Composition for optical material, polymerizable composition for optical material, optical material, and lens

Abstract

Provided is a composition for an optical material, the composition comprising a modified aliphatic polyisocyanate and an acidic compound.

Description

Compositions for optical materials, polymerizable compositions for optical materials, optical materials, and lenses

[0001] This disclosure relates to compositions for optical materials, polymerizable compositions for optical materials, optical materials, and lenses.

[0002] Traditionally, glass optical materials have been used for optical materials (such as lenses). In recent years, however, the use of resin-based optical materials has expanded due to their lightweight properties and moldability.

[0003] For example, Patent Document 1 discloses a polymerizable composition for optical materials containing a polyisocyanate and a polythiol, as a polymerizable composition for optical materials for manufacturing resin-based optical materials. Specifically, Patent Document 1 discloses a polymerizable composition for optical materials containing a polyisocyanate component (a) including an aliphatic polyisocyanate (a1) and a polyisocyanate modified product of an aliphatic polyisocyanate, and a polythiol (b) having two or more thiol groups. Patent Document 1 states that, according to the polymerizable composition for optical materials described in the document, optical materials with excellent physical properties such as transparency, refractive index, heat resistance, and strength can be obtained.

[0004] Patent Document 1: International Publication No. 2015 / 119220

[0005] However, in optical materials obtained using compositions containing aliphatic polyisocyanate modifiers, it is sometimes required to further reduce striations. An object of one aspect of this disclosure is to provide an optical material composition containing an aliphatic polyisocyanate modifier that can produce an optical material with reduced striations, a polymerizable composition for optical materials containing an aliphatic polyisocyanate modifier that can produce an optical material with reduced striations, an optical material with reduced striations, and a lens with reduced striations.

[0006] The means for solving the above problems include the following embodiments: <1> A composition for optical materials containing an aliphatic polyisocyanate modified material and an acidic compound. <2> The composition for optical materials according to <1>, wherein the content of the aliphatic polyisocyanate modified material is 50% by mass or more of the total amount of the composition for optical materials. <3> The composition for optical materials according to <1> or <2>, wherein the acidic compound comprises a compound (b) selected from the group consisting of an acid (b1) having a pKa of less than 10.0 and an anhydride (b2) of an acid having a pKa of less than 10.0. <4> The composition for optical materials according to <3>, wherein the acid (b1) contains a sulfonic acid having a pKa of less than 10.0, and the anhydride (b2) contains an anhydride of a sulfonic acid having a pKa of less than 10.0. <5> The optical material composition according to <3>, wherein the acid (b1) comprises at least one selected from the group consisting of 10-camphor sulfonic acid, methanesulfonic acid, paraphenolsulfonic acid, benzenesulfonic acid, and paratoluenesulfonic acid, and the anhydride (b2) comprises at least one selected from the group consisting of 10-camphor sulfonic acid anhydride, methanesulfonic acid anhydride, paraphenolsulfonic acid anhydride, benzenesulfonic acid anhydride, and paratoluenesulfonic acid anhydride. <6> The optical material composition according to <3>, wherein the acid (b1) comprises at least one selected from the group consisting of 10-camphor sulfonic acid, methanesulfonic acid, and paratoluenesulfonic acid, and the anhydride (b2) comprises at least one selected from the group consisting of 10-camphor sulfonic acid anhydride, methanesulfonic acid anhydride, and paratoluenesulfonic acid anhydride. <7> The optical material composition according to any one of <1> to <6>, further comprising an aliphatic polyisocyanate. <8> The optical material composition according to <7>, wherein the total content of the aliphatic polyisocyanate modified material and the aliphatic polyisocyanate is 80% by mass or more of the total amount of the optical material composition. <9> The optical material composition according to <7> or <8>, wherein the proportion of the aliphatic polyisocyanate modified material in the total of the aliphatic polyisocyanate modified material and the aliphatic polyisocyanate is 60% by mass or less.<10> The optical material composition according to any one of <1> to <9>, wherein the aliphatic polyisocyanate modified material comprises an isocyanurate mononuclear body of aliphatic polyisocyanate. <11> The optical material composition according to any one of <6> to <9>, wherein at least one of the aliphatic polyisocyanate modified material and the aliphatic polyisocyanate comprises a compound obtained from a plant-derived raw material. <12> The optical material composition according to any one of <7> to <11>, wherein the aliphatic polyisocyanate comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dimer acid diisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate, and the aliphatic polyisocyanate modified comprises at least one selected from the group consisting of pentamethylene diisocyanate modified, hexamethylene diisocyanate modified, heptamethylene diisocyanate modified, lysine diisocyanate modified, lysine triisocyanate modified, dimer acid diisocyanate modified, octamethylene diisocyanate modified, and decamethylene diisocyanate modified. <13> A polymerizable composition for optical materials containing a polyisocyanate component (a) which is an optical material composition described in any one of <1> to <12>, and a polythiol component (b) which contains a bifunctional or more thiol compound.<14> The polythiol component (b) is: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-dimercaptomethyl-1,4-dithiane, bis(2-mercaptoethyl) sulfide, and diethylene glycol bis(3-mercaptopropionate) A polymerizable composition for optical materials according to <13>, which is at least one selected from the group consisting of <13>. <15> An optical material comprising a resin which is a cured product of the polymerizable composition for optical materials according to <13> or <14>. <16> A lens comprising a resin which is a cured product of the polymerizable composition for optical materials according to any one of <13> to <15>.

[0007] According to one aspect of the present disclosure, there is a composition for optical materials containing an aliphatic polyisocyanate modified material that can produce an optical material with reduced striations, a polymerizable composition for optical materials containing an aliphatic polyisocyanate modified material that can produce an optical material with reduced striations, an optical material with reduced striations, and a lens with reduced striations.

[0008] In this disclosure, numerical ranges expressed using "~" mean a range that includes the numbers before and after "~" as the lower and upper limits. In this disclosure, the amount of each component in a composition means the total amount of 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 in this disclosure, the upper or lower limit stated in one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Also, in numerical ranges described in this disclosure, the upper or lower limit of that numerical range may be replaced with the values ​​shown in the examples.

[0009] [Composition for Optical Materials] The composition for optical materials of the present disclosure contains an aliphatic polyisocyanate modified product and an acidic compound. As described above, there are cases where it is required to further reduce the vein pattern in an optical material obtained using a composition containing an aliphatic polyisocyanate modified product (for example, see Patent Document 1). According to the composition for optical materials of the present disclosure, it is possible to manufacture an optical material having a reduced vein pattern, which is a composition containing an aliphatic polyisocyanate modified product. Such an effect is considered to be an effect obtained because the composition for optical materials further contains an acidic compound.

[0010] The composition for optical materials of the present disclosure is used as a raw material for manufacturing optical materials. The composition for optical materials of the present disclosure is used, for example, as the isocyanate component (a) in the polymerizable composition for optical materials described later for manufacturing optical materials.

[0011] <Aliphatic Polyisocyanate Modified Product> The composition for optical materials of the present disclosure contains at least one kind of aliphatic polyisocyanate modified product. In the composition for optical materials of the present disclosure, the aliphatic polyisocyanate modified product functions as a monomer for forming the resin contained in the optical material.

[0012] The lower limit of the content of the aliphatic polyisocyanate modified product with respect to the total amount of the composition for optical materials is preferably 20% by mass, 30% by mass, or 40% by mass. The upper limit of the content of the aliphatic polyisocyanate modified product with respect to the total amount of the composition for optical materials is preferably 90% by mass, 70% by mass, or 50% by mass.

[0013] The aliphatic polyisocyanate modified product is a compound obtained by modifying an aliphatic polyisocyanate.

