Method for manufacturing optical components

Abstract

The present invention provides a manufacturing method for optical components to which functional compounds are applied, thereby enabling the optical components to exhibit their functions more effectively. [Solution] The method for manufacturing an optical component includes a first polymerization step of reacting a hydroxyl group-containing polyether compound (A) and a bifunctional or more iso(thio)cyanate compound (B) to obtain a prepolymer, and a second polymerization step of mixing the obtained prepolymer with a bifunctional or more active hydrogen compound (C) and a catalyst (D), and polymerizing and curing it.

Description

Technical Field

[0001] The present invention relates to a method for manufacturing an optical member.

Background Art

[0002] Plastic lenses have rapidly spread as optical materials for eyeglass lenses, camera lenses, etc. because they are lightweight, difficult to break, and can be dyed. To date, lens molded bodies using various plastic materials have been developed and used.

[0003] Typical examples include allyl resins obtained from diethylene glycol bisallyl carbonate or diallyl isophthalate, (meth)acrylic resins obtained from (meth)acrylates, and polythiourethane resins obtained from isocyanates and thiols.

[0004] In recent years, high-functional plastic lenses with various functions have been developed by applying functional compounds to the above plastic materials. For example, lenses that block light of harmful wavelengths, lenses with suppressed surface scratches, lenses with suppressed fogging on the lens surface caused by temperature differences, and plastic lenses with photochromic performance are known. Among them, by using a plastic lens with photochromic performance for eyeglasses, it can function as ordinary transparent-colored eyeglasses indoors, and outdoors, the lens can be colored gray, brown, etc. in response to sunlight (ultraviolet rays), and the function of protecting the eyes from glare can be obtained. Also, this pair of glasses does not require putting on and taking off glasses indoors and outdoors like sunglasses, and it is possible to use one pair of glasses for both indoor and outdoor use.

[0005] On the other hand, when applying a functional compound to a plastic material, it is important that the function of the functional compound is effectively exerted. For example, a plastic lens obtained using a plastic material to which a photochromic compound is applied is required to have fast responsiveness in coloring and decoloring and to exhibit good coloring performance.

[0006] Therefore, Patent Document 1 discloses that by using specific aliphatic and alicyclic isocyanates, urethane resin-based optical materials or thiourethane resin-based optical materials and plastic lenses containing photochromic compounds can be obtained without causing a decrease in the performance of the photochromic compounds. Furthermore, Patent Document 2 discloses that by using an optical material containing a specific polyol compound, it is possible to obtain a polyurethane-based optical material or a polythiourethane-based optical material containing a photochromic compound that exhibits excellent photochromic performance without degrading the performance of the photochromic compound, and also has excellent physical properties such as mechanical strength.

[0007] Furthermore, polyloxasan is used in photochromic compositions for photochromic eyeglasses. For example, Patent Document 3 discloses a curable resin composition that incorporates the property of polyloxasan in which cyclic molecules move within the axial molecules within the cured polymer. It also discloses that by using polypsiminoxasan monomer (prepolymer) obtained in a preceding step instead of polyloxasan in the manufacturing process of the curable resin composition, the manufacturing process can be simplified and productivity can be improved. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] International Publication No. 2014 / 002844 [Patent Document 2] International Publication No. 2015 / 115648 [Patent Document 3] International Publication No. 2020 / 032056 [Overview of the project] [Problems that the invention aims to solve]

[0009] The present inventors have found that there is room for improvement in the color intensity of conventional optical materials to which photochromic compounds, such as those described in Patent Documents 1 and 2, are applied. Furthermore, the technology disclosed in Patent Document 3 improves productivity while obtaining the properties of polyloxane monomers, and does not consider any improvement in optical properties.

[0010] In light of these circumstances, the present invention aims to enable optical components to which functional compounds are applied to exhibit their functions more effectively. [Means for solving the problem]

[0011] The inventors of this invention conducted diligent research to solve the above problems and, as a result, discovered that it is effective to manufacture optical components using a new manufacturing method, and thus completed the present invention.

[0012] In other words, the present invention can be described as follows.

[0013] [1] A first polymerization step in which a hydroxyl group-containing polyether compound (A) and a bifunctional or more iso(thio)cyanate compound (B) are reacted to obtain a prepolymer, A second polymerization step involves mixing the obtained prepolymer with a bifunctional or more active hydrogen compound (C) and a catalyst (D), and polymerizing and curing the mixture. A method for manufacturing optical components, including [the specified component]. [2] The method for producing an optical component according to [1], wherein in the first polymerization step, a hydroxyl group-containing polyether compound (A) and a bifunctional or more iso(thio)cyanate compound (B) are mixed and reacted by heating to a temperature of 20°C or higher and 150°C or lower. [3] A method for producing an optical component according to either [1] or [2], wherein, in the first polymerization step, when the total amount of the hydroxyl group-containing polyether compound (A) and the bifunctional or more iso(thio)cyanate compound (B) is 100% by mass, the amount of the hydroxyl group-containing polyether compound (A) is 0.5% by mass or more and 50% by mass or less. [4] A method for producing an optical component according to any one of [1] to [3], wherein in the first polymerization step, the ratio (hydroxyl group / iso(thio)cyanate group) of the number of hydroxyl group equivalents of the hydroxyl group-containing polyether compound (A) to the number of iso(thio)cyanate group equivalents of the bifunctional or more iso(thio)cyanate compound (B) is 10 to 100,000. [5] A method for producing an optical component according to any one of [1] to [4], wherein the number average molecular weight of the hydroxyl group-containing polyether compound (A) is 500 to 50,000. [6] A method for producing an optical component according to any one of [1] to [5], wherein the number of hydroxyl groups per molecule of the hydroxyl group-containing polyether compound (A) is 1 to 10. [7] A method for producing an optical component according to any one of [1] to [6], wherein the iso(thio)cyanate compound (B) with two or more functions is selected from alicyclic polyiso(thio)cyanate compounds, aromatic polyiso(thio)cyanate compounds, and modified versions thereof, one or more of these. [8] A method for producing an optical component according to any one of [1] to [7], wherein the isocyanate compound (B) with two or more functions is selected from one or more of xylylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate. [9] A method for producing an optical component according to any one of [1] to [8], wherein the active hydrogen compound (C) has two or more functional groups selected from a hydroxyl group, a mercapto group, an amino group, and a carboxyl group.

