0133] (RCOO-M-O) 3 B (15)

[0134] (In the above general formula (15),

[0135] R is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms,

[0136] M is boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or a rare earth.)

[0137] In the above general formula (15), the alkyl group having 1 to 21 carbon atoms of R is the same as the alkyl group having 1 to 21 carbon atoms of R in the above general formula (14). Similarly, in the above general formula (15), the metal of M is the same as the metal of M in the above general formula (14).

[0138] The fatty acid metal salt used in the antibacterial agent and antiviral agent of the present invention can be used alone or in combination of two or more kinds.

[0139] The fatty acid metal salt can be produced by a known method or a commercially available product can be used.

[0140] Regarding the fatty acid metal salt used in the antibacterial agent and antiviral agent of the present invention, neodymium neodecanoate, lanthanum neodecanoate, and cobalt 2-ethylhexanoate have high antibacterial and antiviral effects and are preferred in the present invention.

[0141] [Antibacterial agent, antiviral agent]

[0142] The antibacterial agent and antiviral agent of the present invention are a composition containing a pigment and a fatty acid metal salt, and can exist in any form of their respective attached forms or the form in which one is coated by the other. The form in which the surface of the pigment is coated with the fatty acid metal salt is particularly preferred.

[0143] The ratio of the pigment to the fatty acid metal salt in the antibacterial agent and antiviral agent of the present invention is pigment:fatty acid metal salt = 99:1 to 50:50 by mass ratio, preferably 98:2 to 60:40, and particularly preferably 95:5 to 70:30. From the viewpoints of antibacterial and antiviral properties, it is preferred that the ratio of the fatty acid metal salt is 1% or more in the antibacterial agent and antiviral agent. When the ratio of the fatty acid metal salt is 50% or less in the antibacterial agent and antiviral agent, it is preferred from the viewpoint of ease of treatment. Therefore, the ratio of the pigment to the fatty acid metal salt preferably satisfies the above range.

[0144] When the surface of the pigment is coated with the fatty acid metal salt, the ratio of pigment:fatty acid metal salt is preferably 99:1 to 50:50 by mass ratio, more preferably 98:2 to 60:40, and particularly preferably 95:5 to 70:30. The coating thickness of the fatty acid metal salt is preferably 1 to 10 nm. From the viewpoint of ease of operation, it is preferred to satisfy the above range.

[0145] In the present invention, "antibacterial" means including the effects of reducing the number of bacteria, inactivating bacteria, reducing the infectivity of bacteria, etc. Similarly, in the present invention, "antiviral" means including the effects of reducing the number of viruses, inactivating viruses, reducing the infectivity of viruses, etc.

[0146] The bacteria targeted for antibacterial in the present invention are not particularly limited and can be any one of bacteria and fungi. As bacteria, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Salmonella, Moraxella, Legionella, etc. can be mentioned; Gram-positive bacteria such as Staphylococcus aureus, Clostridium bacteria, etc. As fungi, yeasts such as Candida, Rhodotorula, baker's yeast, etc. can be mentioned; molds such as Penicillium, Aspergillus, etc.

[0147] The viruses targeted for antiviral in the present invention are not particularly limited and can be any one of known enveloped viruses (viruses with envelopes) and non-enveloped viruses (viruses without envelopes).

[0148] As the above-mentioned enveloped viruses, for example, coronavirus, influenza virus, rubella virus, Ebola virus, measles virus, varicella-zoster virus, herpes virus, mumps virus, arbovirus, RS virus, SARS virus, hepatitis virus (for example, hepatitis A virus, hepatitis B virus, hepatitis C virus, hepatitis D virus, hepatitis E virus, etc.), yellow fever virus, AIDS virus, rabies virus, hantavirus, dengue virus, Nipah virus, lyssavirus, etc. can be mentioned.

[0149] As the above-mentioned non-enveloped viruses, for example, adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, Coxsackievirus, human parvovirus, encephalomyocarditis virus, polyomavirus, BK virus, rhinovirus, feline calicivirus, etc. can be mentioned.

[0150] (Antibacterial effect)

[0151] As an index of antibacterial effect, bacterial proliferation tests using culture kits, etc., antibacterial tests specified in JIS standards, etc. can be mentioned.

[0152] Culture kits are mainly used to grasp the phenomenon of proliferation of general bacteria and fungi existing in nature such as food, air, and water due to the culture medium of the culture kit through the generation of colonies. However, by contacting a substance with antibacterial effect with the culture medium, a certain amount of bacteria and fungi are killed or the proliferation is inhibited, so that no colonies are generated or the generation of colonies is delayed. The bacterial proliferation test using a culture kit can be evaluated by regularly observing the above-mentioned phenomenon.

[0153] As the aforementioned general bacteria and fungi, for example, Escherichia coli, Staphylococcus aureus, Bacillus cereus, Salmonella, Pseudomonas aeruginosa, fungi, etc., or general live bacteria containing the aforementioned bacteria and fungi can be cited, but it is not limited to these.

[0154] As the culture kit, a general kit can be used. For example, the microbial simple measurement instrument San-ai BIO CHECKER (manufactured by San-ai Oil Co., Ltd.), the culture medium for bacterial count Compact Dry (manufactured by Nissui Pharmaceutical Co., Ltd.), etc. can be cited.

