Antibacterial and antiviral agents

Abstract

The present invention addresses the problem of providing: an antibacterial agent and an antiviral agent which are characterized by containing a pigment and a fatty acid metal salt; and an ink, a printed object, a paint, a coating, a plastic, a fiber, a film, and a cosmetic, etc., which are characterized by containing the antibacterial agent and the antiviral agent. An antibacterial agent and an antiviral agent according to the present invention contain a pigment and a fatty acid metal, and were discovered to have an antibacterial and antiviral action. A molded article containing the antibacterial agent and the antiviral agent were likewise discovered to have an antibacterial and antiviral action. The discovery successfully solved the above-mentioned problem.

Description

[Technical field]

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

[0002] In recent years, there has been a strong demand to maintain the cleanliness of living spaces, and air purifiers and disinfectant sprays have been installed in many homes and public rooms to maintain a clean environment, but efforts are also being made to add high added value by imparting antibacterial, antiviral, allergen removal, and deodorizing functions beyond the simple air purification function of removing dirt and dust from the air. Examples of applications requiring such high added value include fiber applications, plastic applications, and paint applications.

[0003] In fiber applications, methods for imparting antibacterial or antiviral properties include a method of kneading an antibacterial or antiviral agent into fibers and a method of adhering a solution containing an antibacterial or antiviral agent to the fiber surface. In the case of the method of kneading an antibacterial or antiviral agent into fibers, it is generally considered that the washing durability is high, but since the temperature is high during spinning, there is a concern that the organic antibacterial or antiviral agent may be thermally decomposed, and improvement of heat resistance has been desired. On the other hand, in the case of the method of adhering to the fiber surface, an organic antibacterial or antiviral agent, such as a quaternary ammonium salt, is generally used, but there is a problem that the antibacterial or antiviral properties decrease by washing (Patent Document 1).

[0004] In paint applications, organic antibacterial or antiviral agents are used, as in fiber applications. However, acrylic / melamine paints and the like require a curing process by heat treatment, and organic antibacterial or antiviral agents that are considered to have low heat resistance may cause thermal deterioration of the treated surface and object (Patent Document 2). From this perspective, there has been a demand for improved heat resistance in applications where treatment is performed at high temperatures.

[0005] Regarding the content of the antibacterial or antiviral agent, it is necessary for the agent to be effective in a relatively small amount in any application, and therefore, a technically important issue is how to efficiently expose the antibacterial or antiviral agent on the surface of fibers, plastics, coatings, etc. (Patent Documents 3 and 4). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2013-76188 A [Patent Document 2] JP 2017-014401 A [Patent Document 3] JP 2006-28453 A [Patent Document 4] Patent Publication No. 2022-93225 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present invention is to provide an antibacterial agent, an antiviral agent, and an ink, a printed matter, a paint, a coating, a plastic, a fiber, a film, a cosmetic, and the like, which are characterized by containing the antibacterial agent or the antiviral agent. [Means for solving the problem]

[0008] As a result of intensive research into solving the above-mentioned problems, the inventors have found that an antibacterial agent and an antiviral agent containing a pigment and a fatty acid metal salt have antibacterial and antiviral effects, and that a molded product containing the antibacterial agent and antiviral agent also has antibacterial and antiviral effects, thereby solving the above-mentioned problems.

[0009] That is, the present invention includes the following.

[0010] [1] An antibacterial or antiviral agent comprising an organic or inorganic pigment and a fatty acid metal salt. [2] The antibacterial agent or antiviral agent according to [1], wherein the mass ratio of the organic pigment or inorganic pigment to the fatty acid metal salt is from 99:1 to 50:50. [3] The antibacterial and antiviral agent according to 1 or 2, wherein the organic pigment is at least one selected from the group consisting of iron phthalocyanine, copper phthalocyanine, soluble azo, insoluble azo, quinacridone, perylene, and diketopyrrolopyrrole. [4] The antibacterial and antiviral agent according to 1 or 2, wherein the inorganic pigment is at least one of iron oxide (III) and triiron tetroxide. [5] The fatty acid metal salt is represented by the following general formula (1):

[0011] [ka]

[0012] (In the general formula (1), R is a hydrogen atom or a linear or branched alkyl group having 8 to 21 carbon atoms which may contain an alicyclic structure, n is an integer ranging from 1 to 4, and when n is an integer of 2 or more, multiple R's may be the same or different. 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. [6] The antibacterial and antiviral agent according to 1 or 2, characterized in that the fatty acid metal salt is at least one selected from the group consisting of neodymium neodecanoate, lanthanum neodecanoate, and cobalt 2-ethylhexanoate. [7] An ink, a printed matter, a paint, a coating, a plastic, a fiber, a film, or a cosmetic, characterized by containing the antibacterial agent or antiviral agent according to any one of 1 to 6. Effect of the Invention

[0013] The antibacterial and antiviral agents of the present invention are water-insoluble, have antibacterial and antiviral effects, and have significantly higher heat resistance and light resistance than dye-based antibacterial pigments.The antibacterial and antiviral effects are also exhibited in applications such as inks, printed matter, paints, coatings, plastics, fibers, films, and cosmetics, and can be used in a wide range of industrial fields.

[0014] Furthermore, the antibacterial and antiviral agents of the present invention exhibit pigment properties similar to those of conventional pigments, and therefore can be used in the same way as pigments, and can simultaneously provide coloring and antibacterial and antiviral properties. [Brief description of the drawings]

[0015] [Figure 1] 1 shows an SEM image of composition 1. [Diagram 2] This is the result of elemental mapping by SEM-EDS measurement performed at the same position and magnification as in Figure 1, with the white parts indicating the distribution of neodymium. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] The embodiments of the present invention described below merely represent some of the embodiments of the present invention, and the present invention is not limited to the described contents as long as the gist of the present invention is not significantly deviated from the gist of the present invention.

[0017] The antibacterial agent and antiviral agent of the present invention will be described below.

[0018] [Organic pigments] The organic pigment used in the antibacterial agent and antiviral agent of the present invention can be any known and commonly used pigment as long as it is a water-insoluble, fine-particle solid powder. For example, phthalocyanine, quinacridone, perylene, diketopyrrolopyrrole, soluble azo, insoluble azo, anthraquinone, perinone, thioindigo, dioxazine, isoindolinone, isoindoline, and quinophthalone pigments are listed. In particular, phthalocyanine, quinacridone, perylene, diketopyrrolopyrrole, soluble azo, and insoluble azo are 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 and antiviral agents of the present invention show particularly excellent antibacterial and antiviral effects, and are preferred.

[0019] [Phthalocyanine] The phthalocyanine used in the present invention is not particularly limited, and any known and commonly used phthalocyanine can be used. The phthalocyanine used in the present invention is represented by the general formula (2).

