Polymerizable composition, cured product, optical material, spectacle lens, compound, method for producing polymerizable composition, and resin

Abstract

A polymerizable composition according to the present disclosure comprises: at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound; a polythiol compound; and either a compound represented by general formula (1), or a reaction product of a compound represented by general formula (1) and a polyiso(thio)cyanate compound or a polyepisulfide compound. In general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number of 0-4, Rb is a monovalent group free of OH, SH, or NHR2, n2 is a number of 0-3, R1 is a divalent hydrocarbon group, X is OH, SH, or NHR2, and R2 is a hydrogen atom or a hydrocarbon group.

Description

Polymerizable composition, cured product, optical material, eyeglass lens, compound, method for producing polymerizable composition, and resin

[0001] The present disclosure relates to a polymerizable composition, a cured product, an optical material, an eyeglass lens, a compound, a method for producing a polymerizable composition, and a resin.

[0002] High-refractive index plastic materials are increasingly being used as optical materials such as eyeglass lenses because they are lighter and less likely to break than inorganic materials such as glass, can be dyed, etc. Examples of plastic materials for optical materials include acrylic resins, polycarbonates, thiourethane resins, episulfide resins, etc., and among these, thiourethane resins and episulfide resins are known as plastic materials that can achieve high refractive indexes (see, for example, JP 2019-15922 A).

[0003] Optical materials containing resins generally contain ultraviolet absorbers (UVAs) to prevent degradation due to ultraviolet rays. UV absorbers may leach out of resins depending on the usage environment. Many compounds commonly used as UV absorbers are persistent and have concerns about their accumulation in living organisms, making them increasingly subject to environmental regulations in recent years. Therefore, measures to suppress the release of UV absorbers from resins have been investigated. In light of the above, one aspect of the present disclosure aims to provide a polymerizable composition that can yield a resin with suppressed UV absorber release, a method for producing the same, and a cured product, optical material, and eyeglass lens obtained using the polymerizable composition. Another aspect of the present disclosure aims to provide a compound that can yield a resin with suppressed UV absorber release, and a resin with suppressed UV absorber release.

[0004] Means for solving the above problems include the following aspects: <1> A polymerizable composition comprising at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound, a polythiol compound, and a compound represented by the following general formula (1) or a reaction product of a compound represented by the following general formula (1) with a polyiso(thio)cyanate compound or a polyepisulfide compound: (In the general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is OH, SH, or NHR ２ and R ２represents a hydrogen atom or a hydrocarbon group.) <2> The polymerizable composition according to claim 1, wherein the polyiso(thio)cyanate compound comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate. <3> The polythiol compound is 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl) The polymerizable composition according to <1> or <2>, comprising at least one selected from the group consisting of 1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane. <4> A cured product of the polymerizable composition according to any one of <1> to <3>. <5> An optical material comprising the cured product according to <4>. <6> An eyeglass lens comprising the optical material according to <5>. <7> A compound represented by the following general formula (1): (In the general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is OH, SH, or NHR ２ and R ２ represents a hydrogen atom or a hydrocarbon group.) <8> A compound that is a reaction product of the compound according to <7> with a polyiso(thio)cyanate compound or an episulfide compound. <9> A compound having a structure represented by the following general formula (2) and an iso(thio)cyanate group: (In the general formula (2), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is O, S, or NR ２ and R ２ is a hydrogen atom or a hydrocarbon group, and * is a bonding position. <10> A compound having a structure represented by the following general formula (3) and an episulfide group: (In the general formula (3), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and R ２ represents a hydrogen atom or a hydrocarbon group, * represents a bonding position, and Y represents a hydrogen atom or a bonding position.) <11> A method for producing a polymerizable composition, the method comprising a step of mixing the compound according to any one of <7> to <10>, at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound, and a polythiol compound. <12> A resin having a structure represented by the following general formula (2) or (3): (In the general formula (2) or (3), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR.) ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is O, S, or NR ２ and R ２is a hydrogen atom or a hydrocarbon group, * is a bonding position, and Y is a hydrogen atom or a bonding position.

[0005] According to the present disclosure, there are provided a polymerizable composition that can yield a resin in which release of an ultraviolet absorber is suppressed, a method for producing the same, and a cured product, an optical material, and an eyeglass lens obtained using the polymerizable composition. According to the present disclosure, there are provided a compound that can yield a resin in which release of an ultraviolet absorber is suppressed, and a resin in which release of an ultraviolet absorber is suppressed.

[0006] In the present disclosure, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the lower and upper limits. In the present disclosure, when a composition contains multiple substances corresponding to each component, the amount of each component refers to the total amount of the multiple substances present in the composition, unless otherwise specified. In the numerical ranges described in stages in the present disclosure, the upper or lower limit described in one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit of that numerical range may be replaced with a value shown in the examples.

[0007] [Polymerizable Composition] One embodiment of the present disclosure is a polymerizable composition comprising: at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound; a polythiol compound; and a compound represented by the following general formula (1) or a reaction product of a compound represented by the following general formula (1) with a polyiso(thio)cyanate compound or a polyepisulfide compound:

[0008]

[0009] In the general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is OH, SH, or NHR ２ and R ２ is a hydrogen atom or a hydrocarbon group.

