Ultraviolet absorber and spectacle lens

Abstract

An ultraviolet absorber containing a compound (1) represented by formula (1) (in the formula, R1 is an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-12 carbon atoms, m is 0 or 1, n is 0 or 1, and R2 is an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-12 carbon atoms); the peak area ratio of a compound (2) represented by formula (2) (in the formula, R1 is an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-12 carbon atoms, m is 0 or 1, and R2 is an alkyl group having 1-12 carbon atoms or an alkoxy group having 1-12 carbon atoms) in a pattern obtained by measuring the ultraviolet absorber by liquid chromatography using a diode array detector is 0.01% or less.

Description

Technical Field

[0001] This disclosure relates to ultraviolet absorbers and eyeglass lenses. Background Technology

[0002] In eyeglass lenses, blocking light in the blue light region (wavelength range of 380-500nm) reduces glare, improves visual acuity and contrast. Furthermore, because blue light (380-500nm) has high energy, it can cause damage to the retina and other parts of the eye. Damage caused by blue light is called "blue light hazard," with the lower wavelength range of 380-420nm being the most dangerous; blocking light in this region is desirable.

[0003] Patent document 1 describes an optical material containing one or more ultraviolet absorbers (a) with a maximum absorption peak in the range of 350 nm or more and 370 nm or less, and whose transmittance measured with a thickness of 2 mm satisfies the following characteristics (1) to (3): (1) transmittance at a wavelength of 410 nm is less than 10%, (2) transmittance at a wavelength of 420 nm is less than 70%, and (3) transmittance at a wavelength of 440 nm is more than 80%.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: International Publication No. WO2014 / 133111 Summary of the Invention

[0007] The problem that the invention aims to solve

[0008] According to conventional eyeglass lenses as shown in Patent Document 1, the transmittance of light at a wavelength of 410 nm can be suppressed by containing a specific ultraviolet absorber. However, generally speaking, ultraviolet absorbers that exhibit light absorption characteristics at a wavelength of 410 nm also absorb light of nearby wavelengths. 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole can be cited as such an ultraviolet absorber, but it deteriorates over time due to storage, etc., thus presenting the problem of unnecessarily discoloring to yellow.

[0009] One embodiment of this disclosure relates to a color-blocking ultraviolet absorber and an eyeglass lens.

[0010] Methods for solving problems

[0011] One embodiment of this disclosure relates to an ultraviolet absorber containing compound (1) of formula (1).

[0012] [Chemical Formula 1]

[0013]

[0014] (in the formula,

[0015] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0016] m is 0 or 1.

[0017] n is 0 or 1,

[0018] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0019] In the chromatogram obtained by liquid chromatography using a diode array detector to determine the above-mentioned ultraviolet absorber, the peak area ratio of compound (2) shown in formula (2) is less than 0.01%.

[0020] [Chemical Formula 2]

[0021]

[0022] (in the formula,

[0023] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0024] m is 0 or 1.

[0025] n is 0 or 1,

[0026] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0027] One embodiment of this disclosure relates to an eyeglass lens having a lens substrate comprising the aforementioned ultraviolet absorber and resin.

[0028] One embodiment of this disclosure relates to a method for manufacturing ultraviolet absorber crystals, which is a method for manufacturing ultraviolet absorber crystals containing compound (1) as shown in formula (1).

[0029] [Chemical Formula 3]

[0030]

[0031] (in the formula,

[0032] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0033] m is 0 or 1.

[0034] n is 0 or 1,

[0035] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0036] This method has:

[0037] The process of adding isopropanol solution to a toluene solution containing the above-mentioned ultraviolet absorber to obtain crystals, and

[0038] The process of washing the crystals with isopropanol.

[0039] The effects of the invention

[0040] According to one embodiment of this disclosure, a UV absorber that inhibits coloration and eyeglass lenses can be provided. Attached Figure Description

[0041] Figure 1 This is a schematic cross-sectional view of the spectacle lens 1 of this embodiment. Detailed Implementation

[0042] Hereinafter, embodiments of the present disclosure will be described in detail with reference to the accompanying drawings, but the present disclosure is not limited thereto, and various modifications can be made without departing from its spirit. It should be noted that in the drawings, the same symbols are used for the same elements, and repeated descriptions are omitted. Furthermore, unless otherwise specified, positional relationships such as up, down, left, and right are based on the positional relationships shown in the drawings. In addition, the scale of the drawings is not limited to the scale shown in the illustrations.

[0043] It should be noted that in this specification, the description of a numerical range, such as "1~100", includes both the lower limit "1" and the upper limit "100". The same applies to the description of other numerical ranges.

[0044] In addition, "cured product of isocyanate component and active hydrogen compound component" does not exclude other components, but refers to a cured product formed by curing a composition containing at least isocyanate component and active hydrogen compound component.

[0045] UV absorber

[0046] The ultraviolet absorber of this embodiment contains compound (1) as shown in formula (1).

[0047] [Chemical Formula 4]

[0048]

[0049] (in the formula,

[0050] R1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0051] m is 0 or 1.

[0052] n is 0 or 1,

[0053] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0054] In the chromatogram obtained by liquid chromatography using a diode array detector to determine the above-mentioned ultraviolet absorber, the peak area ratio of compound (2) shown in formula (2) is less than 0.01%.

[0055] [Chemical Formula 5]

[0056]

[0057] (in the formula,

[0058] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0059] m is 0 or 1.

[0060] n is 0 or 1,

[0061] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0062] Based on the aforementioned ultraviolet absorbers, ultraviolet absorbers that inhibit coloration and eyeglass lenses can be provided.

[0063] In the formula, R 1 The alkyl group or alkoxy group having 1 to 12 carbon atoms is preferred, more preferably 2 to 8, and even more preferably 4 to 8. The alkyl group and alkoxy group can be branched or straight-chain. Alkoxy groups are preferred among the alkyl and alkoxy groups.

[0064] Examples of alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, n-octyl, 1,1,3,3-tetramethylbutyl, nonyl, decyl, undecyl, and dodecyl.

[0065] Examples of alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecyloxy, and dodecyloxy. Methoxy or ethoxy is preferred.

[0066] In the formula, R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms. R 2 Examples of alkyl and alkoxy groups in R 1 The examples are the same.

[0067] m can be 0 or 1, preferably 0.

[0068] n can be 0 or 1, preferably 1.

[0069] The preferred compound (1) is compound (1-1) as shown in formula (1-1).

[0070] [Chemical Formula 6]

[0071]

[0072] Compound (2) is compound (2-1) shown in formula (2-1).

[0073] [Chemical Formula 7]

[0074] .

[0075] (Peak area ratio)

[0076] The peak area ratio of compound (2) represented by formula (2) in the spectrum obtained by liquid chromatography using a diode array detector of the ultraviolet absorber of this embodiment is 0.01% or less. By setting this peak area ratio, the coloration of the ultraviolet absorber can be suppressed.

[0077] From the same point of view, the peak area ratio is preferably 0.01% or less, more preferably 0.009% or less, and even more preferably 0.008% or less. The peak area ratio can, for example, be 0.001% or more.

[0078] The peak area ratio of compound (1) represented by formula (1) in the spectrum obtained by liquid chromatography using a diode array detector to determine the ultraviolet absorber of this embodiment is preferably 95% or more, more preferably 98% or more, and even more preferably 99% or more.

[0079] The determination was performed using liquid chromatography with a diode array detector, according to the method described in the examples.

[0080] To achieve the aforementioned peak area, the ultraviolet absorber can be purified by repeated recrystallization using toluene and isopropanol.

[0081] More specifically, for a toluene solution of a 5-10% concentration of ultraviolet absorber, 40-60% by volume of isopropanol is added relative to the toluene solvent to prepare a mother liquor for recrystallization. Then, the temperature is lowered to allow recrystallization. Further, the resulting recrystallization is removed and washed with isopropanol. By performing these steps, an ultraviolet absorber having the aforementioned peak area ratio can be obtained.

[0082] [Eyeglass lenses]

[0083] The spectacle lens of this embodiment comprises a lens substrate containing the aforementioned ultraviolet absorber and resin. The spectacle lens of this embodiment may have a layer selected from at least one of a hard coating layer, a base layer, and an anti-reflective layer.

[0084] Figure 1 This is a schematic cross-sectional view of the spectacle lens 1 according to this embodiment. The spectacle lens 1 according to this embodiment includes: a lens substrate 11, a hard coating 21f disposed on the object-side surface 11a of the lens substrate 11, a functional layer 31f disposed on the object-side surface 21fa of the hard coating 21f, and a water-repellent layer 41f disposed on the object-side surface 31fa of the functional layer 31f.

