WO2024185580A1 - 積層体、光学物品、コート層含有積層体、レンズ、眼鏡、及び窓用フィルム - Google Patents

積層体、光学物品、コート層含有積層体、レンズ、眼鏡、及び窓用フィルム Download PDF

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Publication number
WO2024185580A1
WO2024185580A1 PCT/JP2024/007017 JP2024007017W WO2024185580A1 WO 2024185580 A1 WO2024185580 A1 WO 2024185580A1 JP 2024007017 W JP2024007017 W JP 2024007017W WO 2024185580 A1 WO2024185580 A1 WO 2024185580A1
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Prior art keywords
group
resin
laminate
optical substrate
prepolymer
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PCT/JP2024/007017
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English (en)
French (fr)
Japanese (ja)
Inventor
康智 清水
孝洋 川島
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Tokuyama Corp
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Tokuyama Corp
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Priority to CN202480015701.4A priority Critical patent/CN120813870A/zh
Priority to JP2025505243A priority patent/JPWO2024185580A1/ja
Priority to EP24766951.8A priority patent/EP4679147A1/en
Publication of WO2024185580A1 publication Critical patent/WO2024185580A1/ja
Anticipated expiration legal-status Critical
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    • 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
    • G02C7/102—Photochromic filters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B23/00—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose
    • B32B23/04—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B23/08—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1545—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J129/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Adhesives based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Adhesives based on derivatives of such polymers
    • C09J129/02—Homopolymers or copolymers of unsaturated alcohols
    • C09J129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to laminates, optical articles, coated layer-containing laminates, lenses, eyeglasses, and window films.
  • Plastic eyeglasses are eyeglasses that use plastic lenses.
  • Plastic lenses are manufactured, for example, by subjecting semi-finished lenses, which are semi-finished products, to various processes.
  • the convex front surface of a semi-finished lens is provided with functional layers such as a hard coat layer and an anti-reflective film.
  • the concave back surface of a semi-finished lens is also subjected to cutting and polishing.
  • Photochromic lenses which have photochromic properties that change color depending on the amount of UV light, have been attracting attention.
  • Photochromic lenses are obtained by applying a photochromic compound to a plastic lens.
  • a photochromic compound is a compound that can reversibly generate two or more isomers with different light absorption spectra when exposed to light.
  • methods for manufacturing photochromic lenses have included the kneading method, in which a photochromic compound is dispersed in the matrix of a semi-finished lens, and the lamination method, in which a layer containing a photochromic compound is formed on the surface of a semi-finished lens.
  • the binder sheet method is a method for manufacturing semi-finished lenses by integrating a binder sheet, which is a resin layer containing a photochromic compound sandwiched between two optical sheets, with a lens substrate.
  • a semi-finished lens is obtained by mounting a binder sheet in a mold and injecting a thermoplastic resin toward it.
  • semi-finished lenses can be manufactured using free-standing articles containing a photochromic compound, which tends to increase production efficiency and facilitate mass production compared to the kneading method and lamination method.
  • JP 2013-033131 A International Publication No. 2019/163728 International Publication No. 2017/154901 U.S. Pat. No. 1,175,4860
  • the object of the present invention is to provide a laminate having excellent durability of functional dyes, and a coated layer-containing laminate, optical article, lens, eyeglasses, and window film that includes this laminate.
  • a laminate comprising a first optical substrate, a second optical substrate, a functional layer, a first adhesive layer, and a second adhesive layer.
  • the first optical substrate has a first main surface and a second main surface.
  • the second optical substrate has a first main surface and a second main surface.
  • the functional layer is located between the first optical substrate and the second optical substrate.
  • the functional layer includes a resin and a functional dye.
  • the first adhesive layer bonds the first optical substrate and the functional layer.
  • the second adhesive layer bonds the second optical substrate and the functional layer.
  • At least one of the first adhesive layer and the second adhesive layer includes at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins.
  • a coated layer-containing laminate includes a laminate according to an embodiment and a coated layer.
  • the coated layer covers at least a portion of the first optical substrate and the second optical substrate.
  • the coated layer includes at least one resin selected from the group consisting of an epoxy resin, an oxetane resin, an acrylic resin, a methacrylic resin, and a urethane resin.
  • an optical article includes a laminate or a coated layer-containing laminate according to an embodiment.
  • a lens is provided.
  • the lens includes an optical article according to an embodiment.
  • eyeglasses are provided.
  • the eyeglasses include lenses according to other embodiments.
  • the present invention provides a laminate of functional dyes with excellent durability, and a coated layer-containing laminate, optical article, lens, eyeglasses, and window film that includes this laminate.
  • FIG. 1 is a cross-sectional view illustrating an example of a laminate according to an embodiment.
  • FIG. 1 is a cross-sectional view illustrating an example of a coating layer-containing laminate according to an embodiment.
  • FIG. 1 is a cross-sectional view illustrating an example of an optical article according to an embodiment.
  • FIG. 1 is a perspective view illustrating an example of glasses according to an embodiment.
  • a laminate includes a first optical substrate, a second optical substrate, a functional layer, a first adhesive layer, and a second adhesive layer.
  • the first optical substrate has a first main surface and a second main surface.
  • the second optical substrate has a first main surface and a second main surface.
  • the functional layer is located between the first optical substrate and the second optical substrate.
  • the functional layer includes a resin and a functional dye.
  • the first adhesive layer bonds the first optical substrate and the functional layer.
  • the second adhesive layer bonds the second optical substrate and the functional layer.
  • At least one of the first adhesive layer and the second adhesive layer includes at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins.
  • the laminate according to the embodiment is used, for example, as the binder sheet described above.
  • Such a laminate may require durability of the functional dye.
  • the functional dye such as a photochromic compound includes a compound that undergoes a structural change due to energy such as light, and develops, loses, or changes color. When the functional dye is oxidized by oxygen or the like, this structural change is less likely to occur, and the functionality may decrease.
  • at least one of the first adhesive layer and the second adhesive layer contains at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins. This polyvinyl resin functions as an adhesive and is also thought to function as a barrier layer that suppresses oxygen transmission. Therefore, the functional dye contained in the functional layer that contacts such an adhesive layer is less likely to deteriorate. Therefore, according to the embodiment, a laminate with excellent durability of the functional dye can be realized.
  • the laminate according to the embodiment can be used as a binder sheet.
  • the laminate according to the embodiment can be used as a functional sheet in which a functional dye such as a photochromic compound is blended in a functional layer.
  • the thickness of the laminate according to the embodiment is preferably 100 ⁇ m or more, more preferably 120 ⁇ m or more, and even more preferably 150 ⁇ m or more.
  • shape stability tends to be improved.
  • There is no particular upper limit to the thickness of the laminate but in one example it is 1000 ⁇ m or less, and in another example it is 500 ⁇ m or less, and more preferably 400 ⁇ m or less.
  • a thin thickness improves handleability even when manufacturing eyeglass lenses with a thin center thickness.
  • FIG. 1 is a cross-sectional view showing an example of a laminate according to an embodiment.
  • the laminate 1 shown in FIG. 1 includes a first optical substrate 2, a second optical substrate 3, a functional layer 4 interposed therebetween, a first adhesive layer FA located between the functional layer 4 and the first optical substrate 2, and a second adhesive layer SA between the functional layer 4 and the second optical substrate 3.
  • the first optical substrate 2 includes a first main surface 2a and a second main surface 2b.
  • the first main surface 2a constitutes one of the outermost surfaces of the laminate 1.
  • the second main surface 2b is in contact with the first adhesive layer FA.
  • the second optical substrate 3 includes a first main surface 3a and a second main surface 3b.
  • the first main surface 3a constitutes the other outermost surface of the laminate 1.
  • the second main surface 3b is in contact with the second adhesive layer SA.
  • the first and second optical substrates may be optical films or sheets having visible light transmissibility.
  • the first and second optical substrates may be colorless transparent films, semi-transparent films, or colored transparent films.
  • the thickness of the first and second optical substrates is, for example, 10 ⁇ m or more and 100 ⁇ m or less, and preferably 20 ⁇ m or more and 80 ⁇ m or less.
  • the thickness of the second optical substrate may be the same as or different from the thickness of the first optical substrate.
  • the first and second optical substrates are preferably resin films or resin sheets.
  • the resin may be at least one resin selected from the group consisting of cellulose resin, acrylic resin, methacrylic resin, polyurethane resin, polyurethane urea resin, polyamide resin, polyester resin, polyimide resin, epoxy resin, polyolefin resin, polyvinyl alcohol resin, and polycarbonate resin.
  • At least one of the first optical substrate and the second optical substrate is made of saponified triacetyl cellulose resin.
  • the contact angle of pure water in the saponified portion of the optical substrate is, for example, 60° or less.
  • a low contact angle tends to increase adhesion at the interface between the optical substrate and other members.
  • the contact angle is preferably 50° or less, more preferably 30° or less, and even more preferably 15° or less.
  • the lower limit of the contact angle is, for example, 5°, and in another example, 10°.
  • the contact angle can be measured, for example, using a DropMaster 500 manufactured by Kyowa Interface Science Co., Ltd.
  • a TAC film in which at least a portion of the first and second main surfaces has been saponified can be used.
  • the optical substrate it is preferable that at least one of the first and second main surfaces is a TAC film in which the entire surface has been saponified, and it is more preferable that both surfaces are a TAC film in which the entire surface has been saponified.
  • both the first and second optical substrates are saponified TAC films, but one of them may be a TAC film that has not been saponified, or it may be a resin film other than TAC resin.
  • cellulose resins examples include diacetyl cellulose, tripropyl cellulose, and dipropyl cellulose.
  • Polyamide resins that can be used include polyamide resins obtained by polycondensation of ⁇ -aminocarboxylic acids such as ⁇ -caprolactam, 10-aminodecanoic acid lactam, and ⁇ -laurinlactam, polyamide resins obtained by co-condensation of diamines and dicarboxylic acids, and copolymers thereof.
  • polyamide resins obtained by co-condensation alicyclic polyamide resins or semi-aromatic polyamide resins are preferred.
  • polyester resins include polycondensates of dicarboxylic acids such as terephthalic acid and isophthalic acid with diols such as ethylene glycol, butylene glycol, and 1,4-cyclohexanedimethanol.
  • the (meth)acrylic resin can be, for example, a homopolymer such as methyl methacrylate, or a resin made of a copolymer of multiple (meth)acrylic monomers.
  • polyurethane resin and polyurethane urea resin known resins obtained by reacting a diisocyanate compound such as isophorone diisocyanate with a polyol compound such as polycarbonate polyol or polyester polyol can be used.
  • polyurethane resins or polyurethane urea resins obtained by reacting a chain extender such as a low molecular weight diol, triol, diamine, or triamine can be preferably used.
  • polyimide resin a polymer of an aromatic tetracarboxylic acid and an aromatic diamine can be used.
  • aromatic tetracarboxylic acids include pyromellitic acid, 3,3',4,4'-biphenyltetracarboxylic acid, 2,3',3,4'-biphenyltetracarboxylic acid, 3,3',4,4'-benzophenonetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)propane, pyridine-2,3,5,6-tetracarboxylic acid, or its acid anhydride, or its acid dianhydride, or aromatic tetracarboxylic acids derived from its acid ester compound or halide.
  • epoxy resins for example, resins obtained by condensation reaction of bisphenol A, bisphenol F, etc. with epichlorohydrin, other multifunctional epoxy resins, biphenyl type epoxy resins, etc. can be suitably used.
  • polystyrene resins for example, polypropylene, polyethylene, ethylene-propylene copolymer, ethylene- ⁇ -olefin copolymer, and propylene- ⁇ -olefin copolymer can be suitably used.
  • the functional layer includes a resin and a functional dye.
  • the resin may be at least one resin selected from the group consisting of a polyurethane resin, a polyurethane urea resin, a polythiourethane resin, and a polythiourethane urea resin.
  • the functional layer may include a cured product of a functional layer-forming composition described below.
  • the thickness of the functional layer is, for example, 0.1 ⁇ m or more and 100 ⁇ m or less.
  • the thickness of the functional layer may be thinner or thicker than the thickness of the first and second optical substrates.
  • composition for forming functional layer may include a functional dye and a polymerizable component.
  • the polymerizable component becomes the matrix of the adhesive layer.
  • the polymerizable component may be a second prepolymer, or a first polymer and a second prepolymer or a first polymer and a second prepolymer.
  • the composition for forming the functional layer includes a first combination of a polymerization component containing only the second prepolymer and a functional dye, and a polymerization component containing the first polymer and the second prepolymer.
