JPH0534649A - Manufacture of photo chromic plastic lens - Google Patents

Abstract

PURPOSE:To have a sufficient photo chromic property, to satisfy the characteristics as the lens (the first object), and to offer the lens of higher surface hardness and superior to wear resistance (the second object). CONSTITUTION:The first object is attained by polymerizing a monomer mixture consisting essentially of (a)-(d) components under the polymerization condition not including a peroxide polymerization initiator. (a): a methylacryl monomer selected from monofunctional methacrylic acid ester and polyfunctional methacrylic acid ester, (b): a hydrophilic monomer selected from (meth)acrylic acid and a hydroxy group containing (meth)acrylic acid ester, (c): alphapolyfunctional cross-linking monomer, (d): an effective quantity of photo chromic dye. The second object is attained by further including the process that it is conducted a plasma treatment for the plastic lens, being applied a coating compound consisting essentially of (e) and (f) components, being hardened and formed a hardened film. (e): an organic silicon compound having a silanol group and an epoxy group, and (f): colloidal silica.

Description

Detailed Description of the Invention

[0001]

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 is known which is colored by irradiation with light of short wavelength and is erased when irradiated with light of long wavelength, heated or left in a dark place, and photochromic containing silver halide is known. Glass is used as a sunglasses material.

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

Therefore, in JP-A-61-228402, a photochromic dye-containing resin solution is applied to this diethylene glycol bisallyl carbonate resin substrate and heated to allow the photochromic dye in the resin film to be applied to the substrate. A method of removing the photochromic dye-deficient resin film after permeating or diffusing and then applying a cured film is disclosed, and JP-A-62-10604 discloses that a photochromic dye is added to a coating liquid. Then, a method of applying this to a lens to form a photochromic dye-containing cured film is disclosed.

A plastic lens has a problem in that the surface hardness is inferior in terms of physical properties. As an improvement, for example, in JP-A-61-166824, a hydrolyzate of an organic silicon compound and an epoxy resin are added to an acrylic resin. It is disclosed that a polyorganosiloxane coating composition comprising a resin compound and an epoxy curing agent is applied and cured.

[0006]

However, the method disclosed in Japanese Patent Laid-Open No. 61-228402 mentioned above is
In order to obtain a sufficient photochromic concentration, treatment at a high temperature exceeding the heat resistant temperature of the substrate is necessary, 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 Laid-Open Patent Publication No. 62-10604 has a limited solubility of the photochromic dye in the coating solution, and it is difficult to obtain sufficient photochromic property. Even if the amount of dissolution increases, there is a problem that the physical properties of the photochromic dye-containing cured film deteriorate.

Furthermore, the polyorganosiloxane-based cured film disclosed in the above-mentioned JP-A-61-166824 has a problem that the abrasion resistance against 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 abrasion resistance improver, is added to this polyorganosiloxane-based cured film, there is a problem that the adhesiveness with the base resin (especially acrylic resin) is significantly reduced. It was

The present invention is to eliminate the above-mentioned drawbacks of the conventional method for producing a photochromic plastic lens, and the first object thereof 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, the second purpose of which is to provide a photochromic lens having sufficient photochromic properties, satisfying the characteristics as a lens, and having high surface hardness and excellent abrasion resistance. It is to provide a method of manufacturing a plastic lens.

[0010]

The first object is to initiate a peroxide-based polymerization of a monomer mixture containing the following components (a), (b), (c) and (d) as main components. It was achieved by a method for producing a photochromic plastic lens, which comprises a step of obtaining a plastic lens having photochromic properties by polymerizing under a polymerization condition containing no agent. (A) at least one methacrylic monomer selected from monofunctional methacrylic acid ester and polyfunctional methacrylic acid ester, (b) at least one selected from (meth) acrylic acid and hydroxyl group-containing (meth) acrylic acid ester Hydrophilic monomer, (c) at least one polyfunctional crosslinking monomer, and (d) an effective amount of a photochromic dye. The second purpose is to subject the plastic lens obtained above to plasma treatment, and then apply and cure a coating composition containing the following components (e) and (f) as the main components to form a cured film. It was achieved by further including the step of (E) An organosilicon compound having a silanol group and an epoxy group, (f) colloidal silica.