[0085] In addition, when the lens substrate 11 is a finished lens, the spectacle lens 1 of this embodiment further includes: a hard coating 21b disposed on the eyeball side surface 11b of the lens substrate 11, a functional layer 31b disposed on the eyeball side surface 21bb of the hard coating 21b, and a water-repellent layer 41b disposed on the eyeball side surface 31bb of the functional layer 31b.

[0086] It should be noted that, although not shown in the figure, a base layer may be provided between the lens substrate 11 and the hard coating 21f, or between the lens substrate 11 and the hard coating 21b.

[0087] <Lens Substrate>

[0088] The lens substrate contains the aforementioned ultraviolet absorber and resin.

[0089] Preferably, the spectacle lens contains 0.05 parts by weight and 2.00 parts by weight of compound 1 relative to 100 parts by weight of the resin in the lens substrate. From the viewpoint of further suppressing the transmittance of light with a wavelength of 410 nm, the content of the ultraviolet absorber relative to 100 parts by weight of the resin in the lens substrate is preferably 0.10 parts by weight and 2.00 parts by weight, more preferably 0.15 parts by weight and 1.50 parts by weight, and even more preferably 0.20 parts by weight and 1.00 parts by weight.

[0090] [Resin]

[0091] Examples of resins used as lens substrates include: urethane resins, cyclosulfide resins, polycarbonate resins, and acrylic resins.

[0092] The resin is preferably selected from at least one of polyurethane resin, polysulfide resin and polyurethane resin, and more preferably from at least one of polyurethane resin and polysulfide resin.

[0093] (Carbamate resins)

[0094] Carbamate resins are cured products of polymerizable compositions containing isocyanate components and active hydrogen compound components. Examples of carbamate resins include: thiocarbamate resins containing polymerization sites of isocyanate and polythiol components; carbamate resins containing polymerization sites of isocyanate and polyol components; and carbamate urea resins having polythiourethane sites as polymerization sites of isocyanate and polythiol or polyol components, and polyurea sites as polymers of isocyanate and polyamine components.

[0095] (Isocyanate component)

[0096] Examples of isocyanate components include: polyisocyanate compounds with aromatic rings, polyisocyanate compounds with aliphatic rings, and linear or branched aliphatic polyisocyanate compounds.

[0097] Examples of polyisocyanate compounds with aromatic rings include: phenyl diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, ethyl phenyl diisocyanate, isopropyl phenyl diisocyanate, dimethyl phenyl diisocyanate, diethyl phenyl diisocyanate, diisopropyl phenyl diisocyanate, trimethyl phenyl triisocyanate, phenyl triisocyanate, biphenyl diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-methylene bis(2-methylphenyl isocyanate), bibenzyl-4,4'-diisocyanate, bis(isocyanate phenyl)ethylene, 1,3-bis(isocyanate methyl)benzene, 1,4-bis(isocyanate methyl)benzene, 1,3-bis(isocyanate ethyl)benzene, bis(isocyanate propyl)benzene, α, α,α',α'-Tetramethylphenyl dimethyl diisocyanate, bis(isocyanate butyl)benzene, bis(isocyanate methyl)naphthalene, bis(isocyanate methylphenyl) ether, 2-isocyanate phenyl-4-isocyanate phenyl sulfide, bis(4-isocyanate phenyl) sulfide, bis(4-isocyanate methylphenyl) sulfide, bis(4-isocyanate phenyl) disulfide, bis(2-methyl-5-isocyanate phenyl) disulfide, bis(3-methyl-5-isocyanate phenyl) disulfide, bis(3-methyl-6-isocyanate phenyl) disulfide, bis(4-methyl-5-isocyanate phenyl) disulfide, bis(3-methoxy-4-isocyanate phenyl) disulfide, bis(4-methoxy-3-isocyanate phenyl) disulfide.

[0098] Examples of polyisocyanate compounds with aliphatic rings include: 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, 1,3-bis(isocyanate methyl)cyclohexane, 1,4-bis(isocyanate methyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, dicyclohexylmethane-2,4'-diisocyanate, 2,5-bis(isocyanate methyl)bicyclo[ [2.2.1] Heptane, 2,6-bis(isocyanate methyl)bicyclo[2.2.1] heptane, 2,5-diisocyanate-1,4-dithiane, 2,5-bis(isocyanate methyl)-1,4-dithiane, 4,5-diisocyanate-1,3-dithiopentane, 4,5-bis(isocyanate methyl)-1,3-dithiopentane, 4,5-bis(isocyanate methyl)-2-methyl-1,3-dithiopentane.

[0099] Examples of linear or branched aliphatic polyisocyanate compounds include: pentamethylene diisocyanate, hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecane triisocyanate, and 1,3,6-hexamethylene diisocyanate. Methyl triisocyanate, 4-methyl octane-1,8-diisocyanate, bis(ethyl isocyanate) carbonate, bis(ethyl isocyanate) ether, lysine diisocyanate methyl ester, lysine triisocyanate, bis(methyl isocyanate) sulfide, bis(ethyl isocyanate) sulfide, bis(propyl isocyanate) sulfide, bis(hexyl isocyanate) sulfide, bis(methyl isocyanate) sulfone, bis(isocyanate) Di(isocyanate methyl) disulfide, bis(isocyanate ethyl) disulfide, bis(isocyanate propyl) disulfide, bis(isocyanate methylthio)methane, bis(isocyanate ethylthio)methane, bis(isocyanate methylthio)ethane, 2-isocyanate methyl-3-pentane-1,5-diisocyanate, 1,2,3-tris(isocyanate methylthio)propane, 1,2, 3-Tris(isocyanate ethylthio)propane, 3,5-dithio-1,2,6,7-heptane tetraisocyanate, 2,6-diisocyanate methyl-3,5-dithio-1,7-heptane diisocyanate, 2,5-diisocyanate methylthiophene, 4-isocyanate ethylthio-2,6-dithio-1,8-octane diisocyanate, 1,2-diisothiocyanate ethane, 1,6-diisothiocyanate hexane.

[0100] These can be used in one or more ways.

[0101] The isocyanate component preferably comprises at least one selected from bis(isocyanate methyl)bicyclo[2.2.1]heptane, bis(isocyanate methyl)cyclohexane, bis(isocyanate methyl)benzene, toluene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and pentamethylene diisocyanate (hereinafter also referred to as "preferred isocyanate compounds").

[0102] Examples of bis(isocyanate methyl)bicyclo[2.2.1]heptane include one or more selected from 2,5-bis(isocyanate methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate methyl)bicyclo[2.2.1]heptane, preferably a mixture of 2,5-bis(isocyanate methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate methyl)bicyclo[2.2.1]heptane.

[0103] Examples of bis(isocyanate methyl)cyclohexane include 1,3-bis(isocyanate methyl)cyclohexane and 1,4-bis(isocyanate methyl)cyclohexane. 1,3-bis(isocyanate methyl)cyclohexane is preferred.

[0104] Examples of bis(isocyanate methyl)benzene include 1,3-bis(isocyanate methyl)benzene and 1,4-bis(isocyanate methyl)benzene. 1,3-bis(isocyanate methyl)benzene is preferred.

[0105] Examples of toluene diisocyanates include 2,4-toluene diisocyanate and 2,6-toluene diisocyanate. Among them, 2,4-toluene diisocyanate is preferred.

[0106] Examples of diphenylmethane diisocyanates include 4,4'-diphenylmethane diisocyanate and 2,4'-diphenylmethane diisocyanate.

[0107] Examples of dicyclohexylmethane diisocyanates include dicyclohexylmethane-4,4'-diisocyanate.

[0108] In the isocyanate component, the content of the above-mentioned "preferred isocyanate compound" is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more and 100% by mass or less.

[0109] (Active hydrogen compound component)

[0110] Examples of active hydrogen compounds include polythiols, polyols, and polyamines.

[0111] (Polythiol component)

[0112] Examples of polythiols include: ester compounds formed from polyol compounds and thiol-containing carboxylic acid compounds; straight-chain or branched aliphatic polythiols; polythiols with aliphatic rings; and polythiols with aromatic rings.

[0113] Among ester compounds formed by polyol compounds and mercaptocarboxylic acid compounds, compounds having two or more hydroxyl groups within their molecules can be listed as polyol compounds. Examples of polyol compounds include: ethylene glycol, diethylene glycol, propylene glycol, glycerol, butanediol, trimethylolpropane, bis(2-hydroxyethyl) disulfide, pentaerythritol, and dipentaerythritol.

[0114] Examples of compounds containing thiocarboxylic acids include: thioacetic acid, thiopropionic acid, thiolactic acid compounds, and thiosalicylic acid.