  • a second combination with a functional dye a third combination of a polymerization component including the first polymer and a third prepolymer with a functional dye; a polymerization component including the first polymer, the second prepolymer, and the third prepolymer;
  • a fourth combination of components and functional dyes, and a fifth combination of polymerized components and functional dyes that includes only the first polymer, may be included.
  • the functional dye includes, for example, at least one selected from the group consisting of a photochromic compound, an ultraviolet absorbing agent, a blue light absorbing agent, an infrared absorbing agent, a dye, and an electrochromic compound.
  • the photochromic compound for example, at least one selected from the group consisting of chromene compounds, fulgide compounds, and spirooxazine compounds is used.
  • the photochromic compound it is preferable to use a chromene compound.
  • Chromene compounds include compounds having a 1-benzopyran skeleton, spiropyran compounds containing a spiropyran skeleton, and naphthopyran compounds having a naphthopyran skeleton.
  • Naphthopyran compounds include indenonaphthopyran compounds having an indenonaphthopyran skeleton.
  • Chromene compounds preferably include indenonaphthopyran compounds having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton.
  • a cured body containing a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton tends to have excellent durability.
  • the indenonaphthopyran compound preferably includes a compound represented by the following formula (IIIa):
  • the Z ring is a substituted or unsubstituted spiro ring with the carbon atom at position 13 as a spiro atom.
  • the Z ring may form an aliphatic ring together with the carbon atom at position 13, a condensed polycyclic ring, a heterocyclic ring, or a heterocyclic aromatic ring.
  • the Z ring is preferably an aliphatic ring having 5 to 16 ring carbon atoms. It is more preferable that the aliphatic ring has an alkyl group having 1 to 3 carbon atoms as a substituent.
  • R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are each independently a hydrogen atom, a hydroxyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxy group, an amino group, a substituted amino group, a heterocyclic group which may have a substituent, a halogen atom, an alkylthio group, an arylthio group which may have a substituent, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an aralkyl group which may have a substituent, an aralkoxy group which may have a substituent, an aryloxy group which may have a substituent, an aryl group which may have a substituent, an aryl group which
  • the number of carbon atoms in the alkyl group is preferably 1 to 10.
  • alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, and hexyl.
  • the haloalkyl group preferably has 1 to 10 carbon atoms.
  • the haloalkyl group is preferably an alkyl group substituted with a fluorine atom, a chlorine atom, or a bromine atom.
  • suitable haloalkyl groups include a trifluoromethyl group, a tetrafluoroethyl group, a chloromethyl group, a 2-chloroethyl group, and a bromomethyl group.
  • the number of ring carbon atoms of the cycloalkyl group is preferably 3 to 8.
  • Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Note that the cycloalkyl group may have a substituent, but the number of carbon atoms in the substituent is not included in the number of carbon atoms (3 to 8 carbon atoms).
  • the number of carbon atoms in the alkoxy group is preferably 1 to 10, and more preferably 1 to 6.
  • suitable alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, and tert-butoxy groups.
  • the amino group is a primary amino group (-NH 2 ).
  • the substituted amino group is a secondary or tertiary amino group in which one or two hydrogen atoms have been substituted.
  • the substituent on the substituted amino group 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.
  • suitable amino groups include an amino group, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, and a diphenylamino group.
  • the number of atoms in the heterocyclic group is preferably 3 to 10.
  • the heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group.
  • Specific examples of the aliphatic heterocyclic group include a morpholino group, a piperidino group, a pyrrolidinyl group, a piperazino group, and an N-methylpiperazino group.
  • Specific examples of the aromatic heterocyclic group include an indolinyl group.
  • the heterocyclic group may have a substituent.
  • a preferred substituent is an alkyl group having 1 to 10 carbon atoms.
  • Suitable examples of the heterocyclic group having a substituent include a 2,6-dimethylmorpholino group, a 2,6-dimethylpiperidino group, and a 2,2,6,6-tetramethylpiperidino group.
  • Halogen atoms include, for example, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
  • the number of carbon atoms in the alkylthio group is preferably 1 to 10.
  • alkylthio groups include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, and t-butylthio groups.
  • the number of carbon atoms in the arylthio group is preferably 6 to 10.
  • arylthio groups include a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group.
  • the number of carbon atoms in the alkylcarbonyl group is preferably 2 to 10.
  • alkylcarbonyl groups include acetyl and ethylcarbonyl groups.
  • the number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 10.
  • Examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group.
  • the number of carbon atoms in the aralkyl group is preferably 7 to 11.
  • aralkyl groups include benzyl, phenylethyl, phenylpropyl, phenylbutyl, and naphthylmethyl groups.
  • the number of carbon atoms in the aralkoxy group is preferably 7 to 11.
  • Examples of aralkoxy groups include benzyloxy and naphthylmethoxy groups.
  • the number of carbon atoms in the aryl group is preferably 6 to 12.
  • aryl groups include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • the number of carbon atoms in the aryloxy group is preferably 6 to 12.
  • aryloxy groups include a phenyloxy group and a naphthyloxy group.
  • the number of carbon atoms in the heteroaryl group is preferably 3 to 12.
  • heteroaryl groups include a thienyl group, a furyl group, a pyrrolinyl group, a pyridyl group, a benzothienyl group, a benzofuranyl group, and a benzopyrrolinyl group.
  • the number of carbon atoms in the alkoxyalkylthio group is preferably 2 to 10.
  • alkoxyalkylthio groups include a methoxymethylthio group, a methoxyethylthio group, a methoxy n-propylthio group, a methoxy n-butylthio group, an ethoxyethylthio group, and an n-propoxypropylthio group.
  • the haloalkylthio group preferably has 1 to 10 carbon atoms.
  • haloalkylthio groups include a trifluoromethylthio group, a tetrafluoroethylthio group, a chloromethylthio group, a 2-chloroethylthio group, and a bromomethylthio group.
  • the cycloalkylthio group preferably has 3 to 8 carbon atoms.
  • Examples of cycloalkylthio groups include cyclopropylthio, cyclobutylthio, cyclopentylthio, and cyclohexylthio.
  • the cycloalkylthio group may have a substituent, but the number of carbon atoms in the substituent is not included in the number of carbon atoms (3 to 8 carbon atoms).
  • the oligomeric group comprises an oligomeric chain, a linking group, and a terminal group.
  • the oligomer chain may include at least one selected from the group consisting of a polyalkylene oxide chain, a polysiloxane chain, and a polyester chain.
  • the oligomer chain is a divalent group.
  • the polyalkylene oxide chain has a linear or branched polyalkylene oxide repeating unit having from 1 to 10 carbon atoms.
  • the number of repeating units is, for example, from 3 to 1000.
  • Examples of the repeating unit are -CH 2 O-, -CH 2 CH 2 O-, -CH(CH 3 )CH 2 O-, -CH 2 CH(CH 3 ) O- , -CH 2 CH 2 CH 2 O-, or -CH 2 CH 2 C (CH 3 )O-.
  • the polysiloxane chain has, for example, a repeating unit of dimethylsilyleneoxy (-Si(CH 3 ) 2 O-).
  • the number of repeating units is, for example, 3 or more and 1,000 or less.
  • the number of repeating units is, for example, 3 or more and 1000 or less.
  • the linking group bonds the photochromic compound to one end of the oligomer chain.
  • the linking group may be a divalent group or a group having a valence of two or more.
  • the terminal group is bonded to the other end of the oligomer chain.
  • the terminal group is, for example, a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 30 carbon atoms, or an organic residue having 1 to 10 carbon atoms and 1 to 3 oxygen atoms.
  • the terminal group is preferably a methyl group.
  • the oligomer group may include a first linking group, an oligomer chain, and a second linking group.
  • the first linking group and the second linking group may have the same structure or different structures.
  • the first linking group is linked to the first photochromic compound.
  • the second linking group is linked to the second photochromic compound.
  • the first photochromic compound and the second photochromic compound may have the same structure or different structures.
  • cycloalkyl groups, arylthio groups, aralkyl groups, aralkoxy groups, aryloxy groups, aryl groups, heteroaryl groups, and cycloalkylthio groups may be unsubstituted or may have a substituent.
  • the substituents that may be possessed by the cycloalkyl group, arylthio group, aralkyl group, aralkoxy group, aryloxy group, aryl group, heteroaryl group, and cycloalkylthio group may be selected from the group consisting of primary amino group, secondary amino group, tertiary amino group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, hydroxyl group, cycloalkyl group having 3 to 8 carbon atoms, aryl group having 6 to 12 carbon atoms, alkylaryl group having 1 to 20 carbon atoms, heterocycloalkyl group having 1 to 8 carbon atoms and containing 1 to 5 heteroatoms, heteroaryl group having 1 to 8 carbon atoms and containing 1 to
  • R 13 and R 14 , R 14 and R 15 , and R 15 and R 16 may be bonded to each other to form an aliphatic ring having 2 to 5 carbon atoms, an aliphatic heterocycle having 1 to 4 carbon atoms and containing 1 to 3 heteroatoms, an aromatic ring having 4 to 12 carbon atoms, or an aromatic heterocycle having 3 to 11 carbon atoms and containing 1 to 6 heteroatoms.
  • the aliphatic ring, the aliphatic heterocycle, the aromatic ring, and the aromatic heterocycle may be unsubstituted or may have at least one substituent selected from the above-mentioned substituent group.
  • m is an integer between 0 and 4. m may be 1 or more, or 2 or more.
  • the ultraviolet absorber has an absorption wavelength in the ultraviolet (UV) region of 400 nm or less.
  • the ultraviolet absorber may have a maximum absorption wavelength in the region of 330 nm or more and 380 nm or less, or may have a maximum absorption wavelength in the region of 250 nm or more and less than 330 nm.
  • An organic compound may be used as the ultraviolet absorber.
  • at least one selected from the group consisting of benzophenone derivatives, ethylhexyl methoxycinnamate, benzotriazole derivatives, and triazine derivatives is used as the ultraviolet absorber.
  • the ultraviolet absorber contains at least one selected from the group consisting of benzophenone derivatives, ethylhexyl methoxycinnamate, and benzotriazole derivatives.
  • a compound having an absorption peak in the wavelength region of more than 400 nm and not more than 450 nm in the absorption spectrum can be used.
  • a compound is, for example, at least one selected from the group consisting of perylene-based compounds, porphyrin-based compounds, carotenoid-based compounds, and cyanine-based compounds.
  • As the blue light absorbent it is preferable to use a porphyrin-based compound, and it is more preferable to use a tetraazaporphyrin compound.
  • the high-energy visible light absorber is a blue light absorber that has an absorption peak in the wavelength region of 400 nm or more and 420 nm or less.
  • the high-energy visible light absorber may be the same as the blue light absorber.
  • the dye preferably contains a compound having an absorption peak in the wavelength region of 540 nm or more and 650 nm or less in the absorption spectrum, and more preferably contains a compound having an absorption peak in the wavelength region of 550 nm or more and 600 nm or less.
  • a compound having an absorption peak in the wavelength region of 550 nm or more and 600 nm or less enhances the anti-glare properties of the optical article.
  • examples of such compounds include nitro-based compounds, azo-based compounds, anthraquinone-based compounds, threne-based compounds, porphyrin-based compounds, and rare earth metal compounds.
  • electrochemical compounds examples include organic substances such as viologens, electrochemical polymers, and metal salt complexes with d atoms.
  • the proportion of the functional dye in the solid content of the functional layer forming composition is, for example, 0.1% by mass or more and 10% by mass or less, and preferably 1% by mass or more and 5% by mass or less.
  • the second prepolymer is obtained by reacting a first prepolymer obtained by reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound with a second polyfunctional active hydrogen compound which is a chain extender.
  • the second prepolymer has two or more iso(thio)cyanate groups.
  • the second prepolymer preferably has iso(thio)cyanate groups at both ends of the main chain.
  • the second prepolymer includes at least one selected from the group consisting of urethane prepolymer, urea prepolymer, urethane urea prepolymer, thiourethane prepolymer, thiourea prepolymer, and thiourethane urea prepolymer.
  • the second prepolymer forms at least one resin selected from the group consisting of (thio)urethane resin, (thio)urea resin, and (thio)urethane urea resin by polymerization.
  • the number average molecular weight of the second prepolymer is preferably 3,000 or more, more preferably 10,000 or more, and even more preferably 13,000 or more.
  • the peel strength of the laminate tends to increase. In other words, it is believed that second prepolymers with a large number average molecular weight tend to be easily entangled with each other, increasing the cohesive force and therefore the adhesive strength.
  • the number average molecular weight of the second prepolymer is preferably 50,000 or less, more preferably 40,000 or less, and even more preferably 30,000 or less. If the number average molecular weight of the second prepolymer is excessively large, the peel strength of the laminate tends to be reduced. In other words, a second prepolymer with a large number average molecular weight contains a small amount of iso(thio)cyanate groups per unit mass, and therefore tends to have weaker adhesive strength.
