Lenses and glasses

Abstract

To provide an aqueous primer composition for optical articles, which is capable of absorbing light of specific wavelengths and imposes less environmental load, and to provide optical laminates comprising a cured product of the same, optical articles, lenses, and spectacles.SOLUTION: An embodiment of the present invention provides an aqueous primer composition for optical articles. The aqueous primer composition for optical articles includes: at least one compound selected from a group consisting of urethane acrylates, acrylate monomers, acrylic resins, urethane resins, and ester resins; a water-soluble functional pigment; and water.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to an aqueous primer composition for optical articles, an optical laminate, an optical article, a lens, and glasses.

Background Art

[0002] Glasses are optical articles used for correcting refractive abnormalities and protecting the eyes. A functional layer may be laminated on the surface of a plastic lens or a glass lens used for glasses in order to provide functions other than the above-mentioned purposes. For example, a hard coat layer is a functional layer for protecting the lens surface from scratches and the like. A photochromic layer is a functional layer for imparting photochromism to the lens.

[0003] In order to improve the adhesiveness between the functional layer and the lens, a primer layer may be provided therebetween. The primer layer is formed by applying a primer composition on the lens surface and curing the obtained coating film. The primer composition contains, for example, an adhesive component such as a urethane resin and a solvent for dispersing the adhesive component.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide an aqueous primer composition for optical articles having an ability to absorb light of a specific wavelength and having a small environmental load, and an optical laminate, an optical article, a lens, and glasses including a cured product of the aqueous primer composition for optical articles.

Means for Solving the Problems

[0006] According to an embodiment, an aqueous primer composition for an optical article is provided. This aqueous primer composition for an optical article contains at least one compound selected from the group consisting of a urethane acrylate, an acrylic monomer, an acrylic resin, a urethane resin, and an ester resin, a water-soluble functional dye, and water.

[0007] According to an embodiment, an optical laminate is provided. The optical laminate includes an optical substrate, a primer layer, and a resin layer. The primer layer is provided on at least one main surface of the optical substrate and contains a cured product of the aqueous primer composition for an optical article according to the embodiment. The resin layer is provided on the surface of the primer layer opposite to the surface in contact with the optical substrate, and contains at least one resin selected from the group consisting of a (meth)acrylic resin, a urethane resin, a urethane urea resin, and a resin having a siloxane bond.

[0008] According to an embodiment, an optical article including the optical laminate according to the embodiment is provided.

[0009] According to an embodiment, a lens is provided. This lens includes the optical laminate according to the embodiment in which the optical substrate is a plastic lens substrate.

[0010] According to an embodiment, a lens is provided. This lens contains at least one polymer selected from the group consisting of a urethane acrylate and a urethane resin and a water-soluble functional dye.

[0011] According to an embodiment, glasses including the lens according to the embodiment are provided.

Advantages of the Invention

[0012] According to the present invention, an aqueous primer composition for an optical article having the ability to absorb light of a specific wavelength and having a small environmental load, an optical laminate including a cured product of this aqueous primer composition for an optical article, an optical article, a lens, and glasses are provided.

Brief Description of the Drawings

[0013]

Figure 1

Figure 2

Embodiments for Carrying Out the Invention

[0014] The aqueous primer composition for an optical article according to the embodiment contains at least one compound selected from the group consisting of urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin, a water-soluble functional dye, and water.

[0015] Since the primer composition according to the embodiment contains a water-soluble functional dye, a primer layer capable of absorbing light of a specific wavelength such as ultraviolet light or blue light can be formed. Further, since a water-soluble functional dye is used, water can be used as a dispersion medium. Therefore, this primer composition has lower toxicity and a smaller environmental load compared to a primer composition using an organic solvent as a dispersion medium. Also, it is less likely to cause cracks or the like in a plastic lens and can be applied regardless of the type of plastic lens.

[0016] Hereinafter, the photocurable composition according to the embodiment will be described in detail.

[0017] [Aqueous Primer Composition for Optical Articles] (1) Adhesive Component At least one compound selected from the group consisting of urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin is the main component that provides adhesiveness to the primer layer. Among these compounds, from the viewpoint of enhancing weather resistance adhesion, it is preferable to use urethane acrylate.

[0018] The proportion of the above compound in the aqueous primer composition for an optical article is, for example, 5% by mass or more and 70% by mass or less, preferably 20% by mass or more and 50% by mass or less. When this proportion is high, the film thickness becomes thick during coating, so it tends to be difficult to obtain a primer layer with a uniform film thickness. When this proportion is low, the film thickness is too thin during coating, so it tends to be difficult to obtain a primer layer having sufficient light absorption ability. This proportion can be calculated, for example, by a known method for measuring the solid content concentration.

[0019] These compounds are preferably in particulate form, more preferably in the form of colloidal particles. The average particle diameter of the above compound by the light scattering method is, for example, 0.001 μm or more and 0.100 μm or less, preferably 0.005 μm or more and 0.050 μm or less.

[0020] The number average molecular weight of these compounds is preferably 1,000 or more and 100,000 or less. When the number average molecular weight is large, it is possible to form a primer film with good adhesion and toughness, but the viscosity is high and it tends to be difficult to obtain a primer layer with a uniform film thickness. When the average molecular weight is small, the adhesion tends to be insufficient. This average molecular weight can be measured, for example, by the dynamic light scattering method using a ZetaSizer Nano ZS manufactured by Malvern Panalytical.

[0021] These compounds preferably have an anionic group. Having an anionic group increases the dispersibility in an aqueous solvent. Specific examples of the anionic group include a carboxyl group, a sulfonyl group, a phosphate group, and a betaine structure-containing group such as sulfobetaine. The number of anionic groups in one molecule of the compound is preferably 1 or more.

[0022] (1-1) Urethane acrylate Urethane acrylate is an oligomer having a polyurethane skeleton and having a (meth)acryloyl group at the end of the main chain. The (meth)acryloyl group includes at least one of an acryloyl group and a methacryloyl group. The number of (meth)acryloyl groups in urethane acrylate is preferably 2 or more per molecule, and more preferably 4 to 30.

[0023] (1-2) Acrylic monomer An acrylic monomer is a monomer that forms a (meth)acrylic resin by polymerization. The acrylic monomer has one or more (meth)acryloyl groups. The acrylic monomer preferably has 2 or more (meth)acryloyl groups per molecule in the acrylic monomer. Here, the (meth)acryloyl group means at least one of an acryloyl group and a methacryloyl group.

[0024] (1-3) Acrylic resin An acrylic resin is a polymer of an acrylic monomer. The acrylic resin is preferably obtained by emulsion polymerization of an acrylate monomer with an emulsifier.

[0025] (1-4) Urethane resin A urethane resin is a polymer having a urethane bond in the main chain of the molecule. The urethane resin is preferably a reaction product of a polyisocyanate and a polyol. As the polyol, it is preferable to use at least one selected from the group consisting of polyalkylene glycol, polyester polyol, polyether polyol, polyether-ester polyol, and polycarbonate polyol. The polyisocyanate may be an aromatic polyisocyanate or an aliphatic polyisocyanate. The polyisocyanate is preferably an aliphatic polyisocyanate.

[0026] (1-5) Ester resin An ester resin is a polymer having an ester bond in the main chain of the molecule. The ester resin is preferably a resin produced by polycondensation of a polybasic acid and a polyhydric alcohol and does not contain a urethane bond (-NHCOO-) in the molecule.

[0027] (2) Water-soluble functional pigment A functional pigment is a pigment that absorbs light of a specific wavelength. Functional pigments include ultraviolet absorbers, blue light absorbers, dyes, near-infrared absorbers, and infrared absorbers. The functional pigment may be only one type or may contain a mixture of multiple types. A water-soluble functional pigment is a pigment that can be dissolved when 0.5 g of the water-soluble functional pigment is added to 100 g of water and stirred at 20 °C for 3 hours. The water-soluble functional pigment preferably contains at least one of a water-soluble ultraviolet absorber and a water-soluble blue light absorber.

