Polymerizable compositions, resins, molded articles, optical materials, and lenses

Abstract

This polymerizable composition comprises: an episulfide compound represented by formula (1); a polyiso(thio)cyanate compound; a polythiol compound; and an epoxy compound (X) that includes one or more epoxy groups per molecule and that does not include an episulfide group. In formula (1), Y represents a substituted or unsubstituted linear hydrocarbon group having 1-4 carbon atoms; a substituted or unsubstituted branched hydrocarbon group having 2-4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3-6 carbon atoms, a substituted or unsubstituted 1,4-dithiane group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group, m represents an integer of 0-2, and n represents an integer of 0-3.

Description

[Technical Field] 【0001】 This disclosure relates to polymerizable compositions, resins, molded articles, optical materials, and lenses. [Background technology] 【0002】 Plastic lenses are lighter, less prone to breakage, and can be dyed compared to inorganic lenses, and have therefore become rapidly popular in recent years for applications such as eyeglass lenses and camera lenses. 【0003】 In recent years, various studies have been conducted on resin compositions containing episulfide compounds as raw materials for plastic lenses. For example, Patent Document 1 discloses a resin composition comprising a compound having a specific thiirane ring (i.e., a specific episulfide compound), a compound having one or more epoxy groups in one molecule, and a polymerization catalyst, with the objective of developing a method for adjusting the polymerization rate and improving the heat resistance of a resin optical material having a sufficiently high refractive index and a good Abbe number. 【0004】 Patent Document 1: Japanese Unexamined Patent Publication No. 2005-298742 [Overview of the project] [Problems that the invention aims to solve] 【0005】 However, there are cases where it is necessary to further improve the strength of resins obtained from resin compositions containing episulfide compounds (hereinafter also referred to as "polymerizable compositions") while maintaining a high refractive index. An object of one aspect of this disclosure is to provide a polymerizable composition capable of producing a resin with a high refractive index and excellent strength, as well as a resin, molded article, optical material, and lens with a high refractive index and excellent strength. [Means for solving the problem] 【0006】 The means for solving the above problems include the following embodiments. <1> An episulfide compound represented by the following formula (1), a polyisothiocyanate compound, a polythiol compound, an epoxy compound (X) containing one or more epoxy groups in one molecule and not containing an episulfide group, and a polymerizable composition containing the same. 【0007】 [Chemical formula] 【0008】 In formula (1), Y represents a substituted or unsubstituted linear hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted branched hydrocarbon group having 2 to 4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3 to 6 carbon atoms, a substituted or unsubstituted 1,4-dithiane group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group, and m represents an integer of 0 to 2 , and n represents an integer of 0 to 3. 【0009】 <2> The polymerizable composition according to <1>, wherein the epoxy compound (X) contains an epoxy compound (X1) containing two or more epoxy groups in one molecule. <3> Let the total number of moles of mercapto groups contained in the total amount of the polythiol compound be M S , Let the total number of moles of isothiocyanate groups in the total amount of the polyisothiocyanate compound be M N , Let the total number of moles of episulfide groups contained in the total amount of the episulfide compound represented by the formula (1) be M E . When (M S -M N ) / M E The ratio is more than zero and 0.2 or less, and the polymerizable composition according to <1> or <2>. <4> The polythiol compound contains at least one selected from the group consisting of 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, 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(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, and is the polymerizable composition according to any one of <1> to <3>. <5> The polyisothiocyanate compound contains 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 di isocyanate, and is the polymerizable composition according to any one of <1> to <4>. <6> Furthermore, the polymerizable composition according to any one of <1> to <5> contains a compound represented by the following formula (2). (R 1 )4Y + X - …(2) 〔In formula (2), the four Rs 1Each of these independently represents a straight-chain hydrocarbon group with 1 to 10 carbon atoms or a branched hydrocarbon group with 3 to 10 carbon atoms, X represents a halogen atom, and Y represents a nitrogen atom or a phosphorus atom. <7> Furthermore, it contains a tertiary amine compound. <1> ~ <6> A polymerizable composition as described in any one of the following. <8> Furthermore, the compound comprises at least one of the compound represented by the following formula (3) and the compound represented by the following formula (4), <7> The polymerizable composition described above. 【0010】 [ka] 【0011】 In formula (3), each of the m R1 atoms independently represents a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a halogen atom; Q represents a carbon atom, a nitrogen atom, or an oxygen atom; and m represents an integer from 0 to 5. In formula (4), R2, R3, and R4 each independently represent a linear alkyl group having 3 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an allyl group. R2 and R3 may be bonded to each other to form a ring. 【0012】 <9> The compound represented by formula (3) is at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chlorpyridine, 2-ethylpyridine, and 3-ethylpyridine. The compound represented by formula (4) is at least one selected from the group consisting of triallylamine and trioctylamine. <8> The polymerizable composition described above. <10> Furthermore, containing Lewis acid compounds, <1> ~ <9> A polymerizable composition as described in any one of the following. <11> The Lewis acid compound includes a compound represented by the following formula (5): <10> The polymerizable composition described above. 【0013】 [ka] 【0014】 In formula (5), R4 represents an alkyl group having 1 to 4 carbon atoms, X represents a fluorine atom, a chlorine atom, a bromine atom, or -OC(=O)-R5, R5 represents an alkyl group having 1 to 11 carbon atoms, and c represents an integer from 1 to 3. 【0015】 <12> The compound represented by formula (5) is at least one selected from the group consisting of dimethyltin dichloride, dibutyltin dichloride, and dibutyltin dilaurate. <11> The polymerizable composition described above. <13> <1> ~ <12> A resin which is a cured product of any one of the polymerizable compositions described in any one of the above. <14> <13> A molded article containing the resin described above. <15> <13> Optical materials containing the resin described above. <16> <13> Lenses containing the resin described above. [Effects of the Invention] 【0016】 According to one aspect of this disclosure, a polymerizable composition capable of producing a resin with a high refractive index and excellent strength, and In addition, resins, molded articles, optical materials, and lenses with high refractive index and excellent strength are provided. [Modes for carrying out the invention] 【0017】 In this disclosure, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. In this disclosure, the amount of each component in a composition means the total amount of any multiple substances present in the composition, unless otherwise specified, if there are multiple substances corresponding to each component in the composition. In numerical ranges described in stages within this disclosure, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in numerical ranges described within this disclosure, the upper or lower limit of that range may be replaced with the values ​​shown in the examples. 