JP3073556B2 - Method for manufacturing photochromic plastic lens - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a photochromic plastic lens.

[0002]

2. Description of the Related Art A lens utilizing photochromic properties, which is colored by irradiation with short-wavelength light and loses color when irradiated with long-wavelength light, heated or left in a dark place, is known. Glass is used as a sunglass material.

On the other hand, in order to obtain a plastic lens having photochromic properties, for example, it is conceivable to include a photochromic substance in a diethylene glycol bisallyl carbonate resin base material which is well known as an eyeglass lens material. Since a peroxide-based polymerization initiator is used in a large amount at the time of forming a lens, the photochromic property disappears or is significantly reduced, so that there is a problem that a photochromic lens cannot be obtained.

Japanese Patent Laid-Open Publication No. Sho 61-228402 discloses that a photochromic dye-containing resin solution is applied to the diethylene glycol bisallyl carbonate resin substrate and heated to deposit the photochromic dye in the resin film into the substrate. A method of removing the photochromic dye-deficient resin film after infiltration or diffusion, and then applying a cured film is disclosed.Japanese Patent Application Laid-Open No. 62-10604 discloses a method in which a photochromic dye is added to a coating solution. A method for forming a photochromic dye-containing cured film by applying this to a lens is disclosed.

[0005] By the way, the plastic lens has a problem that the surface hardness is inferior in physical properties. As an improvement thereof, for example, Japanese Patent Application Laid-Open No. Sho 61-166824 discloses an acrylic resin containing a hydrolyzate of an organosilicon compound and an epoxy resin. It is disclosed that a polyorganosiloxane-based coating composition comprising a resin compound and an epoxy curing agent is applied and cured.

[0006]

However, the method disclosed in the above-mentioned Japanese Patent Application Laid-Open No. 61-228402 is
In order to obtain a sufficient photochromic concentration, treatment at a high temperature exceeding the heat resistance temperature of the substrate is required, and as a result, there are problems such as roughening of the lens surface and distortion of the lens surface.

Further, the method disclosed in the above-mentioned Japanese Patent Application Laid-Open No. 62-10604 has a limitation in solubility of a photochromic dye in a coating solution, making it difficult to obtain sufficient photochromic properties. Even if the amount of dissolution increases, there is a problem that the physical properties of the photochromic dye-containing cured film are reduced.

Further, the polyorganosiloxane-based cured film disclosed in the above-mentioned Japanese Patent Application Laid-Open No. Sho 61-166824 has the problem that the abrasion resistance to physical cleaning and contact is not sufficient and the surface hardness is insufficient. was there. In addition, when a metal colloid which is a general wear resistance improver is added to this polyorganosiloxane-based cured film, there is a problem that the adhesion to a base resin (especially an acrylic resin) is significantly reduced. Was.

An object of the present invention is to solve the above-mentioned drawbacks of the conventional method for manufacturing a photochromic plastic lens. The first object of the present invention is to have sufficient photochromic properties and satisfy the characteristics as a lens. A second object of the present invention is to provide a method for producing a photochromic plastic lens, which has sufficient photochromic properties, satisfies the characteristics as a lens, and has high surface hardness and excellent abrasion resistance. An object of the present invention is to provide a method for manufacturing a plastic lens.

[0010]

The first object of the present invention is to initiate a peroxide-based polymerization of a monomer mixture containing the following components (a), (b), (c) and (d) as main components. The present invention has been attained by a method for producing a photochromic plastic lens, comprising a step of obtaining a plastic lens having photochromic properties by polymerizing under a polymerization condition not containing an agent. (A) at least one methacrylic monomer selected from a monofunctional methacrylate and a polyfunctional methacrylate; (b) at least one selected from (meth) acrylic acid and a hydroxyl group-containing (meth) acrylate (C) at least one polyfunctional crosslinkable monomer, (d) an effective amount of a photochromic dye. The above second object, a plaque tick lens obtained above was treated non-polymerizable gas atmosphere flop plasma, then applying a coating composition mainly composed of (e) and (f) the following components, This has been achieved by further including a step of curing to form a cured film. (E) an organosilicon compound having a silanol group and an epoxy group, and (f) colloidal silica.