[0155] The antibacterial tests specified in the JIS standards mainly target representative Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Moraxella, and Gram-positive bacteria such as Staphylococcus aureus, MRSA, and Streptococcus pyogenes. Generally, the test bacterial solution is inoculated onto the sample, and under the state of making the aforementioned bacterial solution closely adhere to the membrane or glass, light irradiation is carried out for a certain period of time or it is left standing in the dark. Then, the recovered bacterial solution is diluted and cultured using an agar medium. After culturing, the antibacterial activity value is obtained by comparing the number of colonies produced. Specifically, the antibacterial test methods / antibacterial effects of JIS R1702 photocatalyst antibacterial processed products, the antibacterial test methods / antibacterial effects of JIS R1752 visible light-responsive photocatalyst processed products, the antibacterial test methods and antibacterial effects of JIS L1902 textile products, the antibacterial test methods / antibacterial effects of JIS Z2801 antibacterial processed products, or the bacterial solution absorption method, transfer method, bacterial transfer printing method, halo method, etc. specified in the antibacterial test methods and antibacterial effects of JIS L1902 textile products can be cited.

[0156] (Antiviral effect)

[0157] As the index of the antiviral effect, the antiviral tests specified in the JIS standards and ISO standards can be cited.

[0158] The antiviral tests specified in the JIS standard and the ISO standard are mainly based on representative enveloped influenza viruses, non-enveloped feline caliciviruses or bacteriophages. Generally, the virus liquid or bacteriophage liquid is inoculated into the sample, and the liquid is exposed to light for a certain period of time in a state in which the liquid is tightly bonded to a membrane or glass, or is left to stand in a dark place, and then the recovered liquid is diluted and cultured with an agar medium. After culture, the antiviral activity value is calculated by comparing the number of plaques. Alternatively, the virus liquid is inoculated into the sample, and the sample is exposed to light for a certain period of time in a state in which the sample is tightly bonded to a membrane or glass through the virus liquid, or is left to stand in a dark place, and then the virus liquid on the sample is rinsed and recovered, and the virus infectivity titer is compared to calculate the antiviral activity value. Specifically, antiviral tests such as JIS R1706 Antiviral test method for photocatalytic materials - method using bacteriophage Qβ, JIS R1756 Antiviral test method for visible light responsive photocatalytic materials - method using bacteriophage Qβ, ISO21702 Measurement of antiviral activity on plastics and other non-porous surfaces (measurement of viral activity on plastics or other non-porous surfaces), and JIS L1922 Antiviral test method for fiber products can be cited.

[0159] <Evaluation of antibacterial properties of coatings>

[0160] Antibacterial tests were conducted using Staphylococcus aureus (NBRC 12732) and Escherichia coli (NBRC 3972) as subjects by the following method.

[0161] 0.1 ml of the test bacterial solution was inoculated into a 5 cm x 5 cm coating film that had been cleaned by ultraviolet irradiation, and the solution was allowed to stand in a dark place for 8 or 24 hours while the solution was in close contact with the film or glass. The recovered bacterial solution was then diluted and cultured on an agar medium. After culture, the antimicrobial activity value was calculated by comparing the number of colonies produced. The calculation formula is R = (U t -U 0 )-(A t -U 0 )=U t -A t (R: antibacterial activity value, U 0 : The average value of the logarithmic value of the viable bacterial count immediately after inoculation in unprocessed products, U t : The average value of the logarithmic value of the viable bacterial count after 8 or 24 hours of the unprocessed product, A t: It is expressed by the average value of the logarithm of the viable cell count after 8 or 24 hours of the processed product. It should be noted that the processed product is a coating film formed by forming a film on a dispersion containing the test object, and the unprocessed product is a coating film formed by forming a film on a solution containing a PET film, synthetic resin, polyurethane resin, and solvent. As the standard of the antibacterial activity value, for example, in JIS Z2801:2021 Antibacterial Processed Products - Antibacterial Test Method / Antibacterial Effect, the judgment criterion for antibacterial effect is stipulated to be 2.0 or more. In addition, when the antibacterial activity value is 2.0, it means that compared with the unprocessed product, the processed product inhibits the proliferation of bacteria after the test by 99%. However, it does not necessarily mean that bacteria do not proliferate.

[0162] <Evaluation of Antiviral Activity of Coating Film>

[0163] Using bacteriophage Qβ (NBRC 20012, host Escherichia coli (NBRC 106373)), bacteriophage Φ6 (NBRC105899, host Pseudomonas syringae (NBRC 14084)), the antiviral test was carried out by the following method.

[0164] The test bacteriophage liquid was inoculated on a 5 cm × 5 cm coating film, and it was left standing in the dark for 4 hours in a state where the aforementioned bacteriophage liquid was in close contact with the film or glass. Then, the recovered bacteriophage liquid was diluted and cultured on an agar medium. After culturing, the antiviral activity value was obtained by comparing the number of colonies produced. The calculation formula is V D : Antiviral activity value (in the dark): [V D = Log(B D ) - Log(C D )](D: in the dark, B D : Infectivity titer of the unprocessed product after standing in the dark for 4 hours, C D : Infectivity titer of the processed product after standing in the dark for 4 hours). It should be noted that the processed product is a coating film formed by forming a film on a dispersion containing the test object, and the unprocessed product is a coating film formed by forming a film on a solution containing a PET film, synthetic resin, polyurethane resin, and solvent.

[0165] Here, for example, when the antiviral activity value is 2.0, it means that compared with the unprocessed product, the processed product inhibits the proliferation of bacteriophage after the test by 99%. However, it does not necessarily mean that bacteriophage does not proliferate.

[0166] By using the antibacterial agent and antiviral agent of the present invention, inks, printed matter, coatings, paintings, plastics, fibers, films, cosmetics, etc. can be provided. The uses described in detail below are for example, and the antibacterial agent and antiviral agent of the present invention can be used as applications with antibacterial, sterilizing, and antiviral properties for any use.

[0167] (Use of ink)

[0168] The antibacterial and antiviral agents of the present invention can provide printing inks with antibacterial and antiviral effects. The printing inks can be prepared by mixing various known and commonly used binder resins, various solvents, various additives, etc. in the antibacterial and antiviral agents of the present invention according to the conventional preparation methods. Specifically, by preparing a base ink for liquid ink with a high pigment concentration and using various binders, various solvents, various additives, etc., a liquid ink can be prepared.