[0028] In the aqueous primer composition for an optical article, the proportion of the water-soluble functional pigment is, for example, 0.01% by mass or more and 20% by mass or less, preferably 0.1% by mass or more and 10% by mass or less, and more preferably 0.3% by mass or more and 7% by mass or less. Also, in the solid matter of the aqueous primer composition for an optical article, the proportion of the water-soluble functional pigment is 1% by mass or more and 50% by mass or less, preferably 5% by mass or more and 30% by mass or less.

[0029] The water-soluble functional pigment preferably has a hydrophilic group. Examples of the hydrophilic group include a hydroxyl group, a sulfo group, an amino group, and a carboxyl group. The water-soluble functional pigment may have one hydrophilic group in one molecule or may have two or more hydrophilic groups.

[0030] (2-1) Water-soluble ultraviolet absorber Water-soluble ultraviolet absorbers exhibit a maximum absorption peak in the wavelength range of 250 nm or more and less than 420 nm. The maximum absorption peak of the water-soluble ultraviolet absorber can be confirmed by visible-ultraviolet spectroscopy (UV-Vis). Specifically, first, an aqueous solution of the water-soluble ultraviolet absorber at a concentration of 0.01 mmol / L is prepared. For this aqueous solution, an absorption spectrum is measured using a UV-Vis spectrophotometer with a 1-cm quartz cell.

[0031] In the aqueous primer composition for an optical article, the proportion occupied by the water-soluble ultraviolet absorber is, for example, 0.01% by mass or more and 20% by mass or less, preferably 0.1% by mass or more and 10% by mass or less, and more preferably 0.5% by mass or more and 5% by mass or less.

[0032] Examples of the water-soluble ultraviolet absorber include pyrimidine derivatives having a hydrophilic functional group, benzophenone derivatives, benzimidazole derivatives, etc. More specifically, a pyrimidine derivative represented by the following formula (1), methylovanamine represented by the following formula (2), a benzophenone derivative represented by the following formula (3), sodium hydroxymethoxybenzophenone sulfonate represented by the following formula (4), and COMFOGUARD UV002 manufactured by Fuji Film Co., Ltd. can be used.

[0033]

Chemical formula

[0034] In the above formula (I), R 1 , R 2 , and R 3 each independently represent hydrogen, a methyl group, or an ethyl group.

[0035]

Chemical formula

[0036]

Chemical formula

[0037] [Chemical formula]

[0038] When an aqueous primer composition for an optical article containing a water-soluble ultraviolet absorber is used, the weather resistance adhesion of the optical laminate can be improved.

[0039] (2-2) Water-soluble blue light absorber The water-soluble blue light absorber exhibits a maximum absorption peak in the wavelength range of 420 nm or more and 500 nm or less. The maximum absorption peak of the water-soluble blue light absorber can be confirmed by UV-Vis spectroscopy. Specifically, first, an aqueous solution of the water-soluble blue light absorber at 0.01 mmol / L is prepared. For this aqueous solution, an absorption spectrum is measured with a UV-Vis spectrophotometer using a 1 cm quartz cell.

[0040] In the aqueous primer composition for an optical article, the proportion occupied by the water-soluble ultraviolet absorber is, for example, 0.01% by mass or more and 20% by mass or less, preferably 0.1% by mass or more and 10% by mass or less, and more preferably 0.5% by mass or more and 5% by mass or less.

[0041] The water-soluble blue light absorber preferably has a maximum absorption peak in the wavelength range of 420 nm or more and 480 nm or less.

[0042] Examples of the water-soluble blue light absorber include COMFOGUARD VIS-001 manufactured by Fuji Film Co., Ltd.

[0043] (3) Water Water is the dispersion medium of the aqueous primer composition for an optical article. Since the aqueous primer composition according to the embodiment uses water as the dispersion medium, a primer composition with high safety and low environmental impact can be realized as compared with those using an organic solvent as the dispersion medium.

[0044] In the aqueous primer composition for optical articles, the proportion of water is, for example, 20% by mass or more and 95% by mass or less, preferably 30% by mass or more and 80% by mass or less. When the proportion of water is high, it tends to be difficult to impart the desired light absorption ability because the film thickness is too thin during coating. When the proportion of water is low, the viscosity of the primer composition increases, and it tends to be difficult to form a primer layer with a uniform film thickness. This proportion can be measured, for example, by gas chromatography.

[0045] (4) Other additives The aqueous primer composition for optical articles may contain other additives in addition to the above-described compounds. Examples of other additives include photopolymerization initiators, neutralizing agents, and organic solvents.

[0046] (4-1) Photopolymerization initiator When using photopolymerizable monomers such as urethane acrylate and acrylic monomer, the primer composition may contain a photopolymerization initiator. The proportion of the photopolymerization initiator in the primer composition is, for example, 0.01 part by mass or more and 5.0 parts by mass or less, preferably 0.05 part by mass or more and 2.0 parts by mass or less, based on 100 parts by mass of the polymerizable monomer. When the proportion of the photopolymerization initiator is high, the resulting primer layer tends to become hard and sufficient adhesion cannot be obtained. When the proportion of the photopolymerization initiator is low, the curing of the resulting primer layer becomes insufficient, and sufficient hardness and adhesion cannot be obtained.

[0047] Specific examples of the photoinitiator include benzophenone; acetophenone compounds such as 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one; α-dicarbonyl compounds such as 1,2-diphenylethanedione and methyl phenylglycoxylate; acylphosphine oxide compounds such as 2,6-dimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphinic acid methyl ester, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide; and 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzoyloxime)], oxy-phenyl-acetic acid 2-[2-oxo-2-phenyl-acetoxy-ethoxy]-ethyl ester, oxy-phenyl-acetic acid 2-[2-hydroxy-ethoxy]-ethyl ester, etc.

[0048] Among these photoinitiators, it is preferable to use liquid or water-soluble photoinitiators. Specific examples of the liquid or water-soluble photoinitiators include 2-hydroxy-2-methyl-1-phenylpropan-1-one (DAROCUR 1173 manufactured by BASF), a mixture of 1-hydroxycyclohexyl phenyl ketone and benzophenone (IRGACURE 500 manufactured by BASF), a mixture of oxy-phenyl-acetic acid 2-[2-oxo-2-phenyl-acetoxy-ethoxy]-ethyl ester and oxy-phenyl-acetic acid 2-[2-hydroxy-ethoxy]-ethyl ester (IRGACURE 754 manufactured by BASF), an aqueous dispersion of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (IRGACURE 819DW manufactured by BASF), a mixture of 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-1-phenylpropan-1-one (DAROCUR 4265 manufactured by BASF), and the like.

[0049] These photoinitiators may be used alone or in combination of two or more. It is also possible to use a known polymerization accelerator such as a tertiary amine in combination.

[0050] (5-1) Neutralizing Agent The neutralizing agent can be formulated to disperse at least one compound selected from the group consisting of the above urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin.

[0051] Examples of the neutralizing agent include trialkylamines such as trimethylamine and triethylamine; N,N-dialkylalkanolamines such as N,N-dimethylethanolamine; trialkanolamines such as triethanolamine; sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonia, trimethylammonium hydroxide, and the like.

[0052] (5-2) Organic Solvent The organic solvent is blended, for example, to disperse at least one compound selected from the group consisting of the above urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin.

[0053] Examples of the organic solvent include alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, t-butanol, 2-butanol; ethers such as ethylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dioxane; ketones such as diacetone alcohol, and the like.

[0054] In the process of manufacturing the primer layer, considering the occurrence of cracks in the optical substrate and high safety, etc., the proportion of the organic solvent in the primer composition is preferably low. The proportion of the organic solvent in the aqueous primer composition for optical articles is preferably 30% by mass or less, more preferably 20% by mass or less. The lower limit value of the proportion of the organic solvent is 0% by mass.

[0055] (6) Method for producing an aqueous primer composition for optical articles The aqueous primer composition for optical articles can be produced, for example, by the following method. First, prepare each raw material. As the raw material of at least one compound selected from the group consisting of urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin, it is preferable to use a dispersion of each compound. The dispersion of each compound may contain each compound particle, a solvent, and a neutralizing agent. As the solvent, it is preferable to use water. As the neutralizing agent, those described above are used. In the dispersion of the compound particles, the proportion occupied by the solid content is preferably 10% by mass or more and 80% by mass or less. That is, the primer composition for an optical article according to the embodiment may contain a dispersion of at least one compound selected from the group consisting of urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin, a water-soluble functional dye, and any other additives.