Hereinafter, the present invention will be described in detail. In the present invention, a monomer mixture containing the above-mentioned components (a), (b), (c) and (d) as main components is polymerized under polymerization conditions not containing a peroxide-based polymerization initiator. To obtain a photochromic plastic lens.

The condition that the peroxide-based polymerization initiator is not used is that the photochromic dye of the component (d) is decomposed and the photochromic property disappears or is remarkably reduced when it is contained, as described later. It is because it declines.

The reason why the methacrylic monomer (a) is used as the monomer is to realize excellent optical characteristics such as high transparency and light resistance of the acrylic resin in the obtained plastic lens. In addition, as the methacrylic monomer of the component (a), at least one selected from monofunctional methacrylates and polyfunctional methacrylates is used. Examples of the monofunctional methacrylate include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, ethylhexyl methacrylate, benzyl methacrylate, phenyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, adamantyl methacrylate, and the like. Examples of polyfunctional methacrylates include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate,
Examples thereof include 4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol trimethacrylate, and glycerin dimethacrylate. The preferred content of the component (a) is from 30 to 95% by weight, more preferably from 40 to 95% by weight, based on the total monomer mixture. (A) The proportion of the component is 3 in the total monomer mixture.
When the amount is less than 0% by weight, transparency, light resistance, strength, etc., which are the characteristics of the acrylic resin, are reduced. On the other hand, when the amount exceeds 95% by weight, the content of the monomer (b) which is a monomer having a hydrophilic group is reduced. Due to the relative decrease, the adhesion to the cured film becomes weak.

As the hydrophilic monomer as the component (b), at least one selected from (meth) acrylic acid and a hydroxyl group-containing (meth) acrylate ester is used. In this specification, “(meth) acrylic acid” means both “acrylic acid” and “methacrylic acid”.
Examples of these include acrylic acid, methacrylic acid, hydroxyethyl ester of acrylic acid or methacrylic acid,
Chlorohydroxypropyl ester of acrylic acid or methacrylic acid; The preferred content of the component (b) is 5 to 50% by weight, more preferably 5 to 30% by weight, based on the total monomer mixture. If the proportion of the component (b) is less than 5% by weight of the total monomer mixture, the improvement in adhesion to the cured film is weak, while if it exceeds 50% by weight, the water absorption is increased and the physical properties of the resin surface are reduced. It becomes unstable, rough and pocked, and the like. In addition, the releasability and transferability at the time of shaping deteriorate.

The polyfunctional crosslinkable monomer as the component (c) is a crosslinkable monomer having two or more functional groups. Examples thereof include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, and triethylene glycol dimethacrylate. Polyfunctional methacrylates such as methacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, glycerin trimethacrylate, ethylene glycol diacrylate, triethylene Polyfunctional acrylic ester such as glycol diacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate S, divinylbenzene and the like. The preferred content of the component (c) varies depending on the type thereof, but is generally in the range of 3 to 50% by weight in the total monomer mixture, and is preferably 3 to 30% by weight in the case of ethylene glycol dimethacrylate as an example. When the proportion of the component (c) is less than 3% by weight, the heat resistance becomes insufficient. On the other hand, when the proportion exceeds 50% by weight, the impact resistance is reduced, and cracks and cracks are liable to be generated at the time of mold release. However, it is not preferable because problems such as difficulties arise.