[0169] The antibacterial and antiviral agents of the present invention can manufacture PU inks and NC inks with antibacterial and antiviral effects, and are suitable as organic compositions for gravure printing inks and flexographic printing inks. The PU ink is composed of a PU resin, a pigment, a solvent, and various additives, and the NC ink is composed of an NC resin, a pigment, a solvent, and various additives. The PU resin is not particularly limited as long as it has a urethane structure in the skeleton, and also includes polyurethanes, polyurethane polyureas, etc. As each solvent, aromatic organic solvents such as toluene and xylene, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone, ester solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, isobutyl acetate, propylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate, alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, and tert-butanol, (poly)alkylene glycol monoalkyl ether solvents such as propylene glycol monoethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-isopropyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, and diethylene glycol mono-isopropyl ether, (poly)alkylene glycol monoalkyl ether acetate solvents such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, and diethylene glycol monoethyl ether acetate, and other ether solvents such as diethylene glycol dimethyl ether and diethylene glycol diethyl ether, etc. It should be noted that the solvents can be used alone or in combination of two or more. As various additives, surfactants such as anionic, non-ionic, cationic, and zwitterionic surfactants, rosin such as gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleated rosin, cured rosin, and phthalic alkyd resin, pigment derivatives, dispersants, wetting agents, adhesion aids, leveling agents, defoaming agents, antistatic agents, scavengers, anti-blocking agents, wax components, etc. can be used.

[0170] When the antibacterial and antiviral agents of the present invention are used as printing inks, the printing inks using the antibacterial and antiviral agents of the present invention prepared as described above can be diluted with ethyl acetate, polyurethane-based varnishes, and polyamide-based varnishes for use. The preparation of the printing inks can adopt known and commonly used methods.

[0171] (Use of coatings)

[0172] When preparing the antibacterial and antiviral agents of the present invention into coatings with antibacterial and antiviral effects, various resins such as acrylic resin, melamine resin, epoxy resin, polyester resin, polyurethane resin, polyamide resin, phenolic resin, etc. can be used as the resins for coatings.

[0173] As the solvents used in coatings, there are aromatic solvents such as toluene, xylene, methoxybenzene, etc., acetate solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, etc., propionate solvents such as ethoxyethyl propionate, alcohol solvents such as methanol, ethanol, propanol, n-butanol, isobutanol, etc., ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, etc., ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc., aliphatic hydrocarbon solvents such as hexane, nitrogen compound solvents such as N,N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline, pyridine, etc., lactone solvents such as γ-butyrolactone, urethanes such as a 48:52 mixture of methyl carbamate and ethyl carbamate, water, etc. As solvents, propionate, alcohol, ether, ketone, nitrogen compound, lactone, and solvents soluble in polar solvents such as water are particularly suitable.

[0174] In addition, when preparing a resin composition for coatings by dispersing or mixing a pigment additive and / or an antibacterial and antiviral agent in a liquid resin, common additives such as dispersants, fillers, coating aids, driers, plasticizers, and / or auxiliary pigments can be used. This is achieved by dispersing or mixing each component alone, several components together, concentrating all the components, or adding them all at once.

[0175] As the disperser for dispersing the mixture containing antibacterial and antiviral agents prepared as described above according to the use, known dispersers such as dispersers, homogenizing mixers, coating regulators, Scandex, bead mills, grinders, ball mills, two-roll mills, three-roll mills, pressure kneaders, etc. can be cited, but are not limited to these. Regarding the dispersion of antibacterial and antiviral agents, resins and solvents are added for dispersion to achieve a viscosity that can be dispersed by these dispersers. The solid content of the high-concentration coating base after dispersion is 5% - 20%, and resins and solvents are further mixed therein for use as coatings.

[0176] (Plastic applications)

[0177] The antibacterial and antiviral agents of the present invention can also be used in plastic applications with antibacterial and antiviral effects. When obtaining a plastic molded article, thermoplastic resins (plastics) for thermoforming such as injection molding and compression molding, such as polyolefins like polyethylene and polypropylene, and polyvinyl chloride resins, are used. The antibacterial and antiviral agents of the present invention can be incorporated into these resins by conventionally known methods for use.

[0178] (Cosmetic applications)

[0179] The antibacterial and antiviral agents of the present invention can be used as cosmetics. The cosmetics used are not particularly limited, and the antibacterial and antiviral agents of the present invention can be used in various types of cosmetics.

[0180] The aforementioned cosmetics can be any type of cosmetics as long as they can effectively exhibit their functions. The aforementioned cosmetics can be skin lotions, cream gels, sprays, etc. Examples of the aforementioned cosmetics include skin care cosmetics such as facial cleansers, makeup removers, lotions, essences, masks, protective lotions, protective creams, whitening cosmetics, anti-UV cosmetics, etc., color cosmetics such as foundations, face powders, makeup primers, lipsticks, eye makeup, blushes, nail polishes, etc., hair care cosmetics such as shampoos, conditioners, hair treatments, hair styling agents, perming / coloring agents, hair growth agents, etc., body care cosmetics such as body cleansing cosmetics, deodorant cosmetics, bath agents, etc.

[0181] The antibacterial and antiviral agents of the present invention used in the aforementioned cosmetics can be appropriately set according to the type of cosmetics. The content in the aforementioned cosmetics is usually in the range of 0.1 to 99% by mass, and is usually preferably in the range of 0.1 to 10% by mass. On the other hand, in color cosmetics, it can be in the range of 5 to 80% by mass, 10 to 70% by mass, or 20 to 60% by mass. If the amount of the composition of the present invention contained in the aforementioned cosmetics is within the aforementioned range, functions such as colorability can be effectively exhibited, and the functions required for cosmetics can also be maintained.