[0056] Next, mix the prepared raw materials, for example, at normal pressure and normal temperature to obtain a photocurable composition. The order of mixing the prepared raw materials is not particularly limited.

[0057] Since the aqueous primer composition for an optical article obtained by the above method contains a water-soluble functional dye, when this primer composition is used, a primer layer with high safety and functionality can be obtained.

[0058] As the raw material of the aqueous primer composition for an optical article, it is preferable to use at least one of a dispersion of urethane acrylate and a dispersion of urethane resin. Hereinafter, the dispersion of urethane acrylate and the dispersion of urethane resin will be described in detail.

[0059] In the dispersion of urethane acrylate, the amount of the solid content is preferably 10 to 70% by mass, and more preferably 20 to 50% by mass.

[0060] As the dispersion of urethane acrylate, Ucecoat (registered trademark) manufactured by Daicel Ornex Co., Ltd. can be preferably used.

[0061] As the urethane acrylate dispersion, it is preferable to use one in which the elongation rate at 25°C of the cured product of urethane acrylate is 0.1% or more and 10% or less. When using a primer composition containing such urethane acrylate, a cured product highly crosslinked three-dimensionally can be obtained. The elongation rate at 25°C of the cured product is more preferably 0.5% or more and 5.0% or less. Further, the tensile strength at 25°C of the cured product of urethane acrylate is preferably 10 MPa or more and 50 MPa or less, and more preferably 15 MPa or more and 30 MPa or less.

[0062] The elongation rate and tensile strength of the cured product of the water-dispersible urethane (meth) acrylate alone can be measured by the following method. First, 2-hydroxy-2-methyl-1-phenylpropan-1-one, which is a photopolymerization initiator, is added to the dispersion of urethane (meth) acrylate so as to be 0.3 parts by mass with respect to 100 parts by mass of the solid content to obtain a mixed solution. This mixed solution is separately placed in a container such as a petri dish so that the film thickness of the solid content after drying becomes about 500 μm. The separated mixture is allowed to stand in the dark at room temperature for 24 hours, further allowed to stand in the dark at 80°C for 6 hours, and further allowed to stand in the dark at 120°C for 20 minutes to be sufficiently dried to obtain a residue. This residue is irradiated with light for 90 seconds in a nitrogen gas atmosphere so that the output at 405 nm becomes 2 200 mW / cm to obtain a film. When performing light irradiation, for example, F3000SQ equipped with a D bulb manufactured by Fusion UV Systems is used. After cutting the obtained film into a size of 15 mm in width and 200 mm in length, punctuation marks are marked at 50 mm intervals in the central part to prepare a measurement sample. This measurement sample is attached to a tensile tester, the gripping interval of the tester is set to 100 mm, and the elongation rate is measured by pulling the sample at a speed of 200 mm / min until it breaks. The stress at the moment when the sample breaks is defined as the tensile strength, and the elongation rate is obtained by the following formula.

[0063] Elongation rate (%) = ((distance between punctuation marks at break - distance between punctuation marks before test) / (distance between punctuation marks before test)) × 100.

[0064] The urethane acrylate contained in the dispersion of urethane acrylate can be obtained, for example, by reacting a polyisocyanate compound, a polyol compound, an anionic group active hydrogen group-containing compound, and a hydroxyl group-containing (meth)acrylate compound.

[0065] Specific examples of the polyisocyanate compound include aliphatic diisocyanate compounds such as tetramethylene-1,4-diisocyanate, hexamethylene-1,6-diisocyanate, octamethylene-1,8-diisocyanate, 2,2,4-trimethylhexane-1,6-diisocyanate; alicyclic diisocyanate compounds such as cyclobutane-1,3-diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate, 2,4-methylcyclohexyl diisocyanate, 2,6-methylcyclohexyl diisocyanate, isophorone diisocyanate, norbornene diisocyanate, isomer mixture of 4,4'-methylenebis(cyclohexyl isocyanate), hexahydrotoluene-2,4-diisocyanate, hexahydrotoluene-2,6-diisocyanate, hexahydrophenylene-1,3-diisocyanate, hexahydrophenylene-1,4-diisocyanate, 1,9-diisocyanato-5-methylnonane, 1,1-bis(isocyanatomethyl)cyclohexane, 2-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]-1-methylcyclohexane, 2-(3-isocyanatopropyl)cyclohexyl isocyanate, norbornane diisocyanate;Aromatic diisocyanate compounds such as phenylcyclohexylmethane diisocyanate, an isomer mixture of 4,4'-methylenebis(phenyl isocyanate), toluene-2,3-diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, phenylene-1,3-diisocyanate, phenylene-1,4-diisocyanate, 1,3-bis(isocyanatomethyl)benzene, xylylene diisocyanate, tetramethylxylylene diisocyanate, naphthalene diisocyanate, diphenyl ether diisocyanate, 1,3-diisocyanatomethylbenzene, 4,4'-diisocyanato-3,3'-dimethoxy(1,1'-biphenyl), 4,4'-diisocyanato-3,3'-dimethylbiphenyl, 1,2-diisocyanatobenzene, 1,4-bis(isocyanatomethyl)-2,3,5,6-tetrachlorobenzene, 2-dodecyl-1,3-diisocyanatobenzene, 1-isocyanato-4-[(2-isocyanatocyclohexyl)methyl]2-methylbenzene, 1-isocyanato-3-[(4-isocyanatophenyl)methyl)-2-methylbenzene, 4-[(2-isocyanatophenyl)oxy]phenyl isocyanate, diphenylmethane diisocyanate, etc. are included.;

[0066] Furthermore, multimers of the above polyisocyanate compounds (for example, dimers, trimers, etc.); biuret modified products produced by the reaction of multimers of polyisocyanate compounds with water; allophanate modified products and polyol modified products produced by the reaction of multimers of polyisocyanate compounds with alcohols or low molecular weight polyols described later; oxadiazinetrione modified products produced by the reaction of multimers of polyisocyanate compounds with carbon dioxide gas, and multimers of these modified products, etc. can also be used as raw materials for the water-dispersible urethane (meth)acrylate of the present invention. These polyisocyanate compounds can be used alone or in combination of two or more polyisocyanate compounds.

[0067] Among the above polyisocyanate compounds, it is preferable to use an aliphatic diisocyanate compound and / or an alicyclic diisocyanate compound from the viewpoint of weather resistance.

[0068] Specific examples of the polyol compound include alkylene glycols such as ethylene glycol, 1,2-propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, dipropylene glycol, and diethylene glycol; polyalkylene glycols such as polypropylene glycol, polyethylene glycol, and polytetramethylene glycol; poly(alkylene adipate) such as poly(diethylene adipate), poly(tetramethylene adipate), poly(hexamethylene adipate), and poly(neopentylene adipate); polycaprolactone polyols such as poly-ε-caprolactone, polycaprolactone diol, and polycaprolactone triol; polybutadiene glycols such as poly(1,4-butadiene) glycol and poly(1,2-butadiene) glycol; poly(alkylene carbonate) such as poly(hexamethylene carbonate); polyester polyols; polyols containing three or more hydroxy groups in one molecule such as trimethylolethane, trimethylolpropane, 1,2,4-butanetriol, 1,2,6-hexanetriol, and pentaerythritol; silicone polyol, and the like. These polyol compounds can be used alone or in combination of two or more polyol compounds.

[0069] Among these polyol compounds, polyalkylene glycols, polyols containing three or more hydroxy groups, polyalkylene adipates, polyalkylene carbonate polyols, polycaprolactone polyols, and polyester polyols are preferable because the heating temperature during curing can be made lower and the thermal deformation and discoloration of the base material can be more reliably prevented.

[0070] The anionic group and active hydrogen group-containing compound is a compound having one or more anionic groups such as a carboxyl group, a sulfonyl group, a phosphate group, a betaine structure-containing group such as a sulfobetaine, and having two or more active hydrogen groups capable of reacting with an isocyanate group. Specific examples of such an anionic group and active hydrogen group-containing compound include dihydroxycarboxylic acids such as 2,2-dimethylolacetic acid, 2,2-dimethylollactic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolvaleric acid, and diamino carboxylic acids such as lysine, cystine, and arginine.

