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WO2025204747A1 - Lentille en plastique et lunettes - Google Patents

Lentille en plastique et lunettes

Info

Publication number
WO2025204747A1
WO2025204747A1 PCT/JP2025/008433 JP2025008433W WO2025204747A1 WO 2025204747 A1 WO2025204747 A1 WO 2025204747A1 JP 2025008433 W JP2025008433 W JP 2025008433W WO 2025204747 A1 WO2025204747 A1 WO 2025204747A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
layer
photochromic
composition
meth
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/008433
Other languages
English (en)
Japanese (ja)
Inventor
敬介 高田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoya Lens Thailand Ltd
Original Assignee
Hoya Lens Thailand Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoya Lens Thailand Ltd filed Critical Hoya Lens Thailand Ltd
Publication of WO2025204747A1 publication Critical patent/WO2025204747A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—Photochromic filters
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses

Definitions

  • This disclosure relates to plastic lenses and eyeglasses, and in particular to photochromic plastic lenses that are less likely to develop arc-shaped color unevenness around the edges of the plastic lenses, and eyeglasses equipped with such plastic lenses.
  • Glasses equipped with plastic lenses that exhibit photochromic properties i.e., develop color under light in a specific wavelength range (e.g., outdoors) and fade under light outside that wavelength range (e.g., indoors), are highly convenient in that they eliminate the need to change glasses when moving between indoors and outdoors.
  • the photochromic plastic lens is required to have little uneven coloring in order to maintain a good field of vision even after coloring.
  • a method for imparting photochromic properties to a plastic lens includes applying a layer of a composition (polymerizable composition for forming a photochromic layer) containing a photochromic compound and a polymerizable compound having photochromic properties onto the surface of a lens substrate, and curing the applied polymerizable composition for forming a photochromic layer by irradiating it with light to form a cured coating layer (photochromic layer) having photochromic properties.
  • Patent Document 1 discloses a polymerizable composition for forming a photochromic layer, which has an absorbance of 0.100 or more at 420 nm and an absorbance of 0.015 or more at 430 nm, and in which, when measuring the color density, the value of the color density measured in a state where light with a wavelength of 380 nm or less is blocked by the value of the color density measured in a state where light with a wavelength of 380 nm or less is not blocked is 0.60 or more.
  • Patent Document 1 does not specifically consider the suppression of color unevenness in photochromic plastic lenses, and plastic lenses equipped with a photochromic layer formed by curing the polymerizable composition for forming a photochromic layer disclosed in Patent Document 1 are sometimes found to have arc-shaped color unevenness around their periphery, and it cannot necessarily be said that color unevenness is sufficiently suppressed.
  • One aspect of the present disclosure aims to provide a photochromic plastic lens that is less likely to develop arc-shaped color unevenness around the periphery of the plastic lens, and eyeglasses equipped with the plastic lens.
  • Embodiments of the present disclosure relate to the following [1] to [8].
  • the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 780 nm
  • the photochromic layer-forming polymerizable composition comprising a plurality of photochromic compounds,
  • the absorbance at 420 nm is 0.100 or more
  • the absorbance at 430 nm is 0.015 or more
  • the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 380 nm, the coating material has a transmittance of 15% or less for light with a wavelength of 365 nm;
  • the photochromic layer-forming polymerizable composition is (meth)acrylate, The plastic lens according to [4] above, comprising a photochromic compound.
  • on the surface of X is a concept that includes not only “on the surface of X (contact state)” but also “above the surface of X (non-contact state).”
  • (meth)acrylate encompasses acrylate and methacrylate.
  • An “acrylate” is a compound having one or more acryloyl groups in one molecule.
  • a “methacrylate” is a compound having one or more methacryloyl groups in one molecule.
  • the functionality of a (meth)acrylate is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule.
  • examples of the substituent include an alkyl group (e.g., a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (e.g., an alkoxy group having 1 to 6 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, an aryl group, a polyether group, etc.
  • an alkyl group e.g., a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms
  • a hydroxyl group e.g., an alkoxy group having 1 to 6 carbon atoms
  • a halogen atom e.g., a fluorine
  • the "number of carbon atoms” refers to the number of carbon atoms in the portion excluding the substituent.
  • the term "straight-chain alkyl group or branched alkyl group” does not include a cycloalkyl group.
  • the straight-chain alkyl group or branched alkyl group may be unsubstituted or may have a substituent. It is acceptable for the straight-chain alkyl group or branched alkyl group to have a cycloalkyl group (e.g., a cyclohexyl group) as a substituent.
  • the straight-chain alkyl group or branched alkyl group does not have a cycloalkyl group as a substituent.
  • "at least a portion of a specific wavelength range” may refer to a part or the entirety of the specific wavelength range.
  • the specific wavelength range is 280 to 380 nm
  • "at least a portion of the specific wavelength range” may be 365 nm, 300 to 360 nm, or 280 to 380 nm.
  • the "viscosity” is a value measured by a vibration viscometer in an atmospheric atmosphere at a temperature of 25°C.
  • total amount refers to the total amount of all components excluding the solvent, when the solvent is included.
  • central portion of the lens substrate refers to the portion of the lens substrate that is within a radius of 5 mm from the center of the lens substrate.
  • peripheral portion of the lens substrate refers to a portion of the lens substrate having a radius of 15 mm or more from the center thereof.
  • mid-peripheral portion of the lens substrate refers to a portion of the lens substrate that is more than 5 mm and less than 15 mm in radius from the center of the lens substrate.
  • plastic lens used in this disclosure and this specification may be a finished lens or a semi-finished lens. Note that a semi-finished lens is processed by polishing or grinding into a lens for actual use. In this disclosure and this specification, the term “finished lens” refers to a semi-finished lens that has been processed by polishing or grinding into a lens for actual use, or a lens molded into a lens for actual use. In this disclosure and this specification, the “thickness of the lens substrate” refers to the value measured by connecting terminals to the convex and concave surfaces of the lens substrate using a high-performance ABS Digimatic Indicator (ID-FNX series, manufactured by Mitutoyo Corporation).
  • ID-FNX series high-performance ABS Digimatic Indicator
  • the "intensity of light irradiation” in this disclosure and this specification is a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm).
  • the "exposure amount of light irradiation” in this disclosure and this specification is a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm), or a value calculated from the light irradiation intensity (mW/cm 2 ) x irradiation time (seconds).
  • transmittance refers to a value measured using a spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation) by transmitting light separated by wavelength through a lens substrate or a glass substrate on which a coating material is disposed (dyed).
  • maximum transmittance refers to the transmittance value of the wavelength at which the transmittance is maximum within a specific wavelength range.
  • room temperature refers to the ambient temperature without temperature control such as heating or cooling, and is generally about 20°C, but is not limited to the above range as this may vary depending on the weather and season.
  • the plastic lens (1) includes a lens substrate, a photochromic layer formed on one surface of the lens substrate by curing a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range, and a coating material that coats the edge surface of the lens substrate and suppresses the incidence of light in at least a portion of the specific wavelength range onto the lens substrate.
  • a coating material There are no particular restrictions on the coating material, as long as the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 780 nm and the coating material has a maximum transmittance of 35% or less for light in a wavelength range of 280 to 450 nm.
  • lens substrate The lens substrate (hereinafter sometimes simply referred to as “lens substrate (1)") included in the plastic lens (1) will be described in more detail below.
  • the material for the lens substrate (1) is not particularly limited and includes, for example, (meth)acrylic resin; styrene resin; polycarbonate resin; allyl resin; allyl carbonate resin such as diethylene glycol bisallyl carbonate resin (CR-39); vinyl resin; polyester resin; polyether resin; urethane resin obtained by reacting an isocyanate compound with a hydroxy compound such as diethylene glycol; thiourethane resin obtained by reacting an isocyanate compound with a polythiol compound; a cured product (commonly referred to as a transparent resin) obtained by curing a curable composition containing a (thio)epoxy compound having one or more disulfide bonds in the molecule; and oxides such as boric oxide, aluminum oxide, and silicon oxide. These may be used alone or in combination of two or more.
  • lens substrate (1) There are no particular limitations on the type of lens substrate (1), and examples include lens substrate (1) used for eyeglasses, lens substrate (1) used for goggles, etc.
  • the color of the lens substrate (1) there are no particular restrictions on the color of the lens substrate (1), and it may be colorless (an undyed lens) or dyed.
  • the refractive index of the lens substrate (1) is not particularly limited, and may be, for example, 1.50 to 1.75. Note that in this disclosure and specification, the refractive index refers to the refractive index for light with a wavelength of 546.07 nm, which is the mercury e-line.
  • focal point of the lens substrate (1) there are no particular limitations on the focal point of the lens substrate (1), and examples include single-focus, multi-focus, and progressive-addition lenses.
  • the surface of the lens substrate (1) is not particularly limited, and examples thereof include a convex surface, a concave surface, a flat surface, etc.
  • the object-side surface is a convex surface and the eyeball-side surface is a concave surface, but the present disclosure is not limited thereto.
  • the one surface of the lens substrate (1) and examples thereof include a convex surface, a concave surface, and a flat surface.
  • the other surface of the lens substrate (1) is not particularly limited, and may be, for example, a convex surface, a concave surface, or a flat surface.
  • the thickness of the central portion of the lens substrate (1) is not particularly limited, but from the viewpoint of optical design, it is preferably less than 9.1 mm, more preferably 0.8 to 2.4 mm, and particularly preferably 0.8 mm or more and less than 2.2 mm.
  • the thickness of the peripheral portion of the lens substrate (1) is not particularly limited, but from the viewpoint of optical design, it is preferably thicker than the central portion, more preferably 0.8 to 16.5 mm, and particularly preferably 1.6 to 13.0 mm.
  • the maximum transmittance of the lens substrate (1) for light in the wavelength range of 280 to 780 nm is preferably 10% or more, more preferably 30% or more, even more preferably 50% or more, and particularly preferably 70% or more.
  • the primer layer (1) is a cured coating layer obtained by curing a polymerizable composition for forming a primer layer (hereinafter, sometimes simply referred to as a "primer layer composition").
  • a primer layer composition used to form the primer layer (1) can be a primer layer composition that can be prepared from a known adhesive (hereinafter, sometimes simply referred to as “primer layer composition (1)").
  • the pressure-sensitive adhesive is not particularly limited, and examples thereof include moisture-curing polyurethane-based pressure-sensitive adhesives, polyisocyanate-polyester-based two-component pressure-sensitive adhesives, polyisocyanate-polyether-based two-component pressure-sensitive adhesives, polyisocyanate-polyacrylic-based two-component pressure-sensitive adhesives, polyisocyanate-polyurethane elastomer-based two-component pressure-sensitive adhesives, epoxy-based pressure-sensitive adhesives, epoxy-polyurethane-based two-component pressure-sensitive adhesives, polyester-based pressure-sensitive adhesives, polyurethane urea-based one-component pressure-sensitive adhesives, water-dispersible polyurethane-based pressure-sensitive adhesives, etc. These may be used alone or in combination of two or more.
  • the primer layer composition (1) may or may not contain a solvent.
  • One form of the photochromic layer (1) can be obtained by curing a photochromic layer-forming polymerizable composition (hereinafter, sometimes simply referred to as a "photochromic layer composition") that is sensitive to light in a wavelength range of 280 to 780 nm and exhibits photochromic properties.
  • the position of the photochromic layer (1) is not particularly limited, but it is preferably on the primer layer (1) described above from the viewpoint of adhesion to the lens substrate.
  • the wavelength range to which the photochromic layer (1) is sensitive depends on the type of polymerization initiator, but is not particularly limited as long as it is between 280 and 780 nm, and is preferably between 280 and 600 nm, more preferably between 280 and 500 nm, and particularly preferably between 280 and 430 nm. If the wavelength is above the lower limit of the above range, destruction of the photochromic compound by ultraviolet rays is more easily suppressed, and if the wavelength is below the upper limit of the above range, it becomes more sensitive to visible light.
  • the thickness of the photochromic layer (1) is preferably 5 to 80 ⁇ m, more preferably 10 to 70 ⁇ m, and particularly preferably 15 to 60 ⁇ m.
  • a thickness equal to or greater than the lower limit of the above range makes it easier to ensure a good appearance, while a thickness equal to or less than the upper limit of the above range makes it easier to develop a high-density color.
  • composition for photochromic layer that is sensitive to light in the wavelength range of 280 to 780 nm can be a composition for photochromic layer that contains a plurality of photochromic compounds, has an absorbance at 420 nm of 0.100 or more, an absorbance at 430 nm of 0.015 or more, and, when measuring the color density, the value of the color density measured in a state where light with a wavelength of 380 nm or less is blocked by the value of the color density measured in a state where light with a wavelength of 380 nm or less is not blocked is 0.60 or more (hereinafter, this may be simply referred to as "composition for photochromic layer (1)").
