JPH11292909A - Actinic ray curable composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an actinic ray-curable composition which cures in a short time and obtains a cured product having excellent properties such as internal uniformity, surface accuracy, ultraviolet ray cutting property, transparency and hue. . SOLUTION: The composition comprises 40 parts of 2,2-bis [(4-methacryloxy) phenyl] propane, 45 parts of 2,2-bis [(4-methacryloxyethoxy) phenyl] propane, and 15 parts of glycidyl methacrylate. And 0.005 part of bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, and 2-hydroxy-4-
It contains 0.03 parts of methoxybenzophenone and 0.5 parts of tertiary-butylperoxyisobutyrate.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an actinic ray-curable composition which cures when irradiated with actinic rays such as ultraviolet rays,
And a method for producing a lens using the composition.

[0002]

2. Description of the Related Art As a conventional example of an actinic ray-curable composition,
For example, there is one disclosed in JP-A-64-65111. The composition comprises an oligomer having a terminal (meth) acryloyl group as a first component, a reactive diluent monomer having a boiling point of 100 ° C. or more as a second component, and a third component.
As components, 2-hydroxy-2-methyl-1-phenylpropan-1-one, hydroxycyclohexylphenyl ketone and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (hereinafter “TPO”)
Abbreviated. ) And at least one photopolymerization initiator selected from the group consisting of the above-mentioned publications (for example, claims).

[0003] This conventional composition has excellent deep curability and surface hardness, and has no yellow coloring, so that it exhibits an excellent effect in molding optical lenses and the like (see the above publication). For example, the column of the effect of the invention).

The sensitive wavelength of TPO, which is one of the third components, to actinic rays is 370 to 390 nm, which is longer than the sensitive wavelength of ordinary ultraviolet actinic photoinitiators. Therefore, when TPO is used as the third component, there is also an effect that the deep part curability is particularly excellent (column 4, upper right column, lines 10 to 16 of the above-mentioned publication).

[0005]

However, in the conventional actinic ray-curable composition, it is necessary to irradiate the composition with ultraviolet rays for a long time (at least several minutes) in order to cure it. Therefore, the manufacturing efficiency of the lens was not good.

In addition, the longer the irradiation time of the ultraviolet light, the higher the temperature of the composition itself irradiated with light. In particular, ultraviolet rays on the short wavelength side (for example, light having a wavelength of 300 to 380 nm) have high energy, and thus the temperature of the composition is rapidly increased. Therefore, curing shrinkage occurs rapidly during the curing process of the composition, and the cured lens contains distortion and has poor surface accuracy (for example, Comparative Example 2 described later).

[0007] TPO, which is a conventional photopolymerization initiator, also has an absorption on the long wavelength side as described above. Therefore, it is also conceivable to cure the conventional composition containing TPO by irradiating it with ultraviolet light having a longer wavelength. However, TPO has only one site that is cleaved by actinic rays. for that reason,
It is believed that conventional compositions containing TPO generate only a small amount of radicals effective for polymerizing the composition. Therefore, also in this case, long-time light irradiation is required. Therefore, also in this case, it is considered that the above-described problem of temperature rise occurs.

In order to alleviate the rapid rise in temperature and the rapid curing shrinkage, a method in which ultraviolet irradiation is performed several times, for example, as disclosed in JP-A-3-193313, may be used. Conceivable. However, even with such means, the total time of the ultraviolet irradiation step is still long. In addition, management of the ultraviolet irradiation step is complicated. Further, there arises a problem that a plurality of ultraviolet irradiation devices are required.

Accordingly, an object of the present invention is to provide an actinic ray curable composition which cures in a short period of time and provides a cured product having excellent properties such as internal uniformity, surface accuracy, transparency and hue. An object of the present invention is to provide a method suitable for manufacturing a lens using the composition.

[0010]

The inventors of the present application have conducted intensive studies and have found that a specific polymerizable monomer and
It has been found that the above object is achieved by a composition containing a specific photopolymerization initiator.

That is, specific A is used as a polymerizable monomer.
The component and the B component are used. Here, the specific A component is
It is one kind of compound selected from compounds having at least two of at least one of a (meth) acryloyl group and a (meth) acryloxy group in a molecule. Also, a specific B
The component is at least one compound selected from compounds having one (meth) acryloyl group or one (meth) acryloxy group in the molecule.

The (meth) acryloyl group is an acryloyl group having a methyl group or an acryloyl group having no methyl group, and the (meth) acryloxy group is an acryloxy group having a methyl group or an acryloxy group having a methyl group. It represents an acryloxy group having no methyl group.

As the specific photopolymerization initiator, at least one compound (component C) represented by the following formula (1) is used. However, in the formula (1), n is 2 or 3. R1 is selected from a methyl group, a methoxy group, and a chlorine atom, and may be the same or different, or may be partially different when n = 3.
R2 is a 2,4,4-trimethylpentyl group or a phenyl group.

[0014]

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As will be described in detail later, these components A and B
By adjusting the proportions of the components, the viscosity of the polymerizable monomer can be adjusted to a viscosity suitable for molding, and the heat resistance, surface hardness, impact resistance, chemical resistance, mechanical resistance of the polymer after polymerization. Target strength can be adjusted.

Further, the photopolymerization initiator represented by the formula (1) according to the present invention has two sites that are cleaved by actinic rays (two of the CP site and the PC site in the formula (1)). Places).

As described above, TPO, which is a photopolymerization initiator, disclosed in Japanese Patent Application Laid-Open No. 64-65111 has only one site that is cleaved by actinic rays.

The more sites that are cleaved by actinic rays,
Since a large amount of radicals effective for polymerizing the polymerizable monomer are generated, the curing efficiency of the composition is improved. Therefore, the photopolymerization initiator used in the present invention contributes to shortening the light irradiation time required for curing the actinic ray-curable composition. Therefore, the rise in the temperature of the composition during light irradiation can be suppressed.