  • the number average molecular weight of the second prepolymer can be measured by gel permeation chromatography (GPC). The measurement is performed under the following conditions: two Shodex KD-806M (Showa Denko K.K.) columns connected in series, eluent: LiBr (10 mmol/L)/DMF solution, flow rate: 1 ml/min, detector: RI detector, second prepolymer sample solution: 1.0% dimethylformamide (DMF) solution.
  • the analysis software used is Nihon Waters K.K.'s GPC analysis software "Empower Personal GPC Option.”
  • the softening point of the second prepolymer is preferably 70°C or higher, more preferably 100°C or higher, and even more preferably 110°C or higher. If the softening point of the second prepolymer is high, the heat resistance of the laminate tends to improve and the adhesion tends to be higher. There is no particular upper limit to the softening point of the second prepolymer, but in one example it is 200°C or lower, and in another example it is 160°C or lower.
  • the softening point of the second prepolymer is measured, for example, by the following method.
  • the concentration of the second prepolymer in the solution is, for example, 34% by mass.
  • This solution is poured into a stainless steel container and dried at 40°C for 10 hours, at 60°C for 10 hours, and then at 60°C for 12 hours in a vacuum dryer to prepare a test piece with a thickness of 1 mm.
  • the obtained test piece is analyzed using a thermomechanical measuring device (Seiko Instruments Inc., TMA120C) to obtain the softening point.
  • the measurement conditions are a heating rate of 10°C/min, a measurement temperature range of 30 to 200°C, and a needle probe with a tip diameter of 0.5 mm.
  • the second prepolymer may be the main component of the solid content of the functional layer forming composition.
  • the proportion of the second prepolymer in the solid content of the functional layer forming composition is, for example, 90% by mass or more and 99% by mass or less.
  • the proportion of the second prepolymer in the solid content of the functional layer forming composition is, for example, 5% by mass or more and 50% by mass or less, and preferably 10% by mass or more and 40% by mass or less.
  • the first prepolymer is obtained by reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound.
  • the first prepolymer has two or more iso(thio)cyanate groups.
  • the first prepolymer preferably has iso(thio)cyanate groups at both ends of the main chain.
  • the first prepolymer includes at least one selected from the group consisting of urethane prepolymer, urea prepolymer, thiourethane prepolymer, and thiourea prepolymer.
  • the first prepolymer is a raw material for the second prepolymer.
  • the number average molecular weight of the first prepolymer is preferably 500 or more and 10,000 or less, and more preferably 1,000 or more and 5,000 or less.
  • the number average molecular weight of the first prepolymer can be measured in the same manner as for the second prepolymer.
  • the first iso(thio)cyanate compound has two or more iso(thio)cyanate groups.
  • the first iso(thio)cyanate compound preferably has two iso(thio)cyanate groups. More preferably, the first iso(thio)cyanate compound is a diisocyanate compound containing two isocyanate groups.
  • the molar mass of the first iso(thio)cyanate compound is preferably 100 or more and 500 or less. When a first iso(thio)cyanate compound within this range is used, a second prepolymer and a first polymer having the desired number average molecular weight tend to be obtained.
  • the molar mass of the first iso(thio)cyanate compound is more preferably 150 or more and 300 or less.
  • the first iso(thio)cyanate compound includes at least one selected from the group consisting of an aliphatic iso(thio)cyanate compound, an alicyclic iso(thio)cyanate compound, and an aromatic iso(thio)cyanate compound.
  • the first iso(thio)cyanate compound is preferably an alicyclic iso(thio)cyanate compound.
  • As the first iso(thio)cyanate compound a single type may be used, or multiple types may be mixed and used.
  • aliphatic isocyanate compounds include pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, 2,4,4-trimethylhexanemethylene diisocyanate, and 1,2-bis(2-isocyanatoethylthio)ethane.
  • alicyclic isocyanate compounds include isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate (hydrogenated diphenylmethane diisocyanate), norbornane diisocyanate, 2,5-bis(isocyanatomethyl)-bicyclo[2,2,1]-heptane, and 2,6-bis(isocyanatomethyl)-bicyclo[2,2,1]-heptane.
  • aromatic isocyanate compounds include xylylene diisocyanate (o-, m-, p-), toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 4,4'-diphenylmethane diisocyanate, etc.
  • aliphatic isothiocyanate compounds include hexamethylene diisothiocyanate, 1,2-diisothiocyanate ethane, 1,3-diisothiocyanate propane, 1,4-diisothiocyanate butane, 1,6-diisothiocyanate hexane, 2,4,4-trimethylhexanemethylene diisothiocyanate, thiobis(3-isothiocyanate propane), thiobis(2-isothiocyanate ethane), dithiobis(2-isothiocyanate ethane), etc.
  • alicyclic isothiocyanate compounds include isophorone diisothiocyanate, cyclohexane diisothiocyanate, 2,4-bis(isothiocyanatomethyl)norbornane, 2,5-bis(isothiocyanatomethyl)norbornane, 2,6-bis(isothiocyanatomethyl)norbornane, 3,5-bis(isothiocyanatomethyl)norbornane, and norbornane diisothiocyanate.
  • aromatic isothiocyanate compounds include p-phenylenediisopropylidenediisothiocyanate, 1,2-diisothiocyanate benzene, 1,3-diisothiocyanate benzene, 1,4-diisothiocyanate benzene, 2,4-diisothiocyanate toluene, xylylene diisothiocyanate (o-, m-, p-), 2,4-tolylene diisothiocyanate, 2,6-tolylene diisothiocyanate, 1,1'-methylenebis(4-isothiocyanate benzene), 1,1'-methylenebis(4-isothiocyanate 2-methylbenzene), 1,1'-methylenebis(4-isothiocyanate 3-methylbenzene), etc.
  • the first multifunctional active hydrogen compound has two or more active hydrogen groups.
  • the first multifunctional active hydrogen compound preferably has two active hydrogen groups.
  • the active hydrogen group includes at least one selected from the group consisting of a hydroxyl group, an amino group, a carboxyl group, and a thiol group.
  • the first multifunctional active hydrogen compound includes at least one selected from the group consisting of, for example, a polyol compound containing two or more hydroxyl groups, a polyamine compound containing two or more amino groups, a dicarboxylic acid containing two or more carboxyl groups, and a polythiol compound containing two or more thiol groups.
  • a single type may be used, or a mixture of multiple types may be used.
  • the first polyfunctional active hydrogen compound preferably contains a polyol compound.
  • a polyol compound When a polyol compound is used, a first prepolymer having a (thio)urethane bond is obtained.
  • the repeating structural portion of the polyol compound can contribute to providing a matrix in the adhesive layer that does not easily hinder the structural change of the photochromic compound.
  • the photochromic properties of the laminate tend to be enhanced.
  • the number average molecular weight of the polyol compound is preferably 500 or more and 3000 or less. When a polyol compound having a number average molecular weight within this range is used, a second prepolymer and a first polymer having the desired number average molecular weight tend to be obtained.
  • the number average molecular weight of the polyol compound is more preferably 800 or more and 2000 or less.
  • the polyol compound may contain at least one selected from the group consisting of polyether polyol, polyester polyol, polycarbonate polyol, and polycaprolactone polyol.
  • the polyol compound preferably contains polycarbonate polyol. Use of polycarbonate polyol tends to increase the adhesion of the laminate.
  • Polycarbonate polyols can be obtained, for example, by monophosgenation of low molecular weight polyols or by ester exchange methods using ethylene carbonate, diethyl carbonate, diphenyl carbonate, etc.
  • low molecular weight polyols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 3-methyl-1,5-pentanediol, 2-ethyl-4-butyl-1,3-propanediol, diethylene glycol, dipropylene glycol, neopen
  • Polycarbonate polyols that can be used include the "Duranol (registered trademark)” series manufactured by Asahi Kasei Chemicals Corporation, the “Kuraray Polyol (registered trademark)” series manufactured by Kuraray Co., Ltd., the "Placcel (registered trademark)” series manufactured by Daicel Corporation, the “Nippolan (registered trademark)” series manufactured by Tosoh Corporation, and the “ETERNACOLL (registered trademark)” series manufactured by UBE Co., Ltd.
  • Polycaprolactone polyol can be obtained, for example, by ring-opening polymerization of ⁇ -caprolactone.
  • Examples of polycaprolactone polyol that can be used include the "Placcel (registered trademark)" series manufactured by Daicel Corporation.
  • Polyether polyols can be obtained, for example, by reacting a compound having two or more active hydrogen groups in the molecule with an alkylene oxide.
  • compounds having two or more active hydrogen-containing groups include water, ethylene glycol, propylene glycol, butanediol, glycerin, trimethylolpropane, hexanetriol, triethanolamine, diglycerin, pentaerythritol, trimethylolpropane, and hexanetriol.
  • alkylene oxides include cyclic ether compounds such as ethylene oxide, propylene oxide, and tetrahydrofuran.
  • polyether polyols examples include the “EXENOL (registered trademark)” series and “EMULSTAR (registered trademark)” series manufactured by AGC Inc., and the “ADEKA POLYETHER” series manufactured by ADEKA Corporation.
  • Polyester polyols are obtained, for example, by the condensation reaction of polyhydric alcohols and polybasic acids.
  • polyhydric alcohols include ethylene glycol, 1,2-propanediol, 1,3-butanediol, 1,4-butanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 3,3'-dimethylolheptane, 1,4-cyclohexanedimethanol, neopentyl glycol, 3,3-bis(hydroxymethyl)heptane, diethylene glycol, dipropylene glycol, glycerin, and trimethylolpropane.
  • polybasic acids examples include succinic acid, adipic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclohexanedicarboxylic acid, orthophthalic acid, isophthalic acid, terephthalic acid, and naphthalenedicarboxylic acid.
  • Polyester polyols that can be used include the "Polylite (registered trademark)” series manufactured by DIC Corporation, the “Nippolan (registered trademark)” series manufactured by Tosoh Corporation, and the “Maximol (registered trademark)” series manufactured by Kawasaki Chemical Industries, Ltd.
  • the polythiol compound may include at least one selected from the group consisting of aliphatic polythiols, aromatic polythiols, and polythiols containing sulfur atoms other than mercapto groups.
  • aliphatic polythiols examples include methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, tetrakis(mercaptomethyl)methane, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis(mercaptomethyl)cyclo
  • hexane thiomalic acid bis(2-mercaptoethyl ester), 2,3-dimercaptosuccinic acid (2-mercaptoethyl
  • aromatic polythiols examples include 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,2-bis(mercaptomethoxy)benzene, 1,3-bis(mercaptomethoxy)benzene, 1,4-bis(mercaptomethoxy)benzene, 1,2-bis(mercaptoethoxy)benzene, 1,3-bis(mercaptoethoxy)benzene, 1,4-bis(mercaptoethoxy)benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris
  • polythiols containing sulfur atoms other than mercapto groups include bis(mercaptomethyl)sulfide, bis(mercaptoethyl)sulfide, bis(mercaptopropyl)sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane, 1,2-bis(3-mercapto These include 1,3-bis(mercaptomethylthio)ethane, 1,3-bis(2-mercaptoethylthio)propane, 1,3-bis(3-mercaptopropylthio)propane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol
  • the amount of the first polyfunctional active hydrogen compound is preferably adjusted so that the ratio M11/M12 between the molar amount M11 of the active hydrogen groups contained in the first polyfunctional active hydrogen compound and the molar amount M12 of the iso(thio)cyanate groups contained in the first iso(thio)cyanate compound is 0.30 or more and 0.90 or less.
  • the ratio M11/M12 is within the above range, a sufficient amount of at least one of urethane bonds and urea bonds is formed in the first prepolymer, and a flexible adhesive layer that does not easily inhibit the structural change of the photochromic compound can be formed.
  • the ratio M11/M12 is preferably 0.40 or more and 0.850 or less, and more preferably 0.50 or more and 0.80 or less.
  • the ratio S1/S2 of the mass S1 of the first polyfunctional active hydrogen compound to the mass S2 of the first iso(thio)cyanate compound is preferably 0.1 or more and 10 or less.
  • the ratio S1/S2 is preferably 0.8 or more and 5 or less, and more preferably 1 or more and 4 or less.
  • the second multifunctional active hydrogen compound has two or more active hydrogen groups.
  • the second multifunctional active hydrogen compound reacts with the first prepolymer to produce a second prepolymer.
  • the second multifunctional active hydrogen compound functions as a chain extender that connects the first prepolymers together.
  • the second multifunctional active hydrogen compound preferably has two active hydrogen groups.
