JP2024059262A - Antibacterial and antiviral resin composition, cured coating film, laminate and molded body - Google Patents

Abstract

[Problem] To provide an antibacterial and antiviral resin composition, a cured coating film, a laminate, and a molded article having high hardness and antibacterial and antiviral activity. [Solution] An antibacterial and antiviral resin composition containing an antibacterial and antiviral agent and a polyfunctional (meth)acrylate compound, wherein the antibacterial and antiviral agent is one or more selected from the group consisting of a fatty acid metal salt, a metal complex of a heteroatom-containing ligand and a metal ion, and a metal complex of a heteroatom-containing ligand and a fatty acid metal salt, and the antibacterial and antiviral resin composition contains 0.1 to 4 parts by mass of the metal derived from the antibacterial and antiviral agent per 100 parts by mass of the resin solids. [Selected Figure] None

Description

The present invention relates to an antibacterial and antiviral resin composition, a cured coating film, a laminate, and a molded body.

The spread of COVID-19 has led to a rapid increase in people's awareness of hygiene. There is also a growing global need for "antibacterial and antiviral" products for everyday items to reduce the possibility of infection with pathogens and viruses. For example, there is a strong demand for antibacterial and antiviral surfaces on the exterior and touch panels of smartphones, handrails, doorknobs, washbasins, various push buttons such as elevator buttons, and the interiors of public transportation, as these are expected to be used multiple times throughout the day.

Known antibacterial and antiviral agents include photocatalyst-based ( _TiO2 , etc.) and metal-based (Ag, etc.) agents (for example, Patent Document 1). These metals or metal compounds are directly applied to the target object, or mixed with a binder resin to form a coating composition, which is then applied to the target object.

JP 2019-182846 A

When inorganic metal compounds, which are conventional antibacterial and antiviral agents, are directly applied to an object, there are problems in that the color of the object changes and that the object feels rough to the touch. Even when a coating composition is made of an inorganic metal compound and a binder resin, the coating layer obtained from the coating composition has a cloudy color due to the inorganic metal compound, and when the binder resin is a transparent resin, there are problems in that its transparency is impaired. In addition, in compositions containing inorganic metal compounds, the inorganic compound is generally in the form of a powder, so a dispersion process is required, which is a problem from the viewpoint of productivity.

The problem that the present invention aims to solve is to provide an antibacterial and antiviral resin composition capable of forming a cured coating film having high hardness and antibacterial and antiviral activity, a cured coating film, a laminate, and a molded body.

As a result of intensive research to solve the above problems, the present inventors have found that an antibacterial, antiviral resin composition containing an antibacterial, antiviral agent and a polyfunctional (meth)acrylate compound, in which the content of metal derived from the antibacterial, antiviral agent is within a specific range, can form a cured coating film, laminate, and molded article that have high hardness and antibacterial and antiviral activity, and have completed the present invention.

（前記一般式（３－１）および（３－２）中、
Ｒ^３１１～Ｒ^３１６およびはＲ^３２１～Ｒ^３２６は、それぞれ独立に、炭素原子数１～２２のアルキル基又は炭素原子数１～２２のアルコキシ基である。）
［４］前記多官能（メタ）アクリレート化合物が、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、アクリル（メタ）アクリレート、及びウレタン（メタ）アクリレートから選択される１種以上である［１］～［３］のいずれかの抗菌抗ウイルス性樹脂組成物。
［５］［１］～［４］のいずれかの抗菌抗ウイルス性樹脂組成物の硬化物からなる硬化塗膜。
［６］前記硬化塗膜が透明である［５］の積層体。
［７］［１］～［４］いずれかの抗菌抗ウイルス性樹脂組成物を成形した成形体。 That is, the present invention relates to the following.
[1] An antibacterial and antiviral resin composition containing an antibacterial and antiviral agent and a polyfunctional (meth)acrylate compound, wherein the antibacterial and antiviral agent is one or more selected from the group consisting of a fatty acid metal salt, a metal complex of a heteroatom-containing ligand and a metal ion, and a metal complex of a heteroatom-containing ligand and a fatty acid metal salt, and the antibacterial and antiviral resin composition contains a metal derived from the antibacterial and antiviral agent in an amount of 0.1 to 4 parts by mass per 100 parts by mass of the resin solids content.
[2] The antibacterial and antiviral resin composition according to [1], wherein the antibacterial and antiviral agent is an aluminum complex or a barium complex.
[3] The antibacterial and antiviral resin composition according to [2], wherein the aluminum complex is a compound represented by the following general formula (3-1) or (3-2):

(In the general formulas (3-1) and (3-2),
R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ are each independently an alkyl group having 1 to 22 carbon atoms or an alkoxy group having 1 to 22 carbon atoms.
[4] The antibacterial and antiviral resin composition according to any one of [1] to [3], wherein the polyfunctional (meth)acrylate compound is at least one selected from pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, acrylic (meth)acrylate, and urethane (meth)acrylate.
[5] A cured coating film comprising a cured product of the antibacterial and antiviral resin composition according to any one of [1] to [4].
[6] The laminate according to [5], wherein the cured coating film is transparent.
[7] A molded article obtained by molding the antibacterial and antiviral resin composition according to any one of [1] to [4].

The present invention provides an antibacterial and antiviral resin composition capable of forming a cured coating film having high hardness and antibacterial and antiviral activity, a cured coating film, a laminate, and a molded article.

One embodiment of the present invention will be described below. The present invention is not limited to the following embodiment, and can be modified as appropriate without impairing the effects of the present invention.

<<Antibacterial and antiviral resin composition>>
The antibacterial and antiviral resin composition of the present invention (hereinafter also simply referred to as "composition") contains at least an antibacterial and antiviral agent and a polyfunctional (meth)acrylate compound.

