Curable composition, cured body, optical article, lens, rubber sheet, eye protector, antibacterial / antiviral agent, and resin composition

Abstract

Provided is a curable composition comprising a first bismuth compound having bismuth and at least one of an acryloyl group and a methacryloyl group, and a first radical polymerizable monomer which has a polyethylene glycol chain and in which the ratio N2 / N1 of the number average molecular weight N2 of the polyethylene glycol chain to the number average molecular weight N1 is 75-95%, wherein the percentage of the polyethylene glycol chain is 13.5 mass% or more in the composition. Also provided are: a cured body of the curable composition; and an optical article, a lens, a rubber sheet, an eye protector, and an antibacterial / antiviral agent each containing the cured body.

Description

Curable compositions, cured products, optical articles, lenses, rubber sheets, eye protection equipment, antibacterial and antiviral agents, and resin compositions

[0001] The present disclosure relates to a curable composition, a cured product, an optical article, a lens, a rubber sheet, eye protection equipment, an antibacterial / antiviral agent, and a resin composition.

[0002] Lead glass and acrylic lead are used as radiation protection materials to protect the eyes from radiation. However, lead is harmful to the environment and the human body, and lead-free alternatives are strongly desired. As such alternatives, research and development has been conducted on curable compositions containing bismuth compounds in which a phosphate ester having a (meth)acryloyl group is bonded to bismuth.

[0003] International Publication No. 2022 / 014591 International Publication No. 2019 / 177084

[0004] An object of the present disclosure is to provide a curable composition capable of providing a resin composition having antifogging properties, a cured product, an optical article, a lens, a rubber sheet, eye protection equipment, and an antibacterial and antiviral agent.

[0005] According to the present disclosure, there is provided a curable composition. The curable composition contains a first bismuth compound and a first radically polymerizable monomer. The first bismuth compound has bismuth and at least one of an acryloyl group and a methacryloyl group. The first radically polymerizable monomer has a polyethylene glycol chain. In the first radically polymerizable monomer, the proportion N2 / N1 of the number average molecular weight N1 of the polyethylene glycol chain is 75% or more and 95% or less. In the curable composition, the proportion of the polyethylene glycol chain is 13.5% by mass or more.

[0006] According to the present disclosure, a cured product is provided. The cured product is a cured product of the curable composition of the present disclosure.

[0007] According to the present disclosure, an optical article is provided. The optical article includes the cured body of the present disclosure.

[0008] According to the present disclosure, a lens is provided, the lens comprising the cured body of the present disclosure.

[0009] According to the present disclosure, there is provided a rubber sheet, which includes the cured body of the present disclosure.

[0010] According to the present disclosure, an eye protection device is provided, which includes the cured body of the present disclosure.

[0011] According to the present disclosure, there is provided an antibacterial / antiviral agent, which includes the cured product of the present disclosure.

[0012] According to the present disclosure, there is provided a resin composition comprising bismuth, a (meth)acrylic resin, and 16.0 mass % or more of polyethylene glycol chains.

[0013] According to the present disclosure, there are provided a curable composition capable of providing a resin composition having antifogging properties, a cured product, an optical article, a lens, a rubber sheet, eye protection equipment, and an antibacterial and antiviral agent.

[0014] Radiation protective materials for eye protection are required to have optical properties such as high transparency and surface smoothness in addition to radiation protection ability. For example, molded products made of radiation protective materials for eye protection, such as eyeglasses and goggles, are sometimes used in the vicinity of the human eyeballs, and therefore the lenses can become fogged by human breath, etc., resulting in a decrease in transparency. Therefore, there is a demand for radiation protective materials with anti-fogging properties.

[0015] According to the present disclosure, there is provided a curable composition. The curable composition contains a first bismuth compound and a first radically polymerizable monomer. The first bismuth compound has bismuth and at least one of an acryloyl group and a methacryloyl group. The first radically polymerizable monomer has a polyethylene glycol chain. In the first radically polymerizable monomer, the proportion N2 / N1 of the number average molecular weight N1 of the polyethylene glycol chain is 75% or more and 95% or less. In the curable composition, the proportion of the polyethylene glycol chain is 13.5% by mass or more.

[0016] The curable composition of the present disclosure can provide a resin composition having antifogging properties. That is, the curable composition includes a first radical polymerizable monomer in which polyethylene glycol chains account for a majority of the molecular weight, and also includes a certain amount or more of polyethylene glycol chains. In a cured product of such a curable composition, the hydrophilic polyethylene glycol chains have a relatively high free energy, which is thought to result in the formation of a hydrophilic interface on the surface of the cured product.

[0017] Each component used in the curable composition of the present disclosure will be described below. Each component described below may be used alone or in combination of two or more. In this specification, the term "(meth)acryloyl" means both "acryloyl" and "methacryloyl". The same applies to terms such as "(meth)acrylate" and "(meth)acrylic resin".

[0018] <First Bismuth Compound> The first bismuth compound has bismuth and at least one of an acryloyl group and a methacryloyl group. Since the first bismuth compound contains bismuth, it can be used as a radiation-shielding material. Radiation includes electromagnetic radiation and particle radiation. Electromagnetic radiation includes X-rays and gamma rays. Particle radiation includes alpha rays, beta rays, neutron rays, and proton rays. The first bismuth compound has excellent X-ray shielding ability, and is therefore particularly suitable for use as an X-ray shielding material and a beta-ray shielding material that can generate X-rays.

[0019] The bismuth (I) compound has high solubility in radically polymerizable compounds having at least one radically polymerizable group selected from the group consisting of a nitrile group, an acryloyl group, a methacryloyl group, a vinyl group, and an allyl group. Therefore, the use of the bismuth (I) compound makes it possible to obtain a curable composition containing a high concentration of bismuth and a cured product thereof. The bismuth (I) compound has better solubility in radically polymerizable compounds than bismuth subsalicylate alone.

[0020] The first bismuth compound may be in any form as long as it contains bismuth and a (meth)acryloyl group. For example, the bismuth and the (meth)acryloyl group may be bonded directly or via a bonding group. Examples of the bonding group include an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphate group.

[0021] The first bismuth compound preferably further has a phosphate bond. Furthermore, the first bismuth compound is more preferably a compound in which bismuth is bonded to a first phosphate ester having a (meth)acryloyl group. Such a first bismuth compound tends to have higher compatibility with various polymerizable compounds. The bond between bismuth and the first phosphate ester is not particularly limited, and may be any of an ionic bond, a coordinate bond, or a covalent bond. That is, the first bismuth compound is a compound in which bismuth (Bi ３＋ or Bi ５＋ ) as the cation and the primary phosphate ester as the anion, or may be a phosphate compound or a complex.

[0022] The first bismuth compound may be a mono(meth)acrylate having one (meth)acryloyl group, a di(meth)acrylate having two (meth)acryloyl groups, a tri(meth)acrylate having three (meth)acryloyl groups, or a polyfunctional (meth)acrylate having four or more (meth)acryloyl groups.

[0023] In the first bismuth compound, the first phosphate ester is represented, for example, by the following formula (2).

[0024]

[0025] In the above formula (2), Q １ is a hydrogen atom or a methyl group. １ is preferably a methyl group.

[0026] Q ２is a hydrogen atom, a linear or branched alkyl group having from 1 to 10 carbon atoms, an aryl group having from 4 to 16 carbon atoms, or a (meth)acryloyloxyalkyl group. The number of carbon atoms in the alkyl group is preferably from 1 to 6. The number of carbon atoms in the aryl group is preferably from 5 to 8. The aryl group is preferably a phenyl group. The number of carbon atoms in the alkyl moiety contained in the (meth)acryloyloxyalkyl group is, for example, from 1 to 10, preferably from 1 to 3. The (meth)acryloyloxyalkyl group is preferably a (meth)acryloyloxyethyl group.

[0027] a ３ is 0 or 1. ３ When is 0, Q ２ The oxygen atom to which is bonded is O － is.

[0028] Q ３ is a linear or branched alkylene group having 1 to 10 carbon atoms, or a linear or branched alkyleneoxyalkylene group having 2 to 10 carbon atoms.

[0029] The first bismuth compound may further have other compounds bonded thereto in addition to the first phosphate ester. The bond between the other compounds and the bismuth may be any of an ionic bond, a coordinate bond, and a covalent bond. That is, the first bismuth compound may have bismuth (Bi ３＋ or Bi ５＋ ) as a cation and a primary phosphate ester or other compound as an anion, or may be a phosphate compound or a complex.

[0030] Specific examples of the other compounds include at least one selected from the group consisting of salicylic acid and (meth)acrylic acid.

[0031] To improve the solubility in radically polymerizable compounds, the ratio of the primary phosphate ester to the other compound is preferably 0.1 to 10 moles, more preferably 0.1 to 5 moles, even more preferably 0.1 to 1 mole, and particularly preferably 0.1 to 0.5 moles, of the other compound per mole of the primary phosphate ester. When two or more types of primary phosphate esters are present, the above range is based on the total number of moles of the primary phosphate esters.

[0032] The fact that the primary phosphate ester is bonded to bismuth can be confirmed by infrared spectroscopy (IR). That is, in infrared spectroscopy measurement of the primary bismuth compound, for example, －１ When a peak is observed at 1000 kJ / cm, it can be said that the primary phosphate ester is bonded to the bismuth. This peak is considered to be a peak characteristic of the stretching vibration of Bi-O-P. This peak is not observed in the bismuth and primary phosphate ester before bonding. Furthermore, this peak is not observed in the mixture of the secondary bismuth compound and the primary phosphate ester, which are the raw materials for the primary bismuth compound, which will be described later.

