Polymerizable compositions for optical components, cured products, and spectacle lenses

Abstract

One embodiment of the present disclosure relates to a polymerizable composition for optical components, a cured product thereof, and an eyeglass lens containing the cured product, which yields a cured product having a moderate refractive index and a high Abbe number. [Solution] One embodiment of the present disclosure relates to a polymerizable composition for optical components containing an epithio compound (1) having an ether bond and an epithio compound (2) having a thioether bond or a dithioether bond.

Description

Technical Field

[0001] The present disclosure relates to a polymerizable composition for optical members, a cured product, and a spectacle lens.

Background Art

[0002] Conventionally, plastic spectacle lenses have been widely known. As a material for spectacle lenses, polythiourethane resin is used (for example, Patent Document 1). Since polythiourethane resin is a material having a moderate refractive index, it forms a spectacle lens with a moderate thickness, and is widely used as it easily ensures processability and impact resistance.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of Invention

Problems to be Solved by the Invention

[0004] Epithio resin is generally known as a material having a high refractive index and a high Abbe number. Since epithio resin has a high refractive index, it can form a thin spectacle lens. On the other hand, in consideration of processability and impact resistance, a relatively thick lens may be required in some cases. For example, for resins for optical members such as polythiourethane resin, it is considered a problem that the Abbe number decreases when the refractive index becomes lower as compared with epithio resin and the like. Note that the Abbe number is an index representing the degree of dependence of the refractive index on the wavelength of light, and an increased Abbe number can reduce chromatic aberration of the spectacle lens.

[0005] An embodiment of the present disclosure relates to a polymerizable composition for optical members, which can provide a cured product having a moderate refractive index and a high Abbe number, the cured product thereof, and a spectacle lens including the cured product.

Means for Solving the Problems

[0006] The inventors have discovered that by using a compound represented by formula (1) and a compound represented by formula (2) as a polymerizable composition for optical components, a cured product having an appropriate refractive index and a high Abbe number can be obtained.

[0007] One embodiment relating to this disclosure is, Epitio compound (1) having an ether bond, Epithio compound (2) having a thioether bond or a dithioether bond, This invention relates to a polymerizable composition for optical components that contains [specific ingredient].

[0008] The inventors have found that by using an epithio compound (1) with a refractive index of less than 1.55 and an epithio compound (2) with a refractive index of 1.60 or higher as a polymerizable composition for optical components, a cured product with an appropriate refractive index and a high Abbe number can be obtained.

[0009] One embodiment relating to this disclosure is, Epitio compounds with a refractive index of less than 1.55 (1'), This invention relates to a polymerizable composition for optical components containing an epithio compound (2') with a refractive index of 1.60 or higher. [Effects of the Invention]

[0010] According to one embodiment of the present disclosure, it is possible to provide a polymerizable composition for optical components, a cured product thereof, and an eyeglass lens containing the cured product, which yield a cured product having a moderate refractive index and a high Abbe number. [Modes for carrying out the invention]

[0011] The embodiments of this disclosure (hereinafter referred to as "these embodiments") will be described in detail below, but the present invention is not limited thereto, and various modifications are possible without departing from the spirit thereof. In this specification, for example, the notation of a numerical range "1 to 100" includes both the lower limit "1" and the upper limit "100". The same applies to the notation of other numerical ranges.

[0012] [Polymerizable composition for optical member] One embodiment according to the present disclosure relates to an epithio compound (1) having an ether bond, and an epithio compound (2) having a thioether bond or a dithioether bond, and relates to a polymerizable composition for optical members containing the same. According to the polymerizable composition for optical members according to one embodiment of the present disclosure, a cured product having a moderate refractive index and a high Abbe number can be obtained.

[0013] As a material for spectacle lenses, polythiourethane resins are used because they have a refractive index of 1.64 or more and 1.68 or less, and also have high heat resistance. Since polythiourethane resin is a material having a refractive index of 1.64 or more and 1.68 or less, it provides spectacle lenses of moderate thickness, is easy to secure processability and impact resistance, and is widely used. For example, although polythiourethane resins can achieve a moderate refractive index of 1.64 or more and 1.68 or less, their low Abbe number is a challenge. The Abbe number is an index representing the degree of dependence of the refractive index on the wavelength of light, and a higher Abbe number can reduce the chromatic aberration of spectacle lenses.