[0010] The polymerizable composition of the present disclosure contains, as polymerizable components, at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound (hereinafter also referred to as the first component), and a polythiol compound (hereinafter also referred to as the second component). A resin containing a thiourethane structure is obtained by reacting an iso(thio)cyanate group, which is a polymerizable functional group of the polyiso(thio)cyanate compound, with a thiol group, which is a polymerizable functional group of the polythiol compound. A resin containing a sulfide structure is obtained by reacting an episulfide group, which is a polymerizable functional group of the polyepisulfide compound, with a thiol group, which is a polymerizable functional group of the polythiol compound. The resin (thiourethane resin or episulfide resin) obtained by the polymerization reaction of the first component and the second component has a high refractive index and is suitable for use in applications requiring a high refractive index, such as optical materials.

[0011] (Reactive UVA) The polymerizable composition of the present disclosure contains, in addition to the first and second components, a compound represented by general formula (1) or a reaction product of a compound represented by general formula (1) with a polyiso(thio)cyanate compound or a polyepisulfide compound (hereinafter also referred to as reactive UVA). That is, the reactive UVA can be classified into three types: (1) a compound represented by general formula (1), (2) a reaction product of a compound represented by general formula (1) with a polyiso(thio)cyanate compound, and (3) a reaction product of a compound represented by general formula (1) with a polyepisulfide compound.

[0012] (1) The compound represented by the general formula (1) is a compound represented by X, which is OH, SH or NH. ２(i.e., a functional group that can react with the polymerizable functional group of the first component). (2) The reaction product of the compound represented by general formula (1) and the polyiso(thio)cyanate compound has, among the multiple iso(thio)cyanate groups contained in the polyiso(thio)cyanate compound, an iso(thio)cyanate group that has not reacted with the functional group represented by X in general formula (1). (3) The reaction product of the compound represented by general formula (1) and the polyepisulfide compound has, among the multiple episulfide groups contained in the polyepisulfide compound, an episulfide group that has not reacted with the functional group represented by X in general formula (1). That is, the three types of reactive UVAs described above have the property of reacting with either the first component or the second component contained in the polymerizable composition. Therefore, in the resin obtained from the polymerizable composition containing the reactive UVA, the molecule that functions as a UVA is bound to the polymer structure formed by the polymerization reaction of the polymerizable component. As a result, the release of the molecule that functions as a UVA out of the resin is suppressed.

[0013] The specific molecular structure of the compound represented by general formula (1) is not particularly limited as long as it exhibits properties as a UVA.

[0014] In general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom. Examples of the monovalent hydrocarbon group represented by Ra include alkyl groups having 1 to 3 carbon atoms. Examples of the halogen atom represented by Ra include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of ultraviolet absorption performance, Ra is preferably a halogen atom, and more preferably a chlorine atom or a bromine atom. n1 represents the number of Ra and is a number from 0 to 4. n1 is preferably 0 to 2, and more preferably 0 or 1. When the number of Ra is 2 or more, the two or more Ra may be the same or different.

[0015] In the general formula (1), Rb is OH, SH, or NHR. ２ is a monovalent group that does not contain OH, SH, or NHR represented by Rb. ２Examples of monovalent groups that do not contain a carbon atom include monovalent hydrocarbon groups, alkoxy groups, and monovalent groups containing an ester bond. Examples of monovalent hydrocarbon groups represented by Rb include alkyl groups having 1 to 10 carbon atoms. The alkyl group may be linear or branched and may have a substituent. An example of the substituent is a phenyl group. Examples of alkoxy groups represented by Rb include alkoxy groups consisting of an alkyl group having 1 to 10 carbon atoms and an oxygen atom. The alkyl group may be linear or branched and may have a substituent. An example of the substituent is a phenyl group. Examples of monovalent groups containing an ester bond represented by Rb include monovalent groups represented by -Rc-C(=O)ORd or -Rc-OC(=O)-Rd (preferably -Rc-C(=O)ORd). In the formula, Rc is an alkylene group having 1 to 10 carbon atoms, and Rd is an alkyl group having 1 to 10 carbon atoms. The alkylene group or alkyl group may be linear or branched and may have a substituent. An example of the substituent is a phenyl group.

[0016] From the viewpoint of solubility in the polymerizable composition, Rb is preferably a monovalent hydrocarbon group, and more preferably a hydrocarbon group of Sp3 (for example, a tert-butyl group). From the viewpoint of ultraviolet absorption performance, Rb is preferably an alkoxy group having 3 or more carbon atoms. n2 represents the number of Rb and is a number from 0 to 3. n2 is preferably 0 to 2, and more preferably 0 or 1. When the number of Rb is 2 or more, the two or more Rb may be the same or different.

[0017] R in general formula (1) １ is a divalent hydrocarbon group. １ Examples of the divalent hydrocarbon group represented by the formula (I) include an alkylene group or an aralkylene group having 1 to 10 carbon atoms. The alkylene group may be linear or branched, and may contain a cyclic structure. １ The position of may be any of the para position, meta position, or ortho position relative to the OH group.