[0033] The IR spectrum is measured, for example, using Spectrum One manufactured by PerkinElmer, by the ATR method with single reflection and four-times integration.

[0034] Furthermore, by combining elemental analysis such as NMR (nuclear magnetic resonance spectroscopy), MALDI-TOF-MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry), XPS (X-ray photoelectron spectroscopy), and EDS (energy dispersive X-ray spectrometry), the number of bonds of salicylic acid or (meth)acrylic acid and each phosphate ester in the bismuth (I) compound can be confirmed.

[0035] １ H-, ３１ For the P-NMR measurement, a nuclear magnetic resonance apparatus (JNM-ECA400II manufactured by JEOL Ltd.) is used, deuterated acetone is used as the solvent, and the sample concentration is 1% by mass.

[0036] ​XPS measurements are performed using an X-ray photoelectron spectrometer (ESCA5701ci / MC, manufactured by ULVAC-PHI, Inc.) with a monochromated Al-Kα (14 kV-330 W) X-ray source, an aperture diameter of φ800 μm, and a photoelectron take-off angle of 45 degrees. The sample is pulverized in an agate mortar, and the resulting powder is fixed to a substrate with carbon tape and introduced into the measurement chamber for measurement.

[0037] The first bismuth compound preferably further contains a phenyl group. A first bismuth compound containing a phenyl group tends to have high compatibility with radical polymerizable monomers. The presence of a phenyl group in the first bismuth compound can be confirmed, for example, by Fourier transform infrared spectroscopy (FT-IR).

[0038] The first bismuth compound is, for example, a phosphate or complex salt represented by the following formula (1).

[0039]

[0040] In the above formula (1), Q １ , Q ２ , Q ３ , and a ３ is the same as the above formula (2).

[0041] In the above formula (1), X is (meth)acrylic acid represented by the following formula (1a) or salicylic acid represented by the following formula (1b). In formula (1a), R is a hydrogen atom or a methyl group. X is preferably salicylic acid represented by formula (1b).

[0042]

[0043]

[0044] a １ is a number between 0 and 1. ２ is a number between 0.1 and 3. １ +a ２ is a number between 2 and 3 inclusive.

[0045] The fact that the first bismuth compound has the structure represented by the above formula (1) can be confirmed, for example, by detecting a proton-adduct molecular ion or a sodium-adduct ion of the compound in MALDI-TOF-MS measurement. １ is a number of 0 to 1, X is salicylic acid, a ２ is a number between 1 and 3, Q １ is a methyl group, Q ２ is a methacryloyloxyalkyl group, Q ３ When a compound in which is a linear alkylene group having two carbon atoms is measured, a protonated ion with m / z=667 is detected.

[0046] For MALDI-TOF-MS measurements, a Bruker Rapiflex TOF / TOF model was used, CHCA (α-cyano-4-hydroxycinnamic acid), DIT (Dithranol), and DHB (2,5-Dihydroxybenzoic acid) were used as matrices, and sodium trifluoroacetate was used as a cationizing agent. Measurements were performed in reflector / positive mode, with a mass range of m / z = 20 to 4000.

[0047] The first bismuth compound may be a mixture of multiple types of first phosphate esters and multiple types of other compounds bound to bismuth. The first bismuth compound is preferably a mixture of both a first phosphate ester having one (meth)acryloyl group and a first phosphate ester having two (meth)acryloyl groups bound to bismuth. Such a first bismuth compound tends to be highly compatible with polymerizable compounds.

[0048] In such a first bismuth compound, the ratio of the first phosphate ester having two (meth)acryloyl groups to 1 mole of the first phosphate ester having one (meth)acryloyl group is preferably 0.05 to 3 moles, more preferably 0.10 to 2 moles, and even more preferably 0.15 to 1 mole.

[0049] Suitable bismuth compounds include those represented by the following formulas (III) to (V).

[0050]

[0051]

[0052]

[0053] In the formula, each R is independently a hydrogen atom or a methyl group.

[0054] In the above formula (III), a + x + y + z = 3. x represents the number of moles of 2-((meth)acryloyloxy)ethyl hydrogen phosphate residues. y represents the number of moles of phenyl-2-((meth)acryloyloxy)ethyl phosphate residues. z represents the number of moles of bis[2-((meth)acryloxyoxy)ethyl]phosphate residues. a represents the number of moles of (meth)acrylic acid residues.

[0055] In the above formula (IV), 2b + u + v + w = ​​3. u represents the number of moles of 2-((meth)acryloyloxy)ethyl hydrogen phosphate residues. v represents the number of moles of phenyl-2-((meth)acryloyloxy)ethyl phosphate residues. w represents the number of moles of bis[2-((meth)acryloyloxy)ethyl]phosphate residues. b represents the number of moles of salicylic acid residues.

[0056] In the above formula (V), 2c + q + r + 2s + t = 3. q represents the number of moles of 2-((meth)acryloyloxy)ethyl hydrogen phosphate residues. r represents the number of moles of phenyl-2-((meth)acryloyloxy)ethyl phosphate residues. s represents the number of moles of 2-((meth)acryloyloxy)ethyl phosphate residues. t represents the number of moles of bis[2-((meth)acryloyloxy)ethyl]phosphate residues. c represents the number of moles of salicylic acid residues.

[0057] The first bismuth compounds represented by the formulas (III) to (V) may be mixtures of multiple compounds rather than a single compound. In such cases, the number of moles of each residue refers to the number of moles of the entire mixture.

[0058] In the above formula (III), in consideration of obtaining a first bismuth compound that can be produced at low temperatures and has little coloration, when a = 0, x:y:z = 1:0.05-3:0.5-30 is preferable, x:y:z = 1:0.1-2:1-20 is more preferable, and x:y:z = 1:0.15-1:1.5-10 is even more preferable. In order to further reduce coloration, a = 0 and y = 0 may also be satisfied.

[0059] In addition, in the above formula (III), when a is other than 0, it is preferable that a:(x+y+z)=0.1 to 10:1, more preferably a:(x+y+z)=0.1 to 5:1, and even more preferably a:(x+y+z)=0.1 to 1:1. In this case, it is preferable that x:y:z=1:0.05 to 3:0.5 to 30, more preferably x:y:z=1:0.1 to 2:1 to 20, and even more preferably x:y:z=1:0.15 to 1:1.5 to 10.

[0060] In the above formula (IV), when b=0, it is the same as when x is replaced by u, y by v, and z by w in the above definition.

[0061] In addition, in the above formula (IV), when b is other than 0, it is preferable that b:(u+v+w)=1:0.1-30, more preferably b:(u+v+w)=1:0.2-20, even more preferably b:(u+v+w)=1:0.3-10, and particularly preferably b:(u+v+w)=1:0.5-5. In this case, it is preferable that u:v:w=1:0.05-20:0.1-40, more preferably u:v:w=1:0.1-10:0.2-20, and even more preferably u:v:w=1:0.2-5:0.4-10.

[0062] In the above formula (V), when c = 0, the relationship q:r:s:t is preferably 1:0.1-50:0.05-20:0.1-40, more preferably 1:0.3-30:0.1-10:0.2-20, and even more preferably 1:0.5-20:0.2-5:0.4-10.

[0063] In addition, in the above formula (V), when c is other than 0, it is preferable that c:(q+r+s+t)=1:0.1 to 30, more preferably c:(q+r+s+t)=1:0.2 to 20, even more preferably c:(q+r+s+t)=1:0.3 to 10, and particularly preferably c:(q+r+s+t)=1:0.5 to 5. In this case, it is preferable that q:r:s:t=1:0.1 to 50:0.05 to 20:0.1 to 40, more preferably q:r:s:t=1:0.3 to 30:0.1 to 10:0.2 to 20, and even more preferably q:r:s:t=1:0.5 to 20:0.2 to 5:0.4 to 10.

[0064] The first bismuth compound is, for example, a phosphate or complex salt represented by the following formula (3).

[0065]

[0066] In the above formula (3), Q １ , Q ２ , Q ３ , and a ３ is the same as the above formula (2).

[0067] a ４ is a number greater than 0 and less than or equal to 3. ５ is a number greater than 0 and less than or equal to 3. ４ +a ５ is 3.

[0068] The first bismuth compound preferably contains at least one compound selected from the group consisting of a compound represented by the following formula (3a), a compound represented by the following formula (3b), a compound represented by the following formula (3c), and a compound represented by the following formula (3d). The first bismuth compound more preferably contains a compound represented by the following formula (3a).

[0069]

[0070]

[0071]

[0072]

[0073] The proportion of bismuth in the first bismuth compound is, for example, 40% by mass or more and 60% by mass or less, and preferably 45% by mass or more and 50% by mass or less. This proportion can be confirmed by ICP spectrochemical emission analysis.

[0074] The first bismuth compound may also be a composition containing a compound other than the first bismuth compound. Hereinafter, this composition will also be referred to as the first bismuth composition. The first bismuth composition may contain a phosphate compound by-produced during production or unreacted raw materials.

[0075] Although removing these by-produced phosphate compounds or unreacted raw materials from the bismuth(II) compound requires a great deal of industrial effort, these by-produced phosphate compounds or unreacted raw materials may contribute to improving the solubility of the bismuth(II) compound in the radical polymerizable monomer.

[0076] Examples of by-produced phosphoric acid compounds include a dimer of a phosphoric acid ester having one (meth)acryloyl group (phosphoric acid monoester), a dimer of a phosphoric acid ester having two (meth)acryloyl groups (phosphoric acid diester), and an ester of bismuth salicylate or bismuth (meth)acrylate with phosphoric acid.