As can be understood from the data described in detail later (see the characteristic I in FIGS. 1 and 2), the C component has absorption on the long wavelength side in the ultraviolet region. In addition, when compared with the conventional photopolymerization initiator TPO (see characteristic II in FIGS. 1 and 2), specifically, the wavelength 400 to 4
It also has absorption in the 40 nm band. Therefore, compared to the case where TPO is used, light on the longer wavelength side, for example, wavelengths 380 to 440 is used.
Curing using nm can be performed. Since long-wavelength light has smaller energy than short-wavelength light, in the case of the present invention in which long-wavelength light can be used, heat generation during curing of the composition is easily suppressed. Therefore, by adding the component C, it is possible to reduce rapid curing shrinkage due to heat generation of the actinic ray-curable composition.

In practicing the present invention, it is preferable that at least one selected from a benzophenone-based UV absorber and a benzotriazole-based UV absorber is contained in the composition as the UV absorber (D component). is there.

From these facts, the actinic ray-curable composition of the present invention can be cured in a short time and has excellent properties such as internal uniformity, surface accuracy, ultraviolet ray cutting property, transparency and hue. Is obtained.

In practicing the actinic ray-curable composition of the present invention, preferably, the temperature at which the concentration is reduced to half in 10 hours (hereinafter referred to as "temperature for 10 hours half-life")
Abbreviated. ) Is in the range of 45 to 100 ° C., as the E component.

The reason is that the component E acts as a thermal polymerization initiator, so that by adding the component E, the composition of the present invention can be cured by heat. Therefore, it is possible to use both curing by irradiation with actinic rays and curing by heating. For example, curing can be performed by both irradiation of actinic rays and heat generated by the irradiation. It is also possible to cure by irradiation with actinic rays and heating means such as a heating furnace provided separately.

By using such irradiation of actinic rays and curing by heating in combination, higher hardness can be realized in molding. In addition, the degree of freedom of the curing process is improved, and curing under various conditions becomes possible, and the curing process, hardness, and the like are more easily controlled. In addition, by performing heating using a device such as a heating furnace, the curing time can be shortened, and the number of molding processes can be increased, so that a curing process with excellent productivity can be realized. Will be able to In addition, because it promotes curing by heating,
The irradiation time of actinic rays can be shortened.

The reason why the temperature of the 10-hour half-life of the component E is in the range of 45 to 100 ° C. is that if it is in this range, the pot life of the composition itself can be a practical time. Further, the time and the temperature for thermally polymerizing the composition can be set to the time and the temperature that are industrial and easily relax the stress during the thermal polymerization.

The component A of the polymerizable monomer used in the present invention includes ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, and tetraethylene glycol dimethacrylate. Ethylene glycol diacrylate, tetraethylene glycol dimethacrylate, propylene glycol diacrylate,
Propylene glycol dimethacrylate, 1,3-butylene diacrylate, 1,3-butylene dimethacrylate, 1,6-hexamethylene diacrylate, 1,6-
Hexamethylene dimethacrylate, 2,2-bis (4-
Acryloxyphenyl) propane and its halogen-substituted derivatives, 2,2-bis (4-methacryloxyphenyl)
Propane and its halogen-substituted derivatives, 2,2-bis (4-acryloxyethoxyphenyl) propane and its halogen-substituted derivatives, 2,2-bis (4-methacryloxyethoxyphenyl) propane and its halogen-substituted derivatives, 2,2 -Bis (4-acryloxycyclohexyl) propane, 2,2-bis (4-methacryloxycyclohexyl) propane, 4,4'-bis (β-acryloyloxyethylthio) diphenylsulfone, 4,
4'-bis (β-methacryloyloxyethylthio) diphenylsulfone, pentaerythritol triacrylate, pentaerythritol trimethacrylate, triacrylate of tris (2-hydroxyethyl) isocyanurate, trimethacrylate of tris (2-hydroxyethyl) isocyanurate And other known compounds.

One of these A components may be used alone, or two or more may be used in combination.

Further, as the component B of the polymerizable monomer used in the present invention, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate,
Cyclohexyl acrylate, cyclohexyl methacrylate, dicyclopentyl acrylate, dicyclopentyl methacrylate, isobonyl acrylate, isobornyl methacrylate, phenyl and halogen substituted phenyl acrylate, phenyl and halogen substituted phenyl methacrylate, benzyl and halogen substituted benzyl acrylate, benzyl and halogen substituted benzyl methacrylate , 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, β-methyl glycidyl acrylate, β-methyl glycidyl methacrylate,
Known compounds such as phenylglycidyl acrylate, phenylglycidyl methacrylate, bisphenol A-monoglycidyl ether acrylate, bisphenol A-monoglycidyl ether methacrylate, allyl acrylate, and allyl methacrylate are exemplified.

One of these B components may be used alone, or two or more may be used in combination.

The content ratio of these A component and B component is as follows:
The component B is preferably used in an amount of 5 to 82 parts by weight based on 100 parts by weight of the component A. More preferably, the content is 17 to 54 parts by weight.

When the ratio of the component B to the component A is less than 5 parts by weight, the viscosity of the composition becomes high, and the workability of pouring the composition into a molding die is reduced. Needless to say, the surface accuracy of the obtained polymer is lowered, and the heat resistance of the obtained polymer is lowered. On the other hand, when the proportion of the component B exceeds 82 parts by weight, the mechanical strength, impact resistance, surface hardness, and chemical resistance of the obtained polymer decrease.

In other words, when the ratio of the component B to the component A is within the above range, the viscosity of the composition becomes a viscosity suitable for injection into a mold, and the mechanical strength of the obtained polymer is, of course, high. , Impact resistance, surface hardness, and chemical resistance become preferable characteristics. When the above-mentioned more preferable range is satisfied, the viscosity of the composition becomes a preferable viscosity by the above-mentioned injection, and, of course, the above-mentioned respective characteristics of the obtained polymer. Are more preferable characteristics.

The compound (C) represented by the general formula (1) used as a photopolymerization initiator in the present invention includes bis (2,6-dimethoxybenzoyl) -2,
4,4-trimethylpentylphosphine oxide, bis (2,6-dimethylbenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,4
6-trimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,6-dichlorobenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,6-dimethylbenzoyl) ) Phenylphosphine oxide, bis (2,6-dimethoxybenzoyl) phenylphosphine oxide,
Bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, bis (2,6-dichlorobenzoyl) phenylphosphine oxide, and the like.

One of these photopolymerization initiators may be used alone, or two or more thereof may be used in combination.