[10] The active hydrogen compounds (C) with two or more functions 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, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptoethyl) A method for producing an optical component according to any one of [1] to [9], comprising one or more polythiols selected from the group consisting of (1) sulfide, 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, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate).

[11] A method for producing an optical component according to any one of [1] to

[10] , wherein a bifunctional or more iso(thio)cyanate compound (B) is further added in the second polymerization step.

[12] A method for manufacturing an optical component according to any one of [1] to

[11] , wherein the reaction is carried out by heating to a maximum temperature of 100°C to 150°C in the second polymerization step.

[13] A method for producing an optical component according to any one of [1] to

[12] , further comprising a mixing step of mixing a hydroxyl group-containing polyether compound (A), a bifunctional or more iso(thio)cyanate compound (B), and a functional compound (E) before the first polymerization step.

[14] The method for producing an optical component according to

[13] , wherein the functional compound (E) is a photochromic compound (e).

[15] The method for producing an optical member according to

[14] , wherein the photochromic compound (e) is a naphthopyran-based compound having no active hydrogen.

[16] The method for producing an optical member according to

[14] or

[15] , wherein the photochromic compound (e) is one or more selected from naphthopyran-based compounds and spirobipyran-based compounds. [Effect of the Invention]

[0014] According to the present invention, there is provided a manufacturing method capable of obtaining an optical member in which a functional compound is applied and the function of the functional compound can be more effectively exhibited. [Embodiments for Carrying Out the Invention]

[0015] The optical member and the manufacturing method thereof according to the present invention will be described based on the following embodiments. Note that the description of the constituent elements described below may be made based on typical embodiments of the present disclosure, but the present disclosure is not limited to such embodiments. In addition, the symbol "a~b" indicating a numerical range represents a to b inclusive, unless otherwise specified.

[0016] <Method for Producing an Optical Member> The method for producing an optical member of the present embodiment includes the following steps. · Step 1 (Mixing Step): A mixing step of mixing a hydroxyl group-containing polyether compound (A), a polyisocyanate compound (B) having two or more functional groups, and a photochromic compound (e). · Step 2 (First Polymerization Step): A first polymerization step of reacting a hydroxyl group-containing polyether compound (A) and a polyisocyanate compound (B) having two or more functional groups to obtain a prepolymer. · Step 3 (Second Polymerization Step): A second polymerization step of mixing the obtained prepolymer, a polyfunctional active hydrogen compound (C), and a catalyst (D) and subjecting them to polymerization curing.

[0017] Thereby, in the optical member obtained by applying the functional compound, the function of the functional compound can be effectively exhibited. In this embodiment, the photochromic performance of the photochromic compound (e) can be improved. Examples of improved photochromic performance include high color intensity and fast color change / decolorization speed.

[0018] The details of how this effect is achieved are not clear, but it can be inferred as follows: Conventionally, polymerization curing was performed by mixing a hydroxyl group-containing polyether compound (A), an iso(thio)cyanate compound (B), and an active hydrogen compound (C) together. In contrast, in the optical component manufacturing method of this embodiment, a prepolymer is obtained by reacting the hydroxyl group-containing polyether compound (A) and the iso(thio)cyanate compound (B) in step 1 before polymerization curing. It is presumed that this makes it easier for the functional compound (E) to be incorporated into the domains formed from the hydroxyl group-containing polyether compound (A), allowing for the application of higher concentrations of the functional compound (E) and increasing the proportion of the functional compound (E) incorporated into the domains, thus making it easier for the functional compound to exert its effects.

[0019] In this embodiment, an example including step 1 (mixing step) is described, but the present invention is not limited to including step 1 (mixing step). Also, an example in which a photochromic compound (e) is used as the functional compound (E) is described, but the functional compound (E) is not limited to this.

[0020] The details of each step are explained below.

[0021] [Process 1 (mixing process)] First, when using photochromic compound (e), before step 2 (first polymerization step), the hydroxyl group-containing polyether compound (A), the iso(thio)cyanate compound (B), and the photochromic compound (e) are mixed.

[0022] This makes it possible to obtain optical components with photochromic properties.

[0023] The mixing method is not particularly limited and can be mixed using conventionally known methods, such as stirring by known means. The stirring speed should be adjusted as appropriate depending on the stirring means and scale used, but is generally around 100 to 250 rpm. The temperature during mixing should preferably be lower than room temperature (25°C).

[0024] The hydroxyl group-containing polyether compound (A), the iso(thio)cyanate compound (B), and the photochromic compound (e) may be added to the mixing vessel simultaneously or separately, and the order of addition is not particularly limited.

[0025] [Step 2 (First polymerization step)] Next, a hydroxyl group-containing polyether compound (A) and an iso(thio)cyanate compound (B) are reacted to obtain a prepolymer.