[0020] [ka] (2) (In the formula, M represents a metal selected from the group consisting of Cu, Fe, Zn, Co, Na, Mg, Al, Si, Ca, Ti, V, Mn, Ni, Cd, and Sn, or an oxymetal or metal halide thereof, or no metal. Each of R1 to R16 independently represents a hydrogen atom, a halogen atom, a carboxyl group, a hydroxyl group, a carbonyl group, an alkoxy group, or a sulfonyl group.)

[0021] For example, for general pigments, examples include CI Pigment Blue 16 when the phthalocyanine is metal-free, CI Pigment Blue 15, CI Pigment Blue 15:1, CI Pigment Blue 15:2, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 76, CI Pigment Green 7, and CI Pigment Green 36 when the central metal of the phthalocyanine is copper, CI Pigment Green 58 and CI Pigment Green 59 when the central metal of the phthalocyanine is zinc, CI Pigment Blue 75 when the central metal of the phthalocyanine is cobalt, and CI Pigment Blue 79 when the central metal of the phthalocyanine is aluminum.

[0022] The central metal of the phthalocyanine is preferably copper, iron, zinc, cobalt, sodium, magnesium, aluminum, silicon, calcium, titanium, vanadium, manganese, nickel, cadmium, or tin, or metal-free phthalocyanine. These metals and phthalocyanine rings may be unsubstituted or may have a halogen substituent, and the number of substituents (n) is theoretically possible to be n=0 to 16, but in order to exert the function as a pigment, it is preferable to have a substituent that does not dissolve in water or a solvent.

[0023] Among the above metal phthalocyanines, phthalocyanines having high antibacterial and antiviral properties are preferably used because they exhibit particularly high antibacterial and antiviral properties. Examples of central metals of phthalocyanines having high antibacterial and antiviral properties include iron, cobalt, sodium, magnesium, aluminum, silicon, manganese, nickel, cadmium, and tin.

[0024] Among these, phthalocyanines having a central metal of iron, sodium, magnesium, or cobalt are preferred because of their high antibacterial and antiviral effects, and further, phthalocyanines having an iron central metal are particularly preferred in the present invention.

[0025] [Quinacridone] The quinacridone used in the present invention is not particularly limited, and any known and commonly used quinacridone may be used. For example, the quinacridone may be represented by the general formula (3).

[0026] [ka] (3) (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.)

[0027] Examples of the pigments include CI Pigment Violet 19, CI Pigment Red 122, Pigment Red 202, Pigment Red 207, Pigment Red 206, and Pigment Red 209. Of these, CI Pigment Violet 19 is preferred.

[0028] [Perylene] The perylene used in the present invention is not particularly limited, and any known and commonly used perylene may be used. For example, the perylene is represented by the general formula (4).

[0029] [ka] (4) (In the formula, R1 and R2 each independently represent a hydrogen atom, an alkyl group, or an aryl group.)

[0030] Examples include CI Pigment Red 123, CI Pigment Red 149, CI Pigment Red 179, CI Pigment Red 178, CI Pigment Violet 29, and CI Pigment Black 31. Of these, CI Pigment Red 179 is preferred.

[0031] [Diketopyrrolopyrrole] The diketopyrrolopyrrole used in the present invention is not particularly limited, and any known and commonly used diketopyrrolopyrrole may be used. For example, the diketopyrrolopyrrole may be represented by the general formula (5).

[0032] [ka] (5) (In the formula, R1 to R10 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, or an amino group.)

[0033] Examples include CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 264, CI Pigment Red 272, CI Pigment Orange 71, and CI Pigment Orange 73. Of these, CI Pigment Red 254 is preferred.

[0034] [Soluble azo] The soluble azo used in the present invention is not particularly limited, and any known and commonly used azo may be used. For example, the soluble azo may be represented by the general formulas (6) and (7).

[0035] [ka] (6) (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, a nitro group, or the like. M represents barium, calcium, strontium, manganese, aluminum, or iron.)

[0036] [ka] (7) (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, a nitro group, or the like. M represents barium, calcium, strontium, manganese, aluminum, or iron.)

[0037] For example, CIPigmentRed53:1, CIPigmentRed53:2, CIPigmentRed53:3, CIPigmentRed49:1, CIPigmentRed49:2C.I.PigmentRed49:3, CIPigmentRed50:1, CIPigmentRed57:1, CIPigmentRed48:1, CIPigmentRed48:2, CIPigmentRed48:3, CIPigmentRed48:4, CIPigmentRed52:1, CIPigmentRed63:1, CIPigmentRed63:2, CIPigmentRed64:1, CIPigmentRed58:2, CIPigmentRed58:4, CIPigmentRed243, CIPigmentRed61, CIPigmentRed60:1, etc. are mentioned. Among them, CIPigmentRed48:1 is preferable.

[0038] [Insoluble azo] Insoluble azos can be classified into β-naphthol, naphthol AS, pyrazolone, acetoacetate arylide, benzimidazolone, etc., but the insoluble azos used in the present invention are not particularly limited and known and commonly used ones can be used. Among them, acetoacetate arylide is preferred, and among them, disazo yellow is more preferred. For example, β-naphthol is represented by the general formula (8):

[0039] [ka] (8) (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.)

[0040] Naphthol AS series has the general formula (9)

[0041] [ka] (9) (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.)

[0042] The pyrazolone system has the general formula (10)

[0043] [ka] (10) (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.)

[0044] Acetoacetate arylide monoazo type is represented by the general formula (11)

[0045] [ka] (11) (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.)

[0046] Acetoacetate arylide disazo type has the general formula (12)

[0047] [ka] (12) (In the formula, R1 to R8 each independently represent a hydrogen atom, a halogen atom, an alkyl group, a methoxy group, an aryl group, a cyano group, an amino group, a nitro group, or the like. A and B each independently represent an aryl group, or the like. C represents -CH (n is 0 or more) or -O-CH-O- (n is 1 or more).)

[0048] Benzimidazolone series has the general formula (13):

[0049] [ka] (13) (In the formula, R1 to R13 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.) It is expressed as:

[0050] Examples include CI Pigment Red 3, CI Pigment Orange 5, CI Pigment Red 5, CI Pigment Red 146, CI Pigment Violet 50, CI Pigment Blue 25, CI Pigment Orange 13, CI Pigment Yellow 74, CI Pigment Yellow 12, CI Pigment Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 17, CI Pigment Yellow 55, CI Pigment Yellow 83, CI Pigment Yellow 180, CI Pigment Yellow 154, and CI Pigment Red 185. Of these, CI Pigment Yellow 180 is preferred.

[0051] Phthalocyanine and condensed polycyclic pigments are often referred to as crude pigments, and after production, they often have large particle sizes and particle non-uniformity, and depending on the application, they have poor dispersibility, so if necessary, a further process called pigmentization is required to achieve the desired particle size and crystal shape.

[0052] Many of the pigments used in the present invention exhibit crystalline properties rather than molecular properties when pigmented. The crystalline properties create a band gap, and electrons to promote the reaction are exchanged through the valence band or conduction band. When multiple pigments are present, the electrons necessary for the reaction can be transferred between pigments in the presence of a resin, as in hopping conduction, making it possible for electrons to be accepted by specific functional groups such as bacteria.