[0182] In the aforementioned cosmetics, depending on the type of the cosmetics, in addition to the antibacterial agent and antiviral agent of the present invention, carriers, pigments, oils, sterols, amino acids, humectants, powders, colorants, pH adjusters, fragrances, essential oils, cosmetic active ingredients, vitamins, essential fatty acids, sphingolipids, self-tanning agents, excipients, fillers, emulsifiers, antioxidants, surfactants, chelating agents, gelling agents, thickeners, emollients, wetting agents, moisturizers, minerals, viscosity regulators, flow regulators, keratolytic agents, retinoids, hormone compounds, α-hydroxy acids, α-keto acids, anti-mycobacterial agents, antifungal agents, antibacterial agents, antiviral agents, analgesics, anti-allergy agents, antihistamines, anti-inflammatory agents, anti-irritants, anti-tumor agents, immune system boosters, immune system inhibitors, anti-acne agents, anesthetics, disinfectants, insect repellents, skin-cooling compounds, skin protectants, skin penetration enhancers, exfoliants, lubricants, fragrances, dyes, decolorants, hypopigmenting agents, preservatives, stabilizers, pharmaceuticals, light stabilizers, and spherical powders, etc. that are admissible as cosmetic ingredients may also be included.

[0183] The aforementioned cosmetics can be manufactured by mixing the antibacterial agent, antiviral agent of the present invention, and other cosmetic ingredients.

[0184] In addition, the cosmetics containing the antibacterial agent and antiviral agent of the present invention can be used in the same manner as ordinary cosmetics depending on the type of the cosmetics, etc.

[0185] When the antibacterial agent and antiviral agent of the present invention are used in coatings and plastics, the antibacterial agent and antiviral agent of the present invention are preferably present near the surface of the coating and the surface of the plastic. The above adjustment can be carried out by adjusting the type of the alkyl group of R in the fatty acid metal salt represented by the above formula (14) according to the type of the resin used in the coating and the plastic, or by controlling the dispersion conditions.

[0186] It is known that in the case of a composition in which the surface of a pigment is coated with a fatty acid metal salt in the antibacterial agent and antiviral agent of the present invention, the antibacterial and antiviral properties are particularly excellent. The reason is not yet certain, but it is speculated that when any one of the composition in which the surface of the pigment is coated with a fatty acid metal salt, the uncoated pigment, and the uncoated fatty acid metal salt is transferred to the vicinity of the surface of the coating film and the plastic, the remaining components are also likely to be transferred to the vicinity of the surface together.

[0187] Examples

[0188] Hereinafter, examples are listed to further detail the present invention, but the present invention is not limited to these examples. In addition, "%" in the compositions of the following examples means "mass %".

[0189] The pigments used in Examples 1 to 15 and Comparative Examples 1 to 13 are described below.

[0190] (Iron phthalocyanine)

[0191] The iron phthalocyanine used had the product name: P-26 (manufactured by Sanyo Shikiso Co., Ltd.).

[0192] (Copper phthalocyanine)

[0193] The copper phthalocyanine used was C.I. Pigment Blue 15:3, with the product name: FASTOGEN BLUE PA5380 (manufactured by DIC Corporation).

[0194] (Zinc bromochloride phthalocyanine)

[0195] The zinc bromochloride phthalocyanine used was C.I. Pigment Green 58, with the product name: FASTOGEN GREEN A110 (manufactured by DIC Corporation).

[0196] (Quinacridone)

[0197] The quinacridone used was C.I. Pigment Violet 19, with the product name: FASTOGEN SUPER RED 7061BCONC (manufactured by DIC Corporation).

[0198] (Perylene)

[0199] The perylene used was C.I. Pigment Red 179, with the product name: PERRINDO MAROON 179 229-6438 (manufactured by DIC Corporation).

[0200] (Diketopyrrolopyrrole)

[0201] The diketopyrrolopyrrole used was C.I. Pigment Red 254, with the product name: FASTOGEN SUPER RED 254 226-0200 (manufactured by DIC Corporation).

[0202] (Azo barium salt)

[0203] The azo barium salt used was C.I. Pigment Red 48:1, with the product name: SYMULER RED 3109 (manufactured by DIC Corporation).

[0204] (Bisazo)

[0205] The bisazo used was C.I. Pigment Yellow 180, with the product name: SYMULER Light Fast Yellow BY2000 GT (manufactured by DIC Corporation).

[0206] (Black iron oxide)

[0207] Black iron oxide uses C.I. Pigment Black 11, product name: C33-134 Sun CROMA Black Iron Oxide (manufactured by Sun Chemical).

[0208] (Red iron oxide)

[0209] Red iron oxide uses C.I. Pigment Red 101, product name: C33-128 SunCROMA Red Iron Oxide (manufactured by Sun Chemical).

[0210] Hereinafter, the preparation methods of the fatty acid metal salts used in Examples 1 to 15 and Comparative Examples 1 to 13 are described.

[0211] (Preparation of neodymium neodecanoate)

[0212] Put 224.8 g of neodecanoic acid (manufactured by Fujifilm Wako Pure Chemical Corporation) and 60.0 g of neodymium oxide (manufactured by Kanto Chemical Co., Inc.) into a 1.0 L separable flask, react at 130 °C, and then use a suction pump to dehydrate under reduced pressure at 0.08 bar and 130 °C for 2 hours to obtain neodymium neodecanoate. The obtained neodymium neodecanoate is a light purple and highly viscous adhesive solid.