[0014] (Aliphatic polyisocyanates for forming aliphatic polyisocyanate modifiers) Examples of aliphatic polyisocyanates for forming aliphatic polyisocyanate modifiers include trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate methyl ester, lysine diisocyanate, lysine triisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, and bis(isocyanate methyl) Examples include naphthalene, methylisocyanate, bis(isocyanate methyl) sulfide, bis(isocyanate ethyl) sulfide, bis(isocyanate methyl) disulfide, bis(isocyanate ethyl) disulfide, bis(isocyanate methylthio) methane, bis(isocyanate ethylthio) methane, bis(isocyanate ethylthio) ethane, bis(isocyanate methylthio) ethane, diisocyanate dimer acid, octamethylene diisocyanate, decamethylene diisocyanate, and the like. Preferably, the aliphatic polyisocyanates used to form the aliphatic polyisocyanate modifiers are acyclic aliphatic polyisocyanates such as pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dimer acid diisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate. More preferably, the aliphatic polyisocyanates used to form the aliphatic polyisocyanate modifiers are linear aliphatic polyisocyanates such as pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate. These aliphatic polyisocyanates used to form the aliphatic polyisocyanate modifiers can be used alone or in combination of two or more.

[0015] The aliphatic polyisocyanate for forming the aliphatic polyisocyanate modified product preferably contains at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dimer acid diisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate.

[0016] (Aliphatic polyisocyanate modified product) Examples of the aliphatic polyisocyanate modified product include multimers of aliphatic polyisocyanates, biuret modified products of aliphatic polyisocyanates, allophanate modified products of aliphatic polyisocyanates, oxadiazinetrione modified products of aliphatic polyisocyanates, polyol modified products of aliphatic polyisocyanates, and the like.

[0017] Examples of the multimer of aliphatic polyisocyanate include dimers such as uretdione, uretoimine, and carbodiimide, and multimers of trimer or higher such as isocyanurate and iminooxadiazinedione.

[0018] The isocyanurate of aliphatic polyisocyanate can be obtained by reacting aliphatic polyisocyanate in the presence of a known isocyanuration catalyst.

[0019] The biuret modified product of aliphatic polyisocyanate can be obtained by reacting aliphatic polyisocyanate with, for example, water, a tertiary alcohol (such as t-butyl alcohol), a secondary amine (such as dimethylamine, diethylamine, etc.), and then further reacting in the presence of a known biuretization catalyst.

[0020] Allophanate-modified aliphatic polyisocyanates can be obtained by reacting aliphatic polyisocyanates with monoalcohols (monohydric alcohols, e.g., alcohols with 1 to 10 carbon atoms), followed by further reaction in the presence of a known allophanate catalyst. Oxadiazinetrione-modified aliphatic polyisocyanates can be obtained by reacting aliphatic polyisocyanates with carbon dioxide. Imino-oxadianedione-modified aliphatic polyisocyanates can be obtained by further reacting aliphatic polyisocyanates in the presence of a known imino-oxadianedione catalyst. Polyol-modified aliphatic polyisocyanates can be obtained by reacting aliphatic polyisocyanates with alcohols. Suitable alcohols for obtaining aliphatic polyisocyanate modifiers include tertiary alcohols, monoalcohols, and polyhydric alcohols, preferably trihydric alcohols such as glycerin and trimethylolpropane. From the viewpoint of utilizing non-fossil resources, plant-derived alcohols are preferred as the alcohol for obtaining aliphatic polyisocyanate modifiers.

[0021] The aliphatic polyisocyanate modified product preferably contains a polymer of aliphatic polyisocyanate, and more preferably contains an isocyanurate mononuclear of aliphatic polyisocyanate (i.e., an isocyanurate which is a trimer of aliphatic polyisocyanate).

[0022] The aliphatic polyisocyanate modified product may be manufactured by known methods (see, for example, International Publication No. 2015 / 119220) or it may be a commercially available product.

[0023] <Acidic Compounds> The optical material composition of this disclosure contains at least one acidic compound. This suppresses striations in optical materials produced using the optical material composition of this disclosure.

[0024] The content of the acidic compound is preferably 0.01% to 2.0% by mass, more preferably 0.02% to 1.0% by mass, and even more preferably 0.03% to 0.5% by mass, based on the total amount of the optical material composition.

[0025] The acidic compound may be an acid (note: this acid may form a hydrate) or an anhydride of an acid.

[0026] - Compound (b) - The acidic compound preferably contains compound (b), which is at least one compound selected from the group consisting of an acid (b1) having a pKa of less than 10.0 and an anhydride (b2) of an acid having a pKa of less than 10.0.

[0027] Acid (b1) is an acid with a pKa of less than 10.0. Examples of acid (b1) include hydrochloric acid (pKa: -3.7), sulfuric acid (pKa: -3.0), nitric acid (pKa: -1.4), and sulfonic acids with a pKa of less than 10.0. Examples of sulfonic acids with a pKa of less than 10.0 include 10-camphorsulfonic acid (pKa: 1.2), methanesulfonic acid (pKa: -2.6), p-toluenesulfonic acid (pKa: -2.8), vinylsulfonic acid (pKa: -2.7), benzenesulfonic acid (pKa: 0.7), and p-phenolsulfonic acid. Acid (b1) preferably contains a sulfonic acid with a pKa of less than 10.0. Acid (b1) may form a hydrate. An example of the acid (b1) forming the hydrate is benzenesulfonic acid monohydrate (pKa: -2.8).

[0028] Incidentally, some acids may have multiple pKa values. In this disclosure, "pKa" for an acid with multiple pKa values ​​refers to the lowest pKa value among the multiple pKa values. For example, in this disclosure, "an acid with a pKa of less than 10.0" means, in the case of an acid with multiple pKa values, an acid whose lowest pKa value among the multiple pKa values ​​is less than 10.0.

[0029] The pKa of the acid (b1) is less than 10.0, preferably less than 5.0, and more preferably less than 2.0.

[0030] Anhydride (b2) is an anhydride of an acid with a pKa of less than 10.0 (i.e., an anhydride having a structure obtained by dehydration condensation of an acid with a pKa of less than 10.0). Specific examples of acids with a pKa of less than 10.0 for forming anhydride (b2) are the same as the specific examples of acid (b1) described above. Anhydride (b2) preferably includes an anhydride of a sulfonic acid with a pKa of less than 10.0.

[0031] The pKa of the acid for forming the anhydride (b2) is less than 10.0, preferably less than 5.0, and more preferably less than 2.0.

[0032] Compound (b) is, as described above, at least one selected from the group consisting of an acid (b1) with a pKa of less than 10.0 and an anhydride of an acid (b2) with a pKa of less than 10.0, preferably at least one selected from the group consisting of an acid (b1) with a pKa of less than 5.0 and an anhydride of an acid (b2) with a pKa of less than 5.0, and more preferably at least one selected from the group consisting of an acid (b1) with a pKa of less than 2.0 and an anhydride of an acid (b2) with a pKa of less than 2.0.

[0033] A preferred embodiment of compound (b) is one in which the acid (b1) contains a sulfonic acid having a pKa of less than 10.0, and the anhydride (b2) contains an anhydride of sulfonic acid having a pKa of less than 10.0. In this embodiment, the proportion of the total amount of sulfonic acid having a pKa of less than 10.0 and anhydride of sulfonic acid having a pKa of less than 10.0 in compound (b) is preferably 50% to 100% by mass, more preferably 50% to 80% by mass, and even more preferably 80% to 100% by mass.

[0034] A preferred embodiment of compound (b) is one in which the acid (b1) comprises at least one selected from the group consisting of 10-camphorsulfonic acid, methanesulfonic acid, paraphenolsulfonic acid, benzenesulfonic acid, and paratoluenesulfonic acid, and the anhydride (b2) comprises at least one selected from the group consisting of 10-camphorsulfonic acid anhydride, methanesulfonic acid anhydride, paraphenolsulfonic acid anhydride, benzenesulfonic acid anhydride, and paratoluenesulfonic acid anhydride. In this embodiment, the proportion of the total amount of 10-camphorsulfonic acid, methanesulfonic acid, paraphenolsulfonic acid, benzenesulfonic acid, paratoluenesulfonic acid, 10-camphorsulfonic anhydride, methanesulfonic anhydride, paraphenolsulfonic anhydride, benzenesulfonic anhydride, and paratoluenesulfonic anhydride in compound (b) is preferably 50% to 100% by mass, more preferably 50% to 80% by mass, and even more preferably 80% to 100% by mass. Here, each of 10-camphorsulfonic acid and 10-camphorsulfonic anhydride may be a racemic mixture or only one of the enantiomers may be used.