[Antibacterial and antiviral agents]
The antibacterial and antiviral agent is one or more selected from the group consisting of a fatty acid metal salt, a metal complex of a heteroatom-containing ligand and a metal ion, and a metal complex of a heteroatom-containing ligand and a fatty acid metal salt, and the metals in the fatty acid metal salt, the metal complex of a heteroatom-containing compound ligand and a metal ion, and the metal complex of a heteroatom-containing compound ligand and a fatty acid metal salt are each independently 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.

The antibacterial and antiviral agent takes the form of a fatty acid metal salt or metal complex, and due to the antibacterial and antiviral properties of the metal and the high compatibility of the fatty acid or complex ligand with organic matter, when added to a composition containing a polyfunctional (meth)acrylate compound, etc., it is believed that the antibacterial and antiviral agent can impart antibacterial and antiviral properties to the resulting cured coating film and at the same time reduce the impact on the appearance of the cured coating film, such as the loss of transparency caused by the antibacterial and antiviral agent.

In the present invention, "antibacterial" means 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 the effect of reducing the number of viruses, the effect of inactivating viruses, the effect of reducing the infectivity of viruses, etc.

The bacteria to be treated with antibacterial agents in the present invention 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.

The viruses that are the target of antiviral treatment in the present invention are not particularly limited, and may be any of the known enveloped viruses (viruses that have an envelope) and non-enveloped viruses (viruses that do not have an envelope).

Examples of the enveloped viruses include coronavirus, influenza virus, rubella virus, Ebola virus, measles virus, chickenpox/shingles 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.

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.

The following describes the antibacterial and antiviral agents that can be used in the antibacterial and antiviral resin composition of the present invention.

(Fatty acid metal salts)
An example of a fatty acid metal salt that can be used as an antibacterial and antiviral agent is a compound represented by the following general formula (1).

（前記一般式（１）中、
Ｒ^１は、水素原子または炭素原子数１～２１のアルキル基であり、
ｎ１は、１～４の範囲の整数であり、
Ｍ^１は、リチウム、ナトリウム、カリウム、ルビジウム、セシウム、ホウ素、マグネシウム、アルミニウム、カルシウム、マンガン、鉄、コバルト、ニッケル、スズ、アンチモン、銅、銀、亜鉛、モリブデン、バナジウム、ストロンチウム、ジルコニウム、バリウム、ビスマス、鉛、金、白金又はレアアースである。）

(In the general formula (1),
R ¹ is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms;
n1 is an integer ranging from 1 to 4;
^M1 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.

In the general formula (1), when n1 is an integer of 2 or more, multiple R ^1s may be the same or different.

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

The alkyl group having 1 to 21 carbon atoms represented by R ¹ corresponds to a carboxylic acid residue obtained by removing a carboxyl group (COOH) from a carboxylic acid having 1 to 22 carbon atoms represented by R ¹ COOH 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.

From the viewpoint of adhesion to a substrate, which will be described later, the alkyl group having 1 to 21 carbon atoms for ^R1 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.

^M1 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.
When the metal of the fatty acid metal salt is bismuth, neodymium or magnesium, discoloration due to the addition of the antibacterial and antiviral agent can be made less likely to occur.

In the present invention, rare earth means one or more selected from scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and lutetium (Lu).

n1 is a numerical value determined by the ionic valence of the metal atom of ^M1 . For example, if ^M1 is boron, n1 is 3, and if ^M1 is cobalt, n1 is 2.

The fatty acid metal salt 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 (2).

（前記一般式（２）中、
Ｒ^２は、水素原子または炭素原子数１～２１のアルキル基であり、
Ｍ^２は、ホウ素、マグネシウム、アルミニウム、カルシウム、マンガン、鉄、コバルト、ニッケル、スズ、アンチモン、銅、亜鉛、モリブデン、バナジウム、ストロンチウム、ジルコニウム、バリウム、ビスマス、鉛、金、白金又はレアアースである。）

(In the general formula (2),
^R2 is a hydrogen atom or an alkyl group having 1 to 21 carbon atoms;
^M2 is boron, magnesium, aluminum, calcium, manganese, iron, cobalt, nickel, tin, antimony, copper, zinc, molybdenum, vanadium, strontium, zirconium, barium, bismuth, lead, gold, platinum or rare earth.

In the general formula (2), the alkyl group having 1 to 21 carbon atoms of ^R2 is the same as the alkyl group having 1 to 21 carbon atoms of ^R1 in the general formula (1). Similarly, in the general formula (2), the metal of ^M2 is the same as the metal of ^M1 in the general formula (1).

When a fatty acid metal salt is used as the antibacterial and antiviral agent, a single fatty acid metal salt may be used, or two or more fatty acid metal salts having different structures may be used.

Fatty acid metal salts can be produced by known methods, or commercially available products may be used.

(Metal Complex)
The metal complex of a heteroatom-containing ligand and a metal ion and the metal complex of a heteroatom-containing ligand and a fatty acid metal salt that can be used as the antibacterial and antiviral agent are compounds in which a metal ion or a fatty acid metal salt and a heteroatom-containing ligand form a complex through a coordinate bond.

As the metal ion with which the heteroatom-containing ligand forms a metal complex, the same metal ion as that of the fatty acid metal salt explained as the antibacterial and antiviral agent of the present invention can be used.
As the fatty acid metal salt in which the heteroatom-containing ligand forms a metal complex, the same fatty acid metal salts as those explained as the antibacterial and antiviral agent of the present invention can be used.