[0077] Examples of unreacted raw materials include phosphate esters having one (meth)acryloyl group (phosphate monoesters), phosphate esters having two (meth)acryloyl groups (phosphate diesters), bismuth salicylate, and bismuth (meth)acrylate.

[0078] In the first bismuth composition, the proportion of compounds other than the first bismuth compound is, for example, 30 mass % or less. There is no lower limit to this proportion, but in one example it is 0 mass %, and in another example it is 5 mass %. This proportion is １ This can be confirmed by quantifying the by-product phosphate compound and unreacted raw materials in the bismuth(II) composition by an internal standard method using H NMR.

[0079] The first bismuth composition may also contain a bismuth oxide-derived compound. The bismuth oxide-derived compound is, for example, a compound in which bismuth oxide is bonded to a phosphate ester having a (meth)acryloyl group, (meth)acrylic acid, and / or salicylic acid. Although the structure of this bismuth oxide-derived compound is unclear, it is believed that a hydroxy group formed on the surface of the bismuth oxide is bonded to a carboxy group of the phosphate ester, (meth)acrylic acid, or salicylic acid. Separating this bismuth oxide-derived compound from the first bismuth compound is extremely difficult. Therefore, when a bismuth oxide-derived compound is by-produced, it is preferable to use the composition in a state in which the bismuth oxide-derived compound is included. When a bismuth oxide-derived compound is by-produced, it is desirable to adjust the production conditions, etc., so that its amount does not reduce the solubility of the first bismuth composition. The presence of a bismuth oxide-derived compound can be comprehensively determined by the production conditions or methods such as IR, NMR, and XPS.

[0080] The first bismuth composition may contain at least one compound selected from the group consisting of compounds represented by the following formula (3e) and compounds represented by the following formula (3f):

[0081]

[0082]

[0083] [Method for Producing First Bismuth Compound] The method for producing the first bismuth compound is not particularly limited, but it is preferable to produce the first bismuth compound by reacting a second bismuth compound with a first phosphate ester. Specifically, it is preferable to produce the first bismuth compound by reacting the second bismuth compound with the first phosphate ester in an aliphatic hydrocarbon solvent or an aromatic solvent, optionally adding a polymerization inhibitor, and then dehydrating the resulting mixture.

[0084] The term "bismuth compound" refers to an organic compound containing bismuth. The bismuth compound includes bismuth (meth)acrylate or bismuth subsalicylate. The bismuth (meth)acrylate or bismuth subsalicylate is not particularly limited, and commercially available products can be used.

[0085] Bismuth subsalicylate is a compound in which salicylic acid is bonded to bismuth, and is represented by the following formula (VI).

[0086]

[0087] The method for producing bismuth subsalicylate is not particularly limited, and it can be produced by known methods.

[0088] The first phosphate ester may be a commercially available product. The first phosphate ester may be a phosphate ester having one (meth)acryloyl group, a phosphate ester having two (meth)acryloyl groups, or a mixture thereof.

[0089] Examples of phosphate esters having one (meth)acryloyl group include 2-(methacryloyloxy)ethyl dihydrogen phosphate and diphenyl-2-methacryloyloxyethyl phosphate.

[0090] Examples of phosphate esters having two (meth)acryloyl groups include bis[2-(methacryloxyoxy)ethyl] hydrogen phosphate and phenyl[2-(methacryloxyoxy)ethyl] hydrogen phosphate.

[0091] Furthermore, in order to improve compatibility, it is preferable to add a phosphate triester such as diphenyl-2-methacryloyloxyethyl phosphate, phenylbis[2-(methacryloyloxyethyl)]phosphate, or tris[2-(methacryloyloxyethyl)]phosphate as the first phosphate ester. Use of a phosphate triester having a phenyl group makes it possible to satisfactorily introduce a monovalent phenyl phosphate diester having one (meth)acryloyl group in the above formulas (III) to (V).

[0092] The amount of the phosphate triester blended is preferably 0.1 to 20 mol, and more preferably 0.2 to 5 mol, per 1 mol of the total of the phosphate ester having one (meth)acryloyl group and the phosphate ester having two (meth)acryloyl groups.

[0093] The amount of primary phosphate used may be determined so as to obtain the desired primary bismuth compound. Specifically, the amount of primary phosphate used is preferably in the range of 0.3 to 10 moles per mole of the secondary bismuth compound.

[0094] (Aliphatic hydrocarbon solvent or aromatic solvent) When producing the first bismuth compound, it is preferable to react the second bismuth compound and the first phosphate ester by stirring and mixing them in an aliphatic hydrocarbon solvent or aromatic solvent. Since water is generated in the reaction system during this reaction, it is preferable to dehydrate the generated water. In order to facilitate dehydration of the generated water, it is preferable to use an aliphatic hydrocarbon solvent or aromatic solvent having a high boiling point, specifically a boiling point of 100°C or higher. It is also possible to mix an aliphatic hydrocarbon solvent and an aromatic solvent and use the resulting mixture as a mixed solution.

[0095] Examples of aliphatic hydrocarbon solvents or aromatic solvents include hexane, heptane, nonane, decane, undecane, dodecane, xylene, dimethoxybenzene, and isomers thereof; benzene, toluene, chlorobenzene, bromobenzene, anisole; petroleum ether, petroleum benzine, and benzoin.

[0096] The amount of the aliphatic hydrocarbon solvent or aromatic solvent used is not particularly limited as long as it is an amount that allows the bismuth compound and the primary phosphate ester to be sufficiently mixed. In consideration of the productivity of the primary bismuth compound, it is preferable to use 5 to 100 mL of the aliphatic hydrocarbon solvent or aromatic solvent per 1 g of the primary bismuth compound.

[0097] (Reaction Conditions) The method for introducing the bismuth compound and the primary phosphate ester into the reaction system is not particularly limited. For example, a method can be employed in which a bismuth compound diluted with an aliphatic hydrocarbon solvent or aromatic solvent, if necessary, and a primary phosphate ester diluted with an aliphatic hydrocarbon solvent or aromatic solvent, if necessary, are added to the reaction system together and stirred and mixed. Alternatively, a method can be employed in which an aliphatic hydrocarbon solvent or aromatic solvent is first introduced into the reaction system, and then a bismuth compound diluted with an aliphatic hydrocarbon solvent or aromatic solvent, if necessary, and a primary phosphate ester diluted with an aliphatic hydrocarbon solvent or aromatic solvent, if necessary, are added together and stirred and mixed. Alternatively, a method can be employed in which one component is first introduced into the reaction system, and then the other component is introduced into the reaction system and stirred and mixed. Among these, the following method is preferred to reduce the coloration of the resulting primary bismuth compound and improve productivity. First, the bismuth compound is dispersed in an aliphatic hydrocarbon solvent or aromatic solvent. At this time, the bismuth compound may not dissolve, and in that case, it is preferable to pulverize the lumps of the bismuth compound using an ultrasonic device or the like so that no lumps of the bismuth compound remain. Thereafter, the primary phosphate ester is added to the cloudy solution in which the bismuth compound is dispersed, and stirring and heating are initiated.

[0098] The temperature (reaction temperature) at which the components are stirred may be the reflux temperature of the aliphatic hydrocarbon solvent or aromatic solvent. However, in order to further reduce coloration of the resulting bismuth compound, it is desirable to carry out the reaction at an oil bath temperature of preferably 30 to 150°C, more preferably 40 to 140°C, and even more preferably 45 to 120°C.

[0099] Furthermore, when the reaction temperature is 30 to 110°C, it is preferable to reduce the pressure in the reaction system in order to remove (dehydrate) water generated in the reaction system. In this case, dehydration can be carried out while mixing the bismuth compound and the primary phosphate ester, or the two can be mixed and then dehydrated. However, in consideration of the efficiency of the reaction, it is preferable to mix the two and then dehydrate them while allowing them to react.

[0100] The reaction time is not particularly limited and may usually be from 1 hour to 6 hours.

[0101] In consideration of operability, the atmosphere in which the reaction is carried out may be any of an air atmosphere, an inert gas atmosphere, and a dry air atmosphere, and in consideration of operability, the reaction is preferably carried out in an air atmosphere.

[0102] After the reaction under the above conditions, the resulting bismuth (I) compound is concentrated by distilling off the solvent, and if any insoluble turbid components are present, these are preferably separated by filtration or centrifugation. Furthermore, a solvent that is soluble in the reaction solvent used but does not dissolve the bismuth (I) compound is added to the concentrated reaction solution obtained by this treatment to perform reprecipitation and purification. If any high-boiling point solvent remains, the above decantation operation is repeated to replace the solvent. The remaining solvent is then distilled off and vacuum dried, allowing the bismuth (I) compound to be isolated.

[0103] In the curable composition, the content of the first bismuth compound is, for example, 30% by mass or more and 70% by mass or less. When the content of the first bismuth compound is high, the radiation shielding ability of the cured body tends to be enhanced. The content of the first bismuth compound is preferably 40% by mass or more, and more preferably 45% by mass or more. On the other hand, when the content of the first bismuth compound is excessively high, the anti-fogging properties of the cured body may be reduced. The content of the first bismuth compound is preferably 60% by mass or less, and more preferably 55% by mass or less. This content may be, for example, １ It can be measured by H NMR.

[0104] <Polymerizable Compound> The curable composition of the present disclosure contains a first radically polymerizable monomer as a polymerizable compound (excluding the first bismuth compound described above). The first radically polymerizable monomer has a polyethylene glycol chain and a radically polymerizable group. The polyethylene glycol chain has a —(CH ２ CH ２ O)n-, where n is the degree of polymerization.