The present invention will be described in detail below. In the present invention, a monomer mixture containing the above-mentioned components (a), (b), (c) and (d) as a main component is polymerized under a polymerization condition containing no peroxide type polymerization initiator. To obtain a photochromic plastic lens.

As described later, the condition that the peroxide-based polymerization initiator is not included is that the photochromic dye as the component (d) is decomposed and the photochromic property disappears or remarkably occurs when the initiator is included. Because it will decline.

The reason for using the methacrylic monomer of the component (a) 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. As the methacrylic monomer as the component (a), at least one selected from monofunctional methacrylic acid esters and polyfunctional methacrylic acid esters is used. Examples of the monofunctional methacrylic acid ester include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, ethylhexyl methacrylate, benzyl methacrylate, phenyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, adamantyl methacrylate, and the like. Further, as the polyfunctional methacrylic acid ester, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, 1,
4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol trimethacrylate, glycerin dimethacrylate and the like can be mentioned. The content of component (a) is preferably 30 to 95% by weight, more preferably 40 to 95% by weight, based on the total monomer mixture. The ratio of component (a) is 3 in the total monomer mixture.
If it is less than 0% by weight, the transparency, light resistance, strength, etc., which are the characteristics of the acrylic resin, are deteriorated. Due to the relative decrease, the adhesion with the cured film becomes weak.

As the hydrophilic monomer as the component (b), at least one selected from (meth) acrylic acid and hydroxyl group-containing (meth) acrylic acid ester is used. In the present specification, “(meth) acrylic acid” means both “acrylic acid” and “methacrylic acid”.
Examples of these are acrylic acid, methacrylic acid, hydroxyethyl esters of acrylic acid or methacrylic acid,
Examples thereof include chlorohydroxypropyl ester of acrylic acid or methacrylic acid. The content of the component (b) is preferably 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 of the adhesion to the cured film becomes weak, while if it exceeds 50% by weight, the water absorption becomes large and the physical properties of the resin surface are increased. It becomes unstable, and it is easy to get rough and pocked. In addition, the releasability and transferability during imprinting may be deteriorated.

The polyfunctional crosslinkable monomer as the component (c) is a crosslinkable monomer having two or more functional groups, examples of which include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, and triethylene glycol dimethacrylate. Polyfunctional methacrylic acid esters such as methacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, glycerin trimethacrylate, ethylene glycol diacrylate, triethylene Polyfunctional acrylic acid 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 its type, but it is generally in the range of 3 to 50% by weight in the total monomer mixture, and in the case of ethylene glycol dimethacrylate, it is preferably 3 to 30% by weight. When the proportion of the component (c) is less than 3% by weight, the heat resistance becomes insufficient, while when it exceeds 50% by weight, the impact resistance is lowered, and cracks, cracks and the like are likely to occur at the time of mold release. However, there is a problem that it becomes difficult to perform, which is not preferable.

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 dye, a spirooxazine-based dye or the like is used. The spiropyran-based dyes include halogens of indolinospyrobenzopyran indole and benzene ring, methyl, ethyl, methylene, ethylene, each substituent such as a hydroxyl group, indole of indinospironaphthopyran and halogen of naphthalene ring, methyl, ethyl. , Each substitution product of methylene, ethylene, hydroxyl group, halogen of indole ring of indinospiroquinopyran, each substitution product of methyl, ethyl, methylene, ethylene, hydroxyl group, halogen of indole ring of indinospiropyridopyran, methyl , Ethyl, methylene, ethylene, hydroxyl groups and the like. Further, as the spirooxazine-based dye, indolinospirobenzoxazine indole and benzene ring halogen,
Substitutes of methyl, ethyl, methylene, ethylene, hydroxyl group, etc., indole of indinospironaphthooxazine and halogens of naphthalene ring, methyl, ethyl, methylene, ethylene, substitute groups of hydroxyl group, indolinospirophenanthrooxazine Halogen of the indole ring of methyl, ethyl, methylene, ethylene, each substitution product such as a hydroxyl group, halogen of the indole ring of indinospiroquinolinoxazine, methyl, ethyl, methylene, ethylene,
Examples thereof include substituents such as a hydroxyl group, and halogen, methyl, ethyl, methylene, ethylene and substituents of a piperidine ring and a naphthalene ring of piperidinospironaphthoxazine. Of these, spirooxazine-based dyes are particularly preferable in terms of light resistance, and it is more effective to use an organic nickel-based stabilizer in combination. As a commercially available product of the spirooxazine-based dye, Photo. PNO,
Sunmax (a dye-containing acrylic monomer) manufactured by Tsukuba Scientific Research Institute Co., Ltd. and the like can be mentioned.