[0035] A more preferred embodiment of compound (b) is one in which the acid (b1) comprises at least one selected from the group consisting of 10-camphorsulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid, and the anhydride (b2) comprises at least one selected from the group consisting of 10-camphorsulfonic acid anhydride, methanesulfonic acid anhydride, and p-toluenesulfonic acid anhydride. In this embodiment, the proportion of the total amount of 10-camphorsulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, 10-camphorsulfonic acid anhydride, methanesulfonic acid anhydride, and p-toluenesulfonic acid anhydride in compound (b) is preferably 50% to 100% by mass, more preferably 50% to 80% by mass, and even more preferably 80% to 100% by mass.

[0036] A more preferred embodiment of compound (b) is one in which the acid (b1) contains 10-camphorsulfonic acid and the anhydride (b2) contains 10-camphorsulfonic anhydride. In this embodiment, the proportion of the total amount of 10-camphorsulfonic acid and 10-camphorsulfonic anhydride in compound (b) is preferably 50% to 100% by mass, more preferably 50% to 80% by mass, and even more preferably 80% to 100% by mass.

[0037] The content of compound (b) is preferably 0.001% to 1% by mass, more preferably 0.01% to 1% by mass, and even more preferably 0.02% to 0.5% by mass, based on the total amount of the optical material composition.

[0038] - Lewis Acid Compounds - Acidic compounds may also preferably contain Lewis acid compounds. If an acidic compound contains Lewis acid compounds, there may be only one type of Lewis acid compound or two or more types.

[0039] 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, etc. 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).

[0040] There are no particular restrictions on the organotin compounds, but examples include: dialkyltin halides such as dibutyltin dichloride and dimethyltin dichloride; dialkyltin dicarboxylates such as dimethyltin diacetate, dibutyltin dioctanoate, and dibutyltin dilaurate; tetrachlorotin; dibutyltin oxide; and others.

[0041] Dialkyltin halides may include monoalkyltin halides and trialkyltin halides. Dialkyltin dicarboxylates may include monoalkyltin tricarboxylates and trialkyltin carboxylates.

[0042] The Lewis acid compound preferably includes a specific organotin compound represented by the following formula (5).

[0043]

[0044] 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 represents an alkyl group having 1 to 11 carbon atoms, and c represents an integer from 1 to 3.

[0045] The compound represented by formula (5) is preferably at least one selected from the group consisting of dimethyltin dichloride, dibutyltin dichloride, and dibutyltin dilaurate.

[0046] The content of Lewis acid compounds (for example, organotin compounds such as the compound represented by formula (5)) is preferably 0.001% to 1% by mass, more preferably 0.01% to 1% by mass, and even more preferably 0.02% to 0.5% by mass.

[0047] <Aliphatic Polyisocyanates> The optical material compositions of this disclosure preferably contain at least one aliphatic polyisocyanate. Specific examples of aliphatic polyisocyanates that may be contained in the optical material compositions of this disclosure are the same as the specific examples of aliphatic polyisocyanates for forming aliphatic polyisocyanate modifiers described above. However, the aliphatic polyisocyanates that may be contained in the optical material compositions of this disclosure and the aliphatic polyisocyanates for forming aliphatic polyisocyanate modifiers may be the same or different.

[0048] Aliphatic polyisocyanates may be manufactured by known methods (see, for example, International Publication No. 2015 / 119220) or may be commercially available.

[0049] When the optical material composition of this disclosure contains an aliphatic polyisocyanate, the total content of the aliphatic polyisocyanate modified product and the aliphatic polyisocyanate is preferably 60% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more, based on the total amount of the optical material composition.

[0050] When the optical material composition of this disclosure contains an aliphatic polyisocyanate, the proportion of aliphatic polyisocyanate in the total of the aliphatic polyisocyanate modified product and the aliphatic polyisocyanate is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more. When the proportion of the aliphatic polyisocyanate modified product is 20% by mass or more, bubbles and distortion are further suppressed in the resulting optical material.

[0051] When the optical material composition of this disclosure contains an aliphatic polyisocyanate, the proportion of aliphatic polyisocyanate in the total of the aliphatic polyisocyanate modified product and the aliphatic polyisocyanate is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less. When the proportion of aliphatic polyisocyanate is 80% by mass or less, the physical properties of the resulting optical material (e.g., transparency, refractive index, heat resistance, strength, etc.) are further improved.

[0052] When the optical material composition of this disclosure contains an aliphatic polyisocyanate, the proportion of the aliphatic polyisocyanate modified material in the total of the aliphatic polyisocyanate modified material and the aliphatic polyisocyanate is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more. When the proportion of the aliphatic polyisocyanate modified material is 20% by mass or more, the physical properties of the resulting optical material (e.g., transparency, refractive index, heat resistance, strength, etc.) are further improved.

[0053] When the optical material composition of this disclosure contains an aliphatic polyisocyanate, the proportion of the aliphatic polyisocyanate modified material to the total of the aliphatic polyisocyanate modified material and the aliphatic polyisocyanate is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less. When the proportion of the aliphatic polyisocyanate modified material is 80% by mass or less, bubbles and distortion are further suppressed in the resulting optical material.

[0054] If the optical material composition of this disclosure contains an aliphatic polyisocyanate, a reaction solution obtained when preparing a modified aliphatic polyisocyanate may be used as a raw material for producing the optical material composition of this disclosure. In this case, the reaction solution includes an aliphatic polyisocyanate and an aliphatic polyisocyanate that is a modified form of the aliphatic polyisocyanate. If the optical material composition of this disclosure contains an aliphatic polyisocyanate, a mixture of the above-described reaction solution and an aliphatic polyisocyanate that is the same as or different from the aliphatic polyisocyanate in the reaction solution may be used as a raw material for producing the optical material composition of this disclosure.

[0055] From the viewpoint of more effectively exhibiting the effects of the optical material compositions of this disclosure, it is preferable that the aliphatic polyisocyanate includes at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dimer acid diisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate.

[0056] From the viewpoint of more effectively exhibiting the effects of the optical material compositions of this disclosure, it is preferable that the aliphatic polyisocyanate modified material includes at least one selected from the group consisting of pentamethylene diisocyanate modified material, hexamethylene diisocyanate modified material, heptamethylene diisocyanate modified material, lysine diisocyanate modified material, lysine triisocyanate modified material, dimer acid diisocyanate modified material, octamethylene diisocyanate modified material, and decamethylene diisocyanate modified material.

[0057] Furthermore, from the viewpoint of utilizing non-fossil resources, it is preferable that in the optical material composition of this disclosure, at least one of the aliphatic polyisocyanate and the aliphatic polyisocyanate modified product contains a compound obtained from plant-derived raw materials. By using the optical material composition of this embodiment, it is easy to obtain a resin with a biomass content of 25% or more, as described later. An example of an aliphatic polyisocyanate obtained from plant-derived raw materials is pentamethylenediisocyanate obtained by phosgenating pentamethylenediamine or a salt thereof obtained by a biochemical method, as described in International Publication No. 2012 / 121291.

[0058] Among the compounds obtained from plant-derived raw materials, aliphatic polyisocyanates obtained from plant-derived raw materials include pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dimer acid diisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate, with pentamethylene diisocyanate being preferred, and 1,5-pentamethylene diisocyanate being particularly preferred.

[0059] Among the compounds obtained from plant-derived raw materials, examples of aliphatic polyisocyanate modified compounds obtained from plant-derived raw materials include pentamethylene diisocyanate modified compounds, hexamethylene diisocyanate modified compounds, heptamethylene diisocyanate modified compounds, lysine diisocyanate modified compounds, lysine triisocyanate modified compounds, dimer acid diisocyanate modified compounds, octamethylene diisocyanate modified compounds, decamethylene diisocyanate modified compounds, and the like. Pentamethylene diisocyanate modified compounds are preferred, and 1,5-pentamethylene diisocyanate modified compounds are particularly preferred.