The proportion of the photopolymerization initiator to be used is preferably 0.001 to 1 part by weight based on 100 parts by weight of the polymerizable monomer (mixture of the above components A and B). More preferably, the content is 0.003 to 0.5 parts by weight.

If the ratio of the component C to 100 parts by weight of the mixture of the components A and B exceeds 1 part by weight, the progress of the polymerization is accelerated, so that it is difficult to control the polymerization, and the internal uniformity of the obtained polymer is reduced. Not only does it get worse, but also the hue. On the other hand, if the ratio is less than 0.001 parts by weight,
The composition cannot be polymerized sufficiently. In other words, when the proportion of the component C is in the above range, polymerization occurs and the polymerization is easily controlled, and the internal uniformity and hue of the obtained polymer are also favorable. When the content is in the above more preferable range, polymerization occurs and the polymerization is more easily controlled, and the internal uniformity and hue of the obtained polymer are more preferable.

The ultraviolet absorber (component D) used in the present invention is selected from a benzophenone ultraviolet absorber or a benzotriazole ultraviolet absorber. Specific examples include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone,
Benzophenone-based compounds such as 2-hydroxy-4-octoxybenzophenone, 2- (2′-hydroxy-5 ′)
-Methylphenyl) benzotriazole, 2- (2'-
Hydroxy-3 ′, 5′-ditert-butylphenyl) benzotriazole, 2- (2′-hydroxy-
Benzotriazole-based compounds such as 5′-tert-octylphenyl) benzotriazole.

One of these ultraviolet absorbers may be used alone, or two or more thereof may be used in combination.

The proportion of the ultraviolet absorber (D component) is preferably 0.01 to 3 parts by weight with respect to 100 parts by weight of the polymerizable monomer (mixture of the component A and the component B). More preferably, the content is 0.03 to 1 part by weight.

When the proportion of the component D exceeds 3 parts by weight with respect to 100 parts by weight of the mixture of the components A and B, the composition cannot be cured sufficiently or the internal uniformity of the polymer deteriorates. . On the other hand, if the proportion is less than 0.01 parts by weight, more excellent ultraviolet ray cut properties cannot be obtained, and the light resistance of the obtained polymer cannot be further improved. In other words, when the proportion of the D component is within the above range, the internal uniformity of the obtained polymer can be further improved, and the light resistance can be further improved.

In the present invention, used as a thermal polymerization initiator,
Examples of the organic peroxide (component E) having a 10-hour half-life temperature in the range of 45 to 100 ° C. include tertiary-butylperoxy neodecanoate, tertiary-butylperoxyisobutyrate, and tertiary-butylperoxy. −
Examples include peroxyesters such as 2-ethylhexyl monocarbonate, and diacyl peroxides such as 3,5,5-trimethylhexanoyl peroxide, lauroyl peroxide, and benzoyl peroxide.

One type of these thermal polymerization initiators may be used alone, or two or more types may be used in combination.

The proportion of the thermal polymerization initiator (component E) is preferably 0.1 to 3 parts by weight based on 100 parts by weight of the polymerizable monomer (mixture of component A and component B). . More preferably, the content is 0.3 to 1 part by weight.

When the proportion of the component E exceeds 3 parts by weight with respect to 100 parts by weight of the mixture of the components A and B, not only the internal uniformity of the obtained polymer is deteriorated, but also the hue and mechanical strength are deteriorated. . On the other hand, when the proportion is less than 0.1 part by weight, the composition cannot be sufficiently polymerized by heating. In other words, when the ratio of the E component is within the above range,
Thermal polymerization can be performed, the internal uniformity of the obtained polymer can be improved, and the hue and mechanical strength can be improved.

The polymerization composition of the present invention may contain, if necessary, a polymerization regulator, a polymerization accelerator, a release agent, an antioxidant, an anticolorant, an antifogging agent, an antistatic agent, a dye, a pigment, a fragrance, etc. Various stabilizers and additives can be blended.

In the method for producing a lens of the present invention, when producing a lens using the above-described actinic ray-curable composition of the present invention, a step of putting the composition into a mold for producing a lens; The method includes irradiating the composition placed in the mold with light having a wavelength of 300 nm or more, and heating the composition, which is performed as necessary for the composition placed in the mold. And

As a light source for obtaining such light,
For example, a chemical lamp, a xenon lamp, a low-pressure mercury lamp, a high-pressure mercury lamp, a metal halide lamp, and the like can be given.

In practicing the invention of the method for producing a lens, it is preferable that the light applied to the composition is light obtained by blocking (cutting) or attenuating light having a wavelength shorter than 380 nm. Wavelength 380-43
Light including light in the 0 nm band is preferably used.

The reason is that the C component used in the present invention is:
As will be described later with reference to FIG. 1 and FIG.
It shows a remarkable absorption at 0 nm, but has a wavelength of 380 to 430.
It also shows some absorption in light of nm. However, the wavelength 30
When the composition is irradiated with light having a wavelength of 0 to 340 nm, since the light has a short wavelength, heat is easily generated when the composition is cured, and the deep curability is easily deteriorated. So this C
In order to mainly actively use the absorption band of the component at a wavelength of 380 to 430 nm, it is preferable to irradiate light having a wavelength shorter than 380 nm, which is cut or attenuated. By doing so, it is possible to reduce the heat generation when the composition is cured and to improve the deep part curability, as compared with the case where light including light having a wavelength of 300 to 380 nm is used.

In order to cut or attenuate light having a wavelength shorter than 380 nm, the light emitted from the light source may be passed through a filter that cuts or attenuates light having a wavelength shorter than 380 nm, for example.

In practicing the invention of the method for producing a lens, when a composition according to the invention of the present application and containing a component E as a thermal polymerization initiator is used, the composition is heated. A heating step may be further performed. Specifically, after the step of irradiating the composition with light,
A method of performing the step of heating the composition; a method of performing a step of preliminarily heating the composition before the step of irradiating the composition with light; and heating the composition simultaneously with irradiating the composition with light. Any of the methods can be performed. However, it is preferable to carry out a heating step after the step of irradiating the composition with light to polymerize it, from the viewpoint of performing curing that can improve the internal uniformity.

The temperature in the heating step may be set to an arbitrary temperature in consideration of the decomposition temperature of the used organic peroxide (E component) and the surface hardness of the obtained polymer. Further, the heating temperature may be constant, or may be a variable temperature condition in which a heating condition or a cooling condition is determined by a predetermined condition, that is, a so-called pattern method.