[0018] In the general formula (1), X is OH, SH, or NHR. ２ and R ２is a hydrogen atom or a hydrocarbon group. When the functional group of the first component to be reacted with X is an isocyanate group, X is OH, SH, or NHR. ２ When the functional group of the first component to be reacted with X is an episulfide group, X is preferably SH.

[0019] The type of polyiso(thio)cyanate compound or polyepisulfide compound to be reacted with the compound represented by general formula (1) is not particularly limited, and may be selected from, for example, the polyiso(thio)cyanate compounds or polyepisulfide compounds described below.

[0020] Examples of reaction products between a compound represented by general formula (1) and a polyiso(thio)cyanate compound include compounds having a structure represented by the following general formula (2) and an iso(thio)cyanate group. Examples of reaction products between a compound represented by general formula (1) and a polyepisulfide compound include compounds having a structure represented by the following general formula (3) and an episulfide group.

[0021]

[0022] In the general formula (2) or (3), Ra, n1, Rb, n2 and R １ The definitions of Ra, n1, Rb, n2 and R in general formula (1) are １ X is O, S or NR ２ and R ２ is a hydrogen atom or a hydrocarbon group, * is a bonding position, and Y is a hydrogen atom or a bonding position.

[0023] The polymerizable composition may contain one or more types of reactive UVAs. That is, the polyiso(thio)cyanate compound or polyepisulfide compound reacted with the compound represented by general formula (1) may be one or two or more types, and the compound represented by general formula (1) reacted with the polyiso(thio)cyanate compound or polyepisulfide compound may be one or two or more types.

[0024] The polyiso(thio)cyanate compound or polyepisulfide compound to be reacted with the compound represented by general formula (1) may be the same as or different from the polyiso(thio)cyanate compound or polyepisulfide compound contained as a polymerizable component in the polymerizable composition. The polymerizable composition may contain, as the reactive UVA, either the compound represented by general formula (1) or the reaction product of the compound represented by general formula (1) and the first component, or both.

[0025] The amount of the compound represented by general formula (1) contained in the polymerizable composition is not particularly limited and can be selected depending on the application of the polymerizable composition, etc. From the viewpoint of obtaining sufficient ultraviolet absorption performance, the amount of the compound represented by general formula (1) is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, even more preferably 0.5 parts by mass or more, and particularly preferably 1.0 parts by mass or more, based on 100 parts by mass of the total mass of the polymerizable components. From the viewpoint of the hue of the resin, the amount of the compound represented by general formula (1) is preferably 5.0 parts by mass or less, more preferably 3.0 parts by mass or less, and even more preferably 2.0 parts by mass or less, based on 100 parts by mass of the total mass of the polymerizable components. The above "amount of the compound represented by general formula (1)" does not include the amount of the polyiso(thio)cyanate compound or polyepisulfide compound reacted with the compound represented by general formula (1).

[0026] (Polyiso(thio)cyanate Compound) In the present disclosure, a polyiso(thio)cyanate compound refers to a compound having two or more isocyanate groups or isothiocyanate groups in one molecule. The polymerizable composition may contain one type of polyiso(thio)cyanate compound or two or more types of polyiso(thio)cyanate compounds.

[0027] The polyiso(thio)cyanate compound may include a dimer, a trimer, or a prepolymer. Examples of these polyiso(thio)cyanate compounds include the compounds exemplified in WO 2011 / 055540.

[0028] Examples of the polyiso(thio)cyanate compound include an aliphatic polyiso(thio)cyanate compound, an alicyclic polyiso(thio)cyanate compound, an aromatic polyiso(thio)cyanate compound, a heterocyclic polyiso(thio)cyanate compound, etc. The polyiso(thio)cyanate compound contained in the composition may be one type or two or more types.

[0029] The alicyclic polyiso(thio)cyanate compound refers to a polyiso(thio)cyanate compound that contains an alicyclic structure and may contain a heterocyclic structure. The aromatic polyiso(thio)cyanate compound refers to a polyiso(thio)cyanate compound that contains an aromatic structure and may contain an alicyclic structure and a heterocyclic structure. The heterocyclic polyiso(thio)cyanate compound refers to a polyiso(thio)cyanate compound that contains a heterocyclic structure and does not contain an alicyclic structure or an aromatic structure.

[0030] The polyiso(thio)cyanate compound preferably includes at least one selected from the group consisting of an aliphatic polyiso(thio)cyanate compound, an alicyclic polyiso(thio)cyanate compound, an aromatic polyiso(thio)cyanate compound, and a heterocyclic polyiso(thio)cyanate compound.

[0031] The polyiso(thio)cyanate compound preferably includes at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, and phenylene diisocyanate; It is more preferable that the compound contains at least one selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, xylylene diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane, and it is even more preferable that the compound contains at least one selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and m-xylylene diisocyanate.