The photochromic dye as the component (d) is soluble in the above-mentioned monomers (a), (b) and (c),
It is necessary that the photochromic property can be maintained even after the polymerization. As such a dye, a spiropyran-based or spirooxazine-based dye is used. Examples of spiropyran-based dyes include indolinospirobenzopyran indole and benzene ring halogen, methyl, ethyl, methylene, ethylene, and various substituents such as hydroxyl group, indolinospironaphthopyran indole and naphthalene ring halogen, methyl, and ethyl. , Methylene, ethylene, each substituent such as a hydroxyl group, indolino spiroquinopyran halogen of the indole ring, methyl, ethyl, methylene, ethylene, each substituent such as a hydroxyl group, indolinospiropyridopyran halogen of the indole ring, methyl , Ethyl, methylene, ethylene, hydroxyl groups and the like. As the spirooxazine dyes, indolino spirobenzoxazine indole and benzene ring halogen,
Methyl, ethyl, methylene, ethylene, each substituent such as a hydroxyl group, indole and naphthalene ring halogen, methyl, ethyl, methylene, ethylene, each substituent such as a hydroxyl group, and indolinospirophenanthrooxazine Halogen of the indole ring, methyl, ethyl, methylene, ethylene, each substituent such as hydroxyl group, indolino spiroquinolinoxazine indole ring halogen, methyl, ethyl, methylene, ethylene,
Examples include substituted groups such as a hydroxyl group, and substituted groups such as halogen, methyl, ethyl, methylene, ethylene, and a hydroxyl group on a piperidine ring and a naphthalene ring of piperidinospironaphthoxazine. Of these, spirooxazine dyes are particularly preferred in terms of light resistance, and the use of an organic nickel stabilizer is more effective. As a commercially available spirooxazine-based dye, Photo. PNO,
Sunmax (a dye-containing acrylic monomer) manufactured by Tsukuba Science Laboratory Co., Ltd. can be mentioned.

The preferred content of the photochromic dye as the component (d) cannot be unambiguously defined because it varies greatly depending on the type of the photochromic dye, as shown in Examples described later. An amount effective for smooth color development, ie,
The amount is selected so that the color density at the time of color development is high and the light transmittance at the time of color erasure is high.

It should be noted that other monomers copolymerizable with the components (a), (b) and (c) can be added to the monomer mixture as long as the effects of the present invention are not impaired. . These monomers include ethyl methacrylate and n-methacrylic acid.
Butyl, ethyl hexyl methacrylate, benzyl methacrylate, phenyl metal acrylate, cyclohexyl methacrylate, isobornyl methacrylate, adamansyl methacrylate, and the like, methyl acrylate, ethyl acrylate, n-butyl acrylate, ethyl hexyl acrylate, Acrylic esters such as cyclohexyl acrylate, benzyl acrylate, phenyl acrylate, and isobornyl acrylate; nuclear-substituted styrenes such as styrene, methyl styrene, dimethyl styrene, chlorostyrene, dichlorostyrene, bromostyrene, and p-chloromethylstyrene And α-methylstyrene, acrylonitrile, methacrylonitrile, maleic anhydride, N-
And substituted maleimides.

In the method for producing a photochromic plastic lens of the present invention, it is preferable to use a cast polymerization method, and usually, thermosetting polymerization is employed. That is, this is a method in which an appropriate amount of a polymerization initiator is added to the monomer mixture, the mixture is injected into a mold, and heat polymerization is performed. As the polymerization initiator at this time,
Azo initiators such as 2,2'-azobisisobutyronitrile and 2,2'-azobis (2,4-dimethylvaleronitrile) can be suitably used. As described above, peroxide-based initiators such as benzoyl peroxide, lauroyl peroxide, and t-butylperoxy-2-ethylhexanoate reduce or eliminate the effect of the photochromic dye. The use of agents should be excluded. The initiator is usually 0.001 to 5% by weight of the total amount of the monomers.
Is preferably used. The heating temperature varies greatly depending on the initiator used, but is usually in the range of 20 to 80 ° C. In addition, polymerization by intense light irradiation is not preferable because the photochromic property may be reduced.

In the present invention, if necessary, a heat stabilizer, an antioxidant, an ultraviolet absorber, a release agent, an antistatic agent, and other dyes may be added to the monomer mixture. .