As the actinic ray in the present invention, electromagnetic waves such as ultraviolet rays, visible rays, infrared rays, electron beams, X-rays, and gamma rays can be used, but from the viewpoints of safety, cost, efficiency, etc. It is preferable to use an electron beam.

[0054]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The actinic ray-curable composition of the present invention is preferably used as a lens molding composition. In particular, it is preferable to use the composition as a composition for molding a lens substrate of a spectacle lens.

Here, the lens substrate is the eyeglass lens itself. That is, it is the spectacle lens itself excluding other components provided on the lens substrate in order to improve the durability and optical characteristics of the spectacle lens.

The other constituents here are one or more selected from, for example, a hard coat layer, a primer layer, an antireflection film, a water-repellent film and the like.

It is preferable that a hard coat layer, a primer layer, an antireflection film and a water-repellent film are partially or entirely provided on a lens substrate formed using the actinic ray-curable composition of the present invention.

As the hard coat layer, an organosilicon compound represented by the following general formula (I) or a hydrolyzate thereof is preferably used. However, in the formula (I), R
¹ is a functional group or an unsaturated double bond having 4 to 1 carbon atoms
R ² is a hydrocarbon group having 1 to 6 carbon atoms or a halogenated hydrocarbon group, and R ³ is an organic group having 1 to 4 carbon atoms.
Wherein a and b are each 0 or 1, and a + b
Is 1 or 2.

R ¹ _a R ² _b Si (OR ³ ) _{4- (a + b)} (I) Among the compounds represented by the general formula (I), R ¹ has an epoxy group as a functional group Those are also called epoxysilanes.

Specific examples of epoxysilane include, for example, γ-glycidoxypropyltrimethoxysilane, γ
-Glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxyethoxysilane, γ-glycidoxypropyltriacetoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane , Β- (3,4-
Epoxycyclohexyl) ethyltriethoxysilane and the like.

Examples of the compounds represented by the general formula (I) other than those in which R ¹ has an epoxy group as a functional group (including those in which a = 0) include the following. Can be

Methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltrimethoxyethoxysilane, γ-methacryloxypropyltrimethoxysilane, aminomethyltrimethoxysilane, -Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, 3,3,3-trifluoropropyl Various trialkoxysilanes such as trimethoxysilane,
Trisiloxysilane or trialkoxyalkoxysilane compounds.

When these compounds are used as a material for the hard coat layer, it is possible to add inorganic fine particles for improving the hardness, preventing interference fringes, and imparting an antistatic effect. Examples of the inorganic fine particles include zinc oxide, silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, tin oxide, beryllium oxide, antimony oxide, tungsten oxide, cerium oxide, iron oxide, and composite fine particles of tin oxide and tungsten oxide. Fine particles of inorganic fine particles can be used.

These fine particles can be used not only alone but also in a mixed or solid solution state of two or more kinds, if necessary. The mixture according to the present invention refers to a state in which a plurality of different substances are present while maintaining the structure of each substance. Are formed and exist.

In particular, titanium oxide, antimony oxide,
Tungsten oxide, cerium oxide, zirconium oxide,
When tin oxide is used, the refractive index of the composition can be increased, and when a substrate having a high refractive index is used, generation of interference fringes can be suppressed.

The particle diameter of the fine particles is preferably 1 to 200 nm, particularly preferably 5 to 100 nm. If it is smaller than this, the production is difficult, the stability of the fine particles themselves is poor, and the effect is small. If it is larger than this, the stability of the coating composition, the transparency and the smoothness of the coating film, etc. will be reduced.

In addition to the above components, if necessary, for example, for the purpose of improving the adhesion to the substrate (molded product) on the side to be coated, or for the purpose of improving the coating composition of the hard coat layer (including the coating solution) ) May be used in combination for the purpose of improving the stability of the above.

Examples of the additives include a pH adjuster, a viscosity adjuster, a leveling agent, a matting agent, a stabilizer, an ultraviolet absorber, an antioxidant and the like.

The reaction after application of the coating liquid is promoted,
For curing at a low temperature, the following curing catalyst can be used. By curing at a low temperature, the influence of heat on the lens substrate can be reduced.

The curing catalyst is obtained by polymerizing a vehicle component to obtain a curing catalyst.
In order to reduce the time required to form a coating film having a three-dimensional network structure, it is used as needed (however, one that impairs the stability of the coating composition is not preferred). Is used.

(1) Amines: monoethanolamine,
Diethanolamine, isopropanolamine, ethylenediamine, isopropylamine, diisopropylamine, morpholine, triethanolamine, diaminopropane, aminoethylethanolamine, dicyandiamide, triethylenediamine, 2-ethyl-4-methylimida fine particles.

(2) Various metal complex compounds: General formula: AlX
_n An aluminum chelate compound represented by Y3 _-n . However, in the formula, X is OL (L is a lower alkyl group), Y is at least one ligand selected from the general formula M1COCH ₂ OM2 (M1 and M2 are lower alkyl groups) and M1COCH ₂ COOM2, n is 0, 1 or 2.

Particularly useful chelate compounds include aluminum acetylacetonate, aluminum bisethylacetoacetate monoacetylacetonate, and aluminum di-n-ethyl acetate from the viewpoints of solubility, stability, and catalyst curing.
-Butoxide-monoethylacetoacetate, aluminum-di-iso-propoxide-monomethylacetoacetate and the like.

In addition, chromium acetylacetonate, titanyl acetylacetonate, cobalt acetylacetonate, iron (III) acetylacetonate, manganese acetylacetonate, nickel acetylacetonate, E
DTA, and complex compounds of Al, Fe, Zn, Zr, and Ti.

(3) Metal alkoxides: aluminum triethoxide, aluminum tri n-propoxide, aluminum tri n-butoxide, tetraethoxy titanium, tetra n-butoxy titanium, tetra i-propoxy titanium.

(4) Organic metal salts: sodium acetate, zinc naphthenate, cobalt naphthenate, zinc octylate, tin octylate.

(5) Perchlorates: magnesium perchlorate and ammonium perchlorate.