[0053] On the other hand, in the case of dyes, the decomposition reaction occurs through an oxidation-reduction reaction, i.e., the molecule transitions from HOMO to LUMO, or when a specific atom comes into contact with a specific functional group of bacteria, etc.

[0054] In other words, the crystalline nature of pigments allows the antibacterial and antiviral effects to extend not only to the area in contact with the pigment, but also to an area slightly distant from the pigment. Specifically, in the case of dyes, the antibacterial properties disappear when the dye is covered with resin in a coating film or the like, but in the case of pigments, the antibacterial and antiviral effects can be maintained even if the pigment is covered to some extent with resin in a coating film or the like.

[0055] For example, among metal species of phthalocyanine, metal species that are prone to oxidation-reduction of metal ions in electrochemical reactions are expected to have higher antibacterial and antiviral properties than metal species that are prone to oxidation-reduction of the phthalocyanine ring.

[0056] The pigment may be in a particulate or needle shape, and the shape is not particularly limited. There is also no particular limit to the particle size or aspect ratio, but in general, the average particle size of finely divided or refined pigment is preferably 20 to 300 nm, and the aspect ratio is preferably about 1 to 10, and more preferably 20 to 200 nm, and the aspect ratio is particularly preferably about 1 to 5.

[0057] [Inorganic pigments] Inorganic pigments used in the antibacterial and antiviral agents of the present invention include metal compounds such as titanium, zinc, lead, chromium, iron, cobalt, cadmium, and copper, high-carbon substances such as carbon black, metal powders such as aluminum and copper, and nanoparticles of gold and silver, but are not particularly limited and publicly known and commonly used pigments can be used. In addition, they are classified according to their usage characteristics into extender pigments, white pigments, colored pigments, and pearl pigments, but can be used without particular limitations. 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 inorganic pigments, iron oxide is particularly preferred. These pigments can be used alone or in combination of two or more.

[0058] The iron oxide used in the present invention is not particularly limited, and known and commonly used iron oxides can be used. Black iron oxide refers to triiron tetroxide and is expressed as Fe3O4 (or FeOFe2O3), red iron oxide refers to iron(III) oxide and is expressed as Fe2O3, and yellow iron oxide refers to ferric hydroxide and is expressed as Fe2O3·H2O (or FeOOH). Among the above iron oxides, black iron oxide and red iron oxide are particularly preferred.

[0059] Examples include CI Pigment Black 11, CI Pigment Red 101, CI Pigment Red 102, CI Pigment Brown 6, CI Pigment Yellow 42, and CI Pigment Yellow 43. Of these, CI Pigment Black 11 and CI Pigment Red 101 are preferred.

[0060] In the present invention, organic or inorganic pigments may be used alone or in combination.

[0061] [Fatty acid metal salts] The fatty acid metal salt used in the antibacterial and antiviral agents of the present invention contains, as a metal species, 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. Among these, neodymium, lanthanum, and cobalt have high antibacterial and antiviral effects and are therefore preferred in the present invention.

[0062] The fatty acid metal salt used in the antibacterial and antiviral agents of the present invention is, for example, a compound represented by the following general formula (14).

[0063] [ka]

[0064] (In the general formula (14), R is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms; n is an integer ranging from 1 to 4; 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.

[0065] In the general formula (14), when n is an integer of 2 or more, the multiple R's may be the same or different.

[0066] The alkyl group having 1 to 21 carbon atoms represented by R may be a linear or branched alkyl group, or may contain an alicyclic structure.

[0067] The alkyl group having 1 to 21 carbon atoms represented by 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 the carboxylic acid residue include acetic acid residue, propionic acid residue, butanoic acid residue, pentanoic acid residue, acrylic acid residue, methacrylic acid residue, octylic acid residue (2-ethylhexanoic acid residue), neodecanoic acid residue, naphthenic acid residue, isononanoic acid residue, tung oil acid residue, tall oil fatty acid residue, coconut oil fatty acid residue, soybean oil fatty acid residue, linseed oil fatty acid residue, safflower oil fatty acid residue, dehydrated castor oil fatty acid residue, tung oil fatty acid residue, lauric acid residue, myristic acid residue, palmitic acid residue, stearic acid residue, isostearic acid residue, and oleic acid residue.

[0068] From the viewpoint of adhesion to a substrate, which will be described later, the alkyl group having 1 to 21 carbon atoms for R is preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 11 carbon atoms, and even more preferably an acetic acid residue, a propionic acid residue, a butanoic acid residue, a pentanoic acid residue, a 2-ethylhexanoic acid residue, an isononanoic acid residue, a neodecanoic acid residue, or a naphthenic acid residue.

[0069] 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, preferably bismuth, neodymium, magnesium, cobalt, copper, silver or zinc, more preferably bismuth, neodymium or magnesium.

[0070] When the metal of the fatty acid metal salt is bismuth, neodymium or magnesium, discoloration due to the addition of an antibacterial agent or an antiviral agent can be made less likely to occur.

[0071] In the present invention, rare earth refers to one or more elements 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).

[0072] n is a number determined by the ionic valence of the metal atom of M. For example, if M is boron, n is 3, and if M is cobalt, n is 2.

[0073] The fatty acid metal salt which is the antibacterial agent and antiviral agent of the present invention also includes a form of fatty acid metal borate. The fatty acid metal borate is, for example, a compound represented by the following general formula (15).

[0074] [ka]

[0075] (In the general formula (15), R is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms; 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.

[0076] In the general formula (15), the alkyl group of R having 1 to 21 carbon atoms is the same as the alkyl group of R having 1 to 21 carbon atoms in the general formula (14). Similarly, in the general formula (15), the metal of M is the same as the metal of M in the general formula (14).

[0077] The fatty acid metal salts used in the antibacterial and antiviral agents of the present invention can be used alone or in combination of two or more kinds.

[0078] The fatty acid metal salt can be produced by a known method, or a commercially available product may be used.

[0079] As for the fatty acid metal salts used in the antibacterial and antiviral agents 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.

[0080] [Antibacterial and antiviral agents] The antibacterial agent and antiviral agent of the present invention are compositions containing a pigment and a fatty acid metal salt, and may be present in either a form in which each is attached to the other, or a form in which one is coated on the other. In particular, a form in which the surface of the pigment is coated with the fatty acid metal salt is preferred.

[0081] The ratio of the pigment to the fatty acid metal salt in the antibacterial agent and antiviral agent of the present invention is, by mass, pigment:fatty acid metal salt=99:1 to 50:50, preferably 98:2 to 60:40, and particularly preferably 95:5 to 70:30. It is preferable from the viewpoint of antibacterial and antiviral properties that the ratio of the fatty acid metal salt is 1% or more of the antibacterial agent and antiviral agent, and it is preferable from the viewpoint of ease of handling that the ratio of the fatty acid metal salt is 50% or less of the antibacterial agent and antiviral agent, so it is preferable that the ratio of the pigment to the fatty acid metal salt satisfies the above range.