[0032] (Polyepisulfide Compound) In the present disclosure, a polyepisulfide compound means a compound having two or more episulfide groups in one molecule. The polyepisulfide compound contained in the polymerizable composition may be one type or two or more types. Specific examples of the polyepisulfide compound include compounds represented by the following formula:

[0033]

[0034] In the formula, Y represents a linear divalent hydrocarbon group having 1 to 4 carbon atoms, a branched divalent hydrocarbon group having 2 to 4 carbon atoms, a cyclic divalent hydrocarbon group having 3 to 6 carbon atoms, a 1,4-dithiane group, an arylene group, or an aralkylene group, m represents an integer of 0 to 2, and n represents an integer of 0 to 3. Y may contain a substituent or may be unsubstituted.

[0035] Y preferably represents a straight-chain divalent hydrocarbon group having 1 to 4 carbon atoms, a branched divalent hydrocarbon group having 2 to 4 carbon atoms, or a cyclic divalent hydrocarbon group having 3 to 6 carbon atoms, and more preferably represents a straight-chain divalent hydrocarbon group having 1 to 4 carbon atoms. m preferably represents 0 or 1, and more preferably represents 0. n preferably represents 0 or 1, and more preferably represents 1.

[0036] The polyepisulfide compound preferably contains at least one selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, and 2,5-bis(2,3-epithiopropylthiomethyl)-1,4-dithiane.

[0037] From the viewpoint of the refractive index of the cured product to be obtained, the polyepisulfide compound preferably has a refractive index at 20° C. of 1.60 to 1.80 for sodium D lines (that is, light with a wavelength of 589.3 nm).

[0038] (Polythiol Compound) In the present disclosure, a polythiol compound refers to a compound having two or more thiol groups in one molecule. The composition may contain one type of polythiol compound or two or more types of polythiol compounds.

[0039] Specific examples of the polythiol compound include the compounds exemplified in WO 2016 / 125736.

[0040] The polythiol compounds include 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,11-dimercaptopropionate, ... pentaerythritol tetrakis(2-mercaptoacetate), penta bis(mercaptomethylthio)-1,4-dithiane, bis(2-mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane, more preferably, the mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane is at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), and pentaerythritol tetrakis(2-mercaptoacetate); It is more preferable that the mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane contains at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and pentaerythritol tetrakis(3-mercaptopropionate).

[0041] From the viewpoint of the refractive index of the cured product to be obtained, the polythiol compound preferably has a refractive index at 20° C. of 1.60 to 1.80 for sodium D lines (that is, light with a wavelength of 589.3 nm).

[0042] (Other Components) The polymerizable composition may contain other components in addition to the polymerizable component and the reactive UVA. Examples of other components include a polymerization catalyst, an internal mold release agent, a resin modifier, a base generator, a chain extender, a crosslinking agent, a radical scavenger, a light stabilizer, an antioxidant, an oil-soluble dye, a filler, an adhesion improver, an antibacterial agent, an antistatic agent, a dye, a fluorescent brightener, a fluorescent pigment, and an inorganic pigment.

[0043] Specific examples of the polymerization catalyst include tertiary amine compounds, inorganic or organic acid salts of tertiary amine compounds, metal compounds, quaternary ammonium salts, and organic sulfonic acids.

[0044] Specific examples of the internal mold release agent include acidic phosphate esters. Examples of acidic phosphate esters include monophosphate esters and diphosphate esters, and these can be used alone or in combination of two or more.

[0045] Specific examples of the resin modifier include alcohol compounds, amine compounds, epoxy compounds, organic acids or anhydrides thereof, (meth)acrylate compounds, and olefin compounds.

[0046] When the polymerizable composition contains components other than the polymerizable component and the reactive UVA, the total content thereof may be 0.1 ppm by mass to 70% by mass, 1 ppm by mass to 30% by mass, 10 ppm by mass to 10% by mass, or 0.1% by mass to 5% by mass, relative to the total mass of the polymerizable composition.

[0047] [Cured Product] In one embodiment of the present disclosure, the cured product is a cured product of the polymerizable composition described above. In the cured product of the present disclosure, molecules functioning as UVA are bonded to a polymer structure formed by a polymerization reaction of a polymerizable component. Therefore, release of the component functioning as UVA to the outside is suppressed. Furthermore, the cured product of the present disclosure includes a polymer structure formed by a polymerization reaction of a polythiol compound with at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound as a polymerizable component, and therefore has a high refractive index and excellent transparency.

[0048] The cured product of the present disclosure can be obtained, for example, by heating the polymerizable composition at a temperature at which a polymerization reaction of the polymerizable component occurs. When the cured product of the present disclosure is photocurable, the cured product can be obtained by irradiating the polymerizable composition with light of a wavelength at which a polymerization reaction of the polymerizable component occurs. Heating and light irradiation may be performed in combination.

[0049] [Optical Material and Eyeglass Lens] One embodiment of the present disclosure is an optical material containing the cured product described above. Specific examples of optical materials include optical adhesives, coatings, optical waveguides, films, lenses, anti-reflection films, microlenses, microlens arrays, wafer-level lenses, imaging lenses for cameras (such as in-vehicle cameras, digital cameras, PC cameras, mobile phone cameras, and surveillance cameras), eyeglass lenses, light beam focusing lenses, light diffusing lenses, and camera flash lenses. One embodiment of the present disclosure is an eyeglass lens containing the optical material described above.