(6) Organic acid or anhydride thereof: malonic acid,
Succinic acid, tartaric acid, adipic acid, azelaic acid, maleic acid, O-phthalic acid, terephthalic acid, fumaric acid, itaconic acid, oxaloacetic acid, succinic anhydride, maleic anhydride,
Itaconic anhydride, 1,2-dimethylmaleic anhydride,
Phthalic anhydride, hexahydrophthalic anhydride, naphthalic anhydride.

(7) Lewis acid: ferric chloride, aluminum chloride.

(8) Metal halides: stannous chloride, stannic chloride, tin bromide, zinc chloride, zinc bromide, titanium tetrachloride, titanium bromide, thallium bromide, germanium chloride,
Hafnium chloride, lead chloride, lead bromide.

These curing catalysts may be used alone or in combination of two or more. Among these curing catalysts, an aluminum chelate compound is one of the preferred catalysts.

The abrasion resistance of the lens substrate surface obtained by curing the actinic ray-curable composition of the present invention may be lower than that obtained by curing a conventional thermosetting resin. Therefore, by forming the hard coat layer containing the organosilicon compound on the lens substrate according to the present invention in this way, the scratch resistance of the lens substrate can be further improved. A lens with improved properties can be easily manufactured.

However, when the hard coat layer is formed by a wet method, a coating solution for the hard coat layer must be prepared in accordance with the difference in the refractive index of the lens substrate and other film performances. It is necessary to prepare it, and there may be a problem that the manufacturing cost increases. Further, there is a case where the amount of waste of the coating liquid is increased and the cost for the material is increased. Instead of such a wet method, a hard coat film can be formed by a dry CVD method. If a hard coat film is formed by the CVD method, a lens with lower cost and excellent scratch resistance can be manufactured more easily.

The hard coat layer formed by the CVD method is formed of a material containing Si and O. Preferably, a modified layer containing at least one of a Si-based compound and / or a Ti-based compound and having a refractive index varying in the thickness direction or a modified layer having a composition ratio of a substance in the layer varying. Preferably, it is formed as a coat layer. Also,
A modified layer whose refractive index is changed in the thickness direction is provided on the base material, has a relatively thicker film than the modified layer, and the refractive index is constant, and Si and A hard coat layer containing O can be formed by a CVD method.

By providing the modified layer, the impact resistance is also improved. This is because the internal stress of the hard coat layer was increased because the thickness of the conventional hard coat layer was 3 μm or more, whereas the modified layer as in the present invention was formed between the substrate and the hard coat layer. This is considered to be because the internal stress remaining in the hard coat layer can be reduced by providing the intermediate layer. Therefore, in order to reduce internal stress,
The effect that cracks and the like caused by heat resistance can be avoided is also obtained.

Examples of the organic compound containing Si used in the production process of the modified layer and the hard coat layer include tetraethoxysilane, dimethoxysilane, methylmethoxysilane, tetramethoxysilane, ethyltrimethoxysilane, diethoxydimethylsilane, methyltrisilane. Ethoxysilane and the like are preferably used.

The organic compounds containing Ti used in the step of forming the modified layer include tetramethoxytitanium, tetraethoxytitanium, tetraisopropoxytitanium, tetra-n-propoxytitanium, tetra-n-butoxytitanium, tetraisobutoxytitanium. Titanium, tetra-se
C-butoxytitanium, tetra-t-butoxytitanium, tetradiethylaminotitanium and the like are preferably used.

One of these organic compounds containing Si and Ti may be used alone, or two or more thereof may be used in combination.

The thickness of the hard coat layer is preferably larger than 0.4 μm and smaller than 5 μm. In addition, the thickness of the denatured layer is more than 100 nm and preferably less than 900 nm.

It is preferable to provide an antireflection film on the hard coat film. This antireflection film is preferably, for example, an antireflection film made of an inorganic oxide formed by a vacuum evaporation method. In this case, a lens having an excellent antireflection effect and an excellent appearance can be manufactured. Materials used for the antireflection film include silicon oxide, titanium oxide, zirconium oxide, and aluminum oxide.

It is preferable to form a primer layer between the lens substrate and the hard coat layer. By providing the primer layer, the adhesion between the lens substrate and the hard coat layer can be improved, and further, the impact resistance of the lens made of the actinic ray-curable composition can be improved.

As a material for the primer layer, a polyurethane resin, an epoxy resin, a polyacetal resin or the like is preferable.

The solution containing the urethane material can be used as a coating solution for forming a primer layer. Examples of the urethane solution include a solution containing an active hydrogen-containing compound and a polyisocyanate.

Here, the active hydrogen-containing compounds include alkylene glycols, polyalkylene glycols,
Examples thereof include polyalkylene adipates, polybutadiene glycols, poly (alkylene carbonate) s, and silicone polyols, and other known active hydrogen-containing compounds can also be used.

As examples of the polyisocyanate, an aromatic diisocyanate, an aliphatic diisocyanate, a block type polyisocyanate and the like can be used.

The urethane solution mentioned here may be a mixture of an active hydrogen-containing compound and a polyisocyanate, or a polymer. Further, an emulsion containing urethane as a main component may be used.

It is also possible to form a primer layer comprising a crosslinked polyvinyl acetal. The primer layer made of polyvinyl acetal dissolves polyvinyl acetal as a main component, a hydrolyzable organosilane compound or a hydrolysis condensate thereof, an aluminum or titanium alkoxide compound or an aluminum or titanium alkoxide diketonate compound, and a curing catalyst. It can be formed by applying the primer composition thus obtained to the surface of a plastic lens and subjecting it to heat treatment.

Examples of the polyvinyl acetal that can be used include, for example, a substance represented by the following general formula (2).

[0099]

Embedded image

Wherein R ¹ is a hydrogen atom or a carbon atom
A is an alkyl group having an acetal group, and a is a composition of a repeating unit having an acetal group (fraction of constituent units).
90 and b are the compositions of the repeating units having an -OH group (fraction of the constituent units), and 10 to 90; c are the compositions of the repeating units having an acetyl group (fraction of the constituent units), and
0 and a + b = 100. Particularly preferred is polyvinyl butyral in which the alkyl group has 3 carbon atoms.
An acetalization degree of 10 to 90% can be used, and a polyvinyl acetal having an acetalization degree of 20 to 80% is preferable.