[0105] The radical polymerizable group includes, for example, at least one selected from the group consisting of an (oxy)acryloyl group, an (oxy)methacryloyl group, a vinyl group, and an allyl group. The radical polymerizable group preferably includes at least one selected from the group consisting of an (oxy)acryloyl group and an (oxy)methacryloyl group. The number of radical polymerizable groups may be 1 or more, 2 or more, 3 or more, or 6 or less. The number of radical polymerizable groups is preferably 1, 2, or 3, and more preferably 1 or 2.

[0106] In the first radical polymerizable monomer, the ratio N2 / N1 of the number-average molecular weight N2 of the polyethylene glycol chain to the number-average molecular weight N1 is 75% or more and 95% or less. A high ratio N2 / N1 tends to improve the anti-fogging properties of the cured product. This ratio N2 / N1 is preferably 80% or more, more preferably 85% or more, and even more preferably 90% or more. This ratio N2 / N1 can be calculated, for example, from NMR spectroscopic analysis and the structural formula of the first radical polymerizable monomer. Hereinafter, this ratio N2 / N1 is also referred to as the EO ratio.

[0107] The number average molecular weight N1 refers to the molecular weight of the first radical polymerizable monomer. The number average molecular weight N1 of the first radical polymerizable monomer is, for example, 400 or more and 3000 or less. The number average molecular weight N1 is preferably 500 or more and 1500 or less, more preferably 600 or more and 1400 or less, and even more preferably 800 or more and 1300 or less. The number average molecular weight N1 can be calculated, for example, from NMR spectroscopic analysis and the structural formula of the first radical polymerizable monomer.

[0108] The number average molecular weight N2 refers to the molecular weight of the polyethylene glycol chain portion in the first radical polymerizable monomer. The number average molecular weight N2 of the polyethylene glycol chain portion of the first radical polymerizable monomer is, for example, 350 or more and 2200 or less, preferably 400 or more and 1500 or less, and more preferably 500 or more and 1200 or less. The number average molecular weight N2 can be calculated, for example, from NMR spectroscopic analysis and the structural formula of the first radical polymerizable monomer.

[0109] The degree of polymerization of the polyethylene glycol chain of the first radical polymerizable monomer is, for example, 8 or more and 50 or less, preferably 10 or more and 30 or less, and more preferably 12 or more and 25 or less. The degree of polymerization can be calculated, for example, from NMR spectroscopic analysis and the structural formula of the first radical polymerizable monomer.

[0110] The first radical polymerizable monomer preferably contains a (meth)acrylate represented by the following formula (I):

[0111]

[0112] In the above formula (I), R １ is a hydrogen atom or a methyl group. １ When R is a hydrogen atom, that is, when the first radical polymerizable monomer is an acrylate, the anti-fogging properties of the cured product tend to be enhanced. １ When is a methyl group, that is, when the first radical polymerizable monomer is a methacrylate, the hardness of the cured body tends to increase.

[0113] R ２ is an acryloyl group, a methacryloyl group, a methyl group, or a phenyl group. ２ When R is an acryloyl group or a methacryloyl group, that is, when the first radical polymerizable monomer is a bifunctional (meth)acrylate, the hardness of the cured body tends to be increased. ２ When is a methyl group or a phenyl group, that is, when the first radically polymerizable monomer is a monofunctional (meth)acrylate, the antifogging properties of the cured body tend to be enhanced.

[0114] n represents the degree of polymerization and is an integer of 10 to 30. From the viewpoint of improving the anti-fogging properties of the cured product, n is preferably 12 or more, more preferably 13 or more, and even more preferably 20 or more. From the viewpoint of improving the hardness of the cured product, n is preferably 25 or less, more preferably 20 or less, and even more preferably 15 or less.

[0115] The first radical polymerizable monomer preferably includes at least one selected from the group consisting of monofunctional acrylates, bifunctional acrylates, monofunctional methacrylates, and bifunctional methacrylates, and may include two or more, or may include three or more.

[0116] Specific examples of the monofunctional acrylate include at least one selected from the group consisting of methoxypolyethylene glycol acrylate, phenoxydiethylene glycol acrylate, and ethoxylated-O-phenylphenol acrylate.

[0117] Specific examples of the monofunctional methacrylate include at least one selected from the group consisting of methoxypolyethylene glycol methacrylate, phenoxydiethylene glycol methacrylate, and ethoxylated-O-phenylphenol methacrylate.

[0118] Specific examples of the diacrylate include at least one selected from the group consisting of polyethylene glycol diacrylate, ethoxylated glycerin diacrylate, and pentaerythritol diacrylate.

[0119] Specific examples of dimethacrylates include at least one selected from the group consisting of polyethylene glycol dimethacrylate, ethoxylated glycerin dimethacrylate, and pentaerythritol dimethacrylate.

[0120] In the curable composition, the proportion of the first radical polymerizable monomer is, for example, 15% by mass or more. From the viewpoint of improving anti-fogging properties, this proportion is preferably 17% by mass or more, more preferably 20% by mass or more, and even more preferably 25% by mass or more. From the viewpoint of improving the hardness of the cured body, this proportion is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less. This proportion can be, for example, １ It can be measured by H NMR.

[0121] When the first radical polymerizable monomer contains a bifunctional radical polymerizable monomer and a monofunctional radical polymerizable monomer, the proportion of the bifunctional radical polymerizable monomer in the curable composition is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, from the viewpoint of increasing the hardness of the cured body. From the viewpoint of increasing the anti-fogging properties of the cured body, this proportion is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less. From the viewpoint of increasing the anti-fogging properties of the cured body, the proportion of the monofunctional radical polymerizable monomer in the curable composition is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more. From the viewpoint of increasing the hardness of the cured body, this proportion is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.

[0122] In the curable composition, the ratio M1 / M2 of the mass M1 of the first bismuth compound to the mass M2 of the first radical polymerizable monomer is preferably 1 or more and 10 or less. When this ratio M1 / M2 is high, the radiation shielding ability of the cured product tends to be enhanced. When this ratio M1 / M2 is low, the anti-fogging property of the first bismuth compound tends to be enhanced. More preferably, this ratio M1 / M2 is 2 or more and 5 or less.

[0123] In the curable composition, the proportion of polyethylene glycol chains, i.e., the EO content, is 13.5% by mass or more. This polyethylene glycol chain is mainly derived from the first radical polymerizable monomer. In order to improve the anti-fogging properties of the cured body, the proportion of polyethylene glycol chains in the curable composition is preferably 13.6% by mass or more, more preferably 14.0% by mass or more, even more preferably 16.0% by mass or more, particularly preferably 18.0% by mass or more, and extremely preferably 20.0% by mass or more. In order to improve the hardness of the cured body, this proportion is preferably 40.0% by mass or less, more preferably 30.0% by mass or less, and even more preferably 25.0% by mass or less. This proportion can be obtained, for example, by multiplying the proportion of the first radical polymerizable monomer in the curable composition by the EO ratio of the first radical polymerizable monomer.

[0124] The curable composition of the present disclosure may contain a second radical polymerizable monomer in addition to the first radical polymerizable monomer. The second radical polymerizable monomer is a radical polymerizable monomer that does not have an ethylene glycol chain and has a radical polymerizable group.

[0125] The radical polymerizable group includes, for example, at least one selected from the group consisting of an (oxy)acryloyl group, an (oxy)methacryloyl group, a vinyl group, and an allyl group. The radical polymerizable group preferably includes at least one selected from the group consisting of an (oxy)acryloyl group and an (oxy)methacryloyl group. The number of radical polymerizable groups may be 1 or more, 2 or more, 3 or more, or 6 or less. The number of radical polymerizable groups is preferably 1, 2, or 3, and more preferably 1 or 2.

[0126] The number average molecular weight of the second radical polymerizable monomer is, for example, from 100 to 2000. The number average molecular weight is preferably from 120 to 1500, more preferably from 130 to 1000, and even more preferably from 140 to 500. The number average molecular weight can be calculated, for example, from NMR spectroscopic analysis and the structural formula of the second radical polymerizable monomer.

[0127] The second radical polymerizable monomer preferably contains a compound represented by the following formula (II):

[0128]

[0129] In the above formula (II), R ３ is a hydrogen atom or a methyl group. ３ When R is a hydrogen atom, that is, when the second radical polymerizable monomer is an acrylate, the anti-fogging properties of the cured product tend to be enhanced. ３ When is a methyl group, that is, when the second radical polymerizable monomer is a methacrylate, the hardness of the cured body tends to increase.

[0130] R ４ is an alkylene group having 1 to 5 carbon atoms. ４ is preferably a methylene group or an ethylene group, and m is 0 or 1.

[0131] R ５ R is an alkyl group having 1 to 5 carbon atoms, a phenyl group, a dimethylamino group, a diethylamino group, an acryloyloxy group, or a methacryloyloxy group. ５ When R is an acryloyloxy group or a methacryloyloxy group, that is, when the second radical polymerizable monomer is a bifunctional (meth)acrylate, the hardness of the cured body tends to be increased. ５ When is another group, that is, when the second radically polymerizable monomer is a monofunctional (meth)acrylate, the antifogging properties of the cured product tend to be enhanced.

[0132] The second radical polymerizable monomer preferably includes at least one selected from the group consisting of monofunctional acrylates, bifunctional acrylates, monofunctional methacrylates, and bifunctional methacrylates, and may include two or more, or may include three or more.

[0133] Specific examples of the monofunctional acrylate include at least one selected from the group consisting of 2-(dimethylamino)ethyl acrylate, acrylic acid, acrylamide, phenyl acrylate, benzyl acrylate, isobutyl acrylate, methoxyethyl acrylate, ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, isocyanatoethyl acrylate, and acryloxymethyltrimethoxysilane.