[0071] The hydroxyl group-containing (meth)acrylate compound is a (meth)acrylate compound having one or more hydroxyl groups in the molecule. Specific examples of such a hydroxyl group-containing (meth)acrylate compound include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2,2-dihydroxymethylbutyl (meth)acrylate, hydroxyhexyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 1,4-butylene glycol mono(meth)acrylate, glycerin mono(meth)acrylate, propylene glycol mono(meth)acrylate, polycaprolactone glycol mono(meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, polyhydroxyalkyl maleate, polyhydroxyalkyl fumarate, and the like.

[0072] The blending amount of each of the above components when producing urethane acrylate may be appropriately determined according to the target structure. From the viewpoint of easily obtaining urethane acrylate, the total equivalent of isocyanate groups of the polyisocyanate compound is 0.95 to 2.0 equivalents, particularly preferably 1.0 to 1.5 equivalents, relative to the total equivalent of hydroxyl groups contained in the polyol compound, hydroxyl groups contained in the anionic group active hydrogen group-containing compound, active hydrogen groups such as amino groups, and hydroxyl groups contained in the hydroxyl group-containing (meth)acrylate compound.

[0073] In addition, when the total equivalent of isocyanate groups of the polyisocyanate compound exceeds 1.0 relative to the total equivalent of hydroxyl groups contained in the polyol compound, hydroxyl groups contained in the anionic group active hydrogen group-containing compound, active hydrogen groups such as amino groups, and hydroxyl groups contained in the hydroxyl group-containing (meth)acrylate compound, chain extension can be carried out using a chain extender after water dispersion. As the chain extender, a known chain extender can be used. Specifically, such chain extenders include water, short-chain diols such as ethylene glycol and 1,4-butanediol, and polyamines such as hydrazine, ethylenediamine, diethyltriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, propylenediamine, hexamethylenediamine, cyclohexylenediamine, piperazine, 2-methylpiperazine, phenylenediamine, tolylenediamine, xylenediamine, α,α'-methylenebis(2-chloroaniline), 3,3'-dichloro-α,α'-biphenylamine, m-xylenediamine, isophoronediamine, and N-methyl-3,3'-diaminopropylamine.

[0074] The aqueous dispersion of urethane acrylate is obtained by mixing the above urethane acrylate and a neutralizing agent and dispersing them in water, and is in the form of an emulsion, dispersion, colloidal dispersion, etc. of urethane acrylate.

[0075] The urethane resin contained in the urethane resin dispersion is preferably a water-dispersible polyurethane resin obtained by reacting a polyol compound, an anionic group and active hydrogen group-containing compound, and a polyisocyanate compound.

[0076] More preferably, a water-dispersible polyurethane resin described in Japanese Patent No. 5016266, International Publication No. WO2008 / 001875 pamphlet, etc., which is obtained by reacting an active hydrogen group-containing acrylate compound and / or an alkoxysilyl group-containing polyamine compound, is mixed.

[0077] As the polyol compound, anionic group and active hydrogen group-containing compound, polyisocyanate compound, and hydroxyl group-containing (meth)acrylate compound, which are the raw materials of the above water-dispersible polyurethane resin, those similar to the raw materials of the aforementioned water-dispersible urethane (meth)acrylate can be used. Examples of the alkoxysilyl group-containing polyamine compound include alkoxysilyl compounds having a primary amino group and a secondary amino group. Specifically, N-β(aminoethyl)-γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)-γ-aminopropyltrimethoxysilane, γ-(2-aminoethyl)aminopropyltriethoxysilane, γ-(2-aminoethyl)aminopropyldimethoxysilane, γ-(2-aminoethyl aminopropyldiethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyldimethoxysilane, γ-aminopropyldiethoxysilane, N,N'-bis[α-(trimethoxysilyl)propyl]ethylenediamine, etc. can be mentioned.

[0078] The water-dispersible urethane resin can be synthesized by reacting an active hydrogen group-containing component (i.e., at least a polyol compound, an anionic group active hydrogen group-containing compound, a hydroxyl group-containing (meth)acrylate compound, and / or an alkoxysilyl group-containing polyamine compound) with a polyisocyanate component (i.e., a polyisocyanate compound) in the same manner as the water-dispersible urethane (meth)acrylate by a one-shot method, a prepolymer method, etc., and the prepolymer method is more preferable. A chain extender can also be used.

[0079] The surface hardness of the urethane resin layer obtained by photocuring the water-dispersible polyurethane resin is equivalent to that without photocuring, and no improvement effect of surface hardness by photocuring is recognized.

[0080] Among the above water-dispersible urethane resins, from the viewpoints of the appearance and adhesion of the photochromic laminate, the tensile strength at 25°C of the urethane resin film obtained by drying the water-dispersible urethane resin is 20 MPa or more and 70 MPa or less, particularly 30 MPa or more and 60 MPa or less, and the elongation at 25°C is 100% or more and 1000% or less, particularly 200% or more and 800% or less. A water-dispersible urethane resin is preferably used. The tensile strength and elongation of the urethane resin film of the water-dispersible urethane resin can be measured in the same manner as urethane acrylate.

[0081] Also, among the water-dispersible urethane resins, from the viewpoints of improving the appearance and adhesion of the obtained photochromic laminate, the Vickers hardness of the dried film of the water-dispersible urethane resin is preferably 1 or more and less than 8, particularly 2 or more and 6 or less. The Vickers hardness of the dried film of the water-dispersible urethane resin can also be measured in the same manner as the water-dispersible urethane (meth)acrylate.

[0082] When using the above water-dispersible polyurethane resin, the blending ratio of the water-dispersible polyurethane resin should prevent the decrease in the surface hardness of the resulting primer coat layer and the subsequent decrease in the surface hardness after laminating the photochromic layer. Also, in order to sufficiently obtain the effect of improving adhesion, it is preferable to mix 5 to 200 parts by mass of the water-dispersible urethane resin with respect to 100 parts by mass of the water-dispersible urethane (meth) acrylate, more preferably 10 to 150 parts by mass, and most preferably 30 to 100 parts by mass.

[0083] Also, the water-dispersible urethane resin can be blended as it is, or a water dispersion in which the urethane resin is dispersed in water can also be blended.

[0084] As the dispersion of the water-dispersible urethane resin, Superflex 420 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., NJ-321A manufactured by Tokuyama Corporation, etc. can be preferably used.

[0085] [Optical laminate] The optical laminate according to the embodiment includes an optical substrate, a primer layer provided on at least one main surface of the optical substrate and including a cured body of the aqueous primer composition for an optical article according to the embodiment, and a primer layer provided on a surface opposite to the surface in contact with the optical substrate. And a resin layer containing (meth) acrylic resin, urethane resin, epoxy resin, resin having a siloxane bond, etc.

[0086] Figure 1 is a cross-sectional view schematically showing an example of the optical laminate according to the embodiment. The optical laminate 1 shown in Figure 1 includes an optical substrate 2, a primer layer 3 provided on one main surface of the optical substrate 2, and a resin layer provided on the primer layer 3. The optical substrate 2 has an uneven shape. The primer layer 3 and the resin layer 4 cover the convex side of the optical substrate 2.

[0087] (1) Optical substrate As the optical substrate, any substrate having light transmissivity can be used without particular limitation. Examples of the optical substrate include glass lenses, plastic lenses, glass and resins used for windows of houses or vehicles. Since the aqueous primer composition for an optical article according to the embodiment uses water as a dispersion medium, it is less likely to affect plastics compared to a primer composition using an organic solvent as a dispersion medium. Therefore, the primer composition according to the embodiment is suitable for an optical laminate using a plastic lens as an optical substrate.

[0088] Examples of the plastic lens include thermoplastic resin lenses such as (meth)acrylic resins and polycarbonate-based resins; crosslinkable resin lenses such as polyfunctional (meth)acrylic resins, allyl-based resins, thiourethane-based resins, urethane-based resins, and thioepoxy-based resins, and known ones can be used. As the plastic lens, a methacrylic plastic lens or a thiourethane plastic lens is preferable. That is, the primer layer obtained by the aqueous primer composition for an optical article according to the embodiment is suitable as a primer layer for adhering a resin layer and an optical substrate made of these plastic lenses.