[0213] (Preparation of lanthanum neodecanoate solution)

[0214] React 83.1 g of neodecanoic acid (manufactured by Fujifilm Wako Pure Chemical Corporation) with 21.5 g of lanthanum oxide (manufactured by Kanto Chemical Co., Inc.) at 130 °C, dehydrate under reduced pressure at 130 °C, and then add 107.6 g of cyclohexane to obtain 208.5 g of lanthanum neodecanoate solution. The lanthanum content in the obtained lanthanum neodecanoate solution is 8.8 mass%.

[0215] (Preparation of cobalt 2-ethylhexanoate solution)

[0216] React 319.0 g of 2-ethylhexanoic acid (manufactured by Kanto Chemical Co., Inc.) with 100.0 g of cobalt hydroxide (manufactured by Fujifilm Wako Pure Chemical Corporation) at 130 °C, dehydrate under reduced pressure at 130 °C, and then add 134.2 g of petroleum-based hydrocarbon to obtain 502.3 g of cobalt 2-ethylhexanoate solution. The cobalt content in the obtained cobalt 2-ethylhexanoate solution is 12 mass%.

[0217] The substances obtained by distilling off the solvent from the neodymium neodecanoate and lanthanum neodecanoate solutions obtained from the above preparations and the substances obtained by distilling off the solvent from the cobalt 2-ethylhexanoate solution are soluble in isobutanol, methyl ethyl ketone, and toluene, but insoluble in acetone and propylene glycol monomethyl ether acetate. Regarding solubility, 0.1 g of the substance obtained by distilling off the solvent from the neodymium neodecanoate or lanthanum neodecanoate solution or the substance obtained by distilling off the solvent from the cobalt 2-ethylhexanoate solution and 2.0 g of the solvent were added to a screw vial (13.5 mL) and mixed. After standing for a while, if there was no solid residue and the solution was transparent, it was considered "soluble", and if there was a solid residue or the solution was cloudy, it was considered "insoluble".

[0218] Hereinafter, the preparation methods of the compositions used in Examples 1 to 15 are described. The amounts of the pigments and fatty acid metal salts used in the preparation of the compositions are shown in Table 1.

[0219] [Table 1]

[0220]

[0221] (Preparation of Composition 1)

[0222] 5.0 g of neodymium neodecanoate and 60.0 g of isobutanol (manufactured by Kanto Chemical Co., Inc.) were mixed and stirred in a 0.5 L separable flask. Then, 20.0 g of iron phthalocyanine and 120.0 g of water were added, and the mixture was refluxed with stirring for 1 hour. Then, 120.0 g of water was added, the solvent was distilled off, and then filtration, washing, drying, and pulverization were performed to obtain Composition 1.

[0223] (Preparation of Compositions 2, 5 to 15)

[0224] The fatty acid metal salt and 30.0 g of isobutanol (manufactured by Kanto Chemical Co., Inc.) were mixed and stirred in a 0.5 L separable flask. Then, the pigment and 60.0 g of water were added, and the mixture was refluxed with stirring for 1 hour. Then, 60.0 g of water was added, the solvent was distilled off, and then filtration, washing, drying, and pulverization were performed to obtain the composition.

[0225] (Compositions 3, 4)

[0226] Using a 50 mL eggplant-shaped flask, the solvent was distilled off from the fatty acid metal salt, 30.0 g of isobutanol (manufactured by Kanto Chemical Co., Inc.) was added, and the mixture was transferred to a 0.5 L separable flask. Then, the pigment and 60.0 g of water were added, and the mixture was refluxed with stirring for 1 hour. Then, 60.0 g of water was added, the solvent was distilled off, and then filtration, washing, drying, and pulverization were performed to obtain the composition.

[0227] Element mapping using SEM-EDS was performed on the obtained compositions 1 to 15. As a result, particle images and elements corresponding to the metal species of the fatty acid metal salt were detected at the same site in Compositions 1 to 15, and it was speculated that the fatty acid metal salt adhered to or coated the surface of the pigment. It should be noted that for SEM-EDS, platinum evaporation was performed on the obtained composition, and measurement was carried out using a scanning electron microscope (SEM, product name: JSM-IT200(LA) (manufactured by JEOL Ltd.)) equipped with an energy dispersive X-ray analyzer (EDS). The measurement conditions were set as an operating distance (WD) of 10 mm, an acceleration voltage of 15.0 or 20.0 kV, and a field of view of 1000 to 5000 times magnification was used as the object.

[0228] For example, the SEM-EDS results of Composition 1 are shown in Figure 1 , Figure 2 . Figure 1 represents the SEM image of Composition 1, Figure 2 represents the result of element mapping based on SEM-EDS measurement performed at the same position and magnification as Figure 1 . The white part represents the distribution of neodymium. Since particle images and neodymium were detected at the same position, it can be speculated that the fatty acid metal salt adhered to or covered the surface of iron phthalocyanine.

[0229] Hereinafter, the method for producing the coating film used in the antibacterial test and the antiviral test is described.

[0230] In the production of the coating film, the following resins were used.

[0231] Resin 1: Synthetic resin (product name: V343-306SA (manufactured by DIC Graphics Co., Ltd., solid content concentration: 25%, weight ratio of solvents: methyl ethyl ketone / ethyl acetate / toluene = 35 / 20 / 20)

[0232] Resin 2: A substance obtained by distilling off the solvent component of the synthetic resin (product name: V343-306SA (manufactured by DIC Graphics Co., Ltd., solid content concentration: 25%, weight ratio of solvents: methyl ethyl ketone / ethyl acetate / toluene = 35 / 20 / 20))

[0233] Resin 3: Polyurethane resin (product name: Sanprene IB-D12 (manufactured by Sanyo Chemical Industries, Ltd., solid content concentration: 30%, weight ratio of solvents: methyl ethyl ketone / isopropyl alcohol = 47 / 23)

[0234] Resin 4: A substance obtained by distilling off the solvent components of a polyurethane resin (product name: Sanprene IB-D12 (manufactured by Sanyo Chemical Industries, Ltd., solid component concentration: 30%, weight ratio of solvents: methyl ethyl ketone / isopropyl alcohol = 47 / 23)).