The heteroatom-containing ligand that forms the metal complex may be a ligand having one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and phosphorus in the molecule. Examples of the heteroatom-containing ligand include N-methylmorpholine, pyridine, 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,4-diazabicyclo[2.2.2]octane (DABCO), 4-dimethylaminoamine (DMAP), dicyandiamide (DICY), tri-n-butylamine, dimethylbenzylamine, butylamine, 1,2-propanediamine, 1,2-cyclohexanediamine, octylamine, monoethanolamine, diethanolamine, triethanolamine, dimethylbenzylamine, butylamine, 1,2-propanediamine, 1,2-cyclohexanediamine, octylamine, monoethanolamine, diethanolamine, triethanolamine, dimethylbenzylamine, dimethyl ... amine, 2-[[(2-dimethylamino)ethyl]methylamino]ethanol, picolinic acid, 2,2'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenol, imidazole, 1-methylimidazole, 2-methylimidazole, 4-methylimidazole, 2,4-dimethylimidazole, 1,4-diethylimidazole, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-(N-phenyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropyltrimethoxysilane, 3 amine compounds such as -(2-aminoethyl)aminopropylmethyldimethoxysilane, tetramethylammonium hydroxide, 8-quinolinol, 5-chloro-8-quinolinol, 2,2'-bipyridyl and its derivatives, 2,2'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenol and its derivatives, and 2,2'-methylenebis[6-(2h-benzotriazol-2-yl)-4-tert-octylphenol]; quaternary ammonium salts such as trioctylmethylammonium chloride and trioctylmethylammonium acetate; Phosphine compounds such as trimethylphosphine, tributylphosphine, and triphenylphosphine; phosphonium salts such as tetramethylphosphonium chloride, tetraethylphosphonium chloride, tetrapropylphosphonium chloride, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, trimethyl(2-hydroxypropyl)phosphonium chloride, triphenylphosphonium chloride, and benzylphosphonium chloride; and sulfur-based compounds such as thiolactic acid, 2-aminothiophenol, and 2,2'-dithiodianiline.

The heteroatom-containing ligand is preferably one or more amine ligands selected from picolinic acid, 2-{[(2-dimethylamino)ethyl]methylamino}ethanol, 1,2-propanediamine, 1,2-cyclohexanediamine, monoethanolamine, diethanolamine, triethanolamine, imidazole, 1-methylimidazole, 2-methylimidazole, 4-methylimidazole, 2,4-dimethylimidazole, 1,4-diethylimidazole, 8-quinolinol, 5-chloro-8-quinolinol, 2,2'-bipyridyl and its derivatives, and 2,2'-[propane-1,2-diylbis(azanylylidenemethanylylidene)]diphenol and its derivatives.

The heteroatom-containing ligand that forms the metal complex may be of one type alone or of two or more types that are different in structure.

In the metal complex, the ratio (molar ratio) of the metal ion or fatty acid metal salt to the heteroatom-containing ligand is, for example, in the range of 0.1 to 12 moles of the heteroatom-containing ligand per mole of metal atom of the metal ion or fatty acid metal salt, preferably in the range of 0.3 to 10 moles, and more preferably in the range of 0.5 to 10 moles.

When the metal ion in the metal complex is an aluminum ion, the aluminum complex is preferably one or more selected from the aluminum chelate compounds represented by the following general formula (3-1) and the aluminum chelate compounds represented by the following general formula (3-2).

（前記一般式（３－１）および（３－２）中、
Ｒ^３１１～Ｒ^３１６およびはＲ^３２１～Ｒ^３２６は、それぞれ独立に、炭素原子数１～２２のアルキル基又は炭素原子数１～２２のアルコキシ基である。）

(In the general formulas (3-1) and (3-2),
R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ are each independently an alkyl group having 1 to 22 carbon atoms or an alkoxy group having 1 to 22 carbon atoms.

The alkylene group moieties of the alkyl groups having 1 to 22 carbon atoms and the alkoxy groups having 1 to 22 carbon atoms of R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ may be linear or branched, or may contain an alicyclic structure. The number of carbon atoms in the alkyl group and the alkylene group moiety of the alkoxy groups of R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ is preferably 1 to 9.

The alkyl group having 1 to 22 carbon atoms for R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ is preferably a methyl group or an ethyl group.

The alkoxy group having 1 to 22 carbon atoms for R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ is preferably a methoxy group, an ethoxy group or an oleyloxy group.

Specific examples of aluminum chelate compounds include aluminum tris(acetylacetonate), aluminum tris(ethylacetoacetate), aluminum monoacetylacetonate bis(ethylacetoacetate), aluminum monoacetylacetonate bisoleylacetoacetate, ethylacetoacetate aluminum diisopropylate, and alkylacetoacetate aluminum diisopropylate.

The antibacterial and antiviral agent contained in the antibacterial and antiviral resin composition of the present invention is preferably a water-insoluble antibacterial and antiviral agent. The water-insoluble antibacterial and antiviral agent has excellent durability of antibacterial and antiviral properties even when exposed to water such as rain in daily life.
In the present application, "water-insoluble" means that the amount of water required to dissolve 1 g of the antibacterial and antiviral agent at 20°C is 10 ml or more.

The antibacterial and antiviral agents, ie, the metal complex of a heteroatom-containing ligand and a metal ion and the metal complex of a heteroatom-containing ligand and a fatty acid metal salt, can be produced by known methods, and can be produced by reacting a metal or a fatty acid metal salt with a heteroatom-containing ligand. In addition, the metal complex may be a commercially available product.

Among the above-mentioned antibacterial and antiviral agents, metal complexes are more preferred, and aluminum complexes or barium complexes are particularly preferred.

The antibacterial and antiviral agent of the present invention contained in the composition of the present invention may be one type alone or two or more types.