[0060] <Other Components> The optical material compositions of this disclosure may contain other components besides those described above. There are no particular limitations on the other components, but examples include the components in the polymerizable optical material compositions of this disclosure described later.

[0061] [Polymerizable Composition for Optical Materials] The polymerizable composition for optical materials of this disclosure (hereinafter also simply referred to as "polymerizable composition") contains a polyisocyanate component (a) which is the aforementioned optical material composition of this disclosure, and a polythiol component (b) which contains a thiol compound with two or more functions.

[0062] <Polyisocyanate component (a)> The polymerizable composition of this disclosure contains polyisocyanate component (a). Polyisocyanate component (a) is the optical material composition of this disclosure described above.

[0063] <Polythiol component (b)> The polymerizable composition of this disclosure contains polythiol component (b). Polythiol component (b) contains a thiol compound with two or more functions (hereinafter also referred to as a polythiol compound).

[0064] (Bifunctional or Multifunctional Thiol Compounds) The polythiol compound (i.e., bifunctional or multifunctional thiol compound) in polythiol component (b) may be any compound having two or more thiol groups. For bifunctional or multifunctional thiol compounds, refer to the description in International Publication No. 2015 / 119220.

[0065] The polythiol component (b) is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-dimercaptomethyl-1,4-dithiane, bis(2-mercaptoethyl) sulfide, and diethylene glycol bis(3-mercaptopropionate). It is preferable that the product contains at least one selected from the group consisting of (hereinafter also referred to as "polythiol S"). It is more preferable that polythiol component (b) contains polythiol S as the main component. In this case, polythiol component (b) may contain at least one other component other than polythiol S (for example, other thiol compounds, compounds other than thiol compounds, etc.).

[0066] In this disclosure, "main component" means the component that is present in the largest amount by mass. In this disclosure, the content of the "main component" is preferably 50% by mass or more, preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more.

[0067] More specific embodiments of the polythiol component (b) include, for example: an embodiment mainly comprising pentaerythritol tetrakis(3-mercaptopropionate) (hereinafter also referred to as "polythiol S1"); an embodiment mainly comprising at least one selected from the group consisting 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 (hereinafter also referred to as "polythiol S2"); an embodiment mainly comprising 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (hereinafter also referred to as "polythiol S3"); and an embodiment mainly comprising polythiol S1 and polythiol S2. Embodiments comprising polythiol S2 and polythiol S3 as main components; and so on.

[0068] The polythiol compound in polythiol component (b) preferably includes a polythiol compound obtained from a plant-derived raw material. Examples of polythiol compounds obtained from plant-derived raw materials include a polythiol compound synthesized from epichlorohydrin produced by chlorination and epoxidation of glycerin obtained from a plant-derived raw material (for example, the aforementioned polythiol component S). Examples of glycerin obtained from plant-derived raw materials include glycerin obtained by hydrolysis and / or transesterification of glycerin fatty acid esters contained in vegetable oils such as rapeseed oil, palm oil, castor oil, and olive oil.

[0069] The polythiol compound in polythiol component (b) is easily obtained by curing a polymerizable composition containing a polythiol compound obtained from plant-derived raw materials, thereby yielding a resin with a biomass content of 25% or more, as described later. However, a resin with a biomass content of 25% or more can be produced without using a polymerizable composition containing a polythiol compound obtained from plant-derived raw materials.

[0070] There is no particular limitation on the total content of the polyisocyanate component (a) and the polythiol component (b) in the polymerizable composition of the present disclosure. The total content of the polyisocyanate component (a) and the polythiol component (b) is preferably 80% by mass or more based on the total amount of the polymerizable composition of the present disclosure.

[0071] In the polymerizable composition of the present disclosure, the molar ratio of the total thiol groups in the polythiol component (b) to the total isocyanate groups in the polyisocyanate component (a) is preferably 0.8 to 1.2, more preferably 0.85 to 1.15, and still more preferably 0.9 to 1.1.

[0072] <Polyether-modified silicone compound (c)> The polymerizable composition of the present disclosure may contain a polyether-modified silicone compound (c) represented by the following formula (1) (hereinafter also referred to as "the compound represented by formula (1)").

[0073]

[0074] In formula (1), R １ ~R ８ each independently represents a polyether group represented by formula (2), an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a hydroxy group, or a polysiloxy group. However, at least one of R １ ~R ８ is a polyether group represented by formula (2). In formula (1), m and n each independently represent an integer of 0 or more. In formula (1), when there are a plurality of each of R ２ ~R ５ , the plurality of R ２ ~R ５ may be the same or different from each other. In formula (2), R ２５ represents an alkylene group having 1 to 20 carbon atoms, R ２６ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms, k represents an integer of 1 or more, and * represents a bonding position. In formula (2), when there are a plurality of R ２５ , the plurality of R ２５ may be the same or different from each other.

[0075] In formula (2), R ２５ The alkylene group having 1 to 20 carbon atoms represented by is preferably a linear alkylene group having 1 to 20 carbon atoms (i.e., a straight-chain or branched alkylene group). ２５ Examples of alkylene groups having 1 to 20 carbon atoms that can be represented include methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, t-butylene group, n-pentylene group, isopentylene group, t-pentylene group, n-hexylene group, n-heptylene group, isoheptylene group, n-octylene group, isooctylene group, n-nonylene group, isononylene group, n-decylene group, isodecylene group, n-undecylene group, isoundecylene group, n-dodecylene group, isododecylene group, cyclopentylene group, cyclohexylene group, cycloheptylene group, cyclooctylene group, cyclononylene group, methylcyclopentylene group, methylcyclohexylene group, etc. ２５ The alkylene group having 1 to 20 carbon atoms represented by is more preferably a linear or branched alkylene group having 1 to 8 carbon atoms.

[0076] In equations (1) and (2), R １ ~R ８ or R ２６ The alkyl group having 1 to 20 carbon atoms represented by is preferably a linear alkyl group having 1 to 20 carbon atoms (i.e., a linear or branched alkyl group). １ ~R ８ or R ２６ Examples of C1-C20 alkyl groups represented by include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl group, t-pentyl group, n-hexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-undecyl group, isoundecyl group, n-dodecyl group, isododecyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, methylcyclopentyl group, methylcyclohexyl group, etc. １ ~R ８ or R２６ As the alkyl group having 1 to 20 carbon atoms represented by , more preferably it is a linear or branched alkyl group having 1 to 8 carbon atoms.

[0077] In equations (1) and (2), R １ ~R ８ or R ２６ The alkoxy group having 1 to 20 carbon atoms represented by is preferably a linear alkoxy group having 1 to 20 carbon atoms (i.e., a straight-chain or branched alkoxy group). １ ~R ８ or R ２６ Examples of alkoxy groups having 1 to 20 carbon atoms represented by include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, t-butyloxy group, n-pentyloxy group, isopentyloxy group, t-pentyloxy group, n-hexyloxy group, n-heptyloxy group, isoheptyloxy group, n-octyloxy group, isooctyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, isodecyloxy group, n-undecyloxy group, isoundecyloxy group, n-dodecyloxy group, isododecyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, cyclononyloxy group, methylcyclopentyloxy group, methylcyclohexyloxy group, etc. １ ~R ８ or R ２６ As the alkoxy group having 1 to 20 carbon atoms represented by , more preferably it is a linear or branched alkoxy group having 1 to 8 carbon atoms.

[0078] In formula (2), R ２６ The alkenyl group having 2 to 20 carbon atoms represented by is preferably a linear alkenyl group having 2 to 20 carbon atoms (i.e., a straight-chain or branched alkenyl group). ２６Examples of alkenyl groups having 2 to 20 carbon atoms represented by include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 6-heptenyl group, 7-octenyl group, 8-nonenyl group, 9-dekenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 3-methyl-3-butenyl group, 4-methyl-4-pentenyl group, and 2-cyclohexyl-2-propenyl group. ２６ As the alkenyl group having 2 to 20 carbon atoms represented by , more preferably it is a linear or branched alkenyl group having 2 to 8 carbon atoms.