[0026] The preferred method of reaction involves heating a mixture containing a hydroxyl group-containing polyether compound (A) and an iso(thio)cyanate compound (B) to react the hydroxyl group of the hydroxyl group-containing polyether compound (A) with the iso(thio)cyanate group of the iso(thio)cyanate compound (B). The heating temperature is preferably 20°C to 150°C, more preferably 40°C to 120°C, and even more preferably 50°C to 100°C. The heating time can be adjusted as appropriate, but for example, it can be 10 to 24 hours.

[0027] During heating, it is preferable to continue stirring to ensure a uniform reaction. The stirring speed is not particularly limited, but is typically around 100 to 250 rpm.

[0028] The formation of a prepolymer can be confirmed by differential scanning calorimetry (DSC) by the completion of the exothermic reaction between the hydroxyl group of the hydroxyl group-containing polyether compound (A) and the iso(thio)cyanate group of the iso(thio)cyanate compound (B).

[0029] After the prepolymer is obtained, it is preferable to cool the mixture to room temperature (25°C) or below.

[0030] The amount of hydroxyl group-containing polyether compound (A) blended is preferably 0.5% by mass or more and 50% by mass or less, and more preferably 1 to 25% by mass, when the total amount of hydroxyl group-containing polyether compound (A) and iso(thio)cyanate compound (B) is taken as 100% by mass.

[0031] The ratio (iso(thio)cyanate group / hydroxyl group) of the hydroxyl group-containing polyether compound (A) to the iso(thio)cyanate group-equation of the iso(thio)cyanate compound (B) is preferably 10 to 100,000, more preferably 1 to 10,000, and even more preferably 10 to 5,000.

[0032] The details of each material are described below.

[0033] (Hydroxyl group-containing polyether compound (A)) The hydroxyl group-containing polyether compound (A) in this embodiment is a polyether compound containing at least one hydroxyl group and comprises at least one polyether segment. In this embodiment, the hydroxyl group-containing polyether compound (A) is preferably a block copolymer that may be combined with at least one segment of polyester, polycarbonate, poly(meth)acrylate, polyamide, polyethyleneimine, polysiloxane, polysulfide, polyolefin, or polystyrene, in addition to the polyether.

[0034] Another embodiment of the hydroxyl group-containing polyether compound (A) of this embodiment is a linear polyether block copolymer having at least two different segments. Examples of segment structures include segment structures having divalent organic groups derived from ethylene glycolate, propylene glycolate, butylene glycolate, etc., or divalent organic groups derived from ethanedithiol, propanedithiol, etc.

[0035] The above-mentioned polyethers are not particularly limited, but examples include polyethylene glycol, polypropylene glycol, or polybutylene glycol.

[0036] The above-mentioned polyesters are not particularly limited, but include those obtained from the condensation of dicarboxylic acids and diols.

[0037] Examples of the dicarboxylic acids mentioned above include adipic acid, succinic acid, or combinations thereof.

[0038] Examples of the diols mentioned above include ethylene-1,2-diol, butane-1,4-diol, hexane-1,6-diol, propane-1,2-diol, 3-methylpentane-1,5-diol, 2-methylpropane-1,3-diol, 2,2-dimethylpropane-1,3-diol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, pentane-1,5-diol, heptane-1,7-diol, etc., or combinations thereof.

[0039] Examples of the polyesters mentioned above include polycaprolactone, polybutyrolactone, polyvalerolactone, polylactic acid, polyglycolic acid, or combinations thereof.

[0040] The polycarbonates mentioned above are not particularly limited, but examples include those obtained by condensation between a carbonate and a diol.

[0041] Examples of the diols mentioned above include ethylene-1,2-diol, butane-1,4-diol, hexane-1,6-diol, propane-1,2-diol, 3-methylpentane-1,5-diol, 2-methylpropane-1,3-diol, 2,2-dimethylpropane-1,3-diol, pentane-1,5-diol, heptane-1,7-diol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc., or combinations thereof.

[0042] The poly(meth)acrylates mentioned above are not particularly limited, but examples include methyl(meth)acrylate, butyl(meth)acrylate, hexyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, benzyl(meth)acrylate, phenyl(meth)acrylate, etc., or combinations thereof.

[0043] The polyamides mentioned above are not particularly limited, but examples include those obtained by the condensation of a dicarboxylic acid and a diamine.

[0044] Examples of the dicarboxylic acids mentioned above include adipic acid, succinic acid, or combinations thereof. Examples of the diamines mentioned above include hexamethylenediamine.

[0045] Examples of polyamides mentioned above include lactams such as polycaprolactam.

[0046] The polyethyleneimines mentioned above include polyethyleneimine chains, polypropionyl aziridine chains, polyacetyl aziridine chains, and polyformyl aziridine chains, among others, as polymer chains.

[0047] Examples of the polysiloxanes mentioned above, which are polymer chains, include polydimethylsiloxane chains and polymethylphenylsiloxane chains.

[0048] The above polysulfide may include polyethylene sulfide chains, etc.

[0049] Examples of the polyolefins mentioned above include polyethylene, polypropylene, and combinations thereof.

[0050] The polystyrenes mentioned above include polystyrene, polystyrene sulfonate, and combinations thereof.

[0051] The hydroxyl group-containing polyether compound (A) of this embodiment forms a domain structure. More specifically, it forms micelles through microphase separation, providing a uniformly dispersed nano-sized structure. In the optical component of this embodiment, the micelle structure can effectively disperse functional compounds such as photochromic dyes while maintaining mechanical and optical properties.