The composition of the present invention contains the metal derived from the antibacterial and antiviral agent in the range of 0.1 to 4 parts by mass, more preferably 0.5 to 4 parts by mass, and particularly preferably 1 to 4 parts by mass, per 100 parts by mass of the resin solids content. By containing the metal in these ranges, it is possible to improve the antibacterial, antiviral properties, and hardness of the cured coating film in a well-balanced manner.
The term "resin solid content" as used herein means the total amount of solid content such as polyfunctional (meth)acrylate compounds, monofunctional (meth)acrylate compounds, and monomers or oligomers such as binder resins contained in the composition.

[Polyfunctional (meth)acrylate compound]
Examples of the polyfunctional (meth)acrylate compound include aliphatic di(meth)acrylate compounds such as ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butanediol di(meth)acrylate, hexanediol di(meth)acrylate, and neopentyl glycol di(meth)acrylate; alicyclic di(meth)acrylate compounds such as 1,4-cyclohexanedimethanol di(meth)acrylate, norbornane di(meth)acrylate, norbornane dimethanol di(meth)acrylate, dicyclopentanyl di(meth)acrylate, and tricyclodecane dimethanol di(meth)acrylate; aromatic di(meth)acrylate compounds such as phenol di(meth)acrylate and bisphenol di(meth)acrylate; hydroxyl group-containing di(meth)acrylate compounds such as glycerol di(meth)acrylate and trimethylolpropane di(meth)acrylate; polyoxyalkylene-modified di(meth)acrylate compounds in which a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain or a polyoxytetramethylene chain has been introduced into the molecular structure of the above-mentioned various di(meth)acrylate compounds; lactone-modified di(meth)acrylate compounds in which a (poly)lactone structure has been introduced into the molecular structure of the above-mentioned various di(meth)acrylate compounds;

Aliphatic tri(meth)acrylate compounds such as trimethylolpropane tri(meth)acrylate and glycerin tri(meth)acrylate; hydroxyl-containing tri(meth)acrylate compounds such as pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate and dipentaerythritol tri(meth)acrylate; polyoxyalkylene-modified tri(meth)acrylate compounds in which a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain or a polyoxytetramethylene chain has been introduced into the molecular structure of the various tri(meth)acrylate compounds mentioned above; lactone-modified tri(meth)acrylate compounds in which a (poly)lactone structure has been introduced into the molecular structure of the various tri(meth)acrylate compounds mentioned above;

Aliphatic poly(meth)acrylate compounds having 4 or more functionalities, such as pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and dipentaerythritol hexa(meth)acrylate; hydroxyl-containing poly(meth)acrylate compounds having 4 or more functionalities, such as dipentaerythritol tetra(meth)acrylate and dipentaerythritol penta(meth)acrylate; polyoxyalkylene-modified poly(meth)acrylate compounds having 4 or more functionalities, in which a polyoxyalkylene chain, such as a polyoxyethylene chain, a polyoxypropylene chain, or a polyoxytetramethylene chain, has been introduced into the molecular structure of the various poly(meth)acrylate compounds; and lactone-modified poly(meth)acrylate compounds having 4 or more functionalities, in which a (poly)lactone structure has been introduced into the molecular structure of the various poly(meth)acrylate compounds.

The polyfunctional (meth)acrylate compound may be an epoxy (meth)acrylate compound or a urethane (meth)acrylate compound.

The epoxy (meth)acrylate compound is obtained by reacting an epoxy resin with (meth)acrylic acid or its anhydride. Examples of the epoxy resin include diglycidyl ethers of dihydric phenols such as hydroquinone and catechol; diglycidyl ethers of biphenol compounds such as 3,3'-biphenyldiol and 4,4'-biphenyldiol; bisphenol-type epoxy resins such as bisphenol A type epoxy resin, bisphenol B type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin; polyglycidyl ethers of naphthol compounds such as 1,4-naphthalenediol, 1,5-naphthalenediol, 1,6-naphthalenediol, 2,6-naphthalenediol, 2,7-naphthalenediol, binaphthol, and bis(2,7-dihydroxynaphthyl)methane; triglycidyl ethers of 4,4',4"-methylidynetrisphenol; novolac-type epoxy resins such as phenol novolac-type epoxy resin and cresol novolac resin;

Polyglycidyl ethers of polyether-modified aromatic polyols obtained by ring-opening polymerization of the biphenol compounds, bisphenol compounds, or naphthol compounds with cyclic ether compounds such as ethylene oxide, propylene oxide, tetrahydrofuran, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, and allyl glycidyl ether;

Examples include polyglycidyl ethers of lactone-modified aromatic polyols obtained by polycondensation of the biphenol compounds, bisphenol compounds, or naphthol compounds with lactone compounds such as ε-caprolactone.

These epoxy (meth)acrylate compounds can be used alone or in combination of two or more.

The urethane (meth)acrylate compound may be, for example, a compound obtained by reacting a polyisocyanate compound with a hydroxyl group-containing (meth)acrylate compound and, if necessary, a polyol compound. Examples of the polyisocyanate compound include diisocyanate compounds such as hexamethylene diisocyanate, isophorone diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and 4,4'-diphenylmethane diisocyanate, as well as their nurate modified products, adduct modified products, and biuret modified products. Examples of the hydroxyl group-containing (meth)acrylate compound include hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, trimethylolpropane diacrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and their polyoxyalkylene modified products and polylactone modified products. Examples of the polyol compound include ethylene glycol, propylene glycol, butanediol, hexanediol, polyoxyethylene glycol, polyoxypropylene glycol, glycerin, trimethylolpropane, pentaerythritol, biphenol, and bisphenol.

These polyfunctional (meth)acrylate compounds can be used alone or in combination of two or more. Among these, from the viewpoint of curability (reactivity, crosslink density, etc.), it is particularly preferable to use pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, acrylic (meth)acrylate, urethane (meth)acrylate, etc.