[0082] When the surface of the pigment is coated with a fatty acid metal salt, the mass ratio of pigment to fatty acid metal salt is preferably 99:1 to 50:50, 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. If the above range is satisfied, it is preferable from the viewpoint of ease of handling.

[0083] In the present invention, "antibacterial" means to include the effect of reducing the number of bacteria, the effect of inactivating bacteria, the effect of reducing the infectivity of bacteria, etc. Similarly, in the present invention, "antiviral" means to include the effect of reducing the number of viruses, the effect of inactivating viruses, the effect of reducing the infectivity of viruses, etc.

[0084] In the present invention, the target bacteria for antibacterial treatment are not particularly limited, and may be either bacteria or fungi. Examples of bacteria include gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Salmonella, Moraxella, Legionella, etc.; gram-positive bacteria such as Staphylococcus aureus and Clostridium bacteria, etc. Examples of fungi include yeasts such as Candida, Rhodotorula, and baker's yeast; and molds such as red mold and black mold.

[0085] In the present invention, the viruses to be treated against are not particularly limited, and may be any of the known enveloped viruses (viruses having an envelope) and non-enveloped viruses (viruses not having an envelope).

[0086] Examples of the enveloped viruses include coronavirus, influenza virus, rubella virus, Ebola virus, measles virus, varicella-zoster virus, herpes virus, mumps virus, arbovirus, RS virus, SARS virus, hepatitis virus (e.g., 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.

[0087] Examples of the non-enveloped viruses include adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, polyomavirus, BK virus, rhinovirus, and feline calicivirus.

[0088] (Antibacterial effect) Examples of indicators of antibacterial activity include bacterial growth tests using culture kits and antibacterial tests specified in JIS standards.

[0089] The main purpose of using a culture kit is to understand the phenomenon in which common bacteria and fungi present in nature such as food, air, and water grow in the culture medium of the culture kit by observing the occurrence of colonies, but by contacting the culture medium with a substance having an antibacterial effect, a certain amount of bacteria and fungi are killed or their growth is suppressed, so that colonies do not grow or the growth of colonies is delayed. Bacterial growth tests using a culture kit can be evaluated by regular observation of the above phenomenon.

[0090] Examples of the common bacteria and fungi include, but are not limited to, Escherichia coli, Staphylococcus aureus, Bacillus cereus, Salmonella, Pseudomonas aeruginosa, fungi, and the like, or common live bacteria containing the bacteria and fungi.

[0091] As the culture kit, a general kit can be used, for example, a simple microorganism measuring device, Sanai Biochecker (manufactured by Sanai Oil Co., Ltd.), a medium for measuring bacterial count, Compact Dry (manufactured by Nissui Pharmaceutical Co., Ltd.), and the like.

[0092] The antibacterial test specified in the JIS standard mainly targets typical 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. In summary, the test bacteria liquid is inoculated into a sample, and the bacteria liquid is placed in contact with a film or glass and irradiated with light for a certain period of time or left in a dark place, after which the collected bacteria liquid is diluted and cultured on an agar medium. After culturing, the antibacterial activity value is calculated by comparing the number of colonies that have appeared. Specifically, the antibacterial activity value can be calculated using the bacteria liquid absorption method, transfer method, bacteria transfer method, and halo method specified in JIS R1702 Antibacterial Test Methods and Antibacterial Effects of Photocatalyst-treated Products, JIS R1752 Antibacterial Test Methods and Antibacterial Effects of Visible Light-Responsive Photocatalyst-treated Products, JIS L1902 Antibacterial Test Methods and Antibacterial Effects of Textile Products, JIS Z2801 Antibacterial Finished Products - Antibacterial Test Methods and Antibacterial Effects, or JIS L1902 Antibacterial Test Methods and Antibacterial Effects of Textile Products.

[0093] (Antiviral effect) Examples of indicators of antiviral activity include antiviral tests defined in JIS and ISO standards. Antiviral tests specified in the JIS and ISO standards are mainly targeted at typical enveloped influenza viruses, non-enveloped feline caliciviruses, or bacteriophages. In general, a virus liquid or bacteriophage liquid is inoculated into a sample, and the liquid is exposed to light for a certain period of time while in contact with a film or glass, or left to stand in a dark place, and then the collected liquid is diluted and cultured on an agar medium. After culture, the antiviral activity value is determined by comparing the number of plaques. Alternatively, a virus liquid is inoculated into a sample, and the sample is exposed to light for a certain period of time while in contact with a film or glass via the virus liquid, or left to stand in a dark place, and then the virus liquid on the sample is washed off and collected, and the virus infectivity is compared to determine the antiviral activity value. Specifically, examples of such antiviral tests include JIS R1706 Antiviral Test Method for Photocatalytic Materials - Method using bacteriophage Qβ, JIS R1756 Antiviral Test Method for Visible Light Response Photocatalytic Materials - Method using bacteriophage Qβ, ISO21702 Measurement of antiviral activity on plastics and other non-porous surfaces, and JIS L1922 Antiviral Test Method for Textile Products.

[0094] <Antibacterial evaluation of coating film> Antibacterial tests were conducted on Staphylococcus aureus (NBRC 12732) and Escherichia coli (NBRC 3972) using the following methods. A 5 cm x 5 cm coating that had been cleaned by UV irradiation was inoculated with 0.1 ml of test bacteria liquid, and the bacteria liquid was placed in contact with a film or glass and left to stand in a dark place for 8 or 24 hours. The collected bacteria liquid was then diluted and cultured on an agar medium. After the culture, the antibacterial activity value was calculated by comparing the number of colonies that appeared. The calculation formula is R = (U t -U0)-(A t -U0)=U t -A t (R: antibacterial activity value, U0: average logarithmic value of viable bacteria count immediately after inoculation of unprocessed product, U t A: Average logarithm of viable bacteria count after 8 or 24 hours for unprocessed productst It is expressed as the average logarithmic value of the number of live bacteria after 8 or 24 hours on the processed product). The processed product is a coating film made from a dispersion containing the test object, and the unprocessed product is a coating film made from a solution consisting of a PET film or a synthetic resin, a polyurethane resin, and a solvent. As a guideline for antibacterial activity value, for example, JIS Z 2801:2021 Antibacterial processed products - Antibacterial test method, antibacterial effect specifies that the criterion for the antibacterial effect is 2.0 or more. In addition, an antibacterial activity value of 2.0 means that the processed product suppressed the growth of bacteria after the test by 99% compared to the unprocessed product. However, it does not necessarily mean that bacteria do not grow.