[0134] Specific examples of the monofunctional methacrylate include at least one selected from the group consisting of 2-(dimethylamino)ethyl methacrylate, methacrylic acid, methacrylamide, phenyl methacrylate, benzyl methacrylate, isobutyl methacrylate, methoxyethyl methacrylate, ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, isocyanatoethyl methacrylate, and netacryloxymethyltrimethoxysilane.

[0135] Specific examples of diacrylates include at least one selected from the group consisting of ethylene glycol diacrylate, propylene glycol diacrylate, and tetramethylene glycol diacrylate.

[0136] Specific examples of dimethacrylate include at least one selected from the group consisting of ethylene glycol dimethacrylate, propylene glycol dimethacrylate, and tetramethylene glycol dimethacrylate.

[0137] In the curable composition, the proportion of the second radical polymerizable monomer is, for example, 10% by mass or more and 40% by mass or less. From the viewpoint of increasing hardness, this proportion is preferably 15% by mass or more, more preferably 20% by mass or more, and even more preferably 25% by mass or more. From the viewpoint of increasing the anti-fogging properties of the cured product, this proportion is preferably 35% by mass or less, more preferably 33% by mass or less, and even more preferably 30% by mass or less. This proportion can be, for example, １ It can be measured by H NMR.

[0138] In the curable composition, the ratio M1 / M3 of the mass M1 of the first bismuth compound to the mass M3 of the second radical polymerizable monomer is preferably 0.5 or more and 10 or less. When this ratio M1 / M3 is high, the radiation shielding ability of the cured product tends to be enhanced. When this ratio M1 / M3 is low, the moldability of the first bismuth compound tends to be enhanced. More preferably, this ratio M1 / M3 is 1 or more and 5 or less.

[0139] In the curable composition, the ratio M2 / M3 of the mass M2 of the first radical polymerizable monomer to the mass M3 of the second radical polymerizable monomer is preferably 0.1 or more and 10 or less. When this ratio M2 / M3 is high, the anti-fogging properties of the cured body tend to be enhanced. When this ratio M2 / M3 is low, the moldability of the first bismuth compound tends to be enhanced. This ratio M2 / M3 is more preferably 0.2 or more and 2 or less, and even more preferably 0.5 or more and 1 or less.

[0140] The curable composition of the present disclosure may contain, in addition to the first radical polymerizable monomer and the second radical polymerizable monomer, other polymerizable compounds, such as compounds having a vinyl group and compounds having an allyl group.

[0141] Examples of polymerizable compounds having a vinyl group include vinylpyridine, vinylpyrrolidone; styrene derivatives such as methylstyrene and its structural isomers, methoxystyrene and its structural isomers, methylstyrene dimer, chlorostyrene, bromostyrene, and divinylbenzene; and the like.

[0142] Examples of polymerizable compounds having an allyl group include allyl methyl carbonate, allyl phenyl ether, 4-allyloxytoluene, allyloxytrimethylsilane, allyl benzoate, allyl methacrylate, and allyl glycidyl ether.

[0143] The curable composition of the present disclosure may contain 10% by mass or less of a nitrile compound. The content of the nitrile compound in the curable composition is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less. If the content of the nitrile compound is low, the odor level of the cured product tends to decrease. The lower limit of the content of the nitrile compound is, for example, 100 ppm by mass or more, and, for another example, 0% by mass. This content may be, for example, １ It can be measured by H NMR.

[0144] Examples of the nitrile compound include acrylonitrile, methacrylonitrile, crotononitrile, 2-chloroacrylonitrile, 2-cyanoethyl acrylate, allyl cyanide, allyl cyanoacetate, fumaronitrile, and 5-norbornene-2-carbonitrile.

[0145] <Other Compounding Agents> The curable composition of the present disclosure may contain known compounding agents, coordinating organic compounds, terpenes, and the like, in addition to the bismuth(II) compound and the polymerizable compound.

[0146] Examples of known compounding agents include radical polymerization initiators, antioxidants, release agents for improving releasability from a mold, dyes for adjusting the color tone of the cured product, chain transfer agents for controlling polymerization, plasticizers for improving the plasticity of the cured product or imparting heat resistance or cold resistance, antioxidants for improving durability, and antiaging agents.

[0147] These compounding agents can be blended in an amount that does not impair the effects. For example, each compounding agent is blended in an amount of preferably 0 to 30 parts by mass, more preferably 0.01 to 20 parts by mass, and even more preferably 0.02 to 15 parts by mass, per 100 parts by mass of the total of the first bismuth compound and the polymerizable compound.

[0148] The curable composition of the present disclosure can be produced by mixing a bismuth(II) compound, a polymerizable compound, and various compounding ingredients that are compounded as needed.

[0149] [Coordinating Organic Compound] The coordinating organic compound is an organic compound that can coordinate with bismuth, and can function as an odor suppressant and viscosity adjuster for the cured product.

[0150] The acid dissociation constant pKa of the coordinating organic compound is preferably 2.0 or more and 15.0 or less. Using a coordinating organic compound with an acid dissociation constant pKa within this range tends to produce a cured product with low yellowness and odor. The acid dissociation constant pKa of the coordinating organic compound may be 3 or more, 4 or more, or 6 or more. The acid dissociation constant pKa of the coordinating organic compound may be 14 or less, 11 or less, or 10 or less. The acid dissociation constant pKa refers to the acid dissociation constant in water. This acid dissociation constant pKa can be calculated experimentally, for example, by titration or by calculation assuming certain conditions. Specifically, calculation results using ACD / Lab's software V11.02 described in SciFinder-n can be used. Although this value is based on the assumption of water, it is used as a unified physical property index for each compound.

[0151] The molecular weight (relative molecular mass) of the coordinating organic compound is preferably 17 or more and 400 or less. Coordinating organic compounds with molecular weights within this range are thought to be more likely to coordinate with bismuth. The molecular weight of the coordinating organic compound is more preferably 18 or more and 300 or less, and even more preferably 28 or more and 200 or less.

[0152] The boiling point of the coordinating organic compound at 1 atmosphere is preferably 20°C or higher and 500°C or lower. Use of a coordinating organic compound having a boiling point within this range tends to further reduce the odor of the cured product. The boiling point of the coordinating organic compound is more preferably 30°C or higher and 400°C or lower, and even more preferably 120°C or higher and 360°C or lower.

[0153] In the curable composition, the ratio M1 / M4 of the mass M1 of the first bismuth compound to the mass M4 of the coordinating organic compound is, for example, 4 or more and 4990 or less. When this ratio M1 / M4 is high, the radiation shielding ability of the cured body tends to be enhanced. When this ratio M1 / M4 is low, the odor of the cured body tends to be reduced. This ratio M1 / M4 is preferably 10 or more and 700 or less, more preferably 15 or more and 300 or less, and even more preferably 20 or more and 100 or less. This ratio can be, for example, １ It can be measured by H NMR.

[0154] When the proportion of the coordinating organic compound in the curable composition is high, the odor of the cured product tends to be reduced. The proportion of the coordinating organic compound is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1.0% by mass or more. On the other hand, when the proportion of the coordinating organic compound is excessively high, the radiation shielding ability of the cured product may be reduced. The proportion of the coordinating organic compound is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less.

[0155] Examples of the coordinating organic compound include a compound having an imidazole skeleton, a compound having a pyrazole skeleton, a compound having a triazole skeleton, a compound having a tetrazole skeleton, a compound having an unsaturated bond and at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, an unsaturated dicarboxylic acid, an unsaturated carboxylic acid ester, an unsaturated carboxylic acid anhydride, etc. Note that even if the coordinating organic compound has a radical polymerizable group such as a (meth)acryloyl group, the coordinating organic compound is not included in the above-mentioned polymerizable compound.

[0156] The coordinating organic compound preferably includes at least one selected from the group consisting of a compound having an imidazole skeleton, a compound having a pyrazole skeleton, a compound having a triazole skeleton, and a compound having a tetrazole skeleton.

[0157] The compound having an imidazole skeleton has a skeleton represented by the following formula (a).

[0158]

[0159] Examples of compounds having an imidazole skeleton include imidazole, 1-vinylimidazole, 1-allylimidazole, N-acetylimidazole, benzimidazole, 1-methylimidazole, 1-ethylimidazole, 1-propylimidazole, 1-cyanomethylimidazole, 1-(3-aminopropyl)imidazole, 2-methylimidazole, 2-methyl-1-vinylimidazole, 2-hydroxymethyl-1-methylimidazole, 4-hydroxymethyl-5-methylimidazole, 2-formyl-1-vinylimidazole, and 2-ethylimidazole. The compound having an imidazole skeleton preferably contains at least one compound selected from the group consisting of imidazole, 1-vinylimidazole, 1-allylimidazole, 2-methylimidazole, N-acetylimidazole, trimethylsilylimidazole, and 1,2-dimethylimidazole, and more preferably contains imidazole.

[0160] The compound having a pyrazole skeleton has a skeleton represented by the following formula (b).

