阅读说明：本技术 光学物品用涂布组合物、眼镜镜片、眼镜及眼镜镜片的制造方法、光学物品及其制造方法 (Coating composition for optical article, spectacle lens, spectacle and method for producing spectacle lens, optical article and method for producing optical article ) 是由 岛田拓哉 山下照夫 于 2020-03-27 设计创作，主要内容包括：本发明提供光学物品用涂布组合物,其包含光致变色化合物及2种以上的(甲基)丙烯酸酯,其中,上述2种以上的(甲基)丙烯酸酯包含脂环式的2官能(甲基)丙烯酸酯、和非环状的3官能以上的(甲基)丙烯酸酯。(The present invention provides a coating composition for optical articles, comprising a photochromic compound and 2 or more kinds of (meth) acrylates, wherein the 2 or more kinds of (meth) acrylates comprise alicyclic 2-functional (meth) acrylates and acyclic 3-or more-functional (meth) acrylates.)

1. A coating composition for optical articles, comprising a photochromic compound and 2 or more (meth) acrylates,

the 2 or more (meth) acrylates comprise:

an alicyclic 2-functional (meth) acrylate, and

acyclic 3-or higher functional (meth) acrylates.

2. The coating composition for optical articles according to claim 1,

the 2 or more (meth) acrylates further comprise a non-cyclic 2-functional (meth) acrylate.

3. The coating composition for optical articles according to claim 1 or 2,

the coating composition for optical articles contains 50 mass% or more of the alicyclic 2-functional (meth) acrylate with respect to the total amount of the 2 or more types of (meth) acrylates.

4. The coating composition for optical articles according to any one of claims 1 to 3, wherein,

the alicyclic 2-functional (meth) acrylate is a methacrylate.

5. An eyeglass lens, comprising:

a lens base material, and

a photochromic layer obtained by curing the coating composition for optical articles according to any one of claims 1 to 4.

6. An eyeglass comprising the eyeglass lens according to claim 5.

7. An optical article, having:

a base material, and

a photochromic layer obtained by curing the coating composition for optical articles according to any one of claims 1 to 4.

8. The optical article according to claim 7, which is a lens for a goggles.

9. The optical article of claim 7, which is a visor portion of a sun visor cap.

10. The optical article of claim 7, which is a masking member of a helmet.

11. A method of manufacturing an optical article, the method comprising:

coating the coating composition for optical articles according to any one of claims 1 to 4 on a substrate, and

the photochromic layer is formed by curing the coated coating composition for an optical article.

12. The method of manufacturing an optical article according to claim 11,

the optical article is a spectacle lens.

13. The method of manufacturing an optical article according to claim 11,

the optical article is a lens for a goggles.

14. The method of manufacturing an optical article according to claim 11,

the optical article is a visor portion of the sun visor cap.

15. The method of manufacturing an optical article according to claim 11,

the optical article is a shield member of a helmet.

Technical Field

The present invention relates to a coating composition for optical articles, spectacle lenses, spectacles, and a method for producing spectacle lenses, and an optical article and a method for producing the same.

Background

The photochromic compound is a compound having a property (photochromic property) of developing a color when irradiated with light having a wavelength range of photoresponsiveness and fading a color when not irradiated. As a method for imparting photochromic properties to an optical article such as a spectacle lens, there is a method in which a coating layer containing a photochromic compound and a curable compound is provided on a base material, and the coating layer is cured to form a cured layer (photochromic layer) having photochromic properties (for example, see patent document 1).

Documents of the prior art

Patent document

Patent document 1: WO2003/011967

Disclosure of Invention

Problems to be solved by the invention

As a property desired for the optical article having photochromic properties as described above, there is a high response speed to light (excellent light responsiveness). In addition, it is also desirable that the color density is high when the color is developed by light irradiation.

An embodiment of the present invention provides a coating composition for an optical article, which can form a photochromic layer that is excellent in light responsiveness and can develop color at a high concentration.