[0014] One embodiment of the present disclosure relates to a polymerizable composition for optical members that can provide a cured product having a refractive index of 1.64 or more and 1.68 or less and a high Abbe number, a cured product thereof, and a spectacle lens containing the cured product. A polymerizable composition for optical members according to one embodiment of the present disclosure is Formula (1): [Chemical Formula] (In the formula, R 1 is a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms.) and a compound represented by Formula (2): [Chemical Formula] (In the formula, a is an integer of 0 to 1, R is a divalent hydrocarbon group having 1 to 10 carbon atoms, b is an integer of 0 to 1, and n is an integer of 0 to 2.) and a compound represented by is contained. The polymerizable composition for optical members according to one embodiment of the present disclosure can provide a cured product having a refractive index of 1.64 or more and 1.68 or less and a high Abbe number.

[0015] <Epithio compound (1)> The epithio compound (1) has an ether bond. In the epithio compound (1), the number of ether bonds is preferably 1 to 5, more preferably 1 to 3, and still more preferably 2.

[0016] The epithio compound (1) is preferably Formula (1):

Chemical Formula

[0017] R 1 The aliphatic hydrocarbon group may be linear, branched, or cyclic, but is preferably linear. The carbon number of R 1 is preferably 1 to 10, more preferably 1 to 6, and still more preferably 1 to 3. Examples of the divalent aliphatic hydrocarbon group for R 1 include a methylene group, an ethylenediyl group, and a propanediyl group.

[0018] The epithio compound (1) is preferably Formula (1-1):

Chemical Formula

[0019] The refractive index of epithio compound (1) is preferably less than 1.55, more preferably 1.54 or less, and even more preferably 1.53 or less. Here, the refractive index of epithio compound (1) refers to the epithio compound (1) before polymerization. The refractive index is a value measured by the d line (587.6 nm). The refractive index is measured according to the measurement method of the examples. Hereafter, the refractive index of various epithio compounds will be measured by the same method.

[0020] The content of epithio compound (1) is preferably 5% to 95% by mass, more preferably 10% to 80% by mass, even more preferably 25% to 75% by mass, and even more preferably 35% to 60% by mass, based on the total amount of polymerizable composition for optical components.

[0021] <Epicio compounds (2)> The epithio compound (2) has a thioether bond or a dithioether bond. The number of thioether bonds or dithioether bonds in the epithio compound (2) is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. A thioether bond refers to a chemical structure represented as *-S-* (where * represents the bonding site). A geoether bond refers to a chemical structure represented as *-SS-* (where * represents the bonding site).

[0022] The epithio compound (2) is preferably Formula (2): [ka] This is a compound represented by the formula (wherein a is an integer between 0 and 1, R is a divalent hydrocarbon group having 1 to 10 carbon atoms, b is an integer between 0 and 1, and n is an integer between 0 and 2). The number of carbon atoms in R is preferably 1 to 4, more preferably 2 or 3. Examples of divalent hydrocarbons of R include ethylene, propylene, and butylene groups.

[0023] Examples of epithio compound (2) include, for example, bis(β-epithiopropyl) sulfide, bis(β-epithiopropyl) dithioether, bis(β-epithiopropyl) trisulfide, bis(β-epithiopropylthio) methane, 1,2-bis(β-epithiopropylthio)ethane, 1,3-bis(β-epithiopropylthio)propane, 1,3-bis(β-epithiopropyloxy)propane, 1,4-bis(β-epithiopropylthio)butane, and bis(β-epithiopropylthioethyl) sulfide. Among these, bis(β-epithiopropyl) sulfide and bis(β-epithiopropyl) dithioether are preferred, and bis(β-epithiopropyl) sulfide is more preferred. In other words, epithio compound (2) is given by the following formula (2-1): [ka] It is more preferable that the compound is represented by [formula].

[0024] The refractive index of epithio compound (2) is preferably 1.60 or higher, and more preferably 1.61 or higher.

[0025] The refractive index difference between epithio compound (1) and epithio compound (2) is preferably less than 0.10, more preferably 0.09 or less, and even more preferably 0.08 or less. Having a refractive index difference of less than 0.10 suppresses the occurrence of clouding during polymerization. Alternatively, the refractive index difference between epithio compound (1) and epithio compound (2) is preferably 0.01 or more, more preferably 0.03 or more, and even more preferably 0.05 or more.