  • the photochromic layer composition (1) may further contain a polymerizable compound, a polymerization initiator, a dye, etc., as necessary.
  • the various components contained in the composition for photochromic layer (1) will be described in more detail below.
  • the multiple photochromic compounds contained in the composition for photochromic layer (1) are not particularly limited, as long as the composition for photochromic layer (1) has an absorbance at 420 nm of 0.100 or more and an absorbance at 430 nm of 0.015 or more, and when measuring the color density, the value of the color density measured in a state where light with a wavelength of 380 nm or less is blocked by the value of the color density measured in a state where light with a wavelength of 380 nm or less is not blocked is 0.60 or more.
  • All of the photochromic compounds contained in the composition for photochromic layer (1) may be photochromic compounds having an absorbance at 420 nm of 0.100 or more, an absorbance at 430 nm of 0.015 or more, and a visible light sensitivity of 0.60 or more (hereinafter, these may be simply referred to as "first photochromic compounds").
  • the photochromic compounds contained in the photochromic layer composition (1) may include a first photochromic compound and a photochromic compound that does not satisfy at least one of the following conditions: an absorbance at 420 nm of 0.100 or more, an absorbance at 430 nm of 0.015 or more, and a visible light sensitivity of 0.60 or more.
  • the photochromic compounds contained in the photochromic layer composition (1) may include a first photochromic compound and a compound that has an absorbance at 420 nm of less than 0.100, an absorbance at 430 nm of less than 0.015, and a visible light sensitivity of less than 0.60 (hereinafter, sometimes simply referred to as a "second photochromic compound").
  • a compound that includes a second photochromic compound with low visible light responsiveness and high transmittance and a first photochromic compound with high visible light responsiveness and excellent antiglare properties is preferred.
  • the first photochromic compound is not particularly limited, and examples thereof include fulgide compounds, chromene compounds, spirooxazine compounds, etc. These may be used alone or in combination of two or more.
  • a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton represented by the following formula (11) is preferably used, particularly from the viewpoint of absorption characteristics in a colorless state (state before color development):
  • R1 and R2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a heterocyclic group containing a nitrogen ring atom and bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, or an aryl group, provided that both R1 and R2 are not hydrogen atoms.
  • R3 is a hydroxyl group, a nitro group, an alkyl group, a cycloalkyl group, an alkoxy group, an amino group, a heterocyclic group that contains a nitrogen ring atom and is bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, or an aryl group.
  • the alkyl group is not particularly limited, but is preferably an alkyl group having 1 to 6 carbon atoms.
  • alkyl groups having 1 to 6 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, and hexyl.
  • the haloalkyl group is not particularly limited, but is preferably an alkyl group having 1 to 6 carbon atoms substituted with a fluorine atom, a chlorine atom, or a bromine atom.
  • the alkyl group having 1 to 6 carbon atoms substituted with a fluorine atom, a chlorine atom, or a bromine atom is not particularly limited, and examples include a trifluoromethyl group, a tetrafluoroethyl group, a chloromethyl group, a 2-chloroethyl group, and a bromomethyl group.
  • the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 8 carbon atoms. There are no particular limitations on the cycloalkyl group having 3 to 8 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.
  • the alkoxy group is not particularly limited, but is preferably an alkoxy group having 1 to 6 carbon atoms.
  • alkoxy groups having 1 to 6 carbon atoms include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, and tert-butoxy.
  • the amino group is not limited to an amino group (-NH 2 ), and one or two hydrogen atoms may be substituted.
  • the substituent on the amino group is not particularly limited, and examples thereof include an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 14 carbon atoms, and a heteroaryl group having 4 to 14 carbon atoms.
  • amino group, methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, and diphenylamino group are preferred.
  • the heterocyclic group containing the above-mentioned ring-membered nitrogen atom and bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom is not particularly limited, but suitable examples include aliphatic heterocyclic groups such as morpholino, piperidino, pyrrolidinyl, piperazino, and N-methylpiperazino; and aromatic heterocyclic groups such as indolinyl.
  • the above-mentioned heterocyclic group may have a substituent.
  • the substituent is not particularly limited, but suitable examples include alkyl groups.
  • the substituted heterocyclic group is not particularly limited, but suitable examples include 2,6-dimethylmorpholino, 2,6-dimethylpiperidino, and 2,2,6,6-tetramethylpiperidino.
  • alkylcarbonyl group is not particularly limited, but preferred examples include alkylcarbonyl groups having 2 to 7 carbon atoms. There are also no particular limitations on alkylcarbonyl groups having 2 to 7 carbon atoms, and examples include an acetyl group and an ethylcarbonyl group.
  • the alkoxycarbonyl group is not particularly limited, but preferred examples include alkoxycarbonyl groups having 2 to 7 carbon atoms. There are also no particular limitations on the alkoxycarbonyl group having 2 to 7 carbon atoms, and examples include methoxycarbonyl and ethoxycarbonyl groups.
  • halogen atoms are not particularly limited, and examples include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
  • the aralkyl group is not particularly limited, but preferred examples include aralkyl groups having 7 to 11 carbon atoms.
  • Aralkyl groups having 7 to 11 carbon atoms are not particularly limited, and examples include benzyl, phenylethyl, phenylpropyl, phenylbutyl, and naphthylmethyl groups.
  • the aralkoxy group is not particularly limited, but preferred examples include aralkoxy groups having 7 to 11 carbon atoms. There are also no particular limitations on aralkoxy groups having 7 to 11 carbon atoms, and examples include benzyloxy and naphthylmethoxy groups.
  • the above-mentioned aralkyl group and aralkoxy group are not particularly limited, but preferably 1 to 7 hydrogen atoms on the benzene or naphthalene ring are substituted with any of the above-mentioned hydroxyl groups, alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, amino groups, cyano groups, nitro groups, or halogen atoms, and more preferably 1 to 4 hydrogen atoms on the benzene or naphthalene ring are substituted with any of the above-mentioned hydroxyl groups, alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, amino groups, cyano groups, nitro groups, or halogen atoms.
  • the aryloxy group is not particularly limited, but preferred examples include aryloxy groups having 6 to 12 carbon atoms. There are also no particular limitations on the aryloxy group having 6 to 12 carbon atoms, and examples include phenyloxy and naphthyloxy groups.
  • the aryl group is not particularly limited, but preferred examples include aryl groups having 6 to 14 carbon atoms. There are also no particular limitations on the aryl group having 6 to 14 carbon atoms, and examples include phenyl, 1-naphthyl, and 2-naphthyl groups.
  • the above-mentioned aryloxy group is not particularly limited, but it is preferable that 1 to 7 hydrogen atoms on the benzene or naphthalene ring be substituted with any of the above-mentioned alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, amino groups, or halogen atoms, and it is even more preferable that 1 to 4 hydrogen atoms on the benzene or naphthalene ring be substituted with any of the above-mentioned alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, amino groups, or halogen atoms.
  • At least two of the groups R 1 , R 2 , and R 3 are preferably the alkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group containing a ring-membered nitrogen atom and bonded to the aromatic hydrocarbon ring or aromatic heterocycle via the nitrogen atom, aralkyl group, aralkoxy group, aryloxy group, or aryl group.
  • the remaining group may be any of the groups exemplified above.
  • R 1 is an alkoxy group, aryloxy group, or aryl group
  • R 2 is an alkoxy group, amino group, heterocyclic group containing a ring-membered nitrogen atom and bonded to the aromatic hydrocarbon ring or aromatic heterocycle via the nitrogen atom, aryloxy group, or aryl group
  • R 3 is an alkoxy group, amino group, aryloxy group, or aryl group.
  • R1 is at least one group selected from the group consisting of an alkoxy group, an aryloxy group, and an aryl group
  • R2 is an alkoxy group, an amino group, an aryloxy group, or an aryl group
  • R3 is an alkoxy group.
  • R4 and R5 are each independently an aryl group, a heteroaryl group, or an alkyl group.
  • at least one of R4 and R5 is an aryl group or a heteroaryl group
  • both of R4 and R5 are an aryl group or a heteroaryl group
  • at least one of R4 and R5 is any one of the groups shown in the following (i) to (iii)
  • the positions and the total number of substituents substituted on the aryl group or heteroaryl group in the above (i) to (iii) are not particularly limited. However, from the viewpoint of exhibiting excellent photochromic properties, when the aryl group is a phenyl group, the substitution position is preferably the 3- or 4-position, and the number of substituents in this case is preferably 1.
  • the aryl group in (i) to (iii) above is not particularly limited, and examples include a 4-methylphenyl group, a 4-methoxyphenyl group, a 3,4-dimethoxyphenyl group, a 4-n-propoxyphenyl group, a 4-(N,N-dimethylamino)phenyl group, a 4-(N,N-diethylamino)phenyl group, a 4-(N,N-diphenylamino)phenyl group, a 4-morpholinophenyl group, a 4-piperidinophenyl group, a 3-(N,N-dimethylamino)phenyl group, and a 4-(2,6-dimethylpiperidino)phenyl group.
  • the total number of substituents on the heteroaryl groups in (i) to (iii) above is not particularly limited, but is preferably 1.
  • heteroaryl groups include a 4-methoxythienyl group, a 4-(N,N-dimethylamino)thienyl group, a 4-methylfuryl group, a 4-(N,N-diethylamino)furyl group, a 4-(N,N-diphenylamino)thienyl group, a 4-morpholinopyrrolinyl group, a 6-piperidinobenzothienyl group, and a 6-(N,N-dimethylamino)benzofuranyl group.
  • the chromene compound (photochromic compound) becomes a double-peak compound having two absorption peaks.
  • This double-peak compound is suitable for use because it facilitates color adjustment and there is little change in color over time due to deterioration. In particular, it is suitable for use when mixing with other photochromic compounds to adjust the color.
  • R6 and R7 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an alkoxyalkyl group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, or an aryl group.
  • a hydroxyl group, an alkyl group such as a methyl group, and an alkoxy group such as a methoxy group are preferred.
  • alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group and aryl group represented by R6 and R7 include the same groups as those described above for R1 , R2 and R3 .
  • the alkoxyalkyl group represented by R6 and R7 is not particularly limited, but suitable examples include alkoxyalkyl groups having 2 to 7 carbon atoms.
  • the alkoxyalkyl group having 2 to 7 carbon atoms is not particularly limited, and examples include a methoxymethyl group, a methoxyethyl group, a methoxy n-propyl group, a methoxy n-butyl group, an ethoxyethyl group, and an n-propoxypropyl group.
  • R6 and R7 may, together with the carbon atom at position 13 to which they are bonded, form an aliphatic ring having 3 to 20 ring carbon atoms, a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the aliphatic ring, a heterocycle having 3 to 20 ring atoms, or a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the heterocycle.
  • the aliphatic ring is not particularly limited, and examples include a cyclopentane ring, a cyclohexane ring, a cyclooctane ring, a cycloheptane ring, a norbornane ring, a bicyclononane ring, and an adamantane ring.
  • the fused polycyclic ring in which an aromatic ring or aromatic heterocycle is fused to the above-mentioned aliphatic ring is not particularly limited, and examples include a phenanthrene ring.
  • the fused polycyclic ring in which an aromatic ring or aromatic heterocycle is fused to the heterocycle is not particularly limited, and examples include a phenylfuran ring, a biphenylthiophene ring, etc.
  • R6 and R7 form a ring together with the carbon atom at the 13th position to which R6 and R7 are bonded, more preferably form an aliphatic ring or a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed with an aliphatic ring, and it is particularly preferable that they form an aliphatic ring from the viewpoint of reducing initial coloring due to thermochromism.
  • the aliphatic ring formed by R6 and R7 is not particularly limited, and suitable examples thereof include an unsubstituted aliphatic hydrocarbon ring; an aliphatic hydrocarbon ring having at least one substituent selected from the group consisting of an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, an aralkyl group, an aryl group, and a halogen atom; etc.
  • alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, aralkyl group, aryl group, and halogen atom examples include the same groups as those described for R1 , R2 , and R3 .
  • the aliphatic hydrocarbon ring formed by R6 and R7 is not particularly limited, and examples thereof include monocyclic rings such as cyclohexane, cyclooctane, and cycloheptane; bicyclic rings such as norbornane, bicyclo[3,2,1]octane, bicyclo[4,2,0]octane, bicyclo[3,3,0]octane, bicyclo[3,3,1]nonane, bicyclo[4,3,0]nonane, and bicyclo[6,3,0]undecane; tricyclic rings such as adamantane; and rings substituted with at least one lower alkyl group having 4 or less carbon atoms, such as a methyl group.
