Patent Description:
A resin lens is lighter than a lens formed of an inorganic material such as inorganic glass, is hard to crack, and can be dyed advantageously. Therefore, it is currently the mainstream to use a resin lens as an optical component such as a spectacle lens or a camera lens.

Patent Literature <NUM> discloses an optical high refractive index plastic lens formed of a sulfur-containing polyurethane obtained by polymerizing at least one polyisocyanate compound and two or more polythiols and/or sulfur-containing polyol compounds, containing a specific dithiol compound as an essential component of polythiol, and having a refractive index of <NUM> or more and a thermal deformation temperature of <NUM> or higher. Patent Literature <NUM> describes that the plastic lens has high heat resistance without being deformed in thermal history in a post-processing step of the lens and has highly excellent dyeability.

<CIT> relates to a process for preparing optical lenses from compositions containing m-xylylene diisocyanate, which contains a preset amount of an organochloride, and <NUM>,<NUM>-bis[<NUM>-mercaptoethyl)thio]-<NUM>-mercaptopropane.

However, in a conventional plastic lens containing a polymer of a polyisocyanate component and a polythiol component, such as the plastic lens disclosed in the above Patent Literature <NUM>, a dyeing density sometimes does not rise depending on a production lot. Therefore, even in a case of further performing dyeing in the same dyeing tank in order to correct the dyeing density, it is necessary to adjust dyeing conditions for each production lot in order to accurately correct a color tone, and productivity decreases.

When a urethane resin obtained by polymerizing a polyisocyanate component and a polythiol component uses a polythiol compound having two or more sulfide bonds in a molecular structure thereof as the polythiol component for increasing a refractive index, the obtained urethane resin is hydrophobic as compared with a conventional resin, and a network structure of the resin is dense.

Therefore, a dye hardly permeates the urethane resin, and it is difficult to dye the urethane resin.

An embodiment of the present disclosure relates to a method for producing an optical component resin having excellent dyeability, an optical component resin, a spectacle lens, and spectacles.

The present inventor has found that in an optical component resin containing a polymer of a polyisocyanate component and a polythiol component containing <NUM> mol% or more of a polythiol compound having two or more sulfide bonds in a molecular structure thereof, the content of a hydrolyzable chlorine compound of the polyisocyanate component affects dyeability of the optical component resin.

An embodiment of the present disclosure relates to a method for producing an optical component resin, including a step of polymerizing a polymerizable composition containing a polyisocyanate component and a polythiol component containing <NUM> mol% or more of a polythiol compound having two or more sulfide bonds in a molecular structure thereof, in which
the content of a hydrolyzable chlorine compound contained in the polyisocyanate component is in a range of <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component.

In addition, an embodiment of the present disclosure relates to.

An embodiment of the present disclosure can provide a method for producing an optical component resin having excellent dyeability, an optical component resin, a spectacle lens, and spectacles.

A method for producing an optical component resin according to an embodiment of the present disclosure includes
a step of polymerizing a polymerizable composition containing a polyisocyanate component and a polythiol component containing <NUM> mol% or more of a polythiol compound having two or more sulfide bonds in a molecular structure thereof.

The content of a hydrolyzable chlorine compound contained in the polyisocyanate component is in a range of <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component.

With the above configuration, an optical component resin having excellent dyeability can be obtained.

The method for producing an optical component resin according to an embodiment of the present disclosure includes: for example,.

The "hydrolyzable chlorine compound" is a compound that reacts with methanol to generate hydrogen chloride.

In the method for producing an optical component resin according to an embodiment of the present disclosure, the content of a hydrolyzable chlorine compound contained in a polyisocyanate component (hereinafter also simply referred to as "content of hydrolyzable chlorine compound") is <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component from a viewpoint of obtaining an optical component resin having excellent dyeability.

The content of the hydrolyzable chlorine compound is preferably <NUM> ppm by mass or more, more preferably <NUM> ppm by mass or more, still more preferably <NUM> ppm by mass or more, further still more preferably <NUM> ppm by mass or more, and preferably <NUM> ppm by mass or less, more preferably <NUM> ppm by mass or less, still more preferably <NUM> ppm by mass or less, further still more preferably <NUM> ppm by mass or less, further still more preferably <NUM> ppm by mass or less, further still more preferably <NUM> ppm by mass or less in the polyisocyanate component from a viewpoint of obtaining a plastic lens having better dyeability.

The content of the hydrolyzable chlorine compound is preferably <NUM> ppm by mass or more and <NUM> ppm by mass or less, more preferably <NUM> ppm by mass or more and <NUM> ppm by mass or less, still more preferably <NUM> ppm by mass or more and <NUM> ppm by mass or less, further still more preferably <NUM> ppm by mass or more and <NUM> ppm by mass or less, further still more preferably <NUM> ppm by mass or more and <NUM> ppm by mass or less, further still more preferably <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component from a viewpoint of obtaining a plastic lens having better dyeability.

The content of the hydrolyzable chlorine compound contained in the polyisocyanate component is measured by a measuring method described in Examples.

As a method for adjusting the content of the hydrolyzable chlorine compound in the polyisocyanate component, for example, the content of the hydrolyzable chlorine compound can be decreased by repeated distillation of the polyisocyanate component.

In a case of mixing a polythiol component, a polyisocyanate component, and an additive, the polythiol component, the polyisocyanate component, and the additive may be mixed in any order in the mixing step. However, it is preferable to mix the polyisocyanate component and the additive (i), and then to mix the resulting mixture with the polythiol component (ii) from a viewpoint of further enhancing transparency of the optical component.

In (i), the polyisocyanate component generally has low viscosity and good solubility, and therefore the additive is easily dissolved therein. In (i), in order to shorten dissolution time, it is preferable to add and dissolve the entire amount of the additive to the total amount of the polyisocyanate component.

