Optical components and optical lenses

Abstract

The present invention provides an optical component to which a photochromic compound is applied, which can more effectively exhibit its photochromic function. [Solution] The optical member of this embodiment comprises a hydroxyl group-containing polyether compound (A), a bifunctional or more iso(thio)cyanate compound (B), a bifunctional or more active hydrogen compound (C), a catalyst (D), and a photochromic compound (E), and the haze (%) relative to the thickness (mm) at the center of the optical member is 0.58% / mm or more.

Description

Technical Field

[0001] The present invention relates to an optical member and an optical lens.

Background Art

[0002] Plastic lenses are lightweight, difficult to break, and can be dyed, so they have rapidly spread as optical materials for spectacle lenses, camera lenses, etc. 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, highly 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 clouding 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 glasses, it can function as ordinary transparent glasses 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 changing glasses indoors and outdoors like sunglasses, and it is possible to use a single pair of glasses both indoors and outdoors.

[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 exhibited. For example, plastic lenses obtained using a plastic material to which a photochromic compound is applied are 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 view of these circumstances, the present invention aims to enable optical components to which photochromic compounds are applied to exhibit their photochromic function more effectively. [Means for solving the problem]

[0011] The inventors of this invention conducted diligent research to solve the above problems and, unexpectedly, discovered that good photochromic function could be obtained by controlling the haze value, thus completing the present invention.

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

[0013] [1] An optical component comprising a hydroxyl group-containing polyether compound (A), a bifunctional or more iso(thio)cyanate compound (B), a bifunctional or more active hydrogen compound (C), a catalyst (D), and a photochromic compound (E), An optical component having a haze (%) of 0.58% / mm or more relative to its thickness (mm) at the center of the optical component. [2] The optical component according to [1], wherein the number average molecular weight of the hydroxyl group-containing polyether compound (A) is 500 to 50,000. [3] The optical component according to [1] or [2], wherein the hydroxyl group-containing polyether compound (A) has 1 to 10 hydroxyl groups per molecule. [4] The optical component according to any one of [1] to [3], 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. [5] The optical component according to any one of [1] to [4], 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. [6] The optical component according to any one of [1] to [5], 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. [7] 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 An optical component according to any one of [1] to [6], 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). [8] The optical component according to any one of [1] to [7], wherein the photochromic compound (E) is a naphthopyrane compound that does not contain active hydrogen. [9] The optical component according to any one of [1] to [8], wherein the photochromic compound (E) is one or more selected from naphthopyrane compounds and spiropyran compounds.

[10] An optical lens comprising any one of the optical components described in [1] to [9]. [Effects of the Invention]

[0014] According to the present invention, an optical component to which a photochromic compound is applied is provided that can more effectively exhibit its photochromic function. [Modes for carrying out the invention]

[0015] The optical component of the present invention and its manufacturing method will be described based on the following embodiments. The following descriptions of constituent elements may be based on representative embodiments of this disclosure, but this disclosure is not limited to such embodiments. Furthermore, unless otherwise specified, the numerical range symbols "a~b" represent a or greater and b or less.

[0016] <Optical components> The optical component of this embodiment comprises a hydroxyl group-containing polyether compound (A), a bifunctional or more isocyanate compound (B), a bifunctional or more active hydrogen compound (C), a catalyst (D), and a photochromic compound (E), and the haze (%) (hereinafter also referred to as "haze H (% / mm)") relative to the thickness (mm) at the center of the optical component is 0.58% / mm or more.

[0017] The optical component of this embodiment can exhibit its photochromic function more effectively by controlling the haze H (% / mm). Specifically, the color intensity produced by the photochromic compound (E) can be improved. Although the details of such reasons are not clear, they are presumably as follows. That is, the photochromic compound (E) is incorporated into the hydroxyl group-containing polyether compound (A), and the hydroxyl group-containing polyether compound (A), the iso(thio)cyanate compound (B), and the active hydrogen compound (C) are polymerized and cured to form an optical member, whereby the photochromic function can be exhibited within the optical member. Therefore, it is presumed that the photochromic function, especially the coloring density, can be improved by incorporating the photochromic compound (E) into the hydroxyl group-containing polyether compound (A) at as high a concentration as possible. On the other hand, it is presumed that when the photochromic compound (E) is present in a high concentration in the optical member, light diffusion is likely to occur and the haze fluctuates. Therefore, it is presumed that by controlling the optical member so that the haze H (% / mm) falls within a predetermined numerical range, it becomes easier to exhibit the function of the photochromic compound (E).