[0095] <Antiviral properties evaluation of coating film> Antiviral tests were performed using bacteriophage Qβ (NBRC 20012, host E. coli (NBRC 106373)) and bacteriophage Φ6 (NBRC105899, host Pseudomonas syringae (NBRC14084)) using the following method. A test phage liquid was inoculated onto a 5cm x 5cm coating film, and the phage liquid was placed in contact with a film or glass and left to stand in the dark for 4 hours. The collected phage liquid was then diluted and cultured on an agar medium. After culture, the antiviral activity value was calculated by comparing the number of colonies that emerged. The calculation formula is V D :Antiviral activity value (in the dark):[V D =Log(B D )-Log(C D )](D: dark place, B D : Infectivity value of unprocessed product after standing in the dark for 4 hours, C D (The infectivity value is expressed as the infectivity value of the processed product after standing in a dark place for 4 hours.) The processed product is a coating film made by forming a film from a dispersion containing the test object, and the unprocessed product is a coating film made from a solution consisting of a PET film or a synthetic resin, a polyurethane resin, and a solvent. For example, an antiviral activity value of 2.0 means that the treated product inhibited phage proliferation by 99% after the test compared to the untreated product. However, it does not necessarily mean that the phage does not proliferate.

[0096] By utilizing the antibacterial agent and antiviral agent of the present invention, it is possible to provide inks, printed matter, paints, coatings, plastics, fibers, films, cosmetics, etc. The applications described in detail below are examples, and the antibacterial agent and antiviral agent of the present invention can be used for any application having antibacterial, sterilizing, and antiviral properties.

[0097] (Ink applications) The antibacterial agent and antiviral agent of the present invention can provide a printing ink having antibacterial and antiviral effects. The printing ink can be prepared by mixing the antibacterial agent and antiviral agent of the present invention with various known and commonly used binder resins, various solvents, various additives, etc., according to a conventional preparation method. Specifically, the liquid ink can be prepared by preparing a liquid ink base ink having a high pigment concentration and using various binders, various solvents, various additives, etc.

[0098] The antibacterial and antiviral agents of the present invention can be used to produce PU inks and NC inks having antibacterial and antiviral properties, and are suitable as organic compositions for gravure printing inks and flexographic printing inks. The PU inks are made of PU resins, pigments, solvents, and various additives, while the NC inks are made of NC resins, pigments, solvents, and various additives. The PU resins are not particularly limited as long as they have a urethane structure in the skeleton, and include polyurethanes, polyurethane polyureas, and the like. Examples of the solvent include aromatic organic solvents such as toluene and xylene, ketone-based solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone, ester-based solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, isobutyl acetate, propylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate, alcohol-based solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, and t-butanol, propylene glycol monoethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol mono-n-propanol. Examples of the solvent include (poly)alkylene glycol monoalkyl ether solvents such as ethyl ether, ethylene glycol mono-i-propyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, and diethylene glycol mono-i-propyl 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. The solvents may be used alone or in combination of two or more.Examples of various additives that can be used include anionic, nonionic, cationic, amphoteric and other surfactants, rosins such as gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleic rosin, hardened rosin, and phthalic acid alkyd resin, pigment derivatives, dispersants, wetting agents, adhesion aids, leveling agents, defoamers, antistatic agents, trapping agents, antiblocking agents, and wax components.

[0099] When the antibacterial agent or antiviral agent of the present invention is used as a printing ink, the printing ink using the antibacterial agent or antiviral agent of the present invention prepared as described above can be used by diluting it with ethyl acetate, a polyurethane-based varnish, or a polyamide-based varnish. A known, commonly used method can be used to prepare the printing ink.

[0100] (Paint application) When the antibacterial agent and antiviral agent of the present invention are used as a paint having antibacterial and antiviral properties, various resins can be used as the paint, such as acrylic resin, melamine resin, epoxy resin, polyester resin, polyurethane resin, polyamide resin, and phenolic resin.

[0101] Solvents used in paints include aromatic solvents such as toluene, xylene, and methoxybenzene, acetate ester solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate, propionate solvents such as ethoxyethyl propionate, alcohol solvents such as methanol, ethanol, propanol, n-butanol, and isobutanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, and diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, aliphatic hydrocarbon solvents such as hexane, nitrogen compound solvents such as N,N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline, and pyridine, lactone solvents such as γ-butyrolactone, carbamate esters such as a 48:52 mixture of methyl carbamate and ethyl carbamate, and water. As the solvent, particularly, water-soluble polar solvents such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, lactone-based, and water are suitable.

[0102] Also, when pigment additives and / or antibacterial and antiviral agents are dispersed or mixed in a liquid resin to form a resin composition for coating, conventional additives such as dispersants, fillers, coating adjuvants, drying agents, plasticizers and / or auxiliary pigments can be used. This is accomplished by dispersing or mixing each component alone or several together, by collecting all the components, or by adding them all at once.

[0103] Dispersing machines for dispersing the mixture containing the antibacterial agent and the antiviral agent prepared according to the application as described above include known dispersing machines such as a disperser, a homomixer, a paint conditioner, a scandex, a bead mill, an attritor, a ball mill, a two-roll mill, a three-roll mill, and a pressure kneader, but are not limited thereto. Dispersion of the antibacterial agent and the antiviral agent is performed by adding a resin and a solvent so that the viscosity is such that the antibacterial agent and the antiviral agent can be dispersed by these dispersing machines. The high concentration paint base after dispersion has a solid content of 5 to 20%, and is further mixed with a resin and a solvent to be used as a paint.

[0104] (Plastic applications) The antibacterial agent and antiviral agent of the present invention can also be used for plastic applications having antibacterial and antiviral effects. When obtaining plastic molded products, for example, thermoplastic resins (plastics) for thermoforming such as injection molding and press molding, such as polyolefins such as polyethylene and polypropylene, and polyvinyl chloride resins, are used, and the antibacterial agent and antiviral agent of the present invention can be used by kneading them into these resins by a conventionally known method.

[0105] (Cosmetic use) The antibacterial and antiviral agents of the present invention can be used as cosmetics. There are no particular limitations on the cosmetics used, and the antibacterial and antiviral agents of the present invention can be used in various types of cosmetics.

[0106] The cosmetic may be any type of cosmetic as long as it can effectively exert its function. The cosmetic may be a lotion, cream gel, spray, etc. Examples of the cosmetic include skin care cosmetics such as face wash, makeup remover, skin lotion, beauty essence, pack, protective emulsion, protective cream, whitening cosmetics, and UV protection cosmetics, makeup cosmetics such as foundation, face powder, makeup base, lipstick, eye makeup, blusher, and nail enamel, hair care cosmetics such as shampoo, hair rinse, hair treatment, hair styling agent, permanent wave agent, hair dye, and hair growth agent, and body care cosmetics such as body cleansing cosmetics, deodorant cosmetics, and bath agents.

[0107] The antibacterial agent and antiviral agent of the present invention used in the cosmetic can be appropriately set according to the type of cosmetic. The content in the cosmetic is usually in the range of 0.1 to 99% by mass, and generally, it is preferable that the amount is in the range of 0.1 to 10% by mass. On the other hand, in the case of makeup cosmetics, the amount may be in the range of 5 to 80% by mass, 10 to 70% by mass, or 20 to 60% by mass. When the amount of the composition of the present invention contained in the cosmetic is in the above range, the function such as coloring property can be effectively exhibited, and the function required for the cosmetic can be maintained.