The polymerizable composition obtained in the mixing step contains a polythiol component, a polyisocyanate component, and an additive. Each of the components will be described below.

Examples of the polyisocyanate component include a polyisocyanate compound having an aromatic ring, an alicyclic polyisocyanate compound, and a linear or branched aliphatic polyisocyanate compound.

Examples of the polyisocyanate compound having an aromatic ring include diisocyanatobenzene, <NUM>,<NUM>-diisocyanatotoluene, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, biphenyl diisocyanate, toluidine diisocyanate, <NUM>,<NUM>'-methylene bis(phenyl isocyanate), <NUM>,<NUM>'-methylene bis(<NUM>-methyl phenyl isocyanate), bibenzyl-<NUM>,<NUM>'-diisocyanate, bis(isocyanatophenyl) ethylene, <NUM>,<NUM>-bis(isocyanatomethyl) benzene, <NUM>,<NUM>-bis(isocyanatomethyl) benzene, <NUM>,<NUM>-bis(isocyanatoethyl) benzene, bis(isocyanatopropyl) benzene, α,α,α',α'-tetramethylxylylene diisocyanate, bis(isocyanatobutyl) benzene, bis(isocyanatomethyl) naphthalene, bis(isocyanatomethylphenyl) ether, <NUM>-isocyanatophenyl-<NUM>-isocyanatophenyl sulfide, bis(<NUM>-isocyanatophenyl) sulfide, bis(<NUM>-isocyanatomethylphenyl) sulfide, bis(<NUM>-isocyanatophenyl) disulfide, bis(<NUM>-methyl-<NUM>-isocyanatophenyl) disulfide, bis(<NUM>-methyl-<NUM>-isocyanatophenyl) disulfide, bis(<NUM>-methyl-<NUM>-isocyanatophenyl) disulfide, bis(<NUM>-methyl-<NUM>-isocyanatophenyl) disulfide, bis(<NUM>-methyloxy-<NUM>-isocyanatophenyl) disulfide, and bis(<NUM>-methyloxy-<NUM>-isocyanatophenyl) disulfide.

Examples of the alicyclic polyisocyanate compound include <NUM>,<NUM>-diisocyanatocyclohexane, isophorone diisocyanate, <NUM>,<NUM>-bis(isocyanatomethyl) cyclohexane, <NUM>,<NUM>-bis(isocyanatomethyl) cyclohexane, dicyclohexylmethane-<NUM>,<NUM>'-diisocyanate, <NUM>,<NUM>-bis(isocyanatomethyl)-bicyclo[<NUM>. <NUM>]heptane, <NUM>,<NUM>-bis(isocyanatomethyl)-bicyclo[<NUM>. <NUM>]heptane, <NUM>,<NUM>-diisocyanato-<NUM>,<NUM>-dithiane, <NUM>,<NUM>-bis(isocyanatomethyl)-<NUM>,<NUM>-dithiane, <NUM>,<NUM>-diisocyanato-<NUM>,<NUM>-dithiolane, <NUM>,<NUM>-bis(isocyanatomethyl)-<NUM>,<NUM>-dithiolane, and <NUM>,<NUM>-bis(isocyanatomethyl)-<NUM>-methyl-<NUM>,<NUM>-dithiolane.

Examples of the linear or branched aliphatic polyisocyanate compound include hexamethylene diisocyanate, <NUM>,<NUM>-dimethylpentane diisocyanate, <NUM>,<NUM>,<NUM>-trimethylhexane diisocyanate, butenediisocyanate, <NUM>,<NUM>-butadiene-<NUM>,<NUM>-diisocyanate, <NUM>,<NUM>,<NUM>-trimethylhexamethylene diisocyanate, <NUM>,<NUM>,<NUM>-undecane triisocyanate, <NUM>,<NUM>,<NUM>-hexamethylene triisocyanate, <NUM>,<NUM>-diisocyanate <NUM>-isocyanatomethyloctane, bis(isocyanatoethyl) carbonate, bis(isocyanatoethyl) ether, lysine diisocyanatomethyl ester, lysine triisocyanate, bis(isocyanatomethyl) sulfide, bis(isocyanatoethyl) sulfide, bis(isocyanatopropyl) sulfide, bis(isocyanatohexyl) sulfide bis(isocyanatomethyl) sulfone, bis(isocyanatomethyl) disulfide, bis(isocyanatoethyl) disulfide, bis(isocyanatopropyl) disulfide, bis(isocyanatomethylthio) methane, bis(isocyanatoethylthio) methane, bis(isocyanatomethylthio) ethane, bis(isocyanatoethylthio) ethane, <NUM>,<NUM>-diisocyanate <NUM>-isocyanatomethyl-<NUM>-pentane, <NUM>,<NUM>,<NUM>-tris(isocyanatomethylthio) propane, <NUM>,<NUM>,<NUM>-tris(isocyanatoethylthio) propane, <NUM>,<NUM>-dithia-<NUM>,<NUM>,<NUM>,<NUM>-heptane tetraisocyanate, <NUM>,<NUM>-diisocyanatomethyl-<NUM>,<NUM>-dithia-<NUM>,<NUM>-heptane diisocyanate, <NUM>,<NUM>-diisocyanatomethylthiophene, <NUM>-isocyanatoethylthio-<NUM>,<NUM>-dithia-<NUM>,<NUM>-octanediisocyanate, <NUM>,<NUM>-diisothiocyanatoethane, and <NUM>,<NUM>-diisothiocyanatohexane.

One kind or two or more kinds of polyisocyanate compounds may be used.