[0089] The shape of the plastic lens substrate is not particularly limited and can be applied to those having known shapes. Examples of the shape of the plastic lens substrate include a minus lens, a plus lens, and an angled lens.

[0090] (2) Primer layer The primer layer contains a cured product of the aqueous primer composition for an optical article according to the embodiment and may be composed of this cured product. The primer layer may be provided on one main surface of the optical substrate or on both main surfaces. The primer layer enhances the adhesiveness between the optical substrate and the resin layer. Further, since the primer layer contains a water-soluble functional dye, it has a function by this functional dye. The function of the primer layer may be the same as or different from that of the resin layer.

[0091] The thickness of the primer layer is, for example, 0.1 μm or more and 10 μm or less.

[0092] The primer layer preferably contains at least one of a water-soluble ultraviolet absorber and a water-soluble blue light absorber. That is, the aqueous primer composition for an optical article according to the embodiment preferably contains at least one of a water-soluble ultraviolet absorber and a water-soluble blue light absorber.

[0093] When a primer layer containing a water-soluble ultraviolet absorber is provided, the weather resistance adhesion of the optical laminate tends to be improved. That is, ultraviolet rays can cause deterioration of the plastic-based optical substrate and the primer layer itself. When the primer layer contains a water-soluble ultraviolet absorber, such ultraviolet rays can be absorbed, so that it becomes difficult for ultraviolet rays to reach the primer layer itself and the optical substrate located inside the ultraviolet irradiation object with respect to the primer layer. In addition, ultraviolet rays can be harmful to the human eye. Therefore, an optical laminate provided with a primer layer containing a water-soluble ultraviolet absorber is suitable as a plastic lens for glasses.

[0094] A primer layer containing a water-soluble blue light absorber can absorb blue light. Blue light is light having strong energy among visible rays and can have an adverse effect on the human eye. Therefore, an optical laminate provided with a primer layer containing a water-soluble blue light absorber is suitable as a lens for glasses having a blue light cut function.

[0095] (3) Resin layer The resin layer contains a resin. The resin layer may contain at least one selected from the group consisting of a functional dye, a silicon compound, a metal compound, and an additive. By containing specific components, the resin layer can have various functions. For example, a resin layer containing a resin, a silicon compound, and a transition metal compound can function as a hard coat layer for protecting an optical substrate from scratches and the like. A resin layer containing a functional dye can absorb light of a specific wavelength. The resin layer is a cured product of a composition for forming a resin layer described later.

[0096] Note that the resin layer may be a single layer or may have a multilayer structure. For example, the resin layer may include a first resin layer provided on a primer layer and containing a photochromic compound, and a second resin layer provided on the first resin layer and functioning as a hard coat layer.

[0097] The resin layer is preferably a photochromic resin layer containing a photochromic compound or a hard coat layer containing a silicon compound. That is, the primer layer obtained from the aqueous primer composition for an optical article according to the embodiment is suitable as a primer layer for adhering a photochromic resin layer or a hard coat layer to an optical substrate.

[0098] (3-1) Resin Examples of the resin contained in the resin layer include (meth)acrylic resins, urethane resins, epoxy resins, and resins having a siloxane bond. Note that the (meth)acrylic resin means at least one of an acrylic resin and a methacrylic resin.

[0099] (3-2) Functional Dye (3-2-1) Photochromic Compound The photochromic compound is a compound that undergoes a reversible structural change upon ultraviolet irradiation. An optical substrate containing a photochromic compound can change from colorless and transparent to a colored state upon ultraviolet irradiation.

[0100] Examples of the photochromic compound include fulgide compounds, chromene compounds, and spirooxazine compounds.

[0101] (3-2-2) Thermochromic Material The thermochromic material is a material that undergoes a reversible structural change with a change in temperature. An optical substrate containing a thermochromic material can change its color due to a change in temperature.

[0102] Examples of the thermochromic material include leuco dyes.

[0103] (3-2-3) Porphyrin compound A porphyrin compound is a compound having a porphyrin skeleton. An optical substrate containing a porphyrin compound can absorb specific wavelengths in the visible light region of 400 to 800 nm.

[0104] Examples of porphyrin compounds include compounds in which Zn 2+ , Cu 2+ , Ni 2+ , Co 2+ etc. are coordinated.

[0105] (3-2-4) Near-infrared absorber A near-infrared absorber is a compound having an absorption peak at a wavelength of 800 nm or more and 2000 nm or less. When an optical substrate containing a near-infrared absorber is used, near-infrared rays contained in sunlight and the like can be efficiently cut.

[0106] Examples of near-infrared absorbers include cyanine dyes, phthalocyanine dyes, nickel dithiolene complexes, squarium dyes, quinone compounds, diimonium compounds, azo compounds, and the like.

[0107] (3-2-5) Blue light absorber A blue light absorber is a compound having an absorption peak at a wavelength of 420 nm or more and 480 nm or less. Blue light can cause glare to the human eye or cause sleep disorders. Glasses using an optical substrate containing a blue light absorber can suppress such blue light from reaching the human eye.

[0108] Examples of blue light absorbers include porphyrin compounds having an absorption peak at a wavelength of 420 nm or more and 480 nm or less.

[0109] (3-2-6) Polarizer A polarizer is an optical element that can extract linearly polarized light from natural light. When using an optical substrate containing a polarizer, the transmittance of reflected light can be reduced. Glasses using an optical substrate containing a polarizer can suppress the reflected light from reaching a person's eyes, thereby reducing glare.

[0110] Examples of polarizers include dichroic substances such as iodine and dichroic dyes. The dichroic substance may be dispersed in a film such as polyvinyl alcohol or polyethylene terephthalate. That is, a polarizing film in which a dichroic substance is dispersed may be used as the resin layer.

[0111] (3-2-7) Ultraviolet absorber The ultraviolet absorber may be a water-soluble ultraviolet absorber, a hydrophobic ultraviolet absorber, or a mixture thereof. When the primer layer contains an ultraviolet absorber, the absorption peak of the ultraviolet absorber contained in the resin layer is preferably different from the absorption peak of the ultraviolet absorber contained in the primer layer. By using such an ultraviolet absorber, an optical laminate capable of cutting a wide range of ultraviolet rays can be obtained. As the water-soluble ultraviolet absorber, the same type as those described in the primer composition can be used.

[0112] Examples of hydrophobic ultraviolet absorbers include benzotriazole-based, benzophenone-based, benzoate-based, triazine-based, etc.

[0113] (3-2-8) Dye The dye is a dye other than the above-described functional pigments. The dye is used to dye the optical substrate in a desired color. Examples of the dye include azo dyes and anthraquinone dyes.

[0114] (3-3) Silicon compound The resin layer containing a silicon compound can function as a hard coat layer. The silicon compound includes an organic silane and silicon dioxide. Examples of the organic silane include γ-glycidoxypropyltrimethoxysilane, tetraethoxysilane, methyltriethoxysilane, etc. The organic silane may be used alone or in combination of multiple types. It is preferable that the silicon compound includes an organic silane and silicon dioxide.

[0115] The proportion of the silicon compound in the resin layer is, for example, 10% by mass or more and 99% by mass or less, preferably 30% by mass or more and 95% by mass or less.

[0116] (3-4) Metal compound The resin layer containing a metal compound can function as a hard coat layer. Examples of the metal compound include oxides of metal elements. As the metal compound, fine particles composed of an inorganic oxide or a composite inorganic oxide containing at least one element selected from Si, Al, Ti, Fe, In, Zr, Au, Sn, Sb, W, and Ce are preferable.

[0117] The proportion of the metal compound in the resin layer is, for example, 5% by mass or more and 80% by mass or less, preferably 10% by mass or more and 60% by mass or less.

[0118] (3-5) Other additives Examples of other additives include a photopolymerization initiator, a leveling agent, and a light stabilizer. As the photopolymerization initiator, the same type as those described in the primer composition can be used.