[0018] In this embodiment, the haze H (% / mm) is 0.58% / mm or more, preferably 0.59% / mm or more, and more preferably 0.60% / mm or more. Thereby, the photochromic function can be improved and the dimming performance can be enhanced. On the other hand, the upper limit of the haze H (% / mm) is not particularly limited, but from the viewpoint of maintaining good moldability and the like, it is preferably 20% / mm or less, more preferably 15% / mm or less, and even more preferably 10% / mm or less.

[0019] Further, the haze H (% / mm) is preferably set according to the number average molecular weight of the hydroxyl group-containing polyether compound (A1). For example, when the number average molecular weight of the hydroxyl group-containing polyether compound (A1) is 500 to 10,000, the haze H (% / mm) is preferably 0.58 to 10% / mm, more preferably 0.58 to 8.0% / mm, and even more preferably 0.58 to 5.0% / mm. Furthermore, when the number-average molecular weight of the hydroxyl group-containing polyether compound (A1) is 10,000 to 50,000, the haze H (% / mm) is preferably 1 to 10% / mm, more preferably 3 to 10% / mm, and even more preferably 5 to 10% / mm. This allows for increased photochromic properties, particularly in terms of color intensity.

[0020] The term "center of an optical component" refers to the central part of the optical component in a plan view. For example, if the optical component is curved in a convex shape, it refers to the central part in a plan view (top view of the convex part) when the convex part is oriented in the thickness direction.

[0021] The thickness is measured using a TECLOCK SM-130LW dial thickness gauge.

[0022] The haze value (%) is measured using a haze meter. A lower haze value (%) indicates higher transparency as an optical lens.

[0023] Optical components that satisfy the above haze H (% / mm) can be realized, for example, by selecting the type and number-average molecular weight of the hydroxyl group-containing polyether compound (A), combining the hydroxyl group-containing polyether compound (A) with a bifunctional or more iso(thio)cyanate compound (B), and devising a method for manufacturing the optical component. Specifically, one example is a method in which a prepolymer is polymerized beforehand by reacting a hydroxyl group-containing polyether compound (A) and a bifunctional or more iso(thio)cyanate compound (B), and then the prepolymer is mixed with a bifunctional or more active hydrogen compound (C) and a catalyst (D) to undergo polymerization curing. In this case, the photochromic compound (E) may be mixed with the hydroxyl group-containing polyether compound (A) and the bifunctional or more iso(thio)cyanate compound (B) before polymerizing the prepolymer.

[0024] The optical component of this embodiment is constructed using a polymerizable composition. The components included in the optical component (polymerizable composition) will be described below.

[0025] (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.

[0026] 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.

[0027] The above-mentioned polyethers are not particularly limited, but examples include polyethylene glycol, polypropylene glycol, or polybutylene glycol.

[0028] The above-mentioned polyesters are not particularly limited, but include those obtained from the condensation of dicarboxylic acids and diols.

[0029] Examples of the dicarboxylic acids mentioned above include adipic acid, succinic acid, or combinations thereof.

[0030] 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.

[0031] Examples of the polyesters mentioned above include polycaprolactone, polybutyrolactone, polyvalerolactone, polylactic acid, polyglycolic acid, or combinations thereof.

[0032] The polycarbonates mentioned above are not particularly limited, but examples include those obtained by condensation between a carbonate and a diol.

[0033] 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.

[0034] 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.

[0035] The polyamides mentioned above are not particularly limited, but examples include those obtained by the condensation of a dicarboxylic acid and a diamine.

[0036] Examples of the dicarboxylic acids mentioned above include adipic acid, succinic acid, or combinations thereof. Examples of the diamines mentioned above include hexamethylenediamine.

[0037] Examples of polyamides mentioned above include lactams such as polycaprolactam.

[0038] The polyethyleneimines mentioned above include polyethyleneimine chains, polypropionyl aziridine chains, polyacetyl aziridine chains, and polyformyl aziridine chains, among others, as polymer chains.

[0039] Examples of the polysiloxanes mentioned above, which are polymer chains, include polydimethylsiloxane chains and polymethylphenylsiloxane chains.

[0040] The above polysulfide may include polyethylene sulfide chains, etc.

[0041] Examples of the polyolefins mentioned above include polyethylene, polypropylene, and combinations thereof.