[0050] [Compound] One embodiment of the present disclosure is a compound represented by the following general formula (1), or a compound that is a reaction product of a compound represented by the general formula (1) with a polyiso(thio)cyanate compound or an episulfide compound:

[0051]

[0052] In the general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １is a divalent hydrocarbon group, and X is OH, SH, or NHR ２ and R ２ is a hydrogen atom or a hydrocarbon group.

[0053] One embodiment of the present disclosure is a compound having a structure represented by the following general formula (2) and an iso(thio)cyanate group.

[0054]

[0055] In the general formula (2), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is O, S, or NR ２ and R ２ is a hydrogen atom or a hydrocarbon group, and * is a bonding position.

[0056] One embodiment of the present disclosure is a compound having a structure represented by general formula (3) and an episulfide group.

[0057]

[0058] In the general formula (3), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and R ２ is a hydrogen atom or a hydrocarbon group, * is a bonding position, and Y is a hydrogen atom or a bonding position.

[0059] The compound of the present disclosure is suitably used for producing a resin obtained by curing a polymerizable component or an article containing the same. For details and preferred embodiments of the compound of the present disclosure, reference can be made to the details and preferred embodiments of the reactive UVA contained in the polymerizable composition described above.

[0060] [Method for Producing Polymerizable Composition] One embodiment of the present disclosure is a method for producing a polymerizable composition, including a step of mixing the compound (reactive UVA) of the present disclosure described above, at least one compound selected from a polyiso(thio)cyanate compound and a polyepisulfide compound (first component), and a polythiol compound (second component).

[0061] According to the above method, a cured product in which UVA emission is suppressed can be produced. Details and preferred embodiments of each compound used in the method of the present disclosure are the same as those of each compound described above.

[0062] In the above method, the reactive UVA, the first component, and the second component may be mixed in one step or two steps. For example, the reactive UVA and the first component may be mixed, and then the second component may be mixed therewith. When a compound represented by general formula (1) is used as the reactive UVA, after mixing the compound represented by general formula (1) and the first component, all or part of the compound represented by general formula (1) may react with the first component to form a reaction product.

[0063] [Resin] One embodiment of the present disclosure is a resin having a structure represented by the following general formula (2) or general formula (3).

[0064]

[0065] In the general formula (2) or (3), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is O, S, or NR ２ and R ２ is a hydrogen atom or a hydrocarbon group, * is a bonding position, and Y is a hydrogen atom or a bonding position.

[0066] In the resin of the present disclosure, molecules that function as UVA are bound to the polymer structure, and therefore UVA emission is suppressed compared to when molecules that function as UVA are not bound to the polymer structure.

[0067] The type of resin of the present disclosure is not particularly limited. From the viewpoint of obtaining a high refractive index, the resin of the present disclosure preferably contains at least one selected from a thiourethane structure and a sulfide structure.

[0068] The present disclosure will be described in detail below with reference to examples. However, the present disclosure is not limited to the descriptions in these examples. Unless otherwise specified, "parts" are based on mass. Hereinafter, "room temperature" means 25°C unless otherwise specified.

[0069] <Reactive UVA Synthesis Example 1> 1.2 g (0.031 mol) of lithium aluminum hydride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 30 mL of dehydrated tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were placed in a 100 mL recovery flask. Next, 5.0 g (0.013 mol) of a compound represented by the following structural formula (EVERSORB88, manufactured by Everlight Chemical Co., Ltd.) was added, and the mixture was stirred at 0°C for 2 hours.

[0070]

[0071] After the reaction was completed, 1.2 g of water, 1.2 g of a 15% by weight aqueous sodium hydroxide solution, and 3.6 g of water were added sequentially, and the reaction solution was then filtered under reduced pressure. To the resulting solution, 100 mL of dichloromethane (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added, followed by 20.0 g of a 35% by weight aqueous hydrochloric acid solution, followed by 15 minutes of washing. Next, 10.0 g of water, 20.0 g of saturated aqueous sodium carbonate solution, and 10.0 g of water were added sequentially for 15 minutes of washing. Then, 10.0 g of anhydrous sodium sulfate was added to the resulting organic phase, followed by dehydration, and the residue was removed by gravity filtration. The organic solvent was then distilled off under heating and reduced pressure, followed by drying under reduced pressure, yielding 3.5 g (75% yield) of a compound having a terminal hydroxyl group (UVA-OH, structure shown below) as an orange solid. High-performance liquid chromatography analysis of this solid confirmed that the peak at 24.5 minutes (raw material used) disappeared, and a new peak at 14.1 minutes (UVA-OH) appeared.

