Antibacterial agent and antiviral agent

Abstract

To provide an antibacterial agent and an antiviral agent that exhibit a relatively small change in color tone and improved productivity, are organic chromatic or organic achromatic, and have relatively low health hazards to the human body, and to further provide inks, printed matter, paints, coatings, plastics, fibers, films, and cosmetics containing the antibacterial agent and the antiviral agent.SOLUTION: It has been found that a composition in which an organic pigment and a copper compound are supported acts as an antibacterial agent and an antiviral agent, and that a molded article containing the composition likewise has antibacterial and antiviral properties, thereby solving the above problem.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] In recent years, there has been a strong demand for maintaining the cleanliness of living spaces, and many homes and public rooms have been equipped with air purifiers and disinfectant sprays to maintain a clean environment. However, efforts are also being made to add high added value by adding antibacterial, antiviral, allergen-removing, 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 textile applications, plastic applications, paint applications, and ink applications. In textile applications, methods for imparting antibacterial or antiviral properties include kneading an antibacterial or antiviral agent into fibers and adhering a solution containing an antibacterial or antiviral agent to the fiber surface. While the method of kneading an antibacterial or antiviral agent into fibers is generally considered to have high washing durability, the high temperatures generated during spinning raise concerns about thermal decomposition of organic antibacterial or antiviral agents, and improvements in heat resistance have been desired. Meanwhile, the method of adhering an antibacterial or antiviral agent to the fiber surface generally uses organic antibacterial or antiviral agents, such as quaternary ammonium salts, but has the problem of reduced antibacterial or antiviral properties after washing (Patent Document 1). In paint applications, organic antibacterial or antiviral agents are used, just as in textile applications. However, acrylic / melamine-based paints and the like require a curing process using heat treatment, and organic antibacterial or antiviral agents, which are considered to have low heat resistance, may cause thermal deterioration of the treated surface and object (Patent Document 2). From this perspective, improved heat resistance is desired for applications that require high-temperature treatment. With regard to the content of antibacterial or antiviral agents, they must be effective in relatively small amounts in any application, and an important technical issue is how to efficiently expose the antibacterial or antiviral agent on the surface of fibers, plastics, coatings, etc. (Patent Document 3, Patent Document 4). On the other hand, for applications such as fiber applications, plastic applications, paint applications, and ink applications, colorants are usually contained, and from this viewpoint, there is an example of an antibacterial composition in which antibacterial properties are imparted by sputtering a metal compound onto an organic pigment to coat the surface of the organic pigment with the metal compound (Patent Document 5).However, sputtering powder such as an organic pigment has the problem that the amount that can be processed at one time is small and sputtering takes time, resulting in very low productivity.In addition, the antibacterial composition has the problem that the color of the organic pigment is significantly impaired because the metal compound coats the entire surface of the pigment particles. In the case of inorganic pigments, there is an example of an antibacterial composition in which antibacterial properties are imparted by supporting silver oxide on the surface of the inorganic pigment (Patent Document 6), but the silver oxide itself is usually black to brown, and the silver oxide is nanoparticled to such an extent that no change in hue is observed. However, since silver-based nanoparticles may enter human cells and destroy them, even if even a small amount of silver oxide nanoparticles fall off, they may enter the human body through the skin, raising concerns about their harmful health effects. Therefore, an object of the present invention is to provide an organic chromatic or achromatic antibacterial or antiviral composition that undergoes relatively little change in hue and can be produced with improved productivity, and that is also relatively low in harmfulness to human health. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2013-76188 [Patent Document 2] Japanese Patent Application Publication No. 2017-014401 [Patent Document 3] Japanese Patent Application Laid-Open No. 2006-28453 [Patent Document 4] Japanese Patent Publication No. 2022-93225 [Patent Document 5] Japanese Patent Application Publication No. 8-239302 [Patent Document 6] Special Publication No. 2006-523735 Summary of the Invention [Problem to be solved by the invention]

[0004] The problem to be solved by the present invention is to provide an antibacterial agent or antiviral agent that is an organic chromatic or organic achromatic color with relatively little change in hue, improved productivity, and relatively low hazard to human health. Another object of the present invention is to provide inks, printed materials, paints, coatings, plastics, fibers, films, cosmetics, and the like that contain the antibacterial agent or antiviral agent. [Means for solving the problem]

[0005] As a result of intensive research by the inventors to solve the above-mentioned problems, they discovered that a pigment composition carrying an organic pigment and a copper compound acts as an antibacterial agent and an antiviral agent, and that a molded article containing the composition also has antibacterial and antiviral properties, thereby solving the above-mentioned problems.

[0006] That is, the present invention includes the following.