[0079] In formula (2), R ２６ The alkynyl group having 2 to 20 carbon atoms represented by is preferably a linear alkynyl group having 2 to 20 carbon atoms (i.e., a straight-chain or branched alkynyl group). ２６ Examples of alkynyl groups having 2 to 20 carbon atoms represented by include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 2-methyl-2-propynyl group, 3-methyl-1-butynyl group, 4-pentynyl group, 5-hexynyl group, 6-heptynyl group, 7-octinyl group, 8-noninyl group, 9-decinyl group, etc. ２６ As the alkynyl group having 2 to 20 carbon atoms represented by , more preferably it is a linear or branched alkynyl group having 2 to 8 carbon atoms.

[0080] Examples of compounds represented by formula (1) include: Polyflow KL-100, Polyflow KL-600, Granol 410 (product names of Kyoeisha Chemical Co., Ltd.); BYK-302, BYK-307, BYK-322, BYK-323, BYK-331, BYK-333, BYK-347, BYK-348, BYK-349 (product names of BYK-Chemie Co., Ltd.); KF-351, KF-352, KF-353, KF-354L, KF-355, KF-355A, KF-615A, KF-618 (product names of Shin-Etsu Chemical Co., Ltd.); Examples include SH3746, SH3771, SH8400, SF8410 (product names of Toray Dow Corning Co., Ltd.); TSF4440, TSF4445, TSF4446, TSF4452 (product names of Toshiba Silicone Co., Ltd.); and the like. Particularly preferred examples are Polyflow KL-100 and Polyflow KL-600 (product names of Kyoeisha Chemical Co., Ltd.). Furthermore, from the viewpoint of extending the pot life of the polymerizable composition while improving the balance between the effect of suppressing striations in the resulting molded article and the effect of improving the transparency of the molded article, the compound represented by formula (1) is preferably one or more selected from Polyflow KL-100 and Polyflow KL-600 (product names of Kyoeisha Chemical Co., Ltd.), and more preferably Polyflow KL-100. Here, Polyflow KL-100 includes the compound represented by formula (1A) and the compound represented by formula (1B) described below.

[0081] Furthermore, from the viewpoint of extending the pot life of the polymerizable composition while improving the balance between the effect of suppressing striations in the resulting resin and the effect of improving the transparency of the resin, the compound represented by formula (1) preferably has the R of the polyether group represented by formula (2). ２６ Compounds in which is a hydrogen atom and the R of a polyether group represented by formula (2) ２６ It comprises at least one compound selected from the group consisting of compounds having a linear or branched alkenyl group having 2 to 20 carbon atoms, and more preferably, the R of a polyether group represented by formula (2) ２６ Compounds in which is a hydrogen atom and the R of a polyether group represented by formula (2) ２６It comprises at least one compound selected from the group consisting of compounds having a linear or branched alkenyl group having 2 to 8 carbon atoms, and more preferably at least one compound selected from the group consisting of compounds represented by the following formula (1A) and compounds represented by the following formula (1B).

[0082]

[0083] In equation (1A), a + c is between 1 and 100, b is between 1 and 100, d is between 10 and 1000, and e is between 1 and 100. In equation (1B), f + h is between 1 and 100, and g is between 1 and 100.

[0084] From the viewpoint of further suppressing striations in the resulting resin, in formula (1A), a + c is preferably 5 to 50. From a similar viewpoint, in formula (1A), b is preferably 5 to 50. From a similar viewpoint, in formula (1A), e is preferably 5 to 50. From a similar viewpoint, the molecular weight of the compound represented by formula (1A) is preferably 100 to 10000, and more preferably 1000 to 5000.

[0085] From the viewpoint of further suppressing striations in the resulting resin, f + h in formula (1B) is preferably 1 to 20. From a similar viewpoint, g in formula (1B) is preferably 1 to 10. From a similar viewpoint, the molecular weight of the compound represented by formula (1B) is preferably 100 to 10000, and more preferably 500 to 5000.

[0086] When the polyether-modified silicone compound (c) contains both the compound represented by formula (1A) and the compound represented by formula (1B), from the viewpoint of further suppressing striations in the resulting resin, the mass ratio of the compound represented by formula (1A) to the total mass of the compounds represented by formula (1A) and formula (1B) is preferably 50% to 90%, and more preferably 60% to 80%.

[0087] From the viewpoint of further suppressing striations in the resulting resin, the content of the polyether-modified silicone compound (c) (i.e., the compound represented by formula (1)) is preferably 0.001% to 5% by mass, more preferably 0.005% to 3% by mass, and even more preferably 0.01% to 2% by mass, based on the total amount of the polymerizable composition of the present disclosure.

[0088] <Polymerization Catalyst> The polymerizable composition of this disclosure may contain at least one polymerization catalyst. The polymerization catalyst functions, for example, as a catalyst for the polymerization reaction when curing the polymerizable composition of this disclosure to obtain a resin. Known polymerization catalysts such as organometallic compounds, amines, and quaternary onium salts can be used as polymerization catalysts. Examples of organometallic compounds include compounds containing tin, zinc, copper, etc. Specific examples of organometallic compounds include: organotin compounds such as tin acetate, tin octoate, tin oleate, tin laurate, dibutyltin diacetate, dimethyltin dilaurate, dibutyltin dilaurate, dibutyltin dimercaptide, dibutyltin maleate, dibutyltin dineodecanoate, dioctyltin dimercaptide, dioctyltin dilaurate, dimethyltin dichloride, and dibutyltin dichloride; organozinc compounds such as zinc naphthenate; and organocopper compounds such as copper octenoate.

[0089] Examples of amines include: triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, trioctylamine, triallylamine, N,N-dimethylbenzylamine, N-methylmorpholine, N,N-dimethylcyclohexylamine, dimethyldipropylenetriamine, pentamethyldiethylenetriamine, bis(2-dimethylaminoethyl) ether, N-methylmorpholine, N,N'-dimethylpiperazine, triethylenediamine, N,N,N',N'-tetramethylethylenediamine, bicyclooctanediamine (DABCO), 2-methylpyrazine, pyridine, α-picoline, β-picoline, γ-picoline, 2,6-lutidine, 3,5-lutidine, 2,4,6-trimethylpyridine, 3-chlorpyridine, and other tertiary amines; Examples include imidazoles such as imidazole, 1,2-dimethylimidazole, N-benzyl-2-methylimidazole, and 2-ethyl-4-imidazole; and pyrazoles such as pyrazole and 3,5-dimethylpyrazole.

[0090] Examples of quaternary ammonium salts include quaternary ammonium salts and phosphonium salts. Examples of quaternary ammonium salts include tetrabutylammonium bromide and tetraethylammonium hydroxide. Examples of phosphonium salts include tetramethylphosphonium chloride, tetraethylphosphonium chloride, tetrapropylphosphonium chloride, tetrabutylphosphonium chloride, tetrahexylphosphonium chloride, tetraoctylphosphonium chloride, ethyltriphenylphosphonium chloride, tetraphenylphosphonium chloride, butyltriphenylphosphonium chloride, benzyltriphenylphosphonium chloride, methoxymethyltriphenylphosphonium chloride, tetramethylphosphonium bromide, tetraethylphosphonium bromide, tetrapropylphosphonium bromide, tetrabutylphosphonium bromide, and tetrahexylphosphonium bromide. Examples of phosphonium salt compounds include tetraoctylphosphonium bromide, ethyltriphenylphosphonium bromide, tetraphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium bromide, methoxymethyltriphenylphosphonium bromide, ethyltriphenylphosphonium acetate, ethyltriphenylphosphonium iodide, tetraethylphosphonium hydroxide, tetrabutylphosphonium hydroxide, tetraphenylphosphonium tetrakis(4-methylphenyl) borate, tetraphenylphosphonium tetraphenyl borate, and tetrabutylphosphonium-o,o-diethylphosphorodithioate.

[0091] From the viewpoint of reducing environmental impact, a non-metallic catalyst may be used as the polymerization catalyst. Examples of non-metallic catalysts include amines (particularly preferably imidazoles), phosphonium salts, and acids. These polymerization catalysts themselves may be compounds derived from plants.