【0018】 [Polymerizable composition] The polymerizable compositions of this disclosure are The episulfide compound represented by formula (1) described below, Polyiso(thio)cyanate compounds and Polythiol compounds and An epoxy compound (X) containing one or more epoxy groups in one molecule and not containing an episulfide group, It contains. 【0019】 The polymerizable composition of this disclosure makes it possible to produce a resin with a high refractive index and excellent strength. Here, the high refractive index of the resin is thought to be due to the effect of the episulfide compound (1) represented by formula (1) described later. The strength of the resin is thought to be due to the effects of the polyiso(thio)cyanate compound, the polythiol compound, and the epoxy compound (X). 【0020】 The following describes the components that may be included in the polymerizable composition of this disclosure. 【0021】 <Episulfide compound represented by formula (1)> The polymerizable compositions of this disclosure contain at least one episulfide compound represented by the following formula (1). 【0022】 [ka] 【0023】 In formula (1), Y represents a substituted or unsubstituted linear hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted branched hydrocarbon group having 2 to 4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3 to 6 carbon atoms, a substituted or unsubstituted 1,4-dithiane group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group, m represents an integer from 0 to 2, and n represents an integer from 0 to 3. 【0024】 Y represents substituted or unsubstituted linear hydrocarbon groups having 1 to 4 carbon atoms and substituted or unsubstituted branched hydrocarbon groups having 2 to 4 carbon atoms, including methylene group, ethylene group, 1,2-propylene group, 1,3-propylene group, 1,2-butylene group, 1,3-butylene group, 1 Examples include unsubstituted alkylene groups such as ,4-butylene groups, and groups obtained by substituting the above unsubstituted alkylene groups with substituents such as alkyl groups, hydroxyl groups, mercapto groups, carbonyl groups, and thiocarbonyl groups. Examples of substituted or unsubstituted cyclic hydrocarbon groups having 3 to 6 carbon atoms represented by Y include unsubstituted cyclic alkylene groups such as cyclopropylene, 1,2-cyclobutylene, 1,3-cyclobutylene, 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene, and 1,4-cyclohexylene, as well as groups obtained by substituting the above unsubstituted cyclic alkylene groups with substituents such as alkyl groups, hydroxyl groups, mercapto groups, carbonyl groups, and thiocarbonyl groups. 【0025】 Examples of substituted or unsubstituted 1,4-dithiane groups represented by Y include the unsubstituted 1,4-dithiane group represented by the following formula, and the group obtained by substituting the above unsubstituted 1,4-dithiane group with substituents such as alkyl groups and hydroxyl groups. In the following equation, * represents the bond position. 【0026】 [ka] 【0027】 Examples of substituted or unsubstituted arylene groups represented by Y include unsubstituted arylene groups such as phenylene groups and naphthylene groups, and groups in which the above unsubstituted arylene groups are substituted with substituents such as alkyl groups, hydroxyl groups, mercapto groups, carbonyl groups, and thiocarbonyl groups. 【0028】 Examples of substituted or unsubstituted aralkylene groups represented by Y include unsubstituted aralkylene groups such as benzylene and phenethylene, and groups in which the above unsubstituted aralkylene groups are substituted with substituents such as alkyl groups, hydroxyl groups, mercapto groups, carbonyl groups, and thiocarbonyl groups. 【0029】 In equation (1), m represents an integer between 0 and 2. m is preferably 0 or 1, and more preferably 0. 【0030】 In equation (1), n ​​represents an integer between 0 and 3. n is preferably 0 or 1. 【0031】 For episulfide compounds represented by formula (1), refer to paragraphs 0025 to 0038 of Japanese Patent Publication No. 2005-272778 as appropriate. 【0032】 Preferably, the episulfide compound represented by formula (1) is: Bis(2,3-epithiopropyl) sulfide, Bis(2,3-epithiopropylthio)methane, Bis(2,3-epithiopropylthio)ethane, 3,8-bis(2,3-epithiopropylthio)-3,6-dithiaoctane, and It comprises at least one selected from the group consisting of bis(2,3-epithiopropyl) disulfides (hereinafter also referred to as "episulfide compound (E1)"), More preferably, the compound comprises at least one of bis(2,3-epithiopropyl) sulfide and bis(2,3-epithiopropyl) disulfide (hereinafter also referred to as "episulfide compound (E2)"). 【0033】 In the polymerizable composition, the proportion of the episulfide compound (E1) in the total amount of the episulfide compound represented by formula (1) is preferably 50% to 100% by mass, more preferably 60% to 100% by mass, and even more preferably 80% to 100% by mass. In polymerizable compositions, the preferred range for the proportion of episulfide compound (E2) in the total amount of episulfide compound represented by formula (1) is the same as the preferred range for the proportion of episulfide compound (E1) in the total amount of episulfide compound represented by formula (1). 【0034】 The content of the episulfide compound represented by formula (1) relative to the total amount of the polymerizable composition of this disclosure is preferably 30% by mass or more, and more preferably 40% by mass or more, from the viewpoint of superior refractive index of the resulting resin. The content of the episulfide compound represented by formula (1) relative to the total amount of the polymerizable composition of this disclosure is preferably 85% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less, from the viewpoint of further improving the strength and hue of the resulting resin. A preferred range for the content of the episulfide compound represented by formula (1) relative to the total amount of the polymerizable composition of this disclosure is, for example, 30% to 85% by mass. 【0035】 <Polyiso(thio)cyanate compounds> The polymerizable composition of this disclosure contains at least one polyiso(thio)cyanate compound. In this disclosure, a polyiso(thio)cyanate compound means a compound containing two or more iso(thio)cyanate groups in one molecule. In this disclosure, "iso(thio)cyanate group" means an isocyanate group or an isothiocyanate group. 【0036】 For polyiso(thio)cyanate compounds, refer to paragraphs 0049 to 0051 of Japanese Patent Publication No. 2005-272778 as appropriate. 【0037】 The polyiso(thio)cyanate compounds in the polymerizable compositions of this disclosure include 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, It is particularly preferable to include at least one selected from the group consisting of and phenylenediisocyanate (hereinafter referred to as "polyisocyanate compound N1"). 【0038】 In the polymerizable composition, the proportion of polyisocyanate compound N1 in the total amount of polyiso(thio)cyanate compounds is preferably 50% to 100% by mass, more preferably 60% to 100% by mass, and even more preferably 80% to 100% by mass. 