[0007] [1] An antibacterial agent and an antiviral agent characterized by containing a pigment composition in which a copper compound is supported on an organic pigment or dye. [2] The antibacterial and antiviral agent according to 1, wherein the mass ratio of the organic pigment or dye to the copper compound in the pigment composition is organic pigment:copper compound=99.9:0.1 to 80:20. [3] The antibacterial and antiviral agent according to 1 or 2, characterized in that the organic pigment is at least one compound selected from the group consisting of a phthalocyanine compound, a quinacridone compound, and an isoindoline compound. [4] The antibacterial and antiviral agent according to 1 or 2, characterized in that the copper compound carries at least one compound selected from Cu2Cl(OH)3 and CuO. [5] Inks, printed matter, paints, coatings, plastics, fibers, films, and cosmetics, characterized by containing the antibacterial agent or antiviral agent according to any one of 1 to 4. This provides: [Effects of the Invention]

[0008] 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 agents. Furthermore, they also have antibacterial and antiviral effects 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. DETAILED DESCRIPTION OF THE INVENTION

[0009] The following embodiments of the present invention 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 invention is not significantly deviated from.

[0010] The antibacterial agent and antiviral agent of the present invention will be described below.

[0011] [Organic pigments] Examples of organic pigments that can be used in the present invention include azo-based, phthalocyanine-based, anthraquinone-based, perylene-based, perinone-based, quinacridone-based, thioindigo-based, dioxazine-based, isoindolinone-based, quinophthalone-based, azomethine-based, diketopyrrolopyrrole-based, and isoindoline-based pigments, and examples thereof include Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red No. 223, Red No. 226, Red No. 227, Red No. 228, Red No. 230, Red No. 401, Red No. 405, Red No. 505, Orange No. 203, Orange No. 204, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 401, Blue No. 1, Blue 404, and CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2, 58:4 , 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206 , 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284 , 285, 286, 287, 291, 295, 296, CIPigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36 , 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79, CIPigment Yellow 1, 2, 3, 4, 5, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 169, 170 ,171,172,173,174,175,176,177,179,180,181,182,185,187,188,192,193,194,196,198,199,213,214,CI Examples of organic pigments include CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50; CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, and 59; and CI Pigment Black 1, 7, 31, and 32. These organic pigments may be used alone or in combination of two or more types depending on the desired hue.

[0012] Furthermore, natural pigments may be used as the dyes in the present invention. Examples of natural pigments include carotenoids, anthocyanins, flavonoids, quinones, porphyrins, diketones, betacyanins, and azaphilones, such as β-carotene, norbixin, bixin, capsanthin, lutein, lycopene, crocin, crocetin, astaxanthin, cyanidin acylglucoside, cyanidin, peonidin aglycone, anidin glucoside, delphinidin glucoside, and anthocyanins. Other natural pigments that may be used include rosinin, shisonin, malonylshisonin, pelargonidin acylglucoside, cocoa polyphenols, apigeninidin, luteolinidin, polymerized proanthocyanidins, saflomin, carthamin, carminic acid, laccaic acid, chlorophyll, phycocyanin, curcumin, betanin, isobetanin, ankaflavin, monascorubrin, iridoid glycosides, ester hydrolysates of iridoid glycosides, and eumelanin. These natural pigments may be used alone or in combination depending on the desired hue.

[0013] [Phthalocyanine] In the phthalocyanine, which is one of the organic pigments used in the composition of the present invention, there are no particular limitations on the metal-free phthalocyanine or the central metal, but specific examples include sodium, magnesium, aluminum, silicon, potassium, calcium, titanium, vanadium, manganese, iron, cobalt, nickel, copper, gallium, germanium, zirconium, cadmium, indium, tin, etc. Furthermore, these metals and the phthalocyanine ring may be unsubstituted or may have a substituent such as a halogen, carboxylic acid, a hydroxyl group, or a carbonyl group, and the number of substituents (n) is theoretically possible to be n = 0 to 16, but in order to exhibit the function as a pigment, the phthalocyanine may also have a substituent to the extent that it does not dissolve in water or a solvent.

[0014] Among these, iron phthalocyanine, in which the central metal is iron, copper phthalocyanine, in which the central metal is copper, cobalt phthalocyanine, in which the central metal is cobalt, and aluminum phthalocyanine, in which the central metal is aluminum, have high antibacterial and antiviral effects and are suitable for the pigment composition of the present invention.

[0015] The phthalocyanine used in the present invention is represented by the following general formula:

[0016] [ka] (1) (In the formula, M represents a metal selected from the group consisting of Na2, Mg, Al, Si, K2, Ca, Ti, V, Mn, Fe, Co, Ni, Cu, Ga, Ge, Zr, Cd, and Sn, or an oxymetal or metal halide thereof. R1 to R16 each independently represent a hydrogen atom or a halogen atom.)

[0017] The phthalocyanine used in the present invention exhibits crystalline properties rather than molecular properties when made into a pigment. Specifically, the crystalline properties allow the antibacterial and antiviral effects to extend not only to the area in contact with the phthalocyanine but also to an area slightly distant from the phthalocyanine. In terms of antibacterial and antiviral effects, in the case of dyes, the antibacterial properties are lost 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 slightly covered with resin in a coating film or the like.

[0018] The phthalocyanine may be in a particulate or needle-like shape. There are no particular restrictions on the particle size or aspect ratio, but in general, the particle size of finely divided or refined phthalocyanine is preferably 20 to 200 nm and the aspect ratio is preferably about 1 to 5.