[0052] The number of hydroxyl groups per molecule of the hydroxyl group-containing polyether compound (A) is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 6. By setting the number of hydroxyl groups per molecule of the hydroxyl group-containing polyether compound (A) within the above numerical range, the functionality of the functional compound (E) can be more easily exhibited, and for example, the performance of the photochromic compound, such as the color intensity and color change speed, can be improved.

[0053] The number-average molecular weight of the hydroxyl group-containing polyether compound (A) is preferably 500 to 50,000, more preferably 1,000 to 30,000, and even more preferably 2,000 to 20,000. By setting the number-average molecular weight of the hydroxyl group-containing polyether compound (A) to be above the lower limit, it becomes easier to improve the function of the functional compound, for example, to improve the photochromic performance. On the other hand, by setting the number-average molecular weight of the hydroxyl group-containing polyether compound (A) to be below the upper limit, it is possible to suppress clouding of the optical component while maintaining the function of the functional compound.

[0054] (Iso(thio)cyanate compound (B)) The isocyanate compound (B) in this embodiment is an isocyanate compound having two or more isocyanate groups, where isocyanate compound means isocyanate compound or isothiocyanate compound. Examples of the iso(thio)cyanate compound (B) in this embodiment include alicyclic polyiso(thio)cyanate compounds, aromatic polyiso(thio)cyanate compounds, and modified versions thereof.

[0055] More specifically, isocyanate compounds include isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane isocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and 3,8-bis(isocyanatomethyl) Examples include alicyclic polyisocyanate compounds such as methyl)tricyclodecane, 3,9-bis(isocyanatomethyl)tricyclodecane, 4,8-bis(isocyanatomethyl)tricyclodecane, and 4,9-bis(isocyanatomethyl)tricyclodecane; and aromatic polyisocyanate compounds such as phenylenediisocyanate, 2,4-tolylenediisocyanate, 2,6-tolylenediisocyanate, 4,4'-diphenylmethanediisocyanate, and diphenylsulfide-4,4'-diisocyanate.

[0056] Examples of isothiocyanate compounds include isophorone diisothiocyanate, bis(isothiocyanatomethyl)cyclohexane, dicyclohexylmethane diisothiocyanate, cyclohexane diisothiocyanate, methylcyclohexane diisothiocyanate, 2,5-bis(isothiocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isothiocyanatomethyl)bicyclo-[2.2.1]-heptane, and 3,8-bis(isothiocyanatomethyl) Examples include alicyclic polyisothiocyanate compounds such as 3,9-bis(isothiocyanatomethyl)tricyclodecane, 4,8-bis(isothiocyanatomethyl)tricyclodecane, and 4,9-bis(isothiocyanatomethyl)tricyclodecane; and aromatic polyisothiocyanate compounds such as tolylene diisothiocyanate, 4,4'-diphenylmethane diisothiocyanate, and diphenyl disulfide-4,4'-diisothiocyanate.

[0057] As the iso(thio)cyanate compound (B), halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds, alkyl-substituted compounds, alkoxy-substituted compounds, nitro-substituted compounds, prepolymer-type modified compounds with polyhydric alcohols, carbodiimide-substituted compounds, urea-substituted compounds, biuret-substituted compounds, dimerization or trimmerization reaction products, etc., can also be used. Furthermore, iso(thio)cyanate compound (B) can be used in combination of one or more selected from these.

[0058] [Photochromic compounds (e)] Photochromic compounds (e) include compounds whose absorption properties (absorption spectrum) change in response to light of a specific wavelength. As the photochromic compound (e) in this embodiment, known compounds can be used, for example, obtained by the methods described in International Publication Nos. 2009 / 146509, 2010 / 20770, 2012 / 149599, and 2012 / 162725. Specifically, examples include spiropyran compounds, spirooxazine compounds, fulgide compounds, naphthopyran compounds, bisimidazole compounds, etc. Among these, naphthopyran compounds and spiropyran compounds are preferred, and naphthopyran compounds that do not contain active hydrogen are more preferred.

[0059] [Second polymerization step] The prepolymer obtained in the first polymerization step is mixed with an active hydrogen compound (C) and a catalyst (D), and then polymerized and cured. That is, a polymerizable composition containing the prepolymer and the active hydrogen compound (C) and catalyst (D) is obtained, and then the polymerizable composition is polymerized and cured to obtain an optical component.

[0060] The mixing method is not particularly limited and can be mixed using conventionally known methods, such as stirring by known means. The stirring speed should be adjusted as appropriate depending on the stirring means and scale used, but is generally around 100 to 250 rpm.

[0061] When mixing the active hydrogen compound (C) and the catalyst (D), the temperature is preferably below room temperature, more preferably 15-20°C.

[0062] The active hydrogen compound (C) and the catalyst (D) may be mixed together with the prepolymer, or they may be mixed separately, in any order.

[0063] Furthermore, in the second polymerization step, the polymerizable composition may be further mixed with other additives described later (such as internal release agents, resin modifiers, light stabilizers, and bluing agents). However, if the solubility of additives such as catalyst (D) and internal release agents is not good, the mixture may be heated beforehand before mixing.

[0064] Furthermore, an iso(thio)cyanate compound (B) may be added in the second polymerization step. This can increase the polymerization rate during polymerization curing.

[0065] The following describes the details of each material included in the polymerizable composition.