When the degree of acetalization is less than 10%, the improvement in impact strength is insufficient. In addition, it is difficult to synthesize polyvinyl acetal having an degree of acetalization of 90% or more. A decrease in adhesion is expected.

The degree of polymerization of polyvinyl acetal is preferably 5,000 or less, more preferably 10
0 to 3,000. If the degree of polymerization is too high, it is difficult to dissolve in a solvent, and it is difficult to synthesize a polyvinyl acetal having an optimal acetalization degree. Conversely, if the degree of polymerization is too low, the improvement in impact strength will be insufficient.

The acetyl group in the polyvinyl acetal of the general formula (2) is not an essential component, but a small amount of the acetyl group remaining since the polyvinyl alcohol as a raw material of the polyvinyl acetal is synthesized by hydrolysis of polyvinyl acetate. It is.

The amount of polyvinyl acetal in the composition for forming a primer layer (also referred to as a primer composition) is 1 to 20% by weight, preferably 1 to 10% by weight. If the amount of the polyvinyl acetal added is too large, the viscosity of the primer composition becomes too high, making it difficult to coat the plastic optical component, and the primer coating layer becomes too thick, and the uniformity of the coated surface is lost. Conversely, if the added amount of polyvinyl acetal is too small, the primer coating layer will be too thin and the improvement in impact strength will be insufficient.

The amount of the curing catalyst added to the primer composition is 0.002 to 1% by weight, preferably 0.005% by weight.
１1% by weight.

The thickness of the primer layer is 0.1 to 5 μm, preferably 0.2 to 3 μm after the thermosetting. If the thickness of the primer layer is less than 0.1 μm, the impact resistance is not sufficiently improved, and if it is more than 5 μm, there is no problem in terms of the impact resistance, but the heat resistance and surface accuracy are reduced.

The primer solution may contain inorganic fine particles such as those added to the hard coat film. As these inorganic fine particles, commercially available fine particles dispersed in water or an organic solvent can be used as they are.

The average particle diameter of the inorganic fine particles or the composite of these inorganic oxides is 1 to 300 nm, preferably 1 to 300 nm.
５０50 nm. If the average particle diameter exceeds 300 nm, fogging of the lens occurs due to light scattering.

The addition amount of the inorganic oxide fine particles in the primer composition is 0.1 to 30% by weight as a solid content concentration, but the refractive index of the cured primer film matches or is very close to the refractive index of the plastic lens. The type and the amount of the inorganic oxide fine particles are adjusted so as to be as follows.

In the case where the refractive index is as high as 1.60 or more, TiO ₂ , ZrO ₂ , Fe ₂ O ₃ , Sb ₂ , which are high in refractive index, are relative to 1 part by weight of polyvinyl acetal.
_{O 5, SnO 2, CeO 2} , preferably WO ₃ the inorganic oxide fine particles or complexes thereof, such as the addition of 1 to 5 parts by weight.

As a method for forming the primer layer, a dry method such as a vacuum deposition method can be used. Thereby, a lens having improved impact resistance can be easily obtained by the actinic ray-curable composition.

It is preferable to provide a water-repellent film as the uppermost layer. This is preferable because the prevention of drainage of the lens increases. As a material of the water-repellent layer, an organic polysiloxane-based polymer or an organic-containing cured product made of a polymer obtained by polymerizing a perfluoroalkyl base material-containing compound is preferably used. Silazane compounds having an amino group), siloxane compounds, and alkoxy compounds having a fluorine group can be used. As a forming method, it can be formed by an immersion method, a vacuum method such as a dry method, a CVD method, a sputtering method, or the like. This makes it possible to easily obtain a lens in which drainage is prevented by the actinic ray-curable composition.

Further, it is possible to deposit a dye on a lens substrate molded with the actinic ray-curable composition of the present invention while controlling the thickness of the deposited film using, for example, a quartz film thickness gauge. It is also possible to control the coloring density with an optical film thickness meter. By vapor-depositing a dye on a substrate using these film thickness meters, the concentration can be easily controlled, and coloring can be performed with good reproducibility.

[0114]

The present invention will be described in more detail with reference to the following examples. However, the materials used in the examples described below, the amounts used, and numerical conditions such as temperature and time as manufacturing conditions are merely examples within the scope of the present invention. Therefore, the present invention is not limited to the following examples. In the following examples, "parts" means "parts by weight".

1. Example 1 The following two compounds are prepared as the component A. That is, 40 parts of 2,2-bis [(4-methacryloxy) phenyl] propane are prepared as the A1 component, and 45 parts of 2,2-bis [(4-methacryloxyethoxy) phenyl] propane are prepared as the A2 component.

As component B, 15 parts of glycidyl methacrylate are prepared.

As the component C, bis (2,2) wherein R1 in the above formula (1) is a methyl group and R2 is a phenyl group.
Prepare 0.005 parts of (4,6-trimethylbenzoyl) phenylphosphine oxide.

As the D component, 0.03 parts of 2-hydroxy-4-methoxybenzophenone is prepared.

As component E, 0.5 part of tertiary-butyl peroxyisobutyrate is prepared.

The components B to E prepared in Example 1 were used.
The components will be referred to as B1, C1, D1, and E1 components, respectively, to distinguish them from the components used in Examples 2 to 4 and Comparative Examples 1 and 2 below.

The absorption characteristics of the C1 component used in Example 1 are measured. FIG. 1 shows this C1 component, namely, bis (2,4,
It is the figure which showed the molar extinction coefficient with respect to the wavelength of 300-450 nm light of 6-trimethylbenzoyl) phenylphosphine oxide. The characteristic I in FIG. 1 corresponds to the characteristic.

In FIG. 1, the horizontal axis represents the wavelength (nm).
And the vertical axis represents the molar extinction coefficient (1 / mol-cm). Further, FIG. 1 shows the T
The absorption characteristics of PO are shown as characteristics II, and the absorption characteristics of photopolymerization initiators F1 and F2 used in Comparative Examples 1 and 2 are shown as characteristics III and IV, respectively.

FIG. 2 shows wavelengths 360 to 44 in FIG.
It is the figure which expanded the part of 0 nm band further. Notation is
It is the same as FIG.