The photochromic plastic lens obtained according to the present invention is obtained by polymerizing a monomer mixture under conditions not containing a peroxide-based polymerization initiator. d) The photochromic dye as a component remains in the plastic lens without being decomposed. Therefore, it has a so-called photochromic property in which it is colored by irradiation with ultraviolet rays and decolored by being shielded from ultraviolet rays, and is preferably used for sunglasses and the like.

According to the present invention, the photochromic plastic lens obtained as described above can be subjected to a plasma treatment, and further, a coating composition can be applied and cured to thereby improve the surface hardness of the plastic lens. Thus, a photochromic plastic lens having excellent abrasion resistance and abrasion resistance can be obtained.

The conditions for the plasma treatment are slightly different depending on the size, type and shape of the apparatus used. In the present invention, however, the non-polymerizable gas such as air, helium, argon, hydrogen, oxygen, nitrogen, etc. is usually used at 0.01 to 10 Torr. This is performed within 60 seconds in an atmosphere.

The coating and curing treatment of the coating composition on the plastic lens after the plasma treatment is performed as follows.

It is necessary that the coating composition simultaneously contains an organosilicon compound having a silanol group and an epoxy group and colloidal silica. As the organosilicon compound having a silanol group and an epoxy group, a general formula

[0026]

Embedded image

(Wherein, R ₁ is an alkyl group having 1 to 4 carbon atoms, and R ₂ is an alkylene group having 1 to 4 carbon atoms). In the trifunctional organosilicon compound, R _{1 in} the formula is a methyl group, an ethyl group, a propyl group or a butyl group;
Those in which ₂ is a methylene group, an ethylene group, a propylene group or a butylene group are particularly preferred.

On the other hand, as the colloidal silica, a high-concentration water-dispersed colloidal silica (for example, having a SiO ₂ solid content of 40% or more) is preferably used so that excess water is not left after the hydrolysis of the organosilicon compound. It is preferably used. The particle size is preferably about 5 to 30 mμ. In particular, the coating composition used in the present invention exhibits its usefulness when it contains a high concentration of colloidal silica. In this sense, the amount of the colloidal silica in the coating composition is preferably set to 75 mol% (in terms of SiO ₂ solid content) or more based on the total amount of the colloidal silica and the organosilicon compound. Although the curing agent is not particularly limited, an acetylacetone metal complex compound is effective, and among them, an aluminum complex compound of acetylacetone can be used particularly effectively. The amount of addition is sufficient to cure the colloidal silica and the hydrolyzate of the organosilicon compound, for example, 1 to 10 g per 1 mol of the total hydrolyzate of the colloidal silica (in terms of SiO ₂ ) and the organosilicon compound. It is.

An organic acid is used for the hydrolysis of the organosilicon compound of the formula (I). These include acetic acid, formic acid, propionic acid and the like, but it is preferable to use acetic acid in view of the stability of the coating composition. The amount of the organic acid to be added is 5 to 1 mol of the total amount of the colloidal silica and the organosilicon compound.
It is preferably 30 g. If the amount is less than this, gelling of the coating composition is liable to occur. If the amount is more than this, odor becomes strong and workability deteriorates.

Further, in order to make the hydrolysis uniform and to control the degree thereof appropriately, it is preferable to add a suitable solvent to the coating composition. As such a solvent, cellosolves such as methyl cellosolve, ethyl cellosolve, and butyl cellosolve are preferable, and a combination with isopropyl alcohol, butanol and the like is more preferable. The proportion of cellosolve is preferably at least 3% by weight of the total solvent amount, particularly preferably at least 10% by weight. In particular, when the proportion of colloidal silica is large, if the proportion of cellosolve in the solvent is less than 3% by weight of the total solvent, gelation occurs during the preparation of the coating composition, making it difficult to obtain a coating composition.

A silicone surfactant can be added to the coating composition used in the present invention for the purpose of improving the smoothness of the coating film. Further, for the purpose of improving light resistance or preventing deterioration of the coating film, an ultraviolet absorber, an antioxidant, and the like can be added. The coating composition can be applied to the lens substrate by dipping, spin coating, roll coating, spraying, or the like. Curing of the applied coating composition is performed by heat treatment, and the heating temperature is preferably from 40 to 150 ° C, particularly preferably from 80 to 130 ° C. The heating time is preferably 1 to 4 hours.