[0066] [Active hydrogen compounds (C)] The active hydrogen compound (C) of this embodiment has two or more functional groups. Examples of functional groups include hydroxyl groups, mercapto groups, amino groups, and carboxyl groups. Examples of active hydrogen compounds (C) include poly(thiol) compounds having two or more hydroxyl groups or mercapto groups, polyamine compounds having two or more primary amino groups or secondary amino groups, and polycarboxylic acid compounds having two or more carboxyl groups. Also, compounds having two or more active hydrogen groups selected from hydroxyl groups, mercapto groups, primary amino groups, secondary amino groups, carboxyl groups, etc., in a single molecule are also examples. The two or more active hydrogen groups may be the same or different.

[0067] For example, difunctional or more active hydrogen compounds having hydroxyl groups, such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, glycerin, polyglycerin, and thioglycerin; Trithioglycerin, pentaerythritol tetrakis(thioglycolate), trimethylolpropane(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate), bis(2-mercaptoethyl) sulfide, 4-mercaptomethyl-3,6-dithiaoctane-1,8-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane- Active hydrogen compounds with two or more functions having a mercapto group, such as 1,11-dithiol, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 1,1,3,3-tetrakis(mercaptomethyl)-2-thiapropane, 1,4-dithiane-2,5-dithiol, 2,5-bis(mercaptomethyl)-1,4-dithiane, and xylylenedithiol; Examples include xylylenediamine, α,α,α',α'-tetramethyl-xylylenediamine, 1,5-diaminopentane, 1,6-diaminohexane, diaminopolypropylene, diaminopolyethylene, isophoronediamine, bis(aminocyclohexyl)methane, bis(aminomethyl)cyclohexane, bis(aminomethyl)norbornane, and other bifunctional or more active hydrogen compounds having amino groups.

[0068] [Catalyst (D)] The catalyst (D) in this embodiment can be one or more selected from Lewis acids, tertiary amines, organic acids, amine organic salts, etc. Among these, Lewis acids, amines, and amine organic salts are preferred, and dimethyltin chloride, dibutyltin dichloride, and dibutyltin laurate are more preferred.

[0069] [others] The polymerizable composition of this embodiment may further contain additives such as internal mold release agents, resin modifiers, light stabilizers, antioxidants, and color inhibitors, depending on the desired properties for the application.

[0070] (Internal release agent) The polymerizable composition of this embodiment may contain an internal release agent to improve mold release after molding. Acidic phosphate esters can be used as internal release agents. Examples of acidic phosphate esters include phosphate monoesters and phosphate diesters, which can be used individually or in combination of two or more types. Examples of commercially available internal release agents include ZelecUN from STEPAN, MR internal release agent from Mitsui Chemicals, Inc., JP series from Johoku Chemical Industry, Phosphanol series from Toho Chemical Industry, and AP and DP series from Daihachi Chemical Industry.

[0071] (Resin modifier) The optical component of this embodiment may contain a resin modifier for the purpose of adjusting various physical properties such as optical properties, impact resistance, and specific gravity, as well as adjusting the viscosity and pot life of the polymerizable composition. Examples of resin modifiers include episulfide compounds, alcohol compounds other than the polyol compounds mentioned above, amine compounds other than the amine compounds mentioned above, epoxy compounds, organic acids and their anhydrides, and olefin compounds including (meth)acrylate compounds.

[0072] (Light stabilizer) As a light stabilizer, hindered amine compounds having a 2,2,6,6-tetramethylpiperidine skeleton or a 1,2,2,6,6-pentamethylpiperidine skeleton can be used. Examples of commercially available hindered amine compounds include Lowilite 76 and Lowilite 92 from Chemtura, Tinuvin 144, Tinuvin 292, and Tinuvin 765 from BASF, Adeka Stab LA-52 and LA-72 from ADEKA, JF-95 from Johoku Chemical Industry Co., Ltd., and Hostavin PR-25 from Clariant Chemicals.

[0073] Subsequently, the polymerizable composition is polymerized to obtain the optical component of this embodiment. The polymerization method can be a conventionally known method, and the conditions are not particularly limited.

[0074] Optical components can be obtained in various shapes depending on the shape of the mold. The molding method for optical components is not particularly limited, but casting polymerization is preferred. Specifically, first, a polymerizable composition is injected between molding molds held together by gaskets or tape. At this time, depending on the physical properties required of the resulting optical component, it may be preferable to perform degassing treatment under reduced pressure, or filtration treatment under pressure or reduced pressure, as needed.

[0075] Polymerization conditions are not limited to those specified in the original text, as they vary depending on the composition of the polymerization composition, the type and amount of catalyst used, the shape of the mold, etc. However, polymerization is generally carried out at a temperature of approximately -50 to 150°C for 1 to 50 hours. In some cases, it is preferable to maintain the temperature in the range of 10 to 150°C or gradually increase the temperature and cure it for 1 to 25 hours.

[0076] The optical component of this embodiment may be subjected to treatments such as annealing as needed. The treatment temperature is usually between 50 and 150°C, but is preferably between 90 and 140°C, and more preferably between 100 and 130°C.

[0077] The optical component of this embodiment is colorless and transparent, has an excellent appearance, and is also provided with photochromic functionality by containing a photochromic compound (e).

[0078] The above describes the case in which a photochromic compound (e) is used as the functional compound (E) in this embodiment. However, functional compounds (E) other than the photochromic compound (e) will be described below.

[0079] [Functional compound (E)] Functional compound (E) is used to add a new function to the optical component of this embodiment. Examples of functional compound (E) include photochromic compound (e), dyes, ultraviolet absorbers, blooming agents, visible light absorbing dyes, and the like. According to the optical component of this embodiment, when a dye is applied, the dyeability is improved; when an ultraviolet absorber is applied, the ultraviolet cut rate can be increased; and when a blooming agent is applied, the hue of a specific wavelength can be changed.