From FIGS. 1 and 2, the C1 component has a wavelength of 3
It has absorption in the band of 00 to 380 nm like TPO. However, it can be seen that the C1 component has a characteristic that absorption at a wavelength of 390 nm or more is larger than that of TPO.

Next, the A1 component, A2 component and B1
The above components C1 to E1 are added to the mixture of the components, and sufficiently stirred and defoamed to obtain the composition of Example 1.

Next, the power of the spectacle lens-0.00D
(Center thickness 2.0mm), -6.00D (Center thickness 1.1m)
The two glasses are each held with an adhesive tape to form a mold so as to form a gap giving m). Note that the glass to be used is a glass having good transmittance of each wavelength light from the ultraviolet region to the visible light region, here, quartz glass.

Next, the above prepared composition of Example 1 is injected into the gap of the mold. Then, the composition injected into the mold is irradiated with light from a metal halide lamp having an output of 80 w / cm in air for one minute.

However, this light irradiation is performed with a filter provided between the composition and the lamp, which largely attenuates light having a wavelength shorter than 380 nm. This filter is formed by depositing a metal film on quartz glass. FIG. 3 shows the spectral transmittance characteristics of this filter. FIG. 3 shows the wavelength (nm) on the horizontal axis and the transmittance (%) on the vertical axis. According to the light irradiation conditions, the composition includes:
Light having a wavelength shorter than 380 nm is not substantially irradiated,
Light including light having a wavelength of 380 to 440 nm (actually, a wavelength of 38
It can be understood that light (including light from 0 nm to visible light) is irradiated.

Next, this sample is heated at 110 ° C. for 1 hour in an air oven. After that, remove this composition from the mold (because polymerization is proceeding, hereinafter, polymer),
The polymer is annealed at 120 ° C. for 1 hour in an air oven. The polymer thus treated is evaluated by the following method.

: Evaluation of optical distortion Center thickness 1.1 giving diopter -6.00D of spectacle lens
mm sample is observed with a Toshiba strain tester SVP-100. (○) No optical distortion (△) Optical distortion (small distortion) (×) Optical distortion (large distortion)

: Evaluation of surface accuracy Center thickness 1.1 giving diopter -6.00D of spectacle lens
The center of the mm sample is visually observed. (○) Unbent (△) Slightly curved (x) Bent The evaluation is based on the above criteria.

: Evaluation of light transmittance Center thickness of 2.0 for giving a power of -0.00D for spectacle lens
The light transmittance at a wavelength of 500 nm for a concave lens of mm is measured.

Evaluation of Appearance The appearance of each molded sample is visually observed.

The composition of the composition of Example 1, the wavelength used at the time of light irradiation, and the results of the above-described evaluation experiments are shown in the column of Example 1 in Table 1 below. Table 2 below shows the material names of the components used in Example 1 and the material names of the components used in the following Examples and Comparative Examples.

[0135] 2. Example 2 As the A component, 2,2 which is the A2 component used in Example 1
-Prepare 80 parts of bis [(4-methacryloxyethoxy) phenyl] propane.

As the component B, the following two compounds are prepared. That is, 10 parts of glycidyl methacrylate, which is the B1 component used in Example 1, and B
10 parts of isobornyl methacrylate are prepared as two components.

As the C component, 0.005 parts of bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide (this is referred to as a C2 component) is prepared.

The C2 component is a C component in which R1 in the above formula (1) is a methoxy group and R2 is a 2,4,4-trimethylpentyl group.

As the D component, 2- (2′-hydroxy-
0.03 parts of 5′-tert-octylphenyl) benzotriazole (this is referred to as “D2 component”) is prepared.

As the E component, tertiary-butylperoxy-2-ethylhexyl monocarbonate (this is referred to as E
Prepare 0.5 parts (referred to as two components).

The components A2, B1, B2, C
Mix two components, D2 component and E2 component,
The composition of Example 2 is obtained by defoaming.

The composition of Example 2 was molded under the same conditions as in Example 1, and the polymer obtained by this molding was evaluated by the same evaluation method as in Example 1.

The composition of the composition of Example 2, the wavelength used during light irradiation, and the results of the evaluation experiments are shown in the column of Example 2 in Table 1.

[0144] 3. Example 3 The composition of Example 1 is used. However, a filter that attenuates light having a wavelength shorter than 380 nm is not used at the time of light irradiation for molding the composition. That is, a wavelength of 300 to
Irradiation with light including 380 nm light is performed. Otherwise, Example 1
In the same manner as described above, the molding and the evaluation of the polymer are performed. The results are shown in the column of Example 3 in Table 1.

4. Example 4 The composition of Example 2 is used. However, a filter that attenuates light having a wavelength shorter than 380 nm is not used at the time of light irradiation for molding the composition. That is, a wavelength of 300 to
Irradiation with light including 380 nm light is performed. Otherwise, Example 2
In the same manner as described above, the molding and the evaluation of the polymer are performed. The results are shown in the column of Example 4 in Table 1.

[0146] 5. Comparative Example 1 Bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, which is the C1 component of Example 1, is 0.00
Instead of using 5 parts, 2,2-
0.01 part of dimethoxy-1,2-diphenylethan-1-one (this is referred to as F1 component) is used. Otherwise, molding and evaluation of the polymer are performed in the same manner as in Example 1. The results are shown in the column of Comparative Example 1 in Table 1.

The absorption characteristics of the F1 component are shown in FIG.
This is as shown in the characteristic III of FIG. That is,
It has absorption only up to a wavelength of 400 nm and, of course, has a smaller absorption coefficient than the photopolymerization initiator used in the examples.

6. Comparative Example 2 Bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide which is the C1 component of Example 1 0.00
Instead of using 5 parts, 0.01 part of 1-hydroxycyclohexyl phenyl ketone (this is referred to as F2 component) is used as a photopolymerization initiator. In addition, a filter that attenuates light having a wavelength shorter than 380 nm is not used when irradiating the composition with light. That is, the wavelength 300
Irradiation including light having a wavelength of 380 nm is performed. Otherwise, molding and evaluation of the polymer are performed in the same manner as in Example 1. The results are shown in the column of Comparative Example 2 in Table 1.