【0039】 The content of the polyiso(thio)cyanate compound relative to the total amount of the polymerizable composition of this disclosure is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, from the viewpoint of further improving the Abbe number, hue, and strength of the resulting resin. The content of the polyiso(thio)cyanate compound in relation to the total amount of the polymerizable composition of this disclosure is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less, from the viewpoint of superior refractive index of the resulting resin. A preferred range for the content of the polyiso(thio)cyanate compound relative to the total amount of the polymerizable composition of this disclosure is, for example, in the range of 2% to 50% by mass. 【0040】 <Polythiol compounds> The polymerizable composition of this disclosure contains at least one polythiol compound. In this disclosure, a polythiol compound means a compound containing two or more mercapto groups (i.e., thiol groups) in one molecule. In this disclosure, two or more polythiol compounds may be referred to as a "polythiol composition." 【0041】 For information on polythiol compounds, refer to paragraphs 0039 to 0048 of Japanese Patent Publication No. 2005-272778 as appropriate. 【0042】 The polythiol compounds in the polymerizable compositions of this disclosure are 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, 2,5-bis(mercaptomethyl)-1,4-dithiane, and bis(mercaptoethyl)sulfide. Preferably, it contains at least one selected from the group consisting of 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiethane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane (hereinafter also referred to as "polythiol compound S1"). 【0043】 In the polymerizable composition, the proportion of polythiol compound S1 in the total amount of polythiol compounds (i.e., if polythiol compound S1 consists of two or more compounds, the proportion of the total content of these two or more compounds) is preferably 50% to 100% by mass, more preferably 60% to 100% by mass, and even more preferably 80% to 100% by mass. 【0044】 The content of the polythiol compound relative to the total amount of the polymerizable composition of this disclosure is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, from the viewpoint of further improving the hue and strength of the obtained resin. The content of the polythiol compound relative to the total amount of the polymerizable composition of this disclosure is preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less, from the viewpoint of superior refractive index and heat resistance of the resulting resin. A preferred range for the content of the polythiol compound relative to the total amount of the polymerizable composition of this disclosure is, for example, 5% to 60% by mass. 【0045】 <Epoxy compound (X)> The polymerizable composition of this disclosure contains at least one epoxy compound (X). In this disclosure, epoxy compound (X) is a compound that contains one or more epoxy groups in a single molecule and does not contain an episulfide group. 【0046】 The epoxy compound (X) preferably contains epoxy compound (X1). Here, epoxy compound (X1) is a compound containing two or more epoxy groups in one molecule (preferably two to four, more preferably two or three, and even more preferably two). The proportion of epoxy compound (X1) in the total amount of epoxy compound (X) is preferably 50% to 100% by mass, more preferably 60% to 100% by mass, and even more preferably 80% to 100% by mass. 【0047】 Examples of epoxy compounds (X) include: Phenolic epoxy compounds that are condensates of aromatic hydroxy compounds such as phenol, cresol, xylenol, naphthol, hydroquinone, catechol, resorcinol, bisphenol A, bisphenol F, bisphenol sulfone, bisphenol ether, bisphenol sulfide, bisphenol sulfide, halogenated bisphenol A novolac resin, and glycidol; Alcohol-based epoxy compounds that are condensates of alcohol compounds such as methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, iso-propyl alcohol, iso-butyl alcohol, tert-butanol, neopentyl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane trimethacrylate, pentaerythritol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, hydrogenated bisphenol A, bisphenol A ethylene oxide adduct, bisphenol A propylene oxide adduct, etc., and glycidol; 【0048】 Glycidyl ester epoxy compounds are condensates of carboxylic acid compounds such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, isobutyric acid, isovaleric acid, benzoic acid, benzoylacetic acid, naphthalenecarboxylic acid, adipic acid, sebatic acid, dodecanedicarboxylic acid, dimer acid, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, hexahydroisophthalic acid, hexahydroterephthalic acid, hetic acid, nadic acid, maleic acid, succinic acid, fumaric acid, trimellitic acid, benzenetetracarboxylic acid, benzophenonetetracarboxylic acid, naphthalenedicarboxylic acid, and diphenyldicarboxylic acid, and glycidol; 【0049】 Methylamine, ethylamine, propylamine, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, bis-(3-aminopropyl)ether, 1,2-bis-(3-aminopropoxy)ethane, 1,3-bis-(3-aminopropoxy)-2,2'-dimethylpropane, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4 Primary amines such as bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, isophoronediamine, 1,4-bisaminopropylpiperazine, m- or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, and 2,2-(4,4'-diaminodiphenyl)propane; 【0050】 Dimethylamine, diethylamine, dibutylamine, methylethylamine, methylpropylamine, methylbutylamine, methylpentylamine, methylhexylamine, ethylpropylamine, ethylbutylamine, ethylpentylamine, ethylhexylamine, N,N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N,N'-dimethyl-1,3-diaminobutane, N,N'-dimethyl-1, 4-Diaminobutane, N,N'-dimethyl-1,5-diaminopentane, N,N'-dimethyl-1,6-diaminohexane, N,N'-dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N,N'-diethyl-1,2-diaminobutane, N,N'-diethyl-1,3-diaminobutane, N,N'-diethyl-1, Amine-based epoxy compounds produced by the reaction of secondary amines such as 4-diaminobutane, N,N'-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di-(4-piperidyl)-methane, 1,2-di-(4-piperidyl)-ethane, 1,3-di-(4-piperidyl)-propane, and 1,4-di-(4-piperidyl)-butane with epihalohydrins; 【0051】 Alicyclic epoxy compounds such as cyclohexene oxide, 3,4-epoxycyclohexyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexane dioxide, 1,2:8,9-diepoxylimonene, 2-(3,4-epoxycyclohexyl)-5,5-spiro-3,4-epoxycyclohexane-meth-dioxane, and bis(3,4-epoxycyclohexyl) adipate; Epoxy compounds produced by epoxidizing unsaturated compounds such as styrene oxide, cyclopentadiene epoxide, epoxidized soybean oil, epoxidized polybutadiene, and vinylcyclohexene epoxide; Urethane epoxy compounds produced from polyhydric alcohols or phenolic compounds, diisocyanates, and glycidol; These are some examples. 【0052】 From the viewpoint of further improving the heat resistance of the resulting resin, the epoxy compound (X) (for example, the epoxy compound (X1) described above; the same applies hereinafter) preferably contains an aromatic ring, more preferably contains an aromatic ring and a glycidyloxy group, and even more preferably contains an aromatic ring and two or more (preferably two to four, more preferably two or three, and even more preferably two) glycidyloxy groups. From the viewpoint of further improving the heat resistance of the resulting resin, the molecular weight of the epoxy compound (X) is preferably 1000 or less, more preferably 500 or less, and even more preferably 400 or less. The lower limit of the molecular weight of the epoxy compound (X) is preferably 100, and more preferably 200. 【0053】 The epoxy compound (X) preferably contains at least one selected from the group consisting of bisphenol A diglycidyl ether (hereinafter also referred to as "BGPP") (molecular weight 340) and resorcinol diglycidyl ether (molecular weight 222). In this case, the total proportion of bisphenol A diglycidyl ether and resorcinol diglycidyl ether in the total amount of epoxy compound (X) is preferably 50% to 100% by mass, more preferably 60% to 100% by mass, and even more preferably 80% to 100% by mass. 