[0115] Examples of ester compounds formed from polyol compounds and mercaptocarboxylic 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), 1,4-butanediol bis(3-mercaptopropionate), trimethylolpropane tri(2-mercaptoacetate), trimethylolpropane tri(3-mercaptopropionate), pentaerythritol tetra(2-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), dipentaerythritol hexa(2-mercaptoacetate), and dipentaerythritol hexa(3-mercaptopropionate).

[0116] Examples of linear or branched aliphatic polythiols 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-dimethoxybutane-1,2-dithiol, and 2,3-dimercapto-1-propanediol. Alcohols, 1,2-dimercaptopropylmethyl ether, 2,3-dimercaptopropylmethyl ether, dimercaptoethyl ether, 2-(2-mercaptoethylthio)propane-1,3-dithiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(mercaptomethylthio)methane, tri(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane 1,3-Di(2-mercaptoethylthio)ethane, 1,3-bis(mercaptomethylthio)propane, 1,1,2,2-tetra(mercaptoethylthio)ethane, 1,1,3,3-tetra(mercaptoethylthio)propane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tetra(mercaptoethylthio)propane, bis(2-mercaptoethyl) ether, bis(2-mercaptoethyl) sulfide, Bis(2-mercaptoethyl) disulfide, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol.

[0117] Examples of polythiols with aliphatic rings include: 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, methylcyclohexanedithiol, bis(mercaptomethyl)cyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithionecyclobutane, 2,5-bis(mercaptomethyl)-1,4-dithiane, and 4,8-bis(mercaptomethyl)-1,3-dithiane.

[0118] Examples of polythiols with aromatic rings 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'-dimercaptobibenzyl. 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-Anthracenedimethylthiol, 1,3-Di(p-methoxyphenyl)propane-2,2-dithiol, 1,3-Diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-Di(p-mercaptophenyl)pentane.

[0119] These can be used in one or more ways.

[0120] (Polyol components)

[0121] Examples of polyols include: ethylene glycol, diethylene glycol, propylene glycol, glycerol, butanediol, trimethylolpropane, bis(2-hydroxyethyl) disulfide, pentaerythritol, and dipentaerythritol.

[0122] (Polyamine components)

[0123] Examples of polyamine components include: polymethylene diamine, polyether diamine, diethylenetriamine, iminodipropylamine, bis(hexamethylenetriamine), diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, pentaethylenehexamine, dimethylaminopropylamine, aminoethylethanolamine, methyliminodipropylamine, montanane diamine, N-aminomethylpiperazine, 1,3-diaminocyclohexane, isophorone diamine, m-phenylenediamine, tetrachloro-p-phenylenediamine, m-phenylenediamine, 4,4'-methylenediphenylamine, diaminodiphenyl sulfone, benzidine, diaminodiphenyl ether, 4,4'-thiodiphenylamine, 4,4'-bis(o-methylaniline)dianisidine, o-phenylenediamine, 2,4-toluenediamine, 2,5 - Toluenediamine, methylene bis(o-chloroaniline), diaminoxylenyl sulfone, bis(3,4-diaminophenyl) sulfone, 2,6-diaminopyridine, 4-chloroo-phenylenediamine, 4-methoxy-6-methyl-m-phenylenediamine, m-aminobenzylamine, N,N,N',N'-tetramethyl-1,3-butanediamine, N,N,N',N'-tetramethyl-p-phenylenediamine, tetramethylguanidine, 2-dimethylamino-2-hydroxypropane, pyrazine, 2,4,6-tris(dimethylaminohydroxymethyl)phenol, N-methylpiperazine, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethyldimethoxysilane.

[0124] The active hydrogen compound preferably comprises at least one selected from toluene diamine, pentaerythritol tetramercaptoacetate, pentaerythritol tetramercaptopropionate, trimethylolpropane trimercaptoacetate, trimethylolpropane trimercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiadecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol.

[0125] Examples of toluene diamines include 2,4-toluene diamine and 2,5-toluene diamine.

[0126] Examples of pentaerythritol tetramercaptoacetate include pentaerythritol tetra(2-mercaptoacetate).

[0127] Examples of pentaerythritol tetramercaptopropionate include pentaerythritol tetra(3-mercaptopropionate).

[0128] Examples of trimethylolpropane trimercaptoacetic acid esters include trimethylolpropane tri(2-mercaptoacetic acid ester).

[0129] Examples of trimethylolpropane trimercaptopropionate include trimethylolpropane tri(3-mercaptopropionate).

[0130] Examples of bis(mercaptoethio)mercaptopropane include, for instance, 1,2-bis(2-mercaptoethio)-3-mercaptopropane.

[0131] Examples of bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol include, for example, 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. A mixture of 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 is preferred.

[0132] The active hydrogen compound component is preferably a polythiol component.

[0133] Regarding polythiols...

[0134] Preferably, it comprises a compound selected from 2,5-bis(mercaptomethyl)-1,4-dithiane, pentaerythritol tetra(2-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol. At least one of the following: 1,1-dithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), butanediol bis(2-mercaptoacetate), butanediol bis(3-mercaptopropionate), dipentaerythritol hexa(2-mercaptoacetate), and dipentaerythritol hexa(3-mercaptopropionate).

[0135] More preferably, it comprises at least one selected from 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane, pentaerythritol tetra(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, and pentaerythritol tetra(2-mercaptoacetate).

[0136] Further preferably, it comprises at least one selected from 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.

[0137] A mixture comprising 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 is further preferred.

[0138] The amount of the preferred polythiol component is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 90% by mass or more, even more preferably 95% by mass or more, and less than 100% by mass.

[0139] The equivalence ratio (thiol / isocyanate group) of the polythiol component to the isocyanate group of the polyisocyanate component is preferably 40 / 60 or more, more preferably 43 / 57 or more, even more preferably 45 / 55 or more, and preferably 60 / 40 or less, more preferably 55 / 45 or less, even more preferably 53 / 47 or less.

[0140] The total content of the polythiol component and the polyisocyanate component in the polymerizable composition is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, and is less than 100% by mass.

[0141] (Epoxy sulfur resin)

[0142] Cyclosulfide resins are cured products of polymeric compositions containing cyclosulfide compounds. Here, the polymeric composition may contain other monomers.

[0143] (cyclic sulfur compounds)

[0144] Cyclic sulfur compounds are compounds that have a cyclic sulfide group (epithio-).

[0145] Examples of cyclic sulfur compounds include: cyclic sulfur compounds having a straight or branched aliphatic skeleton, cyclic sulfur compounds having an alicyclic skeleton, cyclic sulfur compounds having an aromatic skeleton, and cyclic sulfur compounds having a dithiane cyclic skeleton.

[0146] Examples of cyclic sulfur compounds with a straight-chain or branched aliphatic skeleton include: bis(β-cyclothiopropyl) sulfide, bis(β-cyclothiopropyl) disulfide, 2-(2-β-cyclothiopropylthioethylthio)-1,3-bis(β-cyclothiopropylthio)propane, 1,2-bis[(2-β-cyclothiopropylthioethyl)thio]-3-(β-cyclothiopropylthio)propane, tetra(β-cyclothiopropylthiomethyl)methane, and 1,1,1-tris(β-cyclothiopropylthiomethyl)propane.

[0147] Examples of cyclosulfide compounds with an alicyclic skeleton include: 1,3-bis(β-cyclothiopropylthio)cyclohexane, 1,4-bis(β-cyclothiopropylthio)cyclohexane, 1,3-bis(β-cyclothiopropylthiomethyl)cyclohexane, 1,4-bis(β-cyclothiopropylthiomethyl)cyclohexane, bis[4-(β-cyclothiopropylthio)cyclohexyl]methane, 2,2-bis[4-(β-cyclothiopropylthio)cyclohexyl]propane, and bis[4-(β-cyclothiopropylthio)cyclohexyl]sulfide.

[0148] Examples of cyclic sulfur compounds with aromatic skeletons include: 1,3-bis(β-cyclothiopropylthio)benzene, 1,4-bis(β-cyclothiopropylthio)benzene, 1,3-bis(β-cyclothiopropylthiomethyl)benzene, 1,4-bis(β-cyclothiopropylthiomethyl)benzene, bis[4-(β-cyclothiopropylthio)phenyl]methane, 2,2-bis[4-(β-cyclothiopropylthio)phenyl]propane, bis[4-(β-cyclothiopropylthio)phenyl]sulfide, bis[4-(β-cyclothiopropylthio)phenyl]sulfonate, and 4,4-bis(β-cyclothiopropylthio)biphenyl.