[0092] The polymerizable composition of this disclosure contains a polymerization catalyst, preferably 0.001% to 10% by mass, more preferably 0.001% to 5% by mass, even more preferably 0.005% to 3% by mass, and even more preferably 0.01% to 2% by mass, based on the total amount of the polymerizable composition.

[0093] <Internal Release Agent> The polymerizable composition of this disclosure may contain at least one internal release agent. As the internal release agent, for example, an acidic phosphate ester can be used. A specific example of an acidic phosphate ester is a compound represented by the following formula (P1).

[0094]

[0095] In formula (P1), m represents 1 or 2, n represents an integer from 0 to 18, and R １ R represents an alkyl group having 1 to 20 carbon atoms. ２ and R ３ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group. The number of carbon atoms in the parentheses with the subscript "m" is preferably 4 to 20.

[0096] R in equation (P1) １ Examples include: organic residues derived from linear aliphatic compounds such as methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tetradecane, and hexadecane; and organic residues derived from branched aliphatic compounds such as 2-methylpropane, 2-methylbutane, 2-methylpentane, 3-methylpentane, 3-ethylpentane, 2-methylhexane, 3-methylhexane, 3-ethylhexane, 2-methylheptane, 3-methylheptane, 4-methylheptane, 3-ethylheptane, 4-ethylheptane, 4-propylheptane, 2-methyloctane, 3-methyloctane, 4-methyloctane, 3-ethyloctane, 4-ethyloctane, and 4-propyloctane. Examples include organic residues derived from alicyclic compounds such as cyclopentane, cyclohexane, 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, and 1,4-dimethylcyclohexane.

[0097] Commercially available acidic phosphate esters include ZelecUN from STEPAN, the JP series from Johoku Chemical Industry, the Phosphanol series from Toho Chemical Industry, and the AP and DP series from Daihachi Chemical Industry. Furthermore, from the viewpoint of solubility in polymerizable compositions and transparency of the resin, ZelecUN and JP-506H are preferred, with JP-506H being particularly preferred.

[0098] If the polymerizable composition of this disclosure contains an acidic phosphate ester as an internal release agent, the content of the acidic phosphate ester as an internal release agent is preferably 0.001% to 10% by mass, more preferably 0.001% to 5% by mass, even more preferably 0.005% to 3% by mass, and even more preferably 0.01% to 2% by mass, based on the total amount of the polymerizable composition.

[0099] <UV absorbers> The polymerizable composition of this disclosure may contain at least one UV absorber.Examples of UV absorbers include: benzophenone-based UV absorbers such as 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, and 2-hydroxy-4-acryloyloxy-2',4'-dichlorobenzophenone; 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-(2-hydroxy-3-tridecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, and 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy] Triazine-based UV absorbers such as -2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bis-butyloxyphenyl)-1,3,5-triazine, and 2-(2-hydroxy-4-[1-octyloxycarbonylethoxy]phenyl)-4,6-bis(4-phenylphenyl)-1,3,5-triazine; 2-(2H-benzotriazole-2-yl)-4-methylphenol, 2-(2H-benzotriazole-2-yl)-4-tert-octylphenol, 2-(2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol, 2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl-6- Benzotriazole-based ultraviolet absorbers such as tert-butylphenol, 2-(5-chloro-2H-benzotriazole-2-yl)-2,4-tert-butylphenol, 2,2'-methylenebis[6-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], and 2-(2H-benzotriazole-2-yl)-4-methyl-6-(3,4,5,6-tetrahydrophthalimidylmethyl)phenol are examples.

[0100] The amount of ultraviolet absorber in the polymerizable composition of this disclosure is preferably 0.001% to 10% by mass, more preferably 0.01% to 5% by mass, and even more preferably 0.1% to 5% by mass, based on the total amount of the polymerizable composition.

[0101] One preferred embodiment of the polymerizable composition of the present disclosure is a polymerizable composition containing an ultraviolet absorber, a polymerization catalyst, and an acidic phosphate ester as an internal release agent. In this case, the preferred range of content of each component is as described above, for example, the content of the ultraviolet absorber is 0.1% to 5% by mass of the total amount of the polymerizable composition for optical materials, the content of the polymerization catalyst is 0.001% to 5% by mass of the total amount of the polymerizable composition for optical materials, and the content of the acidic phosphate ester as an internal release agent is 0.001% to 5% by mass of the total amount of the polymerizable composition for optical materials.

[0102] <Other Components> The polymerizable compositions of this disclosure may contain other components besides those described above. Examples of other components include light stabilizers, antioxidants, color inhibitors, dyes, bluing agents, resin modifiers, and the like.

[0103] Hindered amine compounds can be used as light stabilizers. Examples of hindered amine compounds include: Lowilite 76 and Lowilite 92 from Chemtura; Tinuvin 123, Tinuvin 144, Tinuvin 292, Tinuvin 765, and Tinuvin 770DF from BASF; Adeka Stab LA-52 and LA-72 from ADEKA; and JF-90 and JF-95 from Johoku Chemical Industry Co., Ltd.

[0104] Examples of bluing agents include those that have an absorption band in the orange to yellow wavelength range within the visible light spectrum and have the function of adjusting the hue of optical materials. More specifically, bluing agents include substances that exhibit blue to purple colors.

[0105] Other components include polyisocyanates other than polyisocyanate component (a), such as alicyclic polyisocyanates, aromatic polyisocyanates, and heterocyclic polyisocyanates. For information on alicyclic polyisocyanates, aromatic polyisocyanates, and heterocyclic polyisocyanates, please refer to International Publication No. 2015 / 119220.

[0106] <Method for Producing Polymerizable Composition> 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 components (raw materials) are mixed; all of the raw materials may be added to the container at once and mixed, or the raw materials 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 (i.e., polyisocyanate component (a) and polythiol component (b)) may polymerize to form a prepolymer.

[0107] A preferred embodiment of the polymerizable composition of the present disclosure (hereinafter referred to as "Method A") will be described below. Method A is a preferred method for producing a polymerizable composition containing an ultraviolet absorber, a polymerization catalyst, and an acidic phosphate ester. Method A includes the steps of: obtaining solution A1 by adding a polyether-modified silicone compound (c) and an acidic phosphate ester to an aliphatic polyisocyanate; obtaining solution A2 by dissolving an acidic compound, an ultraviolet absorber, and a polymerization catalyst in the aliphatic polyisocyanate; obtaining solution A2X as a polyisocyanate component (a) (i.e., the optical material composition of the present disclosure) by dissolving an aliphatic polyisocyanate modifier in solution A2; obtaining solution A3 by mixing solution A1 and solution A2X; and obtaining the polymerizable composition of the present disclosure by adding a polythiol component (b) containing a polythiol compound to solution A3. According to manufacturing method A, the polymerizable composition of the present disclosure can be manufactured while suppressing the formation of gel-like insoluble matter.

[0108] Furthermore, a method for producing the optical material composition of the present disclosure includes, for example, the steps of: dissolving an acidic compound, an ultraviolet absorber, and a polymerization catalyst in an aliphatic polyisocyanate to obtain solution A2; and dissolving an aliphatic polyisocyanate modified product in solution A2 to obtain solution A2X as polyisocyanate component (a) (i.e., the optical material composition of the present disclosure).

[0109] [Optical Materials] The optical materials of this disclosure include a resin (hereinafter also referred to as "the resin in this disclosure") which is a cured product of the polymerizable composition of this disclosure described above. The resin in this disclosure can be produced by curing the polymerizable composition of this disclosure described above, or more specifically, by polymerizing and curing the monomers in the polymerizable composition of this disclosure. An example of a method for producing the resin is casting polymerization, which will be described later.

[0110] 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 provided on the resin of this disclosure, and so on.

[0111] 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.

[0112] A method for polymerizing monomers in the polymerizable composition of the present disclosure (i.e., a method for curing the polymerizable composition of the present disclosure) is, for example, casting polymerization. By casting polymerization, a molded article of the resin in the optical material of the present disclosure (i.e., a cured product of the polymerizable composition of the present disclosure) can be obtained.