The F2 component is disclosed in Japanese Unexamined Patent Publication No.
No. 111 is one of the photopolymerization initiators. The absorption characteristic of the F2 component is as shown in the characteristic IV in FIGS. That is, the wavelength 390
It has absorption only up to nm and, of course, has a smaller absorption coefficient than the photopolymerization initiator used in the examples.

7. Comparative Example 3 Bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide which is the C1 component of Example 1 0.00
Instead of using 5 parts, 0.005 parts of TPO (this is referred to as F3 component) is used as a photopolymerization initiator. Otherwise, molding and evaluation of the polymer are performed in the same manner as in Example 1. The results are shown in the column of Comparative Example 3 in Table 1.

8. Comparative Example 4 In the configuration of Comparative Example 3, the thermal polymerization initiator E1 was not used, and the composition was cured only by light irradiation. Otherwise, molding and evaluation of the polymer are performed in the same manner as in Example 1.
However, in the case of Comparative Example 4, the measurement of optical distortion and the like could not be performed because only the light irradiation was in a gel state.

9. DISCUSSION From the results in Table 1, the optical distortion was determined in Examples 1 and 2
It can be seen that is the most excellent case. Example 3 and Example 4 are the same as Example 1 and Example 2 except that no filter was used at the time of light irradiation. In Examples 3 and 4, the optical distortion is worse than that of Examples 1 and 2, It turns out that it is better than Example 1 and Comparative Example 2.

It can be seen that the surface accuracy is the most excellent in Examples 1 and 2. Example 3 and Example 4 are the same as Example 1 and Example 2 except that no filter was used at the time of light irradiation. In the case of Examples 3 and 4, the surface accuracy is worse than that of Examples 1 and 2, It turns out that it is better than Example 2.

It can be seen that there is no difference in light transmittance between the examples and the comparative examples.

Although there is no difference in appearance between each example and Comparative Example 2, it can be seen that Comparative Example 1 is yellowish.

Comparative Example 3, in which TPO was used as the photopolymerization initiator, exhibited properties similar to those of Examples 3 and 4. However, in Comparative Example 3, when a lens having a lens power of −6.00D was molded, another problem occurred that a phenomenon in which the molded product was peeled off from the mold during molding frequently occurred.

From these results, it can be seen that the compositions of Examples 1 and 2 are superior to the comparative examples as molding compositions for spectacle lenses.

[0158] Further, as the light for irradiating the compositions of Examples 1 and 2, light obtained by cutting or attenuating light having a wavelength shorter than 380 nm has a smaller optical distortion than the case where it is not used. It can be seen that molding with less surface accuracy is possible.

[0159]

[Table 1]

[0160]

[Table 2]

[0161]

As is clear from the above description, by adjusting the ratio of the component A and the component B, a composition having a viscosity suitable for molding, and further, after polymerization, heat resistance, surface hardness, A composition is obtained that is a polymer in which each of impact resistance, chemical resistance, and mechanical strength is appropriately adjusted.

The photopolymerization initiator represented by the formula (1) has two sites that are cleaved by actinic rays. Therefore, a large amount of radicals effective for the polymerization of the composition are generated, so that the light irradiation time required for curing the composition can be reduced. Therefore, the rise in the temperature of the composition during light irradiation can be suppressed. The photopolymerization initiator represented by the formula (1) also has an absorption in a long wavelength range, specifically, in a wavelength range of 400 to 440 nm. Therefore, a curing process using long-wavelength light is possible. Therefore, it can be said that heat generation during curing of the composition is easily suppressed.

When the actinic ray-curable composition is molded and there is a flaw in the mold, the longer the light irradiation time and the longer the irradiation light contains short-wavelength light, the more the mold is damaged. Is easily transferred to a molded product. Therefore, it becomes a cause of increasing molding defects. To prevent this, it is necessary to replace the mold even when the mold is slightly damaged. However, the consumption rate of the mold is undesirably increased. On the other hand, in the present invention, as described above, since the light irradiation time can be shortened and long-wavelength light can be used, the degree of scratches on the mold, which is a problem in molding, is reduced. Therefore, the effect of reducing the consumption rate of the mold can be obtained.

When an ultraviolet absorber is used, the ultraviolet ray cut property is ensured. Therefore, light resistance is secured.

From these facts, the actinic ray-curable composition of the present invention can be cured in a short period of time and has excellent properties such as internal uniformity, surface accuracy, ultraviolet cut property, transparency and hue. Is obtained.

Further, according to the method for producing a lens of the present application, the actinic ray-curable composition of the present application can be cured as desired, so that the internal uniformity, surface accuracy, ultraviolet ray cutting property, transparency and A cured product having excellent characteristics such as hue can be easily obtained.

[Brief description of the drawings]

FIG. 1 is a diagram illustrating the absorption characteristics of a photopolymerization initiator used in each of Examples and Comparative Examples.

FIG. 2 is a diagram for explaining absorption characteristics of a photopolymerization initiator used in each of Examples and Comparative Examples, and is a diagram particularly showing a part of FIG. 1 in an enlarged manner.

FIG. 3 shows transmittance characteristics of a filter used in the embodiment as a means for blocking or attenuating light having a wavelength shorter than 380 nm.

Claims (4)

[Claims] 1. A component having at least one compound having at least two of at least one of a (meth) acryloyl group and a (meth) acryloxy group in a molecule, and a B component having (meth) An actinic ray curable composition comprising at least one compound having one acryloyl group or (meth) acryloxy group, and at least one compound represented by the following formula (1) as a C component: (Wherein, in the formula (1), n is 2 or 3. R1 is selected from a methyl group, a methoxy group and a chlorine atom, and may be all the same or all different; , N = 3, they may be partially different.
R2 is a 2,4,4-trimethylpentyl group or a phenyl group. ). Embedded image 2. The actinic ray-curable composition according to claim 1, wherein the component B is 5-82 to 100 parts by weight of the component A.
An actinic ray-curable composition, which is contained in a ratio of parts by weight. 3. The actinic ray-curable composition according to claim 1, wherein the component C is contained in a ratio of 0.001 to 1 part by weight with respect to 100 parts by weight of the mixture of the component A and the component B. An actinic ray-curable composition comprising: 4. The actinic ray-curable composition according to claim 1, wherein the D component contains at least one kind of UV absorber selected from a benzophenone UV absorber and a benzotriazole UV absorber. Actinic ray-curable composition.