  • monocyclic or bicyclic rings are preferred from the viewpoint of minimizing initial coloration due to thermochromism while maintaining high double peak properties and fast fading speed.
  • Specific examples of the monocyclic or bicyclic ring formed by R6 and R7 include those represented by the following formula (12): In the following formula (12), the carbon atom marked with 13 is the carbon atom at the 13th position.
  • cyclooctane ring 3,3,5,5-tetramethylcyclohexane ring, 4,4-diethylcyclohexane ring, 4,4-dimethylcyclohexane ring, and bicyclo[4,3,0]nonane ring are preferred.
  • the second photochromic compound is not particularly limited, but from the viewpoint of photochromic properties such as color density, initial coloring, durability, and color fading rate, it is preferably a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton, excluding the chromene compound represented by formula (1), and from the viewpoint of color density and color fading rate, it is more preferably a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton and having a molecular weight of 540 or more, and particularly preferably a chromene compound represented by formula (21) below.
  • R 30 is a hydrogen atom.
  • R 10 and R 20 each independently represent a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a heterocyclic group that contains a nitrogen ring atom and is bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, an arylthio group, or an aryl group.
  • the chromene compound (second photochromic compound) represented by the formula (21) is a compound in which the substituent ( R30 ) at the 11th position is a hydrogen atom, and is therefore different from the chromene compound represented by the formula (1).
  • R10 and R20 are as described above, and the groups exemplified above include the same groups as those described for R1 , R2 , and R3 , and preferred groups are also the same.
  • the arylthio group represented by R 10 and R 20 is not particularly limited, but suitable examples include arylthio groups having 6 to 12 carbon atoms.
  • the arylthio group having 6 to 12 carbon atoms is not particularly limited, and examples include a phenylthio group and a naphthylthio group.
  • the arylthio group is a phenylthio group, it preferably has a substituent at at least one ortho position, and the substituent is preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or an aryl group having 6 to 14 carbon atoms.
  • R10 and R20 are not particularly limited, from the viewpoint of achieving a high level of both transparency and antiglare properties, they are preferably each independently a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an aryloxy group, an arylthio group, or an aryl group.
  • groups other than hydrogen atoms are as described above, and the groups exemplified above include the same groups as those described for R1 , R2 , and R3 , and preferred groups are also the same.
  • R 40 and R 50 are each independently the same groups as R 4 and R 5 in formula (1), and the preferred groups are also the same.
  • R 60 and R 70 are the same groups as R 6 and R 7 in formula (1). From the viewpoint of imparting excellent antiglare properties and transparency to the photochromic layer, it is preferable that R 60 and R 70 , together with the carbon atom at position 13 to which they are bonded, form an aliphatic ring having 3 to 20 ring carbon atoms, a condensed polycyclic ring in which an aromatic ring or an aromatic heterocycle is condensed to the aliphatic ring, a heterocyclic ring having 3 to 20 ring atoms, or a condensed polycyclic ring in which an aromatic ring or an aromatic heterocycle is condensed to the heterocycle.
  • preferred groups include the same groups as those described for R 6 and R 7.
  • R 60 and R 70 are preferably monocyclic or bicyclic rings exemplified as preferred groups for R 6 and R 7 .
  • Examples of the second photochromic compound include compounds of the following formulas (22) and (23).
  • the multiple photochromic compounds contained in the photochromic layer composition (1) are not particularly limited, but from the standpoint of excellent anti-glare properties and transmittance, it is preferable that the composition contain a second photochromic compound that has low visible light responsiveness and high transmittance, and a first photochromic compound that has high visible light responsiveness and excellent anti-glare properties.
  • the first photochromic compound is not particularly limited, but preferably has an absorbance at 420 nm of 0.150 to 0.800, an absorbance at 430 nm of 0.020 to 0.500, and a visible light sensitivity of 0.61 to 1.0; more preferably, an absorbance at 420 nm of 0.200 to 0.700, an absorbance at 430 nm of 0.050 to 0.300, and a visible light sensitivity of 0.65 to 0.95; and particularly preferably, an absorbance at 420 nm of 0.300 to 0.600, an absorbance at 430 nm of 0.070 to 0.200, and a visible light sensitivity of 0.70 to 0.90.
  • the second photochromic compound is not particularly limited, but preferably has an absorbance at 420 nm of 0.001 or more and less than 0.120, an absorbance at 430 nm of 0.000 or more and less than 0.015, and a visible light sensitivity of 0.10 or more and less than 0.60; more preferably, an absorbance at 420 nm of 0.005 to 0.100, an absorbance at 430 nm of 0.001 to 0.013, and a visible light sensitivity of 0.20 to 0.55; and particularly preferably, an absorbance at 420 nm of 0.02 to 0.095, an absorbance at 430 nm of 0.005 to 0.012, and a visible light sensitivity of 0.30 to 0.55.
  • the amount of the second photochromic compound blended there are no particular restrictions on the amount of the second photochromic compound blended, so long as the photochromic layer composition (1) has an absorbance of 0.0100 or more at 420 nm, an absorbance of 0.015 or more at 430 nm, and a visible light sensitivity of 0.60 or more.
  • the amount is preferably 1 to 100 parts by mass, and more preferably 10 to 50 parts by mass, per 100 parts by mass of the first photochromic compound.
  • the content of the above-mentioned multiple photochromic compounds is not particularly limited, but from the viewpoint of ensuring that the photochromic layer composition (1) has an absorbance of 0.0100 or more at 420 nm, an absorbance of 0.015 or more at 430 nm, and a visible light sensitivity of 0.60 or more, it is preferably 0.5 to 5.0 parts by mass per 100 parts by mass of the polymerizable compound described below.
  • the composition for photochromic layer (1) may further contain, if necessary, a polymerizable compound that contributes to the curing of the composition for photochromic layer (1).
  • the polymerizable compound that may be contained in the photochromic layer composition (1) is not particularly limited, and examples thereof include polymerizable compounds that may be contained in the primer layer composition (3), photochromic layer composition (2), and protective layer composition (2) described below.
  • the content of the polymerizable compound is not particularly limited, but is preferably 70 to 99% by mass relative to 100% by mass of the composition (1) for photochromic layer.
  • the photochromic layer composition (1) may further contain, if necessary, a polymerization initiator that contributes to the curing of the photochromic layer composition (1).
  • the polymerizable compound that may be contained in the photochromic layer composition (1) is not particularly limited, and known compounds may be used, such as polymerization initiators that may be contained in the primer layer composition (3), photochromic layer composition (2), and protective layer composition (2) described below.
  • the content of the polymerization initiator is not particularly limited, but is preferably 0.1 to 10 parts by mass per 100 parts by mass of the composition (1) for photochromic layer.
  • the composition (1) for photochromic layer may further contain a dye that contributes to improving the antiglare properties of the photochromic layer, if necessary.
  • the dye is not particularly limited, but from the above viewpoint, a dye having an absorption peak in the range of 550 to 600 nm is preferred.
  • the dye having an absorption peak in the above range of 550 to 600 nm is not particularly limited, and examples thereof include known compounds such as nitro-based compounds, azo-based compounds, anthraquinone-based compounds, threne-based compounds, porphyrin-based compounds, and rare earth metal compounds. These may be used alone or in combination of two or more.
  • the photochromic layer composition (1) may further contain any amount of commonly used additives, such as surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, pigments, fragrances, plasticizers, and silane coupling agents. These may be used alone or in combination of two or more.
  • additives such as surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, pigments, fragrances, plasticizers, and silane coupling agents.
  • the photochromic layer composition (1) can be prepared by mixing the various components described above simultaneously or sequentially in any order.
  • photochromic layer composition (1) which may contain a polymerizable compound
  • examples include Transshade-SC (manufactured by Tokuyama Corporation, TRANSSHADE (registered trademark)).
  • One type of photochromic layer composition (1) may be used alone, or two or more types may be used.
  • the photochromic layer composition (1) is irradiated with light and cured to obtain the photochromic layer (1) which is a cured coating layer.
  • the photochromic layer (1) can be formed on the surface of the primer layer by applying a composition for photochromic layer (1) onto the surface of the primer layer (1) and subjecting the applied composition for photochromic layer (1) to a curing treatment.
  • the coating method is not particularly limited, and known coating methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of coating.
  • the curing treatment is not particularly limited, and examples thereof include light irradiation, heat treatment, etc. These may be used alone or in combination of two or more.
  • the intensity of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 50 to 350 mW/cm 2 , more preferably 100 to 300 mW/cm 2 , and particularly preferably 150 to 250 mW/cm 2 .
  • the irradiation time of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for photochromic layer, it is preferably 10 to 200 seconds, more preferably 25 to 150 seconds, and particularly preferably 40 to 100 seconds.
  • the exposure dose of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 0.5 to 70.0 J/cm 2 , more preferably 2.5 to 45.0 J/cm 2 , and particularly preferably 6.0 to 25.0 J/cm 2 .
  • an annealing treatment heat treatment
  • the conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 80 to 130°C.
  • each cured coating layer (excluding the hard coat layer) provided on the plastic lens (1) is not particularly limited, but is preferably 1 to 100 ⁇ m, more preferably 5 to 95 ⁇ m, and particularly preferably 10 to 90 ⁇ m. If the thickness is at or above the lower limit of the above range, it becomes easier to maintain weather resistance and adhesion, and if it is at or below the upper limit of the above range, it becomes easier to maintain the transmittance (transparency) of the cured coating layer.
  • a coating material means a material that suppresses the incidence of light in at least a part of a specific wavelength range
  • the specific wavelength range means a wavelength range to which a polymerizable composition for forming a photochromic layer, which is used to constitute a plastic lens, is sensitive.
  • the coating material provided on the plastic lens (1) will be described in more detail below.
  • coating material (1) can be a coating material with a maximum transmittance of 35% or less for light in the wavelength range of 280 to 450 nm when the polymerizable composition for forming a photochromic layer is sensitive to light in the wavelength range of 280 to 780 nm (hereinafter, sometimes simply referred to as "coating material (1)").
  • the thickness of the coating material (1) is preferably 5 to 150 ⁇ m, more preferably 10 to 100 ⁇ m, and especially preferably 15 to 50 ⁇ m. If the thickness is above the lower limit of the above range, light incidence from the edge surface will be more likely to be obstructed, while if the thickness is below the upper limit of the above range, a good appearance will be more likely to be ensured.
  • the coating material (1) are not particularly limited as long as they have a maximum transmittance of 35% or less for light in the wavelength range of 280 to 450 nm, and include, for example, adhesive tape, ink, resin film, rubber, and a cured coating layer formed by curing a polymerizable composition. These may be used alone or in combination of two or more types. Of these, adhesive tape and ink are preferred from the perspective of ease of coating.
  • the coating material (1) there are no particular restrictions on the coating material (1) as long as it covers the edge surface of the lens substrate, and the edge surface of the lens substrate may be coated with one layer or two or more layers.
  • covering material (1) Commercially available products for the covering material (1) are not particularly limited, and examples include UNI Posca Black (manufactured by Mitsubishi Pencil Co., Ltd.), UNI Posca White (manufactured by Mitsubishi Pencil Co., Ltd.), Macky Black (manufactured by Zebra Corporation), Polyimide Tape (manufactured by AS ONE Corporation), and Black Whiteboard Marker (Kokuyo Co., Ltd.). These may be used alone or in combination of two or more.
  • the coating material (1) is applied, and it may be applied at the very beginning of the production of the plastic lens (1), during production (for example, before or after the formation of a primer layer, before or after the formation of a photochromic layer, etc.), or after the production of the plastic lens (1).
  • it is preferable to apply the coating after the production of the plastic lens (1) considering that the peripheral portion of the plastic lens (1) on which the cured coating layer has been formed may need to be polished and ground to fit the size of an eyeglass frame, etc.
  • the plastic lens (2) includes a lens substrate, a photochromic layer formed on one surface of the lens substrate by curing a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range, and a coating material that coats the edge surface of the lens substrate and suppresses the incidence of light in at least a portion of the specific wavelength range onto the lens substrate, where the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 380 nm, the coating material has a transmittance of 15% or less for light with a wavelength of 365 nm, and the lens substrate has a transmittance of 10% or more for light with a wavelength of 365 nm.
  • the other cured coating layer may or may not have a cured coating layer other than the photochromic layer.
  • the other cured coating layer is not particularly limited, and examples thereof include a primer layer, a protective layer, a hard coat layer, and other functional layers, which will be described later.
  • the surface of the lens substrate opposite to the surface having the photochromic layer (hereinafter sometimes simply referred to as the "other surface of the lens substrate") may or may not have a cured coating layer other than the photochromic layer.
  • the lens substrate of the plastic lens (2) will be described in more detail below.
  • lens substrate (2) can be a lens substrate with a transmittance of 10% or more for light with a wavelength of 365 nm (hereinafter, sometimes simply referred to as "lens substrate (2)").