[0113] In casting polymerization, first, a polymerizable composition according to an example of the present disclosure is injected between a pair of 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 molds are polymerized to cure the composition between the molds and obtain a cured product. Then, the cured product is removed from the molds to obtain a cured product. The polymerization of the monomers may also be carried out by heating the polymerizable composition of the present 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, etc.

[0114] 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. Examples of polymerization times include 1 hour to 200 hours and 1 hour to 80 hours.

[0115] The resin in this disclosure may be obtained by polymerizing monomers and then subjecting them to treatments such as annealing. Examples of annealing temperatures include 50°C to 150°C, 90°C to 140°C, 100°C to 130°C, and so on.

[0116] (Preferred performance of the resin) The glass transition temperature (Tg) of the resin in this disclosure is preferably 60°C or higher, more preferably 70°C or higher, and even more preferably 80°C or higher. The Tg of the resin may be 130°C or lower, 120°C or lower, or 110°C or lower.

[0117] The refractive index (ne) of the resin in this disclosure is preferably 1.500 or higher, more preferably 1.540 or higher, and even more preferably 1.590 or higher. There is no particular upper limit to the refractive index (ne), but the upper limit is, for example, 1.750.

[0118] The Abbe number of the resin in this disclosure is preferably 28 or higher, more preferably 30 or higher. There is no particular upper limit to the Abbe number, but the upper limit is, for example, 50, preferably 45.

[0119] The specific gravity d of the resin in this disclosure is preferably 1.10 or higher, more preferably 1.20 or higher. There is no particular upper limit to the specific gravity d, but the upper limit is, for example, 1.50, preferably 1.40.

[0120] The yellow index (YI) of the resin in this disclosure is preferably 2.10 or less, more preferably 2.00 or less, even more preferably 1.90 or less, and even more preferably 1.80 or less. There is no particular lower limit to the YI, but the lower limit is, for example, 1.30, and preferably 1.50.

[0121] The haze of the resin in this disclosure is preferably 0.30 or less, more preferably 0.25 or less, and even more preferably 0.20 or less. There is no particular lower limit to the haze, but the lower limit is, for example, 0.05, and preferably 0.10.

[0122] (Biomass content of resin) From the viewpoint of utilizing non-fossil resources, the biomass content of the resin in this disclosure is preferably 25% or more, more preferably 30% or more, and even more preferably 50% or more.

[0123] In this disclosure, the biomass percentage is determined by a carbon-based calculation method and is calculated based on the following formula: Biomass percentage (%) = {(Number of plant-derived carbons) / (Number of plant-derived carbons + Number of petroleum-derived carbons)} × 100 Here, plant-derived carbons are １４ C means petroleum-derived carbon, １４ Carbon atoms other than C (mostly １２ C) means that "the number of carbon atoms derived from plants + the number of carbon atoms derived from petroleum" represents the total number of carbon atoms in the substance being measured.

[0124] In this disclosure, the biomass content (%) of the resin is determined in accordance with the ASTM (United States Standard Test Method) D6866-21 (Standard Test Method for Determining the Biobased Content of Natural Range Materials Using Radiocarbon and Isotope Ratio Mass Spectrometry Analysis), by burning the resin as a measurement sample to obtain CO2. ２ It generates CO ２ Regarding this, accelerator mass spectrometry (AMS) was used to determine: １４ Content of C and １４ It is calculated by measuring the content of carbon atoms other than C.

[0125] [Lenses] The lenses of this disclosure are an example of the optical materials of this disclosure and include the resins of this disclosure described above (i.e., resins that are cured products of the polymerizable compositions of this disclosure). The lenses of this disclosure may be manufactured, for example, by casting polymerization as described above.

[0126] The lens 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.

[0127] Examples of lenses in this disclosure include eyeglass lenses, camera lenses, polarized lenses, and the like. Hereinafter, an example of an eyeglass lens in this disclosure will be described. An eyeglass lens includes a resin in this disclosure that is molded into a desired lens shape. Preferably, the eyeglass lens further includes a coating layer provided on one or both sides of the resin.

[0128] 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 product, the same coating layer may be applied to each surface, or different coating layers may be applied to each surface.

[0129] The components of the coating layer can be appropriately selected depending on the purpose. Examples of coating layer components include 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, etc.

[0130] 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.

[0131] 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.

[0132] [Example 1] <Preparation of Solution A1> Solution A1 was prepared by mixing and dissolving 12.00 parts by mass of 1,5-pentamethylene diisocyanate (hereinafter also referred to as "PDI") as an aliphatic polyisocyanate ("Stabio PDI" manufactured by Mitsui Chemicals, Inc.; biomass content 70%), 0.10 parts by mass of Polyflow KL-100 (manufactured by Kyoeisha Chemical Co., Ltd.) (hereinafter also referred to as "KL-100") as a polyether-modified silicone compound (c), and 0.20 parts by mass of JP-506H (acidic phosphate ester manufactured by Johoku Chemical Industry Co., Ltd.) as an internal mold release agent at 20°C. Here, KL-100 is the polyether-modified silicone compound (c) represented by the above formula (1), and more specifically, it includes the compound represented by the above formula (1A) and the compound represented by the above formula (1B).

[0133] <Preparation of Solution A2X as an Optical Material Composition> Solution A2 was obtained by mixing and dissolving the following at 20°C: 20.45 parts by mass of PDI (Stabio PDI, manufactured by Mitsui Chemicals, Inc.; biomass content 70%) as an aliphatic polyisocyanate, 0.05 parts by mass of 10-camphorsulfonic acid as an acidic compound, 0.60 parts by mass of 2-(2H-benzotriazole-2-yl)-4-tert-octylphenol as an ultraviolet absorber, 0.60 parts by mass of 2-(2H-benzotriazole-2-yl)-4-methyl-6-(3,4,5,6-tetrahydrophthalimidylmethyl)phenol as an ultraviolet absorber, and 0.03 parts by mass of dimethyltin dichloride (hereinafter also referred to as "DMC") as a polymerization catalyst. To the obtained solution A2, 28.15 parts by mass of isocyanurate 1,5-pentamethylene diisocyanate (hereinafter also referred to as "PDInurate") ("Stabio D-370N" manufactured by Mitsui Chemicals, Inc.; biomass content 70%) was added and mixed and dissolved at 20°C to obtain solution A2X as polyisocyanate component (a) (i.e., composition for optical materials).

[0134] <Preparation of Polymerizable Composition for Optical Materials> To the solution A2X obtained above as an optical material composition, the previously prepared solution A1 (3.08 parts by mass) was added and mixed and dissolved at 20°C to obtain solution A3 containing a polyisocyanate component (a) and a polyether-modified silicone compound (c). The obtained solution A3 was degassed under a reduced pressure of 600 Pa until no more foaming was observed. To the degassed solution A3, 14.65 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) (i.e., the aforementioned polythiol S1) was added as polythiol component (b), and 33.05 parts by mass of polythiol containing at least one selected from the group consisting 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 (i.e., the aforementioned polythiol S2) was added, and the mixture was mixed and dissolved at 20°C. As a result, a polymerizable composition for optical materials containing polyisocyanate component (a) and polythiol component (b) was obtained.

[0135] <Preparation of Resin Molded Articles> The polymerizable composition for optical materials obtained above was thoroughly degassed under a reduced pressure of 600 Pa until no foaming was observed. The degassed polymerizable composition for optical materials was filtered through a 1 μm filter and injected between a pair of glass molds fixed with tape. Next, the pair of glass molds into which the polymerizable composition for optical materials was injected was placed in an oven, and the oven temperature was gradually raised from 20°C to 120°C over 20 hours. Through the above process, the monomers in the degassed polymerizable composition for optical materials (i.e., polyisocyanate component (a) and polythiol composition (b)) were polymerized, and a resin molded article (i.e., a resin molded article which is a cured product of the polymerizable composition for optical materials) was formed between the pair of glass molds. Subsequently, the oven was cooled, and after cooling, the pair of glass molds was removed from the oven, and then the resin molded article was removed from the pair of glass molds to obtain the resin molded article. The resulting resin molded body was annealed at 120°C for 1 hour to obtain a lens containing resin.

[0136] <Evaluation> The following evaluation was performed on the resin molded product (i.e., lens) after the annealing described above. The results are shown in Table 1.