[0072]

[0073] <Reactive UVA Synthesis Example 2> 2.5 g (0.029 mol) of 2-(2H-benzo[d][1,2,3]triazol-2-yl)-4-(2-hydroxyethyl)phenol (manufactured by BLD Pharmatech), 50 mL of dehydrated tetrahydrofuran, 3.0 g (0.029 mol) of triethylamine (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), and 3.4 g (0.029 mol) of methanesulfonyl chloride (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were sequentially added to a 100 mL recovery flask and stirred at 0°C for 1 hour. After completion of the reaction, 55.0 g of a 1% by mass aqueous hydrochloric acid solution was added and washed for 15 minutes. Next, the mixture was washed sequentially with 55.0 g of water, 55.0 g of a saturated aqueous sodium carbonate solution, and 110.0 g of water for 15 minutes, and then 10.0 g of anhydrous sodium sulfate was added to the resulting organic phase to dehydrate it, and the residue was removed by gravity filtration. The organic solvent was then removed by distillation under reduced pressure with heating, followed by drying under reduced pressure to obtain 9.8 g (yield 99%) of a white solid compound having a terminal mesyl group (structure shown below). It was confirmed that the peak at 3.6 minutes (starting material) disappeared and a new peak at 4.4 minutes (mesyl-substituted product) appeared when measuring this solid by high performance liquid chromatography.

[0074]

[0075] 5.0 g (0.015 mol) of a compound having a terminal mesyl group, 120 mL of dioxane (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 1.7 g (0.225 mol) of thiourea were added to a 200 mL recovery flask, heated to 100 ° C, and stirred for 3 hours. The temperature was then lowered to 60 ° C, and 2.3 g (0.034 mol) of 25 wt% aqueous ammonia solution (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added, followed by heating and stirring for 3 hours. The mixture was then allowed to cool to room temperature, and 100 mL of dichloromethane and 50.0 g of 35 wt% aqueous hydrochloric acid solution were added and washed for 15 minutes. Next, 100.0 g of water was added and washed three times for 15 minutes. Then, 10.0 g of anhydrous sodium sulfate was added to the resulting organic phase to dehydrate it, and the residue was removed by gravity filtration. The organic solvent was then removed by distillation under heating and reduced pressure, followed by drying under reduced pressure to obtain 3.1 g (75% yield) of a white solid compound having a terminal mercapto group (UVA-SH, structure shown below). It was confirmed that the peak at 4.4 minutes disappeared and a new peak (UVA-SH) at 7.4 minutes appeared in the measurement of this solid by high performance liquid chromatography.

[0076]

[0077] Comparative Example 1 7.8 parts by mass of m-xylylene diisocyanate (manufactured by Mitsui Chemicals, Inc.) as a polyisocyanate compound, 0.0023 parts by mass of dibutyltin dichloride as a curing catalyst, 0.015 parts by mass of an acidic phosphate ester (Zelec UN, manufactured by Stepan) as an internal mold release agent, and 0.23 parts by mass of a compound having the following structure (Biosorb 583, manufactured by Kyodo Pharmaceutical Co., Ltd.) as an ultraviolet absorber were mixed and dissolved at 20° C. and stirred for 30 minutes. 7.2 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (manufactured by Mitsui Chemicals, Inc.) as a polythiol compound were mixed thereto to obtain a homogeneous liquid, which was a polymerizable composition for producing a resin molded body.

[0078]

[0079] The obtained polymerizable composition was degassed at 600 Pa for 1 hour and then filtered through a 1 μm Teflon (registered trademark) filter. The filtered polymerizable composition was poured into a mold consisting of a pair of glass plates secured with tape. This mold was placed in an oven, and the temperature inside the oven was raised from 10° C. to 120° C. over 38 hours to cure the polymerizable composition. The cured product removed from the mold was annealed at 120° C. for 2 hours to obtain a flat-plate-shaped resin molded product with a thickness of 3.0 mm.

[0080] Comparative Example 2 Polymerization was carried out in the same manner as in Comparative Example 1, except that the polyisocyanate compound was changed to 7.6 parts by mass of a mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2,2,1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2,2,1]-heptane (manufactured by Mitsui Chemicals, Inc.), the amount of dibutyltin dichloride was changed from 0.0023 parts by mass to 0.009 parts by mass, the amount of internal mold release agent was changed from 0.015 parts by mass to 0.018 parts by mass, and the polythiol compound was changed to 3.8 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 3.6 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) (manufactured by Mitsui Chemicals, Inc.), and a 3.0 mm-thick flat-plate-shaped resin molded product was obtained.

[0081] Comparative Example 3 Polymerization was carried out in the same manner as in Comparative Example 1, except that the amount of m-xylylene diisocyanate was changed from 7.8 parts by mass to 7.6 parts by mass, and the polythiol compound was changed to 7.4 parts by mass of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (manufactured by Mitsui Chemicals, Inc.), to obtain a flat-plate-shaped resin molded product having a thickness of 3.0 mm.

[0082] Comparative Example 4: 10.0 parts by mass of bis(2,3-epithiopropyl)disulfide (manufactured by Mitsui Chemicals, Inc.), 0.002 parts by mass of N,N-dimethylcyclohexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.01 parts by mass of N,N-dicyclohexylmethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) as polyepisulfide compounds; 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as a polythiol compound; A polymerizable composition for producing a resin molded product was obtained by mixing 0.99 parts by mass of a mixture of 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (manufactured by Mitsui Chemicals, Inc.) and 0.11 parts by mass of a compound having the following structure (Tinuvin PS, manufactured by BASF Japan Ltd.) as an ultraviolet absorber, to form a homogeneous liquid.