【0054】 The content of epoxy compound (X) relative to the total amount of the polymerizable composition of this disclosure is preferably 0.05% by mass or more, more preferably 0.10% by mass or more, and even more preferably 0.20% by mass or more, from the viewpoint of further improving the hue of the obtained resin. The content of epoxy compound (X) relative to the total amount of the polymerizable composition of this disclosure is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 3% by mass or less, from the viewpoint of superior strength of the resulting resin. A preferred range for the content of epoxy compound (X) relative to the total amount of the polymerizable composition of this disclosure is, for example, 0.05% by mass to 20% by mass. 【0055】 <(M S -M N ) / M E ratio> In the polymerizable compositions of this disclosure, The total number of moles of mercapto groups contained in the total amount of the polythiol compound is M S year, The total number of moles of iso(thio)cyanate groups in the total amount of the polyiso(thio)cyanate compound is M. N year, The total number of moles of episulfide groups contained in the total amount of the episulfide compound represented by formula (1) is M. E In that case, (M S -M N ) / M E The ratio is preferably greater than 0 and less than or equal to 0.20, and more preferably greater than 0 and less than or equal to 0.15. 【0056】 (M S -M N ) / M E When the ratio is greater than 0, the strength of the resulting resin is further improved. (M S -M N ) / M E When the ratio is 0.20 or less, the heat resistance of the resulting resin is further improved. 【0057】 <Compound represented by formula (2)> The polymerizable compositions of this disclosure preferably contain a compound represented by the following formula (2). The compound represented by the following formula (2) can function as a curing catalyst. When the polymerizable composition of this disclosure contains a compound represented by the following formula (2), the strength of the resulting resin can be further improved. If the polymerizable composition of this disclosure contains a compound represented by the following formula (2), then the contained The compound represented by formula (2) may be one type or two or more types. 【0058】 (R 1 )4Y + X- …(2) 【0059】 In equation (2), the four R 1 Each of these independently represents a straight-chain hydrocarbon group with 1 to 10 carbon atoms or a branched hydrocarbon group with 3 to 10 carbon atoms, X represents a halogen atom, and Y represents a nitrogen atom or a phosphorus atom. 【0060】 In formula (2), R 1 The "linear hydrocarbon group having 1 to 10 carbon atoms or a branched hydrocarbon group having 3 to 10 carbon atoms" represented by the formula is preferably a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms. From the viewpoint of improving the appearance of the resulting resin, R 1 The "linear hydrocarbon group having 1 to 10 carbon atoms or a branched hydrocarbon group having 3 to 10 carbon atoms" represented by the above is more preferably a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms, and even more preferably a linear alkyl group having 1 to 6 carbon atoms. 【0061】 In formula (2), the halogen atom represented by X is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and even more preferably a chlorine atom or a bromine atom. From the viewpoint of improving the appearance of the resulting resin, the halogen atom represented by X is particularly preferably a bromine atom. 【0062】 In formula (2), Y may be a nitrogen atom or a phosphorus atom, but is preferably a nitrogen atom. 【0063】 The compound represented by formula (2) is preferably tetra-n-butylammonium bromide (TBAB) or tri-n-octylmethylammonium chloride (TOMAC). Tetra-n-butylammonium bromide (TBAB) is a compound in formula (2) with four R 1 Each of these is an n-butyl group, Y is a nitrogen atom, and X is a bromine atom in this compound. 【0064】 The content of the compound represented by formula (2) in the polymerizable composition is preferably 0.01% to 1% by mass, more preferably 0.01 to 0.5% by mass, and even more preferably 0.01 to 0.3% by mass, relative to the total amount of the episulfide compound, polyiso(thio)cyanate compound, and polythiol compound represented by formula (1). 【0065】 <Tertiary amine compounds> The polymerizable composition of this disclosure preferably contains a tertiary amine compound. Tertiary amine compounds can function as curing catalysts. When the polymerizable composition of this disclosure contains a tertiary amine compound, the appearance of the resulting resin can be improved. If the polymerizable composition of this disclosure contains a tertiary amine compound, the contained tertiary amine compound may be one type or two or more types. 【0066】 The polymerizable compositions of this disclosure may contain both a compound represented by formula (2) and a tertiary amine compound (for example, at least one of a compound represented by formula (3) and a compound represented by formula (4)). 【0067】 The tertiary amine compound preferably contains at least one of the compound represented by the following formula (3) and the compound represented by the following formula (4). 【0068】 (The compound represented by formula (3)) If the polymerizable composition of this disclosure contains a compound represented by the following formula (3), the compound represented by formula (3) may be just one type or two or more types. 【0069】 [ka] 【0070】 In formula (3), each of the m R1 atoms independently represents a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a halogen atom; Q represents a carbon atom, a nitrogen atom, or an oxygen atom; and m represents an integer from 0 to 5. 【0071】 In equation (3), m is preferably an integer between 0 and 3, and more preferably an integer between 1 and 3. 【0072】 In formula (3), examples of linear alkyl groups having 1 to 20 carbon atoms represented by R1 include methyl, ethyl, n-propyl, n-butyl, pentyl, hexyl, heptyl, n-octyl, nonyl, decyl, and dodecyl groups. In formula (3), the branched alkyl group having 3 to 20 carbon atoms represented by R1 includes isopropyl group, isobutyl group, t-butyl group, isopentyl group, isooctyl group, 2-ethylhexyl group, 2-propylpentyl group, and isodecyl group. In formula (3), examples of cycloalkyl groups having 3 to 20 carbon atoms represented by R1 include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group. 【0073】 In formula (3), R1 is preferably a linear alkyl group having 1 to 20 carbon atoms or a halogen atom, and more preferably a linear alkyl group having 1 to 3 carbon atoms or a chlorine atom. 【0074】 The compound represented by formula (3) is preferably at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chlorpyridine, 2-ethylpyridine, and 3-ethylpyridine. 【0075】 (The compound represented by formula (4)) If the polymerizable composition of this disclosure contains a compound represented by the following formula (4), the compound represented by formula (4) may be just one type or two or more types. 【0076】 [ka] 【0077】 In formula (4), R2, R3, and R4 each independently represent a linear alkyl group having 3 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an allyl group. R2 and R3 may be bonded to each other to form a ring. 【0078】 In formula (4), R2, R3, and R4 are each independently preferably linear alkyl groups having 3 to 20 carbon atoms, more preferably linear alkyl groups having 3 to 10 carbon atoms, and particularly preferably linear alkyl groups having 5 to 10 carbon atoms. 【0079】 Examples of linear alkyl groups having 3 to 20 carbon atoms represented by R2, R3, or R4 include n-propyl, n-butyl, pentyl, hexyl, heptyl, n-octyl, nonyl, decyl, and dodecyl groups. 