[0080] (UV absorber) Examples of UV absorbers include benzophenone compounds, triazine compounds, and benzotriazole compounds.

[0081] Examples of benzophenone-based UV absorbers include 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, and 2-hydroxy-4-acryloyloxy-2',4'-dichlorobenzophenone.

[0082] Examples of triazine-based UV absorbers include 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'-eth Examples include [Hexyl)oxy]-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.

[0083] Examples of benzotriazole-based UV absorbers include 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-tert-butylphenol, 2-(5-chloro-2H-benzotriazole-2-yl)-2,4-tert-butylphenol, and 2,2'-methylenebis[6-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol]. These UV absorbers may be used individually or in combination of two or more.

[0084] (Bluing agent) 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 components made of resin. More specifically, bluing agents include substances that exhibit a blue to purple color.

[0085] (Visible light absorbing dye) Commercially available visible light absorbing dyes may be used, and organic dye compounds are preferred. Specifically, porphyrin compounds or tetraazaporphyrin compounds are examples. More specifically, PD-311S (manufactured by Yamamoto Kasei Co., Ltd.) is an example of a visible light absorbing dye.

[0086] <Optical components> Applications of the optical components of this embodiment include plastic lenses, camera lenses, light-emitting diode lenses, light-emitting diode lens cases, prisms, optical fibers, information recording substrates, filters, and the like. Optical materials or optical elements such as plastic lenses, camera lenses, light-emitting diode lenses, and light-emitting diode lens cases are particularly preferred.

[0087] The plastic lens containing the optical component of this embodiment may be used as a laminated plastic lens by applying a coating layer to one or both sides of the lens substrate made of the optical component, as needed. Examples of coating layers include a primer layer, a hard coat layer, an anti-reflective coating layer, an anti-fog coating layer, an anti-stain layer, and a water-repellent layer. These coating layers can be used individually or in multiple layers. When coating layers are applied to both sides, the same coating layer may be applied to each side, or different coating layers may be applied to each side.

[0088] These coating layers may each contain infrared absorbers to protect the eyes from infrared radiation, light stabilizers and antioxidants to improve the weather resistance of the lenses, dyes and pigments to enhance the fashionability of the lenses, as well as photochromic dyes and pigments, antistatic agents, and other known additives to improve lens performance. Coating layers such as hard coat layers and anti-reflective coatings, or primer layers may also be provided.

[0089] The plastic lenses of this embodiment may be dyed using dyes appropriate to the purpose, such as to impart fashionability or photochromic properties. Lens dyeing can be carried out using known dyeing methods.

[0090] The present disclosure has been described above based on this embodiment, but various configurations can be adopted as long as they do not impair the effects of the present disclosure. [Examples]

[0091] The present invention will be described below with reference to examples and comparative examples, but the present invention is not limited to these. First, the evaluation items and evaluation methods for molded articles in the examples of the present invention are shown below.

[0092] (1) Evaluation method [Dimming performance evaluation] Using a xenon lamp (180W) light source, under conditions of a temperature of 23°C and an integrated light intensity of 50,000 lux (lx) measured with an integrated light meter, each molded sample obtained in (3) below was allowed to develop color for 15 minutes. The transmittance (%) of a molded sample with a thickness of 0.7 mm was then measured to confirm the color density. A lower transmittance indicates a higher color density. • Light source: Ushio Electric Co., Ltd. MS-35AAF / FB • Instantaneous multi-photometering system: Otsuka Electronics Co., Ltd. MSPD-7700

[0093] (2) Raw materials (partial) [Hydroxygroup-containing polyether compound (A)] • Hydroxyl group-containing polyether compound (A1); polyethylene glycol, polypropylene glycol, polyethylene glycol (Adeka Pluronic® L-64, manufactured by Adeka Corporation), number average molecular weight 2900, number of hydroxyl groups per molecule: 2 • Hydroxyl group-containing polyether compound (A2); polyoxyethylene polyoxypropylene glycol (Pluronic F127, manufactured by BASF), number-average molecular weight 12600, number of hydroxyl groups per molecule: 2

[0094] [Photochromic compounds (e)] • Photochromic compound (e1); Reversacol Wembley Grey (R1966): 500 ppm • Photochromic compound (e2); Reversacol Jalapeno Red (R1950): 500 ppm

[0095] (3) Fabrication of optical components and photochromic lenses (molded bodies) <Comparative Example 1> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e2) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 41.3 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane were added to 10 parts by weight of the resulting master solution and stirred. Then, 8.6 parts by weight of a hydroxyl group-containing polyether compound (A1), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and stirred for 30 minutes at 15°C to 20°C (mixing step). Meanwhile, 40.1 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.015 parts by weight of dimethyl tin dichloride were added beforehand and uniformly dissolved to prepare a solution. This solution was added to the mixture obtained in the mixing step and stirred for 15 minutes at 15°C to 20°C to obtain a polymerizable composition (mixing step). Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the resulting polymerizable composition was poured into a glass mold and then heated from 10°C to 130°C over 24 hours (polymerization step). After cooling to room temperature, it was removed from the glass mold to obtain a photochromic lens. The obtained photochromic lenses (molded samples) were evaluated and measured as described in (1) above. The results are shown in Table 1.