The polyisocyanate component preferably contains at least one selected from the group consisting of <NUM>,<NUM>-bis(isocyanatomethyl)-bicyclo[<NUM>. <NUM>]heptane, <NUM>,<NUM>-bis(isocyanatomethyl)-bicyclo[<NUM>. <NUM>]heptane, <NUM>,<NUM>-bis(isocyanatomethyl) cyclohexane, <NUM>,<NUM>-bis(isocyanatomethyl) benzene, <NUM>,<NUM>-bis(isocyanatomethyl) benzene, dicyclohexylmethane-<NUM>,<NUM>'-diisocyanate, and isophorone diisocyanate, more preferably contains at least one selected from the group consisting of <NUM>,<NUM>-bis(isocyanatomethyl) benzene, <NUM>,<NUM>-bis(isocyanatomethyl)-bicyclo[<NUM>. <NUM>]heptane, <NUM>,<NUM>-bis(isocyanatomethyl)-bicyclo[<NUM>. <NUM>]heptane, and <NUM>,<NUM>-bis(isocyanatomethyl) cyclohexane, still more preferably contains <NUM>,<NUM>-bis(isocyanatomethyl) benzene.

The addition amount of the polyisocyanate component is preferably <NUM>% by mass or more, more preferably <NUM>% by mass or more, still more preferably <NUM>% by mass or more, and preferably <NUM>% by mass or less, more preferably <NUM>% by mass or less, still more preferably <NUM>% by mass or less with respect to the total amount of the polythiol component and the polyisocyanate component.

The addition amount of the polyisocyanate component is preferably <NUM>% by mass or more and <NUM>% by mass or less, more preferably <NUM>% by mass or more and <NUM>% by mass or less, still more preferably <NUM>% by mass or more and <NUM>% by mass or less with respect to the total amount of the polythiol component and the polyisocyanate component.

The polythiol component contains <NUM> mol% or more of a polythiol compound having two or more sulfide bonds in a molecular structure thereof.

The number of sulfide bonds in the molecular structure of the polythiol compound is <NUM> or more, preferably <NUM> or more, and preferably <NUM> or less, more preferably <NUM> or less.

Example of the polythiol compound having two or more sulfide bonds in a molecular structure thereof include <NUM>-mercaptomethyl-<NUM>,<NUM>-dimercapto-<NUM>,<NUM>-dithiaoctane, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, <NUM>,<NUM>,<NUM>,<NUM>-tetrakis(mercaptomethylthio) propane, <NUM>,<NUM>,<NUM>,<NUM>-tetrakis(mercaptoethylthio) propane, <NUM>,<NUM>,<NUM>,<NUM>-tetrakis(mercaptomethylthio) ethane, <NUM>,<NUM>,<NUM>,<NUM>-tetrakis(mercaptoethylthio) ethane, <NUM>-mercaptomethyl-<NUM>,<NUM>-dimercapto-<NUM>,<NUM>-dithiapentane, tris(mercaptomethylthio) methane, bis(mercaptomethylthio) methane, bis(<NUM>-mercaptoethylthio) methane, <NUM>,<NUM>-bis(mercaptomethylthio) ethane, <NUM>,<NUM>-bis(<NUM>-mercaptoethylthio) ethane, <NUM>,<NUM>-bis(mercaptomethylthio) propane, <NUM>,<NUM>-bis(<NUM>-mercaptoethylthio) propane, tetrakis(mercaptoethylthio) propane, bis(<NUM>-mercaptoethyl) disulfide, bis(<NUM>-mercaptoethylthio)-<NUM>-mercaptopropane, <NUM>-(<NUM>,<NUM>-bis(mercaptomethylthio) ethyl)-<NUM>,<NUM>-dithietane, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>-dithiane, and <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>-dithiane.

Among these compounds, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, and <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol are preferable.

The refractive index of the polythiol compound having two or more sulfide bonds in a molecular structure thereof is, for example, <NUM> or more or <NUM> or more from a viewpoint of remarkably obtaining the effect of the present invention, and the upper limit thereof is not particularly limited. However, the refractive index is, for example, <NUM> or less, <NUM> or less, or <NUM> or less.

The refractive index of the polythiol compound having two or more sulfide bonds in a molecular structure thereof may be, for example, <NUM> or more and <NUM> or less, <NUM> or more and <NUM> or less, or <NUM> or more and <NUM> or less from a viewpoint of remarkably obtaining the effect of the present invention.

The refractive index of the polythiol compound is measured by a method described in Examples.

The content of the polythiol compound having two or more sulfide bonds in a molecular structure thereof is <NUM> mol% or more, preferably <NUM> mol% or more, more preferably <NUM> mol% or more, still more preferably <NUM> mol % or more, further still more preferably <NUM> mol% or more, and for example, <NUM> mol% or less in the polythiol component.

The polythiol component may contain another polythiol compound different from the polythiol compound having two or more sulfide bonds in a molecular structure thereof. Examples of the other polythiol compound include a polythiol compound having one sulfide bond or no sulfide bond in a molecular structure thereof (hereinafter also referred to as "another polythiol compound").

Examples of the other polythiol compound include:.

Examples of the other linear or branched aliphatic polythiol compound include <NUM>,<NUM>-ethanedithiol, <NUM>,<NUM>-propanedithiol, <NUM>,<NUM>-propanedithiol, <NUM>,<NUM>-propanedithiol, <NUM>,<NUM>-propanedithiol, <NUM>,<NUM>-hexanedithiol, <NUM>,<NUM>,<NUM>-propanetrithiol, <NUM>,<NUM>-dimethylpropane-<NUM>,<NUM>-dithiol, <NUM>,<NUM>-dimethyloxybutane-<NUM>,<NUM>-dithiol, <NUM>,<NUM>-dimercapto-<NUM>-propanol, <NUM>,<NUM>-dimercaptopropyl methyl ether, <NUM>,<NUM>-dimercaptopropyl methyl ether, <NUM>-(<NUM>-mercaptoethylthio) propane-<NUM>,<NUM>-dithiol, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>-propanedithiol, bis(<NUM>-mercaptoethyl) ether, and bis(<NUM>-mercaptoethyl) sulfide.