  • the transmittance of the lens substrate (2) for light with a wavelength of 365 nm is not particularly limited as long as it is 10% or more, but from the perspective of fully demonstrating the effects of the present disclosure, it is preferably 20% or more, and more preferably 30% or more.
  • lens substrate (1) For the material, color, refractive index, focal point, surface, thickness, and one surface of the lens substrate (2), please refer to the description of the lens substrate (1) above.
  • the plastic lens (2) may further include a primer layer, if necessary.
  • the primer layer that the plastic lens (2) may have hereinafter, may be simply referred to as "primer layer (2)" will be described in more detail below.
  • the primer layer (2) there are no particular restrictions on the location of the primer layer (2), but from the perspective of improving adhesion between the lens substrate and the photochromic layer, it is preferably located between the lens substrate (2) described above and the photochromic layer (2) described below.
  • the thickness of the primer layer (2) is preferably 0.1 to 20.0 ⁇ m, more preferably 0.3 to 15 ⁇ m, and particularly preferably 0.5 to 10 ⁇ m. If the thickness is equal to or greater than the lower limit of the above range, good adhesion between the lens substrate and the photochromic layer will be achieved, and if the thickness is equal to or less than the upper limit of the above range, a good appearance will be more easily achieved.
  • the primer layer (2) is a cured coating layer obtained by curing a polymerizable composition for forming a primer layer (hereinafter sometimes simply referred to as the "primer layer composition").
  • primer layer composition used to form the primer layer (2) can be a primer layer composition that can be prepared from a known adhesive (hereinafter, sometimes simply referred to as "primer layer composition (2)").
  • primer layer composition (2) the description of the primer layer composition (1) can be referred to.
  • primer layer composition (3) a primer layer composition containing a polyisocyanate, a hydroxy group-containing polymerizable compound, and at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, the polymerizable compound having a viscosity of 100 cP or less.
  • the components contained in the primer layer composition (3) are not particularly limited, but it is preferable that the composition contain the above three components from the viewpoint of suppressing attenuation of photochromic properties caused by the primer layer and from the viewpoint of adhesion to the photochromic layer.
  • the various components contained in the primer layer composition (3) will be described in more detail below.
  • the polyisocyanate is a compound having two or more isocyanate groups in one molecule.
  • the number of isocyanate groups contained in one molecule of the polyisocyanate is not particularly limited, but is preferably 2 to 6, more preferably 3 to 5, and particularly preferably 3 to 4. When the number is at least the lower limit of the above range, the water resistance of the primer layer is likely to be improved, and when the number is at most the upper limit of the above range, adhesion to the lens substrate is likely to be improved.
  • the molecular weight of the polyisocyanate is preferably 200 to 800, more preferably 300 to 700, and especially preferably 400 to 600. If it is above the lower limit of the above range, it will be easier to adhere to the lens substrate, and if it is below the upper limit of the above range, the water resistance of the primer layer will be improved.
  • polyisocyanate examples include, for example, aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate; aliphatic or alicyclic diisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-bisisocyanatomethylcyclohexane, and tetramethylxylylene diisocyanate; etc.
  • aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyan
  • polyisocyanates exemplified above may be allophanate, adduct, biuret, or isocyanurate, and may be used alone or in combination of two or more.
  • commercially available polyisocyanates are not particularly limited, and examples thereof include those manufactured by Tosoh Corporation such as Coronate HX, Coronate HXR, Coronate HXLV, Coronate HK, Coronate 2715, Coronate HL, Coronate L, Coronate 2037, HDI, TDI, and MDI; and those manufactured by Mitsui Chemicals, Inc.
  • Takenate 500, Takenate 600, Duranate 24A-100, TPA-100, TKA-100, P301-75E Takenate D-110N, D-120N, D-127N, D-140N, D-160N, D15N, D-170N, D-170HN, D-172N, D-177N, D-178N, and D-101E. These may be used alone or in combination of two or more.
  • the number of hydroxy groups contained in one molecule of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 1 to 6, more preferably 1 to 5, and particularly preferably 2 to 4.
  • the reaction efficiency with polyisocyanate tends to be good
  • the number is equal to or less than the upper limit of the above range
  • adhesion to the photochromic layer tends to be good.
  • the present inventors speculate that the urethane bond formed by reacting the isocyanate group of the polyisocyanate with the hydroxy group of the hydroxy group-containing polymerizable compound contributes to improving the adhesion of the primer layer.
  • the hydroxy group-containing polymerizable compound is a (meth)acrylate.
  • the number of functional groups of the (meth)acrylate is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 2 to 3.
  • the (meth)acryloyl group, which is the functional group may contain only acryloyl groups, may contain only methacryloyl groups, or may contain acryloyl groups and methacryloyl groups. In one embodiment, from the viewpoint of adhesion, it is preferable that the hydroxy group-containing polymerizable compound contains only acryloyl groups as the (meth)acryloyl groups.
  • the molecular weight of the hydroxyl group-containing polymerizable compound is not particularly limited, but is preferably 100 to 600, more preferably 200 to 500, and particularly preferably 300 to 400. If the molecular weight is above the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and if the molecular weight is below the upper limit of the above range, adhesion to the photochromic layer tends to be good.
  • the (meth)acrylate are not particularly limited and include, for example, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanedimethanol monoacrylate, 2-hydroxy-1-acryloxy-3-methadryloxypropane, 2-hydroxy-1-3-dimethacryloxypropane, pentaerythritol tetraacrylate, 2-hydroxy-3-phenoxypropyl acrylate, monoacryloxyethyl hexahydrophthalate, 2-acryloyloxyethyl phthalate, 2-(acryloxyoxy)ethyl 2-hydroxyethyl phthalate, and compounds represented by the following formula (1): These may be used alone or in combination of two or more.
  • hydroxy group-containing polymerizable compound is a hydroxy group-containing polymerizable compound having an amide group.
  • the hydroxy group-containing polymerizable compound having an amide group is not particularly limited, and examples thereof include N-(2-hydroxyethyl)acrylamide.
  • hydroxy group-containing polymerizable compounds having an epoxy ester structure are not particularly limited, and examples thereof include Epoxy Ester 40EM (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 70PA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 200PA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002M(N) (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002A(N) (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000MK (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000A (manufactured by Kyoeisha Chemical Co., Ltd.), etc. These may be used alone or in combination of two or more.
  • the primer layer composition (3) preferably contains at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, and having a viscosity of 100 cP (centipoise) or less (hereinafter, sometimes simply referred to as a "low-viscosity polymerizable compound").
  • the present inventors speculate that the primer layer composition (3) containing the low-viscosity polymerizable compound suppresses attenuation of photochromic properties caused by the primer layer.
  • the viscosity of the low-viscosity polymerizable compound there are no particular restrictions on the viscosity of the low-viscosity polymerizable compound, as long as it is 100 cP or less. However, from the viewpoints of ease of handling and preventing the occurrence of optical defects, it is preferably 5 to 70 cP, and more preferably 10 to 50 cP.
  • the number of functional groups of the (meth)acrylate, which is one form of the low-viscosity polymerizable compound, is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 1 (monofunctional) to 2.
  • the (meth)acrylate, which is one form of the low-viscosity polymerizable compound can contain an aryl group (e.g., a phenyl group), an amide group, etc.
  • a "vinyl ether” refers to a compound having one or more vinyl groups and one or more ether bonds in one molecule, preferably having two or more vinyl groups in one molecule, and more preferably having two to four vinyl groups in one molecule.
  • the number of ether bonds contained in the vinyl ether is preferably two to four in one molecule.
  • the molecular weight of the low-viscosity polymerizable compound is preferably 100 to 300, and more preferably 150 to 250. If it is at or above the lower limit of the above range, it becomes easier to suppress the occurrence of optical defects, and if it is at or below the upper limit of the above range, it becomes easier to adhere to the photochromic layer.
  • the low-viscosity polymerizable compound are not particularly limited and include, for example, 2-phenoxyethyl (meth)acrylate, acrylamide, methoxypolyethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, stearyl (meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, phenoxy Diethyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated poly
  • the content of the low-viscosity polymerizable compound is not particularly limited, but is preferably 30.0 to 90.0 mass%, more preferably 35.0 to 80.0 mass%, and particularly preferably 40.0 to 70.0 mass%, relative to 100 mass% of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.
  • the thickness is equal to or greater than the lower limit of the above range, the film is easy to handle, and when the thickness is equal to or less than the upper limit of the above range, the film is easily adhered to the lens substrate.
  • the low-viscosity polymerizable compound is the component contained in the largest amount in the primer layer composition (3) containing the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.
  • the content of the polyisocyanate is not particularly limited, but is preferably 5.0 to 75.0 mass%, more preferably 10.0 to 55.0 mass%, and particularly preferably 15.0 to 35.0 mass%, relative to 100 mass% of the total of the low-viscosity polymerizable compound, the polyisocyanate, and the hydroxy group-containing polymerizable compound.
  • the thickness is equal to or greater than the lower limit of the above range, the water resistance of the primer layer is likely to be improved, and when the thickness is equal to or less than the upper limit of the above range, adhesion to the lens substrate is likely to be improved.
  • the content of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 3.0 to 30.0 mass%, more preferably 5.0 to 25.0 mass%, and particularly preferably 7.0 to 20.0 mass%, relative to 100 mass% in total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.
  • content is equal to or greater than the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and when the content is equal to or less than the upper limit of the above range, adhesion to the photochromic layer tends to be good.
  • the primer layer composition (3) may further contain a polymerization initiator, if necessary.
  • the blending amount of the polymerization initiator is not particularly limited, and from the viewpoint of the efficiency of primer layer formation and adhesion to the photochromic layer, it is preferably 0.01 to 3.0 parts by mass per 100 parts by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.
  • the polymerization initiator is not particularly limited, and known polymerization initiators can be used.
  • the known polymerization initiator is not particularly limited, and examples thereof include a photoradical polymerization initiator and a thermal polymerization initiator. These may be used alone or in combination of two or more. Among these, a photoradical polymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time.
  • a photoradical polymerization initiator see the polymerization initiators that can be contained in the composition for photochromic layer (2) described below.
  • the primer layer composition (3) may or may not contain a solvent.
  • any solvent can be used without any particular limitation as long as it does not inhibit the progress of the polymerization reaction of the polymerizable composition.
  • the amount of the solvent is not particularly limited, but from the viewpoint of suppressing optical defects, the amount of the solvent is preferably 10.0 parts by mass or less, more preferably 5.0 parts by mass or less, and particularly preferably 3.0 parts by mass or less, per 100 parts by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.
  • the primer layer composition (3) may further contain, if necessary, any amount of known additives that are typically added to compositions for forming a primer layer, such as silicone surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, leveling agents for improving the coating suitability of the composition, inorganic oxide particles that contribute to improving the weather resistance of plastic lenses, etc. These may be used alone or in combination of two or more.
  • additives that are typically added to compositions for forming a primer layer, such as silicone surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, leveling agents for improving the coating suitability of the composition, inorganic oxide particles that contribute to improving the weather resistance of plastic lenses, etc. These may be used alone or in combination of two
  • the blending amount of the above-mentioned known additives is not particularly limited as long as the effect of the primer layer is exhibited, and is preferably 1.0 to 20.0 parts by mass, more preferably 1.5 to 10.0 parts by mass, and particularly preferably 2.0 to 5.0 parts by mass, relative to 100 parts by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.
  • the contents of the low-viscosity polymerizable compound, polyisocyanate, and hydroxyl group-containing polymerizable compound are not particularly limited as long as they exhibit the effects of the primer layer, and are preferably 80.0 to 100.0 mass%, more preferably 85.0 to 100.0 mass%, and more preferably 90.0 to 100.0 mass%, based on 100 mass% of primer layer composition (3) (excluding the polymerization initiator).
  • the primer layer composition (3) can be prepared by mixing the various components described above simultaneously or sequentially in any order.
  • the primer layer (2) can be formed on one surface of the lens substrate by applying the primer layer composition (2) or (3) to one surface of the lens substrate and then subjecting the applied primer layer composition to a curing treatment.
  • the coating method is not particularly limited, and known coating methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of coating.
  • the curing treatment for curing the primer layer composition (2) includes a drying treatment.
  • the drying treatment is not particularly limited, and can be carried out, for example, by placing the substrate in an atmosphere at room temperature to 100° C. for 5 minutes to 24 hours.
  • the curing treatment for curing the primer layer composition (3) is not particularly limited, and examples thereof include light irradiation and heat treatment.
  • the conditions for the light irradiation curing treatment can be determined depending on the types of various components contained in the primer layer composition (3) and the composition of the primer layer composition (3). After the light irradiation curing treatment, an annealing treatment (heat treatment) can also be performed as necessary.