[0235] In the production of the coating film, acetone (manufactured by Kanto Chemical Co., Inc.) and propylene glycol monomethyl ether acetate (hereinafter referred to as PGMEA, manufactured by Kanto Chemical Co., Inc.), or methyl ethyl ketone (hereinafter referred to as MEK, manufactured by Kanto Chemical Co., Inc.) and toluene (manufactured by Kanto Chemical Co., Inc.) are used as solvents.

[0236] The formulations used in the production of the coating films of Examples 1 to 15 and Comparative Examples 1 to 13 are shown in Tables 2 and 3. In Examples 1 to 15, the coating films were produced using the formulations in Table 2 for the compositions obtained in the preparation of the compositions, and in Comparative Examples 1 to 13, the pigments or fatty acid metal salts were mixed separately using the formulations in Table 3 to produce the coating films. The addition amount refers to the weight ratio of the composition or pigment or fatty acid metal salt contained relative to the resin solid components in the coating film.

[0237] [Table 2]

[0238]

[0239] [Table 3]

[0240]

[0241] (Examples 1 to 15)

[0242] Using the formulations in Table 2, the respective coating films were obtained by the following method.

[0243] An antibacterial agent, an antiviral agent, a resin, a solvent, and 80 g of 1 / 8-inch steel balls were placed in a plastic bottle and shaken for 30 minutes using a paint conditioner to obtain a dispersion.

[0244] The obtained dispersion was coated on a 188-μm PET film using a bar coater No. 6, dried using a dryer, and further dried at 150°C for 15 minutes to obtain the coating films of Examples 1 to 15.

[0245] (Comparative Examples 1 to 13)

[0246] Using the formulations in Table 3, the respective coating films were obtained by the following method.

[0247] A pigment or a fatty acid metal salt, a resin, a solvent, and 80 g of 1 / 8-inch steel balls were placed in a plastic bottle and shaken for 30 minutes using a paint conditioner to obtain a dispersion.

[0248] The obtained dispersion was coated on a 188-μm PET film using a rod coater No. 6, dried in a dryer, and further dried at 150 °C for 15 minutes to obtain the coating films of Comparative Examples 1 to 13.

[0249] <Antibacterial Test 1>

[0250] With reference to JIS R 1752:2020, an antibacterial test was carried out on Escherichia coli (NBRC3972) by the following method.

[0251] 0.1 ml of the test bacterial solution was inoculated into a 5 cm × 5 cm coating film that had been cleaned by ultraviolet irradiation, and the mixture was allowed to stand in the dark for 24 hours with the bacterial solution in close contact with the film or glass. Then, the recovered bacterial solution was diluted and cultured on an agar medium. After culturing, the antibacterial activity value was determined by comparing the number of colonies formed. The calculation formula is R = (Ut - U0) - (At - U0) = Ut - At (R: antibacterial activity value, U0: average value of the logarithm of the viable cell count immediately after inoculation of the non-processed product, Ut: average value of the logarithm of the viable cell count after 24 hours of the non-processed product, At: average value of the logarithm of the viable cell count after 24 hours of the processed product). It should be noted that the processed product is a coating film formed by forming a film from a dispersion containing the test object, and the non-processed product is a PET film.

[0252] <Antibacterial Test 2>

[0253] Using Staphylococcus aureus (NBRC12732) instead of Escherichia coli (NBRC3972), the antibacterial test was carried out in the same manner as in <Antibacterial Test 1> except for this.

[0254] <Antibacterial Test 3>

[0255] With reference to JIS R1752:2020, an antibacterial test was carried out on Escherichia coli (NBRC3972) by the following method.

[0256] In a 5 cm × 5 cm coating film that has been cleaned by ultraviolet irradiation, 0.1 ml of a test bacterial solution is inoculated, and the bacterial solution is allowed to stand in the dark for 8 hours in a state where it is in close contact with the film or glass. Then, the recovered bacterial solution is diluted and cultured on an agar medium. After culturing, the antibacterial activity value is determined by comparing the number of colonies formed. The calculation formula is represented by R = (Ut - U0) - (At - U0) = Ut - At (R: antibacterial activity value, U0: average value of the logarithm of the viable bacteria count immediately after inoculation of the non-processed product, Ut: average value of the logarithm of the viable bacteria count after 8 hours of the non-processed product, At: average value of the logarithm of the viable bacteria count after 8 hours of the processed product). It should be noted that the processed product is a coating film formed by film-forming a dispersion containing the test object, and the non-processed product is a coating film formed by film-forming a solution containing a synthetic resin, a polyurethane resin, and a solvent).

[0257] <Antibacterial Test 4>

[0258] Using Staphylococcus aureus (NBRC12732) instead of Escherichia coli (NBRC3972), the antibacterial test was carried out in the same manner as in <Antibacterial Test 3> except for this.

[0259] <Antiviral Test 1>

[0260] Referring to JIS R1756:2020, the antiviral test was carried out on bacteriophage Qβ (NBRC20012, host Escherichia coli (NBRC106373)) by the following method.

[0261] On a 5 cm × 5 cm coating film, a test bacteriophage solution is inoculated, and the bacteriophage solution is allowed to stand in the dark for 4 hours in a state where it is in close contact with the film or glass. Then, the recovered bacteriophage solution is diluted and cultured on an agar medium. After culturing, the antiviral activity value is determined by comparing the number of colonies formed. The calculation formula is represented by VD: antiviral activity value (in the dark): [VD = Log(BD) - Log(CD)] (D: in the dark, BD: infectious titer of the non-processed product after standing in the dark for 4 hours, CD: infectious titer of the processed product after standing in the dark for 4 hours). It should be noted that the processed product is a coating film formed by film-forming a dispersion containing the test object, and the non-processed product is a PET film).