  • the compounds listed as the first multifunctional active hydrogen compound can be used.
  • the second polyfunctional active hydrogen compound preferably contains a polyamine.
  • a polyamine When a polyamine is used, a second prepolymer having a (thio)urethane urea bond is obtained. When such a second prepolymer is used, the adhesion of the laminate tends to be increased.
  • the molar mass of the polyamine is preferably 50 or more and 500 or less. When a polyamine having a molar mass within this range is used, a second prepolymer having a desired number average molecular weight tends to be obtained.
  • the molar mass of the polyamine is more preferably 50 or more and 300 or less.
  • the polyamine includes a diamine and a triamine, and preferably contains a diamine.
  • Polyamines include isophoronediamine, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, piperazine, N,N-bis-(2-aminoethyl)piperazine, bis-(4-aminocyclohexyl)methane, bis-(4-amino-3-butylcyclohexyl)methane, 1,2-, 1,3- and 1,4- Examples include diaminocyclohexane, norbornanediamine, hydrazine, dihydrazine adipate, phenylenediamine, 4,4'-diphenylmethanediamine, N,N'-diethylethylenediamine, N,N'-dimethyl
  • the polyamine preferably includes at least one selected from the group consisting of isophoronediamine, ethylenediamine, bis-(4-aminocyclohexyl)methane, and 1,6-diaminohexane.
  • the amount of the second polyfunctional active hydrogen compound is preferably adjusted so that the ratio M13/M14 of the molar amount M13 of the active hydrogen groups contained in the second polyfunctional active hydrogen compound to the molar amount M14 of the iso(thio)cyanate groups contained in the first prepolymer is 0.21 or more and 0.9 or less.
  • the ratio M13/M14 is within the above range, a sufficient amount of the second prepolymer is produced.
  • the ratio S3/S4 of the mass S3 of the second polyfunctional active hydrogen compound to the mass S4 of the first prepolymer is preferably 0.01 or more and 0.5 or less.
  • the ratio S3/S4 is within the above range, a second prepolymer having a sufficient amount of isocyanate groups per unit mass is obtained. It is more preferable that the ratio S3/S4 is 0.05 or more and 0.3 or less.
  • the first polymer is obtained by reacting the second prepolymer with a monofunctional active hydrogen compound having one active hydrogen group.
  • the first polymer typically does not have an iso(thio)cyanate group.
  • the terminal of the first polymer is modified with a non-reactive functional group.
  • the first polymer includes at least one selected from the group consisting of a urethane polymer, a urea polymer, a urethane urea polymer, a thiourethane polymer, a thiourea polymer, and a thiourethane urea polymer.
  • the first polymer chemically bonds with the second prepolymer or the third prepolymer and with hydroxyl groups on the surfaces of the first and second substrates at high temperatures to produce at least one resin selected from the group consisting of (thio)urethane resins, (thio)urea resins, and (thio)urethane urea resins.
  • the number average molecular weight of the first polymer is preferably 5,000 or more, more preferably 10,000 or more, and even more preferably 13,000 or more. When a first polymer with a large number average molecular weight is used, the peel strength of the laminate tends to be increased.
  • the number average molecular weight of the first polymer is preferably 50,000 or less, more preferably 40,000 or less, and even more preferably 30,000 or less. When the number average molecular weight of the first polymer is excessively large, the peel strength of the laminate tends to be reduced. This number average molecular weight can be measured in the same manner as for the second prepolymer.
  • the softening point of the first polymer is preferably 90°C or higher, more preferably 100°C or higher, and even more preferably 110°C or higher. If the softening point of the first polymer is high, the heat resistance of the laminate tends to improve and the adhesion tends to be higher. There is no particular upper limit to the softening point of the first polymer, but in one example it is 200°C or lower, and in another example it is 160°C or lower.
  • the softening point of the mixture can be measured in the same manner as for the second prepolymer.
  • the first polymer may exist as a mixture with the second prepolymer.
  • the mixture of the first polymer and the second prepolymer is obtained by adjusting the amount of the monofunctional active hydrogen compound. That is, the ratio M5/M6 of the molar amount M6 of the iso(thio)cyanate groups contained in the second prepolymer to the molar amount M5 of the active hydrogen groups contained in the monofunctional active hydrogen compound is adjusted to be less than 1, thereby producing a mixture of the second prepolymer and the first polymer in which the iso(thio)cyanate groups of the second prepolymer are protected with the monofunctional active hydrogen compound.
  • the ratio M5/M6 is preferably 0.75 or more and 0.95 or less.
  • the number average molecular weight of this mixture is preferably 5,000 or more, more preferably 10,000 or more, and even more preferably 13,000 or more. When a mixture with a high number average molecular weight is used, the peel strength of the laminate tends to be increased.
  • the number average molecular weight of the mixture is preferably 50,000 or less, more preferably 40,000 or less, and even more preferably 30,000 or less. When the number average molecular weight of the mixture is excessively high, the peel strength of the laminate tends to be reduced. This number average molecular weight can be measured in the same manner as for the second prepolymer.
  • the softening point of this mixture is preferably 90°C or higher, more preferably 100°C or higher, and even more preferably 110°C or higher. If the softening point of the mixture is high, the heat resistance of the laminate tends to improve and the adhesion tends to be higher. There is no particular upper limit to the softening point of the mixture, but in one example it is 200°C or lower, and in another example it is 160°C or lower.
  • the softening point of the mixture can be measured in the same manner as for the second prepolymer.
  • the proportion of the first polymer in the solid content of the composition for forming the functional layer is, for example, 75% by mass or more and 95% by mass or less.
  • the mixture of the first polymer and the second prepolymer may contain a fourth prepolymer.
  • the fourth prepolymer is a compound in which some of the iso(thio)cyanate groups of the second prepolymer are protected with a monofunctional active hydrogen compound, and the remainder are unprotected.
  • the fourth prepolymer may contain one iso(thio)cyanate group and one monofunctional active hydrogen compound protecting group. Since the fourth prepolymer has an iso(thio)cyanate group, it may increase the adhesion of the laminate, similar to the second prepolymer.
  • the proportion of the first polymer is, in one example, 1% by mass to 40% by mass, and in another example, 10% by mass to 30% by mass.
  • the proportion of the second prepolymer is, in one example, 1% by mass to 40% by mass, and in another example, 10% by mass to 30% by mass.
  • the proportion of the fourth prepolymer is, in one example, 1% by mass to 80% by mass, and in another example, 40% by mass to 80% by mass.
  • the adhesive layer may be a cured product of a functional layer-forming composition that includes a first polymer, a second prepolymer, and a fourth prepolymer, or may be a cured product of a functional layer-forming composition that includes a first polymer and a fourth prepolymer.
  • the monofunctional active hydrogen compound has one active hydrogen group.
  • the monofunctional active hydrogen compound reacts with the iso(thio)cyanate group of the second prepolymer to produce the first polymer and terminate further reaction.
  • the active hydrogen group includes at least one selected from the group consisting of a hydroxyl group, an amino group, a carboxyl group, and a thiol group.
  • the monofunctional active hydrogen compound includes at least one selected from the group consisting of a monool compound containing one hydroxyl group, a monoamine compound containing one amino group, a carboxylic acid containing one carboxyl group, and a monothiol compound containing one thiol group.
  • a monool compound containing one hydroxyl group a monoamine compound containing one amino group
  • a carboxylic acid containing one carboxyl group a monothiol compound containing one thiol group.
  • a monothiol compound containing one thiol group a single type may be used, or multiple types may be mixed and used.
  • the monofunctional active hydrogen compound is preferably a monoamine compound.
  • a monoamine compound is used, a first polymer having a (thio)urea bond is obtained.
  • the monofunctional active hydrogen compound preferably contains an amine having a 2,2,6,6-pentamethyl-4-piperidyl moiety, as shown in the following formula (3).
  • the amine having a 2,2,6,6-pentamethyl-4-piperidyl moiety can function as a hindered amine, thereby enhancing the light stability of the laminate.
  • R 21 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 22 is an alkylene group having 1 to 3 carbon atoms.
  • a is 0 or 1.
  • the monofunctional active hydrogen compound is preferably 1,2,2,6,6-pentamethyl-4-aminopiperidine in which R 21 is a methyl group and a is 0.
  • the ratio S5/S6 of the mass S5 of the monofunctional active hydrogen compound to the mass S6 of the second prepolymer is preferably 0.001 or more and 0.100 or less.
  • a first prepolymer having a sufficient amount of isocyanate groups per unit mass is obtained. It is more preferable that the ratio S5/S6 is 0.010 or more and 0.030 or less.
  • the third prepolymer is a compound having two or more iso(thio)cyanate groups obtained by reacting the first polyfunctional active hydrogen compound with the first iso(thio)cyanate compound. That is, the third prepolymer is a compound similar to the first prepolymer.
  • the third prepolymer chemically bonds with the first prepolymer and hydroxyl groups on the surfaces of the first and second substrates under high temperature to produce at least one selected from the group consisting of (thio)urethane resins, (thio)urea resins, and (thio)urethane urea resins.
  • the proportion of the third prepolymer in the solid content of the composition for forming the functional layer is, for example, 5% by mass or more and 20% by mass or less.
  • the composition for forming the functional layer may contain at least one additive selected from the group consisting of, for example, a polymerization catalyst, a polymerization initiator, an antistatic agent, an internal mold release agent, an antioxidant, a light stabilizer, a coloring inhibitor, a fluorescent dye, a dye, a pigment, a fragrance, a solvent, a leveling agent, and a resin modifier.
  • the composition for forming the functional layer preferably contains at least one of an antioxidant and a leveling agent.
  • IRGANOX 245 ethylene bis(oxyethylene)bis[3,5-tert-butyl-4-hydroxy-m-tolyl]propionate
  • IRGANOX 1076 octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
  • IRGANOX 1010 pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] manufactured by BASF Japan Ltd.
  • IRGANOX 1035, 1075, 104, 3790, 5057, 565, etc. manufactured by BASF Japan Ltd. can be used.
  • Leveling agents that can be used include silicone surfactants and fluorine-containing surfactants. Specifically, L-7001, L-7002, L-7604, and FZ-2123 manufactured by Dow Toray Co., Ltd., Megafac F-470, Megafac F-1405, and Megafac F-479 manufactured by DIC Corporation, and Florad FC-430 manufactured by 3M Japan Ltd. can be used.
  • a hindered amine compound having a 2,2,6,6-tetramethyl-4-piperidyl skeleton 2,2,6,6-tetramethyl-4-piperidyl skeleton
  • commercially available products can be used.
  • Product names include the Adeka STAB (registered trademark) LA series (LA-52, LA-57, LA-63P, LA-68, LA-72, LA-77Y, LA-81, LA-82, etc.) manufactured by ADEKA CORPORATION, the TINUVIN (registered trademark) series (TINUVIN123, TINUVIN171, TINUVIN249, TINUVIN292, TINUVIN765, TINUVIN622SF, etc.) manufactured by BASF Japan Ltd., and the Chimassorb (registered trademark) series (Chimassorb2020FDL, Chimassorb944FDL).
  • the proportion of additives in the solid content of the functional layer-forming composition is, for example, 0.1% by mass or more and 1% by mass or less.
  • the composition for forming a functional layer may contain an organic solvent to adjust its viscosity.
  • the organic solvent may include at least one selected from the group consisting of tetrahydrofuran, diethyl ketone, t-butyl alcohol, isopropyl alcohol, propylene glycol monomethyl ether, toluene, ethyl acetate, and cyclohexanone.
  • the proportion of the organic solvent in the composition for forming the functional layer is, for example, 30% by mass or more and 80% by mass or less.
  • composition for forming a functional layer can be obtained, for example, by the following first to fifth production methods.
  • the first method for producing a composition for forming a functional layer includes reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound to obtain a first prepolymer, reacting the first prepolymer with a second polyfunctional active hydrogen compound to obtain a second prepolymer, and mixing the second prepolymer with a functional dye and any additives.
  • the second method for producing a composition for forming a functional layer includes reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound to obtain a first prepolymer, reacting the first prepolymer with a second polyfunctional active hydrogen compound to obtain a second prepolymer, reacting the second prepolymer with a monofunctional active hydrogen compound to obtain a mixture of the first polymer and the second prepolymer, and mixing the first polymer, the second prepolymer, the functional dye, and any additives.
  • the third method for producing a composition for forming a functional layer includes reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound to obtain a first prepolymer and a third prepolymer, reacting the first prepolymer with a second polyfunctional active hydrogen compound to obtain a second prepolymer, reacting the second prepolymer with a monofunctional active hydrogen compound to obtain a first polymer, and mixing the first polymer, the third prepolymer, the functional dye, and any additives.