[0032]

The present invention will be described in more detail with reference to the following examples. In addition, the method of the physical property evaluation in an Example and a comparative example is as follows.

(A) Photochromic properties Judgment was made based on the responsiveness of a change in the transmittance of the lens at the time of ultraviolet irradiation and light shielding by a high-pressure mercury lamp.

(B) Surface Hardness The surface was rubbed 50 times (reciprocatingly) with steel wool # 0000 and an additional load of 1000 g, and the scratch resistance was determined according to the following criteria. A: Almost no damage. B: Very slightly scratched. C: Slightly scratched. D: Many scratches are made.

(C) Adhesiveness The surface of the cured film was cut into squares (10 × 10) at 1 mm intervals, and a cellophane adhesive tape (No.
405) was strongly adhered, and the number of goban eyes remaining after being peeled off sharply in the direction of 90 degrees was examined.

(D) Appearance Transparency, colored state, surface state, etc. were examined by visual observation.

The coating compositions used in Examples 2 to 20 and Comparative Example 1 were prepared as follows. (I) Colloidal silica having a SiO ₂ concentration of 40% (Snowtex-40, water-dispersed silica, manufactured by Nissan Chemical Industries, Ltd.) 2
A solution obtained by adding 2.0 parts by weight of 0.5N hydrochloric acid and 20 parts by weight of acetic acid to 40 parts by weight was stirred at 35 ° C., and 95 parts by weight of γ-glycidoxypropyltrimethoxysilane (trifunctional organosilicon compound) was added. The mixture was added dropwise, stirred at room temperature for 8 hours, and then allowed to stand for 16 hours. To 320 parts by weight of this hydrolysis solution, 80 parts by weight of methyl cellosolve, 1 part of isopropyl alcohol
20 parts by weight, 40 parts by weight of butyl alcohol, 14 parts by weight of aluminum acetylacetone, 0.2 parts by weight of a silicone-based surfactant, and 0.1 parts by weight of an ultraviolet absorber,
After stirring for an hour, the mixture was aged at room temperature for 24 hours to obtain a coating composition. This is designated as coating composition (A). At this time, the amount of colloidal silica in the coating composition was 80 mol% (SiO _{2) based on} the total amount of colloidal silica and γ-glycidoxypropyltrimethoxysilane.
(In terms of solid content).

(Ii) A coating composition (B) was obtained in the same manner as in the preparation of the coating composition (A) except that the amount of γ-glycidoxypropyltrimethoxysilane was changed to 67 parts by weight. At this time, the amount of colloidal silica in the coating composition was 8 based on the total amount of colloidal silica and γ-glycidoxypropyltrimethoxysilane.
It was 5 mol% (in terms of SiO ₂ solid content).

(Iii) A coating composition (C) was obtained in the same manner as in the preparation of the coating composition (A) except that 120 parts by weight of ion-exchanged water was used instead of the colloidal silica. Example 1 70 parts by weight of methyl methacrylate, 10 parts by weight of 2-hydroxyethyl methacrylate, 20 parts by weight of ethylene glycol dimethacrylate, and a spirooxazine-based photochromic dye, Photo. P
NO: 0.01 part by weight, azobis-based chemical product V-700.0 manufactured by Wako Pure Chemical Industries, Ltd. as a radical polymerization initiator
6 parts by weight, 0.05 parts by weight of Tinuvin P (manufactured by Ciba-Geigy) as an ultraviolet absorber, and 0.02 parts by weight of Shin-Etsu Silicone KF353A (manufactured by Shin-Etsu Chemical Co., Ltd.) as a release agent were mixed and dissolved. This mixture was poured into a mold composed of two glass molds and a plastic gasket, placed in a hot-air circulation heating furnace, heated at 37 ° C. for 8 hours, and then heated to 90 ° C. over 8 hours. The mixture was heated for 2 hours to carry out polymerization. The polymer obtained by removing the mold was a highly transparent lens having a diameter of 75 mm, a thickness of 2.0 mm, and a power of 0.00 diopter. Add this to 12
Annealing was performed by heating at 0 ° C. for 2 hours.