[0083]

[0084] The obtained polymerizable composition was degassed at 600 Pa for 1 hour and then filtered through a 1 μm Teflon (registered trademark) filter. The filtered polymerizable composition was poured into a mold consisting of a pair of glass plates secured with tape. This mold was placed in an oven, and the temperature inside the oven was raised from 10° C. to 120° C. over 20 hours to cure the polymerizable composition. The cured product removed from the mold was annealed at 120° C. for 2 hours to obtain a flat-plate-shaped resin molded product having a thickness of 3.0 mm.

[0085] Example 1 Polymerization was carried out in the same manner as in Comparative Example 1, except that the ultraviolet absorber was changed to 0.075 parts by mass of UVA-OH, to obtain a flat resin molded product having a thickness of 3.0 mm. Before the polymerizable composition was poured into a mold, it was measured by FT-IR (using an IR Spirit manufactured by Shimadzu Corporation; the same applies hereinafter) to confirm the formation of urethane bonds (1600-1750 cm －１ (A new peak appeared at the peak.) From this result, it was confirmed that a reaction product between UVA-OH and the polyisocyanate compound was produced in the polymerizable composition.

[0086] Example 2 Polymerization was carried out in the same manner as in Comparative Example 2, except that the ultraviolet absorber was changed to 0.15 parts by mass of UVA-OH, to obtain a flat resin molded product having a thickness of 3.0 mm. Before the polymerizable composition was poured into a mold, FT-IR measurement was carried out to confirm the formation of urethane bonds (1600-1750 cm －１ (A new peak appeared at the peak.) From this result, it was confirmed that a reaction product between UVA-OH and the polyisocyanate compound was produced in the polymerizable composition.

[0087] Example 3 Polymerization was carried out in the same manner as in Comparative Example 3, except that the ultraviolet absorber was changed to 0.075 parts by mass of UVA-OH, to obtain a flat-plate-shaped resin molded product having a thickness of 3.0 mm. Before the polymerizable composition was poured into a mold, FT-IR measurement was carried out to confirm the formation of urethane bonds (1600-1750 cm －１ (A new peak appears in the figure.)

[0088] Example 4 Polymerization was carried out in the same manner as in Comparative Example 1, except that the ultraviolet absorber was changed to 0.20 parts by mass of UVA-SH, to obtain a resin molded body in the form of a flat plate having a thickness of 3.0 mm. Before the polymerizable composition was poured into the mold, FT-IR measurement was carried out to confirm the formation of a thiourethane bond (1600-1750 cm －１ (A new peak appeared at the peak.) From this result, it was confirmed that a reaction product between UVA-SH and the polyisocyanate compound was produced in the polymerizable composition.

[0089] Example 5 Polymerization was carried out in the same manner as in Comparative Example 2, except that the ultraviolet absorber was changed to 0.20 parts by mass of UVA-SH, to obtain a flat resin molded product having a thickness of 3.0 mm. Before the polymerizable composition was poured into a mold, FT-IR measurement was carried out to confirm the formation of a thiourethane bond (1600-1750 cm －１ (A new peak appeared at the peak.) From this result, it was confirmed that a reaction product between UVA-SH and the polyisocyanate compound was produced in the polymerizable composition.

[0090] Example 6 Polymerization was carried out in the same manner as in Comparative Example 3, except that the ultraviolet absorber was changed to 0.20 parts by mass of UVA-SH, to obtain a flat-plate-shaped resin molded product having a thickness of 3.0 mm. Before the polymerizable composition was poured into a mold, FT-IR measurement was carried out to confirm the formation of a thiourethane bond (1600-1750 cm －１ (A new peak appeared at the peak.) From this result, it was confirmed that a reaction product between UVA-SH and the polyisocyanate compound was produced in the polymerizable composition.

[0091] Example 7 Polymerization was carried out in the same manner as in Comparative Example 4, except that the ultraviolet absorber was changed to 0.11 parts by mass of UVA-SH, to obtain a 3.0 mm thick flat plate-shaped resin molded product. The annealed resin molded product was measured by FT-IR, and the peak of the mercapto group (2400-2600 cm －１ From this result, it was confirmed that UVA-SH and the polyepisulfide compound had reacted in the resin molded product.

[0092] <Evaluation of UVA UV Absorption Performance> A mixture of 5.0 mg of the UV absorber used in the Examples and Comparative Examples and 10 mL of chloroform was prepared, and the UV-visible absorption spectrum was measured from 300 nm to 800 nm using a UV-vis spectrophotometer (UV-1800, manufactured by Shimadzu Corporation). The transmittance (%) at 380 nm and 400 nm is shown in Table 1.

[0093]

[0094] As shown in Table 1, UVA-OH and UVA-SH obtained in Synthesis Examples 1 and 2 both had low light transmittance in the ultraviolet region (particularly at 380 nm), demonstrating their performance as ultraviolet absorbers.

[0095] <Evaluation of UV absorption performance of resin molded articles> The UV-visible absorption spectra of the resin molded articles prepared in the examples and comparative examples were measured from 300 nm to 800 nm using a UV-vis spectrophotometer (UV-1800, manufactured by Shimadzu Corporation). The transmittance (%) at 380 nm, 400 nm, and 420 nm is shown in Table 2.