[0026] The content of epithio compound (2) is preferably 5% to 95% by mass, more preferably 10% to 80% by mass, more preferably 25% to 75% by mass, and even more preferably 40% to 65% by mass, based on the total amount of polymerizable composition for optical components.

[0027] The total content of epithio compound (1) and epithio compound (2) may be 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of polymerizable composition for optical components.

[0028] One embodiment relating to this disclosure is, Epitio compounds with a refractive index of less than 1.55 (1'), This invention relates to a polymerizable composition for optical components containing an epithio compound (2') with a refractive index of 1.60 or higher. A polymerizable composition for optical components according to one embodiment of the present disclosure yields a cured product having a refractive index of 1.64 or more and 1.68 or less, and a high Abbe number.

[0029] <Epicio compound (1')> The epithio compound (1') has a refractive index of less than 1.55. The refractive index of the epithio compound (1') is preferably 1.54 or less, and more preferably 1.53 or less. Examples of epithio compounds (1') include those shown in epithio compound (1) above.

[0030] The content of epithio compound (1') is preferably 5% to 95% by mass, more preferably 10% to 80% by mass, even more preferably 25% to 75% by mass, and even more preferably 35% to 60% by mass, based on the total amount of polymerizable composition for optical components.

[0031] <Epicio compound (2')> The epithio compound (2') has a refractive index of 1.60 or higher. Preferably, the refractive index of the epithio compound (2') is 1.61 or higher. Examples of epithio compounds (2') include those shown in epithio compound (2) above.

[0032] The content of the epithio compound (2') is preferably 5% to 95% by mass, more preferably 10% to 80% by mass, more preferably 25% to 75% by mass, and even more preferably 40% to 65% by mass, based on the total amount of the polymerizable composition for optical components.

[0033] The refractive index difference between epithio compound (1') and epithio compound (2') is preferably less than 0.10, more preferably 0.09 or less, and even more preferably 0.08 or less. A refractive index difference of less than 0.10 suppresses the occurrence of clouding during polymerization. The refractive index difference between epithio compound (1') and epithio compound (2') is preferably 0.01 or more, more preferably 0.03 or more, and even more preferably 0.05 or more.

[0034] The total content of epithio compound (1') and epithio compound (2') may be 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of polymerizable composition for optical components.

[0035] Polymerizable compositions for optical components may contain other monomers. Examples of other monomers include polythiol compounds.

[0036] Examples of polythiol compounds include ester compounds of polyol compounds and mercapto group-containing carboxylic acid compounds, linear or branched aliphatic polythiol compounds, polythiol compounds having an alicyclic structure, and polythiol compounds having an aromatic ring structure.

[0037] In ester compounds of polyol compounds and mercapto group-containing carboxylic acid compounds, the polyol compound can be a compound having two or more hydroxyl groups in its molecule. Examples of polyol compounds include ethylene glycol, diethylene glycol, propanediol, propanetriol, butanediol, trimethylolpropane, bis(2-hydroxyethyl)dithioether, pentaerythritol, and dipentaerythritol. Examples of mercapto group-containing carboxylic acid compounds include thioglycolic acid, mercaptopropionic acid, thiolactic acid compounds, and thiosalicylic acid. Examples of ester compounds of polyol compounds and mercapto group-containing carboxylic acid compounds include ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), 1,4-butanediol bis(2-mercaptoacetate), and 1,4-butanediol bis(3-mercaptopropionate). Examples include topropionate, trimethylolpropantris (2-mercaptoacetate), trimethylolpropantris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (2-mercaptoacetate), and dipentaerythritol hexakis (3-mercaptopropionate).

[0038] Examples of linear or branched aliphatic polythiol compounds include 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethyloxybutane-1,2-dithiol, 2,3-dimercapto-1-propanol, 1,2- Dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, 2-(2-mercaptoethylthio)propane-1,3-dithiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(mercaptomethylthio)methane, tris(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio )ethane, 1,3-bis(mercaptomethylthio)propane, 1,3-bis(2-mercaptoethylthio)propane, 1,1,2,2-tetrakis(mercaptoethylthio)ethane, 1,1,3,3-tetrakis(mercaptoethylthio)propane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tetrakis(mercaptoethylthio)propane, bis(2-mercaptoethyl)ether, bis(2-mercaptoethyl Examples include sulfides, bis(2-mercaptoethyl)dithioether, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol.