  • the conditions for the annealing treatment are not particularly limited, but it is preferable to perform the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.
  • the photochromic layer provided on the plastic lens (2) is a cured coating layer obtained by curing a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range.
  • the photochromic layer provided on the plastic lens (2) (hereinafter, sometimes simply referred to as "photochromic layer (2)") will be described in more detail below.
  • One form of the photochromic layer (2) can be a cured product of a photochromic layer-forming polymerizable composition (hereinafter sometimes simply referred to as a "photochromic layer composition") that is sensitive to light in a wavelength range of 280 to 380 nm and exhibits photochromic properties.
  • the position of the photochromic layer (2) is not particularly limited, but from the viewpoint of adhesion to the lens substrate and protection of the photochromic layer, it is preferably between the primer layer (2) described above and the protective layer (2) described below.
  • the wavelength range to which the photochromic layer (2) is sensitive depends on the type of polymerization initiator, but is not particularly limited as long as it is between 280 and 380 nm, preferably between 310 and 380 nm, more preferably between 340 and 375 nm, and particularly preferably between 350 and 370 nm. If the wavelength is above the lower limit of the above range, destruction of the photochromic compound by ultraviolet rays is more easily suppressed, and if the wavelength is below the upper limit of the above range, sensitivity is increased.
  • the thickness of the photochromic layer (2) is preferably 5 to 80 ⁇ m, more preferably 10 to 70 ⁇ m, and particularly preferably 15 to 60 ⁇ m. If the thickness is above the lower limit of the above range, the color density tends to become stronger, while if the thickness is below the upper limit of the above range, it becomes easier to maintain transparency.
  • composition for photochromic layer composition (2) One form of the composition for photochromic layer that is sensitive to light in the wavelength range of 280 to 380 nm can be a composition for photochromic layer containing a (meth)acrylate and a photochromic compound (hereinafter, sometimes simply referred to as “composition for photochromic layer (2)”). Furthermore, the photochromic layer composition (2) may further contain a polymerizable compound, a polymerization initiator, and the like, if necessary. The various components contained in the composition for photochromic layer (2) will be described in more detail below.
  • the (meth)acrylate contained in the photochromic layer composition (2) is not particularly limited, and examples thereof include a polyfunctional (meth)acrylate having a molecular weight of 500 or more (hereinafter also referred to as "component A”), a monofunctional (meth)acrylate (hereinafter also referred to as “component B”), a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure (hereinafter also referred to as "component C”), and a bifunctional (meth)acrylate having at least one structure selected from the group consisting of a cyclic structure and a branched structure (hereinafter also referred to as "component D"). These may be used alone or in combination of two or more.
  • component A polyfunctional (meth)acrylate having a molecular weight of 500 or more
  • component B monofunctional (meth)acrylate
  • component C polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure
  • Component A-- The molecular weight of Component A is not particularly limited as long as it is 500 or more, but is preferably 600 to 2000, more preferably 650 to 1500, and particularly preferably 700 to 1300. If the molecular weight is equal to or greater than the lower limit of the above range, the fading rate tends to be improved, and if the molecular weight is equal to or less than the upper limit of the above range, the photochromic layer tends to have a high hardness.
  • the component A is not particularly limited, and examples thereof include bifunctional (meth)acrylates, trifunctional (meth)acrylates, tetrafunctional (meth)acrylates, and pentafunctional (meth)acrylates. These may be used alone or in combination of two or more. Among these, from the viewpoint of weather resistance, bifunctional or trifunctional (meth)acrylates are preferred.
  • the (meth)acryloyl group of the above-mentioned component A may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups. That is, component A can be an acrylate or a methacrylate.
  • component A includes a non-cyclic polyfunctional (meth)acrylate.
  • non-cyclic means not containing a cyclic structure.
  • cyclic means containing a cyclic structure.
  • the non-cyclic polyfunctional (meth)acrylate refers to a bifunctional or higher functional (meth)acrylate that does not contain a cyclic structure.
  • Specific examples of Component A are not particularly limited and include, for example, polyalkylene glycol di(meth)acrylates represented by the following formula (2): These may be used alone or in combination of two or more.
  • R 1 and R 2 each independently represent a hydrogen atom or a methyl group
  • R represents an alkylene group
  • n represents the number of repetitions of the alkoxy group represented by RO and is 2 or more.
  • the number of carbon atoms in the alkylene group represented by R in formula (2) is not particularly limited, but is preferably 1 to 5, and more preferably 2 to 4.
  • the alkylene group represented by R in formula (2) is not particularly limited, and examples thereof include an ethylene group, a propylene group, and a tetramethylene group.
  • n in formula (2) is not particularly limited, it is preferably 2 to 30, more preferably 2 to 25, and particularly preferably 2 to 20.
  • the polyalkylene glycol di(meth)acrylate represented by formula (2) is not particularly limited, and examples thereof include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, etc. These may be used alone or in combination of two or more.
  • component A is a tri(meth)acrylate represented by the following formula (3).
  • the (meth)acryloyl group of the tri(meth)acrylate represented by formula (3) may contain only acryloyl groups, may contain only methacryloyl groups, or may contain acryloyl groups and methacryloyl groups.
  • R 40 , R 41 , R 44 , R 45 , R 47 and R 48 each independently represent an alkylene group
  • R 43 represents an alkyl group
  • R 42 , R 46 and R 49 each independently represent a hydrogen atom or a methyl group.
  • n1 represents the number of repeating alkoxy groups represented by OR 41 and is 2 or more.
  • n2 represents the number of repeating alkoxy groups represented by OR 45 and is 2 or more.
  • n3 represents the number of repeating alkoxy groups represented by OR 48 and is 2 or more.
  • R 41 , R 45 and R 48 in formula (3) are as described above for R in formula (2).
  • n1, n2 and n3 in formula (3) are as described above for n in formula (2).
  • R 41 , R 45 and R 48 may be the same, or two or three may be different. This also applies to n1, n2 and n3.
  • R 42 , R 46 and R 49 each independently represent a hydrogen atom or a methyl group.
  • the tri(meth)acrylate represented by formula (3) may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.
  • the number of carbon atoms in the alkyl group represented by R 43 in formula (3) is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4.
  • the alkyl group represented by R 43 in formula (3) is a linear alkyl group or a branched alkyl group. Specific examples of the alkyl group represented by R 43 in formula (3) are not particularly limited, and include, for example, a methyl group and an ethyl group.
  • R 40 , R 44 and R 47 each independently represent an alkylene group.
  • the number of carbon atoms in the alkylene groups represented by R 40 , R 44 and R 47 in formula (3) is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4.
  • Specific examples of the alkylene group represented by R 40 , R 44 and R 47 in formula (3) are not particularly limited and include, for example, a methylene group, an ethylene group, a propylene group, a tetramethylene group and the like.
  • the tri(meth)acrylate represented by formula (3) is not particularly limited, and examples include trimethylolpropane polyoxyethylene ether tri(meth)acrylate. These may be used alone or in combination of two or more.
  • Component B-- Component B is a monofunctional (meth)acrylate represented by the following formula (4).
  • R 10 represents a hydrogen atom or a methyl group.
  • the monofunctional (meth)acrylate represented by formula (4) may be an acrylate or a methacrylate.
  • R 11 represents a linear alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms.
  • the alkyl group represented by R11 in formula (4) may be unsubstituted or may have a substituent.
  • the substituent is not particularly limited, and examples thereof include the various substituents described above.
  • the number of carbon atoms in the linear or branched alkyl group represented by R 11 in formula (4) is not particularly limited, but is preferably 3 to 15, more preferably 3 to 14, and particularly preferably 3 to 12.
  • the content is equal to or greater than the lower limit of the above range, the color density of the photochromic layer tends to be high, whereas if the content is equal to or less than the upper limit of the above range, the photochromic compound tends to dissolve in the composition for the photochromic layer.
  • the molecular weight of the monofunctional (meth)acrylate represented by formula (4) may be, for example, 100 to 300. However, it is not limited to the above range.
  • the monofunctional (meth)acrylate represented by formula (4) may be a monofunctional (meth)acrylate having a molecular weight of 150 or less.
  • Specific examples of the monofunctional (meth)acrylate represented by formula (4) are not particularly limited and include, for example, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, n-lauryl (meth)acrylate, etc. These may be used alone or in combination of two or more.
  • the polyfunctional (meth)acrylate other than Component A that can be contained in the (meth)acrylate is not particularly limited, but from the viewpoint of increasing the (meth)acryloyl group content in the composition for photochromic layer (2) and forming a rigid polymer network between molecules, a (meth)acrylate having a high proportion of (meth)acryloyl groups in the molecule is preferred. From this viewpoint, a polyfunctional (meth)acrylate having a smaller molecular weight than Component A is preferred.
  • the molecular weight of the polyfunctional (meth)acrylate other than component A is not particularly limited, but from the above viewpoint, it is preferably 100 or more and less than 500, more preferably 100 to 400, and particularly preferably 100 to 350.
  • the number of functional groups of the polyfunctional (meth)acrylate other than Component A is preferred.
  • the number of functional groups of the polyfunctional (meth)acrylate can be, for example, 10 to 15.
  • polyfunctional (meth)acrylates having 10 to 15 functional groups include poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives. These may be used alone or in combination of two or more.
  • the polyfunctional (meth)acrylate is not particularly limited, and examples thereof include a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure (component C), a bifunctional (meth)acrylate having at least one structure selected from the group consisting of a cyclic structure and a branched structure (component D), etc. These may be used alone or in combination of two or more. Components C and D will be described in more detail below.
  • Component C-- Component C is a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure, represented by the following formula (5).
  • R3 and R4 each independently represent a hydrogen atom or a methyl group.
  • m represents an integer of 1 or more, and may be 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less.
  • component C there are no particular restrictions on the molecular weight of component C, but it is preferably 100 to 400, more preferably 140 to 350, and especially preferably 160 to 300. If it is above the lower limit of the above range, the fading rate tends to be improved, while if it is below the upper limit of the above range, the color density of the photochromic layer tends to be increased.
  • the component C may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.
  • Specific examples of the component C are not particularly limited and include, for example, 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, etc. These may be used alone or in combination of two or more.
  • Component D-- Component D is a bifunctional (meth)acrylate containing at least one structure selected from the group consisting of a cyclic structure and a branched structure. It is presumed that the inclusion of the component D in the composition for photochromic layer (2) contributes to improving the color density of the photochromic layer formed from the composition for photochromic layer (2).
  • component D contains one or more cyclic structures and no branched structures in one molecule, in another embodiment, it contains one or more branched structures and no cyclic structures in one molecule, and in still another embodiment, it contains one or more cyclic structures and one or more branched structures in one molecule.
  • the number of at least one structure selected from the group consisting of cyclic structures and branched structures contained in the above component D is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1.
  • the component D has a methacryloyl group
  • the branched structure contained in the methacryloyl group is not taken into consideration.
  • component D containing one or more cyclic structures is an alicyclic bifunctional (meth)acrylate.
  • the alicyclic bifunctional (meth)acrylate is not particularly limited, and examples thereof include compounds having a structure represented by R 111 -(L 11 ) n11 -Q-(L 22 ) n22 -R 222 .
  • Q represents a divalent alicyclic group
  • R 111 and R 222 each independently represent a (meth)acryloyl group or a (meth)acryloyloxy group
  • L 11 and L 22 each independently represent a linking group
  • n11 and n22 each independently represent 0 or 1.
  • the divalent alicyclic group represented by Q is not particularly limited, and suitable examples thereof include alicyclic hydrocarbon groups having 3 to 20 carbon atoms, such as a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, a tricyclodecanylene group, and an adamantylene group.
  • the linking group represented by L 11 and L 22 is not particularly limited, and examples thereof include alkylene groups having 1 to 6 carbon atoms.
  • alicyclic bifunctional (meth)acrylates are not particularly limited and include, for example, cyclohexanedimethanol di(meth)acrylate, ethoxylated cyclohexanedimethanol di(meth)acrylate, propoxylated cyclohexanedimethanol di(meth)acrylate, ethoxylated propoxylated cyclohexanedimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated tricyclodecane dimethanol di(meth)acrylate, propoxylated tricyclodecane dimethanol di(meth)acrylate, and ethoxylated propoxylated tricyclodecane dimethanol di(meth)acrylate. These may be used alone or in combination of two or more.
  • Component D containing one or more branched structures is, for example, a bifunctional (meth)acrylate containing a branched alkylene group.
  • the number of carbon atoms in the branched alkylene group is not particularly limited, but is preferably 1 to 10, more preferably 2 to 9, even more preferably 3 to 8, and particularly preferably 4 to 7.