[0161]

[0162] Examples of compounds having a pyrazole skeleton include pyrazole, 1-methylpyrazole, 1-ethylpyrazole, 1-isopropylpyrazole, 1-nitropyrazole, 3-methylpyrazole, 3-aminopyrazole, 3-nitropyrazole, 4-methylpyrazole, 4-aminopyrazole, 4-chloropyrazole, 4-nitropyrazole, 3-amino-1-methylpyrazole, 3-amino-5-methylpyrazole, 3-amino-5-hydroxypyrazole, 5-amino-1-methylpyrazole, 5-hydroxy-1-methylpyrazole, ... The compound having a pyrazole skeleton preferably contains at least one compound selected from the group consisting of 1,2-dihydropyrazol-3-one, 3-formylpyrazole, 1,3-dimethylpyrazole, 1,5-dimethylpyrazole, 3,5-dimethylpyrazole, 3-amino-4-cyanopyrazole, 4-formyl-1-methylpyrazole, 1,3,5-trimethylpyrazole, 5-amino-1,3-dimethylpyrazole, 5-amino-1-ethylpyrazole, pyrazole-4-carboxylic acid, pyrazole-3-carboxylic acid, and 5-(hydroxymethyl)-1-methylpyrazole.

[0163] The compounds having a triazole skeleton include compounds having a 1,2,3-triazole skeleton and compounds having a 1,2,4-triazole skeleton.

[0164] The compound having a 1,2,3-triazole skeleton has a skeleton represented by the following formula (c).

[0165]

[0166] The compound having a 1,2,3-triazole skeleton includes, for example, at least one compound selected from the group consisting of 1,2,3-triazole, 1H-benzotriazole, and 2H-benzotriazole. The compound having a 1,2,3-triazole skeleton preferably includes 1,2,3-triazole.

[0167] The compound having a 1,2,4-triazole skeleton has a skeleton represented by the following formula (d).

[0168]

[0169] The compound having a 1,2,4-triazole skeleton includes, for example, at least one compound selected from the group consisting of 1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole, 1-hydroxymethyl-1,2,4-triazole, 3,5-dimethyl-1,2,4-triazole, 3,5-amino-1,2,4-triazole, and methyl 1,2,4-triazole-3-carboxylate. The compound having a 1,2,4-triazole skeleton preferably includes 1,2,4-triazole.

[0170] The compound having a tetrazole skeleton has a skeleton represented by the following formula (e).

[0171]

[0172] The compound having a tetrazole skeleton includes, for example, at least one compound selected from the group consisting of tetrazole, 1-methyl-1H-tetrazole, 5-methyltetrazole, 5-amino-1H-tetrazole, 5-amino-1-methyltetrazole, and 5-(2-pyridyl)-1H-tetrazole. The compound having a tetrazole skeleton preferably includes tetrazole.

[0173] The coordinating organic compound includes, for example, a compound having an unsaturated bond and at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms is, for example, 1 to 5, preferably 1 or 2. Examples of such compounds include the above-mentioned compounds having an imidazole skeleton, as well as at least one compound selected from the group consisting of allyl isonicotinate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, indole, carbazole, 1,2-benzisothiazol-3(2H)-one, heliotropine, allyl cyanurate, triallyl isocyanurate, triallylamine, 2-(tert-butylamino)ethyl acrylate, and 2-(tert-butylamino)ethyl methacrylate.

[0174] The coordinating organic compound includes, for example, an unsaturated dicarboxylic acid. Examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, citraconic acid, mesaconic acid, 2-pentenedioic acid, methylenesuccinic acid, allylmalonic acid, isopropylidesuccinic acid, 2,4-hexadienedioic acid, and acetylenedicarboxylic acid. The unsaturated dicarboxylic acid preferably includes maleic acid.

[0175] The coordinating organic compound includes, for example, an unsaturated carboxylic acid ester. Examples of the unsaturated carboxylic acid ester include 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, and diallyl maleate. The unsaturated carboxylic acid ester preferably includes at least one compound selected from the group consisting of 2-dimethylaminoethyl acrylate and 2-dimethylaminoethyl methacrylate.

[0176] The coordinating organic compound includes, for example, an unsaturated carboxylic acid anhydride, such as methacrylic acid anhydride or maleic acid anhydride.

[0177] Specific preferred examples of the coordinating organic compound include imidazole, 1-vinylimidazole, 1-allylimidazole, N-acetylimidazole, trimethylsilylimidazole, pyrazole, triazole, 1H-tetrazole, 1,2,3-benzotriazole, benzimidazole, allyl isonicotinate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, indole, carbazole, 2-methylimidazole, 4-methylimidazole, 1,2-benzisothiazoline, and the like. At least one compound selected from the group consisting of azol-3(2H)-one, 2-isopropylimidazole, 1,2-dimethylimidazole, I-menthol, heliotropin, triallyl cyanurate, triallyl isocyanurate, triallylamine, 2-(tert-butylamino)ethyl acrylate, 2-(tert-butylamino)ethyl methacrylate, 4-acryloylmorpholine, triacryloylhexahydrotriazine, dimethylpyrazole, linalool, camphor, acrylic acid, methacrylic acid, maleic acid, acrylic anhydride, methacrylic anhydride, and maleic anhydride may be mentioned.

[0178] The coordinating organic compound preferably contains at least one compound selected from the group consisting of imidazole, 2-methylimidazole, 1-vinylimidazole, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, triallylamine, and maleic anhydride.

[0179] Carboxylic acid anhydrides can be used as carboxylic acid precursors. The acid dissociation constant pKa of the corresponding carboxylic acid is used.

[0180] The coordinating organic compound preferably includes a first coordinating organic compound and a second coordinating organic compound different from the first coordinating organic compound. When multiple types of coordinating organic compounds are included, the odor can be further reduced due to the synergistic effect of these compounds.

[0181] The coordinating organic compound preferably contains at least one compound selected from the group consisting of a compound having a pyrazole skeleton, a compound having a triazole skeleton, a compound having a tetrazole skeleton, a compound having an unsaturated bond and at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, an unsaturated dicarboxylic acid, an unsaturated carboxylic acid ester, and an unsaturated carboxylic acid anhydride, and a compound having an imidazole skeleton. When the curable composition contains a compound having an imidazole skeleton, the viscosity of the curable composition tends to decrease and the handleability tends to improve.

[0182] In the coordinating organic compound containing multiple types, the proportion of the compound having an imidazole skeleton is preferably 10% by mass or more, more preferably 25% by mass or more, and even more preferably 40% by mass or more. In one example, the proportion of the compound having an imidazole skeleton is 90% by mass or less, and in another example, 60% by mass or less.

[0183] The coordinating organic compound preferably contains at least one compound selected from the group consisting of a compound having an imidazole skeleton, a compound having a pyrazole skeleton, a compound having a triazole skeleton, a compound having a tetrazole skeleton, a compound having an unsaturated bond and at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, an unsaturated dicarboxylic acid, and an unsaturated carboxylic acid ester, and an unsaturated carboxylic acid anhydride. When an unsaturated carboxylic acid anhydride is contained, water absorption tends to be enhanced.

[0184] In the coordinating organic compound containing multiple types of unsaturated carboxylic acid anhydrides, the proportion of the unsaturated carboxylic acid anhydride is preferably 10% by mass or more, more preferably 25% by mass or more, and even more preferably 40% by mass or more. In one example, the proportion of the unsaturated carboxylic acid anhydride is 90% by mass or less, and in another example, 60% by mass or less.

[0185] The coordinating organic compound preferably contains both a compound having an imidazole skeleton and an unsaturated carboxylic acid anhydride. The coordinating organic compound may contain only a compound having an imidazole skeleton and an unsaturated carboxylic acid anhydride, or may contain other compounds.

[0186] [Terpenes] Terpenes include terpenes and derivatives thereof, and can function as odor suppressants for the cured product. Terpenes are hydrocarbons whose structural unit is isoprene.

[0187] Terpenes include, for example, at least one compound selected from the group consisting of semiterpenes, semiterpene derivatives, monoterpenes, monoterpene derivatives, sesquiterpenes, and sesquiterpene derivatives. The terpenes preferably include at least one compound selected from the group consisting of monoterpenes, monoterpene derivatives, sesquiterpenes, and sesquiterpene derivatives, and more preferably include at least one compound selected from the group consisting of monoterpenes and monoterpene derivatives. The various derivatives may have functional groups such as hydroxyl groups and carbonyl groups.

[0188] The terpenes preferably include at least one compound selected from the group consisting of monocyclic monoterpenes, monocyclic monoterpene derivatives, polycyclic monoterpenes, and polycyclic monoterpene derivatives. When these monoterpenes are included, the odor of the cured product tends to be further reduced.

[0189] Specific examples of terpenes include at least one compound selected from the group consisting of (-)-α-pinene, (-)-β-pinene, (±)-camphene, α-terpinene, limonene, phenetole, p-cymene, terpinolene, 1,8-cineole, linalool, (+)-camphor, l-menthol, d-menthol, 1,4-cineole, nopinene, α-phellandrene, fenchone, borneol, and citronellol.

[0190] The terpenes preferably include at least one selected from the group consisting of (-)-α-pinene, (-)-β-pinene, (±)-camphene, α-methylstyrene, α-terpinene, limonene, phenetole, p-cymene, terpinolene, 1,8-cineole, linalool, (+)-camphor, and 1-menthol. The terpenes more preferably include at least one selected from the group consisting of (-)-α-pinene, (-)-β-pinene, (±)-camphene, α-methylstyrene, limonene, phenetole, p-cymene, linalool, and (+)-camphor.

[0191] The boiling point of the terpenes at 1 atmosphere is preferably 95°C or higher and 250°C or lower. Using terpenes having a boiling point within this range tends to further reduce the odor of the cured product. The boiling point of the terpenes is more preferably 100°C or higher and 220°C or lower, and even more preferably 150°C or higher and 210°C or lower. The boiling point of the terpenes can be measured, for example, using an ebulliometer.