The obtained plastic lens had a photochromic property in which it was colored by irradiation with ultraviolet rays, and was erased by being shielded from ultraviolet rays. FIG. 1 shows the responsivity of the transmittance change at 554 nm of this lens at the time of ultraviolet irradiation and light shielding by a high-pressure mercury lamp. The temperature at this time is 2
0 ° C and the UV intensity on the lens surface is USHIO ELECTRIC CO., LTD.
Integrated Light Meter UIT-102 (Receiver UVD365P
It was 1.2 mW when measured in D).

Example 2 The photochromic plastic lens obtained in Example 1 was replaced with a PR made by Yamato Scientific Co., Ltd.
Plasma treatment was performed using -501A under a nitrogen atmosphere of 0.6 Torr for 1 second. Subsequently, the coating composition (A) was applied by a dipping method (pulling speed: 20 cm / min), and this was heated and cured at 120 ° C. for 90 minutes.
As shown in Table 1, the evaluation results of the thus obtained lens with a cured film were excellent in surface hardness, adhesion and appearance. This lens with a cured film has the same photochromic properties as the lens of Example 1, and the response of the change in transmittance at 554 nm of this lens at the time of ultraviolet irradiation and light shielding is the same as that of Example 1. Was. Therefore, it could be suitably used as a photochromic lens for spectacles.

[Examples 3 to 10] A lens with a cured film was prepared and evaluated in the same manner as in Example 2 except that the plasma treatment conditions and the type of the coating composition were changed as shown in Table 1. Was. As shown in Table 1, the surface hardness, adhesion, and appearance were excellent. Further, these lenses with a cured film had photochromic properties and could be suitably used as spectacle lenses. Responsiveness of the change in transmittance at 554 nm of this lens at the time of ultraviolet irradiation and light shielding was equivalent to that of Example 1.

[0043]

[Table 1]

[Examples 11 to 18] A plastic lens was obtained in the same manner as in Example 1 except that the composition of the monomer mixture was changed as shown in Table 2, and plasma treatment was performed in the same manner as in Example 2. Then, a coating treatment was performed to obtain a lens with a cured film. The obtained lens with a cured film was similarly evaluated. The results are as shown in Table 2, surface hardness, adhesion,
The appearance was excellent. Further, these lenses with a cured film had photochromic properties and could be suitably used as spectacle lenses. Responsiveness of the change in transmittance at 554 nm of this lens at the time of ultraviolet irradiation and light shielding was equivalent to that of Example 1.

Comparative Example 1 As shown in Table 2, an attempt was made to produce a plastic lens in the same manner as in Example 1 except that the crosslinkable monomer of the component (c) was not used. Did not have a perfect lens shape.

[0046]

[Table 2]

Example 19 20 parts by weight of 2-hydroxypropyl methacrylate and 10 parts by weight of ethylene glycol dimethacrylate were added to 70 parts by weight of methyl methacrylate.
1.0 parts by weight of 5-chloroindolinospironaphthooxazine as a photochromic dye and azobis-based chemical product V-7 manufactured by Wako Pure Chemical Industries, Ltd. as a radical polymerization initiator
0 0.06 parts by weight, and 0.03 parts by weight of Shin-Etsu Silicone KF353A manufactured by Shin-Etsu Chemical Co., Ltd. as a release agent were added and mixed and dissolved. Polymerization was carried out using this prepared liquid in the same manner as in Example 1, and a surface-hardened film was applied to obtain a highly transparent lens. The lens thus obtained was excellent in surface hardness A and adhesion 100/100. Further, this lens had photochromic properties and could be suitably used as an eyeglass lens. FIG. 2 shows the responsiveness of a change in transmittance at 610 nm of this lens during ultraviolet irradiation and light shielding by a high-pressure mercury lamp. At this time, the temperature was 21 ° C., and the UV intensity on the lens surface was measured using an integrating luminometer UIT-102 (receiver UVD3) manufactured by USHIO INC.
It was 1.2 mW when measured at 65 PD).