The content of the polyfunctional (meth)acrylate compound is preferably in the range of 10 to 100 parts by mass, more preferably in the range of 30 to 100 parts by mass, and particularly preferably in the range of 50 to 100 parts by mass, per 100 parts by mass of the resin solids. By setting the content in this range, the crosslink density after curing is improved, and the hardness of the cured coating film is improved.

The antibacterial and antiviral resin composition of the present invention may contain other additives other than the antibacterial and antiviral agent and the polyfunctional (meth)acrylate compound, as long as the effect of the present invention is not impaired.

[Other additives]
Examples of other additives include compound binder resins other than the polyfunctional (meth)acrylates, dispersion media, plasticizers, monofunctional (meth)acrylate compounds, photopolymerization initiators, photosensitizers, ultraviolet absorbers, antioxidants, silicone-based additives, fluorine-based additives, rheology control agents, defoamers, antistatic agents, antifogging agents, pigments, matting agents, curing agents, curing accelerators, defoamers, dispersants, leveling agents, thickeners, antioxidants, weather resistance agents, flame retardants, and lubricants.

The binder resin is not particularly limited, and any type of resin, such as emulsion-based resin, latex-based resin, thermosetting resin, or active energy ray-curable resin, can be used.

The binder resin may be either a water-based resin or a water-insoluble resin (solvent-based resin).
In this application, the term "water-soluble resin" means that the amount of water required to dissolve 1 g of the resin at 20° C. is less than 10 ml. The term "water-insoluble resin" refers to a resin other than the above-mentioned "water-soluble resin."

Specific examples of binder resins include acrylic resins, vinyl acetate resins, styrene resins, vinyl chloride resins, olefin resins, urethane resins, urea resins, urethane urea resins, epoxy resins, melamine resins, phenolic resins, polyester resins, alkyd resins, silicone resins, polyphenylene sulfide resins, acrylonitrile/styrene copolymer resins, acrylonitrile/butadiene copolymer resins, and acrylonitrile/butadiene/styrene copolymer (ABS) resins.
The binder resin includes modified versions of the above resins, and for example, in the case of a phenolic resin, it also includes a rosin-modified phenolic resin.

The binder resin contained in the composition of the present invention may be one type alone or two or more types.

The content of the binder resin in the composition of the present invention is not particularly limited, and may be set appropriately within the range of, for example, 10 to 100% by mass relative to the total mass of the resin solids in the composition.

The dispersion medium may be further added to adjust the viscosity of the composition of the present invention, and may be either an aqueous medium or an oil-based medium.

Specific examples of the dispersion medium include water, 1-butanol, isobutanol, 1-pentanol, 2-methyl-2-pentanol, 3-methyl-3-pentanol, methyl ethyl ketone, monofunctional alcohols such as methanol, ethanol, n-propyl alcohol, and isopropyl alcohol, various diols, polyhydric alcohols such as glycerin, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,9 -Diols such as nonanediol, 1,10-decanediol, 1,12-dodecanediol, propylene glycol, 1,2 butanediol, 3-methyl-1,3 butanediol, 1,2 pentanediol, 2-methyl-1,3 propanediol, 1,2 hexanediol, dipropylene glycol, and diethylene glycol; aromatic diols which are bisphenol A and alkylene oxide adducts having 2 or 3 carbon atoms (average molar addition number of 1 to 16) of bisphenol A; hydrogenated bisphenol A Alicyclic diols such as polyoxypropylene-2,2-bis(4-hydroxyphenyl)propane, polyoxyethylene-2,2-bis(4-hydroxyphenyl)propane, cyclohexanediol, ethylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monoisobutyl ether, propylene glycol monomethyl ether, propylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, ethyl carbitol, γ-butyrolactone, and various fatty acids.

The dispersion medium contained in the composition of the present invention may be one type alone or two or more types.

The content of the dispersion medium in the composition of the present invention is not particularly limited, and may be appropriately set so that the solids concentration of the composition is in the range of 30 to 80 mass %, for example.

A plasticizer may be further added to impart flexibility to the cured coating film obtained from the composition and improve its conformability to the substrate.

The plasticizer is not particularly limited, and examples thereof include phthalate esters, non-aromatic dibasic acid esters, aliphatic esters, esters of polyalkylene glycols, phosphate esters, trimellitic acid esters, chlorinated paraffin, hydrocarbon oils, process oils, polyethers, epoxy plasticizers, polyester plasticizers, and the like, with phthalate esters being preferred.
Specific examples of plasticizers include dibutyl phthalate, diheptyl phthalate, di(2-ethylhexyl) phthalate, dioctyl phthalate, dioctyl adipate, dioctyl sebacate, dibutyl sebacate, isodecyl succinate, tricresyl phosphate, tributyl phosphate, epoxidized soybean oil, and benzyl epoxy stearate.

The plasticizer contained in the composition of the present invention may be one type alone or two or more types.

The amount of plasticizer contained in the composition of the present invention is not particularly limited, and may be set appropriately within the range of, for example, 0.1 to 50 parts by mass per 100 parts by mass of the resin solid content of the composition.