[0019] When phthalocyanine is used as a dye, the decomposition reaction occurs through a redox 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 or the like.

[0020] On the other hand, when phthalocyanine is water-insoluble, a band gap occurs due to its specific crystalline form, and the electron transfer required for the reaction occurs through the valence band and conduction band. When multiple pigments are present, the electrons required for the reaction can move between pigments, similar to hopping conduction, even in the presence of a resin, allowing electrons to be transferred to specific functional groups in bacteria, etc. It is also speculated that the copper compound functions as an electron donor, resulting in photocatalytic activity.

[0021] From the above viewpoint, it is expected that, among metal species of phthalocyanine, metal species in which oxidation-reduction of metal ions is likely to occur in an electrochemical reaction will have higher antibacterial and antiviral properties than metal species in which oxidation-reduction of the phthalocyanine ring is likely to occur.

[0022] [Quinacridone] The quinacridone, which is one of the organic pigments used in the composition of the present invention, is preferably one represented by the following general formula:

[0023] [ka] (2) (wherein X and Y each independently represent a hydrogen atom, a halogen atom, or an alkyl or alkoxy group having 1 to 4 carbon atoms, and m and n each independently represent an integer of 0 to 2.)

[0024] Examples of quinacridones represented by general formula (1) include unsubstituted quinacridone pigments such as CI Pigment Violet 19, dimethylquinacridone pigments such as CI Pigment Red 122, and dichloroquinacridone pigments such as CI Pigment Red 202, CI Pigment Red 207, and CI Pigment Red 209. Furthermore, like phthalocyanine pigments, quinacridone pigments have a certain crystal form, which generates a band gap, and it is known that the transfer of electrons required for the reaction occurs through the valence band or conduction band. When multiple pigments are present, the electrons required for the reaction can move between pigments, similar to hopping conduction, even in the presence of a resin. Therefore, it is expected that the copper compound will function as an electron donor, exhibiting photocatalytic activity and reacting with specific functional groups in bacteria, etc.

[0025] [Isoindolinone] The isoindolinone, which is one of the organic pigments used in the composition of the present invention, is preferably one represented by the following general formula:

[0026] [ka] (3) (In the formula, A1 to A8 each independently represent hydrogen, halogen, or an alkyl group or alkoxy group having 1 to 2 carbon atoms; B represents hydrogen, halogen, or an alkyl group having 1 to 2 carbon atoms; and m represents an integer of 1 to 3. Examples of the isoindolinone represented by the general formula (2) include unsubstituted isoindolinone pigments such as CI Pigment Yellow 173, and chloro-substituted isoindolinone pigments such as CI Pigment Yellow 109 and CI Pigment Yellow 110.

[0027] When converting the organic pigment into a pigment, any of the known and commonly used methods can be used, specifically, a method of kneading and grinding a compound to be the organic pigment together with a water-soluble inorganic salt and a water-soluble organic solvent (solvent salt milling method), a method of heating a compound to be the organic pigment in a solvent in which the compound is insoluble (solvent method), a method of pulverizing using a pigment grinder or a pigment disperser, etc. Examples of the solvent salt milling method include a method in which a compound to be the organic pigment is kneaded and ground together with a water-soluble inorganic salt such as sodium chloride or sodium sulfate and a water-soluble organic solvent such as diethylene glycol or triethylene glycol while heating, and then washed with water. When the solvent method is used, a liquid medium that does not dissolve the compound that will become the organic pigment is selected. As this liquid medium, a liquid medium containing a water-soluble organic solvent as an essential component is preferably used in order to more stably control the crystallization of the compound that will become the organic pigment. When a method for pulverizing the pigment is carried out, for example, a pigment grinder or pigment disperser such as a ball mill, a sand mill, an attritor, a horizontal continuous medium disperser, a kneader, a continuous single-screw kneader, a continuous twin-screw kneader, a three-roll mill, or an open-roll continuous kneader can be used. The pigment grinder or pigment disperser can also be used in the solvent salt milling method.

[0028] [Copper compound] As the starting material for the copper compound used in the present invention, inorganic copper compounds, organic copper compounds, etc. can be used. As the inorganic copper compound, any copper compound can be used, for example, copper chloride (I), copper chloride (II), copper bromide (I), copper bromide (II), copper sulfate, copper nitrate, copper iodate, copper perchlorate, copper oxalate, copper phosphate, copper pyrophosphate, etc. These compounds can be used alone or in combination of two or more. Examples of the copper organic compound that can be used include copper formate, copper acetate, copper propionate, copper citrate, copper oxalate, copper ethoxide, copper isopropoxide, copper butoxide, etc. These compounds may be used alone or in combination of two or more.

[0029] [Acidic compounds] The acidic compound used in the present invention is not essential in the production method of the composition of the present invention, but its use is preferred because it allows a stable pigment composition to be obtained. As the acidic compound, known and commonly used acidic compounds are used, such as hydrochloric acid, sulfuric acid, acetic acid, nitric acid, and phosphoric acid. These compounds may be used alone or in combination of two or more.