The preferable content of the photochromic dye as the component (d) cannot be uniquely defined because it greatly varies depending on the kind of the photochromic dye as shown in the examples described later, but it cannot be specified uniquely. An amount effective for fading and fading smoothly, that is,
The amount is selected so that the color density at the time of coloring is high and the light transmittance at the time of decoloring is high.

It is also possible to add other monomers copolymerizable with the components (a), (b) and (c) to the monomer mixture within a range not impairing the effects of the present invention. . Examples of these monomers include ethyl methacrylate and n-methacrylate.
Butyl, ethylhexyl methacrylate, benzyl methacrylate, phenyl metal acrylate, cyclohexyl methacrylate, isobornyl methacrylate, methacrylic acid esters such as adamancil methacrylate, methyl acrylate, ethyl acrylate, n-butyl acrylate, ethylhexyl acrylate, Acrylic acid esters such as cyclohexyl acrylate, benzyl acrylate, phenyl acrylate and isobornyl acrylate, nuclear-substituted styrenes such as styrene, methylstyrene, dimethylstyrene, chlorostyrene, dichlorostyrene, bromstyrene, p-chloromethylstyrene, etc. And α-methylstyrene, acrylonitrile, methacrylonitrile, maleic anhydride, N-
Examples thereof include substituted maleimides.

In the method for producing the photochromic plastic lens of the present invention, it is preferable to use the cast polymerization method, and usually thermosetting polymerization is adopted. That is, it is a method of adding an appropriate amount of a polymerization initiator to a monomer mixture, injecting it into a mold, and performing heat polymerization. As the polymerization initiator at this time,
Azo initiators such as 2,2'-azobisisobutyronitrile and 2,2'-azobis (2,4-dimethylvaleronitrile) can be preferably used. As described above, peroxide-based initiators such as benzoyl peroxide, lauroyl peroxide, and t-butylperoxy-2-ethylhexanoate diminish 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 based on the total amount of monomers.
It is preferable to use the above range. Further, the heating temperature is largely in the range of 20 to 80 ° C., though it varies greatly depending on the initiator used. Polymerization by intense light irradiation may reduce the photochromic property, which is not preferable.

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

The photochromic plastic lens obtained according to the present invention is obtained by polymerizing the monomer mixture under the condition that the peroxide-based polymerization initiator is not contained. The photochromic dye which is the component d) remains in the plastic lens without being decomposed. Therefore, it has a so-called photochromic property of being colored by irradiation of ultraviolet rays and being erased by blocking of ultraviolet rays, and is preferably used for sunglasses and the like.

According to the present invention, the photochromic plastic lens obtained as described above may be subjected to plasma treatment, and further coating and curing treatment of the coating composition may be performed, whereby the surface hardness of the plastic lens is improved. It is possible to obtain a photochromic practic lens having excellent abrasion resistance and scratch resistance.

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

The coating and curing treatment of the coating composition on the plastic lens which has been subjected to the plasma treatment is carried out 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. The organosilicon compound having a silanol group and an epoxy group has a general formula

[0026]

[Chemical 1]

A hydrolyzate of a trifunctional organosilicon compound represented by the formula (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) is preferable. As the trifunctional organosilicon compound, R _{1 in} the formula is a methyl group, an ethyl group, a propyl group or a butyl group,
It is particularly preferable that ₂ is a methylene group, an ethylene group, a propylene group or a butylene group.