Examples of the monofunctional (meth)acrylate compound include aliphatic mono(meth)acrylate compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and octyl (meth)acrylate; alicyclic mono(meth)acrylate compounds such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and adamantyl mono(meth)acrylate; heterocyclic mono(meth)acrylate compounds such as glycidyl (meth)acrylate and tetrahydrofurfuryl acrylate; benzyl (meth)acrylate, phenyl (meth)acrylate, phenoxy (meth)acrylate, 2-phenoxyethyl (meth)acrylate, and phenoxyethoxyethyl (meth)acrylate. acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 3-phenoxybenzyl (meth)acrylate, benzyl benzyl (meth)acrylate, o-phenylphenoxyethyl (meth)acrylate, and other aromatic mono(meth)acrylate compounds; hydroxyl group-containing mono(meth)acrylate compounds such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, and hydroxybutyl (meth)acrylate; polyoxyalkylene-modified mono(meth)acrylate compounds in which a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain, or a polyoxytetramethylene chain has been introduced into the molecular structure of the various mono(meth)acrylate compounds; lactone-modified mono(meth)acrylate compounds in which a structure derived from a (poly)lactone has been introduced into the molecular structure of the various mono(meth)acrylate compounds. These monofunctional (meth)acrylate compounds can be used alone or in combination of two or more.

When the monofunctional (meth)acrylate compound is added, the amount added is preferably in the range of 0 to 90% by mass, more preferably in the range of 0 to 50% by mass, of the resin solid content of the composition, from the viewpoint of hardness of the cured product and film-forming properties.

Examples of the photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethan-1-one, diphenyl(2,4,6-trimethoxybenzoyl)phosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone.

Examples of commercially available photopolymerization initiators include "Omnirad-1173", "Omnirad-184", "Omnirad-127", "Omnirad-2959", "Omnirad-369", "Omnirad-379", "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", "Omnirad-754", "Omnirad-784", "Omnirad-500", and "Omnirad-8". Examples of photopolymerization initiators include "Kayacure-DETX", "Kayacure-MBP", "Kayacure-DMBI", "Kayacure-EPA", "Kayacure-OA" (manufactured by Nippon Kayaku Co., Ltd.), "Baicure-10", "Baicure-55" (manufactured by Stouffer Chemical Co., Ltd.), "Trigonal P1" (manufactured by Akzo Co., Ltd.), "Sandray 1000" (manufactured by Sandoz Co., Ltd.), "Deep" (manufactured by Upjohn Co., Ltd.), "Quantacure-PDO", "Quantacure-ITX", "Quantacure-EPD" (manufactured by Ward Blenkinsop Co., Ltd.), "Runtecure-1104", "Runtecure-1108" (manufactured by Runtec Co., Ltd.), and the like. These photopolymerization initiators can be used alone or in combination of two or more types.

When the photopolymerization initiator is added, the amount added is, for example, preferably in the range of 0.05 to 20% by mass, more preferably in the range of 0.1 to 10% by mass, based on the solid content of the composition.

Examples of the photosensitizer include amine compounds such as aliphatic amines and aromatic amines, urea compounds such as o-tolylthiourea, and sulfur compounds such as sodium diethyldithiophosphate and s-benzylisothiuronium-p-toluenesulfonate. These photosensitizers can be used alone or in combination of two or more.

When the photosensitizer is added, the amount added is preferably in the range of 0.01 to 10% by mass in the composition.

<<Cured Coating Film>>
The cured coating film of the present invention can be obtained by irradiating the composition of the present invention with active energy rays. Examples of the active energy rays include ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. When ultraviolet rays are used as the active energy rays, irradiation may be performed under an inert gas atmosphere such as nitrogen gas, or under an air atmosphere in order to efficiently carry out the curing reaction by ultraviolet rays.

As a source of ultraviolet light, ultraviolet lamps are generally used from the standpoint of practicality and economy. Specific examples include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, gallium lamps, metal halide lamps, sunlight, LEDs, etc.

The cumulative light amount of the active energy rays is not particularly limited, but is preferably 0.1 to 50 kJ/m ² , and more preferably 0.3 to 20 kJ/m ^2. When the cumulative light amount is within the above range, it is preferable because the occurrence of uncured portions can be prevented or suppressed.

The irradiation of the active energy rays may be carried out in one step or in two or more steps.

<<Laminate>>
The laminate of the present invention has the cured coating film on at least one surface of a substrate, i.e., on one or both surfaces, and can be obtained, for example, by applying a composition to any substrate and curing it by irradiating it with active energy rays. In this case, the cured coating film may be transparent.

The substrate is not particularly limited and may be appropriately selected depending on the application. Examples of the substrate include glass, wood, metal, metal oxide, paper, synthetic paper, silicone or modified silicone, steel plate, aluminum foil, woven fabric, knitted fabric, nonwoven fabric, gypsum board, wooden board, and resin substrates. The substrate may be obtained by bonding different materials.
The shape of the substrate is not particularly limited, and may be any shape according to the purpose, such as a flat plate, a sheet, or a three-dimensional shape having a curvature on the entire surface or part thereof, etc. Furthermore, there is no limitation on the hardness, thickness, etc. of the substrate.

Specific examples of the resin substrate include polyethylene terephthalate (PET) film, polystyrene film, polyamide film, polyacrylonitrile film, polyethylene film (LLDPE: low density polyethylene film, HDPE: high density polyethylene film), polypropylene film (CPP: unstretched polypropylene film, OPP: biaxially stretched polypropylene film), polyvinyl alcohol film, ethylene-vinyl alcohol copolymer film, polycarbonate film, polyethylene terephthalate film, polymethyl methacrylate film, polystyrene film, polyester film, polyolefin film, epoxy resin film, melamine resin film, triacetyl cellulose resin film, polyvinyl alcohol film, ABS resin film, norbornene-based resin film, cyclic olefin-based resin film, polyimide resin film, polyvinyl fluoride resin film, polyvinylidene fluoride resin film, ethylene-vinyl acetate copolymer film, and the like.
The resin substrate used may be subjected to a surface treatment such as a corona treatment.

The substrate may also contain known additives such as known antistatic agents, antifogging agents, antiblocking agents, UV absorbers, antioxidants, pigments, organic fillers, inorganic fillers, light stabilizers, crystal nucleating agents, and lubricants, to the extent that the effects of the present invention are not impaired.