Means for solving the problems

One embodiment of the present invention relates to a coating composition for optical articles (hereinafter also simply referred to as "composition") comprising a photochromic compound and 2 or more kinds of (meth) acrylates,

the 2 or more (meth) acrylates comprise:

an alicyclic 2-functional (meth) acrylate, and

acyclic 3-or higher functional (meth) acrylates.

The coating composition for optical articles contains, as the (meth) acrylate, an alicyclic 2-functional (meth) acrylate and an acyclic 3-or more-functional (meth) acrylate. Thus, the photochromic compound can exhibit excellent photoresponsiveness in the photochromic layer formed by curing the composition, and can develop color at a high concentration when irradiated with light.

ADVANTAGEOUS EFFECTS OF INVENTION

According to one embodiment of the present invention, a coating composition for an optical article capable of forming a photochromic layer which is excellent in light responsiveness and capable of developing color at a high concentration can be provided. Further, according to one embodiment of the present invention, there is provided an eyeglass lens having a photochromic layer, which is excellent in light responsiveness and can develop color at high concentration when irradiated with light.

Drawings

FIG. 1 shows the evaluation results of the color development concentrations of examples and comparative examples.

FIG. 2 shows the evaluation results of the photoresponsiveness (fading speed) of examples 1 to 3 and comparative example 1.

Fig. 3 shows the evaluation results of curability in examples and comparative examples.

Detailed Description

[ coating composition for optical articles ]

A coating composition for an optical article according to one embodiment of the present invention includes a photochromic compound and 2 or more kinds of (meth) acrylates. These components are described in further detail below.

[ meth (acrylic acid ester ]

In the present invention and the present specification, "(meth) acrylate" is used in a meaning including acrylate and methacrylate. "acrylate" refers to a compound having 1 or more acryloyl groups in 1 molecule. "methacrylate" refers to a compound having 1 or more methacryloyl groups in 1 molecule. In the present invention and the present specification, "methacrylate" refers to a compound containing only a methacryloyl group as a (meth) acryloyl group, and a compound containing both an acryloyl group and a methacryloyl group as a (meth) acryloyl group is referred to as an acrylate. The acryloyl group may contain an acryloyloxy group, and the methacryloyl group may contain a methacryloyloxy group. The following "(meth) acryloyl group" is used in the sense of including an acryloyl group and a methacryloyl group, and the following "(meth) acryloyloxy group" is used in the sense of including an acryloyloxy group and a methacryloyloxy group. The groups described may have a substituent or may be unsubstituted, unless otherwise specified. When a group has a substituent, examples of the substituent include an alkyl group (e.g., an alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (e.g., an alkoxy group having 1 to 6 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, and a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, and a carboxyl group. The "number of carbon atoms" of a group having a substituent means the number of carbon atoms of a moiety excluding the substituent.

The composition comprises more than 2 (methyl) acrylic esters. 1 of them is an alicyclic 2-functional (meth) acrylate, and the other is an acyclic 3-or more-functional (meth) acrylate. The alicyclic 2-functional (meth) acrylate refers to a compound having an alicyclic structure, and the number of (meth) acryloyl groups contained in 1 molecule is 2. In the present invention and the present specification, "acyclic" means not including a cyclic structure. In contrast, "cyclic" means including a cyclic structure. The acyclic 3-or more-functional (meth) acrylate refers to a compound containing no cyclic structure and having 3 or more (meth) acryloyl groups in 1 molecule. It is presumed that the reason why the photochromic layer formed from the composition can develop color at a high concentration when irradiated with light and exhibits excellent photoresponsiveness is that these compounds are contained.