【0080】 R2 and R3 may be bonded to each other to form a ring. In other words, the compound represented by formula (4) may be a cyclic amine compound having a structure in which R2 and R3 are bonded to each other to form a ring. Examples of the above-mentioned cyclic amine compounds include 1-propylpiperidine, 1-butylpiperidine, 1-cyclohexylpiperidine, 1-butylpyrrolidine, and 1-cyclohexylpyrrolidine. 【0081】 The compound represented by formula (4) is preferably at least one selected from the group consisting of triallylamine and trioctylamine. 【0082】 The content of the tertiary amine compound in the polymerizable composition (for example, the total content of the compound represented by formula (3) and the compound represented by formula (4)) is preferably 0.01% to 1% by mass, more preferably 0.01% to 0.5% by mass, and even more preferably 0.01% to 0.5% by mass, relative to the total amount of the episulfide compound represented by formula (1), the polyiso(thio)cyanate compound, and the polythiol compound. 【0083】 The total content of the compound represented by formula (2) and the tertiary amine compound in the polymerizable composition (for example, the total content of the compounds represented by formulas (2) to (4)) is preferably 0.01% to 1% by mass, more preferably 0.01 to 0.5% by mass, and even more preferably 0.01 to 0.5% by mass, relative to the total amount of the episulfide compound, polyiso(thio)cyanate compound, and polythiol compound represented by formula (1). 【0084】 The polymerizable compositions of this disclosure may contain, as curing catalysts, other compounds besides those represented by formulas (2) to (4) described above. The curing catalyst can be selected from, for example, the curing catalysts described in paragraphs 0029 to 0033 of Japanese Patent Publication No. 2002-194083. 【0085】 <Lewis acid compounds> The polymerizable compositions of this disclosure preferably contain Lewis acid compounds. This can further improve the pot life of polymerizable compositions. If the polymerizable composition of this disclosure contains a Lewis acid compound, the Lewis acid compound contained may be one type or two or more types. 【0086】 There are no particular restrictions on Lewis acid compounds, but examples include organotin compounds, zinc chloride, zinc acetylacetone, aluminum chloride, aluminum fluoride, triphenylaluminum, tetrachlorotitanium, calcium acetate, and the like. For Lewis acid compounds, you may appropriately refer to the descriptions in prior art such as Japanese Patent Publication No. 2000-256435 (especially paragraphs 0059-0060), Japanese Patent Publication No. 2005-272778 (especially paragraph 0058), and Japanese Patent Publication No. 2001-131257 (especially paragraph 0027). 【0087】 There are no particular restrictions on the organotin compounds, but for example; Dialkyltin halides such as dibutyltin dichloride and dimethyltin dichloride; dialkyltin dicarboxylates such as dimethyltin diacetate, dibutyltin dioctanoate, and dibutyltin dilaurate; Tetrachlorotin; Dibutyltin oxide; These are some examples. 【0088】 Dialkyltin halides may also include monoalkyltin halides and trialkyltin halides. Dialkyltin dicarboxylates may also include monoalkyltin tricarboxylates and trialkyltin carboxylates. 【0089】 From the viewpoint of further improving the pot life of the polymerizable composition, it is preferable that the Lewis acid compound includes a specific organotin compound represented by the following formula (5). 【0090】 [ka] 【0091】 In formula (5), R4 represents an alkyl group having 1 to 4 carbon atoms, X represents a fluorine atom, a chlorine atom, a bromine atom, or -OC(=O)-R5, R5 represents an alkyl group having 1 to 11 carbon atoms, and c represents an integer from 1 to 3. 【0092】 The compound represented by formula (5) is preferably at least one selected from the group consisting of dimethyltin dichloride, dibutyltin dichloride, and dibutyltin dilaurate. 【0093】 The content of Lewis acid compounds (for example, organotin compounds such as the compound represented by formula (5)) is preferably 100 ppm to 500 ppm by mass, and more preferably 200 ppm to 400 ppm by mass, based on the total amount of the polymerizable composition. 【0094】 <Other ingredients> The polymerizable compositions of this disclosure may contain other components besides those described above. Other ingredients include bluing agents, mercapto-organic acids, and resins (e.g., acrylic). Examples include resins (olefin resins, etc.), crosslinking agents, light stabilizers, UV absorbers, antioxidants, color inhibitors, dyes, fillers, and internal release agents. Other known ingredients can be used. For other components, refer to, for example, Japanese Patent Publication No. 2002-194083 as appropriate. 【0095】 The polymerizable composition of this disclosure is obtained by mixing the above-mentioned components (raw materials). There are no particular restrictions on the order in which the ingredients (raw materials) are mixed. All raw materials may be added to the container at once and mixed, or they may be added to the container in multiple stages and mixed. Furthermore, during the mixing process, some of the monomers in the polymerizable composition of this disclosure may polymerize to form a prepolymer. The monomers in the polymerizable compositions of this disclosure mean at least an episulfide compound represented by formula (1), a polyiso(thio)cyanate compound, and a polythiol compound. In addition to these compounds, epoxy compound (X) may also function as a monomer. 【0096】 [Resin, molded products] The resin of this disclosure is a cured product of the polymerizable composition of this disclosure described above. The molded articles of this disclosure include the resin of this disclosure. 【0097】 That is, the resin of the present disclosure can be produced by curing the polymerizable composition of the present disclosure described above, or more specifically, by polymerizing and curing the monomers in the polymerizable composition of the present disclosure. 【0098】 One method for polymerizing the monomers in the polymerizable composition of the present disclosure is casting polymerization. By casting polymerization, a molded article of the present disclosure is obtained, which contains the resin of the present disclosure (i.e., a cured product of the polymerizable composition of the present disclosure). 【0099】 In casting polymerization, first, a polymerizable composition according to an example of this disclosure is injected between a pair of molding molds held together by a gasket or tape. At this time, degassing, filtration, etc. may be performed as necessary. Next, the monomers in the composition injected between the molding molds are polymerized, causing the composition to harden between the molding molds and obtain a cured product. Then, the cured product is removed from the molding molds to obtain a cured product. Polymerization of the above monomers may be carried out by heating the polymerizable composition of this disclosure. This heating can be carried out, for example, using a heating device equipped with a mechanism for heating the object to be heated in an oven, water, or the like. 【0100】 The polymerization conditions (e.g., polymerization temperature, polymerization time, etc.) for polymerizing the monomers in the polymerizable composition of this disclosure are set appropriately, taking into consideration the composition of the composition, the type and amount of monomers used in the composition, the type and amount of polymerization catalyst used in the composition, the shape of the mold, etc. Examples of polymerization temperatures include -50°C to 150°C and 10°C to 150°C. Polymerization times can range from 1 hour to 200 hours, 1 hour to 80 hours, and so on. 