In the ester compound of a polyol compound and a mercapto group-containing carboxylic acid compound, examples of the polyol compound include a compound having two or more hydroxy groups in a molecule thereof.

Examples of the polyol compound include ethylene glycol, diethylene glycol, propanediol, propanetriol, butanediol, trimethylolpropane, bis(<NUM>-hydroxyethyl) disulfide, pentaerythritol, and dipentaerythritol.

Examples of the mercapto group-containing carboxylic acid compound include thioglycolic acid, mercaptopropionic acid, a thiolactic acid compound, and thiosalicylic acid.

Examples of an ester compound of another polyol compound and a mercapto group-containing carboxylic acid compound include ethylene glycol bis(<NUM>-mercaptoacetate), ethylene glycol bis(<NUM>-mercaptopropionate), diethylene glycol bis(<NUM>-mercaptoacetate), diethylene glycol bis(<NUM>-mercaptopropionate), <NUM>,<NUM>-butanediol bis(<NUM>-mercaptoacetate), <NUM>,<NUM>-butanediol bis(<NUM>-mercaptopropionate), trimethylolpropane tris(<NUM>-mercapto acetate), trimethylolpropane tris(<NUM>-mercaptopropionate), pentaerythritol tetrakis(<NUM>-mercaptoacetate), pentaerythritol tetrakis(<NUM>-mercaptopropionate), pentaerythritol tetrakis(<NUM>-mercaptopropionate) dipentaerythritol hexakis(<NUM>-mercaptoacetate), and dipentaerythritol hexakis(<NUM>-mercaptopropionate).

Examples of the other polythiol compounds having an alicyclic structure include <NUM>,<NUM>-cyclohexanedithiol, <NUM>,<NUM>-cyclohexanedithiol, methylcyclohexanedithiol, and bis(mercaptomethyl) cyclohexane.

Examples of the other aromatic polythiol compound include <NUM>,<NUM>-dimercaptobenzene, <NUM>,<NUM>-dimercaptobenzene, <NUM>,<NUM>-bis(mercaptomethyl) benzene, <NUM>,<NUM>-bis(mercaptomethyl) benzene, <NUM>,<NUM>-bis(mercaptoethyl) benzene, <NUM>,<NUM>-bis(mercaptoethyl) benzene, <NUM>,<NUM>,<NUM>-trimercaptobenzene, <NUM>,<NUM>,<NUM>-tris(mercaptomethyl) benzene, <NUM>,<NUM>,<NUM>-tris(mercaptoethyl) benzene, <NUM>,<NUM>'-dimercaptobiphenyl, <NUM>,<NUM>'-dimercaptobibenzyl, <NUM>,<NUM>-toluenedithiol, <NUM>,<NUM>-naphthalenedithiol, <NUM>,<NUM>-naphthalenedithiol, <NUM>,<NUM>-naphthalenedithiol, <NUM>,<NUM>-dimethylbenzene-<NUM>,<NUM>-dithiol, <NUM>,<NUM>-dimethylbenzene-<NUM>,<NUM>-dithiol, <NUM>,<NUM>-anthracenedimethanethiol, <NUM>,<NUM>-di(p-methyloxyphenyl) propane-<NUM>,<NUM>-dithiol, <NUM>,<NUM>-diphenylpropane-<NUM>,<NUM>-dithiol, phenyl methane-<NUM>,<NUM>-dithiol, and <NUM>,<NUM>-di(p-mercaptophenyl) pentane.

These polythiol compounds may be used singly or in combination of two or more kinds thereof.

Among these compounds, the other polythiol compound preferably includes at least one elected from the group consisting of pentaerythritol tetrakis(<NUM>-mercaptoacetate), pentaerythritol tetrakis(<NUM>-mercaptopropionate), trimethylolpropane tris(<NUM>-mercaptoacetate), trimethylolpropane tris(<NUM>-mercaptopropionate), butanediol bis(<NUM>-mercaptoacetate), butanediol bis(<NUM>-mercaptopropionate), dipentaerythritol hexakis(<NUM>-mercaptoacetate), and dipentaerythritol hexakis(<NUM>-mercaptopropionate), more preferably includes at least one selected from the group consisting of pentaerythritol tetrakis(<NUM>-mercaptopropionate), <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>-dithiane, and pentaerythritol tetrakis(<NUM>-mercaptoacetate).

The content of the other polythiol compound is preferably <NUM> mol% or less, more preferably <NUM> mol% or less, still more preferably <NUM> mol% or less, further still more preferably <NUM> mol% or less, further still more preferably <NUM> mol% or less, for example, <NUM> mol% or more in the polythiol component.

The addition amount of the polythiol component is preferably <NUM>% by mass or more, more preferably <NUM>% by mass or more, still more preferably <NUM>% by mass or more, and preferably <NUM>% by mass or less, more preferably <NUM>% by mass or less, still more preferably <NUM>% by mass or less with respect to the total amount of the polythiol component and the polyisocyanate component.

The addition amount of the polythiol component is preferably <NUM>% by mass or more and <NUM>% by mass or less, more preferably <NUM>% by mass or more and <NUM>% by mass or less, still more preferably <NUM>% by mass or more and <NUM>% by mass or less with respect to the total amount of the polythiol component and the polyisocyanate component.

Examples of a suitable combination of the polythiol component and the polyisocyanate component include:.

Examples of the additive include a polymerization catalyst, a release agent, an ultraviolet absorber, an antioxidant, a coloring inhibitor, and a fluorescent whitening agent. One kind or two or more kinds of these additives may be used.

The additive preferably contains at least one selected from the group consisting of a polymerization catalyst, a release agent, and an ultraviolet absorber.

By mixing the above various components by a usual method, an optical component resin is obtained.

Examples of the polymerization catalyst include a tin compound and a nitrogen-containing compound.

Examples of the tin compound include an alkyl tin compound and an alkyl tin halide compound.