(alicyclic 2-functional (meth) acrylate)

The alicyclic 2-functional (meth) acrylate may be, for example, a 2-functional (meth) acrylate having the formula R¹-(L¹)n1-Q-(L²)n2-R²A compound of the structure shown. Wherein Q represents a divalent alicyclic group, R¹And R²Each independently represents a (meth) acryloyl group or a (meth) acryloyloxy group, L¹And L²Each independently represents a linking group, and n1 and n2 each independently represents 0 or 1. The divalent alicyclic group represented by Q is preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and examples thereof include cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, tricyclodecylene, adamantylene, and the like. As a result of L¹And L²Examples of the linking group include alkylene groups. The alkylene group may be, for example, an alkylene group having 1 to 6 carbon atoms.

Specific examples of the alicyclic 2-functional (meth) acrylate include cyclohexanedimethanol di (meth) acrylate, ethoxylated cyclohexanedimethanol di (meth) acrylate, propoxylated cyclohexanedimethanol di (meth) acrylate, ethoxylated propoxylated cyclohexanedimethanol di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, ethoxylated tricyclodecane dimethanol di (meth) acrylate, propoxylated tricyclodecane dimethanol di (meth) acrylate, and ethoxylated propoxylated tricyclodecane dimethanol di (meth) acrylate. The alicyclic 2-functional (meth) acrylate may have a molecular weight of, for example, 200 to 400, but is not limited thereto. In the present invention and the present specification, the molecular weight of the polymer is a theoretical molecular weight calculated from a structural formula determined by structural analysis of the compound or from a raw material charge ratio at the time of production. The alicyclic 2-functional (meth) acrylate may contain only an acryloyl group or only a methacryloyl group as a (meth) acryloyl group, and may contain an acryloyl group and a methacryloyl group. In one embodiment, the alicyclic 2-functional (meth) acrylate preferably contains only a methacryloyl group as a (meth) acryloyl group, that is, is preferably a methacrylate.

(acyclic 3 or more functional (meth) acrylate)

The acyclic 3-or more-functional (meth) acrylate is preferably a 3-to 5-functional (meth) acrylate, more preferably a 3-or 4-functional (meth) acrylate, and still more preferably a 3-functional (meth) acrylate. Specific examples of the acyclic 3-or more-functional (meth) acrylate include pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, trimethylolethane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, tetramethylolmethane tri (meth) acrylate, and the like. The molecular weight of the acyclic 3-or higher-functional (meth) acrylate may be, for example, 200 to 400, but is not limited thereto. The acyclic 3-or higher-functional (meth) acrylate may contain only an acryloyl group, only a methacryloyl group, and both an acryloyl group and a methacryloyl group as the (meth) acryloyl group. In one embodiment, the acyclic 3-or more functional (meth) acrylate preferably contains only a methacryloyl group as the (meth) acryloyl group, i.e., is preferably a methacrylate.

(other (meth) acrylic acid esters)

The composition may contain 1 or 2 or more kinds of alicyclic 2-functional (meth) acrylates and 1 or 2 or more kinds of acyclic 3-or more-functional (meth) acrylates as the (meth) acrylates. The composition may contain one or more other (meth) acrylates in addition to these (meth) acrylates, or may contain no other (meth) acrylates. Other (meth) acrylates are useful, for example, for adjusting the viscosity of the composition. The other (meth) acrylate may be, for example, an acyclic or cyclic (meth) acrylate having 2 or more functional groups. The other (meth) acrylate may be a 2-5 functional (meth) acrylate, preferably a 2-4 functional (meth) acrylate, more preferably a 2-or 3-functional (meth) acrylate, and still more preferably a 2-functional (meth) acrylate. The molecular weight of the other (meth) acrylate may be, for example, 150 to 350, but is not limited to this range.

In one embodiment, the other (meth) acrylate may be a non-cyclic 2-functional (meth) acrylate. Specific examples thereof include neopentyl glycol di (meth) acrylate, ethoxylated neopentyl glycol di (meth) acrylate, propoxylated neopentyl glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol diacrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and the like.