Example 20 40 parts by weight of methyl methacrylate, 14 parts by weight of 2-hydroxyethyl methacrylate, 6 parts by weight of ethylene glycol dimethacrylate, and 40 parts by weight of a spirooxazine-based photochromic dye-containing acrylic monomer Sunmax (Tsukuba) Science Research Institute Co., Ltd.
0.20 parts by weight of an azobis-based chemical product V-70 manufactured by Wako Pure Chemical Industries, Ltd. as a radical polymerization initiator, and Shin-Etsu Silicone KF353A manufactured by Shin-Etsu Chemical Co., Ltd. as a release agent.
0.03 parts by weight was added and mixed and dissolved. Polymerization was carried out using this prepared liquid in the same manner as in Example 1, and a surface-hardened film was applied to obtain a highly transparent lens. The lens thus obtained was excellent in surface hardness A and adhesion 100/100. Further, this lens had photochromic properties and could be suitably used as an eyeglass lens. FIG. 3 shows the responsiveness of a change in transmittance at 610 nm of this lens when ultraviolet light is irradiated and light is shielded by a high-pressure mercury lamp. At this time, the temperature was 24 ° C., and the intensity of the ultraviolet light on the lens surface was measured using an integrating photometer UIT manufactured by Ushio Electric Co.
It was 1.2 mW when measured with -102 (receiver UVD365PD).

[0049]

According to the present invention, an acrylic plastic lens having a sufficient photochromic property can be obtained. Further, a favorable cured film having extremely high hardness and excellent adhesion can be formed on the obtained photochromic plastic lens as desired. The photochromic plastic lens obtained by the present invention is extremely useful as a lens for spectacles.

[Brief description of the drawings]

FIG. 1 is a graph showing the response of a change in transmittance at 554 nm of a plastic lens of Example 1 at the time of ultraviolet irradiation and at the time of shading,

FIG. 2 is a graph showing the responsiveness of a change in transmittance at 610 nm of the plastic lens of Example 19 during ultraviolet irradiation and light shielding.

FIG. 3 is a graph showing the response of a change in transmittance at 610 nm of the plastic lens of Example 20 during ultraviolet irradiation and light shielding.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI G02B 1/04 G02B 1/04 1/10 5/23 5/23 1/10 Z (56) References JP-A-62-187784 JP-A-1-161036 (JP, A) JP-A-63-27565 (JP, A) JP-A-3-4201 (JP, A) JP-A-62-239102 (JP, A) JP-A-1-87607 (JP, A) JP-A-62-265317 (JP, A) JP-A-62-192413 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G02C 7 / 10 G02B 1/04 G02B 1/10 G02B 5/23 C08F 220/06 C08F 220/18 C08J 7/00 306 C08J 7/06

Claims (3)

(57) [Claims] 1. Polymerization of a monomer mixture containing the following components (a), (b), (c) and (d) as main components under polymerization conditions not containing a peroxide polymerization initiator. A method for producing a photochromic plastic lens, comprising a step of obtaining a plastic lens having photochromic properties by the method. (A) at least one methacrylic monomer selected from a monofunctional methacrylate and a polyfunctional methacrylate; (b) at least one selected from (meth) acrylic acid and a hydroxyl group-containing (meth) acrylate (C) at least one polyfunctional crosslinkable monomer, (d) an effective amount of a photochromic dye. 2. The method according to claim 1, wherein the plastic lens is a non-polymerizable gas.
Flop to plasma treatment atmosphere, then the following (e) and (f)
The method according to claim 1, further comprising a step of applying and curing a coating composition containing the component as a main component to form a cured film. (E) an organosilicon compound having a silanol group and an epoxy group, and (f) colloidal silica. 3. The method according to claim 1, wherein the plastic lens is a spectacle lens.