[0096] <Evaluation of UV Absorber Leaching> The leaching of UV absorbers from the resin molded articles produced in the Examples and Comparative Examples was evaluated by the following test. The resin molded articles were pulverized by freeze-pulverization to obtain resin powder. Five grams of the obtained resin powder was subjected to ultrasonic extraction twice (10 minutes each) at 25°C using 35 mL of dichloromethane. Dichloromethane was removed from the obtained dichloromethane extract using a rotary evaporator. The amount of the concentrate obtained after solvent removal was designated as the amount of eluted component X (mg). The recovery rate (wt%) of the eluted component was calculated using the following formula based on the theoretical amount of UVA Y (mg) contained in 5 g of the resin powder used and the amount of eluted component X (mg). The results are shown in Table 1. Recovery rate (wt%) of eluted component = (X / Y) × 100

[0097] 100 mg of the eluted component obtained by the above method was dissolved in 10 mL of chloroform, and the UV-visible absorption spectrum was measured. If the transmittance at 370 nm was 90% or higher, it was determined that the eluted component did not contain sufficient absorbent components at that wavelength, and the content of the benzotriazole skeleton in the eluted component was determined to be sufficiently low (1% or less). The results are shown in Table 1. For the calibration curve, the amounts of UV absorber (Viosorb-583) shown in (1) to (3) below were dissolved in 10 mL of chloroform, and the UV-visible absorption spectrum was measured. The results are shown below. (1) Transmittance (T%) of 5.0 mg (approximately 500 ppm reproduced) = 0.03% (2) Transmittance (T%) of 0.5 mg (approximately 50 ppm reproduced) = 20.5% (3) Transmittance (T%) of 0.05 mg (approximately 5 ppm reproduced) = 91.2%

[0098]

[0099] As shown in Table 2, the resin molded articles obtained in Examples 1 to 7 all had low light transmittance in the ultraviolet region and exhibited sufficient ultraviolet absorption ability. Furthermore, the resin molded articles obtained in Examples 1 to 7 had a higher transmittance T% of the eluted components at 370 nm (90% or higher) and a lower content of benzotriazole skeletons in the eluted components (1% or lower) compared to the resin molded articles obtained in Comparative Examples 1 to 4. These results demonstrate that the elution of the ultraviolet absorber in the resin molded articles obtained in Examples 1 to 7 was suppressed. This is thought to be because the ultraviolet absorber was bonded to the polymer structure in the resin molded articles obtained in Examples 1 to 7.

[0100] The disclosure of Japanese Patent Application No. 2023-113708 is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards mentioned herein are incorporated by reference into this specification to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A polymerizable composition comprising: at least one selected from a polyiso(thio)cyanate compound and a polyepisulfide compound; a polythiol compound; and a compound represented by the following general formula (1) or a reaction product of a compound represented by the following general formula (1) with a polyiso(thio)cyanate compound or a polyepisulfide compound: In the general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is OH, SH, or NHR. ２ and R ２ is a hydrogen atom or a hydrocarbon group.

2. The polymerizable composition of claim 1, wherein the polyiso(thio)cyanate compound comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate.

3. The polythiol compound is 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl) 2. The polymerizable composition according to claim 1, comprising at least one selected from the group consisting of bis(mercaptomethylthio)ethyl)-1,4-dithiane, bis(2-mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane.

4. A cured product of the polymerizable composition according to claim 1.

5. An optical material comprising the cured product according to claim 4.

6. A spectacle lens comprising the optical material according to claim 5.

7. A compound represented by the following general formula (1): In the general formula (1), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is OH, SH, or NHR. ２ and R ２ is a hydrogen atom or a hydrocarbon group.

8. A compound which is the reaction product of the compound according to claim 7 with a polyiso(thio)cyanate compound or an episulfide compound.

9. A compound having a structure represented by the following general formula (2) and an iso(thio)cyanate group. In the general formula (2), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is O, S, or NR ２ and R ２ is a hydrogen atom or a hydrocarbon group, and * is a bonding position.

10. A compound having a structure represented by the following general formula (3) and an episulfide group: In the general formula (3), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, R ２ is a hydrogen atom or a hydrocarbon group, * is a bonding position, and Y is a hydrogen atom or a bonding position.

11. A method for producing a polymerizable composition, comprising a step of mixing the compound according to any one of claims 7 to 10, at least one compound selected from the group consisting of a polyiso(thio)cyanate compound and a polyepisulfide compound, and a polythiol compound.

12. A resin having a structure represented by the following general formula (2) or general formula (3): (In the general formula (2) or (3), Ra is a monovalent hydrocarbon group or a halogen atom, n1 is a number from 0 to 4, and Rb is OH, SH, or NHR. ２ n2 is a number from 0 to 3, and R １ is a divalent hydrocarbon group, and X is O, S, or NR ２ and R ２ is a hydrogen atom or a hydrocarbon group, * is a bonding position, and Y is a hydrogen atom or a bonding position.

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