[0030] [Alkaline compounds] The alkaline compound used in the present invention is used in the production method of the composition of the present invention to obtain a copper compound supported on an organic pigment. As the alkaline compound, known and commonly used alkaline compounds are used, such as sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, tetrabutylammonium hydroxide, triethylamine, trimethylamine, ammonia, and basic surfactants. These compounds may be used alone or in combination.

[0031] [Pigment composition] The pigment composition of the present invention is an antibacterial and antiviral composition containing a pigment composition in which a copper compound is supported on an organic pigment. The supported state refers to a state in which the copper compound is scattered on the surface of a single organic pigment, and may be scattered uniformly or locally. The composition of the present invention may also contain an organic pigment that does not have a copper compound supported thereon. The copper compound supported on the organic pigment is mainly in the form of CuCl(OH) or CuO, based on the results of X-ray diffraction peak analysis and X-ray fluorescence analysis. However, the pigment composition of the present invention may contain copper compounds other than the above-mentioned copper compounds that are generated during the production process. The particle size of the supported copper compound is about 1 to 100 nm, preferably 2 to 80 nm, and more preferably 5 to 60 nm, and the shape of the supported copper compound may be amorphous, acicular, spherical, or polyhedral. The mass ratio of the organic pigment to the copper compound in the pigment composition of the present invention is organic pigment:copper compound=99.9:0.01 to 70:30, preferably 99.9:0.01 to 80:20, and particularly preferably 99.5:0.5 to 90:10. The above mass ratio of the organic pigment to the copper compound is preferred from the viewpoint of antibacterial and antiviral properties.

[0032] [Method of producing pigment composition] The method for producing a pigment composition of the present invention includes a step of mixing the organic pigment, the starting material, water, and an acidic and alkaline compound. For example, one method includes first mixing and stirring the organic pigment in water, then mixing and stirring the starting material, an aqueous solution of the starting material, or an acidic aqueous solution obtained by adding an acidic compound to the starting material, or an acidic aqueous solution obtained by adding an acidic compound to an aqueous solution of the starting material, and then adding an alkaline compound or an aqueous solution of the alkaline compound while stirring, or adding it dropwise. Alternatively, the organic pigment can be mixed and stirred in the acidic aqueous solution, and then the starting material can be mixed and stirred, and then an alkaline substance or an aqueous solution of the alkaline substance can be mixed and stirred.

[0033] In the method for producing a pigment composition of the present invention, the starting material is preferably in a completely dissolved state before the alkaline substance is added so that the starting material is supported on the entire organic pigment. In the method for producing a pigment composition of the present invention, the medium used to disperse the organic pigment may be water alone, but may also contain an organic solvent if necessary. Examples of the organic solvent include alcoholic solvents such as methanol, ethanol, 1-propanol, 2-propanol, and 1-butanol; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; dimethylformamide, N-methyl-2-pyrrolidone, and tetrahydrofuran. These organic solvents may be used alone or in combination. If no organic solvent is used, the organic pigment, either directly or after being mixed with water, may be subjected to plasma treatment, corona treatment, high-pressure pulverization (dispersion), bead pulverization (dispersion), or other treatments.

[0034] This mixing step results in the copper compound being supported on the organic pigment. The copper compound may be supported uniformly on the surface of the organic pigment, or may be segregated on a portion of the surface of the organic pigment. The step following the mixing step is a separation step between the solid and liquid components, which may include, for example, filtration, centrifugation, and sedimentation. The solid component obtained in the separation step is optionally washed with water, crushed, dried, classified, or the like, to obtain the composition of the present invention. The resulting pigment composition of the present invention can be further heat-treated. The heat treatment temperature is in the range of 150 to 400°C, but from the viewpoint of preventing discoloration, it is preferably in the range of 200 to 300°C. Since it is said that Cu2Cl(OH)3 changes to CuO at 220°C or higher, heat treatment at 220°C or higher increases the proportion of CuO.

[0035] The mass ratio of the organic pigment to the copper compound in the pigment composition of the present invention is organic pigment:copper compound=99.9:0.01 to 70:30, preferably 99.9:0.01 to 80:20, and particularly preferably 99:1 to 90:10. The above-mentioned ratio of the organic pigment to the copper compound is preferred from the viewpoints of antibacterial properties, antiviral properties, and hue.

[0036] The antibacterial agent and antiviral agent of the present invention are a pigment composition in which a copper compound is supported on an organic pigment or dye, and examples of other components other than the pigment composition include the following. The ratio of the pigment composition to the other components can be any ratio with the pigment composition as an essential component, as long as antibacterial and antiviral properties are exhibited; however, from the viewpoint of antibacterial and antiviral properties, the ratio of the pigment composition to the entire antibacterial agent or antiviral agent is preferably 20 mass % or more, and particularly preferably 50 mass % or more.

[0037] 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.

[0038] 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, and Legionella; and gram-positive bacteria such as Staphylococcus aureus and Clostridium bacteria. Examples of fungi include yeasts such as Candida, Rhodotorula, and baker's yeast; and molds such as red mold and black mold.

[0039] In the present invention, the viruses to be treated against are not particularly limited, and may be any of known enveloped viruses (viruses with an envelope) and non-enveloped viruses (viruses without an envelope).