The content of the alicyclic 2-functional (meth) acrylate is preferably 50% by mass or more, more preferably 55% by mass or more, and still more preferably 60% by mass or more, assuming that the total amount of 2 or more (meth) acrylates contained in the composition is 100% by mass. The content of the alicyclic 2-functional (meth) acrylate may be, for example, 80% by mass or less, or more than 80% by mass. On the other hand, the content of the acyclic 3-functional or higher (meth) acrylate is preferably 5% by mass or higher, more preferably 7% by mass or higher, and still more preferably 10% by mass or higher, assuming that the total amount of 2 or more (meth) acrylates contained in the composition is 100% by mass. The content of the acyclic 3-or more-functional (meth) acrylate is preferably 20% by mass or less, and more preferably 15% by mass or less. The total content of the alicyclic 2-functional (meth) acrylate and the acyclic 3-functional or higher (meth) acrylate is preferably 55% by mass or higher, more preferably 60% by mass or higher, further preferably 65% by mass or higher, and still further preferably 70% by mass or higher, assuming that the total amount of 2 or more (meth) acrylates contained in the composition is 100% by mass. The total content of the alicyclic 2-functional (meth) acrylate and the acyclic 3-or more-functional (meth) acrylate may be 90% by mass or less, or 85% by mass or less, for example. On the other hand, when the total amount of 2 or more (meth) acrylic esters contained in the composition is 100% by mass, the content of other (meth) acrylic esters other than the alicyclic 2-functional (meth) acrylic ester and the acyclic 3-functional or more (meth) acrylic ester may be 0% by mass or more than 0% by mass. When the total amount of 2 or more (meth) acrylic acid esters contained in the composition is defined as 100% by mass, the content of other (meth) acrylic acid esters in the composition is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 7% by mass, and still more preferably 10% by mass or more. The content of the other (meth) acrylate is preferably 40% by mass or less, more preferably 35% by mass or less, and still more preferably 30% by mass or less. The composition may contain all (meth) acrylic acid esters at a content of, for example, 80 to 99.9 mass% with respect to 100 mass% of the total amount of the composition.

< photochromic Compound >

The composition contains 2 or more kinds of (methyl) acrylate and also contains photochromic compounds. As the photochromic compound contained in the composition, a known compound exhibiting photochromic properties can be used. The photochromic compound may exhibit photochromic properties to ultraviolet rays, for example. For example, as the photochromic compound, fulgimide (fulgimide) compound, spiroA compound having a known skeleton exhibiting photochromic properties, such as an oxazine compound, a chromene compound, and an indeno-fused naphthopyran compound. The photochromic compound may be used alone in 1 kind, or may be used in combination of 2 or more kinds. The content of the photochromic compound in the composition may be, for example, about 0.1 to 15% by mass, based on 100% by mass of the total composition, but is not limited to this range.

< optional ingredients >

Since the (meth) acrylate described above is a curable compound, the composition containing the (meth) acrylate can be a curable composition, and if subjected to a curing treatment, can be cured to form a cured layer. The above composition may contain a polymerization initiator for initiating a curing reaction (also referred to as polymerization reaction). As the polymerization initiator, a known polymerization initiator such as a photopolymerization initiator or a thermal polymerization initiator can be used depending on the kind of the curing reaction. The amount of the polymerization initiator to be used may be determined depending on the polymerization conditions, the type of the polymerization initiator, and the type of the curable compound contained in the curable composition.

The composition may further contain known additives which can be added to the composition containing a photochromic compound, and for example, additives such as a surfactant, an antioxidant, a radical scavenger, a light stabilizer, an ultraviolet absorber, an anti-coloring agent, an antistatic agent, a fluorescent dye, a pigment, a fragrance, a plasticizer, and a silane coupling agent may be added in an arbitrary amount. As these additives, known compounds can be used.

The above composition can be prepared by mixing the above-described respective ingredients simultaneously or sequentially in any order.