【0101】 The resin or molded article containing the resin of this disclosure may be obtained by polymerizing the monomers and then subjecting them to treatments such as annealing. Typical annealing temperatures include 50°C to 150°C, 90°C to 140°C, and 100°C to 130°C. 【0102】 [Optical materials] The optical materials of this disclosure include the resins of this disclosure as described above. The optical materials of this disclosure can be manufactured, for example, by the casting polymerization described above. 【0103】 The optical material of this disclosure may consist of the resin of this disclosure, or may include the resin of this disclosure and other elements. Other elements include other components, a coating layer applied to the resin of this disclosure, and so on. 【0104】 Examples of optical materials in this disclosure include lenses (e.g., eyeglass lenses, camera lenses, polarizing lenses, etc.), light-emitting diodes (LEDs), and the like. 【0105】 〔lens〕 The lenses of this disclosure are an example of the optical materials of this disclosure, and include the resins of this disclosure as described above. The lenses of this disclosure may be manufactured, for example, by the casting polymerization described above. 【0106】 The lenses of this disclosure may consist of the resin of this disclosure, or may include the resin of this disclosure and other elements. Other elements include other components, a coating layer applied to the resin of this disclosure, and so on. 【0107】 Examples of lenses in this disclosure include eyeglass lenses, camera lenses, polarized lenses, and the like. Below, we will describe eyeglass lenses as an example of the lenses described herein. The spectacle lens comprises a resin of the present disclosure molded into a desired lens shape. The spectacle lens preferably further includes a coating layer provided on one or both sides of the resin. 【0108】 Examples of coating layers include primer layers, hard coat layers, anti-reflective layers, anti-fogging layers, anti-stain layers, and water-repellent layers. These coating layers can be used individually or in multiple layers. When applying coating layers to both sides of a cured object, the same coating layer may be applied to each surface, or different coating layers may be applied to each surface. 【0109】 The components of the coating layer can be selected as appropriate depending on the purpose. The components of the coating layer include, for example, resins (e.g., urethane resin, epoxy resin, polyester resin, melamine resin, polyvinyl acetal resin, etc.), infrared absorbers, light stabilizers, antioxidants, photochromic compounds, dyes, pigments, antistatic agents, and the like. 【0110】 For eyeglass lenses and coating layers, you can refer to the descriptions in publicly available documents such as Japanese Patent Publication No. 2002-194083 and International Publication No. 2017 / 047745 as appropriate. [Examples] 【0111】 The following are examples of the present disclosure, but the present disclosure is not limited to these examples. Unless otherwise specified, "parts" are based on mass. 【0112】 [Example 1] <Preparation of polymerizable compositions> 26.5 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 as polyiso(thio)cyanate compounds (hereinafter also referred to as "PI-1"), Bisphenol A diglycidyl ether (hereinafter referred to as "BG") as epoxy compound (X) 0.68 parts by mass (also called "PP") 0.067 parts by mass of tetrabutylammonium bromide (hereinafter also referred to as "TBAB"), which is a compound represented by formula (2), as a curing catalyst, 0.050 parts by mass of "ZELEC UN" (product name; acidic phosphate ester mold release agent manufactured by Stepan) as a release agent, 0.088 parts by mass of "TinuvinPS" (manufactured by BASF Japan) as an ultraviolet absorber, The two substances were mixed and dissolved at 20°C. To the obtained solution, 45.4 parts by mass of bis(2,3-epithiopropyl) disulfide (hereinafter also referred to as "EPS-1") as an episulfide compound represented by formula (1), 28.1 parts by mass of a polythiol composition (hereinafter also referred to as "PT-1") mainly composed of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, The components were added in this order and mixed to obtain a polymerizable composition. 【0113】 Table 1 shows the types and amounts of each component contained in the polymerizable composition. In Table 1, the notation "-" indicates that the corresponding ingredient is not present. Table 1 shows (M) in polymerizable compositions. S -M N ) / M E The ratio was also shown. Here, (M S -M N ) / M E The ratio is the total number of moles of mercapto groups contained in the total amount of the polythiol compound, M S Let M be the total number of moles of iso(thio)cyanate groups in the total amount of the polyiso(thio)cyanate compound. N Let M be the total number of moles of episulfide groups contained in the total amount of the episulfide compound represented by formula (1). E (M S -M N ) / M E Ratio (roughly speaking, excess thiol groups (M S -M N) has an episulfide group (M E This is the ratio to ). 【0114】 <Fabrication of resin molded products> The polymerizable composition obtained above was filtered through a 3 μm Teflon® filter, and then degassed thoroughly under a reduced pressure of 600 Pa until no more foaming was observed. The degassed polymerizable composition was poured between a pair of glass molds fixed together with tape. Next, the pair of glass molds containing the polymerizable composition were placed in an oven, and the oven temperature was gradually increased from 30°C to 120°C over 15 hours. Through this process, the monomers in the degassed polymerizable composition (i.e., episulfide compounds represented by formula (1), polyiso(thio)cyanate compounds, polythiol compositions, etc.) were polymerized, and a resin molded body (i.e., a resin molded body which is a cured product of the polymerizable composition) was formed between the pair of glass molds. Next, the oven was cooled, and after cooling, the pair of glass molds were removed from the oven. Then, the resin molded bodies were removed from the pair of glass molds to obtain the resin molded bodies. The obtained resin molded bodies were annealed at 120°C for 1 hour to obtain resin-containing lenses. 【0115】 <Rating> The following evaluations were performed on the above polymerizable compositions or resin molded articles. The results are shown in Table 1. 【0116】 • Optical properties (refractive index (n) e ) and Abbe number (ν e )) Using a Shimadzu KPR-30 Pulfrich refractometer, the refractive index was measured at wavelengths of 546.1 nm (mercury e line), 480.0 nm (Cd F' line), and 643.9 nm (Cd C' line). Based on these measurement results, the refractive index (n e ) and Abbe number (ν e We calculated each of the following: 【0117】 ·Heat resistance Aside from appropriately selecting the shape and size of a pair of glass molds, the same procedure as described in <Preparation of Resin Molded Body> was used to obtain a test piece with a length of 10 mm, a width of 10 mm, and a thickness of 2.5 mm. Using a Shimadzu TMA-60 thermomechanical analyzer, the glass transition temperature (Tg) of the above sample was measured by the TMA penetration method (50g load, 0.5mmφ pin tip, heating rate 10℃ / min) and used as an indicator of heat resistance. The higher the glass transition temperature (Tg), the better the heat resistance. 【0118】 • Bending strength (flexural modulus) A rectangular, flat test piece measuring 65 mm in length, 25 mm in width, and 2.5 mm in thickness was obtained by the same procedure as described in <Preparation of Resin Molded Body>, except that the shape and size of a pair of glass molds were appropriately selected. Three-point bending tests were performed on the obtained test specimens using a Shimadzu AUTOGRAPH AGS-J, and the flexural modulus of the samples was determined based on the range in which forces of 20N to 30N were applied to the samples. 