[0108] The cosmetics may contain, depending on the type of cosmetic, in addition to the antibacterial agent or antiviral agent of the present invention, a carrier, pigment, oil, sterol, amino acid, moisturizer, powder, colorant, pH adjuster, fragrance, essential oil, cosmetic active ingredient, vitamin, essential fatty acid, sphingolipid, self-tanning agent, excipient, filler, emulsifier, antioxidant, surfactant, chelating agent, gelling agent, thickener, emollient, wetting agent, moisturizer, mineral, viscosity adjuster, flow adjuster, keratolytic agent, etc., which are acceptable as cosmetic ingredients. These may include retinoids, hormonal compounds, alpha hydroxy acids, alpha keto acids, antimycobacterial agents, antifungal agents, antibacterial agents, antiviral agents, analgesics, antiallergic agents, antihistamines, anti-inflammatory agents, anti-irritants, antitumor agents, immune system boosters, immune system suppressants, antiacne agents, anesthetics, disinfectants, insect repellents, skin cooling compounds, skin protectants, skin penetration enhancers, exfoliants, lubricants, fragrances, dyes, bleaching agents, hypopigmenting agents, preservatives, stabilizers, pharmaceuticals, light stabilizers, and spherical powders.

[0109] The cosmetic product can be produced by mixing the antibacterial agent, antiviral agent and other cosmetic ingredients of the present invention. Furthermore, cosmetics containing the antibacterial and antiviral agents of the present invention can be used in the same manner as ordinary cosmetics, depending on the type of the cosmetic, etc.

[0110] When the antibacterial agent or antiviral agent of the present invention is used in paints or plastics, it is preferable that the antibacterial agent or antiviral agent of the present invention is present on the paint surface or in the vicinity of the plastic surface. The above adjustment can be achieved by adjusting the type of alkyl group R in the fatty acid metal salt represented by the above formula (14) or by controlling the dispersion conditions according to the type of resin used in the paint or plastic.

[0111] It has been found that the antibacterial and antiviral properties are particularly excellent when the antibacterial and antiviral agents of the present invention contain a composition in which the surface of a pigment is coated with a fatty acid metal salt.The reason for this is unclear, but it is speculated that when the composition in which the surface of a pigment is coated with a fatty acid metal salt, the uncoated pigment, or the uncoated fatty acid metal salt migrates to the vicinity of the surface of a coating film or plastic, the remaining components also tend to migrate to the vicinity of the surface. EXAMPLES

[0112] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the following examples, "%" in the compositions means "% by mass".

[0113] The pigments used in Examples 1 to 15 and Comparative Examples 1 to 13 are described below.

[0114] (iron phthalocyanine) The iron phthalocyanine used was product name P-26 (manufactured by Sanyo Pigment Co., Ltd.).

[0115] (Copper Phthalocyanine) The copper phthalocyanine used was CI Pigment Blue 15:3, product name: FASTOGEN BLUE PA5380 (manufactured by DIC Corporation).

[0116] (Brominated chlorinated zinc phthalocyanine) The brominated chlorinated zinc phthalocyanine used was CI Pigment Green 58, product name: FASTOGEN GREEN A110 (manufactured by DIC Corporation).

[0117] (Quinacridone) The quinacridone used was CI Pigment Violet 19, product name: FASTOGEN SUPER RED 7061BCONC (manufactured by DIC Corporation).

[0118] (Perylene) The perylene used was CI Pigment Red 179, product name: PERRINDO MAROON 179 229-6438 (manufactured by DIC Corporation).

[0119] (Diketopyrrolopyrrole) The diketopyrrolopyrrole used was CI Pigment Red 254, product name: FASTOGEN SUPER RED 254 226-0200 (manufactured by DIC Corporation).

[0120] (azobarium salts) The azobarium salt used was CI Pigment Red 48:1, product name: SYMULER RED 3109 (manufactured by DIC Corporation).

[0121] (Diazolidinium) The disazo used was CI Pigment Yellow 180, product name: SYMULER Fast Yellow BY2000GT (manufactured by DIC Corporation).

[0122] (Black iron oxide) The black iron oxide used was CI Pigment Black 11, product name: C33-134 SunCROMA Black Iron Oxide (manufactured by Sun Chemical).

[0123] (red iron oxide) The red iron oxide used was CI Pigment Red 101, product name: C33-128 SunCROMA Red Iron Oxide (manufactured by Sun Chemical).

[0124] The methods for preparing the fatty acid metal salts used in Examples 1 to 15 and Comparative Examples 1 to 13 will be described below.

[0125] (Preparation of neodymium neodecanoate) A 1.0 L separable flask was charged with 224.8 g of neodecanoic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 60.0 g of neodymium oxide (manufactured by Kanto Chemical Co., Ltd.), and reacted at 130°C. After that, the mixture was dehydrated under reduced pressure at 0.08 bar using an aspirator at 130°C for 2 hours to obtain neodymium neodecanoate. The obtained neodymium neodecanoate was a light purple, highly viscous, sticky solid.

[0126] (Preparation of lanthanum neodecanoate solution) 83.1 g of neodecanoic acid (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 21.5 g of lanthanum oxide (manufactured by Kanto Chemical Co., Ltd.) were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 107.6 g of cyclohexane was added to obtain 208.5 g of lanthanum neodecanoate solution. The lanthanum content in the obtained lanthanum neodecanoate solution was 8.8 mass%.

[0127] (Preparation of cobalt 2-ethylhexanoate solution) 319.0 g of 2-ethylhexanoic acid (Kanto Chemical Co., Ltd.) and 100.0 g of cobalt hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were reacted at 130°C, and after dehydration under reduced pressure at 130°C, 134.2 g of petroleum hydrocarbon was added to obtain 502.3 g of a cobalt 2-ethylhexanoate solution. The cobalt content in the obtained cobalt 2-ethylhexanoate solution was 12 mass%.

[0128] The neodymium neodecanoate and lanthanum neodecanoate solutions and the cobalt 2-ethylhexanoate solution obtained above were dissolved in isobutanol, methyl ethyl ketone, and toluene, but insoluble in acetone and propylene glycol monomethyl ether acetate. The solubility was evaluated by adding 0.1 g of the neodymium neodecanoate or lanthanum neodecanoate solution or the cobalt 2-ethylhexanoate solution and 2.0 g of solvent to a screw bottle (13.5 mL) and mixing. If no solid remained and the solution was transparent after leaving it for a while, it was rated as "dissolved", and if solid remained or the solution was cloudy, it was rated as "insoluble".

[0129] The following describes the methods for preparing the compositions used in Examples 1 to 15. Table 1 shows the amounts of pigments and fatty acid metal salts used in preparing the compositions.