The composition is a coating composition for optical articles. The coating composition for optical articles is a composition to be coated on a substrate or the like for the production of optical articles. As the optical article, various lenses can be cited, and spectacle lenses can be preferably cited. The spectacle lens produced by applying the above composition to a lens base material can exhibit photochromic properties as a spectacle lens having a photochromic layer.

[ spectacle lens and method for producing spectacle lens ]

One embodiment of the present invention relates to a spectacle lens and a method for manufacturing the spectacle lens.

The spectacle lens comprises a lens base material and a photochromic layer obtained by curing the composition;

the method for manufacturing the spectacle lens comprises the following steps:

applying the above composition to a lens substrate, and

the applied composition is subjected to a curing treatment to form a photochromic layer.

The spectacle lens and the method of manufacturing the spectacle lens will be described in further detail below.

< lens base >

The lens base material included in the above-mentioned spectacle lens may be a plastic lens base material or a glass lens base material. The glass lens substrate may be, for example, a lens substrate made of inorganic glass. As the lens base material, a plastic lens base material is preferable from the viewpoint of light weight, difficulty in breaking, and easiness in handling. Examples of the plastic lens base material include a styrene resin typified by a (meth) acrylic resin, a polycarbonate resin, an allyl carbonate resin such as an allyl resin and an allyl diglycol carbonate resin (CR-39), a vinyl resin, a polyester resin, a polyether resin, a urethane resin obtained by reacting an isocyanate compound with a hydroxyl compound such as diethylene glycol, a thiocarbamate resin obtained by reacting an isocyanate compound with a polythiol, and a cured product (generally referred to as a transparent resin) obtained by curing a curable composition containing a (thio) epoxy compound having 1 or more disulfide bonds in the molecule. As the lens base material, an undyed lens base material (colorless lens) may be used, or a dyed lens base material (dyed lens) may be used. The refractive index of the lens base material may be, for example, about 1.60 to 1.75. However, the refractive index of the lens base is not limited to the above range, and may be within the above range or may be deviated from the above range in the up-down direction. In the present invention and the present specification, the refractive index refers to a refractive index for light having a wavelength of 500 nm. The lens base material may be a lens having a refractive power (so-called power lens) or a lens having no refractive power (so-called power lens).

The spectacle lens may be any of various lenses such as a single focus lens, a multi-focus lens, and a progressive power lens. The type of lens is determined by the shape of the two surfaces of the lens substrate. In addition, the surface of the lens base material may be any one of a convex surface, a concave surface, and a flat surface. In general, the lens base material and the spectacles have a convex object-side surface and a concave eyeball-side surface, but the present invention is not limited thereto. The photochromic layer is typically disposed on the object-side surface of the lens substrate, but may be disposed on the eyeball-side surface.

The photochromic layer formed using the above composition may be directly provided on the surface of the lens base material, or may be indirectly provided through one or more other layers. As the other layer, an undercoat layer for improving adhesion between the photochromic layer and the lens base material is exemplified, and such an undercoat layer is known.

< photochromic layer >

The photochromic layer of the spectacle lens may be formed by applying the composition directly or indirectly via one or more other layers on a lens substrate and curing the applied composition. As the coating method, a known coating method such as a spin coating method or a dip coating method can be used, and the spin coating method is preferable from the viewpoint of coating uniformity. The curing treatment may be light irradiation and/or heat treatment, and is preferably light irradiation from the viewpoint of allowing the curing reaction to proceed in a short time. The curing conditions may be determined depending on the kinds of the various components (the (meth) acrylate, the polymerization initiator, and the like described above) contained in the composition, and the composition of the composition. The thickness of the photochromic layer formed in this way is, for example, preferably in the range of 5 to 80 μm, and more preferably in the range of 20 to 60 μm.