[0039] Examples of polythiol compounds having an alicyclic structure include 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, methylcyclohexanedithiol, bis(mercaptomethyl)cyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiethane, 2,5-bis(mercaptomethyl)-1,4-dithiane, and 4,8-bis(mercaptomethyl)-1,3-dithiane.

[0040] Examples of polythiol compounds having an aromatic ring structure include 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene, 1,3,5-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptoethyl)benzene, 4,4'-dimercaptobiphenyl, and 4,4'-dimercapto Examples include bibenzyl, 2,5-toluenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2,7-naphthalenedithiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracene dimethanethiol, 1,3-di(p-methyloxyphenyl)propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, and 2,4-di(p-mercaptophenyl)pentane. These may be used individually or in combination of two or more types.

[0041] The polythiol compound content in the polymerizable composition for optical components is preferably 2% by mass or more, more preferably 4% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 10% by mass or less.

[0042] Polymerizable compositions for optical components preferably contain a polymerization catalyst. Examples of polymerization catalysts include nitrogen-containing compounds.

[0043] Examples of nitrogen-containing compounds include tertiary amines, quaternary ammonium salts, imidazole compounds, and pyrazole compounds. Tertiary amines are preferably hindered amines.

[0044] Examples of tertiary amines include triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, N,N-dimethylbenzylamine, N-methylmorpholine, N,N-dimethylcyclohexylamine, pentamethyldiethylenetriamine, bis(2-dimethylaminoethyl) ether, N-methylmorpholine, N,N'-dimethylpiperazine, N,N,N',N'-tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane (DABCO).

[0045] Examples of hindered amines include 1,2,2,6,6-pentamethyl-4-piperidinol, 1,2,2,6,6-pentamethyl-4-hydroxyethyl-4-piperidinol, methyl-1,2,2,6,6-pentamethyl-4-piperidyl sebacate, a mixture of methyl-1,2,2,6,6-pentamethyl-4-piperidyl sebacate and bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, and bis(1,2,2,6,6 Examples include pentamethyl-4-piperidyl) sebacate, bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate, and tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate.

[0046] An example of a quaternary ammonium salt is tetraethylammonium hydroxide. Examples of imidazole compounds include imidazole, 1-methyl-2-mercapto-1H-imidazole, 1,2-dimethylimidazole, benzylmethylimidazole, and 2-ethyl-4-imidazole. Examples of pyrazole compounds include pyrazole and 3,5-dimethylpyrazole. Among these, tertiary amines such as hindered amines, imidazole compounds, and pyrazole compounds are preferred, imidazole compounds are more preferred, and 1-methyl-2-mercapto-1H-imidazole is even more preferred.

[0047] The amount of polymerization catalyst added to the polymerizable composition is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, even more preferably 0.007 parts by mass or more, and preferably 2 parts by mass or less, more preferably 1 part by mass or less, and even more preferably 0.5 parts by mass or less, based on 100 parts by mass of the total amount of polymerizable components.

[0048] [Cured product] The polymerizable composition for optical components according to this embodiment is used as a cured product. The refractive index nd of the polymerizable composition for optical components after curing is preferably 1.64 to 1.68. The refractive index nd of the cured product is measured using the d line (587.6 nm). The refractive index nd is measured according to the measurement method of the example.

[0049] The cured Abbe number νd of the polymerizable composition for optical components may be, for example, 37 or higher, 38 or higher, 39 or higher, or 43 or higher. The measurement of the Abbe number νd is performed according to the measurement method of the examples.

[0050] It is preferable that the cured material has linear thermal expansion characteristics. Linear thermal expansion characteristics make it less likely for cracks to occur when applying a coating layer or the like to the surface of the cured material.

[0051] Applications of the cured product of this embodiment include, for example, eyeglass lenses (materials for lens substrates), prisms, optical fibers, information recording substrates, and filters. Among these applications, eyeglass lenses are preferred, and lens substrates are more preferred. The cured product may be obtained by thermal curing or by photocuring.