[0119] (3-5-1) Leveling agent The leveling agent is blended for the purpose of smoothing the resin layer. As the leveling agent, a silicone surfactant having a silicone chain, a fluorine surfactant having a fluorocarbon chain, or the like can be used. Specific examples of the leveling agent include "L-7001", "L-7002", "L-7604", "FZ-2123" manufactured by Toray Dow Corning Co., Ltd., "Megafac F-470", "Megafac F-1405", "Megafac F-479" manufactured by Dainippon Ink and Chemicals, Inc., "Fluorad FC-430" manufactured by Sumitomo 3M Limited, and the like. Only one type of leveling agent may be used, or a plurality of types may be mixed and used.

[0120] The proportion of the leveling agent in the resin layer is, for example, 1 ppm or more and 1000 ppm or less, preferably 10 ppm or more and 500 ppm or less.

[0121] (3-5-2) Light stabilizer As the light stabilizer, a hindered amine light stabilizer, a hindered phenol antioxidant, or a sulfur-based antioxidant can be used. Preferred examples include bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, Adeka Stab LA-52, LA-57, LA-62, LA-63, LA-67, LA-77, LA-82, LA-87 manufactured by Asahi Denka Co., Ltd., 2,6-di-t-butyl-4-methyl-phenol, 2,6-ethylenebis(oxyethylene) bis[3-(5-t-butyl-4-hydroxy-m-tolyl)propionate], IRGANOX 1010, 1035, 1075, 1098, 1135, 1141, 1222, 1330, 1425, 1520, 259, 3114, 3790, 5057, 565 manufactured by Ciba Specialty Chemicals Inc., and the like. Only one type of light stabilizer may be used, or a plurality of types may be mixed and used.

[0122] The proportion of the light stabilizer in the resin layer is, for example, 0.01% by mass or more and 5% by mass or less, preferably 0.05% by mass or more and 3% by mass or less.

[0123] (4) Manufacturing method of the optical laminate The optical laminate can be manufactured, for example, by the following method. First, prepare an optical substrate. In order to enhance the adhesion to the primer layer, chemical treatment such as with an alkaline solution or an acid solution, or physical treatment such as corona discharge, plasma discharge, or polishing may be performed on the surface of the optical substrate.

[0124] Next, apply the aqueous primer composition for an optical article according to the embodiment on this optical substrate, for example, by spin coating to obtain a first coating film. Apply a composition for forming a resin layer on this first coating film, for example, by spin coating to obtain a second coating film. Irradiate the laminate of the first coating film and the second coating film with ultraviolet rays to cure the first and second coating films to obtain an optical laminate. When irradiating with ultraviolet rays, for example, it is performed under a nitrogen atmosphere, the atmosphere temperature is, for example, 10°C or higher and 80°C or lower, and the ultraviolet irradiation time is, for example, 5 seconds or longer and 120 seconds or shorter. The ultraviolet intensity is, at a wavelength of 365 nm, 50 mW / cm 2 or more and 500 mW / cm 2 or less. Alternatively, cure the first and second coating films by heating to obtain an optical laminate. When performing the heat treatment, for example, it is performed under air or a nitrogen atmosphere, the atmosphere temperature is, for example, 70°C or higher and 130°C or lower, and the heating time is, for example, 30 minutes or longer and 3 hours or shorter.

[0125] Note that after forming a primer layer by thermally or photocuring the first coating film, apply a composition for forming a resin layer on this primer layer to form a second coating film, and then cure the second coating film by heat or light to obtain an optical laminate.

[0126] The composition for forming a resin layer contains at least one of a resin and a monomer, and optional components. As the monomer, it is preferable to use an acrylic monomer. When using an acrylic monomer, the resin layer can be cured by ultraviolet irradiation, so an optical laminate can be efficiently manufactured in a short time compared with the case of curing by heat.

[0127] As the acrylic monomer, known (meth)acrylic monomers can be used without particular limitation. Specifically, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, tetramethylolmethane trimethacrylate, tetramethylolmethane triacrylate, tetramethylolmethane tetramethacrylate, tetramethylolmethane tetraacrylate, trimethylolpropane triethylene glycol trimethacrylate, trimethylolpropane triethylene glycol triacrylate, ditrimethylolpropane tetramethacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol hexaacrylate, bisphenol A dimethacrylate, 2,2-bis(4-methacryloyloxyethoxyphenyl)propane, 2,2-bis(4-methacryloyloxypolyethylene glycol phenyl)propane with an average molecular weight of 628, 2,2-bis(4-methacryloyloxypolyethylene glycol phenyl)propane with an average molecular weight of 804, 2,2-bis(4-methacryloyloxypolyethylene glycol phenyl)propane with an average molecular weight of 776, 2,2-bis(4-acryloyloxypolyethylene glycol phenyl) propane, methoxypolyethylene glycol methacrylate with an average molecular weight of 468, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, pentaethylene glycol dimethacrylate, pentapropylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, pentaethylene glycol diacrylate, tripropylene glycol diacrylate, tetrapropylene glycol diacrylate, pentapropylene glycol diacrylate, polyethylene glycol dimethacrylate with an average molecular weight of 330, polyethylene glycol dimethacrylate with an average molecular weight of 536, polytetramethylene glycol dimethacrylate with an average molecular weight of 736, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, polypropylene glycol dimethacrylate with an average molecular weight of 536, polyethylene glycol diacrylate with an average molecular weight of 258, polyethylene glycol diacrylate with an average molecular weight of 308, polyethylene glycol diacrylate with an average molecular weight of 508, polyethylene glycol diacrylate with an average molecular weight of 708, polycarbonate di(meth)acrylate which is a reaction product of polycarbonate diol and (meth)acrylic acid, polyfunctional urethane (meth)acrylates such as urethane oligomer tetraacrylate, urethane oligomer hexamethacrylate, urethane oligomer hexaacrylate, polyfunctional polyester (meth)acrylates such as polyester oligomer hexaacrylate, silsesquioxane monomers having (meth)acrylic groups and various structures such as cage-like, ladder-like, and random, 2-isocyanatoethyl methacrylate, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, glycidyl methacrylate, etc. can be mentioned.,

[0128] In addition, a resin layer-forming composition containing 1) polycarbonate di(meth)acrylate, 2) polyfunctional (meth)acrylates such as trimethylolpropane trimethacrylate and ditrimethylolpropane tetramethacrylate, and 3) di(meth)acrylate having a bisphenol A skeleton such as 2,2-bis[4-(methacryloxy polyethoxy)phenyl]propane (average chain length of ethylene glycol chain is 10 and average molecular weight is 804), or a resin layer-forming composition containing 4) polyfunctional (meth)acrylates such as trimethylolpropane trimethacrylate and ditrimethylolpropane tetramethacrylate, 5) di(meth)acrylate having a bisphenol A skeleton such as 2,2-bis[4-(methacryloxy polyethoxy)phenyl]propane (average chain length of ethylene glycol chain is 10 and average molecular weight is 804), 6) at least one long-chain (meth)acrylic monomer selected from the group consisting of polyalkylene glycol di(meth)acrylate having a molecular weight of 600 to 2000 and urethane di(meth)acrylate having a molecular weight of 600 to 2000 is preferred. Further, when the total of the (meth)acrylate monomers of 1) to 3) is 100% by mass, 1) is 10 to 30% by mass, 2) is 35 to 50% by mass, and 3) is 10 to 65% by mass, or when the total of the (meth)acrylate monomers of 3) to 6) is 100% by mass, 3) is 35 to 70% by mass, 2) is 10 to 40% by mass, and 3) is 10 to 40% by mass is more preferred.

[0129] [Optical article] The optical article includes the optical laminate according to the embodiment. Examples of the optical article include plastic spectacle lenses, spectacles equipped with such lenses, automotive windows, and house windows.

[0130] The lens according to the embodiment contains at least one polymer selected from the group consisting of urethane acrylate, urethane resin, acrylic resin, and epoxy resin, a water-soluble functional dye, and a photoinitiator. Such a lens is considered to include a cured product of the aqueous primer composition for an optical article according to the embodiment. That is, when an ultraviolet absorber is contained in an optical substrate such as a plastic lens or a resin layer covering the optical substrate, a hydrophobic ultraviolet absorber is typically used in view of its compatibility with resins and the like, and a water-soluble ultraviolet absorber is not used. In the composition for forming a primer layer, the proportion of the resin component and the like is low, and since the water-soluble resin component and the like exhibit high adhesiveness, water can be used as the dispersion medium. The primer layer, which is a cured product of such a composition for forming a primer layer, may contain a water-soluble functional dye.