  • the fourth method for producing a composition for forming a functional layer includes reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound to obtain a first prepolymer, reacting the first prepolymer with a second polyfunctional active hydrogen compound to obtain a second prepolymer, reacting the second prepolymer with a monofunctional active hydrogen compound to obtain a mixture of the first polymer, the second prepolymer, and the fourth prepolymer, and mixing the first polymer, the second prepolymer, the fourth prepolymer, the functional dye, and any additives.
  • the fifth method for producing a composition for forming a functional layer includes reacting a first polyfunctional active hydrogen compound with a first iso(thio)cyanate compound to obtain a first prepolymer, reacting the first prepolymer with a second polyfunctional active hydrogen compound to obtain a second prepolymer, reacting the second prepolymer with a monofunctional active hydrogen compound to obtain a first polymer, and mixing the first polymer, the functional dye, and any additives.
  • the reaction between the first polyfunctional active hydrogen compound and the first iso(thio)cyanate compound is preferably carried out in the presence of an organic solvent.
  • the organic solvent may be any of those mentioned above.
  • This reaction is preferably carried out in a nitrogen atmosphere.
  • This reaction is also carried out, for example, at a reaction temperature of 60°C or higher and 150°C or lower for 3 hours or higher and 10 hours or lower. This reaction is preferably carried out until the end point is confirmed by back titration of the isocyanate group.
  • the reaction between the first prepolymer and the second polyfunctional active hydrogen compound is preferably carried out in the presence of an organic solvent.
  • the organic solvent may be any of those mentioned above.
  • This reaction is preferably carried out in a nitrogen atmosphere.
  • This reaction is also carried out, for example, at a reaction temperature of 10°C or higher and 30°C or lower for 0.1 hours to 5 hours.
  • the reaction between the second prepolymer and the monofunctional active hydrogen compound is preferably carried out in the presence of an organic solvent.
  • the organic solvent may be any of those mentioned above.
  • This reaction is preferably carried out in a nitrogen atmosphere.
  • This reaction is also carried out, for example, at a reaction temperature of -10°C or higher and 10°C or lower for 0.1 hours or higher and 5 hours or lower.
  • the preferred composition for forming a functional layer in the present invention is the first combination of a polymerization component containing only the second prepolymer and a functional dye.
  • the thickness of each of the first and second adhesive layers is, for example, 1 ⁇ m or more.
  • the thickness of the first and second adhesive layers is preferably 3 ⁇ m or more, more preferably 5 ⁇ m or more.
  • the thickness of the first and second adhesive layers is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less, and even more preferably 20 ⁇ m or less.
  • the thickness of the first and second adhesive layers may be 10 ⁇ m or less, or may be 8 ⁇ m or less.
  • At least one of the first and second adhesive layers contains at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins.
  • the type of resin contained in the first and second adhesive layers can be confirmed by gas chromatography or Fourier transform infrared spectroscopy (FT-IR) analysis.
  • polyvinyl alcohol (PVA) resin includes a fully saponified polyvinyl alcohol resin having only hydroxyl groups in the side chain, and a partially saponified polyvinyl alcohol resin having hydroxyl groups and acetate groups in the side chain.
  • the repeating unit of the fully saponified polyvinyl alcohol resin is represented, for example, by -[CH 2 CH(OH)] n -.
  • the saponification degree of the fully saponified polyvinyl alcohol resin is, for example, 98 mol% or more and 100 mol% or less.
  • the repeating unit of the partially saponified polyvinyl alcohol resin is represented, for example, by -[CH 2 CH(OH)] n -[CH 2 CH(OCOCH 3 )] m -.
  • the saponification degree of the partially saponified polyvinyl alcohol resin is, for example, 40 mol% or more and 97 mol% or less.
  • the saponification degree of the PVA resin can be measured by a method in accordance with Japanese Industrial Standards (JIS) K6726;1994. Specifically, the residual acetate group (mol %) in a sample is quantified using sodium hydroxide, and the degree of saponification (mol %) is determined by a dissolution titration method.
  • the modified polyvinyl alcohol resin means a polyvinyl alcohol resin in which a functional group other than a hydroxyl group and an acetate group is introduced into the side chain.
  • the functional group introduced is preferably highly hydrophobic.
  • a PVA resin in which a hydrophobic functional group is introduced is used, the performance of a functional dye can be improved.
  • Examples of functional groups other than a hydroxyl group and an acetate group include at least one selected from the group consisting of a butyral group, an acetoacetyl group, a quaternary ammonium group, a sulfo group, a carboxy group, an ethylene oxide group (-[CH 2 CH 2 O] X -H), and an alkyl group.
  • the quaternary ammonium group, the sulfo group, and the carboxy group may form a salt.
  • the repeating unit of the modified polyvinyl alcohol resin is represented by, for example, -[CH 2 CH(OH)] n -[CH 2 CH(OCOCH 3 )] m -[CH 2 CH(OX)] l -.
  • X is a monovalent functional group other than a hydroxyl group and an acetate group.
  • X is, for example, an acetoacetyl group, a quaternary ammonium group, a sulfo group, a carboxy group, an ethylene oxide group, an alkyl group, or an amino group.
  • the degree of saponification of the modified polyvinyl alcohol resin is, for example, 40 mol % or more and 99 mol % or less.
  • the polyvinyl resin may be a copolymer of vinyl alcohol and other monomers, such as vinylamine.
  • the PVA resin preferably contains at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resin, polyvinyl butyral resin, acetoacetylated polyvinyl alcohol resin, and amine-functional polyvinyl alcohol resin.
  • the number average molecular weight of the PVA resin is, for example, from 10,000 to 200,000.
  • the number average molecular weight of the PVA resin is preferably from 20,000 to 180,000, more preferably from 30,000 to 150,000, and even more preferably from 50,000 to 110,000.
  • the number average molecular weight of the PVA resin can be measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the average degree of polymerization of the PVA resin is, for example, from 100 to 10,000, preferably from 500 to 8,000, and more preferably from 1,000 to 5,000.
  • the average degree of polymerization of the PVA resin may be from 1,200 to 2,000.
  • the average degree of polymerization of the PVA resin is determined by a method in accordance with Japanese Industrial Standards (JIS) K6726;1994.
  • JIS Japanese Industrial Standards
  • the first and second adhesive layers can be formed, for example, by applying the adhesive layer-forming composition described below onto at least one surface of the first and second optical substrates and curing the composition.
  • the first and second adhesive layers are typically non-self-supporting films.
  • the adhesive layer-forming composition may contain at least one resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins, and water or an organic solvent in which the resin is dissolved or dispersed.
  • a resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins, and water or an organic solvent in which the resin is dissolved or dispersed.
  • water distilled water, pure water, ion-exchanged water, or tap water can be used.
  • the adhesive layer forming composition preferably contains at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resin, polyvinyl butyral resin, acetoacetylated polyvinyl alcohol resin, and amine-functional polyvinyl alcohol resin, and more preferably contains polyvinyl alcohol resin.
  • the organic solvent is, for example, at least one selected from the group consisting of methyl ethyl ketone, toluene, methanol, ethanol, normal propanol, isopropanol, acetone, phenol, diethyl ketone, xylene, dimethyl sulfoxide, dimethylformamide, ethylenediamine, and diethylenetriamine.
  • a mixed solvent of water and an organic solvent may also be used.
  • the proportion of the resin in the adhesive layer forming composition is, for example, 1% by mass or more and 50% by mass or less, preferably 5% by mass or more and 30% by mass or less, and more preferably 8% by mass or more and 15% by mass or less.
  • the adhesive layer forming composition may further contain a first compound having at least one functional group selected from the group consisting of an acryloyl group, a methacryloyl group, and a vinyl group.
  • the first compound having a (meth)acryloyl group is, for example, a monofunctional (meth)acrylate having one (meth)acryloyl group.
  • a monofunctional (meth)acrylate having such a functional group is used, the adhesion of the adhesive layer tends to be increased.
  • monofunctional (meth)acrylates include methoxypolyethylene glycol methacrylate, methoxypolyethylene glycol methacrylate, methoxypolyethylene glycol acrylate, methoxypolyethylene glycol acrylate, stearyl methacrylate, lauryl methacrylate, methyl acrylate, ethyl acrylate, butyl acrylate, octyl acrylate, lauryl acrylate, ⁇ -methacryloyloxypropyltrimethoxysilane, and ⁇ -methacryloyloxypropylmethyldimethoxysilane.
  • the proportion of the first compound in the composition for forming the adhesive layer is, for example, 0.05% by mass or more and 5% by mass or less, and preferably 0.1% by mass or more and 1% by mass or less. If the proportion of the first compound is high, the adhesion of the adhesive layer tends to be improved. If the proportion of the first compound is low, the appearance of the laminate tends to be improved.
  • polyvinyl alcohol resins include Kuraray Poval 22-88 (partially saponified product), 28-98 (fully saponified product), and RS-2117 (fully saponified product) manufactured by Kuraray Co., Ltd. Also available is ULTILOC 5003 (fully saponified product, amine-functional polyvinyl alcohol) manufactured by Sekisui Chemical Co., Ltd.
  • the adhesive layer forming composition can be prepared, for example, by dissolving a commercially available polyvinyl alcohol resin in distilled water.
  • the manufacturing method of the laminate according to the embodiment includes, for example, applying the above-mentioned adhesive layer forming composition to at least one of the main surfaces of the first optical substrate and the second optical substrate and drying to provide a first coating film and a second coating film, applying the above-mentioned functional layer forming composition on the support to obtain a third coating film, peeling the third coating film from the support and laminating it on the first coating film of the first optical substrate, laminating the second optical substrate so that the second coating film is laminated on the third coating film laminated on the first coating film of the first optical substrate to obtain a first structure, and heating the first structure to harden the first coating film, the second coating film, and the third coating film.
  • the functional layer forming composition may be applied on the first coating film and dried to directly provide the third coating film.
  • the adhesive layer forming composition is applied onto the second main surfaces of the first optical substrate and the second optical substrate using, for example, a bar coater to form a coating film.
  • This coating film is dried, for example, at a temperature of 70°C or higher and 150°C or lower for 1 minute to 5 hours. This results in a first optical substrate having a first coating film formed on one main surface, and a second optical substrate having a second coating film formed on one main surface.
  • the functional layer forming composition is applied onto the support to form a coating film.
  • This coating film is dried, for example, at a temperature of 70°C or higher and 150°C or lower for 1 minute to 1 hour. This results in a third coating film.
  • the third coating film peeled off from the support is laminated onto the first coating film on the first optical substrate. This results in a structure in which the first optical substrate, the first coating film, and the third coating film are laminated in this order.
  • the second coating film is laminated on the second optical substrate so as to be in contact with the third coating film. This results in a first structure in which the first optical substrate, the first coating film, the third coating film, the second coating film, and the second optical substrate are laminated in this order.
  • the first structure is heated to harden the first to third coating films. This results in a laminate in which the first optical substrate and the second optical substrate are bonded via the first adhesive layer, the functional layer, and the second adhesive layer.
  • the heat treatment of the first structure for example, it is heated at a temperature of 40°C to 160°C for 1 minute to 10 hours.
  • the obtained laminate may be subjected to a degassing treatment.
  • the laminate is left to stand, for example, under a vacuum of 500 Pa at a temperature of 40°C to 80°C for 5 hours to 20 hours.
  • the structure after the degassing treatment may further be subjected to a heat treatment.
  • the laminate according to the embodiment may further include a support.
  • the support may be located between the functional layer and the first or second adhesive layer, or between the first or second adhesive layer and the first or second optical substrate.
  • the support may further enhance the shape stability of the laminate.
  • the support may be colorless and transparent, white and transparent, or colored and transparent.
  • the support preferably contains at least one resin selected from the group consisting of, for example, polyethylene terephthalate, triacetyl cellulose, polyamide, polycarbonate sheet, cellulose acetate butyrate, and (meth)acrylic.
  • the thickness of the support is preferably 50 ⁇ m or more.
  • the coating layer-containing laminate according to the embodiment includes the laminate according to the embodiment and a coating layer.
  • the coating layer covers at least a part of the first optical substrate and the second optical substrate.
  • the coating layer includes at least one resin selected from the group consisting of an epoxy resin, an oxetane resin, an acrylic resin, a methacrylic resin, and a urethane resin.
  • the coated layer-containing laminate can be used as the binder sheet described above, similar to the laminate according to the embodiment.
  • the coated layer-containing laminate has excellent processing stability because it contains a coated layer. It also has excellent adhesion to the optical element substrate described below.
  • the thickness of the coating layer-containing laminate according to the embodiment is preferably 100 ⁇ m or more, more preferably 150 ⁇ m or more, and even more preferably 200 ⁇ m or more.