[0040] Examples of the enveloped viruses include coronavirus, influenza virus, rubella virus, Ebola virus, measles virus, varicella-zoster virus, herpes virus, mumps virus, arbovirus, respiratory syncytial 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, and lyssavirus.

[0041] 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.

[0042] (Antibacterial effect) Examples of indicators of antibacterial activity include bacterial growth tests using culture kits and antibacterial tests specified in JIS standards.

[0043] The main purpose of culture kits 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 antibacterial activity, a certain amount of bacteria and fungi are killed or their growth is suppressed, preventing the occurrence of colonies or delaying the occurrence of colonies. Bacterial growth tests using culture kits can be evaluated by regular observation of the phenomenon. 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, as well as common live bacteria containing the bacteria and fungi. 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.), etc. Antibacterial testing specified in JIS standards primarily targets typical gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Moraxella, as well as gram-positive bacteria such as Staphylococcus aureus, MRSA, and Streptococcus pyogenes. The test bacterial solution is inoculated into a sample, and the sample is placed on a film or glass plate and exposed to light for a set period of time, or allowed to stand in the dark. The collected bacterial solution is then diluted and cultured on an agar medium. After culture, the number of colonies produced is compared to determine the antibacterial activity value. Specific methods include the bacterial solution absorption method, transfer method, bacterial transfer method, and halo method, as specified in JIS R1702 (antibacterial test method for photocatalytic antibacterial products, antibacterial effect), JIS R1752 (antibacterial test method for visible light-responsive photocatalytic products, antibacterial effect), JIS L1902 (antibacterial test method and antibacterial effect for textile products), JIS Z2801 (antibacterial test method and antibacterial effect for antibacterial products), and JIS L1902 (antibacterial test method and antibacterial effect for textile products).

[0044] (Antiviral effect) Examples of indicators of antiviral activity include antiviral tests specified in JIS and ISO standards. - Antiviral tests specified in JIS and ISO standards primarily target typical enveloped influenza viruses, non-enveloped feline caliciviruses, or bacteriophages. In general, a virus or bacteriophage solution is inoculated into a sample, and the solution is placed in close contact with a film or glass and exposed to light or left in the dark for a certain period of time. The collected solution is then diluted and cultured on an agar medium. After culturing, the number of plaques is compared to determine the antiviral activity value. Alternatively, a virus solution is inoculated into a sample, and the sample is placed in close contact with a film or glass through the virus solution and exposed to light or left in the dark for a certain period of time. The virus solution on the sample is then washed off and collected. The virus infectivity is then compared to determine the antiviral activity value. Specifically, examples of antiviral tests include 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, and JIS L1922 Antiviral test method for textile products.

[0045] <Evaluation of antibacterial properties of coating film> Antibacterial tests were conducted using the following method against Staphylococcus aureus (NBRC 12732) and Escherichia coli (NBRC 3972). 0.4 ml of test bacterial solution was inoculated onto a 5 cm x 5 cm coating film that had been cleaned by ultraviolet irradiation, and the bacterial solution was left in a dark place for 24 hours with the film or glass attached to it. The collected bacterial solution 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 : Average logarithm of viable bacteria count after 24 hours for unprocessed products, A t(The mean logarithmic value of the number of live bacteria on the processed product after 24 hours) The processed product is a coating film made from a dispersion containing the test substance, and the unprocessed product is a PET film. As a guideline for antibacterial activity, for example, JIS Z 2801:2021 Antibacterial Products - Antibacterial Testing Methods - Antibacterial Effect specifies that the criterion for antibacterial effect is 2.0 or higher. An antibacterial activity value of 2.0 means that the processed product inhibited bacterial growth by 99% after testing compared to the unprocessed product. However, this does not necessarily mean that bacteria will not grow.

[0046] <Evaluation of antiviral properties of coating film> An antiviral test was conducted using bacteriophage Qβ (NBRC 20012, host E. coli (NBRC 106373)) using the following method. A test phage solution was inoculated onto a 5cm x 5cm coating film, and the phage solution was left in a dark place for 4 hours while attached to a film or glass. The collected phage solution was then diluted and cultured on an agar medium. After the culture, the antiviral activity value was calculated by comparing the number of colonies that appeared. 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 from a dispersion containing the test substance, and the unprocessed product is a PET film. For example, an antiviral activity value of 2.0 means that the processed product inhibited phage proliferation by 99% after the test compared to the unprocessed product. However, this does not necessarily mean that phage proliferation did not occur.

[0047] By utilizing the antibacterial agent and antiviral agent of the present invention, it is possible to provide inks, printed materials, paints, coatings, plastics, fibers, films, cosmetics, etc. The uses detailed below are examples, and the antibacterial agent and antiviral agent of the present invention can be used for any application having antibacterial, antifungal, sterilizing, or antiviral properties.

[0048] (Ink applications) The antibacterial and antiviral agents of the present invention can provide printing inks having antibacterial and antiviral properties. The printing inks can be prepared by mixing the antibacterial and antiviral agents of the present invention with various known and commonly used binder resins, various solvents, various additives, and the like, according to conventional preparation methods. Specifically, liquid inks can be prepared by preparing a liquid ink base ink having a high pigment concentration and then using various binders, various solvents, various additives, and the like.