[0131] FIG. 2 is a perspective view schematically showing an example of glasses according to the embodiment. The glasses 10 shown in FIG. 3 include two lenses 11 and a frame 12 for fixing these lenses 11. At least one of the two lenses 11 includes the optical laminate according to the embodiment.

Examples

[0132] Next, the present invention will be described in detail using examples and comparative examples, but the present invention is not limited to these examples.

[0133] <Aqueous primer composition for optical articles> The following materials were used as materials for the aqueous primer composition for optical articles.

[0134] (A: Water-soluble functional dye) A1; Sodium hydroxymethoxybenzophenone sulfonate (a water-soluble dye having a series maximum near 285 nm) A2; Methylcobalamin (a water-soluble functional dye having an absorption maximum near 360 nm) A3; COMFOGUARD UV-002 manufactured by Fuji Film (a water-soluble functional dye having an absorption maximum near 360 nm) (B: Water-soluble blue light absorber) B1; FUJIFILM COMFOGUARD VIS-001 (Water-soluble functional dye having an absorption maximum near 465 nm) (C: Aqueous dispersion of water-dispersible urethane (meth)acrylate) C1; Carboxyl group-containing aqueous dispersion of urethane acrylate (DIC Ornex Co., Ltd.'s "Ucecoat7655", average particle size 150 nm, solid content concentration 35%, tensile strength 25 MPa, elongation 1.5%).

[0135] C2; Carboxyl group-containing aqueous dispersion of urethane acrylate (DIC Ornex Co., Ltd.'s "Ucecoat7849", average particle size 150 nm, solid content concentration 35%, tensile strength 15 MPa, elongation 1.3%).

[0136] C3; Carboxyl group-containing aqueous dispersion of urethane acrylate (DIC Ornex Co., Ltd.'s "Ucecoat7674", average particle size 150 nm, solid content concentration 40%, tensile strength 24 MPa, elongation 18%).

[0137] (D: Photoinitiator) D1; Phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide ("Irgacure819" manufactured by BASF).

[0138] D2; 2-Hydroxy-2-methyl-1-phenylpropan-1-one ("DAROCUR1173" manufactured by BASF) D3; Mixture of 1-hydroxycyclohexyl phenyl ketone and benzophenone (IRGACURE500 manufactured by BASF) D4; Mixture of 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-1-phenylpropan-1-one (DAROCUR4265 manufactured by BASF) (E: Aqueous dispersion of water-dispersible urethane resin) E1; Aqueous dispersion of water-dispersible urethane resin ("Superflex 420" manufactured by Daiichi Kogyo Seiyaku Co., Ltd., solid content concentration 32%, tensile strength 30 MPa, elongation 280%).

[0139] E2; A water-dispersible urethane resin dispersion ((manufactured by Tokuyama Corporation, 'NJ-321A'), solid content concentration 35%, tensile strength 50 MPa, elongation at break 400%).

[0140] The tensile strength and elongation at break of the above water-dispersible urethane (meth)acrylate and the single cured body of the water-dispersible urethane resin were measured by the method described above. <Photochromic curable composition> As the materials for the photochromic curable composition, the following materials were used.

[0141] ((Meth)acrylic monomer) TMPT; Trimethylolpropane trimethacrylate. 14G; Polyethylene glycol dimethacrylate (the average chain length of the ethylene glycol chain is 14 and the average molecular weight is 736). A-400; Polyethylene glycol diacrylate (the average chain length of the ethylene glycol chain is 9 and the average molecular weight is 508) SI-1: γ-Methacryloyloxypropyltrimethoxysilane GMA: Glycidyl methacrylate RX-1: Polyrotaxane having a (meth)acrylate group (According to the method described in International Publication No. WO2018 / 030275, a polyrotaxane having a (meth)acrylate group satisfying the following characteristics was synthesized. (Weight average molecular weight Mw (GPC) of polyrotaxane having a (meth)acrylate group); 880,000 Acrylate group modification ratio: 85 mol% (Ratio of OH groups remaining in the side chain; 15 mol%) Axial molecule; Linear polyethylene glycol (PEG) with a molecular weight of 20,000 Inclusion ring; α-Cyclodextrin (α-CD) introduction ratio 0.25 End of the axial molecule; Sealed with adamantane (Side chain introduced into the inclusion ring; (Average) molecular weight of the side chain is about 600 (Photochromic compound) PC1: Compound represented by the following formula

[0142] [Chemical formula]

[0143] (Polymerization initiator) CGI: Phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (trade name: Omnirad 819, manufactured by IGM) (Other additive components) HALS: Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate (molecular weight 508) (UV stabilizer) HP: Ethylenebis(oxyethylene) bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate] (manufactured by Ciba Specialty Chemicals, Irganox 245) (UV stabilizer) L7001: Trade name; L7001 manufactured by Toray Dow Corning Co., Ltd. (Leveling agent) (Optical laminate) Lens substrate A: Center thickness 2.0 mm, refractive index 1.60, thiourethane-based plastic lens. Lens substrate C: Center thickness 2.0 mm, refractive index 1.67, thiourethane-based plastic lens Lens substrate D: Center thickness 2.0 mm, refractive index 1.59, polycarbonate plastic lens. Lens substrate E: Center thickness 2.0 mm, refractive index 1.50, methacrylic-based plastic lens. Lens substrate F: Center thickness 2.0 mm, refractive index 1.60, plastic lens with a methacrylic resin coating layer (photochromic coat layer) (Example 1) (Preparation of photocurable primer composition (P1) for optical articles) 3 parts by mass of a water-soluble functional dye (A1), 100 parts by mass of a water-dispersed urethane acrylate (C1), and 0.1 part by mass of 2-hydroxy-2-methyl-1-phenylpropan-1-one (D2) were thoroughly mixed to obtain a mixture. This mixture was filtered through a cellulose acetate filter paper (mesh; 0.8 μm) to obtain a photocurable primer composition (P1) for optical articles. In this composition P1, the water-soluble functional dye A1 was dissolved.

[0144] (Preparation of the photochromic curable composition (F1)) 30 parts by mass of TMPT, 21 parts by mass of A-400, 3 parts by mass of RX-1, 40 parts by mass of 14G, 3 parts by mass of SI-1, 1 part by mass of GMA, 2 parts by mass of PC1, 0.3 part by mass of CGI, 3 parts by mass of HALS, 1 part by mass of HP, and 0.1 part by mass of L7001 were mixed, and this was stirred and mixed at 70 °C for 15 minutes to obtain a photochromic curable composition (F1).

[0145] (Manufacture of the optical laminate) As a lens substrate, a thiourethane-based plastic lens (lens substrate A) with a center thickness of 2.0 mm and a refractive index of 1.60 was prepared. For this lens substrate, after performing alkali etching at 50 °C for 5 minutes using a 10% aqueous sodium hydroxide solution, it was thoroughly washed with distilled water.

[0146] Using a spin coater (1H-DX2, manufactured by MIKASA), a photocurable aqueous primer composition (P1) for optical articles was spin-coated on the surface of the lens substrate to obtain a coating film. This coating film was dried at room temperature (20 - 25 °C) for 10 minutes to obtain a laminate in which an uncured primer layer was laminated on the lens substrate. The film thickness of the uncured primer layer was adjusted to be 10 μm.

[0147] Next, about 2 g of the photochromic curable composition (F1) was spin-coated on the surface of the uncured primer layer to obtain a laminate in which a lens substrate, an uncured primer layer, and an uncured photochromic resin layer (PC resin layer) were laminated in this order. The film thickness of the photochromic resin layer was adjusted to be 40 ± 1 μm. In a nitrogen gas atmosphere, the uncured photochromic resin layer of this laminate was irradiated with light to cure the uncured primer layer and the uncured photochromic resin layer. When irradiating with light, the output at 405 nm was adjusted to be 200 mW / cm 2 2. The light irradiation time was 90 seconds. For the light irradiation, F3000SQ equipped with a D valve manufactured by Fusion UV Systems was used.

[0148] Next, the laminate after photocuring was heat-treated in a thermostat at 100 °C for 1 hour to obtain a photochromic optical laminate.