[0149] Examples of cyclic sulfur compounds having a dithiane ring skeleton include: 2,5-bis(β-cyclothiopropylthiomethyl)-1,4-dithiane, 2,5-bis(β-cyclothiopropylthioethylthiomethyl)-1,4-dithiane, 2,5-bis(β-cyclothiopropylthioethyl)-1,4-dithiane, and 2,3,5-tris(β-cyclothiopropylthioethyl)-1,4-dithiane.

[0150] In addition to cyclic sulfur compounds, other polymeric components such as the aforementioned polyisocyanates and polythiols can also be added.

[0151] Preferably, the compound is a cyclic sulfur compound having a straight-chain or branched aliphatic skeleton, more preferably a bis(β-cyclothiopropyl) sulfide or a bis(β-cyclothiopropyl) disulfide.

[0152] The content of the cyclic sulfur compound in the polymerizable composition is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, and preferably 98% by mass or less, even more preferably 96% by mass or less.

[0153] The polymerizable composition preferably contains sulfur or polythiol compounds in combination with cyclic sulfur compounds.

[0154] The sulfur content in the polymeric composition is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less.

[0155] Examples of polythiols can be cited above.

[0156] When used in combination with cyclic sulfur compounds, the content of polythiol compounds in the polymerizable component 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, further preferably 30% by mass or less, further preferably 20% by mass or less, and further preferably 10% by mass or less.

[0157] In the case of polymerizable compositions containing polyisocyanate and polythiol components, or cyclic sulfur compounds, a polymerization catalyst is preferably included.

[0158] Examples of polymerization catalysts include tin compounds and nitrogen-containing compounds.

[0159] Examples of tin compounds include alkyltin compounds and alkyltin halides.

[0160] Examples of alkyltin compounds include dibutyltin diacetate and dibutyltin dilaurate.

[0161] Examples of alkyl tin halide compounds include: dibutyltin dichloride, dimethyltin dichloride, monomethyltin trichloride, trimethyltin chloride, tributyltin chloride, tributyltin fluoride, and dimethyltin dibromide.

[0162] The preferred materials are dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, and dimethyltin dichloride, with dimethyltin dichloride being more preferred.

[0163] Examples of nitrogen-containing compounds include tertiary amines, quaternary ammonium salts, imidazole compounds, and pyrazole compounds. Tertiary amines are preferably hindered amines.

[0164] 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).

[0165] 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-piperidinyl sebacate, mixtures of methyl-1,2,2,6,6-pentamethyl-4-piperidinyl sebacate and bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, bis(1,2, 2,6,6-pentamethyl-4-piperidinyl) sebacate, bis(2,2,6,6-tetramethyl-1-(octoxy)-4-piperidinyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidinyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl] butylmalonate, tetra(1,2,2,6,6-pentamethyl-4-piperidinyl)butane-1,2,3,4-tetracarboxylic acid ester.

[0166] Examples of quaternary ammonium salts include tetraethylammonium hydroxide.

[0167] Examples of imidazole compounds include: imidazole, 1-methyl-2-mercapto-1H-imidazol, 1,2-dimethylimidazol, benzylmethylimidazol, and 2-ethyl-4-imidazol.

[0168] Examples of pyrazole compounds include pyrazole and 3,5-dimethylpyrazole.

[0169] Preferably, the compound is a hindered tertiary amine, an imidazole compound, or a pyrazole compound; more preferably, an imidazole compound; and even more preferably, 1-methyl-2-mercapto-1H-imidazolium.

[0170] When the polymeric composition contains isocyanate and active hydrogen compound, the amount of polymerization catalyst added in the polymeric composition is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, and 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, relative to 100 parts by mass of the total amount of isocyanate and active hydrogen compound.

[0171] In the case of containing cyclic sulfur compounds, the amount of polymerization catalyst added in the polymerizable composition is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, and 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, relative to 100 parts by mass of the polymerizable components.

[0172] (Polycarbonate resin)

[0173] The polycarbonate resin is preferably a cured product of a polymeric composition comprising diethylene glycol dielyl carbonate.

[0174] To obtain a three-dimensionally cross-linked optical resin, the monomer preferably contains monomers having two or more polymerizable unsaturated bonds within the molecule.

[0175] Examples of polymerizable unsaturated bonds include (meth)acrylate, allyl, and vinyl groups. It should be noted that the (meth)acrylate group refers to at least one selected from methacrylate and acrylate groups.

[0176] Preferably, it is selected from at least one of methacrylate group and allyl group.

[0177] Monomers having two or more polymerizable unsaturated bonds within the molecule, preferably including diethylene glycol diallyl carbonate, more preferably including diethylene glycol diallyl carbonate, benzyl methacrylate, diallyl phthalate, and alkyl methacrylates with 1 to 4 carbon atoms in the alkyl group.

[0178] The amount of diethylene glycol dielyl carbonate relative to the total amount of monomer is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, preferably 100% by mass or less, more preferably 80% by mass or less, even more preferably 50% by mass or less, even more preferably 40% by mass or less.

[0179] When benzyl methacrylate, diallyl phthalate, and alkyl methacrylate with 1 to 4 carbon atoms in an alkyl group are used in combination, the amount of diethylene glycol diallyl carbonate relative to the total amount of monomer is more preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 20% by mass or more, more preferably 40% by mass or less, and more preferably 35% by mass or less.

[0180] The amount of benzyl methacrylate incorporated relative to the total amount of monomers is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less.

[0181] As diallyl phthalate, examples include one or both selected from diallyl isophthalate and diallyl terephthalate.

[0182] The amount of diallyl phthalate in combination relative to the total amount of monomers is preferably 14% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, preferably 88% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.

[0183] Alkyl methacrylates having 1 to 4 carbon atoms as alkyl groups can be listed as at least one of the following: methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, isobutyl methacrylate, and tert-butyl methacrylate.

[0184] The amount of alkyl methacrylate incorporation relative to the total amount of monomer is preferably 1% or more by mass, more preferably 2% or more by mass, further preferably 3% or more by mass, preferably 6% or less by mass, and more preferably 5% or less by mass.

[0185] Examples of free radical initiators used in polymerization include: 1,1-azobiscyclohexane carbonate, diisopropyl peroxide carbonate, 1,1'-azobiscyclohexane nitrate, and di-tert-butyl peroxide.

[0186] The amount of the free radical initiator relative to 100 parts by mass is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, even more preferably 1.0 parts by mass or more, preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and even more preferably 5 parts by mass or less.

[0187] (Acrylic resin)

[0188] Acrylic resin is a cured product of a polymeric composition containing an acrylic compound. Here, the polymeric composition may contain other monomers.

[0189] Examples of acrylic acid compounds include: polyfunctional (meth)acrylate compounds with aromatic rings, polyalkylene glycol di(meth)acrylates, monofunctional acrylates, etc.

[0190] Preferably, the compound comprises a polyfunctional (meth)acrylate compound having an aromatic ring and a polyalkylene glycol di(meth)acrylate.

[0191] Examples of polyfunctional (meth)acrylate compounds with aromatic rings include: epoxide-modified bisphenol A with (meth)acryloyl groups at both ends, and epoxide-modified and carbamate-modified bisphenol A with (meth)acryloyl groups at both ends.

[0192] Preferably, it is an epoxy-modified bisphenol A having (meth)acryloyl groups at both ends.

[0193] As an epoxy-modified bisphenol A having (meth)acryloyl groups at both ends, the compound shown in formula (51) is preferred.

[0194] [Chemical Formula 8]

[0195]

[0196] In the formula, R 51 It is ethylene or propylene, R 52 X is hydrogen or methyl, X is an oxygen atom or a sulfur atom, preferably an oxygen atom, m and n are the average molar number of additions, and m+n is 1.5~6, preferably 2~4.

[0197] Examples of epoxide-modified bisphenol A with (meth)acryloyl groups at both ends include 2,2-bis[4-[2-((meth)acryloyloxy)ethoxy]phenyl]propane and 2,2-bis[4-[2-((meth)acryloyloxy)ethoxy]-3,5-dibromophenyl]propane.

[0198] The content of the polyfunctional (meth)acrylate compound having an aromatic ring in the polymerizable composition is preferably 40% by mass or more, more preferably 50% by mass or more, even more preferably 55% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass or less.

[0199] Examples of polyalkylene glycol di(meth)acrylates include: diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, dibutylene glycol di(meth)acrylate, tributylene glycol di(meth)acrylate, and tetrabutylene glycol di(meth)acrylate.

[0200] The content of polyalkylene glycol di(meth)acrylate in the polymerizable composition is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and preferably 60% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less.