[0049] The antibacterial and antiviral agents of the present invention can be used to produce PU inks and NC inks with antibacterial and antiviral properties, and are suitable as organic compositions for gravure printing inks and flexographic printing inks. PU inks consist of PU resins, pigments, solvents, and various additives, while NC inks consist of NC resins, pigments, solvents, and various additives. PU resins are not particularly limited as long as they have a urethane structure in their skeleton, and include polyurethanes, polyurethane polyureas, and the like. Examples of the solvents include 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 t-butanol, and propylene glycol monoethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol mono-n-propyl ether. Examples of suitable solvents include (poly)alkylene glycol monoalkyl ether solvents such as ethylene 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, and amphoteric surfactants, rosins such as gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleated rosin, hardened rosin, and phthalate alkyd resin, pigment derivatives, dispersants, wetting agents, adhesion aids, leveling agents, antifoaming agents, antistatic agents, trapping agents, antiblocking agents, and wax components.

[0050] When the antibacterial agent or antiviral agent of the present invention is used as a printing ink, the printing ink using the composition of the present invention prepared as described above can be diluted with ethyl acetate, a polyurethane varnish, or a polyamide varnish. A known, commonly used method can be used to prepare the printing ink.

[0051] (Paint application) When the antibacterial agent and antiviral agent of the present invention are used as a paint having antibacterial and antiviral activity, 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.

[0052] 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. Suitable solvents include polar solvents such as propionates, alcohols, ethers, ketones, nitrogen compounds, lactones, and water, which are soluble in water.

[0053] In addition, when the pigment additive and / or composition is dispersed or mixed in a liquid resin to form a resin composition for coating, conventional additives such as dispersants, fillers, coating aids, driers, plasticizers, and / or auxiliary pigments can be used. This can be achieved by dispersing or mixing each component alone or several together, by collecting all the components, or by adding them all at once.

[0054] Dispersing machines for dispersing antibacterial and antiviral agents containing compositions prepared for specific applications as described above include, but are not limited to, known dispersing machines such as dispersers, homomixers, paint conditioners, scandex, bead mills, attritors, ball mills, two-roll mills, three-roll mills, and pressure kneaders. The composition is dispersed by adding resins and solvents to achieve a viscosity that allows dispersion using these dispersing machines. The resulting high-concentration paint base has a solids content of 5 to 20%, and is further mixed with resins and solvents for use as a paint.

[0055] (Plastic applications) The antibacterial and antiviral agents of the present invention can also be used in plastic applications having antibacterial and antiviral effects. When obtaining plastic molded products, 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 and antiviral agents of the present invention can be used by kneading them into these resins using a conventionally known method.

[0056] (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 compositions of the present invention can be used in various types of cosmetics.

[0057] The cosmetic product may be of any type as long as it can effectively exhibit its function. The cosmetic product may be a lotion, cream gel, spray, etc. Examples of the cosmetic product include skin care products such as face washes, makeup removers, toners, serums, packs, protective emulsions, protective creams, whitening cosmetics, and UV protection cosmetics; makeup products such as foundations, face powders, makeup bases, lipsticks, eye makeup, blushers, and nail enamel; hair care products such as shampoos, hair rinses, hair treatments, hair styling products, permanent wave agents, hair dyes, and hair growth agents; and body care products such as body cleansers, deodorants, and bath additives.

[0058] The amount of the antibacterial agent or antiviral agent of the present invention used in the cosmetic product can be appropriately determined depending on the type of cosmetic product. The content in the cosmetic product is usually in the range of 0.1 to 99% by mass, and generally, the amount is preferably in the range of 0.1 to 10% by mass. On the other hand, in 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 antibacterial agent or antiviral agent of the present invention contained in the cosmetic product is within the above range, the cosmetic product can effectively exhibit its functions, such as coloring ability, while also maintaining the functions required of the cosmetic product.

[0059] The cosmetics may contain, depending on the type of cosmetic, the antibacterial agent or antiviral agent of the present invention as well as other ingredients acceptable as cosmetic ingredients, such as carriers, pigments, oils, sterols, amino acids, moisturizers, 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, humectants, moisturizers, minerals, viscosity adjusters, flow adjusters, keratolytic agents, 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, anti-acne 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.

[0060] The cosmetic product can be produced by mixing the antibacterial agent, antiviral agent of the present invention and other cosmetic ingredients. 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.

[0061] 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. This adjustment can be made by adjusting the type of copper compound or controlling the dispersion conditions depending on the type of resin used in the paint or plastic.

[0062] 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 pigment composition in which a copper compound is supported in the form of nanoparticles on the surface of a pigment having organic semiconducting properties, such as phthalocyanine or quinacridone. The reason for this is unclear, but it is speculated that when either the pigment composition in which a copper compound is supported on the surface of the pigment having organic semiconducting properties, or the copper compound that is not supported, 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. [Example]

[0063] 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."