[0192] In the curable composition, the ratio M1 / M5 of the mass M1 of the first bismuth compound to the mass M5 of the terpenes is, for example, 4 or more and 4990 or less. When this ratio M1 / M5 is high, the radiation shielding ability of the cured body tends to be enhanced. When this ratio M1 / M5 is low, the odor of the cured body tends to be reduced. This ratio M1 / M5 is preferably 10 or more and 700 or less, more preferably 15 or more and 300 or less, and even more preferably 20 or more and 100 or less. This ratio can be, for example, １ It can be measured by H NMR.

[0193] When the proportion of terpenes in the curable composition is high, the odor of the cured product tends to be reduced. The proportion of terpenes is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1.0% by mass or more. On the other hand, if the proportion of terpenes is excessively high, the radiation shielding ability of the cured product may be reduced. The proportion of terpenes is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less. These proportions can be determined, for example, as follows: １ It can be measured by H NMR.

[0194] <Method for Producing Cured Product> A known method can be used to obtain a cured product by curing the curable composition of the present disclosure. Specifically, photopolymerization, thermal polymerization, or both of these polymerization methods can be used. The preferred polymerization method is determined by the radical polymerization initiator that is added as needed.

[0195] <Physical Properties of Cured Product> The curable composition of the present disclosure can produce a cured product that is highly transparent and flexible and has little coloration, while containing a high concentration of bismuth, which has a high radiation blocking ability for X-rays and the like. The cured product obtained by curing the curable composition can have a thickness of 2 mm, a transmittance at a wavelength of 560 nm of 80% or more, an X-ray blocking ability equivalent to 0.02 mm of lead foil or more, and a yellowness index of 40 or less.

[0196] The amount of bismuth contained in the cured product can be 5 to 40% by mass, assuming the total mass of the cured product to be 100% by mass. The amount of bismuth is preferably 20% by mass or more, and more preferably 25% by mass or more. The proportion of bismuth in the cured product (resin composition) can be measured, for example, by fluorescent X-ray analysis.

[0197] This cured product may be a resin composition containing bismuth, a (meth)acrylic resin, and 16.0% by mass or more of polyethylene glycol chains. The polyethylene glycol chains constitute part of the (meth)acrylic resin. The proportion of polyethylene glycol chains in the resin composition may be 17.0% by mass or more, or may be 19.0% by mass or more. There is no particular upper limit for the proportion of polyethylene glycol chains in the resin composition, but in one example, it is 30.0% by mass or less, and in another example, it is 25.0% by mass or less. The proportion of polyethylene glycol chains in the resin composition can be measured, for example, by NMR spectroscopic analysis.

[0198] <Applications of Cured Product> The cured product obtained by curing the curable composition of the present disclosure is lightly colored and transparent, and therefore can be used as an optical article. Furthermore, because it has radiation shielding ability despite being visible light transparent, it can be used as a transparent radiation shielding material. In addition, because a large-area, flexible sheet can be obtained, it can be easily formed into a shape suited to the application or object.

[0199] An optical article comprising the cured product of the present disclosure can be used as a sheet for a radiation-shielding window material, a radiation-shielding lens, a radiation protection curtain, etc.

[0200] A lens or sheet comprising the cured product of the present disclosure can be used as radiation shielding glasses or a radiation shield.

[0201] Furthermore, since the cured product of the present disclosure has antibacterial and antiviral properties, it can be used in applications where high hygiene is desired.

[0202] EXAMPLES The present invention will be described in detail below using examples and comparative examples, but the present invention is not limited to the following examples.

[0203] Example 1 (Production of Bismuth (I) Compound) 94.27 g of bismuth(III) subsalicylate (Sigma-Aldrich, 260.35 mmol in terms of bismuth), 33.06 g of a mixture of bis[(2-methacryloyloxyethyl)]phosphate, a phosphoric acid diester, and (2-methacryloyloxyethyl)phosphate, a phosphoric acid monoester (Daihachi Chemical Industry Co., Ltd., MR-200, 162.04 mmol as a phosphoric acid value), 33.09 g of diphenyl-2-methacryloyloxyethyl phosphate, a phosphoric acid triester (Daihachi Chemical Industry Co., Ltd., MR-260, 91.33 mmol), and 6.17 g of dibutylhydroxytoluene (BHT, Fujifilm Wako Pure Chemical Industries, Ltd., special grade reagent) as a polymerization inhibitor were placed in a 1000 mL eggplant-shaped flask, and 750 mL of toluene was added. The mixture was ultrasonically dispersed using a bath-type sonicator to form a cloudy white solution.

[0204] The resulting cloudy solution was transferred to a 1000 mL four-neck flask equipped with a Dean-Stark trap, and the reaction was carried out with heating and stirring at 130°C in an oil bath, and the produced water was removed from the system. The reaction was terminated when no more water was produced. A pale yellow, scattered solution was obtained, with a slight amount of pale yellow precipitate.

[0205] This solution was concentrated to 250 mL using a vacuum evaporator. 8 g of alumina powder was added, and the mixture was left to stand overnight. Then, suction filtration was performed using 5B filter paper. 3 g of activated carbon (Norit, Darco G60) was added to the resulting pale yellow, scattered filtrate, and the mixture was centrifuged at 23,830 × g for 8 hours. The centrifuged supernatant was pressure-filtered through a 0.2 μm pore membrane filter, yielding a pale yellow, transparent filtrate. The solvent was removed from this solution using a vacuum evaporator, and the mixture was redissolved in 250 mL of acetone. 3 g of activated carbon (Norit, Norit SX-Plus) was added to the resulting pale yellow solution, and the mixture was centrifuged at 23,830 × g for 12 hours. The centrifuged supernatant was pressure-filtered through a 0.2 μm pore membrane filter, yielding a pale yellow, transparent filtrate. The resulting filtrate was concentrated to 100 mL using a vacuum evaporator. The acetone solution was poured into 800 mL of hexane in a 1000 mL conical beaker while stirring. The resulting white precipitate was collected by suction filtration using 5B filter paper, and the resulting solid was dried under vacuum. 64.40 g of a white powder of bismuth (II) compound (phosphate ester-bound bismuth-containing composition) was obtained.

[0206] (Analysis of Bismuth(II) Compound) For IR measurement, a Fourier transform infrared spectrophotometer (Spectrum One, manufactured by PerkinElmer) was used. Measurement was performed by the single reflection ATR method, with four reflections integrated. As a result, the spectrum of the obtained bismuth(II) compound showed a peak at 1697 cm －１ A peak was confirmed.

[0207] For the MALDI-TOF-MS measurement, a Rapiflex TOF / TOF model manufactured by Bruker was used. CHCA (α-cyano-4-hydroxycinnamic acid), DIT (Dithranol), and DHB (2,5-Dihydroxybenzoic acid) were used as matrices, and sodium trifluoroacetate was used as a cationizing agent. Measurement was performed in Reflector / Positive mode, with a mass range of m / z = 20 to 4000. As a result, the compounds represented by the above formulas (3a), (3b), and (3f) were confirmed.

[0208] (Proportion of Bismuth in the First Bismuth Compound) The proportion of bismuth in the first bismuth compound was measured by ICP spectrochemical emission analysis, and the result was that the proportion of bismuth was 46 mass %.

[0209] (Preparation of Curable Composition) 52 parts by mass of the first bismuth compound obtained above, 16 parts by mass of methoxypolyethylene glycol methacrylate (M-130G) having an ethylene glycol chain polymerization degree of 13, 24.8 parts by mass of methoxyethyl methacrylate (MEMA), and 6 parts by mass of 2-(dimethylamino)ethyl methacrylate (DMAEMA) were mixed. To this, 0.9 parts by mass of imidazole (IMD), 0.3 parts by mass of methylstyrene dimer (MSD), and 0.01 parts by mass of modified silicone oil (KF353A) were added and dissolved uniformly to obtain a curable composition. This curable composition was placed under reduced pressure using a vacuum pump, and dissolved oxygen was removed. The proportion of ethylene glycol chains in this curable composition, i.e., the EO content, was 13.6% by mass.

[0210] (Production of cured product) The curable composition obtained above was poured into two glass plates (110 mm × 300 mm) spaced apart and fixed with a 3 mm square silicone resin cord to maintain a gap of 3 mm, and the temperature was raised to a maximum temperature of 90°C over 15 hours and maintained at 90°C for 2 hours to allow polymerization, yielding a pale yellow, transparent cured product.

[0211] Examples 2 to 12 and Comparative Examples 1 to 3 Cured products were produced in the same manner as in Example 1, except that the formulation of the curable composition was changed as shown in Table 1. In Comparative Examples 2 and 3, the amount of methylstyrene dimer (MSD) was changed to 0.9 parts by mass.

[0212] The materials shown in Table 1 are summarized below. (First radical polymerizable monomer) M-130G: methoxypolyethylene glycol methacrylate having a degree of polymerization of ethylene glycol chains of 13, a number average molecular weight N1 of 673, and a proportion of ethylene glycol chains (EO ratio) of 85% M-230G: methoxypolyethylene glycol methacrylate having a degree of polymerization of ethylene glycol chains of 23, a number average molecular weight N1 of 1113, and a proportion of ethylene glycol chains (EO ratio) of 91% A-1000: polyethylene glycol diacrylate having a degree of polymerization of ethylene glycol chains of 23, a number average molecular weight N1 of 1139, and a proportion of ethylene glycol chains (EO ratio) of 89% 9G: polyethylene glycol dimethacrylate having a degree of polymerization of ethylene glycol chains of 9, a number average molecular weight N1 of 551, and a proportion of ethylene glycol chains (EO ratio) of 72% 14G: Polyethylene glycol dimethacrylate in which the degree of polymerization of the ethylene glycol chain is 14, the number average molecular weight N1 is 771, and the proportion of the ethylene glycol chain (EO ratio) is 80%. 23G: Polyethylene glycol dimethacrylate in which the degree of polymerization of the ethylene glycol chain is 23, the number average molecular weight N1 is 1167, and the proportion of the ethylene glycol chain (EO ratio) is 87%. AM-130G: Methoxypolyethylene glycol acrylate in which the degree of polymerization of the ethylene glycol chain is 13, the number average molecular weight N1 is 659, and the proportion of the ethylene glycol chain (EO ratio) is 88%.