  • the thickness of the coating layer-containing laminate is large, shape stability tends to be improved.
  • FIG. 2 is a cross-sectional view showing an example of a coated layer-containing laminate according to an embodiment.
  • the coated layer-containing laminate 7 shown in FIG. 2 includes the laminate 1 shown in FIG. 1, a first coating layer 5 that entirely covers the first main surface 2a of the first optical substrate 2, and a second coating layer 6 that entirely covers the first main surface 3a of the second optical substrate 3.
  • the first adhesive layer FA and the second adhesive layer SA are omitted.
  • the first coating layer 5 may cover a part of the first main surface 2a
  • the second coating layer 6 may cover a part of the first main surface 3a.
  • One of the first coating layer 5 and the second coating layer 6 may be omitted.
  • the coating layer covers at least a part of the surface of at least one of the first and second optical substrates.
  • the coating layer preferably covers the surfaces of both the first and second optical substrates.
  • the coating layer preferably covers the entire surfaces of the first and second optical substrates.
  • the thickness of the coating layer is, for example, 5 ⁇ m or more. If the coating layer is thick, the adhesion to the optical element substrate and the shape stability of the laminate tend to be improved.
  • the thickness of the coating layer is preferably 10 ⁇ m or more, more preferably 20 ⁇ m or more, and even more preferably 25 ⁇ m or more. On the other hand, if the coating layer is excessively thick, the appearance of the laminate tends to deteriorate.
  • the thickness of the coating layer is preferably 100 ⁇ m or less, more preferably 75 ⁇ m or less, and even more preferably 50 ⁇ m or less.
  • the coating layer contains at least one resin selected from the group consisting of epoxy resin, oxetane resin, acrylic resin, methacrylic resin, and urethane resin.
  • the coating layer preferably contains an epoxy resin. Coating layers containing epoxy resin tend to have excellent appearance and higher adhesion to the optical element substrate. The type of resin contained in the coating layer can be confirmed by gas chromatography or Fourier transform infrared spectroscopy (FT-IR) analysis.
  • FT-IR Fourier transform infrared spectroscopy
  • the surface of the coating layer preferably has at least one functional group selected from the group consisting of epoxy groups, acryloyl groups, methacryloyl groups, and vinyl groups. Having a coating layer with these functional groups on its surface tends to improve adhesion to the optical element substrate. It is more preferable that the coating layer contains at least one functional group selected from the group consisting of acryloyl groups, methacryloyl groups, and vinyl groups, and an epoxy group. Such a coating layer can further improve adhesion.
  • FT-IR Fourier transform infrared spectroscopy
  • the coating layer can be formed, for example, by applying the above-mentioned adhesive layer-forming composition onto the surface of at least one of the first and second optical substrates and curing it.
  • the adhesive layer-forming composition is applied onto the first main surface of each of the first optical substrate and the second optical substrate, and then dried, for example, at a temperature of 70°C to 150°C for 1 minute to 1 hour.
  • a coating layer-containing laminate is obtained by the same method as the laminate manufacturing method described above.
  • the optical article according to the embodiment includes the laminate according to the embodiment.
  • the optical article may include the laminate according to the embodiment and an optical element substrate that covers at least a part of the first optical substrate and the second optical substrate.
  • the optical article may also include the coating layer-containing laminate according to the embodiment.
  • the optical article may include the coating layer-containing laminate according to the embodiment and an optical element substrate that covers at least a part of the coating layer.
  • Optical articles include binder sheets, lenses, eyeglasses, window materials for houses and automobiles, window films, liquid crystal displays, sun visors, watches, etc.
  • Lenses include semi-finished lenses and finished lenses.
  • FIG. 3 is a cross-sectional view that shows an example of an optical article according to an embodiment.
  • the optical article 10 shown in FIG. 3 includes a first optical element substrate 12, a second optical element substrate 11, and the laminate 1 shown in FIG. 1 interposed therebetween.
  • the optical article 10 has a concave-convex lens shape.
  • the laminate 1 has a curved surface that conforms to the shape of the lens.
  • the first optical element substrate 12 is located on the convex side, and the second optical element substrate 12 is located on the concave side.
  • the first optical element substrate 12 covers the entire surface of the first optical substrate (not shown) of the laminate 1.
  • the second optical element substrate 11 covers the entire surface of the second optical substrate (not shown) of the laminate 1.
  • the side surfaces of the laminate 1 are not covered by the first and second optical element substrates.
  • the side surfaces of the laminate 1 may be covered by the first and second optical element substrates.
  • a coated layer-containing laminate 7 shown in FIG. 2 may be used.
  • the first optical element substrate 12 may cover the entire surface of the first coating layer 5 of the coated layer-containing laminate 7.
  • the second optical element substrate 11 may cover the entire surface of the second coating layer 6 of the coated layer-containing laminate 7.
  • FIG. 4 is a perspective view that shows a schematic example of glasses according to an embodiment.
  • the glasses 100 shown in FIG. 4 include a lens 101 and a frame 102 that supports the lens 101.
  • the lens 101 includes an optical article according to an embodiment.
  • the optical element substrate may include a resin, which may include at least one resin selected from the group consisting of a polyester resin, a polyamide resin, an allyl resin, a (meth)acrylic resin, a polyurethane resin, a polyurethane urea resin, a polythiourethane resin, a polythiourethane urea resin, a polythioepoxy resin, and a polycarbonate resin.
  • a resin which may include at least one resin selected from the group consisting of a polyester resin, a polyamide resin, an allyl resin, a (meth)acrylic resin, a polyurethane resin, a polyurethane urea resin, a polythiourethane resin, a polythiourethane urea resin, a polythioepoxy resin, and a polycarbonate resin.
  • the optical element substrate preferably contains an allyl resin, a (meth)acrylic resin, a polyurethane urea resin, a polythiourethane resin, or a polythioepoxy resin. Allyl resins and (meth)acrylic resins tend to have high adhesion to the optical substrate or coating layer of the laminate.
  • curable composition for forming optical element substrate examples include a curable composition for an allyl resin, a curable composition for a (meth)acrylic resin, a curable composition for a urethane urea resin, and a curable composition for a thiourethane resin.
  • a curable composition for an epoxy resin or a curable composition for a thioepoxy resin may be used.
  • the curable composition for (meth)acrylic resins contains a (meth)acrylic monomer having a (meth)acryloyl group and a polymerization initiator.
  • the curable composition for the urethane urea resin contains a prepolymer of a polyisocyanate compound and a polyol compound, and a diamine compound.
  • the polyisocyanate compound, polyol compound, and diamine compound may be the same as those described above in the composition for forming the functional layer.
  • the curable composition for the thiourethane resin contains a polyisocyanate compound, a polythiol compound, and a polymerization catalyst.
  • the polyisocyanate compound may be any of those described above in the composition for forming the functional layer.
  • the curable composition for thioepoxy resins contains a monomer having a thioepoxy group, a curing agent, and a polymerization catalyst.
  • the curable composition for allyl or (meth)acrylic resins contains a first monomer having an allyl or (meth)acryloyl group and a polymerization initiator. It is preferable that the curable composition for allyl or (meth)acrylic resins further contains at least one of a second monomer and an organosilicon compound.
  • the second monomer has a polymerizable group and a first functional group.
  • the polymerizable group is at least one selected from the group consisting of an acryloyl group, a methacryloyl group, and a vinyl group.
  • the first functional group is at least one selected from the group consisting of an isocyanate group, an isothiocyanate group, an epoxy group, an oxetanyl group, and an aldehyde group.
  • the organosilicon compound has a second functional group and a hydrolyzable group.
  • the second functional group is at least one selected from the group consisting of an acryloyl group, a methacryloyl group, and a vinyl group.
  • the polymerizable group of the second monomer can polymerize with the allyl group or (meth)acryloyl group of the first monomer.
  • the polymerizable groups of the second monomer can polymerize with each other to form a relatively long molecular chain. This molecular chain and the first monomer can be entangled with each other.
  • the first functional group of the second monomer can bond to the surface of the optical substrate.
  • the first functional group of the second monomer reacts with a hydroxyl group present on the surface of the substrate to form a urethane bond, a thiourethane bond, an ether bond, or an acetal bond.
  • the polymerizable group chemically bonds with the first monomer or physically captures the first monomer, and the first functional group can bond with the surface of the substrate.
  • the second monomer can crosslink the surface of the substrate and the first monomer. Therefore, by using a curable composition containing the second monomer, the adhesion between the cured body and the substrate can be improved.
  • the organosilicon compound also has a second functional group and a hydrolyzable group.
  • the second functional group can polymerize with the allyl group or (meth)acryloyl group of the first monomer.
  • the hydrolyzable group can react with a hydroxyl group present on the surface of the substrate. For example, the hydrolyzable group undergoes dehydration condensation with the hydroxyl group to form a siloxane bond or a Si-O-C bond. That is, in the organosilicon compound, the second functional group can chemically bond with the first monomer, and the hydrolyzable group can bond with the surface of the substrate. In this way, the organosilicon compound can crosslink the surface of the substrate with the first monomer. Therefore, by using a curable composition containing an organosilicon compound, the adhesion between the cured body and the substrate can be improved.
  • the first monomer may contain one allyl group or one (meth)acryloyl group, or may contain two or more allyl groups or may contain both an allyl group and a (meth)acryloyl group.
  • the first monomer preferably contains two allyl groups or two (meth)acryloyl groups.
  • the first monomer preferably has allyl groups or (meth)acryloyl groups at both ends of the main chain.
  • the first monomer may contain one carbonate group, or two or more carbonate groups. It is preferable that the first monomer contains two carbonate groups.
  • the first monomer having an allyl group include at least one selected from the group consisting of allyl diglycol carbonate, diallyl isophthalate, and diallyl terephthalate. It is preferable that the first monomer includes allyl diglycol carbonate.
  • the first monomer is preferably a monomer for forming a plastic lens.
  • the first monomer may be the main component in the curable composition.
  • the proportion of the first monomer in the curable composition is, for example, 50% by mass or more, preferably 75% by mass or more, and more preferably 90% by mass or more. When the proportion of the first monomer is high, the appearance and durability of the cured body tend to be improved.
  • the proportion of the first monomer in the curable composition is, for example, 99.5% by mass or less, and preferably 98% by mass or less. When the proportion of the first monomer is low, the adhesion between the cured body and the substrate tends to be improved.
  • the proportion of the first monomer in the curable composition can be calculated, for example, by isolating the first monomer from the curable composition by silica gel chromatography or the like and measuring the weight of the resulting first monomer, or by analysis by gas chromatography or liquid chromatography.
  • the second monomer has a polymerizable group and a first functional group.
  • the second monomer may contain one polymerizable group, or may contain two or more polymerizable groups. It is preferable that the second monomer contains one polymerizable group.
  • the second monomer may contain one first functional group, or may contain two or more first functional groups. It is preferable that the second monomer contains one first functional group.
  • the polymerizable group is preferably an acryloyl group or a methacryloyl group.
  • the first functional group is preferably at least one selected from the group consisting of an isocyanate group and an isothiocyanate group, and more preferably an isocyanate group.
  • the second monomer preferably contains a compound represented by the following formula (I):
  • R1 is an acryloyl group, a methacryloyl group, or a vinyl group
  • R2 is an isocyanate group or an isothiocyanate group.
  • X is a linear or branched alkylene group having 1 to 10 carbon atoms, or an alkyleneoxyalkylene group having 2 to 10 carbon atoms.
  • the alkylene group preferably has 1 to 5 carbon atoms.
  • the alkylene group is more preferably a methylene group or an ethylene group.
  • the alkyleneoxyalkylene group preferably has 2 to 6 carbon atoms.
  • the alkyleneoxyalkylene group is more preferably an ethyleneoxyethylene group.
  • a is 0 or 1.
  • the second monomer include at least one selected from the group consisting of 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate, allyl isothiocyanate, allyl isocyanate, (3-ethyl-3-oxetanyl)methyl methacrylate, and (3-ethyl-3-oxetanyl)methyl acrylate. It is preferable that the second monomer includes at least one selected from the group consisting of 2-isocyanatoethyl acrylate and 2-isocyanatoethyl methacrylate.
  • the proportion of the second monomer in the curable composition is, for example, 0.1 mass% or more, preferably 0.5 mass% or more, and more preferably 1.0 mass% or more. When the proportion of the second monomer is high, the adhesion between the cured body and the substrate tends to be improved.
  • the proportion of the second monomer in the curable composition is, for example, 30 mass% or less, preferably 15 mass% or less, and more preferably 10 mass% or less. When the proportion of the second monomer is low, the appearance of the cured body tends to be improved.