[0064] <Antibacterial test 1> With reference to JIS R 1752:2020, antibacterial tests were conducted using the coating film against Staphylococcus aureus (NBRC 12732) as a representative of gram-positive bacteria and Escherichia coli (NBRC 3972) as a representative of gram-negative bacteria using the following method. 0.1 ml of test bacterial solution was inoculated onto a 5 x 5 cm coating film that had been cleaned by heating in a dry heat sterilizer, and the bacterial solution was left in contact with a film or glass in a dark place for 8 hours. The collected bacterial solution was then diluted and cultured on an agar medium. After 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: Average logarithm of viable bacteria count after 8 hours for unprocessed products, A t (The mean logarithmic value of the number of live bacteria on the processed product after 8 hours) The processed product is a coating film made from a dispersion containing the test substance, and the unprocessed product is a coating film made from a solution consisting of synthetic resin, polyurethane resin, and solvent.

[0065] <Antibacterial test 2> With reference to JIS R 1752:2020, antibacterial tests were conducted using the coating film against Staphylococcus aureus (NBRC 12732) as a representative of gram-positive bacteria and Escherichia coli (NBRC 3972) as a representative of gram-negative bacteria using the following method. A 5 x 5 cm coating film that had been sterilized by heating in a dry heat sterilizer was inoculated with 0.1 ml of test bacterial solution, and the bacterial solution was placed in close contact with a film or glass and irradiated with light (white fluorescent lamp (FL20SSW / 18, MITSUBISHI), visible light 500 lx, sharp cut filter Type A (N113, cuts wavelengths of 400 nm or less)) and left to stand for 8 hours. The collected bacterial solution was then diluted and cultured on an agar medium. After culture, the antibacterial activity value was determined by comparing the number of colonies that appeared. The calculation formula was 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 : Average logarithm of viable bacteria count after 8 hours for unprocessed products, A t (The mean logarithmic value of the number of live bacteria on the processed product after 8 hours) The processed product is a coating film made from a dispersion containing the test substance, and the unprocessed product is a coating film made from a solution consisting of synthetic resin, polyurethane resin, and solvent.

[0066] <Antiviral test 1> With reference to JIS R 1756:2020, antiviral tests were conducted using the coating film of Example 1 against representative viruses, bacteriophage Qβ (NBRC 20012, host Escherichia coli (NBRC 106373)) and bacteriophage Φ6 (NBRC105899, host Pseudomonas syringae (NBRC14084)), using the following method. A test phage solution was inoculated onto a 5 x 5 cm coating film, and the phage solution was left in a dark place for 4 hours while attached to a film or glass. The collected phage solution was then diluted and cultured on an agar medium. After the culture, the antiviral activity value was calculated by comparing the number of colonies that appeared. 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 titer is expressed as the infectivity titer of the processed product after standing in a dark place for 4 hours.) The processed product is a coating film made from a dispersion containing the test substance, and the unprocessed product is a coating film made from a solution consisting of synthetic resin, polyurethane resin, and solvent.

[0067] <Antiviral test 2> With reference to JIS R 1756:2020, antiviral tests were conducted using the coating film of Example 1 against representative viruses, bacteriophage Qβ (NBRC 20012, host Escherichia coli (NBRC 106373)) and bacteriophage Φ6 (NBRC105899, host Pseudomonas syringae (NBRC14084)), using the following method. A 5 x 5 cm coating was inoculated with a test phage solution, and the phage solution was placed in close contact with a film or glass and irradiated with light (white fluorescent lamp (FL20SSW / 18, MITSUBISHI), visible light 500 lx, sharp cut filter Type A (N113, cuts wavelengths of 400 nm or less)) and left to stand for 4 hours. The recovered phage solution was then diluted and cultured on an agar medium. After culture, the antiviral activity value was determined by comparing the number of colonies that emerged. The calculation formula is VD :Antiviral activity value (bright light): [V L =Log(B L )-Log(C L )](L: light place, B L : Infectivity value of unprocessed product after standing for 4 hours in a bright place, C L (The infectivity titer is expressed as the infectivity titer of the processed product after standing for 4 hours in a bright place.) The processed product is a coating film made from a dispersion containing the test substance, and the unprocessed product is a coating film made from a solution consisting of synthetic resin, polyurethane resin, and solvent.

[0068] The pigments used in Examples 1 to 10 and Comparative Examples 1 to 4 are listed below.

[0069] (iron phthalocyanine) The iron phthalocyanine used was product name P-26 (manufactured by Sanyo Pigment Co., Ltd.).

[0070] (copper phthalocyanine) The copper phthalocyanine used was CI Pigment Blue 15:3, product name: FASTOGEN BLUE PA5380 (manufactured by DIC Corporation).

[0071] (Quinacridone) The quinacridone used was CI Pigment Violet 19, product name: FASTOGEN SUPER RED 500RS (manufactured by DIC Corporation).

[0072] (Isoindolinone) The isoindolinone used was CI Pigment Yellow 110, product name: FASTOGEN SUPER YELLOW GRO (manufactured by DIC Corporation).

[0073] The copper compounds used in Examples 1 to 10 are listed below.