[0052] [Lens substrates and eyeglass lenses] The lens substrate used for eyeglass lenses may be either a finished lens or a semi-finished lens. The surface shape of the lens substrate is not particularly limited and may be a flat, convex, concave, or any other shape. The lens substrate of this disclosure may be any of the following: a single-focus lens, a multifocal lens, a progressive power lens, etc. For example, in the case of a progressive power lens, the near-vision region (near-vision portion) and the progressive region (intermediate region) are usually included in the aforementioned lower region, and the far-vision region (far-vision portion) is included in the upper region. While colorless materials are typically used as lens substrates, colored materials can also be used as long as they do not impair transparency.

[0053] The thickness and diameter of the lens substrate are not particularly limited, but the thickness is usually about 1 to 30 mm and the diameter is usually about 50 to 100 mm. The refractive index of the lens substrate is preferably 1.64 to 1.68.

[0054] The lens substrate includes the cured product described above.

[0055] <Method for manufacturing lens substrates> The lens substrate is not particularly limited, but for example, The process of curing the polymerizable composition for optical components described above, and The process of annealing the resin after curing. It is obtained by a manufacturing method that includes [the following].

[0056] Polymerization is preferably carried out by casting polymerization. The lens substrate is obtained, for example, by injecting a polymerizable composition for optical components into a mold that combines a glass or metal mold with a tape or gasket and carrying out polymerization.

[0057] Polymerization conditions can be appropriately set depending on the polymerizable composition for optical components. The polymerization start temperature is preferably 0°C or higher, more preferably 10°C or higher, preferably 50°C or lower, and more preferably 40°C or lower. It is preferable to raise the temperature from the polymerization start temperature and then heat to cure and form the material. For example, the maximum temperature to be raised is usually 110°C or higher and 130°C or lower.

[0058] After polymerization is complete, the lens substrate may be released from the mold and annealed. The annealing temperature is preferably 100 to 150°C.

[0059] As described above, this disclosure provides a polymerizable composition for optical components, a cured product thereof, and an eyeglass lens containing the cured product, which yield a cured product having an appropriate refractive index and a high Abbe number. The cured product has a refractive index in the range of 1.64 to 1.68 and exhibits a high Abbe number, making it suitable for use as a lens substrate in eyeglass lenses.

[0060] This disclosure provides the following embodiments. <1> Epitio compound (1) having an ether bond, Epithio compound (2) having a thioether bond or a dithioether bond, A polymerizable composition for optical components containing the following: <2> The content of the epithio compound (1) is 5% to 95% by mass relative to the total amount of the polymerizable composition for optical components. <1> Polymerizable composition for optical components as described above. <3> The content of the epithio compound (2) is 5% to 95% by mass relative to the total amount of the polymerizable composition for optical components. <1> or <2> Polymerizable composition for optical components as described above. <4> The epithio compound (1) is Formula (1): [ka] (In the formula, R 1 It is a compound represented by a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. <1> ~ <3> A polymerizable composition for optical components as described in any of the following. <5> The epithio compound (1) is Formula (1-1): [ka] The compound represented by <4> Polymerizable composition for optical components as described above. <6> The epithio compound (2) is Formula (2): [ka] The compound is represented by the formula (wherein a is an integer between 0 and 1, R is a divalent hydrocarbon group having 1 to 10 carbon atoms, b is an integer between 0 and 1, and n is an integer between 0 and 2). <1> ~ <5> A polymerizable composition for optical components as described in any of the following. <7> The epithio compound (2) is The following equation (2-1): [ka] The compound represented by <6> Polymerizable composition for optical components as described above. <8> The epithio compound (1) has a refractive index of less than 1.55. The epithio compound (2) has a refractive index of 1.60 or higher. <1> ~ <7> A polymerizable composition for optical components as described in any of the following. <9> The refractive index difference between the epithio compound (1) and the epithio compound (2) is less than 0.10. <8> Polymerizable composition for optical components as described above. <10> Epitio compounds with a refractive index of less than 1.55 (1'), A polymerizable composition for optical components containing an epithio compound (2') with a refractive index of 1.60 or higher. <11> The refractive index difference between epithio compound (1') and epithio compound (2') is less than 0.10. <10> Polymerizable composition for optical components as described above. <12> The refractive index of the polymerizable composition for optical components after curing is 1.64 to 1.68. <1> ~ <11> A polymerizable composition for optical components as described in any of the following. <13> The Abbe number of the polymerizable composition for optical components after curing is 37 or higher. <1> ~ <12> A polymerizable composition for optical components as described in any of the following. <14> <1> ~ <13> A cured product of a polymerizable composition for optical components as described in any of the following. <15> <14> An eyeglass lens comprising a lens substrate containing the cured product described above. [Examples]

[0061] The present invention will be described in more detail below using examples and comparative examples. However, the present invention is not limited in any way by the following examples.