  • the ratio M2/M1 of the mass M2 of the second monomer to the mass M1 of the first monomer is preferably 0.005 or more and 0.20 or less, more preferably 0.01 or more and 0.15 or less, and even more preferably 0.02 or more and 0.10 or less.
  • the ratio M2/M1 is within this range, a cured product that is excellent in both adhesion to the substrate and appearance tends to be obtained.
  • the proportion of the second monomer in the curable composition can be calculated, for example, by isolating the second monomer from the curable composition by silica gel chromatography or the like and measuring the weight of the obtained second monomer, or by analysis by gas chromatography or liquid chromatography.
  • the organosilicon compound has a second functional group and a hydrolyzable group.
  • the second monomer may contain one second functional group, or may contain two or more second functional groups.
  • the second monomer preferably contains one second functional group.
  • the second monomer may contain one hydrolyzable group, or may contain two or more hydrolyzable groups.
  • the second monomer preferably contains 5 or less hydrolyzable groups, more preferably 3 or less hydrolyzable groups.
  • the second functional group is at least one selected from the group consisting of an acryloyl group, a methacryloyl group, and a vinyl group.
  • the hydrolyzable group contains at least one selected from the group consisting of an alkyloxy group having from 1 to 3 carbon atoms and an alkyloxysilyl group having from 1 to 3 carbon atoms.
  • the hydrolyzable group preferably contains a trialkyloxysilyl group, and more preferably contains at least one of a trimethyloxysilyl group ((MeO) 3 Si-) and a triethyloxysilyl group ((EtO) 3 Si-).
  • the organosilicon compound preferably contains a compound represented by the following formula (2):
  • R4 and R5 are each an alkyl group having 1 to 3 carbon atoms. It is preferable that R4 and R5 are each a methyl group or an ethyl group. d is an integer of 0 to 2. It is preferable that d is 0.
  • A is an alkylene group having 1 to 10 carbon atoms, an oxyalkylene group having 1 to 10 carbon atoms, an alkyleneoxyalkylene group having 2 to 10 carbon atoms, an aminoalkylene group having 1 to 10 carbon atoms, or a phenylene group.
  • A is preferably an ethylene group, a propylene group, an oxyethylene group, an oxypropylene group, or an alkyleneoxyalkylene group having 3 to 6 carbon atoms, and more preferably a propyleneoxymethylene group.
  • X is an acryloyl group, a methacryloyl group, or a vinyl group. X is preferably an acryloyl group or a methacryloyl group.
  • organosilicon compounds having a (meth)acryloyl group include ⁇ -methacryloyloxypropyltrimethoxysilane, ⁇ -methacryloyloxypropyltriethoxysilane, ⁇ -methacryloyloxypropylmethyldimethoxysilane, (3-acryloxypropyl)dimethylmethoxysilane, (3-acryloxypropyl)methyldimethoxysilane, (3-acryloxypropyl)trimethoxysilane, methacryloxyethoxytrimethylsilane, (methacryloxymethyl)dimethylethoxysilane, methacryloxymethyltriethoxysilane, methacryloxymethyltrimethoxysilane, methacryloxypropyldimethylethoxysilane, methacryloxypropyldimethylmethoxysilane, methacryloxypropyltris(methoxyethoxy)silane, etc.
  • organosilicon compounds having vinyl groups include vinyltriethoxysilane, vinyltrimethoxysilane, vinyltris( ⁇ -methoxyethoxy)silane, p-styryltrimethoxysilane, and p-styryltriethoxysilane.
  • silane coupling agents As the organosilicon compound, commercially available silane coupling agents can be used.
  • the proportion of the organosilicon compound in the curable composition is, for example, 0.1 mass% or more, preferably 0.5 mass% or more, and more preferably 1.0 mass% or more.
  • the proportion of the second monomer in the curable composition is, for example, 30 mass% or less, preferably 15 mass% or less, and more preferably 10 mass% or less.
  • the proportion of the organosilicon compound is low, the appearance of the cured body tends to be improved.
  • the ratio M3/M1 of the mass M3 of the organosilicon compound to the mass M1 of the first monomer is preferably 0.005 or more and 0.20 or less, more preferably 0.01 or more and 0.15 or less, and even more preferably 0.02 or more and 0.10 or less.
  • the ratio M3/M1 is within this range, a cured product that is excellent in both adhesion to the substrate and appearance tends to be obtained.
  • the proportion of the organosilicon compound in the curable composition can be calculated, for example, by isolating the organosilicon compound from the curable composition by silica gel chromatography or the like and measuring the weight of the resulting organosilicon compound, or by analysis by gas chromatography or liquid chromatography.
  • the curable composition may contain either the second monomer or the organosilicon compound, or may contain both.
  • the curable composition may contain other components in addition to the above components.
  • the other components include at least one additive selected from the group consisting of a polymerization initiator, a polymerization catalyst, an antistatic agent, an internal mold release agent, an antioxidant, a light stabilizer, a color inhibitor, a fluorescent dye, a dye, a pigment, a fragrance, a solvent, a leveling agent, a resin modifier, an infrared absorber, an ultraviolet absorber, and a visible light absorber.
  • Polymerization initiators include 1,1-azobiscyclohexane carbonate, diisopropyl peroxycarbonate, 1,1'-azobiscyclohexane nitrate, di-tert-butyl peroxide, etc.
  • the amount of the polymerization initiator is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, and even more preferably 1.0 parts by mass or more, per 100 parts by mass of the first monomer.
  • the amount of the polymerization initiator is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and even more preferably 5 parts by mass or less.
  • the proportion of the polymerization initiator in the curable composition is, for example, 0.1% by mass or more and 10% by mass or less, preferably 0.5% by mass or more and 8% by mass or less, and more preferably 1.0% by mass or more and 5% by mass or less.
  • the curable composition preferably contains a polymerization catalyst.
  • the curable composition preferably contains at least one polymerization catalyst selected from the group consisting of a urethane reaction catalyst, a urea reaction catalyst, and an isocyanurate reaction catalyst, and more preferably contains an isocyanurate reaction catalyst.
  • Reaction catalysts for urethane or urea include tertiary amines, quaternary ammonium salts, quaternary phosphonium salts, Lewis acids, and organic sulfonic acids. Specific examples are shown below.
  • Tertiary amines include triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, triethylamine, hexamethylenetetramine, N,N-dimethyloctylamine, N,N,N',N'-tetramethyl-1,6-diaminohexane, 4,4'-trimethylenebis(1-methylpiperidine), 1,8-diazabicyclo-(5,4,0)-7-undecene, etc.
  • Phosphines include trimethylphosphine, triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tribenzylphosphine, 1,2-bis(diphenylphosphino)ethane, and 1,2-bis(dimethylphosphino)ethane.
  • Quaternary ammonium salts include tetramethylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, etc.
  • Quaternary phosphonium salts include tetramethylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, etc.
  • Lewis acids include triphenylaluminum, dimethyltin dichloride, dimethyltin bis(isooctylthioglycolate), dibutyltin dichloride, dibutyltin dilaurate, dibutyltin maleate, dibutyltin maleate polymer, dibutyltin diricinoleate, dibutyltin bis(dodecyl mercaptide), dibutyltin bis(isooctylthioglycolate), dioctyltin dichloride, dioctyltin maleate, dioctyltin maleate polymer, dioctyltin dimethacrylate ...
  • metal salts such as copper oleate, copper acetylacetonate, iron acetylacetonate, iron naphthenate, iron lactate, iron citrate, iron gluconate, potassium octanoate, and 2-e
  • Organic sulfonic acids include methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.
  • the reaction catalyst for isocyanurate may be at least one selected from the group consisting of quaternary ammonium salts, alkali metal salts, and tertiary amines.
  • quaternary ammonium salts include triethylmethylammonium 2-ethylhexane, trimethyl(2-hydroxypropyl)ammonium 2-ethylhexane salt, and trimethyl(2-hydroxypropyl)ammonium formate.
  • alkali metal salts include potassium acetate, potassium octoate, and potassium 2-ethylhexane.
  • tertiary amines examples include N,N,N',N'',N''-pentamethyldiethylenetriamine, 1,2-dimethylimidazole, and N,N-dimethylcyclohexylamine. It is preferable to use a quaternary ammonium salt as the catalyst for isocyanurate.
  • reaction catalysts for isocyanurates include POLYCAT (registered trademark) 46 (manufactured by Air Products), TOYOCAT (registered trademark) TRC (manufactured by Tosoh Corporation), TOYOCAT (registered trademark) TRX (manufactured by Tosoh Corporation), TOYOCAT (registered trademark) TRV (manufactured by Tosoh Corporation), TOYOCAT (registered trademark) TR-20 (manufactured by Tosoh Corporation), and U-CAT (registered trademark) 18X (manufactured by San-Apro Ltd.).
  • the proportion of the polymerization catalyst in the curable composition is, for example, 1 ppm or more and 1000 ppm or less, preferably 3 ppm or more and 100 ppm or less, and more preferably 5 ppm or more and 50 ppm or less.
  • the viscosity (23°C) of the curable composition is preferably 10 to 1000 mPa ⁇ s, more preferably 10 to 500 mPa ⁇ s, and even more preferably 10 to 100 mPa ⁇ s.
  • the viscosity of the curable composition is stable within a certain range during filling. For example, it is desirable that the viscosity V i at the beginning of filling and the viscosity V 3h after 3 hours have the following relationship.
  • V3h ⁇ 3Vi a hardened body can be stably produced in the production process.
  • the optical article according to the embodiment is produced, for example, by the following method.
  • a mold and a gasket are prepared.
  • the mold includes an upper mold and a lower mold.
  • the upper mold and the lower mold are combined to form a hollow portion inside.
  • the gasket is placed at the interface between the upper mold and the lower mold.
  • the gasket has a notch on the inside for fixing the laminate.
  • the gasket may have a convex portion or a concave portion instead of the notch on the inside.
  • the mold and the gasket are, for example, those known for molding plastic lenses.
  • the laminate may be subjected to a shape processing such as curving to match the shape of the mold.
  • a shape processing such as curving to match the shape of the mold.
  • the laminate is placed in a mold of a curved surface processing device.
  • the mold has, for example, a lens shape such as a hemisphere.
  • a hole is provided in the bottom surface of the mold.
  • a pressure adjustment device such as a vacuum pump is connected to the hole via a tube. The pressure adjustment device is started to reduce the pressure in the space between the mold and the laminate. This causes the first optical substrate of the laminate to deform so as to stick to the bottom surface of the mold.
  • the environmental temperature may be set to 70°C or higher and 160°C or lower so that the laminate can be easily deformed.
  • the operation of the pressure adjustment device is stopped and the deformed laminate is removed from the mold.
  • the removed laminate is cooled, for example, at a temperature of 0°C or higher and 40°C or lower. In this manner, a curved laminate is obtained.
  • the end of the laminate is inserted into the notch of the gasket and fixed.
  • This gasket is placed on the boundary surface of the mold.
  • the hollow part of the mold is filled with the curable composition for forming the optical element substrate.
  • the mold after being filled with the curable composition is heat treated to cure the curable composition.
  • the temperature is gradually increased from room temperature to the curing temperature, and after the curing temperature is reached, the temperature is maintained for a certain period of time.
  • the curing temperature is, for example, 60°C or higher and 100°C or lower.
  • the heating rate is, for example, 1°C/hour or higher and 10°C/hour or lower.
  • the retention time at the curing temperature is, for example, 1 hour or higher and 30 hours or lower.
  • the hardened body is removed from the mold.
  • the hardened body is then heated at a temperature in the range of 60°C to 150°C for an additional 1 hour to 10 hours. In this manner, an optical article is obtained in which the surfaces of the first and second optical substrates of the laminate are covered with the optical element substrate.
  • the optical article according to the embodiment may be obtained by the following method. First, a part of the curable composition is filled into the lower part of the above-mentioned mold. A laminate is placed on the surface of the filled curable composition. Next, an upper part is placed facing the lower part to form a hollow part. The remainder of the curable composition is filled into this hollow part. The obtained mold is heated in the same manner as above to obtain a cured body. In this way, an optical article in which the entire main surface and side surfaces of the laminate are covered with the optical element substrate according to the embodiment is obtained.
  • the optical article according to the embodiment may be obtained by the following method. First, a laminate is placed along the upper surface of a mold.
  • a curable composition is filled toward the surface of the laminate that is not in contact with the upper surface of the mold, i.e., the back side, and a first cured body is obtained by heat treatment under the same conditions as above. This first cured body is placed in a mold.
  • a curable composition is filled toward the surface of the laminate that is not covered by the cured body, and a second cured body is obtained by heat treatment under the same conditions as above. In this way, an optical article in which the main surface and optionally the side surface of the laminate are covered by the optical element substrate is obtained.