The spectacle lens having the photochromic layer may have one or more functional layers in addition to the photochromic layer, or may not have a functional layer. Examples of the functional layer include layers known as functional layers for spectacles, such as hard coat layers, antireflection layers, hydrophobic or hydrophilic antifouling layers, and antifogging layers.

[ spectacles ]

One embodiment of the present invention relates to eyeglasses provided with the eyeglass lenses. The details of the spectacle lenses included in the spectacles are as described above. The above-mentioned spectacles have the above-mentioned spectacle lens, and for example, a photochromic compound contained in an outdoor photochromic layer develops color by irradiation of sunlight, whereby an antiglare effect like sunglasses can be exhibited, and the photochromic compound fades when returning to the indoor, and the transmittance can be restored. The above glasses can be applied to a known technique such as a structure of a frame.

[ optical article and method for producing optical article ]

One embodiment of the present invention relates to an optical article and a method for manufacturing the optical article.

The optical article comprises a base material and a photochromic layer obtained by curing the composition;

the method of manufacturing the optical article comprises the steps of:

applying the above composition to a substrate, and

the coated composition is subjected to a curing treatment to form a photochromic layer.

One embodiment of the optical article is the spectacle lens described above. In addition, as one embodiment of the optical article, a lens for a goggle, a visor portion of a sun visor cap, a shielding member of a helmet, and the like can be cited. An optical article having an antiglare function can be obtained by applying the composition to a substrate for such optical articles and curing the applied composition to form a photochromic layer.

Examples

The present invention will be further described with reference to examples. However, the present invention is not limited to the embodiments shown.

[ example 1]

< preparation of coating composition for optical article >

In a plastic container, 68 mass% of tricyclodecanedimethanol (meth) acrylate (alicyclic 2-functional (meth) acrylate), 12 mass% of trimethylolpropane trimethacrylate (acyclic 3-functional (meth) acrylate), and 20 mass% of neopentyl glycol dimethacrylate (other (meth) acrylate) were mixed with respect to 100 mass% of the total amount of the (meth) acrylates to prepare a (meth) acrylate mixture. To this (meth) acrylate mixture, a photochromic compound (an indeno-fused naphthopyran compound represented by the structural formula described in U.S. Pat. No. 5645767), a photopolymerization initiator (phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide), an antioxidant (bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionic acid ] [ ethylenebis (oxyethylene) ]), and a light stabilizer (bis (1, 2,2, 6, 6-pentamethylpiperidinol) sebacate) were mixed and sufficiently stirred, and then a silane coupling agent (γ -methacryloxypropyltrimethoxysilane) was added dropwise with stirring. Then, defoaming was performed by an automatic revolution type stirring and defoaming device.

By the above method, a coating composition for an optical article having a composition shown in table 1 below was prepared.

[ Table 1]

Composition (I)	Content ratio (% by mass)
		Alicyclic 2-functional (meth) acrylates	58.97
Acyclic 3-functional (meth) acrylates	10.41
		Other (meth) acrylic esters	17.35
Photochromic compounds	2.60
		Photopolymerization initiator	0.26
Antioxidant agent	2.60
		Light stabilizers	2.60
Silane coupling agent	5.20

< production of spectacle lens >

A plastic lens base material (trade name EYAS manufactured by HOYA Co., Ltd.; center thickness 2.5mm, radius 75mm, S-4.00) was immersed in a 10 mass% aqueous solution of sodium hydroxide (liquid temperature 60 ℃ C.) for 5 minutes, and then washed and dried with pure water. After that, a primer layer is formed on the convex surface (object side surface) of the plastic lens base material. Specifically, an aqueous urethane resin solution (polycarbonate polyol-based urethane emulsion; viscosity 100CPS, solid content concentration 38% by mass) was applied to the convex surface of a plastic lens base material by a spin coating method in an environment of 25 ℃ and 50% relative humidity, and then dried naturally for 15 minutes to form a primer layer having a thickness of 5.5 μm.