Examples of the alkyl tin compound include dibutyl tin diacetate and dibutyl tin dilaurate.

Examples of the alkyl tin halide compound include dibutyl tin dichloride, dimethyl tin dichloride, monomethyl tin trichloride, trimethyl tin chloride, tributyl tin chloride, tributyl tin fluoride, and dimethyl tin dibromide.

Among these compounds, dibutyl tin diacetate, dibutyl tin dilaurate, dibutyl tin dichloride, and dimethyl tin dichloride are preferable, and dimethyl tin dichloride is more preferable.

Examples of the nitrogen-containing compound include a tertiary amine, a quaternary ammonium salt, an imidazole-based compound, and a pyrazole-based compound. The tertiary amine is preferably a hindered amine.

Examples of the tertiary amine include triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, N,N-dimethylbenzylamine, N-methylmorpholine, N,N-dimethylcyclohexylamine, pentamethyldiethylenetriamine, bis(<NUM>-dimethylaminoethyl) ether, N-methylmorpholine, N,N'-dimethylpiperazine, N,N,N',N'-tetramethylethylenediamine, and <NUM>,<NUM>-diazabicyclo[<NUM>. <NUM>]octane (DABCO).

Examples of the hindered amine include <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidinol, <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-hydroxyethyl-<NUM>-piperidinol, methyl-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidyl sebacate, a mixture of methyl-<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidyl sebacate and bis(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidyl) sebacate, bis(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidyl) sebacate, bis(<NUM>,<NUM>,<NUM>,<NUM>-tetramethyl-<NUM>-(octyloxy)-<NUM>-piperidyl) sebacate, bis(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidyl) [[<NUM>,<NUM>-bis(<NUM>,<NUM>-dimethylethyl)-<NUM>-hydroxyphenyl] methyl] butyl malonate, and tetrakis(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentamethyl-<NUM>-piperidyl) butane-<NUM>,<NUM>,<NUM>,<NUM>-tetracarboxylate.

Examples of the quaternary ammonium salt include tetraethylammonium hydroxide.

Examples of the imidazole-based compound include imidazole, <NUM>,<NUM>-dimethylimidazole, benzylmethylimidazole, and <NUM>-ethyl-<NUM>-imidazole.

Examples of the pyrazole-based compound include pyrazole and <NUM>,<NUM>-dimethylpyrazole.

Among these compounds, the tertiary amine such as a hindered amine, the imidazole-based compound, and the pyrazole-based compound are preferable, and the hindered amine is more preferable.

The addition amount of the polymerization catalyst is preferably <NUM> parts by mass or more, more preferably <NUM> parts by mass or more, still more preferably <NUM> parts by mass or more, and preferably <NUM> parts by mass or less, more preferably <NUM> part by mass or less, still more preferably <NUM> parts by mass or less with respect to <NUM> parts by mass of the total amount of the polythiol component and the polyisocyanate component.

The addition amount of the polymerization catalyst is preferably <NUM> parts by mass or more and <NUM> parts by mass or less, more preferably <NUM> parts by mass or more and <NUM> part by mass or less, still more preferably <NUM> parts by mass or more and <NUM> parts by mass or less with respect to <NUM> parts by mass of the total amount of the polythiol component and the polyisocyanate component.

Examples of the ultraviolet absorber include a benzotriazole-based compound, a benzophenone-based compound, and a dibenzoylmethane-based compound. Among these compounds, the benzotriazole-based compound and the benzophenone-based compound are preferable.

Examples of the benzotriazole-based compound include <NUM>-(<NUM>-hydroxy-<NUM>-methylphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-di-tert-butylphenyl)-<NUM>-chloro-<NUM>-benzotriazole, <NUM>-(<NUM>-t-butyl-<NUM>-hydroxy-<NUM>-methylphenyl)-<NUM>-chloro-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-di-tert-amylphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>,<NUM>-di-tert-butylphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-tert-butylphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-octylphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-ethyloxyphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-propyloxyphenyl)-<NUM>-benzotriazole, <NUM>-(<NUM>-hydroxy-<NUM>-octyloxyphenyl)-<NUM>-benzotriazole, and <NUM>-(<NUM>-hydroxy-<NUM>-octyloxyphenyl)-<NUM>-chloro-<NUM>-benzotriazole. Note that <NUM>-(<NUM>-hydroxy-<NUM>-octylphenyl)-<NUM>-benzotriazole is preferably <NUM>-(<NUM>-hydroxy-<NUM>-tert-octylphenyl)-<NUM>-benzotriazole.

Note that the tert-octyl group means a <NUM>,<NUM>,<NUM>,<NUM>-tetramethylbutyl group.

Examples of the benzophenone-based compound include <NUM>,<NUM>-dihydroxybenzophenone, <NUM>-hydroxy-<NUM>-methyloxybenzophenone, <NUM>-hydroxy-<NUM>-methyloxybenzophenone-<NUM>-sulfonic acid, <NUM>-hydroxy-<NUM>-n-octoxybenzophenone, <NUM>-hydroxy-<NUM>-n-dodecyloxybenzophenone, <NUM>-hydroxy-<NUM>-benzyloxybenzophenone, and <NUM>,<NUM>'-dihydroxy-<NUM>-methyloxybenzophenone.

Examples of the dibenzoylmethane-based compound include <NUM>-tert-butyl-<NUM>'-methyloxydibenzoylmethane.

One kind or two or more kinds of these compounds may be used.

The addition amount of the ultraviolet absorber is preferably <NUM> parts by mass or more, more preferably <NUM> parts by mass or more, still more preferably <NUM> parts by mass or more, and preferably <NUM> parts by mass or less, more preferably <NUM> parts by mass or less, still more preferably <NUM> parts by mass or less with respect to <NUM> parts by mass of the total amount of the polythiol component and the polyisocyanate component from a viewpoint of more remarkably obtaining the effect of the present invention.