[0137] - Release properties In the production of the above-mentioned resin molded body, the release properties when removing the resin molded body from a pair of glass molds were evaluated according to the following evaluation criteria. In the following evaluation criteria, rank A represents the best release properties. - Evaluation criteria for release properties - A: The resin molded body naturally peeled off the pair of glass molds by cooling the oven to room temperature. B: The resin molded body could be peeled off the pair of glass molds by inserting a wedge into the edge of the resin molded body. C: The glass mold cracked or the glass peeled off and stuck to the resin during release. Alternatively, the resin could not be released from the glass mold.

[0138] Except for appropriately selecting the shape and size of a pair of heat-resistant glass molds, a test specimen measuring 10 mm in length, 10 mm in width, and 2.5 mm in thickness was obtained using the same procedure as described in <Preparation of Resin Molded Body> above. The glass transition temperature Tg of the above sample was measured using the TMA penetration method (50 g load, 0.5 mm diameter pin tip, heating rate 10 °C / min) with a Shimadzu TMA-60 thermomechanical analyzer, and this was used as an indicator of heat resistance. The higher the glass transition temperature Tg, the better the heat resistance.

[0139] - Specific gravity: The specific gravity of the resin molded body was measured at 20°C using the Archimedes method.

[0140] • Optical properties (refractive index (n) ｅ ) and Abbe number (ν ｅ Except for appropriately selecting the shape and size of a pair of glass molds, a test specimen measuring 10 mm in length, 10 mm in width, and 2.5 mm in thickness was obtained by the same procedure as in the above-described procedure for "Preparation of Resin Molded Body". The refractive index of the obtained test specimen was measured at wavelengths of 546.1 nm (mercury e line), 480.0 nm (Cd F' line), and 643.9 nm (Cd C' line) using a Shimadzu KPR-30 Pulfrich refractometer, and based on these measurement results, the refractive index (n ｅ ) and Abbe number (ν ｅ ) were calculated for each.

[0141] • 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 piece 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 piece was measured using a Konica Minolta CM-5 spectrophotometer to determine the YI (Yellow Index; yellowness), a ＊ , and b ＊ This was sought. The smaller the YI value, the better the hue of the lens.

[0142] Except for appropriately selecting the shape and size of the pair of glass molds, a disc-shaped test piece 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 haze value of the resin was measured using a haze meter (model number: NDH 2000) manufactured by Nippon Denshoku Industries, Ltd. The smaller the haze value, the better the transparency as a lens.

[0143] - Streaks Ten semi-finished lenses (hereinafter simply referred to as "lenses") with a thickness of 10 mm were fabricated using the same procedure as in the above <Fabrication of Resin Molded Body>, except that a pair of glass molds with a 6-base curve were used. Each of the 10 obtained lenses was visually inspected using a high-pressure mercury lamp (Optical Module X, manufactured by Ushio Inc.) to check for the presence or absence of striations. Based on the results of the 10 lenses, striations were evaluated according to the following evaluation criteria. In the following evaluation criteria, A has more suppressed striations than B.

[0144] - Evaluation Criteria for Plaque - A: Out of 10 lenses, 9 or more lenses showed no plaque. B: Out of 10 lenses, 8 or fewer lenses showed no plaque.

[0145] [Example 2] The same procedure as in Example 1 was followed in the preparation of the polymerizable composition, except that the amount of 10-camphorsulfonic acid as the acidic compound was changed as shown in Table 1. The results are shown in Table 1. Note that a blank space in the "Acidic Compound" column of Table 1 means that the corresponding component is not contained.

[0146] [Examples 3-5] The same procedure as in Example 1 was followed in the preparation of polymerizable compositions, except that the type and amount of acidic compound were changed as shown in Table 1. The results are shown in Table 1.

[0147] [Comparative Example 2] The same procedure as in Example 1 was followed in the preparation of the polymerizable composition, except that 10-camphorsulfonic acid was not used as the acidic compound.

[0148]

[0149] As shown in Table 1, the lenses of Examples 1 to 5, which were made using an optical material composition (i.e., polyisocyanate component (a)) containing an aliphatic polyisocyanate modifier and an acidic compound, showed suppressed striations compared to the lens of Comparative Example 1, which was made using an optical material composition that did not contain an acidic compound.

[0150] The biomass content of the resins in Examples 1 to 5 was measured using the method described above. As a result, the biomass content of the resins in Examples 1 to 5 was 45% in all cases.

[0151] The disclosure of Japanese Patent Application No. 2024-196890, filed on November 11, 2024, is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein 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

1. A composition for optical materials containing an aliphatic polyisocyanate modified material and an acidic compound.

2. The optical material composition according to claim 1, wherein the content of the aliphatic polyisocyanate modified material is 50% by mass or more of the total amount of the optical material composition.

3. The optical material composition according to claim 1, wherein the acidic compound comprises a compound (b) selected from the group consisting of an acid (b1) having a pKa of less than 10.0 and an anhydride (b2) of an acid having a pKa of less than 10.

0.

4. The optical material composition according to claim 3, wherein the acid (b1) comprises a sulfonic acid having a pKa of less than 10.0, and the anhydride (b2) comprises an anhydride of a sulfonic acid having a pKa of less than 10.

0.

5. The optical material composition according to claim 3, wherein the acid (b1) comprises at least one selected from the group consisting of 10-camphor sulfonic acid, methanesulfonic acid, paraphenolsulfonic acid, benzenesulfonic acid, and paratoluenesulfonic acid, and the anhydride (b2) comprises at least one selected from the group consisting of 10-camphor sulfonic acid anhydride, methanesulfonic acid anhydride, paraphenolsulfonic acid anhydride, benzenesulfonic acid anhydride, and paratoluenesulfonic acid anhydride.

6. The optical material composition according to claim 3, wherein the acid (b1) comprises at least one selected from the group consisting of 10-camphorsulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid, and the anhydride (b2) comprises at least one selected from the group consisting of 10-camphorsulfonic anhydride, methanesulfonic anhydride, and p-toluenesulfonic anhydride.

7. The optical material composition according to claim 1, further comprising an aliphatic polyisocyanate.

8. The optical material composition according to claim 7, wherein the total content of the aliphatic polyisocyanate modified product and the aliphatic polyisocyanate is 80% by mass or more of the total amount of the optical material composition.

9. The optical material composition according to claim 7, wherein the proportion of the aliphatic polyisocyanate modified material in the total of the aliphatic polyisocyanate modified material and the aliphatic polyisocyanate is 60% by mass or less.

10. The optical material composition according to claim 1, wherein the aliphatic polyisocyanate modified body comprises an isocyanurate mononucleus of aliphatic polyisocyanate.

11. The optical material composition according to claim 7, wherein at least one of the aliphatic polyisocyanate modified product and the aliphatic polyisocyanate comprises a compound obtained from a plant-derived raw material.

12. The optical material composition according to claim 7, wherein the aliphatic polyisocyanate comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dimer acid diisocyanate, octamethylene diisocyanate, and decamethylene diisocyanate, and the aliphatic polyisocyanate modified comprises at least one selected from the group consisting of pentamethylene diisocyanate modified, hexamethylene diisocyanate modified, heptamethylene diisocyanate modified, lysine diisocyanate modified, lysine triisocyanate modified, dimer acid diisocyanate modified, octamethylene diisocyanate modified, and decamethylene diisocyanate modified.

13. A polymerizable composition for optical materials comprising: a polyisocyanate component (a) which is an optical material composition according to any one of claims 1 to 12; and a polythiol component (b) which contains a bifunctional or more thiol compound.

14. The polythiol component (b) is: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-dimercaptomethyl-1,4-dithiane, bis(2-mercaptoethyl) sulfide, and diethylene glycol bis(3-mercaptopropionate). The polymerizable composition for optical materials according to claim 13, which is at least one selected from the group consisting of the following.

15. An optical material comprising a resin which is a cured product of the polymerizable composition for optical materials described in claim 13.

16. A lens comprising a resin which is a cured product of the polymerizable composition for optical materials described in claim 13.

Images