[0062] [Measurement method] <Refractive index and Abbe number> The refractive index of hardened or compound spectacle lenses was measured at 25°C using a precision refractometer "KPR-2000" (manufactured by Carnew Optical Industry Co., Ltd.) at the F line (486.1 nm), C line (656.3 nm), and d line (587.6 nm). The Abbe number was then calculated using the following formula. Abbe number νd = (nd-1) / (nF-nC) nd is the refractive index measured on the d-line, nF is the refractive index measured on the F-line, and nC is the refractive index measured on the C-line.

[0063] <Thermal expansion characteristics> Using a thermomechanical analyzer "Thermo Plus EVO2 TMA8310" (manufactured by Rigaku Corporation), the thermal expansion characteristics were measured by heating the sample from room temperature (25°C) to 150°C using the penetration method (sample thickness 3 mm, pin diameter 0.5 mm, load 10 g, heating rate 10°C / min). If no peaks or inflection points were observed in the thermal expansion characteristics, it was classified as "linear," and if peaks or inflection points were observed, it was classified as "non-linear."

[0064] <Absorption peaks in the ultraviolet region> The ultraviolet absorption peak was confirmed using a spectrophotometer "U-4100" (product name, manufactured by Hitachi, Ltd.). The measurement point for the ultraviolet absorption peak was the optical center of the spectacle lens.

[0065] <Manufacturing Example 1> 87.00 g of ethylene glycol diglycidyl ether and 76.12 g of thiourea were dissolved in 250 mL of toluene and 250 mL of methanol, and 1.50 g of acetic acid was added to prepare a reaction mixture solution, which was then reacted at room temperature (25°C) for 18 hours. 500 mL of toluene was added to the reaction mixture, and 500 mL of water in which 1.00 g of NaCl was dissolved was added. The aqueous layer and the organic layer were separated, and the organic layer was removed. The organic layer was washed with 300 mL of 1% by mass aqueous sulfuric acid solution. The organic layer was then washed seven times with 330 mL of water, and the organic layer was removed. To obtain a colorless and transparent ethylene glycol-bis(β-epithiopropyl) ether (refractive index (nd; 25℃) = 1.53).

[0066] <Example 1> 50.00 g of bis-(β-epithiopropyl) sulfide (refractive index (nd; 25℃) = 1.61), 50.00 g of ethylene glycol-bis(β-epithiopropyl) ether, and 5.00 g of bismercaptoethyldithiane were added to 300 ml of Nasufura, 0.15 g of tetrabutylphosphonium bromide as a catalyst, and 0.10 g of 2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole as an ultraviolet absorber. The mixture was mixed, dissolved, and homogenized. Degassing was performed while stirring to remove gases contained during mixing. The mixture was then injected into lens molding molds (set to 0.00D center wall thickness 1.8 mm and -4.00D center wall thickness 1.0 mm) made of glass mold and resin gasket, while being filtered through a polytetrafluoroethylene (PTFE) filter with a pore size of 0.45 microns. Polymerization was carried out in an electric furnace at 20℃ to 110℃ for 24 hours. After polymerization was complete, the gasket and mold were removed, and the lens substrate was heat-treated at 105°C for 2 hours. The optical properties of the obtained lens substrate were measured, and the results are shown in Table 1.

[0067] <Examples 2-3> A resin composition was obtained using the same additive formulation and procedure as in Example 1, except that the amounts of bis-(β-epithiopropyl) sulfide and ethylene glycol-bis(β-epithiopropyl) ether were as shown in Table 1.

[0068] <Comparative Example 1> A resin composition was obtained using the same additive formulation and procedure as in Example 1, except that it contained 100.00 g of bis-(β-epithiopropyl) sulfide and did not include ethylene glycol-bis(β-epithiopropyl) ether.