  • One embodiment of the branched alkylene group may contain a quaternary carbon (i.e., a carbon bonded to four carbons).
  • Component D containing one or more branched structures are not particularly limited and include, for example, neopentyl glycol di(meth)acrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, etc. These may be used alone or in combination of two or more.
  • the molecular weight of component D is not particularly limited, but is preferably between 200 and 400. If it is above the lower limit of the above range, the color density of the photochromic layer is more likely to be improved, and if it is below the upper limit of the above range, the photochromic compound is more likely to dissolve in the composition for the photochromic layer.
  • Component D may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.
  • the content of the polymerizable compound (i.e., the total content of the multiple polymerizable compounds) is not particularly limited, but is preferably 70 to 99 mass %, more preferably 80 to 95 mass %, relative to 100 mass % of the composition for photochromic layer (2). If the content is equal to or greater than the lower limit of the above range, the photochromic compound becomes more easily soluble in the composition for photochromic layer, and if the content is equal to or less than the upper limit of the above range, the photochromic properties tend to be improved.
  • the photochromic layer composition (2) may or may not contain a solvent. When the composition (2) contains a solvent, any solvent can be used in any amount as long as it does not inhibit the polymerization reaction of the polymerizable composition.
  • the content of Component A is not particularly limited, but is preferably 50 to 95% by mass, more preferably 55 to 92% by mass, and particularly preferably 60 to 90% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2).
  • the content is equal to or greater than the lower limit of the above range, the fading rate is likely to be improved, and when the content is equal to or less than the upper limit of the above range, weather resistance is likely to be improved.
  • a component that corresponds to both Component A and Component C, or Component A and Component D, is considered to be Component A.
  • Component A can be the component that accounts for the largest proportion of multiple polymerizable compounds contained in the composition.
  • the composition for photochromic layer (2) may contain only one type of component A, and in another embodiment, it may contain two or more types of component A. When two or more types of component A are contained, the content of component A is the total content of the two or more types. This also applies to the contents of other components.
  • the content of Component B is not particularly limited, but is preferably 1 to 30% by mass, more preferably 5 to 27% by mass, and particularly preferably 10 to 25% by mass, relative to 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2).
  • the content is equal to or greater than the lower limit of the above range, weather resistance is likely to be improved, and when the content is equal to or less than the upper limit of the above range, the fading rate is likely to be improved.
  • the composition for photochromic layer (2) may contain only one type of component B, and in another embodiment, it may contain two or more types of component B. When two or more types of component B are contained, the content of component B is the total content of the two or more types.
  • the content of Component C is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 3 to 27% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2). If the content is equal to or greater than the lower limit of the above range, the color density tends to increase, whereas if the content is equal to or less than the upper limit of the above range, the fading rate tends to increase.
  • the composition for photochromic layer (2) may contain only one type of component C, and in another embodiment, it may contain two or more types of component C. When two or more types of component C are contained, the content of component C is the total content of the two or more types.
  • the content of Component D is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 5 to 27% by mass, relative to 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2).
  • the content is equal to or greater than the lower limit of the above range, the color density of the photochromic layer is likely to be improved, and when the content is equal to or less than the upper limit of the above range, the photochromic compound is likely to dissolve in the composition for photochromic layer.
  • the composition for photochromic layer (2) may contain only one type of component D, and in another embodiment, it may contain two or more types of component D. When two or more types of component D are contained, the content of component D is the total content of the two or more types.
  • the composition (2) for photochromic layer may or may not contain, as necessary, other (meth)acrylates other than components A to D.
  • the content of the other (meth)acrylates other than components A to D is not particularly limited, but from the viewpoint of the fading rate, it is preferably 10.0% by mass or less, and more preferably 5.0% by mass or less, relative to 100% by mass of all (meth)acrylates contained in the composition (2) for photochromic layer.
  • the photochromic layer composition (2) may or may not contain a polymerizable compound other than a (meth)acrylate, as necessary.
  • photochromic compound (2) The photochromic compound contained in the composition for photochromic layer (2) (hereinafter, sometimes simply referred to as "photochromic compound (2)") is not particularly limited, and any known compound can be used, as long as the composition for photochromic layer (2) is sensitive to light in the wavelength range of 280 to 380 nm and exhibits photochromic properties.
  • the photochromic compound (2) are not particularly limited and include, for example, compounds having a known skeleton that exhibits photochromic properties, such as azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbismidazoles, donor-acceptor Stenhouse adducts (DASA), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, and stilbenes; fulgimide compounds; spirooxazine compounds; chromene compounds; indeno-fused naphthopyran compounds; and at least one compound selected from the group consisting of photochromic compounds represented by general formula A, general formula B, and general formula C described in WO 2022/138966; and the like. These compounds may be used alone or
  • the composition (2) for photochromic layer may contain, as necessary, one or more of various additives that can be typically contained in polymerizable compositions, in any amount.
  • the additives that can be contained in the composition (2) for photochromic layer are not particularly limited, and examples thereof include a polymerization initiator for promoting the polymerization reaction and inorganic oxide particles that contribute to improving the weather resistance of the photochromic layer.
  • the polymerization initiator is not particularly limited, and examples include photoradical polymerization initiators and thermal polymerization initiators. These may be used alone or in combination of two or more. Among these, photoradical polymerization initiators are preferred from the viewpoint of progressing the polymerization reaction in a short time.
  • the photoradical polymerization initiator is not particularly limited, and examples thereof include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one; ⁇ -hydroxyketones such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; ⁇ -aminoketones such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; oxime esters such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and 2,4,6-trimethylbenzo
  • 2,4,5-triarylimidazole dimers such as 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone compounds such as benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone; 2-ethylanthraquinone, phenanthrenequinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2, Examples of suitable compounds include quinone compounds such as 3-diphenylanthraquinone, 1-
  • These compounds may be used alone or in combination of two or more.
  • ⁇ -hydroxyketones and phosphine oxides are preferred from the viewpoints of curability, transparency, and heat resistance.
  • the substituents on the aryl groups of the two triarylimidazole moieties may be the same, making the compound symmetrical, or different, making the compound asymmetrical.
  • a thioxanthone compound may be combined with a tertiary amine, such as the combination of diethylthioxanthone and dimethylaminobenzoic acid.
  • the content of the polymerization initiator is not particularly limited, but is preferably about 0.1 to 5.0% by mass relative to 100% by mass of the composition (2) for photochromic layer.
  • the inorganic oxide particles are not particularly limited, and examples thereof include metal oxide particles such as tungsten oxide ( WO3 ), zinc oxide (ZnO), silicon oxide ( SiO2 ), aluminum oxide ( Al2O3 ), titanium oxide ( TiO2 ), zirconium oxide ( ZrO2 ), tin oxide ( SnO2 ), beryllium oxide ( BeO ), and antimony oxide ( Sb2O5 ). These may be used alone or in combination of two or more. In this disclosure and this specification, the term "metal” also includes metalloids. Furthermore, although the composition formula of an oxide with a stoichiometric composition is shown in parentheses above, the oxide that constitutes the inorganic oxide particles is not limited to an oxide with a stoichiometric composition.
  • the photochromic layer composition (2) may further contain any amount of commonly used known additives, such as surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, and leveling agents for improving the coating suitability of the composition. These may be used alone or in combination of two or more.
  • additives such as surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, and leveling agents for improving the coating suitability of the composition.
  • the photochromic layer composition (2) can be prepared by mixing the various components described above simultaneously or sequentially in any order.
  • the photochromic layer composition (2) is irradiated with light and cured to obtain the photochromic layer (2) which is a cured coating layer.
  • the photochromic layer (2) can be formed on the surface of the primer layer by applying the photochromic layer composition (2) onto the surface of the primer layer and subjecting the applied photochromic layer composition (2) to a curing treatment.
  • the coating method is not particularly limited, and known coating methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of coating.
  • the curing treatment is not particularly limited, and examples thereof include light irradiation, heat treatment, etc. These may be used alone or in combination of two or more.
  • the intensity of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 50 to 350 mW/cm 2 , more preferably 100 to 300 mW/cm 2 , and particularly preferably 150 to 250 mW/cm 2 .
  • the irradiation time of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for photochromic layer, it is preferably 10 to 200 seconds, more preferably 25 to 150 seconds, and particularly preferably 40 to 100 seconds.
  • the exposure dose of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 0.5 to 70.0 J/cm 2 , more preferably 2.5 to 45.0 J/cm 2 , and particularly preferably 6 to 25.0 J/cm 2 .
  • an annealing treatment heat treatment
  • the conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 80 to 130°C.
  • the plastic lens (2) may further include a protective layer, if necessary.
  • the protective layer that the plastic lens (2) may have hereinafter, sometimes simply referred to as "protective layer (2)" will be described in more detail below.
  • the position of the protective layer (2) is not particularly limited, but from the viewpoint of protecting the photochromic layer, it is preferably on the photochromic layer (2). From this viewpoint, the protective layer preferably has high hardness.
  • the protective layer is not particularly limited, but preferably has excellent solvent resistance. In the manufacturing process of an optical article, after a layer is formed, a wiping treatment with a solvent is usually carried out to clean the surface of the formed layer, but if the protective layer is damaged in this wiping treatment, it may cause clouding or optical defects in the plastic lens.
  • the thickness of the protective layer (2) is preferably 10 to 50 ⁇ m, more preferably 12 to 45 ⁇ m, and particularly preferably 15 to 40 ⁇ m. If it is at or above the lower limit of the above range, the weather resistance of the plastic lens will be improved, and if it is at or below the upper limit of the above range, it will be easier to maintain the transmittance (transparency) of the cured coating layer.
  • the protective layer (2) is a cured coating layer obtained by curing a polymerizable composition for forming a protective layer (hereinafter sometimes simply referred to as the "protective layer composition").
  • One form of the protective layer composition used to form the protective layer (2) can be a polymerizable composition containing one or more (meth)acrylates and containing 70.0 mass% or more of an alicyclic bifunctional (meth)acrylate relative to 100 mass% of all (meth)acrylates (hereinafter, sometimes simply referred to as "protective layer composition (2)").
  • the components contained in the protective layer composition (2) are not particularly limited, but from the viewpoint of hardness and solvent resistance of the protective layer, it is preferable that the composition contain an alicyclic bifunctional (meth)acrylate component.
  • the alicyclic bifunctional (meth)acrylate contained in the composition (2) for protective layer the alicyclic bifunctional (meth)acrylate as an example of the composition (2) for photochromic layer described above can be referred to.
  • the content of the alicyclic bifunctional (meth)acrylate is not particularly limited, but from the viewpoint of obtaining higher hardness and better solvent resistance of the protective layer, it is preferably 70.0 mass% or more, more preferably 75.0 mass% or more, even more preferably 85.0 mass% or more, and particularly preferably 95.0 mass% or more, based on 100 mass% of all (meth)acrylates.
  • the total amount of (meth)acrylate may be the alicyclic bifunctional (meth)acrylate.
  • the protective layer composition (2) may contain one or more other (meth)acrylates in addition to an alicyclic bifunctional (meth)acrylate as the (meth)acrylate.
  • the (meth)acrylate may contain only an alicyclic bifunctional (meth)acrylate.
  • the other (meth)acrylate contained together with the alicyclic bifunctional (meth)acrylate is not particularly limited, and one or more of various (meth)acrylates can be used.
  • Specific examples of the other (meth)acrylate are not particularly limited, and include, for example, monofunctional, bifunctional, trifunctional, tetrafunctional, and pentafunctional (meth)acrylates, which may be acyclic or cyclic.
  • the (meth)acrylate containing a cyclic structure may have an alicyclic structure as the cyclic structure, or may have another cyclic structure.
  • the content of the other (meth)acrylates is not particularly limited, but from the viewpoint of obtaining high hardness and excellent solvent resistance in the protective layer, the content is preferably 0 to 30.0 mass%, more preferably 1.0 to 25.0 mass%, and particularly preferably 5.0 to 20.0 mass%, relative to 100 mass% of all (meth)acrylates.
  • the protective layer composition (2) contains at least one (meth)acrylate as a polymerizable compound, and in one embodiment, may contain one or more polymerizable compounds other than (meth)acrylate, or in another embodiment, may contain only (meth)acrylate as a polymerizable compound.
  • the other polymerizable compound is not particularly limited, and one or more known polymerizable compounds may be used.
  • the content of the (meth)acrylate is not particularly limited, but from the viewpoint of durability, it is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 100% by mass, of all polymerizable compounds in the protective layer composition (2).
  • the content of the (meth)acrylate (the total amount when two or more (meth)acrylates are contained) is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 95.0% by mass or more, based on 100% by mass of the protective layer composition (2).