[0074] (copper(I) chloride) Copper(I) chloride was manufactured by Kanto Chemical Co., Ltd.

[0075] (Copper(II) chloride dihydrate) Copper (II) chloride dihydrate was manufactured by Kanto Chemical Co., Ltd.

[0076] (Preparation of pigment composition) Based on the formulations in Table 1, pigment compositions 1 to 9 were prepared according to the following recipes.

[0077] [Table 1]

[0078] In a 500 mL beaker, the pigment and 15.0 g of ethanol (Kanto Chemical Co., Inc.) were mixed and stirred. An additional 300 g of water was added, and the pH was adjusted to 2 using 5% hydrochloric acid. To the resulting solution, a solution prepared by mixing and stirring a copper compound and 30 g of water in a separate 100 mL beaker and adjusting the pH to 2 using 5% hydrochloric acid was added. After stirring for 10 minutes, the pH was adjusted to 8 using a 5% aqueous sodium hydroxide solution. After stirring for another hour, the mixture was filtered, washed, dried, and pulverized to obtain a composition. The 5% hydrochloric acid was prepared using hydrochloric acid (purity 35 to 37%, manufactured by Kanto Chemical Co., Ltd.), and the 5% aqueous sodium hydroxide solution was prepared using sodium hydroxide (manufactured by Kanto Chemical Co., Ltd.).

[0079] Based on the formulations in Table 2, coating films of Examples 1 to 10 and Comparative Examples 1 to 4 were prepared according to the following recipes.

[0080] [Table 2]

[0081] A 100 mL plastic bottle was charged with a pigment, a synthetic resin (product name: V343-306SA (manufactured by DIC Graphics Corporation, solids concentration: 25%, solvent weight ratio: methyl ethyl ketone / ethyl acetate / toluene = 35 / 20 / 20), a polyurethane resin (product name: Sanprene IB-D12 (manufactured by Sanyo Chemical Industries, Ltd., solids concentration: 30%, solvent weight ratio: methyl ethyl ketone / isopropanol = 47 / 23), solvents (toluene (manufactured by Kanto Chemical Co., Ltd.), methyl ethyl ketone (manufactured by Kanto Chemical Co., Ltd.)), and 40 g of 1 / 8-inch steel beads. The bottle was then shaken in a paint conditioner for 30 minutes to obtain a dispersion. The obtained dispersion was applied to an 188 μm PET film using a No. 6 bar coater, dried with a dryer, and further dried at 150°C for 15 minutes to obtain the coating films of Examples 1 to 10 and Comparative Examples 1 to 4.

[0082] The resulting coating films of Examples 1 to 10 and Comparative Examples 1 to 4 were subjected to <Antibacterial Test 1> and <Antiviral Test 1>, and the results are shown in Table 3. Activity values ​​of 0.5 or less were marked "x." The amount added refers to the ratio of the amount of composition or pigment added to the resin solid content.

[0083] [Table 3]

[0084] The results in Table 3 show that Example 1 had higher activity values ​​than Comparative Example 1, Examples 2 to 4 than Comparative Example 2, Examples 5 to 8 than Comparative Example 3, and Examples 9 and 10 than Comparative Example 4 for bacteriophage Qβ, bacteriophage Φ6, Escherichia coli, and Staphylococcus aureus, and that activity was improved by supporting a copper compound.

[0085] Next, the obtained coating films of Examples 3, 4, 6, 7, 9, and 10 and Comparative Examples 2 to 4 were subjected to <Antibacterial Test 2> and <Antiviral Test 2>, and the results are shown in Table 4. Activity values ​​of 0.5 or less were marked with "X." The amount added refers to the ratio of the amount of composition or pigment added to the resin solid content.

[0086] [Table 4]

[0087] The results in Table 4 show that Examples 3 and 4 had higher activity values ​​for bacteriophage Qβ, bacteriophage Φ6, Escherichia coli, and Staphylococcus aureus than Comparative Example 2, Examples 6 and 7 had higher activity values ​​for Escherichia coli, and Staphylococcus aureus than Comparative Example 3, and that the activity was improved by supporting a copper compound.

[0088] In Example 7, the activity values ​​in Table 4 are higher than those in Table 3, and the difference in activity values ​​is particularly large for bacteriophage Qβ, Escherichia coli, and Staphylococcus aureus, which indicates that light irradiation is effective.

Claims

1. An antibacterial agent and an antiviral agent, characterized by containing a pigment composition in which a copper compound is supported on an organic pigment or dye.

2. 2. The antibacterial and antiviral agent according to claim 1, wherein the mass ratio of the organic pigment or dye to the copper compound in the pigment composition is organic pigment:copper compound=99.9:0.1 to 80:

20.

3. 3. The antibacterial and antiviral agent according to claim 1, wherein the organic pigment is at least one compound selected from the group consisting of a phthalocyanine compound, a quinacridone compound, and an isoindoline compound.

4. The copper compound contains at least Cu ２ Cl(OH) ３ 3. The antibacterial and antiviral agent according to claim 1, wherein the agent supports one or more compounds selected from the group consisting of CuO and CuO.

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

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