[0262] <Antiviral Test 2>

[0263] Referring to JIS R1756:2020, the antiviral test was carried out on bacteriophage Qβ (NBRC20012, host Escherichia coli (NBRC106373)) by the following method.

[0264] Inoculate a test phage solution on a coating film of 5 cm × 5 cm, and leave it standing in the dark for 4 hours in a state where the aforementioned phage solution is in close contact with the film or glass. Then, dilute the recovered phage solution and culture it using an agar medium. After culturing, the antiviral activity value is determined by comparing the number of colonies formed. The calculation formula is represented by VD: antiviral activity value (in the dark): [VD = Log(BD) - Log(CD)] (D: in the dark, BD: infectious titer of the non-processed product after standing in the dark for 4 hours, CD: infectious titer of the processed product after standing in the dark for 4 hours). It should be noted that the processed product is a coating film formed by forming a dispersion containing the test object into a film, and the non-processed product is a coating film formed by forming a solution containing a synthetic resin, a polyurethane resin, and a solvent into a film).

[0265] <Antiviral Test 3>

[0266] Use phage Φ6 (NBRC105899, host Pseudomonas syringae (NBRC14084)) instead of phage Qβ (NBRC20012, host Escherichia coli (NBRC106373)), and perform the antiviral test in the same manner as <Antiviral Test 2> except for this.

[0267] Perform <Antibacterial Test 1> on the coating films of Example 1, Comparative Examples 1 and 2. The results are shown in Table 4.

[0268] [Table 4]

[0269] Antibacterial agent Activity value Example 1 Composition 1 2.3 Comparative Example 1 Iron phthalocyanine 0.4 Comparative Example 2 Neodymium neodecanoate 1.2

[0270] Perform <Antibacterial Test 2> on the coating films of Example 1, Comparative Examples 1 and 2. The results are shown in Table 5.

[0271] [Table 5]

[0272] Antibacterial agent Activity value Example 1 Composition 1 1.9 Comparative Example 1 Iron phthalocyanine 1.0 Comparative Example 2 Neodymium neodecanoate 0.3

[0273] Perform <Antibacterial Test 3> on Examples 3, 5 to 10, 12, 13 and Comparative Examples 5 to 10, 12, 13. The results are shown in Table 6.

[0274] [Table 6]

[0275] Antibacterial agent Activity value Example 3 Composition 3 1.3 Example 5 Composition 5 1.0 Example 6 Composition 6 1.0 Example 7 Composition 7 0.7 Example 8 Composition 8 0.8 Example 9 Composition 9 1.1 Example 10 Composition 10 0.9 Example 12 Composition 12 0.9 Example 13 Composition 13 1.0 Comparative Example 5 Copper phthalocyanine 0.2 Comparative Example 6 Zinc phthalocyanine bromide chloride -0.2 Comparative Example 7 Quinacridone 0.1 Comparative Example 8 Perylene 0.1 Comparative Example 9 Diketopyrrolopyrrole -0.1 Comparative Example 10 Bisazo 0.1 Comparative Example 12 Black iron oxide 0.1 Comparative Example 13 Red iron oxide 0.4

[0276] Perform <Antibacterial Test 4> on Examples 2, 4 to 15 and Comparative Examples 3 to 13. The results are shown in Table 7.

[0277] [Table 7]

[0278] Antibacterial agent Activity value Example 2 Composition 2 4.4 Example 4 Composition 4 2.5 Example 5 Composition 5 2.1 Example 6 Composition 6 3.5 Example 7 Composition 7 1.7 Example 8 Composition 8 1.9 Example 9 Composition 9 -0.6 Example 10 Composition 10 2.3 Example 11 Composition 11 2.6 Example 12 Composition 12 3.5 Example 13 Composition 13 3.5 Example 14 Composition 14 3.2 Example 15 Composition 15 3.5 Comparative Example 3 Iron phthalocyanine 2.2 Comparative Example 4 Iron phthalocyanine / neodymium neodecanoate 4.4 Comparative Example 5 Copper phthalocyanine 0.7 Comparative Example 6 Zinc phthalocyanine bromide chloride -0.2 Comparative Example 7 Quinacridone 0.3 Comparative Example 8 Perylene 0.2 Comparative Example 9 Diketopyrrolopyrrole -0.1 Comparative Example 10 Bisazo 0.3 Comparative Example 11 Barium azo salt 1.7 Comparative Example 12 Black iron oxide 1.7 Comparative Example 13 Red iron oxide 1.8

[0279] Perform <Antiviral Test 1> on the coating films of Example 1, Comparative Examples 1 and 2. The results are shown in Table 8.

[0280] [Table 8]

[0281] Antiviral agent Activity value Example 1 Composition 1 0.6 Comparative Example 1 Iron phthalocyanine 0.1 Comparative Example 2 Neodymium neodecanoate 0.3

[0282] Perform <Antiviral Test 2> on the coating films of Example 2, Examples 3, 5 to 10, Examples 12 to 13, Comparative Examples 3 to 10, Comparative Example 12 and Comparative Example 13. The results are shown in Table 9.