[0213] (Second radical polymerizable monomer) MEMA: methoxyethyl methacrylate DMAEMA: 2-(dimethylamino)ethyl methacrylate THFAA: tetrahydrofurfuryl acrylate

[0214] <Evaluation Tests> [Impact Resistance Test] A ball drop test was conducted to evaluate the impact resistance of the resulting cured body. First, a support ring made of NBR was bonded to a tube with an inner diameter of 25 mm, an outer diameter of 32 mm, and a height of 25 mm. The support ring had a thickness of 3 mm and an inner diameter of 25 mm. The cured body was placed on the support ring. Steel balls were dropped onto the cured body from a height of 1.27 m using a drop device equipped with an electromagnet. The weights of the steel balls were 4.5 g, 6.9 g, 14 g, 16 g, 32 g, 50 g, 67 g, 80 g, 95 g, 112 g, 130 g, 151 g, 174 g, 198 g, 225 g, and 261 g. The steel balls were dropped in order from lightest to lightest, and the weight of the steel ball just before cracks or fractures occurred in the cured body was recorded as the maximum impact resistance. This test was performed three times, and the average value was recorded as the maximum impact resistance of the cured body. The results are shown in Table 1.

[0215] [Shore D Hardness Measurement] The Shore D hardness of the cured product was measured in accordance with JIS K 7215. The equipment used was a digital durometer (DD4, manufactured by Kobunshi Keiki Co., Ltd.) attached to a motor-driven constant pressure loader (CLE-150, manufactured by Kobunshi Keiki Co., Ltd.), and the needle was lowered at a rate of 1 cm / sec to read the value. Three measurements were taken, and the average value was used as the Shore D hardness of the cured product. The results are shown in Table 1.

[0216] [Refrigerated storage test] The cured product was left to stand in a 4°C thermostatic chamber for 30 minutes. Thereafter, the cured product was removed from the thermostatic chamber into a room at 25°C, and the surface of the cured product was visually inspected for clouding or not, and evaluated using the following three-point scale. The results are shown in Table 1. - Evaluation criteria - 1: No clouding was observed. 2: Clouding was observed on part of the surface of the cured product after removal, but the clouding disappeared after a few seconds. 3: Clouding was observed on the entire surface of the cured product after removal, and the clouding did not disappear even after leaving it to stand for 1 minute.

[0217] [Haze Disappearance Test] A haze disappearance test of the cured body was performed as follows. First, a steam generator was prepared. The steam generator included a water tank, a tank located within the water tank for storing water, a first pipe connecting the air (external atmosphere) to the water in the tank (aqueous phase), and a second pipe connecting the upper part of the water stored in the tank (gas phase) to the air (external atmosphere). Air was blown into the 50°C distilled water stored in the tank through the first pipe at a flow rate of 1.0 mL / min to generate steam within the tank. This steam was then discharged into the air through the second pipe. The cured body was placed 1 cm away from the steam outlet and exposed to steam for 1 second. After 1 second, the steam outlet was blocked, and the time until the haze of the cured body disappeared was measured. This test was performed 10 times, and the average value was taken as the haze disappearance time of the cured body. The results are shown in Table 1.

[0218]

[0219] As shown in Table 1, the curable compositions of Examples 1 to 12, which contained a first bismuth compound and a first radically polymerizable monomer in which the proportion of polyethylene glycol chains (EO ratio) was 75% or more and 95% or less, and in which the proportion of polyethylene glycol chains in the composition (EO amount) was 13.5 mass% or more, enabled the production of cured products with anti-fogging properties.

[0220] Preferred embodiments are described below. [1] A curable composition comprising: a first bismuth compound having bismuth and at least one of an acryloyl group and a methacryloyl group; and a first radically polymerizable monomer having a polyethylene glycol chain, wherein the ratio N2 / N1 of the number average molecular weight N2 of the polyethylene glycol chain to the number average molecular weight N1 is 75% or more and 95% or less, wherein the proportion of the polyethylene glycol chain is 13.5% by mass or more. [2] The curable composition according to [1], wherein the ratio N2 / N1 is 85% or more and 95% or less. [3] The curable composition according to [1] or [2], wherein the number average molecular weight N1 of the first radically polymerizable monomer is 500 or more and 1500 or less. [4] The curable composition according to any of [1] to [3], wherein the proportion of the first radically polymerizable monomer is 15% by mass or more. [5] The curable composition according to any one of [1] to [4], wherein the first radical polymerizable monomer is a monofunctional (meth)acrylate. [6] The curable composition according to any one of [1] to [5], wherein the first radical polymerizable monomer comprises a (meth)acrylate represented by the following formula (I): In the formula (I), R １ is a hydrogen atom or a methyl group, R ２ is an acryloyl group, a methacryloyl group, a methyl group, or a phenyl group, and n is an integer of 10 or more and 30 or less. [7] The curable composition according to any one of [1] to [6], wherein the proportion of the first bismuth compound is 30% by mass or more and 70% by mass or less. [8] The curable composition according to any one of [1] to [7], further containing a second radical polymerizable monomer having no polyethylene glycol chain. [9] The curable composition according to [8], wherein the second radical polymerizable monomer contains a compound represented by the following formula (II): In the formula (II), R ３ is a hydrogen atom or a methyl group, R ４ is an alkylene group having 1 to 5 carbon atoms, ５is an alkyl group having from 1 to 5 carbon atoms, a phenyl group, a dimethylamino group, a diethylamino group, an acryloyloxy group, or a methacryloyloxy group, and m is 0 or 1.

[10] The curable composition according to [8] or [9], wherein the proportion of the second radical polymerizable monomer is from 10% by mass to 40% by mass.

[11] The curable composition according to any one of [1] to

[10] , wherein the proportion of the polyethylene glycol chain is from 13.6% by mass to 30.0% by mass.

[0221]

[12] A cured product of the curable composition according to any one of [1] to

[11] .

[13] An optical article comprising the cured product according to

[12] .

[14] A lens comprising the cured product according to

[12] .

[15] A rubber sheet comprising the cured product according to

[12] .

[16] Eye protection equipment comprising the cured product according to

[12] .

[17] An antibacterial / antiviral agent comprising the cured product according to

[12] .

[18] A resin composition comprising bismuth, a (meth)acrylic resin, and 16.0% by mass or more of polyethylene glycol chains.

Claims

1. A curable composition comprising: a first bismuth compound having bismuth and at least one of an acryloyl group and a methacryloyl group; and a first radical polymerizable monomer having a polyethylene glycol chain, in which the ratio N2 / N1 of the number average molecular weight N2 of the polyethylene glycol chain to the number average molecular weight N1 is 75% or more and 95% or less, wherein the ratio of the polyethylene glycol chain is 13.5 mass% or more.

2. The curable composition according to claim 1, wherein the ratio N2 / N1 is 85% or more and 95% or less.

3. The curable composition according to claim 1, wherein the number average molecular weight N1 of the first radically polymerizable monomer is 500 or more and 1,500 or less.

4. The curable composition according to claim 1, wherein the proportion of the first radically polymerizable monomer is 15 mass % or more.

5. The curable composition according to claim 1, wherein the first radically polymerizable monomer is a monofunctional (meth)acrylate.

6. The curable composition according to claim 1, wherein the first radically polymerizable monomer comprises a (meth)acrylate represented by the following formula (I): In the formula (I), R １ is a hydrogen atom or a methyl group, R ２ represents an acryloyl group, a methacryloyl group, a methyl group, or a phenyl group; and n is an integer of 10 or more and 30 or less.

7. The curable composition according to claim 1, wherein the proportion of the first bismuth compound is 30% by mass or more and 70% by mass or less.

8. The curable composition according to claim 1, further comprising a second radically polymerizable monomer having no polyethylene glycol chain.

9. The curable composition according to claim 8, wherein the second radical polymerizable monomer comprises a compound represented by the following formula (II): In the formula (II), R ３ is a hydrogen atom or a methyl group, R ４ is an alkylene group having 1 to 5 carbon atoms; R ５ represents an alkyl group having 1 to 5 carbon atoms, a phenyl group, a dimethylamino group, a diethylamino group, an acryloyloxy group, or a methacryloyloxy group; and m is 0 or 1.

10. The curable composition described in claim 8, wherein the proportion of the second radically polymerizable monomer is 10% by mass or more and 40% by mass or less.

11. The curable composition according to claim 1, wherein the proportion of the polyethylene glycol chains is 13.6% by mass or more and 30.0% by mass or less.

12. A cured product of the curable composition according to any one of claims 1 to 11.

13. An optical article comprising the cured product according to claim 12.

14. A lens comprising the cured product according to claim 12.

15. A rubber sheet comprising the cured product according to claim 12.

16. An eye protection device comprising the cured product according to claim 12.

17. An antibacterial / antiviral agent comprising the cured product according to claim 12.

18. A resin composition comprising bismuth, a (meth)acrylic resin, and 16.0% by mass or more of a polyethylene glycol chain.

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