[0130] [Table 1]

[0131] (Preparation of Composition 1) In a 0.5 L separable flask, 5.0 g of neodymium neodecanoate and 60.0 g of isobutanol (Kanto Chemical Co., Ltd.) were mixed and stirred, then 20.0 g of iron phthalocyanine and 120.0 g of water were added, and the mixture was refluxed for 1 hour while stirring. After that, 120.0 g of water was added and the solvent was distilled off, followed by filtration, washing, drying and pulverization to obtain composition 1.

[0132] (Preparation of Compositions 2, 5 to 15) In a 0.5 L separable flask, fatty acid metal salt and 30.0 g of isobutanol (Kanto Chemical Co., Ltd.) were mixed and stirred, and then pigment and 60.0 g of water were added and refluxed for 1 hour with stirring. After that, 60.0 g of water was added and the solvent was distilled off, followed by filtration, washing, drying and pulverization to obtain a composition.

[0133] (Composition 3, 4) The fatty acid metal salt was distilled off using a 50 mL eggplant flask, and 30.0 g of isobutanol (Kanto Chemical Co., Ltd.) was added and transferred to a 0.5 L separable flask. Then, pigment and 60.0 g of water were added, and the mixture was refluxed for 1 hour while stirring. Then, 60.0 g of water was added, and the solvent was distilled off, followed by filtration, washing, drying, and pulverization to obtain a composition.

[0134] Elemental mapping was carried out by SEM-EDS measurement on the obtained compositions 1 to 15. As a result, for compositions 1 to 15, elements corresponding to the metal species of the fatty acid metal salt were detected at the same location as the particle image, and it was inferred that the fatty acid metal salt was attached to or coated on the pigment surface. For SEM-EDS, the obtained compositions were platinum-deposited and measured 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 a working distance (WD) of 10 mm, an accelerating voltage of 15.0 or 20.0 kv, and a visual field of 1000x to 5000x was targeted.

[0135] For example, the SEM-EDS results for composition 1 are shown in Figures 1 and 2. Figure 1 shows an SEM image of composition 1, and Figure 2 shows the results of element mapping by SEM-EDS measurement at the same position and magnification as in Figure 1, with the white areas indicating the distribution of neodymium. Since the particle image and neodymium are detected in the same place, it can be inferred that a fatty acid metal salt is attached to or coated on the iron phthalocyanine surface.

[0136] The method for preparing the coating films used in the antibacterial and antiviral tests will be described below.

[0137] The following resins were used in preparing the coating film: Resin 1: Synthetic resin (product name: V343-306SA (DIC Graphics Corporation, solids concentration: 25%, solvent weight ratio: methyl ethyl ketone / ethyl acetate / toluene = 35 / 20 / 20) Resin 2: Synthetic resin (product name: V343-306SA (DIC Graphics Corporation, solids concentration: 25%, solvent weight ratio: methyl ethyl ketone / ethyl acetate / toluene = 35 / 20 / 20)) with the solvent components distilled off Resin 3: Polyurethane resin (product name: Sanprene IB-D12 (manufactured by Sanyo Chemical Industries, Ltd., solid content concentration: 30%, weight ratio of solvent: methyl ethyl ketone / isopropanol = 47 / 23) Resin 4: Polyurethane resin (product name: Sanprene IB-D12 (manufactured by Sanyo Chemical Industries, Ltd., solid content concentration: 30%, solvent weight ratio: methyl ethyl ketone / isopropanol = 47 / 23)) with the solvent components distilled off

[0138] In preparing the coating film, the solvents used were acetone (Kanto Chemical Co., Ltd.) and propylene glycol monomethyl ether acetate (hereinafter referred to as PGMEA, Kanto Chemical Co., Ltd.), or methyl ethyl ketone (hereinafter referred to as MEK, Kanto Chemical Co., Ltd.) and toluene (Kanto Chemical Co., Ltd.).

[0139] The formulations used to prepare 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, coating films were prepared using the compositions obtained in the composition preparation step according to the formulation in Table 2, and in Comparative Examples 1 to 13, coating films were prepared by mixing pigments or fatty acid metal salts according to the formulations in Table 3. The amount added refers to the weight ratio of the composition, pigment, or fatty acid metal salt contained relative to the resin solid content in the coating film.

[0140] [Table 2]

[0141] [Table 3]

[0142] (Examples 1 to 15) Using the formulations in Table 2, each coating film was obtained in the following manner.

[0143] The antibacterial agent, antiviral agent, resin, solvent, and 80 g of 1 / 8 inch steel beads were placed in a plastic bottle and shaken for 30 minutes in a paint conditioner to obtain a dispersion.

[0144] The obtained dispersion was applied to a 188 μm PET film using a bar coater No. 6, dried with a dryer, and further dried at 150° C. for 15 minutes to obtain the coating films of Examples 1 to 15.

[0145] (Comparative Examples 1 to 13) Using the formulations in Table 3, each coating film was obtained in the following manner.

[0146] The pigment or fatty acid metal salt, resin, solvent, and 80 g of 1 / 8 inch steel beads were placed in a plastic bottle and shaken for 30 minutes in a paint conditioner to obtain a dispersion.

[0147] The obtained dispersion was applied to a 188 μm PET film using a bar coater No. 6, dried with a dryer, and further dried at 150° C. for 15 minutes to obtain coating films of Comparative Examples 1 to 13.

[0148] <Antibacterial test 1> With reference to JIS R 1752:2020, antibacterial tests were conducted on Escherichia coli (NBRC3972) using the following method.

[0149] A 5cm x 5cm coating film that had been cleaned by UV irradiation was inoculated with 0.1ml of test bacteria liquid, and the bacteria liquid was placed in contact with a film or glass and left to stand in a dark place for 24 hours. The collected bacteria liquid was then diluted and cultured on an agar medium. After culture, the antibacterial activity value was calculated by comparing the number of colonies that emerged. The calculation formula is R = (Ut-U0)-(At-U0) = Ut-At (R: antibacterial activity value, U0: average value of logarithm of viable bacteria count immediately after inoculation of unprocessed products, Ut: average value of logarithm of viable bacteria count after 24 hours of unprocessed products, At: average value of logarithm of viable bacteria count after 24 hours of processed products). The processed product is a coating film formed from a dispersion containing the test object, and the unprocessed product is a PET film.

[0150] <Antibacterial test 2> The antibacterial test was performed in the same manner as in <Antibacterial test 1>, except that Staphylococcus aureus (NBRC12732) was used instead of Escherichia coli (NBRC3972).

[0151] <Antibacterial test 3> With reference to JIS R 1752:2020, antibacterial tests were conducted on Escherichia coli (NBRC3972) using the following method.