[0201] Examples of monofunctional (meth)acrylates include: phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, 2-phenylphenyl (meth)acrylate, 4-phenylphenyl (meth)acrylate, 3-(2-phenylphenyl)-2-hydroxypropyl (meth)acrylate, 3-(4-phenylphenyl)-2-hydroxypropyl (meth)acrylate, 1-naphthoxyethyl (meth)acrylate, 2-naphthoxyethyl (meth)acrylate, 2,4,6-tribromophenyl (meth)acrylate, 2,4,6-tribromophenoxyethyl (meth)acrylate, 2,4,6-tribromophenyl di(oxyethyl) ester (meth)acrylate, and 2,4,6-tribromobenzyl (meth)acrylate.

[0202] The total content of the polymerizable components in the polymerizable composition is preferably 80% by mass or more, more preferably 85% by mass or more, even more preferably 90% by mass or more, preferably 99% by mass or less, and more preferably 95% by mass or less.

[0203] Polymerizable compositions that contain acrylic compounds preferably contain a free radical polymerization initiator.

[0204] Examples of free radical polymerization initiators include energy line-sensitive polymerization initiators and thermally-sensitive polymerization initiators.

[0205] Examples of energy-line inductive polymerization initiators include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, hydroxycyclohexylphenyl ketone, methyl benzoylformate, and 2,4,6-trimethylbenzoyl diphenylphosphine oxide.

[0206] Examples of thermosensitive polymerization initiators include organic peroxides and azo compounds.

[0207] Examples of organic peroxides include: tert-butyl peroxyneodecanoate, tert-butyl peroxypentanoate, tert-butyl peroxyisobutyrate, tert-butyl peracetic acid, cumyl peroxyneodecanoate, tert-butyl peroxyoctanoate, tert-butyl peroxyisopropyl carbonate, cumyl peroxyoctanoate, tert-hexyl peroxyneodecanoate, tert-hexyl peroxypentanoate, and tert-butyl peroxyneohexanoate; 1,1-bis(tert-butylperoxyneodecanoate)- Peroxide ketals such as 3,3,5-trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)octane, and 2,2-bis(tert-butylperoxy)butane; peroxide diacyl groups such as peroxyacetyl, isobutyryl peroxide, octanoyl peroxide, lauroyl peroxide, benzoyl peroxide, and m-toluyl peroxide; and peroxide dicarbonates such as diisopropyl peroxide and di-n-propyl peroxide.

[0208] Examples of azo compounds include: 2,2'-azobisisobutyronitrile, 1,1'-azobis(cyclohexane-1-carboxylonitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4-dimethylpentanitrile), dimethyl 2,2'-azobisisobutyrate, and 2,2'-azobis(2,4,4-trimethylpentane).

[0209] The amount of free radical polymerization initiator added relative to 100 parts by mass of the acrylic compound is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.5 parts by mass or more, and preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less.

[0210] The lens substrate may contain mold release agents, colorants, antioxidants, anti-coloring agents, fluorescent whitening agents, and other additives. One or more of these may be used.

[0211] [Mold Release Agent]

[0212] Examples of release agents include: isopropyl phosphate, butyl phosphate, octyl phosphate, nonyl phosphate, decyl phosphate, isodecanyl phosphate, isodecanyl phosphate, tridecyl phosphate, stearyl phosphate, propylphenyl phosphate, butylphenyl phosphate, butoxyethyl phosphate, and other phosphate ester compounds. The phosphate ester compound can be any one of monophosphate or diester compounds, preferably a mixture of monophosphate and diester compounds.

[0213] The amount of release agent added relative to 100 parts by weight of the total amount of resin is preferably 0.01 parts by weight or more, preferably 0.05 parts by weight or more, preferably 1.00 parts by weight or less, and preferably 0.50 parts by weight or less.

[0214] [Coloring agent]

[0215] The lens substrate may contain colorants within a range that does not impair the light transmittance described later.

[0216] From the viewpoint of not making the coloring caused by the addition of the above-mentioned compound 1 noticeable, the lens substrate may contain a colorant L (hereinafter also referred to as "colorant L") having a maximum absorption wavelength of 550 nm or higher and 600 nm or lower in a toluene solution of 20 ppm by mass.

[0217] From the viewpoint of not making the coloring caused by the addition of the above-mentioned compound 1 noticeable, the lens substrate may contain a colorant S (hereinafter also referred to as "colorant S") having a maximum absorption wavelength of 500 nm or higher and less than 550 nm in a toluene solution of 20 ppm by mass.

[0218] (Coloring agent L)

[0219] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, colorant L exhibits a maximum absorption wavelength above 550 nm and below 600 nm in a 20 ppm toluene solution. It should be noted that 20 ppm toluene solution refers to the proportion of solute relative to the total toluene solution.

[0220] Furthermore, from the viewpoint of obtaining a lens substrate with a slightly bluish tint, the maximum absorption wavelength of the colorant L is preferably 550 nm or more, preferably 560 nm or more, and preferably 580 nm or more. Moreover, from the viewpoint of obtaining a resin composition with a slightly bluish tint, the maximum absorption wavelength of the colorant L is preferably 600 nm or less, and preferably 590 nm or less.

[0221] Examples of colorants L include: CI Solvent Violet 11, 13, 14, 26, 31, 33, 36, 37, 38, 45, 47, 48, 51, 59, 60; and CI Disperse Violet 26, 27, 28. Among these, CI Disperse Violet 27, CI Solvent Violet 13, and 31 are preferred. From the viewpoint that polymerization of polymerizable compositions results in high stability and minimal hue variation, CI Disperse Violet 27 and CI Solvent Violet 13 are more preferred, and CI Disperse Violet 27 is even more preferred.

[0222] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant L added relative to the resin is preferably 10,000 ppb by mass or less, more preferably 3,000 ppb by mass or less, and even more preferably 1,500 ppb by mass or less. From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant L added is preferably 200 ppb by mass or more, more preferably 300 ppb by mass or more, and even more preferably 400 ppb by mass or more.

[0223] (Colorant S)

[0224] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, colorant S has a maximum absorption wavelength above 500 nm and below 550 nm in a toluene solution of 20 ppm by mass.

[0225] Furthermore, from the viewpoint of obtaining a lens substrate with a slightly bluish tint, the maximum absorption wavelength of the colorant S is preferably 500 nm or more, more preferably 510 nm or more, and even more preferably 530 nm or more. Moreover, from the viewpoint of obtaining a lens substrate with a slightly bluish tint, the maximum absorption wavelength of the colorant L is preferably 545 nm or less.

[0226] From the viewpoint of obtaining a lens substrate with a slightly bluish hue, the following can be listed as colorants S: CI Solvent Red 24, 49, 52, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289. Among these, CI Solvent Red 52 and 146 are preferred, and CI Solvent Red 52 is more preferred from the viewpoint that it has high stability and less hue variation after polymerization of polymerizable compositions.

[0227] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant S added relative to the resin is preferably 500 ppb or less by mass, more preferably 100 ppb or less by mass, and even more preferably 50 ppb or less by mass. From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant S added is preferably 1 ppb or more by mass, more preferably 3 ppb or more by mass, and even more preferably 5 ppb or more by mass.

[0228] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the mass ratio of colorant L to colorant S [mass of colorant L / mass of colorant S] is preferably 5 or more and 500 or less.

[0229] The mass ratio of colorant L to colorant S is preferably 5 or more, more preferably 10 or more, more preferably 15 or more, and more preferably 20 or more. Furthermore, the mass ratio of colorant L to colorant S is preferably 500 or less, more preferably 200 or less, even more preferably 100 or less, and even more preferably 80 or less.

[0230] [Structure of lens substrate, etc.]

[0231] As a lens substrate, it can be either a finished lens or a semi-finished lens.

[0232] The surface shape of the lens substrate is not particularly limited and can be any shape such as flat, convex, or concave.

[0233] The lens substrate can also be used for any purpose, such as for monofocal lenses, multifocal lenses, or progressive lenses. For example, as an example, for progressive lenses, the near vision region (near region) and the progressive region (intermediate region) are usually included in the lower region mentioned above, and the distance vision region (distance region) is included in the upper region.

[0234] As a lens substrate, colorless lens substrates are usually used, but lens substrates that have been colored within a range that does not impair transparency can also be used.

[0235] The preferred lens substrate is meniscus-shaped. A "meniscus-shaped" lens substrate refers to a lens substrate with curved surfaces formed on both sides. By containing the aforementioned compound 1 in the meniscus-shaped lens substrate, astigmatism can be suppressed.