The composition prepared above was applied on the undercoat layer by spin coating. The spin coating method is carried out by the method described in Japanese patent laid-open No. 2005-218994. Then, the composition applied to the plastic substrate was irradiated with ultraviolet rays (wavelength: 405nm) in a nitrogen atmosphere (oxygen concentration: 500ppm or less) to cure the composition, thereby forming a photochromic layer. The photochromic layer was formed to have a thickness of 45 μm.

In the examples and comparative examples, the degree of progress of the curing reaction of the plurality of photochromic layers was changed by changing the light irradiation time.

[ example 2]

A spectacle lens having a photochromic layer was produced in the same manner as in example 1, except that the alicyclic 2-functional (meth) acrylate was changed to tricyclodecane dimethanol diacrylate.

[ example 3]

An eyeglass lens having a photochromic layer was produced in the same manner as in example 1, except that neopentyl glycol dimethacrylate was not used.

Comparative example 1

An eyeglass lens having a photochromic layer was produced in the same manner as in example 1, except that an ethoxylated bisphenol a dimethacrylate (2, 2-bis [4- (methacryloxypolyethoxy) phenyl ] propane (EO 10mol)) was used instead of the alicyclic 2-functional (meth) acrylate.

Comparative example 2

A spectacle lens having a photochromic layer was produced in the same manner as in example 1, except that polyethylene glycol diacrylate was used instead of the alicyclic 2-functional (meth) acrylate.

[ evaluation method ]

< color development concentration >

Evaluation of photochromic properties was carried out by the following method in accordance with JIS T7333: 2005.

The photochromic layer of each of the spectacle lenses of examples and comparative examples was irradiated with light for 15 minutes (900 seconds) from a xenon lamp through a gas filter onto the surface of the photochromic layer, thereby developing the photochromic compound in the photochromic layer. The transmittance at the time of the color development (measurement wavelength: 550nm) was measured by a spectrophotometer manufactured by Otsuka electronics Co., Ltd. The light irradiation was performed so that the difference between the irradiation illuminance and the allowable irradiation illuminance was the value shown in table 2 below, in accordance with the regulations of JIS T7333.

[ Table 2]

Wavelength region (nm)	Irradiance (W/m)2)	Allowable difference of radiation illuminance (W/m)2)
			300～340	＜2.5	-
340～380	5.6	±1.5
			380～420	12	±3.0
420～460	12	±3.0
			460～500	26	±2.6

The smaller the value of the transmittance measured above, the more highly concentrated the photochromic compound develops.

Fig. 1 shows a graph in which the transmittance obtained as described above is plotted against the light irradiation time when the photochromic layer is formed as a result of evaluation of the color development concentration.

< photoresponsiveness (fading speed) >

The photoresponsiveness (fading speed) was evaluated by the following method.

The transmittance (measurement wavelength: 550nm) before light irradiation (in an undeveloped state) of each of the spectacle lenses of examples and comparative examples was measured by a spectrophotometer manufactured by Otsuka electronics Co., Ltd. The transmittance measured here is referred to as "initial transmittance".

The photochromic layer of each of the spectacle lenses of examples and comparative examples was irradiated with light via a xenon lamp through a gas filter for 15 minutes (900 seconds) to develop the photochromic compound in the photochromic layer, and the transmittance at the time of development was measured in the same manner as described above.

Then, the time (half-life) required from the time when the light irradiation was stopped to the time when the transmittance was [ (initial transmittance-transmittance at the time of color development)/2 ] was measured. The smaller the value of the half-life measured in this manner, the higher the fading speed and the more excellent the light responsiveness.

The hardness (mahalanobis hardness) of the photochromic layer of the spectacle lens after the above evaluation was measured by the following method. The proceeding degree of the curing reaction of the photochromic layer may be judged by the hardness of the photochromic layer, and the harder the photochromic layer is, the higher the proceeding degree of the curing reaction is.