[0152] A 5cm x 5cm coating film that had been cleaned by ultraviolet irradiation was inoculated with 0.1ml of test bacteria liquid, and the bacteria liquid was placed in contact with a film or glass and left to stand in a dark place for 8 hours. The collected bacteria liquid was then diluted and cultured on an agar medium. After the culture, the antibacterial activity value was calculated by comparing the number of colonies that were generated. The calculation formula is R = (Ut-U0)-(At-U0) = Ut-At (R: antibacterial activity value, U0: average value of the logarithm of the number of live bacteria immediately after inoculation of the unprocessed product, Ut: average value of the logarithm of the number of live bacteria after 8 hours of the unprocessed product, At: average value of the logarithm of the number of live bacteria after 8 hours of the processed product). The processed product is a coating film formed from a dispersion containing the test object, and the unprocessed product is a coating film formed from a solution consisting of a synthetic resin, a polyurethane resin, and a solvent.

[0153] <Antibacterial test 4> The antibacterial test was performed in the same manner as in <Antibacterial test 3>, except that Staphylococcus aureus (NBRC12732) was used instead of Escherichia coli (NBRC3972).

[0154] <Antiviral Test 1> With reference to JIS R 1756:2020, antiviral tests were conducted using the following method on bacteriophage Qβ (NBRC20012, host E. coli (NBRC106373)).

[0155] A test phage liquid was inoculated onto a 5 cm x 5 cm coating film, and the phage liquid was allowed to stand in the dark for 4 hours while it was attached to a film or glass. The collected phage liquid was then diluted and cultured on an agar medium. After the culture, the antiviral activity value was determined by comparing the number of colonies that emerged. The calculation formula is VD: antiviral activity value (in the dark): [VD = Log (BD) - Log (CD)] (D: in the dark, BD: infectivity value of unprocessed product after standing in the dark for 4 hours, CD: infectivity value of processed product after standing in the dark for 4 hours). The processed product is a coating film formed from a dispersion containing the test object, and the unprocessed product is a PET film.

[0156] <Antiviral test 2> With reference to JIS R 1756:2020, antiviral tests were conducted using the following method on bacteriophage Qβ (NBRC20012, host E. coli (NBRC106373)).

[0157] A test phage liquid was inoculated onto a 5 cm x 5 cm coating film, and the phage liquid was allowed to stand in the dark for 4 hours while being attached to a film or glass. The collected phage liquid was then diluted and cultured on an agar medium. After the culture, the antiviral activity value was determined by comparing the number of colonies that emerged. The calculation formula is VD: antiviral activity value (in the dark): [VD = Log (BD) - Log (CD)] (D: in the dark, BD: infectivity value of unprocessed product after standing in the dark for 4 hours, CD: infectivity value of processed product after standing in the dark for 4 hours). The processed product is a coating film formed from a dispersion containing the test object, and the unprocessed product is a coating film formed from a solution consisting of a synthetic resin, a polyurethane resin, and a solvent.

[0158] <Antiviral test 3> An antiviral test was performed in the same manner as in <Antiviral test 2>, except that bacteriophage Φ6 (NBRC105899, host Pseudomonas syringae (NBRC14084)) was used instead of bacteriophage Qβ (NBRC20012, host E. coli (NBRC106373)).

[0159] <Antibacterial Test 1> was carried out on the coating films of Example 1 and Comparative Examples 1 and 2. The results are shown in Table 4.

[0160] [Table 4]

[0161] An <Antibacterial Test 2> was carried out on the coating films of Example 1 and Comparative Examples 1 and 2. The results are shown in Table 5.

[0162] [Table 5]

[0163] An <antibacterial test 3> was carried out on Examples 3, 5 to 10, 12, and 13, and Comparative Examples 5 to 10, 12, and 13. The results are shown in Table 6.

[0164] [Table 6]

[0165] <Antibacterial Test 4> was carried out on Examples 2, 4 to 15 and Comparative Examples 3 to 13. The results are shown in Table 7.

[0166] [Table 7]

[0167] <Antiviral Test 1> was carried out on the coating films of Example 1 and Comparative Examples 1 and 2. The results are shown in Table 8.

[0168] [Table 8]

[0169] An <Antiviral Test 2> was carried out on Examples 2, 3, 5 to 10, 12 to 13 and Comparative Examples 3 to 10, 12, and 13. The results are shown in Table 9.

[0170] [Table 9]

[0171] <Antiviral Test 3> was carried out on Examples 2 to 11, 14 to 15 and Comparative Examples 3 to 11. The results are shown in Table 10.

[0172] [Table 10]

[0173] The results in Tables 4, 5, and 8 show that the coating film of Example 1 exhibits superior antibacterial and antiviral properties compared to the coating films of Comparative Examples 1 and 2.

[0174] The results in Tables 7, 9, and 10 show that the coating film of Example 2 exhibits superior antibacterial and antiviral properties compared to the coating films of Comparative Examples 3 and 4. Comparing Example 2 with Comparative Example 4, it was found that higher antibacterial and antiviral properties were expressed when a coating film was prepared using the composition obtained in the composition preparation, rather than simply mixing a pigment and a fatty acid metal salt when preparing the coating film.

[0175] The results of Examples 1 to 4 and Comparative Examples 1 to 4 in Tables 4 and 5 to 10 show that compositions using various fatty acid metal salts exhibit 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.

[0176] From the results of Examples 5 to 11 and Comparative Examples 5 to 11 in Tables 6, 7, 9, and 10, it was found that the antibacterial and antiviral activities of organic pigments that do not have antibacterial or antiviral properties can be improved by preparing the composition. 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.

[0177] The results of Examples 12 and 13 and Comparative Examples 12 and 13 in Tables 6, 7, and 9 show that the antibacterial and antiviral activities of inorganic pigments that do not have antibacterial or antiviral properties are improved by preparing the composition. Therefore, it can be said that various inorganic pigments can be used as the pigments that constitute the antibacterial and antiviral agents of the present invention.

[0178] From the results of Examples 2, 14, and 15 in Tables 7 and 10, it was found that all of them had high antibacterial and antiviral properties, but as the ratio of neodymium neodecanoate to iron phthalocyanine was increased, the antibacterial and antiviral properties slightly decreased. This is because neodymium neodecanoate is a sticky solid, and as the ratio of neodymium neodecanoate to iron phthalocyanine was increased, the composition aggregated more and was not uniformly dispersed in the coating film, which is thought to have reduced the antibacterial and antiviral properties.

Claims

1. an organic or inorganic pigment; At least a fatty acid metal salt represented by the following general formula (1): 【Chemistry 1】 (In the general formula (1), R is an alkyl group having 8 to 21 carbon atoms (which may contain an alicyclic structure), n is an integer ranging from 1 to 4, and when n is an integer of 2 or more, multiple R's may be the same or different. M is bismuth, neodymium. and lanthanum neodecanoate, cobalt 2-ethylhexanoate, 1. An antibacterial or antiviral agent comprising a fatty acid metal salt selected from the group consisting of:

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

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

4. 3. The antibacterial and antiviral agent according to claim 1, wherein the inorganic pigment is at least one of iron (III) oxide and triiron tetroxide.

5. 3. An ink, a printed matter, a paint, a coating, a plastic, a fiber, a film, or a cosmetic, comprising the antibacterial agent or antiviral agent according to claim 1 or 2.

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