[0236] The optical center thickness of the lens substrate is not particularly limited, but is preferably 0.5 mm or more and 10.0 mm or less, more preferably 0.5 mm or more and 5.0 mm or less, even more preferably 0.5 mm or more and 3.0 mm or less, and even more preferably 0.5 mm or more and 2.0 mm or less.

[0237] There is no particular limitation on the diameter of the lens substrate, which is usually around 50~100mm.

[0238] The refractive index ne of the lens substrate is preferably 1.52 or higher, more preferably 1.53 or higher, even more preferably 1.55 or higher, even more preferably 1.58 or higher, and even more preferably 1.60 or higher.

[0239] From the viewpoint of improving the Abbe number increase brought about by the presence of compound 1, the refractive index ne of the lens substrate is preferably 1.70 or higher, more preferably 1.74 or higher.

[0240] It should be noted that there is no particular upper limit for the refractive index ne of the lens substrate; for example, it can be below 1.80.

[0241] From the perspective of mitigating the harmful effects of blue light, the transmittance of the lens substrate for light with a wavelength of 410 nm is preferably 5% or less, more preferably 3% or less, and even more preferably 1.0% or less. There is no particular limitation on the lower limit of the transmittance for light with a wavelength of 410 nm; for example, it may be 0.0% or more.

[0242] From the viewpoint of reducing the transmission of harmful ultraviolet rays, the transmittance of light with a wavelength of 400 nm in the lens substrate is preferably 3% or less, more preferably 1% or less, and even more preferably 0.0% or less.

[0243] The light transmittance of the lens substrate is preferably 70% or more, more preferably 80% or more, further preferably 85% or more, and even more preferably 90% or more. The upper limit of the light transmittance is not particularly limited and can be, for example, 100% or less or 95% or less.

[0244] The aforementioned transmittance refers to the transmittance at the optical center of the lens substrate, which can be measured using a spectrophotometer. For example, a UV-Vis-NIR spectrophotometer, "UH-4150" (trade name, manufactured by Hitachi High-Tech), can be used. The aforementioned transmittance can be achieved by adjusting the content of compound 1 according to the thickness of the lens substrate.

[0245] The YI value at the optical center of the lens substrate is preferably 10.00 or less, more preferably 9.70 or less, further preferably 9.00 or less, and even more preferably 8.70 or less. For example, the YI value can be measured at the optical center of the lens substrate using a spectrophotometer U-3500 manufactured by Hitachi, Ltd., according to JIS K 7373:2006.

[0246] [Manufacturing method of lens substrate]

[0247] The lens substrate is not particularly limited, and can be obtained, for example, by a manufacturing method including the following steps:

[0248] The process of curing the above-mentioned polymeric composition, and

[0249] The process of annealing the cured resin.

[0250] Polymerization is preferably carried out by casting polymerization. The lens substrate is obtained, for example, by injecting a polymerizable composition into a mold consisting of a glass or metal mold and a strip or gasket, and then polymerizing it.

[0251] The polymerization conditions can be appropriately set according to the polymerizability of the composition. The polymerization initiation temperature is preferably 0°C or higher, more preferably 10°C or higher, preferably 50°C or lower, more preferably 40°C or lower. It is preferable to start heating from the polymerization initiation temperature, and then heat and cure the product. For example, the maximum heating temperature is typically 110°C or higher and 130°C or lower.

[0252] After polymerization, the lens substrate can be demolded and annealed. The preferred annealing temperature is 100~150℃.

[0253] <Hard coating>

[0254] The hard coating is, for example, a cured film formed from a curable composition comprising inorganic oxides and silicon compounds. The curable composition preferably further comprises a multifunctional epoxy compound.

[0255] Examples of inorganic oxides include silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, tungsten oxide, zinc oxide, tin oxide, beryllium oxide, antimony oxide, and composite oxides formed from two or more of these inorganic oxides. These can be used individually or in combination. Among these inorganic oxides, silicon oxide is preferred. It should be noted that colloidal silicon dioxide can also be used as an inorganic oxide.

[0256] In the solid component of the curable composition, the content of inorganic oxides is preferably 20% by mass or more and 80% by mass or less, more preferably 25% by mass or more and 70% by mass or less, and even more preferably 25% by mass or more and 50% by mass or less.

[0257] The silicon compound is, for example, a silicon compound having hydrolyzable groups such as alkoxy groups. The silicon compound is preferably a silane coupling agent having organic groups bonded to silicon atoms and hydrolyzable groups. The organic groups bonded to silicon atoms are preferably organic groups having functional groups such as epoxy, vinyl, methacryloxy, acryloyloxy, mercapto, amino, phenyl, etc., and more preferably organic groups having epoxy groups. It should be noted that the silicon compound optionally has alkyl groups bonded to silicon.

[0258] Commercially available products of the aforementioned silane coupling agents include, for example, those manufactured by Shin-Etsu Chemical Industry Co., Ltd. under the trade names KBM-303, KBM-402, KBM-403, KBE-402, KBE-403, KBM-1403, KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-602, KBM-603, KBM-903, KBE-903, KBE-9103, KBM-573, KBM-575, KBM-9659, KBE-585, KBM-802, KBM-803, KBE-846, and KBE-9007.

[0259] In the solid component of the curable composition, the content of silicon compound is preferably 20% by mass or more and 90% by mass or less, more preferably 30% by mass or more and 75% by mass or less, and even more preferably 50% by mass or more and 75% by mass or less.

[0260] A polyfunctional epoxy compound is a polyfunctional epoxy compound containing two or more epoxy groups per molecule, more preferably a polyfunctional epoxy compound containing two or three epoxy groups per molecule. Commercially available polyfunctional epoxy compounds include those from the "Denacol" series manufactured by Nagase ChemteX, such as EX-201, EX-211, EX-212, EX-252, EX-313, EX-314, EX-321, EX-411, EX-421, EX-512, EX-521, EX-611, EX-612, EX-614, and EX-614B.

[0261] In the solid component of the curable composition, the content of the polyfunctional epoxy compound is preferably 0% by mass or more and 50% by mass or less, more preferably 10% by mass or more and 40% by mass or less, and even more preferably 15% by mass or more and 30% by mass or less.

[0262] In addition to the components described above, the curable composition can also be prepared by mixing any components such as organic solvents, leveling agents, and curing catalysts as needed.

[0263] The aforementioned hard coating can be formed by applying a curable composition to a substrate and then performing a curing process (thermal curing, photocuring, etc.). Common methods for applying the curable composition include dip coating, spin coating, and spray coating. For curable compositions containing polyfunctional epoxy compounds, curing is typically performed by heating. For example, heat curing can be performed by placing a lens coated with the aforementioned curable composition in a gas atmosphere at 50-150°C for approximately 30 minutes to 3 hours.

[0264] <Basal layer>

[0265] The aforementioned base layer may be formed, for example, from an aqueous resin composition comprising at least one resin particle selected from polyurethane resin, acrylic resin, and epoxy resin.

[0266] As for the above-mentioned waterborne resin composition, commercially available waterborne polyurethanes can be used directly, or they can be diluted with waterborne solvents as needed. Examples of commercially available waterborne polyurethanes include: the "Evafanol" series manufactured by Nichika Chemical Co., Ltd.; the "SuperFlex" series manufactured by Daiichi Kogyo Pharmaceutical Co., Ltd.; the "ADEKA Bontighter" series manufactured by ADEKA Co., Ltd.; the "Olester" series manufactured by Mitsui Chemicals Co., Ltd.; the "Bondic" series and "Hydran" series manufactured by Dai Nippon Ink & Chemical Co., Ltd.; the "Impranil" series manufactured by Bayer Co., Ltd.; and the "Sofuranate" series manufactured by Japan Sofuran Co., Ltd. The following brands are listed: "POIZ" series (manufactured by Kao Corporation), "SUNPRENE" series (manufactured by Sanyo Chemical Industries, Ltd.), and "Aizelux" series (manufactured by Hodogaya Chemical Industry Co., Ltd.). The NeoRez series, manufactured by Zeneca.

[0267] The base layer can be formed, for example, by applying the above-described aqueous resin composition to the surface of a substrate and allowing it to dry.

[0268] <Functional Layer>

[0269] Examples of the aforementioned functional layers include: anti-reflective layers, ultraviolet absorption layers, infrared absorption layers, photochromic layers, antistatic layers, and anti-fog layers. These functional layers can be used individually or in combination of two or more. Known technologies related to eyeglass lenses can be applied to these functional layers. An anti-reflective layer is preferred.

[0270] (Anti-reflective layer)

[0271] The anti-reflective layer has, for example, alternating low-refractive-index layers and high-refractive-index layers. The anti-reflective layer preferably has 4 to 11 layers, more preferably 5 to 8 layers.