[0096] <Example 1> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e2) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 20.78 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added to 10 parts by weight of the resulting master solution and stirred. Then, 8.6 parts by weight of a hydroxyl group-containing polyether compound (A1), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and the mixture was stirred at 60°C for 14 hours or more (first polymerization step). In the first polymerization step, 30.78 parts by weight of the composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, along with the photochromic compound (e2), were divided by the final amount used, 51.3, to define a prepolymer ratio of 60%. To the solution obtained after the first polymerization step, 20.52 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added and stirred for 5 minutes at 15°C to 20°C to obtain a second solution. Meanwhile, 40.1 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.015 parts by weight of dimethyl tine dichloride were added beforehand and uniformly dissolved to prepare a solution. This solution was added to the second solution and stirred for 15 minutes at 15°C to 20°C to obtain a polymerizable composition. Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the obtained polymerizable composition was poured into the space surrounded by glass molds and then heated from 10°C to 130°C over 24 hours (second polymerization step). The distance between glass molds at the center of the lens was set to 0.8 mm. After cooling to room temperature, the lens was removed from the glass molds to obtain a 0.7 mm thick photochromic lens. The obtained photochromic lenses (molded samples) were evaluated and measured as described in (1) above. The results are shown in Table 1.

[0097] <Example 2> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e2) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 41.3 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane were added to 10 parts by weight of the resulting master solution and stirred. Then, 8.6 parts by weight of a hydroxyl group-containing polyether compound (A1), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and the mixture was stirred at 60°C for 14 hours or more (first polymerization step). In the first polymerization step, 51.3 parts by weight of the composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, along with the photochromic compound (e2), were divided by the final amount used, 51.3, and defined as a prepolymer ratio of 100%. Meanwhile, 40.1 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.015 parts by weight of dimethyl tin dichloride were added beforehand and uniformly dissolved to prepare a solution. This solution was added to the mixture obtained in the first polymerization step and mixed for 15 minutes at 15°C to 20°C to obtain a polymerizable composition. Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the obtained polymerizable composition was poured into a glass mold and then heated from 10°C to 130°C over 24 hours (second polymerization step). After cooling to room temperature, it was removed from the glass mold to obtain a photochromic lens. The obtained photochromic lens (molded sample) was evaluated and measured as described in (1) above. The results are shown in Table 1.

[0098] <Comparative Example 2> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e1) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 43.33 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added to 10 parts by weight of the resulting master solution and stirred. Then, 2.5 parts by weight of a hydroxyl group-containing polyether compound (A2), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and stirred for 30 minutes at 15°C to 20°C (first polymerization step). A solution was prepared by first adding 44.17 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane to 0.015 parts by weight of dimethyl tine dichloride and dissolving it uniformly. This solution was added to the mixture obtained in the first polymerization step and stirred for 15 minutes at 15°C to 20°C to obtain a polymerizable composition. Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the resulting polymerizable composition was poured into a glass mold and then heated from 10°C to 130°C over 24 hours (second polymerization step). After cooling to room temperature, it was removed from the glass mold to obtain a photochromic lens. The obtained photochromic lenses (molded samples) were evaluated and measured as described in (1) above. The results are shown in Table 1.

[0099] <Example 3> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e1) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 21.98 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added to 10 parts by weight of the resulting master solution and stirred. Then, 2.5 parts by weight of a hydroxyl group-containing polyether compound (A2), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and the mixture was stirred at 60°C for 14 hours or more (first polymerization step). In the first polymerization step, 31.98 parts by weight of the composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, along with Reversacol Wembley Grey from Vivimed, was divided by the final amount used, 53.3, to define a prepolymer ratio of 60%. To the solution obtained after the first polymerization step, 21.32 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added and stirred for 5 minutes at 15°C to 20°C to obtain a second solution. Meanwhile, 40.1 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.015 parts by weight of dimethyl tine dichloride were added beforehand and dissolved uniformly to prepare a solution. This solution was added to the second solution and stirred for 15 minutes at 15°C to 20°C to obtain a polymerizable composition. Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the resulting polymerizable composition was poured into a glass mold and then heated from 10°C to 130°C over 24 hours (second polymerization step). After cooling to room temperature, it was removed from the glass mold to obtain a photochromic lens. The obtained photochromic lenses (molded samples) were evaluated and measured as described in (1) above. The results are shown in Table 1.

[0100] <Example 4> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e1) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 41.3 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane were added to 10 parts by weight of the resulting master solution and stirred. Then, 2.5 parts by weight of a hydroxyl group-containing polyether compound (A2), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and the mixture was stirred at 60°C for 14 hours or more (first polymerization step). In the first polymerization step, 51.3 parts by weight of the composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, along with the photochromic compound (e2), were divided by the final amount used, 51.3, and defined as a prepolymer ratio of 100%. Meanwhile, 40.1 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.015 parts by weight of dimethyl tin dichloride were added beforehand and uniformly dissolved to prepare a solution. This solution was added to the mixture obtained in the first polymerization step and mixed for 15 minutes at 15°C to 20°C to obtain a polymerizable composition. Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the obtained polymerizable composition was poured into a glass mold and then heated from 10°C to 130°C over 24 hours (second polymerization step). After cooling to room temperature, it was removed from the glass mold to obtain a photochromic lens. The obtained photochromic lens (molded sample) was evaluated and measured as described in (1) above. The results are shown in Table 1.

[0101] <Comparative Example 3> A polymerizable composition and a photochromic lens (molded sample) were obtained in the same manner as in Comparative Example 2, except that photochromic compound (e1) was replaced with photochromic compound (e2). The obtained photochromic lens (molded sample) was evaluated and measured as described in (1) above. The results are shown in Table 1.