【0119】 • Hole drilling tensile strength Except for appropriately selecting the shape and size of a pair of glass molds, the same procedure as in the above-described procedure for "Preparation of Resin Molded Body" was used to produce a disc-shaped molded body with S=-2.00D and a diameter of 45 mm. I got it. Two 1.6 mm diameter holes were drilled at two points, 5 mm off-center from each end of the obtained disc-shaped molded body, to create test specimens. Using a Shimadzu AUTOGRAPH AGS-J, pins were passed through the two holes to measure the drilling strength, and the permanent strain of 0.5% was used as the yield point, serving as an indicator of drilling strength. 【0120】 • YI (Yellow Index; degree of yellowness), a * , and b * Except for appropriately selecting the shape and size of a pair of glass molds, a disc-shaped test specimen with a thickness of 2.5 mm and a diameter of 75 mm was obtained by the same procedure as in the above-described procedure for "Preparation of Resin Molded Body". The obtained test specimen was measured using a Konica Minolta CM-5 spectrophotometer to determine the YI (Yellow Index; yellowness), a * , and b * They sought it. The smaller the YI value, the better the lens's color reproduction. 【0121】 ·exterior The test specimens (resin molded bodies) used for the above-mentioned YI measurements were visually observed, and their appearance was evaluated according to the evaluation criteria below. 【0122】 - Criteria for evaluating appearance - A: No pattern was visible at all, and the appearance was good. B: When observed at close range, streaky or spotted patterns were visible, but when observed from a distance of 50 cm, the patterns were not visible, and the appearance was within practically acceptable limits. C: The pattern was visible when observed from a distance of 50 cm, and the appearance exceeded the practically acceptable range. 【0123】 [Example 2] The procedure was the same as in Example 1, except that the components of the polymerizable composition were changed as shown in Table 1. The results are shown in Table 1. In Table 1, PT-2 is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane. 【0124】 [Example 3] Except for the following points, the same procedure as in Example 1 was followed. The results are shown in Table 1. -Changes from Example 1- The components of the polymerizable composition were changed as shown in Table 1. In Table 1, PI-2 is xylylene diisocyanate, and TOMAC is tri-n-octylmethylammonium chloride. After mixing all the components, the mixture was further stirred at 20°C for 1 hour to obtain a polymerizable composition. • The filtration step in the <Preparation of resin molded products> was omitted. 【0125】 [Example 4] The procedure was the same as in Example 3, except that the type and amount of curing catalyst were changed as shown in Table 1. The results are shown in Table 1. -Changes from Example 1- The components of the polymerizable composition were changed as shown in Table 1. 3,5-Lutidine was used after being dissolved in a polythiol composition mainly composed of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane. 【0126】 [Comparative Example 1] The polymerizable compositions and resin molded articles shown below were prepared, and the obtained polymerizable compositions and resin molded articles were evaluated in the same manner as in Example 1. The results are shown in Table 1. 【0127】 <Preparation of polymerizable compositions> 90.9 parts by mass of bis(2,3-epithiopropyl)disulfide (EPS-1) as an episulfide compound represented by formula (1), 1 part by mass of "TinuvinPS" (manufactured by BASF Japan) as an ultraviolet absorber, and 8.2 parts by mass of a polythiol composition (PT-1) mainly composed of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 0.091 parts by mass of N,N-dicyclohexylmethylamine (hereinafter also referred to as "DCH") as a curing catalyst, The ingredients were mixed and dissolved in this order at 20°C. To the obtained solution, 0.018 parts by mass of N,N-dimethylcyclohexylamine (hereinafter also referred to as "DCA") as a curing catalyst, 0.9 parts by mass of a polythiol composition (PT-1) mainly composed of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, The mixture was charged and mixed at 20°C to obtain a polymerizable composition. 【0128】 <Fabrication of resin molded products> The polymerizable composition obtained above was filtered through a 1 μm Teflon® filter, and then degassed thoroughly under reduced pressure of 600 Pa until no more foaming was observed. The degassed polymerizable composition was poured between a pair of glass molds fixed together with tape. Next, the pair of glass molds containing the polymerizable composition were placed in an oven, and the oven temperature was gradually increased from 30°C to 80°C over 21 hours. Through this process, the monomers in the degassed polymerizable composition (i.e., the episulfide compound polythiol composition represented by formula (1), etc.) were polymerized, and a resin molded body (i.e., a resin molded body which is the cured product of the polymerizable composition) was formed between the pair of glass molds. Next, the oven was cooled, and after cooling, the pair of glass molds were removed from the oven. Then, the resin molded bodies were removed from the pair of glass molds to obtain the resin molded bodies. The obtained resin molded bodies were annealed at 120°C for 3 hours to obtain resin-containing lenses. 【0129】 [Table 1] 【0130】 As shown in Table 1, polymerizable compositions of Examples 1 to 4, each containing an episulfide compound represented by formula (1), a polyiso(thio)cyanate compound, a polythiol compound, and an epoxy compound (X) containing one or more epoxy groups in one molecule but not an episulfide group, were able to produce resin molded articles with a high refractive index and excellent strength (particularly strength in tensile drilling tests). In contrast, the resin molded article obtained using the resin composition of Comparative Example 1 had a high refractive index, but its strength (particularly in the tensile strength test) was inferior. 【0131】 [Example 101] <Preparation of polymerizable compositions> 25.4 parts by mass of PI-2 (i.e., xylylene diisocyanate) as a polyiso(thio)cyanate compound, 1.00 parts by mass of BGPP (i.e., bisphenol A diglycidyl ether) as epoxy compound (X), 0.04 parts by mass of dimethyltin dichloride (hereinafter also referred to as "DMC") as a Lewis acid compound (more specifically, the compound represented by formula (5)), 0.03 parts by mass of "ZELEC UN" (product name; acidic phosphate ester mold release agent manufactured by Stepan) as a release agent, 0.088 parts by mass of "TinuvinPS" (manufactured by BASF Japan) as an ultraviolet absorber, The two substances were mixed and dissolved at 20°C. To the obtained solution, After charging 42.6 parts by mass of EPS-1 (i.e., bis(2,3-epithiopropyl)disulfide), which is an episulfide compound represented by formula (1), A mixture of 32.0 parts by mass of PT-1 (i.e., a polythiol composition mainly composed of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane) and 0.03 parts by mass of 3,5-lutidine, a curing catalyst represented by formula (3), was charged and mixed at 5 to 10°C to obtain a polymerizable composition. 