[0272] The refractive index of the low-refractive-index layer is preferably 1.35 to 1.80, more preferably 1.45 to 1.50, at a wavelength of 500 to 550 nm. The low-refractive-index layer is formed of an inorganic oxide, preferably silicon oxide.

[0273] The refractive index of the high-refractive-index layer is preferably 1.90 to 2.60, more preferably 2.00 to 2.40, at a wavelength of 500 to 550 nm. The high-refractive-index layer is, for example, formed of an inorganic oxide. The inorganic oxide used in the high-refractive-index layer is preferably at least one selected from zirconium oxide, tantalum oxide, yttrium oxide, titanium oxide, niobium oxide, and aluminum oxide, more preferably at least one selected from zirconium oxide and tantalum oxide.

[0274] For anti-reflective layers, a vacuum evaporation method can be used to alternately stack low-refractive-index layers and high-refractive-index layers to form an anti-reflective layer.

[0275] <Water-repellent layer>

[0276] The water-repellent layer is formed using the water-repellent material composition described later. The water-repellent layer can be formed on a hard coating layer or a functional layer, and preferably on an anti-reflective layer. Furthermore, it is preferable that the water-repellent layer is located on the outermost surface.

[0277] <Properties of Spectacle Lenses>

[0278] From the perspective of mitigating the harmful effects of blue light, the overall transmittance of light with a wavelength of 410 nm in the eyeglass lenses is preferably 5% or less, more preferably 3% or less, and even more preferably 1.0% or less. There is no particular limitation on the lower limit of the transmittance of light with a wavelength of 410 nm; for example, it may be 0.0% or more.

[0279] From the viewpoint of reducing the transmission of harmful ultraviolet rays, the overall transmittance of light with a wavelength of 400 nm in the eyeglass lens is preferably 3% or less, more preferably 1% or less, and even more preferably 0.0% or less.

[0280] The light transmittance of the spectacle lens is preferably 70% or more, more preferably 80% or more, further preferably 85% or more, and even more preferably 90% or more. There is no particular upper limit to the light transmittance, and it can be, for example, 100% or less or 95% or less.

[0281] The aforementioned transmittance refers to the transmittance at the optical center of the spectacle lens, which can be measured using a spectrophotometer. For example, a UV-Vis-NIR spectrophotometer, "UH-4150" (trade name, manufactured by Hitachi High-Tech), can be used. The aforementioned transmittance can be achieved by adjusting the content of compound 1 according to the thickness of the spectacle lens.

[0282] The YI value at the optical center of the spectacle lens is preferably 10 or less, more preferably 9.70 or less, further preferably 9.00 or less, and even more preferably 8.70 or less. For example, the YI value can be measured at the optical center of the spectacle lens using a spectrophotometer U-3500 manufactured by Hitachi, Ltd., according to JIS K 7373:2006.

[0283] The following embodiments are disclosed in this specification.

[0284] <1>

[0285] An ultraviolet absorber containing compound (1) of formula (1),

[0286] [Chemical Formula 9]

[0287]

[0288] (in the formula,

[0289] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0290] m is 0 or 1.

[0291] n is 0 or 1,

[0292] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0293] In the chromatogram obtained by liquid chromatography using a diode array detector to determine the above-mentioned ultraviolet absorber, the peak area ratio of compound (2) shown in formula (2) is less than 0.01%.

[0294] [Chemical Formula 10]

[0295]

[0296] (in the formula,

[0297] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0298] m is 0 or 1.

[0299] n is 0 or 1,

[0300] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0301] <2>

[0302] According to the ultraviolet absorber described in <1>, wherein...

[0303] In the spectrum obtained by liquid chromatography using a diode array detector to determine the above ultraviolet absorber, the peak area ratio of the above compound (2) is 0.001% or more.

[0304] <3>

[0305] According to the ultraviolet absorber described in <1> or <2>, wherein,

[0306] In the spectrum obtained by liquid chromatography using a diode array detector to determine the above ultraviolet absorber, the peak area ratio of the above compound (1) is more than 99%.

[0307] <4>

[0308] The ultraviolet absorber according to any one of <1> to <3>, wherein...

[0309] The above compound (1) is compound (1-1) represented by formula (1-1).

[0310] [Chemical Formula 11]

[0311]

[0312] The above compound (2) is compound (2-1) shown in formula (2-1).

[0313] [Chemical Formula 12]

[0314] .

[0315] <5>

[0316] An eyeglass lens comprising a lens substrate containing any one of <1> to <4> of an ultraviolet absorber and a resin.

[0317] <6>

[0318] According to the spectacle lens described in <5>, wherein...

[0319] The above-mentioned resin is a cured product of isocyanate component and active hydrogen compound component, wherein the isocyanate component includes at least one selected from bis(isocyanate methyl)bicyclo[2.2.1]heptane, bis(isocyanate methyl)cyclohexane, bis(isocyanate methyl)benzene, toluene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate and pentamethylene diisocyanate.

[0320] <7>

[0321] According to the spectacle lens described in <6>, wherein...

[0322] The aforementioned active hydrogen compound contains at least one selected from toluene diamine, pentaerythritol tetramercaptoacetate, pentaerythritol tetramercaptopropionate, trimethylolpropane trimercaptoacetate, trimethylolpropane trimercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiadecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol.

[0323] <8>

[0324] According to the spectacle lens described in <7>, wherein...

[0325] The aforementioned bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol is a mixture of 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.

[0326] <9>

[0327] According to the spectacle lens described in <5>, wherein...

[0328] The resin mentioned above is an cyclic sulfur resin.

[0329] <10>

[0330] The spectacle lens as described in any one of <5> to <9>, wherein,

[0331] The above-mentioned compound (1) comprises 0.05 parts by mass and 2.00 parts by mass or less of the above-mentioned compound (1) relative to 100 parts by mass of the above-mentioned resin.

[0332] <11>

[0333] The spectacle lens according to any one of <5> to <10>, wherein,

[0334] The refractive index ne of the above-mentioned lens substrate is 1.52 or higher and 1.80 or lower.

[0335] <12>

[0336] The spectacle lens according to any one of <5> to <11>, wherein,

[0337] The refractive index ne of the above-mentioned lens substrate is 1.70 or higher and 1.80 or lower.

[0338] <13>

[0339] The spectacle lens according to any one of <5> to <12> has at least one layer selected from a hard coating layer, a base layer, and an anti-reflective layer.

[0340] <14>

[0341] A method for manufacturing ultraviolet absorber crystals, comprising a method for manufacturing ultraviolet absorber crystals containing compound (1) as shown in formula (1).

[0342] Equation (1):

[0343] [Chemical Formula 13]

[0344]

[0345] (in the formula,

[0346] R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0347] m is 0 or 1.

[0348] n is 0 or 1,

[0349] R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

[0350] This method has:

[0351] The process of adding isopropanol solution to a toluene solution containing the above-mentioned ultraviolet absorber to obtain crystals, and

[0352] The process of washing the crystals with isopropanol.

[0353] Example

[0354] The present invention will now be described in more detail using examples and comparative examples. It should be noted that the present invention is not limited to any of the examples described below.

[0355] [Liquid Chromatography-Fourier Transform Mass Analysis (LC / MS)]

[0356] The sample was collected into a screw-top bottle, and a chloroform / acetonitrile mixed solvent was added to prepare a solution with a sample concentration of approximately 1% by mass. The solution was filtered through a membrane filter, and the filtrate was analyzed by LC / MS under the following conditions.

[0357] <Conditions>

[0358] Apparatus: Vanquish / Orbitrap Exploris 120 liquid chromatography-Fourier transform mass analyzer (Thermo Fisher Scientific)

[0359] Chromatographic column: L-coulumn 3 C8 (2.1mm φ × 100mm, 3μm)

[0360] Eluent composition: Water / methanol gradient conditions (ammonium acetate addition conditions)

[0361] Elution buffer flow rate: 0.7 mL / min

[0362] Column temperature: 40℃

[0363] Detectors: FT-MS, diode array detector (DAD, 190-800nm)

[0364] Sample injection volume: 2 μL

[0365] Ionization method: ESI (m / z = 100~2000) (POS)

[0366] <Hazen color values ​​(APHA)>

[0367] The Hazen color value (APHA) of the ultraviolet absorber was determined according to JIS K0071-1:2017. Using colorimetric standard solution "1000" (manufactured by Fujifilm and Kojun Pharmaceutical Co., Ltd.), solutions of APHA values ​​of 0, 5, 10, 15, 20, and 25 were prepared by diluting with pure water, and calibration curves were constructed. A solution prepared by dissolving 3.5 g of the purified ultraviolet absorber in 50 g of toluene was filled into a quartz trough with a 50 mm optical path length, and the APHA was measured using a spectrophotometer "COH7700" (manufactured by Nippon Denshoku Kogyo Co., Ltd.).