[0069] <Comparative Example 2> 50.60 g of xylylene diisocyanate was added as the isocyanate compound, 0.10 g of 2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole as an ultraviolet absorber, 0.14 g of a 4:6 mixture of monobutoxyethyl acid phosphate and dibutoxyethyl acid phosphate as a mold release agent, and 0.01 g of dimethyl tine dichloride as a catalyst. The mixture was then mixed and dissolved. 49.40 g of a structural isomer mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-diol was added, and the mixture was stirred and mixed under reduced pressure of 666 Pa (5 mmHg) for 30 minutes to prepare a curable composition. This curable composition was then injected into a lens molding mold consisting of a glass mold and a resin gasket similar to those used in the examples, while filtering through a PTFE filter with a pore size of 5 microns. Polymerization was carried out in an electric furnace at a temperature of 20°C to 120°C for 24 hours. After polymerization was complete, the gasket and mold were removed, and the lens substrate was heat-treated at 120°C for 2 hours. The optical properties of the obtained lens substrate were measured, and the results are shown in Table 1.

[0070] [Table 1]

[0071] From the above results, the polymerizable composition of the example exhibits a high Abbe number while having a moderate refractive index. Furthermore, because the cured product of the polymerizable composition according to the example has linear thermal expansion properties, it is easy to laminate other layers onto the surface of a lens substrate or the like.

Claims

1. Epitio compound (1) having an ether bond, Epithio compound (2) having a thioether bond or a dithioether bond, A polymerizable composition for optical components containing the following:

2. The polymerizable composition for optical components according to claim 1, wherein the content of the epithio compound (1) is 5% by mass to 95% by mass based on the total amount of the polymerizable composition for optical components.

3. The polymerizable composition for optical components according to claim 1, wherein the content of the epithio compound (2) is 5% by mass to 95% by mass based on the total amount of the polymerizable composition for optical components.

4. The epithio compound (1) is Formula (1): 【Chemistry 1】 (In the formula, R １ The polymerizable composition for optical components according to claim 1, wherein is a compound represented by ), where is a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms.

5. The epithio compound (1) is Formula (1-1): 【Chemistry 2】 A polymerizable composition for optical components according to claim 4, wherein the compound is represented by [the formula shown].

6. The epithio compound (2) is Formula (2): 【Transformation 3】 A polymerizable composition for optical components according to claim 1, which is a compound represented by the formula (wherein a is an integer from 0 to 1, R is a divalent hydrocarbon group having 1 to 10 carbon atoms, b is an integer from 0 to 1, and n is an integer from 0 to 2).

7. The epithio compound (2) is The following equation (2-1): 【Chemistry 4】 A polymerizable composition for optical components according to claim 6, wherein the compound is represented by [the formula shown].

8. The epithio compound (1) is Formula (1): 【Transformation 5】 (In the formula, R １ This is a compound represented by a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. The epithio compound (2) is Formula (2): 【Transformation 6】 A polymerizable composition for optical components according to claim 1, which is a compound represented by the formula (wherein a is an integer from 0 to 1, R is a divalent hydrocarbon group having 1 to 10 carbon atoms, b is an integer from 0 to 1, and n is an integer from 0 to 2).

9. The epithio compound (1) is Formula (1-1): 【Transformation 7】 It is a compound represented by the following: The epithio compound (2) is The following equation (2-1): 【Transformation 8】 A polymerizable composition for optical components according to claim 1, wherein the compound is represented by [the formula shown].

10. The epithio compound (1) has a refractive index of less than 1.

55. The polymerizable composition for optical components according to claim 1, wherein the epithio compound (2) has a refractive index of 1.60 or higher.

11. The polymerizable composition for optical components according to claim 10, wherein the refractive index difference between the epithio compound (1) and the epithio compound (2) is less than 0.

10.

12. Epithio compounds with a refractive index of less than 1.55 (1'), A polymerizable composition for optical components containing an epithio compound (2') with a refractive index of 1.60 or higher.

13. The polymerizable composition for optical components according to claim 12, wherein the refractive index difference between epithio compound (1') and epithio compound (2') is less than 0.

10.

14. The polymerizable composition for optical components according to claim 1, wherein the refractive index of the polymerizable composition for optical components after curing is 1.64 to 1.

68.

15. The polymerizable composition for optical components according to claim 14, wherein the Abbe number after curing of the polymerizable composition for optical components is 37 or more.

16. A cured product of a polymerizable composition for optical components according to any one of claims 1 to 15.

17. An eyeglass lens comprising a lens substrate containing the cured product described in claim 16.

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