An indenter was pressed into the surface of the photochromic layer with a load of 100mgf using an ultramicro indentation hardness tester ENT-2100 manufactured by Elionix, and the surface area of indenter intrusion was measured from the pressing depth at that time to obtain the Marangstrom hardness (kgf/mm) as "load/indenter intrusion surface area²)。

Fig. 2 shows a graph in which the half-life is plotted against the mahalanobis hardness of the photochromic layer obtained as described above as the evaluation results of the photoresponsiveness (fading speed) of examples 1 to 3 and comparative example 1.

From the results shown in fig. 1, it was confirmed that the spectacle lenses of examples 1 to 3 and comparative example 1 are superior to the spectacle lens of comparative example 2 in terms of color development density.

On the other hand, when examples 1 to 3 and comparative example 1 are compared from the viewpoint of photoresponsiveness (fading speed), as shown in fig. 2, the half-life of the spectacle lenses of examples 1 to 3 is smaller than that of comparative example 1 at the same hardness, and the photoresponsiveness is excellent.

From the above results, it was confirmed that the photochromic compound contained in the photochromic layer of the spectacle lens in examples 1 to 3 has a high color development concentration and excellent light responsiveness.

Fig. 3 is a graph obtained by plotting the measured mahalanobis hardness against the light irradiation time at the time of forming the photochromic layer as the evaluation result of the curability of each of the spectacle lenses of the examples and the comparative examples. According to the results shown in fig. 3, the spectacle lenses of examples 1 to 3 have higher mahalanobis hardness of the photochromic layer than those of comparative examples 1 and 2 at the same light irradiation time. From these results, it was confirmed that the use of an alicyclic 2-functional (meth) acrylate in combination with an acyclic 3-or more-functional (meth) acrylate as a (meth) acrylate is preferable for forming a photochromic layer having a high hardness.

Finally, the above-described modes are summarized.

According to one embodiment, there is provided a coating composition for optical articles, comprising a photochromic compound and 2 or more types of (meth) acrylates, wherein the 2 or more types of (meth) acrylates comprise an alicyclic 2-functional (meth) acrylate and an acyclic 3-functional or more (meth) acrylate.

According to the coating composition for optical articles, a photochromic layer which is excellent in light responsiveness and can develop color at a high concentration can be formed.

In one embodiment, the 2 or more (meth) acrylates may further comprise a non-cyclic 2-functional (meth) acrylate.

In one embodiment, the coating composition for optical articles may contain 50 mass% or more of the alicyclic 2-functional (meth) acrylate with respect to the total amount of the 2 or more (meth) acrylates.

In one embodiment, the alicyclic 2-functional (meth) acrylate is a methacrylate.

According to one embodiment, there is provided an eyeglass lens comprising a lens base material and a photochromic layer obtained by curing the composition.

The spectacle lens can have a photoluminescent layer which is excellent in light responsiveness and can develop color at a high concentration.

According to one aspect, there is provided eyeglasses including the eyeglass lens.

According to one embodiment, there is provided an optical article comprising a base material and a photochromic layer obtained by curing the composition.

According to one aspect, there may be provided a method of manufacturing an optical article, the method comprising: the above composition is applied on a substrate, and a photochromic layer is formed by subjecting the applied composition to a curing treatment.

According to the above manufacturing method, an optical article having an antiglare function can be provided.

In one embodiment, the optical article may be a spectacle lens, a lens for a goggle, a visor portion of a sun visor, a shield member of a helmet, or the like.

The various embodiments described in the present specification can combine 2 or more kinds in arbitrary combinations.

The embodiments disclosed herein are to be considered in all respects as illustrative and not restrictive. The scope of the present invention is intended to include all modifications not described above but shown in the claims, which are equivalent in meaning and scope to the claims.

Industrial applicability

The present invention is useful in the technical fields of eyeglasses, goggles, sun visors, helmets, and the like.