  • the protective layer composition (2) may or may not contain a solvent. If it contains a solvent, there are no particular restrictions on the solvent that can be used, and any solvent can be used in any amount as long as it does not inhibit the polymerization reaction of the polymerizable composition.
  • the protective layer composition (2) may further contain one or more additives in any amount, if necessary.
  • the additives are not particularly limited and include, for example, various known additives such as a polymerization initiator for promoting the polymerization reaction, a surfactant such as a silicone surfactant for improving the coating suitability of the composition, etc. These may be used alone or in combination of two or more.
  • the polymerization initiator is not particularly limited, and examples thereof include a photoradical polymerization initiator and a thermal polymerization initiator. These may be used alone or in combination of two or more. Among these, a photoradical polymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time. Specific examples of the photoradical polymerization initiator can be found in the polymerization initiators that can be contained in the polymerizable composition for forming a photochromic layer described above.
  • the content of the polymerization initiator is not particularly limited, and from the viewpoint of the efficiency of forming the protective layer, it is preferably 0.1 to 5.0% by mass in 100% by mass of the composition for protective layer (2).
  • the composition for protective layer (2) may further contain an ultraviolet absorber, if necessary.
  • the ultraviolet absorber is not particularly limited, and examples thereof include hydroxyphenyl triazine compounds such as 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-s-triazine, 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-s-triazine, 2-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-4,6-diviphenyl-s-triazine, and 2-[[2-hydroxy-4-[1-(2-ethylhexyloxycarbonyl)ethyloxy]phenyl]]-4,6-diphenyl-s-triazine; and benzotriazole compounds such as 2-(5-chloro-2H-benzotriazol-2-yl)-6-tert-butyl-4-methylphenol and 2-(
  • the ultraviolet absorber contained in the composition for protective layer (2) can contribute to improving the weather resistance of the protective layer.
  • the content of the ultraviolet absorber is not particularly limited, and from the viewpoint of weather resistance, etc., it is preferably 0.1 to 1.0 mass% in 100 mass% of the composition for protective layer (2).
  • the protective layer composition (2) can be prepared by mixing the various components described above simultaneously or sequentially in any order.
  • the protective layer (2) can be formed on the surface of the photochromic layer (2) by applying the protective layer composition (2) onto the surface of the photochromic layer and curing the applied protective layer composition (2). If necessary, a primer layer or the like may be further formed between the photochromic layer (2) and the protective layer (2) in order to improve adhesion between the photochromic layer (2) and the protective layer (2).
  • the coating method is not particularly limited, and known coating methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of coating.
  • the curing treatment is not particularly limited, and examples thereof include light irradiation, heat treatment, and the like. These may be used alone or in combination of two or more.
  • the curing treatment conditions can be determined depending on the types of various components contained in the composition for protective layer (2) and the composition of the composition for protective layer (2).
  • an annealing treatment heat treatment
  • the conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.
  • a plastic lens (2) according to one embodiment of the present disclosure can have a layer structure of "photochromic layer/protective layer.”
  • the layer structure "/" is used to encompass both a form in which the layers are in direct contact without any other layer intervening, and a form in which the layers are provided via one or more other layers.
  • the optical article can have a layer structure of "photochromic layer/protective layer/other cured coating layer.”
  • the other cured coating layer is not particularly limited, but examples include a cured layer generally referred to as a hard coat layer. These may be used alone, or two or more types may be used.
  • Providing a hard coat layer in addition to the protective layer can further enhance the durability of the optical article.
  • providing a hard coat layer can also enhance the impact resistance of the optical article.
  • the other cured coating layer can be in direct contact with the protective layer without any other layer intervening.
  • the hard coat layer can be formed by irradiating and/or heating a polymerizable composition for forming a hard coat layer (hereinafter, sometimes simply referred to as a "hard coat layer composition").
  • the hard coat layer is not particularly limited, and examples thereof include an organosilicon-based cured coating layer.
  • An organosilicon-based cured coating layer is generally preferred because it has excellent impact resistance.
  • an antireflection layer is further provided as one embodiment, an organosilicon-based cured coating layer is generally preferred because it has excellent adhesion to the antireflection layer.
  • the organosilicon-based cured coating layer is a cured coating layer obtained by curing a composition for hard coat layer containing an organosilicon compound.
  • the organosilicon compound is not particularly limited and examples thereof include organosilicon compounds that can generate silanol groups by polymerization treatment, such as ⁇ -glycidoxypropyltrimethoxysilane; organopolysiloxanes such as water-dispersed colloidal silica having reactive groups such as halogen atoms or amino groups that undergo condensation reaction with silanol groups; silane coupling agents having a polymerizable group such as a vinyl group, allyl group, (meth)acryloyl group, or (meth)acryloyloxy group, and a hydrolyzable group such as an alkoxy group; etc.
  • the hard coat layer composition containing an organosilicon compound may further contain silicon oxide; particles of an inorganic substance such as titanium oxide; etc., as necessary, for adjusting the refractive index, etc.
  • the hard coat layer composition containing an organosilicon compound may further contain, as necessary, a curing agent such as aluminum acetylacetonate to improve the hardness of the hard coat layer; a surfactant such as a silicone surfactant to control liquid dispersibility and interfacial tension; etc.
  • a curing agent such as aluminum acetylacetonate to improve the hardness of the hard coat layer
  • a surfactant such as a silicone surfactant to control liquid dispersibility and interfacial tension
  • known techniques related to organosilicon-based cured coating layers that can function as hard coat layers can be applied.
  • the polymerizable composition containing an organosilicon compound can be cured by proceeding with a polymerization reaction through light irradiation and/or heat treatment, depending on the types of
  • the hard coat layer composition may or may not contain a solvent. If a solvent is contained, there are no particular restrictions on the solvent that can be used, and any solvent can be used in any amount as long as it does not inhibit the polymerization reaction of the polymerizable composition.
  • the surface of the protective layer When providing the other cured coating layer on the protective layer, there are no particular restrictions, but from the perspective of preventing foreign matter from becoming interposed between the protective layer and the other cured coating layer, it is preferable to subject the surface of the protective layer to a solvent wiping treatment. However, if the protective layer has poor solvent resistance, the solvent wiping treatment may damage the protective layer (e.g., cause surface roughness), which may cause clouding or optical defects in the plastic lens including the protective layer. In contrast, the protective layer (2) formed from the protective layer composition (2) described above exhibits excellent solvent resistance, and is therefore suitable for providing the other cured coating layer on the protective layer (2).
  • the wiping treatment with a solvent is not particularly limited and can be carried out by known methods, such as wiping the surface of the protective layer with a cloth soaked in the solvent.
  • the solvent is not particularly limited and examples include ketone solvents such as acetone; alcohol solvents such as ethanol and isopropyl alcohol; and the like. These may be used alone or in combination of two or more.
  • the protective layer preferably has high resistance to ketone solvents, which are commonly used as wiping solvents during the production of optical articles.
  • the plastic lens (2) may or may not further include other functional layers in addition to the above-mentioned primer layer, photochromic layer, protective layer, and hard coat layer, as necessary.
  • the other functional layer is not particularly limited and examples thereof include an antireflection layer, a water-repellent or hydrophilic antifouling layer, an antifogging layer, etc. These may be used alone or in combination of two or more.
  • the total thickness of the cured coating layers (excluding the hard coat layer) provided on the plastic lens (2), but it is preferably 1 to 110 ⁇ m, more preferably 5 to 100 ⁇ m, and particularly preferably 10 to 95 ⁇ m. If the thickness is at or above the lower limit of the above range, it becomes easier to maintain weather resistance and adhesion, and if it is at or below the upper limit of the above range, it becomes easier to maintain the transmittance (transparency) of the cured coating layer.
  • a coating material means a material that suppresses the incidence of light in at least a part of a specific wavelength range
  • the specific wavelength range means a wavelength range to which a polymerizable composition for forming a photochromic layer, which is used to constitute a plastic lens, is sensitive.
  • the coating material provided on the plastic lens (2) will be described in more detail below.
  • coating material (2) can be a coating material with a transmittance of 15% or less for light with a wavelength of 365 nm when the polymerizable composition for forming the photochromic layer is sensitive to light in the wavelength range of 280 to 380 nm (hereinafter, sometimes simply referred to as "coating material (2)").
  • the transmittance of the coating material (2) for light with a wavelength of 365 nm is not particularly limited as long as it is 15% or less, but from the perspective of preventing light from entering through the edge surface of the lens substrate and making it less likely for arc-shaped color unevenness to occur in the peripheral portion of the plastic lens, it is preferably 10% or less, more preferably 5% or less, and especially preferably 0%.
  • the thickness of the covering material (2) is preferably 5 to 150 ⁇ m, more preferably 10 to 100 ⁇ m, and especially preferably 15 to 50 ⁇ m. If the thickness is above the lower limit of the above range, light incidence from the edge surface will be more likely to be blocked, while if the thickness is below the upper limit of the above range, a good appearance will be more likely to be maintained.
  • the coating material (2) are not particularly limited as long as they have a transmittance of 15% or less for light with a wavelength of 365 nm, and include, for example, adhesive tape, ink, resin film, rubber, and a cured coating layer formed by curing a polymerizable composition. These may be used alone or in combination of two or more types. Of these, adhesive tape and ink are preferred from the perspective of ease of coating.
  • the coating material (2) there are no particular restrictions on the coating material (2) as long as it covers the edge surface of the lens substrate, and the edge surface of the lens substrate may be coated with one layer or two or more layers.
  • covering material (2) Commercially available products for the covering material (2) are not particularly limited, and examples include UNI Posca Black (manufactured by Mitsubishi Pencil Co., Ltd.), UNI Posca White (manufactured by Mitsubishi Pencil Co., Ltd.), Macky Black (manufactured by Zebra Corporation), and Polyimide Tape (manufactured by AS ONE Corporation). These may be used alone or in combination of two or more.
  • the coating material (2) is applied, and it may be at the very beginning of the production of the plastic lens (2), during production (for example, before or after the formation of a primer layer, before or after the formation of a photochromic layer, etc.), or after the production of the plastic lens (2).
  • the eyeglasses can, for example, exhibit an anti-glare effect like sunglasses outdoors by a photochromic compound contained in a photochromic layer that changes color when irradiated with sunlight, and when the eyeglasses return indoors, the photochromic compound fades, allowing the eyeglasses to regain their transparency.
  • the configuration of the eyeglasses' frame is not particularly limited and known techniques can be applied, and may be a full-rim frame that surrounds the entire plastic lens, a half-rim (nylor) frame that surrounds only the upper half of the plastic lens, an under-rim (reverse nylor) frame that surrounds only the lower half of the plastic lens, or a rimless (rimless) frame with only plastic lenses.
  • a half-rim (nylor), under-rim (reverse nylor), and rimless (rimless) are preferred, and rimless (rimless) is more preferred.
  • Coating material 1 UNI Posca Black (manufactured by Mitsubishi Pencil Co., Ltd.): 0% transmittance for light in the wavelength range of 280 to 450 nm, 0% transmittance for light with a wavelength of 365 nm
  • Coating material 2 Polyimide tape (manufactured by AS ONE Corporation): Maximum transmittance of 2% for light in the wavelength range of 280 to 450 nm (wavelength at which maximum transmittance is shown: 450 nm), 0% for light with a wavelength of 365 nm
  • Coating material 3 UNI Posca White (manufactured by Mitsubishi Pencil Co., Ltd.): Maximum transmittance of 16% for light in the wavelength range of 280 to 450 nm (wavelength at which maximum transmittance is shown: 450 nm), 0% for light with
  • Lens substrate 1 Hilux 1.5 (manufactured by HOYA Corporation, central thickness 2.1 mm, peripheral thickness 2.1 mm, refractive index 1.50, maximum transmittance of 93% for light in the wavelength range of 280 to 780 nm (wavelength at which maximum transmittance is shown: 717 nm), transmittance of 34% for light with a wavelength of 365 nm)
  • Lens substrate 2 Hilux 1.6 (manufactured by HOYA Corporation, central thickness 2.0 mm, peripheral thickness 2.0 mm, refractive index 1.60, maximum transmittance of 90% for light in the wavelength range of 280 to 780 nm (wavelength at which maximum transmittance is shown: 773 nm), transmittance of light with a wavelength of 365 nm is 0%)
  • Lens substrate 3 Hilux 1.67 (manufactured by HOYA Corporation, central thickness 2.1 mm, peripheral thickness 2.1 mm, refractive index 1.50, maximum transmittance of 93% for light in the wavelength range of 280
  • Transmittance in this disclosure and this specification refers to a value measured using a spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation) by placing (dying) a lens substrate or a coating material on a glass substrate (Monitor Glass 70 PHI, manufactured by Senyo Optics Co., Ltd.) and transmitting light for each wavelength.