[0283] [Table 9]

[0284] Antiviral agent Activity value Example 2 Composition 2 2.3 Example 3 Composition 3 1.9 Example 5 Composition 5 0.9 Example 6 Composition 6 0.8 Example 7 Composition 7 0.8 Example 8 Composition 8 0.8 Example 9 Composition 9 0.9 Example 10 Composition 10 0.9 Example 12 Composition 12 1.1 Example 13 Composition 13 1.o Comparative Example 3 Iron phthalocyanine 0.1 Comparative Example 4 Iron phthalocyanine / neodymium neodecanoate 1.3 Comparative Example 5 Copper phthalocyanine 0.3 Comparative Example 6 Zinc phthalocyanine bromide chloride 0.0 Comparative Example 7 Quinacridone -0.1 Comparative Example 8 Perylene 0.0 Comparative Example 9 Diketopyrrolopyrrole -0.1 Comparative Example 10 Bisazo 0.1 Comparative Example 12 Black iron oxide 0.0 Comparative Example 13 Red iron oxide 1.2

[0285] Perform <Antiviral Test 3> on the coating films of Examples 2 to 11, Examples 14 to 15, and Comparative Examples 3 to 11. The results are shown in Table 10.

[0286] [Table 10]

[0287] Antiviral agent Activity value Example 2 Composition 2 5.0 Example 3 Composition 3 2.0 Example 4 Composition 4 3.3 Example 5 Composition 5 1.7 Example 6 Composition 6 1.6 Example 7 Composition 7 1.6 Example 8 Composition 8 1.6 Example 9 Composition 9 1.5 Example 10 Composition 10 1.6 Example 11 Composition 11 1.6 Example 14 Composition 14 1.8 Example 15 Composition 15 1.9 Comparative Example 3 Iron phthalocyanine 2.0 Comparative Example 4 Iron phthalocyanine / neodymium neodecanoate 3.0 Comparative Example 5 Copper phthalocyanine 0.2 Comparative Example 6 Zinc phthalocyanine bromide chloride -0.2 Comparative Example 7 Quinacridone -0.1 Comparative Example 8 Perylene 0.6 Comparative Example 9 Diketopyrrolopyrrole 0.0 Comparative Example 10 Bisazo 0.1 Comparative Example 11 Barium azo salt 0.3

[0288] From the results in Tables 4, 5 and 8, it can be seen that compared with the coating films of Comparative Examples 1 and 2, the coating film of Example 1 shows excellent antibacterial and antiviral properties.

[0289] From the results in Tables 7, 9 and 10, it can be seen that compared with the coating films of Comparative Examples 3 and 4, the coating film of Example 2 shows excellent antibacterial and antiviral properties. When comparing Example 2 with Comparative Example 4, it was found that when using the composition obtained through the preparation of the composition to make the coating film, higher antibacterial and antiviral properties are exhibited compared with simply mixing the pigment and the fatty acid metal salt during the production of the coating film.

[0290] From the results of Examples 1 to 4 and Comparative Examples 1 to 4 in Tables 4, 5 to 10, it can be seen that the compositions using various fatty acid metal salts show excellent antibacterial and antiviral properties. Therefore, it can be said that various fatty acid metal salts can be used as the fatty acid metal salts constituting the antibacterial agent and antiviral agent of the present invention.

[0291] From the results of Examples 5 to 11 and Comparative Examples 5 to 11 in Tables 6, 7, 9 and 10, it can be seen that by preparing the composition, the antibacterial activity and antiviral activity of organic pigments that do not have antibacterial and antiviral properties can be improved. Therefore, it can be said that various organic pigments can be used as the pigments constituting the antibacterial agent and antiviral agent of the present invention.

[0292] As can be seen from the results of Examples 12 and 13 and Comparative Examples 12 and 13 in Tables 6, 7, and 9, the antibacterial and antiviral activities of inorganic pigments that do not have antibacterial and antiviral properties are improved by preparing the composition. Therefore, it can be said that various inorganic pigments can be used as the pigments constituting the antibacterial agent and antiviral agent of the present invention.

[0293] As can be seen from the results of Examples 2, 14, and 15 in Tables 7 and 10, all have high antibacterial and antiviral properties. However, as the proportion of neodymium neodecanoate relative to iron phthalocyanine increases, the antibacterial and antiviral properties slightly decrease. It is considered that this is because neodymium neodecanoate is a sticky solid, so as the proportion of neodymium neodecanoate relative to iron phthalocyanine increases, the aggregation of the composition becomes larger, and the composition is not uniformly dispersed in the coating film, resulting in a decrease in antibacterial and antiviral properties.

Claims

1. An antibacterial and antiviral agent, characterized in that, it contains an organic pigment or an inorganic pigment and a fatty acid metal salt.

2. The antibacterial and antiviral agent according to claim 1, wherein, the mass ratio of the organic pigment or inorganic pigment to the fatty acid metal salt is the organic pigment or inorganic pigment: fatty acid metal salt = 99:1 to 50:

50.

3. The antibacterial and antiviral agent according to claim 1 or 2, wherein, the organic pigment is at least one selected from iron phthalocyanine, copper phthalocyanine, soluble azo, insoluble azo, quinacridone, perylene or diketopyrrolopyrrole.

4. The antibacterial and antiviral agent according to claim 1 or 2, wherein, the inorganic pigment is at least one selected from iron(III) oxide or magnetite.

5. The antibacterial and antiviral agent according to claim 1 or 2, characterized in that, the fatty acid metal salt is represented by the following general formula (1), [Chemical formula 1] (RCOO) n M (1) In the general formula (1), R is a hydrogen atom or a straight-chain alkyl group or a branched alkyl group having 8 to 21 carbon atoms and may contain an alicyclic structure, n is an integer in the range of 1 to 4. When n is an integer of 2 or more, multiple Rs may be the same or different from each other, M is lithium, sodium, potassium, rubidium, cesium, boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, silver, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or rare earth.

6. The antibacterial and antiviral agent according to claim 5, wherein, the fatty acid metal salt is at least one selected from neodymium neodecanoate, lanthanum neodecanoate, cobalt 2-ethylhexanoate.

7. An ink, printed matter, coating, painting, plastic, fiber, film and cosmetic, characterized in that, it contains the antibacterial and antiviral agent according to claim 1 or 2.

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