The addition amount of the ultraviolet absorber is preferably <NUM> parts by mass or more and <NUM> parts by mass or more or less, more preferably <NUM> parts by mass or more and <NUM> parts by mass or less, still more preferably <NUM> parts by mass or more and <NUM> parts by mass or less with respect to <NUM> parts by mass of the total amount of the polythiol component and the polyisocyanate component from a viewpoint of more remarkably obtaining the effect of the present invention.

Examples of the release agent include an acidic alkyl phosphate. The number of carbon atoms in an alkyl group of the acidic alkyl phosphate is preferably <NUM> or more, more preferably <NUM> or more, and preferably <NUM> or less, more preferably <NUM> or less.

The acidic alkyl phosphate may be either a phosphoric monoester or a phosphoric diester, but a mixture of a phosphoric monoester and a phosphoric diester is preferable.

Examples of the acidic alkyl phosphate include isopropyl acid phosphate, butyl acid phosphate, octyl acid phosphate, nonyl acid phosphate, decyl acid phosphate, isodecyl acid phosphate, tridecyl acid phosphate, stearyl acid phosphate, propylphenyl acid phosphate, butylphenyl acid phosphate, and butoxyethyl acid phosphate.

The addition amount of the release agent is preferably <NUM> parts by mass or more, more preferably <NUM> parts by mass or more, still more preferably <NUM> parts by mass or more, and preferably <NUM> part by mass or less, more preferably <NUM> parts by mass or less, still more preferably <NUM> parts by mass or less with respect to <NUM> parts by mass of the total amount of the polythiol component and the polyisocyanate component.

The addition amount of the release agent is preferably <NUM> parts by mass or more and <NUM> part by mass or less, more preferably <NUM> parts by mass or more and <NUM> parts by mass or less, still more preferably <NUM> parts by mass or more and <NUM> parts by mass or less with respect to <NUM> parts by mass of the total amount of the polythiol component and the polyisocyanate component.

The polymerizable composition obtained in the mixing step preferably be treated in a degassing step.

Degassing is performed, for example, by treating the polymerizable composition under reduced pressure.

The pressure during degassing is preferably <NUM> Pa or more, more preferably <NUM> Pa or more, still more preferably <NUM> Pa or more, and preferably <NUM> Pa or less, more preferably <NUM> Pa or less, still more preferably <NUM> Pa or less.

The pressure during degassing is preferably <NUM> Pa or more and <NUM> Pa or less, more preferably <NUM> Pa or more and <NUM> Pa or less, still more preferably <NUM> Pa or more and <NUM> Pa or less.

In the injection step, for example, the obtained polymerizable composition is injected into a molding die.

In a case where a spectacle lens is produced as an optical component, for example, a molding die including a pair of molds to form both main surfaces of the spectacle lens and a tape or a gasket having an adhesive layer on one side thereof for fixing these molds with a predetermined gap is used. The above-described mold may be formed of glass, ceramic, resin, or metal.

Prior to injection into the molding die, the polymerizable composition may be filtered. A filtration method is not particularly limited, but filtration may be performed using a filter having a pore diameter of <NUM> to <NUM>.

In the polymerization step, for example, the polymerizable composition is polymerized by heating.

Polymerization conditions can be appropriately set depending on the polymerizable composition and the shape of an optical component to be formed.

The polymerization initiation temperature and time are usually from <NUM> to <NUM>, preferably from <NUM> to <NUM>, and <NUM> to <NUM> hours. The temperature is raised from the polymerization initiation temperature, and then heating is preferably performed to perform curing formation. For example, the maximum temperature after being raised is usually from <NUM> to <NUM>.

After completion of the polymerization, the optical component may be released from a die and may be annealed.

By the above-described method, an optical component resin is obtained.

The glass transition temperature (Tg) of the optical component resin is preferably <NUM> or higher, more preferably <NUM> or higher, still more preferably <NUM> or higher, and preferably <NUM> or lower, more preferably <NUM> or lower, still more preferably <NUM> or lower, further still more preferably <NUM> or lower.

The glass transition temperature (Tg) of the optical component resin is preferably <NUM> or higher and <NUM> or lower, more preferably <NUM> or higher and <NUM> or lower, still more preferably <NUM> or higher and <NUM> or lower, further still more preferably <NUM> or higher and <NUM> or lower.

The glass transition temperature (Tg) is measured by a method described in Examples.

In the dyeing step, the obtained optical component resin is dyed after the polymerization step.

In the dyeing step, for example, the optical component resin is immersed in a dyeing solution containing a dye.

Examples of the dye used in an immersion dyeing method include an oil soluble dye and a disperse dye. Among these dyes, the disperse dye is preferable. Examples of the disperse dye include disperse dyes of an anthraquinone-based dye, an azo-based dye, and a quinoline-based dye. Among these dyes, the anthraquinone-based dye is preferable. These dyes may be used singly or in combination of two or more kinds thereof such that the optical component resin can be dyed in a desired color.

The content of the dye in the dyeing solution is preferably <NUM>/L or more and <NUM>/L or less.

The dyeing solution preferably further contains a surfactant.

Examples of the surfactant include an alkylbenzene sulfonate, an alkyl sulfosuccinate, a lauryl sulfate, a polyoxyethylene alkyl ether, a polyoxyethylene sorbitan fatty acid ester, and a polyoxyethylene stearylphenol ether sulfonate. One kind or two or more kinds of these compounds may be used.

A carrier for promoting dyeing may be added to the dyeing solution.

Examples of the carrier include an alcohol having an aromatic ring, a phenol-based compound, a naphthalene-based compound, a benzophenone-based compound, and an aromatic compound containing a halogen atom.

Examples of the alcohol having an aromatic ring include benzyl alcohol and cinnamyl alcohol.

Examples of the phenol-based compound include o-phenylphenol and p-phenylphenol.

Examples of the naphthalene-based compound include methylnaphthalene.