Methods for forming the cured coating film include, for example, a coating method, a transfer method, a sheet adhesion method, etc.

The coating method is a method in which the paint is spray-coated or applied as a top coat to a molded product using printing equipment such as a curtain coater, roll coater, or gravure coater, and then cured by irradiating it with active energy rays.

The transfer method is a method in which a transfer material obtained by applying the active energy ray curable composition described above onto a base sheet having releasability is adhered to the surface of a molded product, the base sheet is peeled off, a top coat is transferred to the surface of the molded product, and then the top coat is irradiated with active energy rays to harden it, or a method in which the transfer material is adhered to the surface of a molded product, the top coat is irradiated with active energy rays to harden it, and then the base sheet is peeled off to transfer the top coat to the surface of the molded product.

The sheet adhesion method is a method of forming a protective layer on the surface of a plastic molded product by adhering a protective sheet having a coating film made of the curable composition on a base sheet, or a protective sheet having a coating film made of the curable composition and a decorative layer on a base sheet, to the molded product.

Specific examples of the sheet adhesion method include a method in which a base sheet of a protective layer-forming sheet prepared in advance is adhered to a molded product, and then the resin layer is crosslinked and cured by heating to heat and set to the B-stage (post-adhesion method), and a method in which the protective layer-forming sheet is sandwiched within a molding die, resin is injected into the cavity to fill it, and the surface of the resin molded product is simultaneously adhered to the protective layer-forming sheet, and then the resin layer is crosslinked and cured by heating to heat and set (simultaneous molding adhesion method).

In either formation method, if the composition of the present invention contains an organic solvent, it is preferable to heat the composition after application at 40 to 120°C for several tens of seconds to several minutes to volatilize the organic solvent, and then irradiate the composition with active energy rays to cure the composition.

The laminate of the present invention may have other layer configurations in addition to the cured coating film made of the composition and the substrate. The method of forming these various layer configurations is not particularly limited, and for example, they may be formed by directly applying a resin raw material, or pre-formed sheets may be bonded together with an adhesive.

<<Molded body>>
The molded article of the present invention is obtained by molding the composition of the present invention, and can be a molded article exhibiting antibacterial and antiviral properties.

The composition of the present invention can be molded by any molding method suitable for the resin used, including melt molding methods such as injection molding, extrusion molding, pressure molding (press molding), compressed air molding, and vacuum molding, as well as casting methods.

The cured coating films, laminates, and molded articles obtained using the composition of the present invention are suitable for use as materials with antibacterial and antiviral activity in locations that are touched by human hands. Applications include a wide range of uses, such as the exterior of smartphones, the exterior of personal computers, touch panels, handrails, doorknobs, washstands, push buttons such as elevator buttons, interior furnishings (wallpaper, flooring, etc.), various packaging materials, various textile products, and medical equipment (medical gloves, medical glasses, etc.).

The present invention will be specifically described below with reference to examples and comparative examples.
However, the present invention is not limited to the following examples.

(Synthesis Example 1: Preparation of antibacterial and antiviral agent (1))
To a 2-liter flask equipped with a stirrer, a condenser, and a thermometer, 552.0 parts by mass of aluminum isopropylate and 294.4 parts by mass of xylene were added and stirred for a fixed period of time, and then 368.0 parts by mass of ethyl acetoacetate was added and stirred at 60° C. for 2 hours to obtain 1,214.4 parts by mass of a xylene/2-propanol solution of an aluminum chelate compound (a compound in general formula (3-1) where R ³¹¹ to R ³¹⁶ are ethyl) (antibacterial and antiviral agent (1)). The aluminum content in the obtained antibacterial and antiviral agent (1) was 6% by mass.

(Synthesis Example 2: Preparation of antibacterial and antiviral agent (2))
Into a 2-L flask equipped with a stirrer, a condenser, and a thermometer, 540.0 parts by mass of 2-ethylhexanoic acid and 400.0 parts by mass of barium hydroxide octahydrate were successively added, and after stirring for a fixed period of time under conditions of 110°C, 401.2 parts by mass of a petroleum-based hydrocarbon was added. Dehydration was carried out under reduced pressure at 90°C. 34.0 parts by mass of butyl diglycol was added to obtain 1142.0 parts by mass of a petroleum-based hydrocarbon solution of barium 2-ethylhexanoate (antibacterial and antiviral agent (2)). The barium content in the obtained antibacterial and antiviral agent (2) was 15% by mass.

(Example 1: Preparation of antibacterial and antiviral resin composition (1))
0.7 parts by mass of the antibacterial and antiviral agent (1) obtained in Synthesis Example 1, 43 parts by mass of pentaerythritol tri- and tetraacrylate ("Aronix M-305" manufactured by Toagosei Co., Ltd.), 2 parts by mass of 1-hydroxycyclohexyl phenyl ketone ("Irgacure 184" manufactured by IGM) as a photoinitiator, and 54.3 parts by mass of propylene glycol monomethyl ether were mixed and homogenized to obtain an antibacterial and antiviral resin composition (1).

(Example 2-5: Preparation of antibacterial and antiviral resin compositions (2) to (5))
Compositions (2) to (5) were prepared in the same manner as in Example 1, except that the compositions and blending ratios were changed as shown in Table 1.

(Comparative Examples 1-4: Preparation of antibacterial and antiviral resin compositions (C1) to (C4))
Compositions (C1) to (C4) were prepared in the same manner as in Example 1, except that the composition and blending ratio were changed to those shown in Table 1. In Comparative Example 1, the resin composition (C1) was prepared without adding an antibacterial and antiviral agent.

The following measurements and evaluations were carried out using the active energy ray-curable compositions obtained in the above examples and comparative examples.