[0102] <Example 5> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (e2) in 9.95 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 31.04 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added to 10 parts by weight of the resulting master solution and stirred. Then, 2.5 parts by weight of a hydroxyl group-containing polyether compound (A2), 0.4 parts by weight of a polyether-modified siloxane compound (Polyflow KL-100, manufactured by Kyoeisha Chemical Co., Ltd.), and 0.1 parts by weight of an acidic phosphate ester (JP-506H, manufactured by Johoku Chemical Industry Co., Ltd.) were added and the mixture was stirred at 60°C for 14 hours or more (first polymerization step). In the first polymerization step, 41.04 parts by weight of the composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, along with the photochromic compound (e2), were divided by the final amount used, 51.3, to define a prepolymer ratio of 80%. To the solution obtained after the first polymerization step, 10.26 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was added and stirred for 5 minutes at 15°C to 20°C to obtain a second solution. Meanwhile, 40.1 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.015 parts by weight of dimethyl tine dichloride were added beforehand and uniformly dissolved to prepare a solution. This solution was added to the second solution and stirred for 15 minutes at 15°C to 20°C to obtain a polymerizable composition. Subsequently, the polymerizable composition was stirred and degassed for 1 hour and 30 minutes under reduced pressure of 400 Pa or less at a temperature between 15°C and 20°C. After filtration using a 1.0 μm PTFE filter, the obtained polymerizable composition was poured into a glass mold and then heated from 10°C to 130°C over 24 hours (second polymerization step). After cooling to room temperature, it was removed from the glass mold to obtain a photochromic lens. The obtained photochromic lens (molded sample) was evaluated and measured as described in (1) above. The results are shown in Table 1.

[0103] <Example 6> A polymerizable composition and a photochromic lens (molded sample) were obtained in the same manner as in Example 4, except that photochromic compound (e1) was replaced with photochromic compound (e2). The obtained photochromic lens (molded sample) was evaluated and measured as described in (1) above. The results are shown in Table 1.

[0104] [Table 1]

Claims

1. A first polymerization step involves reacting a hydroxyl group-containing polyether compound (A) with a bifunctional or more iso(thio)cyanate compound (B) to obtain a prepolymer, A second polymerization step involves mixing the obtained prepolymer with a bifunctional or more active hydrogen compound (C) and a catalyst (D), and polymerizing and curing the mixture. A method for manufacturing optical components, including [the specified component].

2. A method for producing an optical component according to claim 1, wherein in the first polymerization step, a hydroxyl group-containing polyether compound (A) and a bifunctional or more iso(thio)cyanate compound (B) are mixed and reacted by heating to a temperature of 20°C or higher and 150°C or lower.

3. A method for producing an optical member according to claim 1 or 2, wherein, in the first polymerization step, when the total amount of the hydroxyl group-containing polyether compound (A) and the bifunctional or more iso(thio)cyanate compound (B) is 100% by mass, the amount of the hydroxyl group-containing polyether compound (A) is 0.5% by mass or more and 50% by mass or less.

4. A method for producing an optical member according to claim 1 or 2, wherein in the first polymerization step, the ratio (hydroxyl group / iso(thio)cyanate group) of the number of hydroxyl group equivalents of the hydroxyl group-containing polyether compound (A) to the number of iso(thio)cyanate group equivalents of the bifunctional or more iso(thio)cyanate compound (B) is 10 to 100,000.

5. A method for producing an optical component according to claim 1 or 2, wherein the number average molecular weight of the hydroxyl group-containing polyether compound (A) is 500 to 50,000.

6. A method for producing an optical component according to claim 1 or 2, wherein the number of hydroxyl groups per molecule of the hydroxyl group-containing polyether compound (A) is 1 to 10.

7. A method for producing an optical component according to claim 1 or 2, wherein the bifunctional or more iso(thio)cyanate compound (B) is one or more selected from alicyclic polyiso(thio)cyanate compounds, aromatic polyiso(thio)cyanate compounds, and modified versions thereof.

8. A method for producing an optical component according to claim 1 or 2, wherein the bifunctional or more iso(thio)cyanate compound (B) is one or more selected from xylylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate.

9. A method for producing an optical component according to claim 1 or 2, wherein the bifunctional or more active hydrogen compound (C) has one or more functional groups selected from a hydroxyl group, a mercapto group, an amino group, and a carboxyl group.

10. The active hydrogen compounds (C) with two or more functions 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, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercapto A method for producing an optical component according to claim 1 or 2, comprising one or more polythiols selected from the group consisting of toethyl) sulfide, 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, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate).

11. A method for producing an optical component according to claim 1 or 2, wherein a bifunctional or more iso(thio)cyanate compound (B) is further added in the second polymerization step.

12. A method for manufacturing an optical member according to claim 1 or 2, wherein in the second polymerization step, the reaction is carried out by heating to a maximum temperature of 100°C to 150°C.

13. A method for producing an optical component according to claim 1 or 2, further comprising a mixing step of mixing a hydroxyl group-containing polyether compound (A), a bifunctional or more iso(thio)cyanate compound (B), and a functional compound (E) before the first polymerization step.

14. A method for producing an optical component according to claim 13, wherein the functional compound (E) is a photochromic compound (e).

15. The method for producing an optical component according to claim 14, wherein the photochromic compound (e) is a naphthopyrane compound that does not contain active hydrogen.

16. The method for producing an optical component according to claim 14, wherein the photochromic compound (e) is one or more selected from naphthopyrane compounds and spiropyran compounds.

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