【0132】 <Fabrication of resin molded products> The polymerizable composition obtained above was degassed under a reduced pressure of 600 Pa until no more foaming was observed. The degassed polymerizable composition was poured between a pair of glass molds fixed together with tape. Next, the pair of glass molds containing the polymerizable composition were placed in an oven, and the oven temperature was gradually increased from 20°C to 120°C over 23 hours. Through this process, the monomers in the degassed polymerizable composition (i.e., episulfide compounds represented by formula (1), polyiso(thio)cyanate compounds, polythiol compositions, etc.) were polymerized, and a resin molded body (i.e., a resin molded body which is a cured product of the polymerizable composition) was formed between the pair of glass molds. Next, the oven was cooled, and after cooling, the pair of glass molds were removed from the oven. Then, the resin molded bodies were removed from the pair of glass molds to obtain the resin molded bodies. The obtained resin molded bodies were annealed at 120°C for 1 hour to obtain resin-containing lenses. 【0133】 <Rating> The following evaluations were performed on the above polymerizable compositions or resin molded articles. The results are shown in Table 2. 【0134】 • Viscosity of polymerizable compositions The polymerizable composition was stirred at 10°C for 1 hour, and its viscosity was measured using a Brookfield Type B viscometer (spindle No. 62). The lower the viscosity value, the longer the pot life. 【0135】 • Heat resistance, YI (Yellow Index; degree of yellowness) The heat resistance and YI (Yellow Index; degree of yellowness) of the resin molded article were evaluated in the same manner as in Example 1. 【0136】 [Examples 102-106] The procedure was the same as in Example 101, except that the components of the polymerizable composition were changed as shown in Table 2. They did that. The results are shown in Table 2. In Table 2, DBC refers to dibutyltin dichloride as a Lewis acid compound (specifically, the compound represented by formula (5)). Furthermore, in Table 2, the "-" in the "Lewis acid compound (compound represented by formula (5))" column for Example 106 means that a Lewis acid compound was not used. 【0137】 [Table 2] 【0138】 As shown in Table 2, among Examples 101 to 106, Examples 101 to 105, in which the polymerizable composition contained a Lewis acid compound, showed a reduction in the viscosity of the polymerizable composition compared to Example 106, in which the polymerizable composition did not contain a Lewis acid compound, and it was confirmed that these examples had superior pot life. 【0139】 The disclosures of Japanese Patent Application No. 2021-017406, filed on 5 February 2021, and Japanese Patent Application No. 2021-124416, filed on 29 July 2021, are incorporated herein by reference in their entirety. All documents, patent applications, and technical standards described herein are incorporated by reference to the same extent as if each individual document, patent application, and technical standard were specifically and individually noted to be incorporated by reference.

Claims

[Claim 1] An episulfide compound represented by the following formula (1), Polyiso(thio)cyanate compounds, Polythiol compounds and An epoxy compound (X) containing one or more epoxy groups in one molecule and not containing an episulfide group, A polymerizable composition containing, Let M S be the total number of moles of mercapto groups contained in the total amount of the polythiol compound. Let M be the total number of moles of iso(thio)cyanate groups in the total amount of the polyiso(thio)cyanate compound. When M is the total number of moles of episulfide groups contained in the total amount of the episulfide compound represented by formula (1), The (MS -MN) / ME ratio is greater than 0 and less than or equal to 0.

20. Polymerizable composition. 【Chemistry 1】 [In formula (1), Y represents a substituted or unsubstituted linear hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted branched hydrocarbon group having 2 to 4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3 to 6 carbon atoms, a substituted or unsubstituted 1,4-dithiane group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group; m represents an integer from 0 to 2; and n represents an integer from 0 to 3.] [Claim 2] The polymerizable composition according to claim 1, wherein the epoxy compound (X) comprises an epoxy compound (X1) having two or more epoxy groups in one molecule. [Claim 3] The aforementioned polythiol compounds are 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, 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptoethyl) sulfide, 1, A polymerizable composition according to claim 1 or claim 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-dithiethane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane. [Claim 4] The aforementioned polyiso(thio)cyanate compounds include 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, and tolylene diiso Cyanates, 4,4'-diphenylmethane diisocyanate, and phenylenediisocyanate A polymerizable composition according to any one of claims 1 to 3, comprising at least one selected from the group consisting of nates. [Claim 5] Furthermore, the polymerizable composition according to any one of claims 1 to 4, comprising a compound represented by the following formula (2). (R １ ) ４ Y ＋ X － …(2) [In equation (2), the four R's １ Each of these independently represents a linear hydrocarbon group having 1 to 10 carbon atoms or a branched hydrocarbon group having 3 to 10 carbon atoms, X represents a halogen atom, and Y represents a nitrogen atom or a phosphorus atom. [Claim 6] Furthermore, the polymerizable composition according to any one of claims 1 to 5, further containing a tertiary amine compound. [Claim 7] The polymerizable composition according to claim 6, wherein the tertiary amine compound comprises at least one of the compound represented by the following formula (3) and the compound represented by the following formula (4). 【Chemistry 2】 [In equation (3), m R １ Each of these independently represents a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a halogen atom; Q represents a carbon atom, a nitrogen atom, or an oxygen atom; and m represents an integer from 0 to 5. In formula (4), R ２ , R ３ , and R ４ each independently represent a linear alkyl group having 3 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an allyl group. R ２ and R ３ may be bonded to each other to form a ring. ]] [Claim 8] The compound represented by formula (3) is at least one selected from the group consisting of 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chlorpyridine, 2-ethylpyridine, and 3-ethylpyridine. The compound represented by formula (4) is at least one selected from the group consisting of triallylamine and trioctylamine. The polymerizable composition according to claim 7. [Claim 9] The polymerizable composition according to any one of claims 1 to 4, further comprising at least one selected from the group consisting of tetrabutylammonium bromide, tri-n-octylmethylammonium chloride, and 3,5-lutidine. [Claim 10] Furthermore, the polymerizable composition according to any one of claims 1 to 9, further containing a Lewis acid compound. [Claim 11] The polymerizable composition according to claim 10, wherein the Lewis acid compound comprises a compound represented by the following formula (5). 【Transformation 3】 [In formula (5), R ４ represents an alkyl group having 1 to 4 carbon atoms, and X is a fluorine atom, a chlorine atom, a bromine atom, or -O-C(=O)-R ５ Represents R ５ [where 'c' represents an alkyl group with 1 to 11 carbon atoms, and 'c' represents an integer from 1 to 3.] [Claim 12] The polymerizable composition according to claim 11, wherein the compound represented by formula (5) is at least one selected from the group consisting of dimethyltin dichloride, dibutyltin dichloride, and dibutyltin dilaurate. [Claim 13] A resin which is a cured product of a polymerizable composition according to any one of claims 1 to 12. [Claim 14] A molded article comprising the resin described in claim 13. [Claim 15] An optical material comprising the resin described in claim 13. [Claim 16] A lens comprising the resin described in claim 13.

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