Examples of the aromatic compound containing a halogen atom include monochlorobenzene, o-dichlorobenzene, m-dichlorobenzene, <NUM>,<NUM>,<NUM>-trichlorobenzene, <NUM>,<NUM>,<NUM>-trichlorobenzene, <NUM>,<NUM>,<NUM>-trichlorobenzene, <NUM>,<NUM>,<NUM>-trichlorobenzene, tetrachlorobenzene, pentachlorobenzene, hexachlorobenzene, monochloronaphthalene, and dichloronaphthalene. One kind or two or more kinds of these compounds may be used.

The dyeing temperature and time may be appropriately set depending on a desired coloring density.

When it is difficult to perform dyeing by an immersion dyeing method, dyeing may be performed by a pressure dyeing method, a dye film heating method or a sublimation dyeing method.

Examples of applications of the optical component resin include a spectacle lens, a camera lens, a prism, an optical fiber, a recording medium substrate used for an optical disc or a magnetic disk, and an optical component such as an optical filter attached to a display of a computer. Among these applications, the spectacle lens is preferable.

The spectacle lens preferably includes a lens substrate formed of an optical component resin (hereinafter also referred to as "spectacle lens substrate").

The surface shape of the spectacle lens substrate is not particularly limited and may be a flat surface, a convex surface or a concave surface.

The spectacle lens substrate may be a single focus lens, a multifocal lens, a progressive addition lens, or the like. For example, as one example, in the progressive addition lens, usually, a near portion area (near portion) and a corridor area (intermediate area) are included in a lower area, and a distance portion area (distance portion) is included in an upper area.

The spectacle lens substrate may be a finish type spectacle lens substrate or a semi finish type spectacle lens substrate.

The diameter of the spectacle lens substrate is not particularly limited, but is usually about <NUM> to <NUM>.

The thickness of the geometric center of the spectacle lens substrate is not particularly limited, but is usually about <NUM> to <NUM>.

The refractive index (ne) of the spectacle lens substrate is, for example, <NUM> or more, <NUM> or more, <NUM> or more, or <NUM> or more, and the upper limit thereof is not particularly limited. However, as the refractive index is higher, a lens can have a thinner thickness.

The Abbe number (ve) of the spectacle lens substrate is, for example, <NUM> or more, <NUM> or more, <NUM> or more, or <NUM> or more, and the upper limit thereof is not particularly limited. However, as the Abbe number is higher, a lens has a smaller a chromatic aberration.

The spectacle lens preferably includes a spectacle lens substrate and a functional layer on a surface of the spectacle lens substrate.

As the functional layer, for example, at least one selected from the group consisting of a hard coat layer, a primer layer, an antireflection film, and a water repellent film may be used.

The hard coat layer is disposed for improving scratch resistance, and preferably can be formed by applying a coating solution containing a fine particulate inorganic material such as an organic silicon compound, tin oxide, silicon oxide, zirconium oxide, or titanium oxide.

The primer layer is disposed for improving impact resistance, and contains, for example, polyurethane as a main component. Here, the content of polyurethane is preferably <NUM>% by mass or more in the primer layer.

Examples of the antireflection film include a film obtained by laminating an inorganic material such as silicon oxide, titanium dioxide, zirconium oxide, or tantalum oxide.

The water repellent film can be formed using an organic silicon compound containing a fluorine atom.

The light transmittance of the spectacle lens in a wavelength range of <NUM> to <NUM> is preferably <NUM>% or more, more preferably <NUM>% or more, still more preferably <NUM>% or more, and <NUM>% or less.

The light cutting ratio of the spectacle lens in a wavelength of <NUM> is preferably <NUM>% or more, more preferably <NUM>% or more, still more preferably <NUM>% or more, further still more preferably <NUM>% or more, further still more preferably <NUM>% or more, and <NUM>% or less.

Spectacles according to an embodiment of the present invention include a spectacle lens and a frame in which the spectacle lens is mounted.

The frame includes, for example, a pair of rims, a bridge disposed between the rims, and a pair of temples each disposed at one end of each of the rims.

The frame may be a so-called rimless frame. In this case, for example, the spectacles include a pair of spectacle lenses, a bridge disposed between the spectacle lenses, and a pair of temples each disposed at one end of each of the spectacle lenses.

Hereinafter, specific Examples will be described concerning an embodiment of the present disclosure, but the present claims are not limited by the following Examples.

Methods for measuring and evaluating various physical properties were performed by the following methods.

Measurement was performed according to Plastic Polyurethane Raw Material Aromatic Isocyanate Test Method Part <NUM>: Method for Determining Hydrolyzable Chlorine specified in JIS K1603-<NUM>: <NUM>.

The refractive index of a polythiol compound was measured with helium d-line (<NUM>) at <NUM> using a refractometer "RA-<NUM>" (manufactured by Kyoto Electronics Industry Co.

nd is a refractive index measured with d-line.

The refractive index of a plastic lens was measured with F' line (<NUM>), C' line (<NUM>), and e line (<NUM>) at <NUM> using a precision refractive index meter "KPR-<NUM> type" (manufactured by Kalnew Optical Industrial Co. The Abbe number was calculated from the following formula. <MAT> ne indicates a refractive index measured with e line. nF' indicates a refractive index measured with F' line. nC' indicates a refractive index measured with C' line.

Measurement was performed using a thermomechanical analyzer "Thermo Plus EVO2" (manufactured by Rigaku Corporation) by a penetration method (sample thickness: <NUM>, pin diameter: <NUM>, weight: <NUM>, temperature rising rate: <NUM>/min). A peak temperature at which thermal expansion was changed was taken as glass transition temperature (Tg).

The light transmittance of a sample at a wavelength of <NUM> was measured using a high-speed integrating sphere spectral transmittance measuring instrument "DOT-<NUM>" (manufactured by Murakami Color Research Laboratory Co. ), and the dyeing density (%) was calculated using the following formula (<NUM>). As the dyeing density was higher, dyeing was performed at a higher density.