[0042] The polystyrenes mentioned above include polystyrene, polystyrene sulfonate, and combinations thereof.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] (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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] [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.

[0051] 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.

[0052] [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.

[0053] [Photochromic compound (E)] Photochromic compounds (E) include compounds whose absorption properties (absorption spectrum) change in response to light of a specific wavelength. The photochromic compound (E) in this embodiment can be any known compound, 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.

[0054] [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.

[0055] (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.

[0056] (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.

[0057] (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.

[0058] <Method for manufacturing optical components> Next, an example of a method for manufacturing the optical component of this embodiment will be described.

[0059] The method for manufacturing the optical component of this embodiment includes the following steps. • Step 1 (Mixing step): A mixing step in which a hydroxyl group-containing polyether compound (A), a bifunctional or more iso(thio)cyanate compound (B), and a photochromic compound (E) are mixed. Step 2 (First polymerization step): 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. Step 3 (Second polymerization step): A second polymerization step in which the obtained prepolymer is mixed with a bifunctional or more active hydrogen compound (C) and a catalyst (D), and polymerized and cured.

[0060] The details of each step are explained below.

[0061] [Process 1 (mixing process)] First, a hydroxyl group-containing polyether compound (A), an isocyanate compound (B), and a photochromic compound (E) are mixed together.

[0062] This makes it possible to obtain optical components with photochromic properties.

[0063] 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).

[0064] 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.

[0065] [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.

[0066] 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.

[0067] 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.

[0068] 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).

[0069] After the prepolymer is obtained, it is preferable to cool the mixture to room temperature (25°C) or below.

[0070] 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.

[0071] 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.

[0072] [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.

[0073] 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.

[0074] When mixing the active hydrogen compound (C) and the catalyst (D), the temperature is preferably below room temperature, more preferably 15-20°C.

[0075] 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.

[0076] Furthermore, in the second polymerization step, the polymerizable composition may be further mixed with the other additives mentioned above (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.

[0077] Furthermore, an iso(thio)cyanate compound (B) may be added in the second polymerization step. This can increase the polymerization rate during polymerization curing.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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).

[0083] [Applications, Optical Lenses] Examples of optical components in 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. They are particularly suitable as optical materials or optical elements such as plastic lenses, camera lenses, light-emitting diode lenses, and light-emitting diode lens cases. Among these, it is especially preferable to use an optical lens comprising an optical component.

[0084] The plastic lens (optical 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.

[0085] 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.

[0086] 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.

[0087] 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]

[0088] 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.

[0089] (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

[0090] [Measurement of haze value (%)] A haze meter (model number: NDH 2000) manufactured by Nippon Denshoku Industries Co., Ltd. was used to measure the haze value (%).

[0091] (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

[0092] [Photochromic compound (E)] Photochromic compound (E); Reversacol Wembley Grey (R1966): 500 ppm

[0093] (3) Fabrication of optical components and photochromic lenses (molded samples) <Example 1> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (E) 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.

[0094] <Example 2> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (E) 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 tine dichloride were added beforehand and uniformly dissolved to prepare a solution. This solution was added to the solution after 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 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.

[0095] <Example 3> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (E) 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 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.

[0096] <Comparative Example 1> A master solution was prepared by dissolving 0.05 parts by weight of photochromic compound (E) 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. To 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, 10 parts by weight of the resulting master solution was added 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. (First 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 first solution 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 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] [Table 1]

Claims

1. An optical component comprising a hydroxyl group-containing polyether compound (A), a bifunctional or more iso(thio)cyanate compound (B), a bifunctional or more active hydrogen compound (C), a catalyst (D), and a photochromic compound (E), An optical component having a haze (%) of 0.58% / mm or more relative to its thickness (mm) at the center of the optical component.

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

3. The optical member 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.

4. The optical member 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.

5. The optical member 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.

6. The 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.

7. 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(mercaptomethyl) The optical component according to claim 1 or 2, comprising one or more polythiols selected from the group consisting of lucaptoethyl) 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).

8. The optical member according to claim 1 or 2, wherein the photochromic compound (E) is a naphthopyran compound that does not contain active hydrogen.

9. The optical member according to claim 1 or 2, wherein the photochromic compound (E) is one or more selected from naphthopyrane compounds and spiropyran compounds.

10. An optical lens comprising the optical member described in claim 1 or 2.

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