(Appearance evaluation of coating material)
The state of the antibacterial and antiviral resin compositions obtained in each of the Examples and Comparative Examples was visually observed. The evaluation criteria were as follows.
〇: No cloudiness or sedimentation ×: Cloudiness or separation

(Viscosity Measurement)
The viscosity (mPa·s) at 25° C. of the active energy ray-curable composition obtained in each of the Examples and Comparative Examples was measured using an E-type viscometer (TV-25, manufactured by Toki Sangyo Co., Ltd.).

(Preparation of evaluation samples)
Each composition obtained in the examples and comparative examples was applied to a PET substrate with an applicator to a film thickness of 8 μm, and then cured by irradiating ultraviolet rays with an ultraviolet irradiator at an integrated dose of 150 mJ/ ^cm2 under a nitrogen atmosphere. These were used as evaluation samples.

(Coating film appearance evaluation)
The state of the evaluation sample obtained above was visually observed and the evaluation criteria were as follows.
〇: No whitening ×: Whitening or discoloration

(Transparency test)
Using the above evaluation samples, the transmittance at a wavelength of 380 nm was measured using a spectrophotometer U-2800 (manufactured by Hitachi High-Tech Science Corporation).

(Haze test)
Using the above evaluation sample, the haze value was measured at 25° C. and a thickness of 50 μm under a D65 light source in accordance with JIS K7136.

(Pencil hardness test)
The pencil hardness of the above evaluation sample was measured under a load of 750 g in accordance with JIS K5600-5-4 (1999). Five measurements were made for each hardness, and the hardness at which no scratches were observed four or more times was regarded as the surface hardness of the laminate film.
The hardness of the pencils is 2H, H, F, HB, and B, in order of decreasing hardness.

(Antiviral Test)
The antiviral evaluation was performed using bacteriophage Qβ as a target, with reference to the antiviral performance evaluation test using bacteriophage in JIS R 1756: 2020. Note that an evaluation sample prepared using the resin composition (C1) not containing the antibacterial and antiviral agent (1) of Comparative Example 1 was used as a blank test piece.
The conditions for virus inoculation onto the blank test piece surface and the surfaces of each evaluation sample were 4 hours at 25° C. in a dark place. From the bacteriophage Qβ infectivity titers after 4 hours of reaction in the blank test piece and the evaluation samples, the antiviral activity value was calculated using the following formula. The results are shown in Table 1. An antiviral activity value of 2.0 or more was evaluated as having an antiviral effect.
V = Log(A/B) = Log(A) - Log(B)
V: Antiviral activity value Log(A): Common logarithm of the infectivity value of a blank test piece after 4 hours of reaction J
Log(B): Common logarithm of the infectivity of the evaluation sample after 4-hour reaction J

The compositions and evaluation results of the active energy curable compositions (1) to (6) and (C1) to (C2) prepared in Examples 1 to 6 and Comparative Examples 1 and 2 are shown in Tables 1 and 2.

The abbreviations in Table 1 are as follows:
M305: Pentaerythritol tri- and tetraacrylate (manufactured by Toagosei Co., Ltd., product name "Aronix M-305"
V6840: Acrylic acrylate (manufactured by DIC Corporation, product name "Luxidia V6840")
Antibacterial and antiviral agent (1): A xylene/2-propanol solution of the aluminum chelate compound obtained in Synthesis Example 1 (a compound in which R ³¹¹ , R ³¹³ , and R ³¹⁵ in the general formula (3-1) are methyl groups, and R ³¹² , R ³¹⁴ , and R ³¹⁶ are ethoxy groups). Antibacterial and antiviral agent (2): A petroleum hydrocarbon solution of barium 2-ethylhexanoate obtained in Synthesis Example 2.

In Table 1, the compositions of Examples 1 to 5, in which the metal content is in the range of 0.1 to 4 parts by mass per 100 parts by mass of the resin solids, were able to form cured coating films with high hardness and excellent antiviral properties. On the other hand, Comparative Example 1, which does not contain a metal complex, showed reduced antiviral properties. The compositions of Comparative Examples 2 to 4, in which the metal content is 5 parts by mass or more per 100 parts by mass, showed a significant reduction in hardness.

Claims (7)

An antibacterial and antiviral resin composition containing an antibacterial and antiviral agent and a polyfunctional (meth)acrylate compound,
the antibacterial and antiviral agent is at least one selected from the group consisting of a fatty acid metal salt, a metal complex of a heteroatom-containing ligand and a metal ion, and a metal complex of a heteroatom-containing ligand and a fatty acid metal salt;
An antibacterial and antiviral resin composition comprising the metal derived from the antibacterial and antiviral agent in an amount of 0.1 to 4 parts by mass per 100 parts by mass of resin solids. The antibacterial and antiviral resin composition according to claim 1, wherein the antibacterial and antiviral agent is an aluminum complex or a barium complex. The antibacterial and antiviral resin composition according to claim 2, wherein the aluminum complex is a compound represented by the following general formula (3-1) or (3-2):

(In the general formulas (3-1) and (3-2),
R ³¹¹ to R ³¹⁶ and R ³²¹ to R ³²⁶ are each independently an alkyl group having 1 to 22 carbon atoms or an alkoxy group having 1 to 22 carbon atoms. The antibacterial and antiviral resin composition according to claim 1, wherein the polyfunctional (meth)acrylate compound is at least one selected from pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, acrylic (meth)acrylate, and urethane (meth)acrylate. A cured coating film comprising a cured product of the antibacterial and antiviral resin composition according to claims 1 to 4. The laminate according to claim 5, wherein the cured coating film is transparent. A molded article made from the antibacterial and antiviral resin composition according to claim 1.