[0149] <Examples 2 to 8, Comparative Example 1> Photochromic optical laminates according to Examples 2 to 8 and Comparative Example 1 were produced in the same manner as described in Example 1, except that the materials shown in Table 1 were used.

[0150] <Example 9> A photochromic optical laminate was obtained in the same manner as described in Example 1, except that the materials shown in Table 1 were used and the uncured primer layer formed by spin coating on the lens substrate was dried and cured at 80 °C for 20 minutes.

[0151] <Examples 10, Comparative Example 2> Photochromic optical laminates according to Examples 10 and Comparative Example 2 were produced in the same manner as described in Example 9, except that the materials shown in Table 1 were used.

[0152] <Example 11> After curing the coating film of the aqueous primer composition (P1) for an optical article applied on a lens substrate by light irradiation, a photochromic curable composition was applied on the cured primer layer, and a photochromic optical laminate was produced in the same manner as described in Example 1, except that the coating film of the photochromic curable composition was cured by light irradiation. When the primer layer and the photochromic resin layer were photocured, the same conditions as those for the photocuring of the photochromic resin layer described in Example 1 were used.

[0153] <Example 12> An optical laminate was produced in the same manner as described in Example 11, except that a hard coat layer was laminated instead of providing a photochromic resin layer on the cured primer layer, and the film thickness of the primer layer was in the range of 2.0 to 3.0 μm.

[0154] The hard coat layer was provided by applying a hard coat composition on the cured primer layer by the dip coating method and then heating the obtained coating film at a temperature of 110 °C for 2 hours. The film thickness of the hard coat layer was 3 μm. In the dip coating method, the pulling-up speed was 15 cm / min.

[0155] The hard coat composition was prepared by the following method. First, 58.8 g of γ-glycidoxypropyltrimethoxysilane, 47.3 g of methyltriethoxysilane, 47.5 g of ethylene glycol monoisopropyl ether, 25.2 g of acetylacetone, 82.8 g of t-butyl alcohol, and 0.25 g of a silicone-based surfactant (manufactured by Toray Dow Corning Co., Ltd., trade name "L-7001") were mixed to obtain a mixture. To this mixture at 40 °C, 25 g of 0.05 N hydrochloric acid, 13.9 g of a 0.1 N methanol solution of tetramethylammonium chloride, 198.0 g of a methanol-dispersed silica sol, and 1.4 g of tris(2,4-pentanedionato)aluminum(III) were added in order while stirring, and the mixture was further stirred for 48 hours. After stirring, 0.59 g of tris(2,4-pentanedionato)aluminum(III) was mixed to prepare a hard coat composition.

[0156] <Examples 13 to 16> Photochromic optical laminates according to Examples 13 to 16 were produced in the same manner as described in Example 12, except that the lens substrates shown in Table 1 were used.

[0157] [Evaluation Test] <Vickers Hardness> A Vickers hardness test was conducted on the optical laminate according to Example 1. As a result, the Vickers hardness of the optical laminate according to Example 1 was 12.0.

[0158] <Photochromic Property Evaluation Test> For the optical laminates according to Examples 1 to 11, Comparative Examples 1 and 2, the maximum absorption wavelength, coloring density, and fading density were measured. As a result, in the optical laminates according to Examples 1 to 11, Comparative Examples 1 and 2, the maximum absorption wavelength was 588 nm, the coloring density was 1.0, and the fading rate was 56 seconds. The details of each measurement method are as follows.

[0159] 1) Photochromic Properties A xenon lamp L-2480 (300 W) SHL-100 manufactured by Hamamatsu Photonics K.K. was irradiated through an air mass filter (manufactured by Corning) at 20 ± 1 °C for 120 seconds with a beam intensity of 365 nm = 2.4 mW / cm 2 , 245 nm = 24 μW / cm 2 to cause coloring, and the photochromic property was measured. · Maximum Absorption Wavelength (λmax): It is the maximum absorption wavelength after coloring determined by a spectrophotometer (instant multi-channel photodetector MCPD1000) manufactured by Otsuka Electronics Co., Ltd. · Coloring Density {ε(120) - ε(0)}: The difference between the absorbance {ε(120)} after 120 seconds of light irradiation and the absorbance ε(0) before light irradiation at the maximum absorption wavelength. The higher this value, the better the photochromic property. · Fading Rate [t1 / 2 (sec.)]: The time required for the absorbance at the maximum absorption wavelength of the sample to decrease to 1 / 2 of {ε(120) - ε(0)} when the light irradiation is stopped after 120 seconds of light irradiation. It can be said that the shorter this time, the better the photochromic property.

[0160] <Transmittance at 350 nm and transmittance at 465 nm> The primer compositions used in Examples 1 to 16, Comparative Example 1 and Comparative Example 2 were coated on quartz glass so as to have the same film thickness as each example and comparative example, and for the obtained laminate, a UV-vis spectrum was obtained by ultraviolet-visible spectroscopy. From this spectrum, the transmittance at 350 nm and the transmittance at 465 nm were calculated. The results are shown in Table 1.

[0161] <Adhesion> Regarding the optical laminates according to Examples 1 to 16, Comparative Example 1 and Comparative Example 2, the adhesion was evaluated by a cross-cut tape test according to Japanese Industrial Standard JIS D-0202. That is, using a cutter knife, cuts were made on the surface of the photochromic layer or the hard coat layer of the obtained optical laminate at intervals of about 1 mm to form 100 meshes. A cellophane adhesive tape (Nichiban Co., Ltd.'s Cellotape (registered trademark)) was strongly attached onto this mesh, and then, after pulling and peeling it off at once in a direction 90° from the surface, the number of meshes where the photochromic layer or the hard coat layer remained was counted. The results are shown in Table 1.

[0162] <Weather-resistant adhesion> Regarding the optical laminates according to Examples 1 to 16, Comparative Example 1 and Comparative Example 2, the weather-resistant adhesion was evaluated by the following method. First, the optical laminate was installed in an ultraviolet fluorescent lamp type accelerated weathering tester (QUV) manufactured by Q Lab Corporation, and at a temperature of 60 °C, 0.89 w / m 2UVA-340 lamp irradiation was carried out for 8 hours. Then, UV irradiation of the optical laminate was stopped, and it was left standing for 4 hours under humidification conditions at a temperature of 50°C. These series of tests were regarded as one cycle, and the adhesion was evaluated in the same manner as the above-described adhesion test every 24 hours, that is, for 2 cycles. Table 1 shows the maximum time for maintaining a state where 95 or more squares remained without peeling among 100 squares. The maximum time of the test was 360 hours.

[0163]

Table 1

[0164] As is clear from the above Examples 1 to 16, it can be seen that the plastic lens obtained using the aqueous primer composition for an optical article containing a water-soluble ultraviolet absorber has excellent weather adhesion. However, in Comparative Examples 1 and 2, the weather adhesion was insufficient.

Claims

1. A plastic lens substrate, a primer layer provided on at least one main surface of the plastic lens substrate and containing a cured product of an aqueous primer composition for an optical article, a resin layer provided on the surface of the primer layer opposite to the surface in contact with the plastic lens substrate and containing at least one resin selected from the group consisting of (meth)acrylic resins, urethane resins, urethane-urea resins, and resins having a siloxane bond An optical laminate comprising: The aqueous primer composition for an optical article is at least one compound selected from the group consisting of urethane acrylate, acrylic monomer, acrylic resin, urethane resin, and ester resin, a water-soluble functional dye, and water A lens containing the same.

2. The lens according to claim 1, wherein the water-soluble functional dye contains a water-soluble ultraviolet absorber having a maximum absorption peak in a wavelength region of 250 nm or more and less than 420 nm.

3. The lens according to claim 1 or 2, wherein the water-soluble functional dye contains a water-soluble blue light absorber having a maximum absorption peak in a wavelength region of 420 nm or more and 500 nm or less.

4. The lens according to any one of claims 1 to 3, wherein the content of the water-soluble functional dye is 0.1% by mass or more and 10% by mass or less.

5. The lens according to claim 1 or 2, comprising at least one polymer selected from the group consisting of urethane acrylate and urethane resin and a water-soluble functional dye.

6. Glasses comprising the lens according to claim 1 or 2.

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