  • a spectrophotometer UH4150, manufactured by Hitachi High-Tech Corporation
  • Primer layer composition 1 TR-SC-P (manufactured by Tokuyama Corporation)
  • Primer layer composition 2 NJ321A (manufactured by Tokuyama Corporation)
  • composition 1 for photochromic layer which is composition (1) for photochromic layer, was obtained.
  • a photoradical polymerization initiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin B.V., Omnirad 819
  • an antioxidant ethylene bis(oxyethylene)bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate)
  • a light stabilizer a mixture of bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate and methyl(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate
  • a photochromic layer composition 2 which is a photochromic layer composition (2), was obtained.
  • the contents of the various components were as follows, relative to 100% by mass of the composition 2 for photochromic layer: 92.0% by mass of the mixture of polymerizable compounds, 5.4% by mass of the photochromic compound, 0.8% by mass of the photoradical polymerization initiator, 0.9% by mass of the antioxidant, and 0.9% by mass of the light stabilizer.
  • primer layer composition 3 In a plastic container, 10.0 parts by mass of a hydroxy group-containing bifunctional acrylate having a compound represented by the following structural formula (1), 15.0 parts by mass of a polyisocyanate (Coronate 2715, manufactured by Tosoh Corporation), and 75.0 parts by mass of 2-phenoxyethyl acrylate (viscosity: 13 cP) were mixed.
  • a polyisocyanate Coronate 2715, manufactured by Tosoh Corporation
  • 2-phenoxyethyl acrylate viscosity: 13 cP
  • a photoradical polymerization initiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin B.V., Omnirad 81
  • a silicone surfactant Polyflow KL-402, manufactured by Kyoeisha Chemical Co., Ltd.
  • a plastic container 94.9 parts by mass of an alicyclic bifunctional (meth)acrylate (tricyclodecane dimethanol diacrylate), 4.7 parts by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.), 0.3 parts by mass of an ultraviolet absorber (Tinuvin 479, manufactured by BASF Japan), and 0.1 parts by mass of a silicone surfactant (DOWSIL FZ-2104, manufactured by Dow-Toray Industries, Inc.) were mixed and thoroughly stirred, and then degassed using a rotation-revolution type stirring and degassing apparatus.
  • a photoradical polymerization initiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.
  • an ultraviolet absorber Tinuvin 479, manufactured by BASF Japan
  • DOWSIL FZ-2104 silicone surfact
  • composition 1 for protective layer which is composition (2) for protective layer
  • the (meth)acrylate is only an alicyclic bifunctional (meth)acrylate, and therefore the content of the alicyclic bifunctional (meth)acrylate is 100% by mass out of 100% by mass of all (meth)acrylates.
  • hard coat layer composition 1 17.00 parts by mass of ⁇ -glycidoxypropyltrimethoxysilane, 30.00 parts by mass of methanol, and 28.00 parts by mass of water-dispersed colloidal silica (solid content 40% by mass, average particle size 15 nm, manufactured by JGC Catalysts and Chemicals Co., Ltd., OPTOLAKE SL-50A) were added to a glass container equipped with a magnetic stirrer, thoroughly mixed, and stirred for 24 hours at 5° C.
  • composition 1 for hard coat layer 15.00 parts by mass of propylene glycol monomethyl ether, 0.05 parts by mass of a silicone surfactant (manufactured by Dow Toray Industries, Inc., DOWSIL FZ-2104), and 1.50 parts by mass of aluminum acetylacetonate as a curing agent were added, thoroughly stirred, and then filtered to prepare composition 1 for hard coat layer.
  • a silicone surfactant manufactured by Dow Toray Industries, Inc., DOWSIL FZ-2104
  • Example 1 Lens substrate 1 was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature: 60° C.) for 5 minutes, then washed with pure water and dried. Primer layer composition 1 was then applied to the convex surface (object-side surface) of the lens substrate by spin coating in an environment of 25°C and 50% relative humidity, and then dried at room temperature for 15 minutes. The formed primer layer had a thickness of 4 ⁇ m. Photochromic layer composition 1 was applied onto the primer layer by spin coating. Spin coating was performed according to the method described in JP 2005-218994 A.
  • the photochromic layer composition 1 applied onto the primer layer was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 220 mW/cm 2 , light irradiation time: 65 seconds, light irradiation exposure amount: 14.3 J/cm 2 ) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature to cure the composition, and then heat-treated in a heat treatment device (PH series, manufactured by Espec Corporation) at an atmospheric temperature of 100°C for 1 hour to form a photochromic layer.
  • the thickness of the formed photochromic layer was 40 ⁇ m.
  • the edge surface of the lens substrate was dyed (coated) with Coating Material 1 (thickness of coating material: 30 ⁇ m).
  • the "thickness of the cured coating layer” is a value calculated by measuring the reflectance (interference waveform) of a sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.) and analyzing the film thickness value using FFT (fast Fourier transform).
  • the "intensity of light irradiation” is a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm).
  • the "exposure amount of light irradiation” is a value calculated from the light irradiation intensity (mW/cm 2 ) ⁇ irradiation time (seconds). In this way, the plastic lens of Example 1 was obtained.
  • Example 2 A plastic lens of Example 2 was obtained in the same manner as in Example 1, except that no primer layer was formed.
  • Example 3 A plastic lens of Example 3 was obtained in the same manner as in Example 1, except that primer layer composition 2 was used instead of primer layer composition 1 in Example 1.
  • Example 4 A plastic lens of Example 4 was obtained in the same manner as in Example 1, except that lens substrate 2 was used instead of lens substrate 1 in Example 1.
  • Example 5 A plastic lens of Example 5 was obtained in the same manner as in Example 1, except that Lens Substrate 3 was used instead of Lens Substrate 1 in Example 1.
  • Example 6 A plastic lens of Example 6 was obtained in the same manner as in Example 1, except that Covering Material 2 was used instead of Covering Material 1 in Example 1 and the edge surface of the lens substrate was covered with polyimide tape.
  • Example 7 A plastic lens of Example 7 was obtained in the same manner as in Example 1, except that Coating Material 3 was used instead of Coating Material 1 in Example 1.
  • Example 8 A plastic lens of Example 8 was obtained in the same manner as in Example 1, except that Coating Material 4 was used instead of Coating Material 1 in Example 1.
  • Comparative Example 1 A plastic lens of Comparative Example 1 was obtained in the same manner as in Example 1, except that no coating material was used.
  • Comparative Example 2 A plastic lens of Comparative Example 2 was obtained in the same manner as in Comparative Example 1, except that Lens Substrate 2 was used instead of Lens Substrate 1 in Comparative Example 1.
  • Example 9 Lens substrate 1 was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature: 60° C.) for 5 minutes, then washed with pure water and dried. Thereafter, primer layer composition 3 was applied to the convex surface (object-side surface) of the lens substrate by spin coating in an environment of 25°C temperature and 50% relative humidity, and then primer layer composition 1 applied to the lens substrate was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW/ cm2 , light irradiation time: 5 seconds, light irradiation exposure amount: 1.25 J/cm2) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less ) at room temperature to cure this composition and form a primer layer.
  • light light wavelength: 405 nm, light irradiation intensity: 250 mW/ cm2 , light irradiation time: 5 seconds, light irradiation exposure amount: 1.25 J/cm2
  • the formed primer layer had a thickness of 8 ⁇ m.
  • Photochromic layer composition 2 was applied onto the primer layer by spin coating. Spin coating was performed according to the method described in JP 2005-218994 A. Thereafter, the photochromic layer composition 1 applied onto the primer layer was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW/cm 2 , light irradiation time: 40 seconds, light irradiation exposure amount: 10 J/cm 2 ) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature to cure the composition and form a photochromic layer. The thickness of the formed photochromic layer was 40 ⁇ m.
  • protective layer composition 1 was applied by spin coating in an environment of 25°C and 50% relative humidity to form a coating layer.
  • the surface of this coating layer was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW/ cm2 , light irradiation time: 15 seconds, light irradiation exposure amount: 3.75 J/ cm2 ) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature to harden the coating layer and form a protective layer.
  • the thickness of the formed protective layer was 38 ⁇ m.
  • the surface of the protective layer was wiped with acetone, and then the hard coat layer composition 1 was applied by dip coating (withdrawal speed: 20 cm/min), and the hard coat layer was subjected to heat treatment at an atmospheric temperature of 100°C for 1 hour using a heat treatment device (PH series, manufactured by Espec Corporation), to form a hard coat layer.
  • the thickness of the formed hard coat layer was 3 ⁇ m.
  • the edge surface of the lens substrate was dyed (coated) with Coating Material 1 (thickness of coating material: 35 ⁇ m).
  • the "thickness of the cured coating layer” is a value calculated by measuring the reflectance (interference waveform) of a sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.) and analyzing the film thickness value using FFT (fast Fourier transform).
  • the "intensity of light irradiation” is a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm).
  • the "exposure amount of light irradiation” is a value calculated from the light irradiation intensity (mW/cm 2 ) ⁇ irradiation time (seconds). In this way, the plastic lens of Example 9 was obtained.
  • Example 10 A plastic lens of Example 10 was obtained in the same manner as in Example 9, except that no primer layer was formed.
  • Example 11 A plastic lens of Example 11 was obtained in the same manner as in Example 9, except that primer layer composition 1 was used instead of primer layer composition 3, photochromic layer composition 3 was used instead of photochromic layer composition 2, and no protective layer was formed.
  • Primer layer composition 1 was dried and cured at room temperature for 15 minutes. The resulting primer layer had a thickness of 4 ⁇ m.
  • Photochromic layer composition 3 was cured by light irradiation (light wavelength: 405 nm, light irradiation intensity: 230 mW/cm 2 , light irradiation time: 60 seconds, light irradiation exposure dose: 13.8 J/cm 2 ).
  • the resulting photochromic layer had a thickness of 40 ⁇ m.
  • Example 12 A plastic lens of Example 12 was obtained in the same manner as in Example 11, except that primer layer composition 2 was used instead of primer layer composition 1.
  • Example 13 A plastic lens of Example 13 was obtained in the same manner as in Example 9, except that Covering Material 2 was used instead of Covering Material 1 in Example 9, and the edge surface of the lens substrate was covered with polyimide tape.
  • Example 14 A plastic lens of Example 14 was obtained in the same manner as in Example 9, except that Coating Material 3 was used instead of Coating Material 1 in Example 9.
  • Example 15 A plastic lens of Example 15 was obtained in the same manner as in Example 9, except that Coating Material 4 was used instead of Coating Material 1 in Example 9.
  • Comparative Example 3 A plastic lens of Comparative Example 3 was obtained in the same manner as in Example 9, except that no covering material was used.
  • Comparative Example 4 A plastic lens of Comparative Example 4 was obtained in the same manner as in Example 11, except that no covering material was used.
  • This disclosure is useful in the technical fields of eyeglasses, goggles, etc.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Eyeglasses (AREA)

Abstract

L'invention concerne : une lentille en plastique ayant un matériau de base de lentille, une couche photochromique qui est formée sur une surface du matériau de base de lentille et est obtenue par durcissement d'une composition polymérisable pour former une couche photochromique sensible à la lumière dans une région de longueur d'onde spécifique, et un matériau de revêtement qui recouvre une surface de bord du matériau de base de lentille et empêche la lumière, qui se trouve à l'intérieur d'au moins une région partielle de la région de longueur d'onde spécifique, d'entrer dans le matériau de base de lentille ; et des lunettes.
PCT/JP2025/008433 2024-03-28 2025-03-07 Lentille en plastique et lunettes Pending WO2025204747A1 (fr)

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JP2013246347A (ja) * 2012-05-28 2013-12-09 Hoya Corp 眼鏡レンズの製造方法
JP2018097173A (ja) * 2016-12-14 2018-06-21 株式会社トクヤマ フォトクロミック光学物品
CN209946569U (zh) * 2019-07-03 2020-01-14 丹阳市宏鑫光学眼镜有限公司 一种变色镜片
JP2021500607A (ja) * 2017-10-19 2021-01-07 エシロール・アンテルナシオナル 光学レンズ

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Publication number Priority date Publication date Assignee Title
WO2008093613A1 (fr) * 2007-02-02 2008-08-07 Tokuyama Corporation Procédé de fabrication d'une lentille ayant une couche revêtue
JP2013246347A (ja) * 2012-05-28 2013-12-09 Hoya Corp 眼鏡レンズの製造方法
JP2018097173A (ja) * 2016-12-14 2018-06-21 株式会社トクヤマ フォトクロミック光学物品
JP2021500607A (ja) * 2017-10-19 2021-01-07 エシロール・アンテルナシオナル 光学レンズ
CN209946569U (zh) * 2019-07-03 2020-01-14 丹阳市宏鑫光学眼镜有限公司 一种变色镜片

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