[0368] <Light transmittance>

[0369] For light transmittance, the transmittance is measured at the optical center of the lens substrate using a UV-Vis-NIR spectrophotometer “UH-4150” (trade name, manufactured by Hitachi High-Tech Co., Ltd.) at a wavelength of 380~780nm. The value calculated according to the international standard ISO8980-4 for this wavelength region and taking into account the weight of relative visibility is used as the light transmittance (%).

[0370] <L ＊ a ＊ b ＊ Value and YI>

[0371] L of lens substrate ＊ a ＊ b ＊ L in the color system ＊ value, a ＊ value, b ＊The values ​​were measured using a Hitachi U-3500 spectrophotometer manufactured by Hitachi, Ltd. at the optical center of the lens substrate. The YI values ​​were determined according to JIS K 7373:2006.

[0372] <Example 1>

[0373] The amount of compound (2) contained in the UV absorber was determined by LC / MS as described above. The result showed that the peak area ratio of compound (2) was 0.033%. In addition, the APHA of the UV absorber was determined, and the result was 295.

[0374] Then, 7.0 g of the UV absorber and 100 cc of toluene were added to a 300 cc beaker and dissolved. 50 cc of isopropanol was then added and homogenized at room temperature (21°C). The mixture was then allowed to stand in a refrigerator at 5°C for 48 hours to recrystallize. After 48 hours, the UV absorber accumulated at the bottom of the beaker was removed using a Buchner funnel and washed by filtration with 200 cc of isopropanol cooled to 5°C. The pale yellow needle-like crystals of the UV absorber were dried in a hot air dryer at 60°C. Thus, 4.0 g of purified UV absorber was obtained. The amount of compound (2) contained in the UV absorber was determined by LC / MS as described above. The results showed that the peak area ratio of compound (2) was 0.0075%. Furthermore, the APHA of the purified UV absorber was determined, and the result was 169.

[0375] <Example 2>

[0376] A mixture of 50.28 parts by weight of 2,5-bis(isocyanate methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate methyl)bicyclo[2.2.1]heptane was mixed with 0.06 parts by weight of dimethyl tin dichloride as a catalyst, 0.15 parts by weight of ethyl butoxyphosphate "JP-506H" (trade name, manufactured by Jōhoku Chemical Industry Co., Ltd.) as a release agent, and 1.00 parts by weight of the ultraviolet absorber obtained in Example 1. The mixture was then stirred and mixed. Next, 25.50 parts by weight of pentaerythritol tetra(3-mercaptopropionate) and 24.22 parts by weight of 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane were added, and the mixture was stirred and mixed under reduced pressure of 10 mmHg for 30 minutes to prepare a curable composition. Next, the cured composition was injected into a pre-prepared lens molding mold (set to 0.00D, center wall thickness 1.6mm) consisting of a glass model and a resin gasket, and polymerized in an electric furnace at 20°C–120°C for 24 hours. After polymerization, the gasket and model were removed, and the mixture was heat-treated at 120°C for 2 hours to obtain the lens substrate. The center wall thickness (ct), light transmittance, and L were measured. ＊ a ＊ b ＊ The values ​​and YI values ​​are shown in Table 1.

[0377] <Comparative Example 1>

[0378] The ultraviolet absorber was changed to 1.00 parts by mass of an ultraviolet absorber containing 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole (the peak area ratio of compound (2) was 0.033%). Otherwise, the lens substrate was obtained by the same method as in Example 2. The center wall thickness (ct), light transmittance, and L were measured. ＊ a ＊ b ＊ The values ​​and YI values ​​are shown in Table 1.

[0379]

[0380] <Example 3>

[0381] To 50.60 parts by weight of 1,3-bis(isocyanate-methyl)benzene, 0.06 parts by weight of dimethyltin dichloride as a catalyst, 0.15 parts by weight of ethyl butoxyphosphate "JP-506H" (trade name, manufactured by Jōhoku Chemical Industry Co., Ltd.) as a release agent, and 0.55 parts by weight of the ultraviolet absorber obtained in Example 1 were added and stirred. Then, 0.55 parts by weight of 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester were further added and stirred. Then, 49.40 parts by weight of a mixture of 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 were added and stirred under reduced pressure (10 mmHg) for 30 minutes to prepare a curable composition. Next, this curable composition was injected into a pre-prepared lens molding mold (set to 0.00D, wall thickness 1.8 mm) formed from a glass model and a resin gasket, and polymerized in an electric furnace at 20°C–120°C for 24 hours. After polymerization, the gasket and model were removed, and the mixture was heat-treated at 120°C for 2 hours to obtain the lens substrate. The center wall thickness (ct), light transmittance, and L were measured. ＊ a ＊ b ＊ The values ​​and YI values ​​are shown in Table 2.

[0382] <Comparative Example 2>

[0383] The ultraviolet absorber was changed to an ultraviolet absorber containing 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole (the peak area ratio of compound (2) was 0.033%), 0.55 parts by mass. Otherwise, the lens substrate was obtained by the same method as in Example 3. The center wall thickness (ct), light transmittance, and L were measured. ＊ a ＊ b ＊ The values ​​and YI values ​​are shown in Table 2.

[0384]

[0385] Based on the comparison between Example 2 and Comparative Example 1, and the comparison between Example 3 and Comparative Example 2, it can be seen that by making the peak area ratio of compound (2) below a given value, a spectacle lens with a low YI value can be obtained.

Claims

1. An ultraviolet absorber comprising compound (1) of formula (1), Equation (1): ， In equation (1), R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. m is 0 or 1. n is 0 or 1, R 2 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. In the chromatogram obtained by liquid chromatography using a diode array detector to determine the ultraviolet absorber, the peak area ratio of compound (2) represented by formula (2) is less than 0.01%. ， In equation (2), R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. m is 0 or 1. n is 0 or 1, R 2 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms.

2. The ultraviolet absorber according to claim 1, wherein, In the spectrum obtained by liquid chromatography using a diode array detector to determine the ultraviolet absorber, the peak area ratio of compound (2) is greater than 0.001%.

3. The ultraviolet absorber according to claim 1, wherein, In the spectrum obtained by liquid chromatography using a diode array detector to determine the ultraviolet absorber, the peak area ratio of compound (1) is above 99%.

4. The ultraviolet absorber according to claim 1, wherein, The compound (1) is the compound (1-1) shown in formula (1-1). ， The compound (2) is the compound (2-1) shown in formula (2-1). 。 5. An eyeglass lens comprising a lens substrate comprising an ultraviolet absorber and a resin as described in any one of claims 1 to 4.

6. The spectacle lens according to claim 5, wherein, The resin is a cured product of isocyanate component and active hydrogen compound component, wherein the isocyanate component includes at least one selected from bis(isocyanate methyl)bicyclo[2.2.1]heptane, bis(isocyanate methyl)cyclohexane, bis(isocyanate methyl)benzene, toluene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate and pentamethylene diisocyanate.

7. The spectacle lens according to claim 6, wherein, The active hydrogen compound comprises at least one selected from toluene diamine, pentaerythritol tetramercaptoacetate, pentaerythritol tetramercaptopropionate, trimethylolpropane trimercaptoacetate, trimethylolpropane trimercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiadecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol.

8. The spectacle lens according to claim 7, wherein, The bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol is a mixture of 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.

9. The spectacle lens according to claim 5, wherein, The resin is an cyclic sulfur resin.

10. The spectacle lens according to claim 5, wherein, The compound (1) comprises 0.05 parts by weight and 2.00 parts by weight or less relative to 100 parts by weight of the resin.

11. The spectacle lens according to claim 5, wherein, The refractive index ne of the lens substrate is 1.52 or higher and 1.80 or lower.

12. The spectacle lens according to claim 5, wherein, The refractive index ne of the lens substrate is above 1.70 and below 1.

80.

13. The spectacle lens according to claim 5, comprising at least one layer selected from a hard coating layer, a base layer, and an anti-reflective layer.

14. A method for manufacturing ultraviolet absorber crystals, comprising a method for manufacturing ultraviolet absorber crystals containing compound (1) as shown in formula (1), Equation (1): ， In the formula, R 1 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. m is 0 or 1. n is 0 or 1, R 2 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. This method has: The process of adding an isopropanol solution to a toluene solution containing the ultraviolet absorber to obtain crystals, and The process of washing the crystals with isopropanol.

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