  • a laminate containing a coating layer may be used instead of the laminate.
  • Example 1 (Production of first prepolymer FPP1) A mixture was obtained by adding 100 g of the first isocyanate compound FI1, 315 g of the first multifunctional active hydrogen compound FA1, and 40 g of the organic solvent OS1 to a 2L reaction vessel. Isophorone diisocyanate was used as the first isocyanate compound FI1. A polycarbonate diol having a number average molecular weight of 1000 was used as the first multifunctional active hydrogen compound FA1. Diethyl ketone was used as the organic solvent OS1. The mixture was stirred at 150 rpm for 5 hours at 100° C. under a nitrogen atmosphere to obtain a reaction solution containing a first prepolymer. Hereinafter, this first prepolymer is also referred to as the first prepolymer FPP1. The end point of the reaction was confirmed by a back titration method of the isocyanate group.
  • Second prepolymer SPP1 560 g of organic solvent OS1 and 150 g of organic solvent OS2 were added to the reaction liquid containing the first prepolymer FPP1 at 10 ° C., and the liquid temperature was then maintained at 15 ° C.
  • organic solvent OS2 tert-butyl alcohol was used.
  • 21.3 g of the second polyfunctional active hydrogen compound SA1 was dropped into this reaction liquid, and the reaction was allowed to proceed at 15 ° C. for 1 hour, thereby obtaining a reaction liquid containing a second prepolymer.
  • the second polyfunctional active hydrogen compound SA1 bis-(4-aminocyclohexyl)methane was used.
  • this second prepolymer is also referred to as the second prepolymer SPP1.
  • the solid content concentration in the reaction liquid containing the second prepolymer SPP1 was 37.6% by mass.
  • the number average molecular weight of the second prepolymer SPP1 was measured and found to be 13,000.
  • the softening point was also found to be 98°C.
  • PC1 A compound represented by the following formula:
  • adhesive layer-forming composition PVA1 160 g of Kuraray Poval (registered trademark) 28-98 (fully saponified product, degree of saponification: 98.5 mol%, number average molecular weight: 90700, degree of polymerization: 1850) manufactured by Kuraray Co., Ltd. was added to a 2 L reaction vessel, and mixed with 1440 g of distilled water to obtain a mixture. This mixture was heated and stirred at 95°C for 2 hours to obtain an adhesive composition with a solid content concentration of 10 mass %.
  • this adhesive composition is referred to as adhesive composition PVA1.
  • the number average molecular weight of Kuraray Poval 28-98 was measured by gel permeation chromatography (GPC) under the following conditions.
  • sample solution 5 ml of measurement solvent (hexafluoroisopropanol with 5 mM sodium trifluoroacetate) was added to 3 mg of raw material to obtain a sample solution.
  • the sample solution was measured using columns: TSKgel guardcolumn Super H-H and TSKgel Super HM-H (manufactured by Tosoh Corporation), eluent: hexafluoroisopropanol with 5 mM sodium trifluoroacetate, flow rate: 0.3 ml/min, detector: RI detector (RI-504 manufactured by Showa Denko K.K.), and column temperature: 40°C.
  • the measurement results are as described above.
  • a saponified TAC film having a thickness of 60 ⁇ m was prepared as the first and second optical substrates.
  • the contact angle of this TAC film with pure water was 10°.
  • this film will also be referred to as TAC1.
  • the contact angle was measured using DropMaster 500 manufactured by Kyowa Interface Science Co., Ltd. The angle between the water droplet and the sheet sample surface when a water droplet was dropped on the sheet sample surface was measured and used as the contact angle.
  • the adhesive layer forming composition PVA1 was applied to one of the main surfaces of TAC1 using a bar coater to obtain a coating film. This coating film was dried at 120°C for 5 minutes. In this manner, a first optical substrate having a first coating film provided on one of its main surfaces was obtained. Thereafter, a second optical substrate having a second coating film provided on one of its main surfaces was obtained by the same method. The thickness of each of the first and second coating films was 5 ⁇ m.
  • the functional layer forming composition AC1 was applied to a PET (polyethylene terephthalate) film (Purex film, with silicone coating, manufactured by Toyobo Co., Ltd.) using a bar coater to obtain a third coating film.
  • This third coating film was dried at 100°C for 5 minutes, and then the PET film was peeled off to obtain a photochromic adhesive sheet with a thickness of approximately 30 ⁇ m.
  • the obtained photochromic adhesive sheet was sandwiched between the main surface of the first optical substrate on which the first coating film was provided and the main surface of the second optical substrate on which the second coating film was provided, and these were bonded together to obtain a first structure.
  • the first structure was in the form of a rectangular strip. One end of the long side direction of the first structure was not coated with the functional layer forming composition, and was left as an uncoated portion.
  • This first structure was degassed for 16 hours at 40°C and 13 Torr while being held down on all sides to prevent shrinkage, and then heated at 100°C for 6 hours. In this way, a laminate was obtained in which the first optical substrate, the first adhesive layer, the functional layer, the second adhesive layer, and the second optical substrate were laminated in this order.
  • Example 2 First, 160 g of Kuraray Poval (registered trademark) 22-88 (partially saponified product, degree of saponification: 88 mol%, number average molecular weight: 84900, degree of polymerization: 1893) manufactured by Kuraray Co., Ltd. was added to a 2 L reaction vessel, and mixed with 1440 g of distilled water to obtain a mixture. This mixture was heated and stirred at 95°C for 2 hours to obtain an adhesive composition with a solid content concentration of 10 mass%. Hereinafter, this adhesive composition is also referred to as adhesive composition PVA2. The number average molecular weight of Kuraray Poval 22-88 was measured in the same manner as in Example 1.
  • a laminate was obtained in the same manner as in Example 1, except that adhesive composition PVA2 was used instead of adhesive composition PVA1.
  • Example 3 First, a TAC film having a thickness of 60 ⁇ m that had not been subjected to a saponification treatment was prepared as film TAC2. The contact angle of this film TAC2 with pure water was 60°.
  • a laminate was obtained in the same manner as in Example 1, except that film TAC2 was used instead of film TAC1.
  • Example 4 First, 160 g of polyvinyl alcohol (partially saponified product, saponification degree: 78 to 82 mol%, average polymerization degree: 1,500 to 1,800) manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. was added to a 2 L reaction vessel, and mixed with 1,440 g of distilled water to obtain a mixture. This mixture was heated and stirred at 95° C. for 2 hours to obtain an adhesive composition with a solid content concentration of 10 mass %.
  • this adhesive composition is also referred to as adhesive composition PVA3.
  • a laminate was obtained in the same manner as in Example 1, except that adhesive composition PVA3 was used instead of adhesive composition PVA1.
  • Example 5 First, 160 g of vinyl alcohol-vinylamine copolymer resin ULTILOC (registered trademark) 5003 (fully saponified product, number average molecular weight: 58,400) manufactured by Sekisui Chemical Co., Ltd. was added to a 2 L reaction vessel, and mixed with 1,440 g of distilled water to obtain a mixture. This mixture was heated and stirred at 95° C. for 2 hours to obtain an adhesive composition with a solid content concentration of 10 mass %. Hereinafter, this adhesive composition is also referred to as adhesive composition PVA4. The number average molecular weight of ULTILOC 5003 was measured in the same manner as in Example 1.
  • ULTILOC registered trademark
  • a laminate was obtained in the same manner as in Example 1, except that adhesive composition PVA4 was used instead of adhesive composition PVA1.
  • Example 6 (Production of first prepolymer FPP1) First, a first prepolymer FPP1 was obtained in the same manner as in Example 1.
  • the reaction liquid containing the polymerization component SPP2 containing the first polymer and the second prepolymer had a solid content concentration of 37.2 mass %.
  • a laminate was obtained in the same manner as in Example 1, except that SPP2 was used as the polymerization component containing the first polymer and the second prepolymer instead of the second prepolymer SPP1.
  • composition for forming an adhesive layer is also referred to as composition for forming an adhesive layer EP1.
  • a laminate was obtained in the same manner as in Example 1, except that adhesive composition EP1 was used instead of adhesive composition PVA1.
  • Example 2 Except for omitting the use of the adhesive composition PVA1, a laminate was obtained in the same manner as in Example 1. In this laminate, a first optical substrate, a functional layer, and a second optical substrate were laminated in this order.
  • a saponified TAC film having a thickness of 130 ⁇ m was prepared as film TAC3.
  • the contact angle of pure water on this film TAC3 was 50°.
  • a laminate was obtained in the same manner as in Comparative Example 2, except that film TAC3 was used instead of film TAC1.
  • a TAC film having a thickness of 130 ⁇ m that had not been subjected to a saponification treatment was prepared as film TAC4.
  • the contact angle of this film TAC4 with pure water was 50°.
  • a laminate was obtained in the same manner as in Comparative Example 2, except that film TAC4 was used instead of film TAC1.
  • ⁇ Evaluation test> Measurement of photochromic properties of laminate
  • the maximum absorption wavelength, color density, fading rate, and durability of the resulting laminate were measured.
  • one side of the laminate was irradiated with a xenon lamp L-2480 (300 W) SHL-100 manufactured by Hamamatsu Photonics Co., Ltd. through an Aeromass filter (manufactured by Corning) for 120 seconds at a temperature of 23° C. to cause the photochromic compound to develop color.
  • the beam intensity was 2.4 mW/cm 2 at 365 nm and 24 ⁇ W/cm 2 at 245 nm.
  • the maximum absorption wavelength ( ⁇ max) after color development was determined using a spectrophotometer (Instant Multichannel PhotoDirector MCPD1000) manufactured by Otsuka Electronics Co., Ltd.
  • the absorbance ⁇ (0) of the maximum absorption wavelength of the laminate was measured when not irradiated with the xenon lamp.
  • the laminate was irradiated with the xenon lamp for 120 seconds at the above beam intensity, and the absorbance ⁇ (120) of the maximum absorption wavelength of the laminate was measured.
  • the value obtained by subtracting ⁇ (0) from absorbance ⁇ (120) was taken as the color density. It can be said that the higher this value, the better the photochromic properties.
  • the following accelerated deterioration test was conducted to evaluate the durability of the color development due to light exposure. That is, the obtained laminate was subjected to accelerated deterioration for 96 hours using a Xenon Weather Meter X25 manufactured by Suga Test Instruments Co., Ltd.
  • the color development density was then evaluated before and after the test as described above, and the color development density before the test (A0) and the color development density after the test (A96) were measured.
  • the value of [(A96)/A0] x 100] was taken as the residual rate (durability) (%), which was used as an index of color development durability. The higher the residual rate, the higher the color development durability.
  • the results are shown in Table 1.
  • the laminate was subjected to peel strength evaluation by the following method. Specifically, the optical laminate sheet was cut into a strip of 10 mm x 100 mm to obtain a test piece. At this time, it was cut out so as to include one long side end that does not include the functional layer.
  • the parts of the first optical substrate and the second optical substrate of this test piece where the functional layer is not formed were sandwiched between an upper jig and a lower jig, respectively, and installed on a test machine: Autograph AGS-500NX, manufactured by Shimadzu Corporation. The upper jig was pulled at a crosshead speed of 100 mm/min, and the maximum peel force was measured. This maximum peel force was listed in Table 1 as the peel strength.
  • a first optical substrate having a first major surface and a second major surface
  • a second optical substrate having a first major surface and a second major surface
  • a functional layer located between the first optical substrate and the second optical substrate, the functional layer including a functional dye and a resin
  • a first adhesive layer that bonds the first optical substrate and the functional layer
  • a second adhesive layer that bonds the second optical substrate and the functional layer, A laminate, wherein at least one of the first adhesive layer and the second adhesive layer contains at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resins and modified polyvinyl alcohol resins.
  • At least one of the first adhesive layer and the second adhesive layer contains at least one polyvinyl resin selected from the group consisting of polyvinyl alcohol resin, polyvinyl butyral resin, acetoacetylated polyvinyl alcohol resin, and amine-functional polyvinyl alcohol resin.
  • polyvinyl resin selected from the group consisting of polyvinyl alcohol resin, polyvinyl butyral resin, acetoacetylated polyvinyl alcohol resin, and amine-functional polyvinyl alcohol resin.
  • the functional layer contains at least one resin selected from the group consisting of a polyurethane resin, a polyurethane urea resin, a polythiourethane resin, and a polythiourethane urea resin.
  • a coating layer covering at least a portion of the first optical substrate and the second optical substrate, the coating layer including at least one resin selected from the group consisting of an epoxy resin, an oxetane resin, an acrylic resin, a methacrylic resin, and a urethane resin.
  • a window film comprising the laminate according to any one of [1] to [9].

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