Each of the isocyanate components used in Examples and Comparative Examples was distilled repeatedly until the content of the hydrolyzable chlorine compound reached a predetermined content to adjust the content of the hydrolyzable chlorine compound.

<NUM> parts by mass of <NUM>,<NUM>-bis(isocyanatomethyl) benzene (content of hydrolyzable chlorine compound: <NUM> ppm by mass) as a polyisocyanate component, <NUM> parts by mass of dimethyltin dichloride as a polymerization catalyst, <NUM> parts by mass of an acidic phosphate "JP506H" (butoxyethyl acid phosphate manufactured by Johoku Chemical Co. (mixture of compounds each having one or two butoxyethyl groups as substituents)) as a release agent, and <NUM> parts by mass of <NUM>-(<NUM>-hydroxy-<NUM>-octyloxyphenyl)-<NUM>-benzotriazole "Seesorb <NUM>" (manufactured by Shipro Kasei Kaisha, Ltd. ) as an ultraviolet absorber were added. The resulting mixture was stirred until various additives were dissolved sufficiently. Thereafter, <NUM> parts by mass of a mixture of <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol, and <NUM>,<NUM>-bis(mercaptomethyl)-<NUM>,<NUM>,<NUM>-trithia-<NUM>,<NUM>-undecanedithiol (refractive index nd = <NUM>) was added as a polythiol component and mixed to obtain a polymerizable composition.

This polymerizable composition was degassed at <NUM> Pa for <NUM> minutes and then filtered with a polytetrafluoroethylene (PTFE) filter having a pore diameter of <NUM>. Subsequently, the polymerizable composition was injected into a molding die including a glass mold to form a spectacle lens substrate having a lens power D of <NUM> and a center thickness of <NUM> and a gasket. The molding die into which the polymerizable composition had been injected was gradually heated from <NUM> to <NUM> over <NUM> hours and further kept at <NUM> for two hours for polymerization.

After polymerization, the resulting product was removed from the molding die to obtain a spectacle lens substrate having a lens power D of <NUM> and a center thickness of <NUM>. The obtained spectacle lens substrate was annealed at <NUM> for two hours. The refractive index, the Abbe number, and the Tg of the obtained spectacle lens substrate were measured. Results thereof are illustrated in Table <NUM>.

One liter of pure water in a beaker was kept at <NUM> using an indirect bath while being stirred with a stirrer. Then, to the pure water being kept warm in the beaker, <NUM> of cinnamyl alcohol as a dyeing carrier, <NUM> of <NUM>-ethylhexyl sodium sulfate (<NUM>% by mass aqueous solution) "Sintrex EH-R" (manufactured by NOF corporation) as a surfactant, and <NUM> of polyoxyethylene stearylphenol ether sulfonate (<NUM>% by mass aqueous solution) "Neonol <NUM>" (manufactured by Seiken Kako Co. ) were added. Then, <NUM> of a blue dye "FSP Blue AUL-S" (anthraquinone-based disperse dye manufactured by Futaba Sangyo Co. ) as a disperse dye, <NUM> of a red dye "FSP Red E-A" (anthraquinone-based disperse dye manufactured by Futaba Sangyo Co. ), <NUM> of a yellow dye "FSP Yellow FL" (manufactured by Futaba Sangyo Co. ), and <NUM> of a brown dye "FSP Red S-N" (manufactured by Futaba Sangyo Co. ) were added. Then, the aqueous solution in the beaker was stirred for <NUM> minutes or more using a stirrer, and each additive was uniformly dispersed and dissolved to prepare a dyeing solution. Incidentally, during preparation of the dyeing solution, the dyeing solution was kept warm such that the liquid temperature thereof was kept constant at <NUM> all the time.

A spectacle lens substrate was immersed in the dyeing solution at <NUM> for <NUM> seconds to perform dyeing. Then, the dyeing density was measured. Results thereof are illustrated in Table <NUM>.

A spectacle lens substrate was obtained in a similar manner to Example <NUM> except that a polyisocyanate component having the content of a hydrolyzable chlorine compound illustrated in Table <NUM> was used. The refractive index, the Abbe number, the Tg, and the dyeing density of the obtained spectacle lens substrate were measured. Results thereof are illustrated in Table <NUM>.

Comparison between Examples <NUM> to <NUM> and Comparative Example <NUM> indicates that excellent dyeability is obtained when the content of a hydrolyzable chlorine compound contained in the polyisocyanate component is in a range of <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component.

Finally, the embodiment of the present disclosure will be summarized.

An embodiment of the present disclosure is a method for producing an optical component resin, including a step of polymerizing a polymerizable composition containing a polyisocyanate component and a polythiol component containing <NUM> mol% or more of a polythiol compound having two or more sulfide bonds in a molecular structure thereof, in which
the content of a hydrolyzable chlorine compound contained in the polyisocyanate component is in a range of <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component.

An Example described above can provide an optical component resin having excellent dyeability.

Claim 1:
A method for producing an optical component resin, comprising
a step of polymerizing a polymerizable composition containing a polyisocyanate component and a polythiol component containing <NUM> mol% or more of a polythiol compound having two or more sulfide bonds in a molecular structure thereof, wherein
a hydrolyzable chlorine compound contained in the polyisocyanate component has a content in a range of <NUM> ppm by mass or more and <NUM> ppm by mass or less in the polyisocyanate component,
a hydrolyzable chlorine compound is a compound that reacts with methanol to generate hydrogen chloride, and
the content of the hydrolyzable chlorine compound contained in the polyisocyanate component is measured according to Plastic Polyurethane Raw Material Aromatic Isocyanate Test Method Part <NUM>: Method for Determining Hydrolyzable Chlorine specified in JIS K1603-<NUM>: <NUM>.