On the other hand, as the colloidal silica, a high concentration of water-dispersed colloidal silica (for example, having a SiO ₂ solid content of 40% or more) is used in order to prevent excess water from remaining 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. From that point of view, the amount of colloidal silica in the coating composition is preferably set to 75 mol% (SiO ₂ solid content conversion value) or more based on the total amount of the colloidal silica and the organosilicon compound. The curing agent is not particularly limited, but acetylacetone metal complex compounds are effective, and among them, acetylacetone aluminum complex compounds can be used particularly effectively. The amount added is an amount 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 of the hydrolyzate of the colloidal silica (SiO ₂ conversion) and the organosilicon compound. Is.

An organic acid is used for the hydrolysis of the organosilicon compound of the formula (I). Examples of this include acetic acid, formic acid, and propionic acid, but acetic acid is preferably used because of the stability of the coating composition. The amount of organic acid added is 5 to 1 mol of the total amount of colloidal silica and organosilicon compound.
It is preferably 30 g. If it is less than this range, gelation of the coating composition is likely to occur, and if it is more than this range, odor becomes strong and workability deteriorates.

Further, in order to make the hydrolysis uniform and to adjust 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 combination with isopropyl alcohol, butanol and the like is more preferable. The proportion of cellosolve is preferably 3% by weight or more, and particularly preferably 10% by weight or more based on the total amount of the solvent. Particularly when the proportion of colloidal silica is high, if the proportion of cellosolve in the solvent is less than 3% by weight of the total amount of the solvent, gelation occurs during the preparation of the coating composition and it becomes difficult to obtain a coating composition.

A silicone type surfactant may 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, it is possible to add an ultraviolet absorber, an antioxidant or the like. The coating composition can be applied to the lens substrate by a dipping method, a spin coating method, a roll coating method, a spray method or the like. Curing of the applied coating composition is carried out by heat treatment, and the heating temperature is preferably 40 to 150 ° C, particularly preferably 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. The methods for evaluating physical properties in Examples and Comparative Examples are as follows.

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

(B) Surface hardness The surface was rubbed 50 times (reciprocating) with steel wool # 0000 under an additional load of 1000 g, and the scratch resistance was judged according to the following criteria. A: Almost no scratches. B: Very slightly scratched. C: A little scratched. D: Many scratches.

(C) The surface of the adhesive cured film was cut into 1 mm intervals to form a square pattern (10 × 10 pieces), and a cellophane adhesive tape (No. 1 manufactured by Nichiban Co., Ltd.) was used.
405) was strongly adhered, and it was rapidly peeled off in the direction of 90 degrees, and the number of gobang eyes left was examined.

(D) Appearance The transparency, coloring state, surface state and the like were examined by visual inspection.

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 Co., Ltd.) 2
A solution prepared 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 is added to 95 parts by weight of γ-glycidoxypropyltrimethoxysilane (trifunctional organosilicon compound) with stirring at 35 ° C. The mixture was added dropwise, stirred at room temperature for 8 hours, and then left standing for 16 hours. To 320 parts by weight of this hydrolysis solution, 80 parts by weight of methyl cellosolve and 1 part of isopropyl alcohol
8 parts by weight of 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 part 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.
It was a solid content conversion value).

(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. The amount of colloidal silica in the coating composition at this time was 8 based on the total amount of colloidal silica and γ-glycidoxypropyltrimethoxysilane.
It was 5 mol% (SiO ₂ solid content conversion value).

(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 as Photo. P
0.01 parts by weight of NO, azobis type chemical compound V-70 0.0 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 Co., Ltd. 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 added and mixed and dissolved. This mixed solution was poured into a mold consisting of two glass molds and a plastic gasket, placed in a hot air circulation type heating furnace, heated at 37 ° C for 8 hours, and then heated to 90 ° C over 8 hours. Then, the mixture was heated as it was 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 diopter of 0.00 diopter. 12 more
Annealing was performed by heating at 0 ° C. for 2 hours.

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

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

[Examples 3 to 10] A lens with a cured film was prepared in the same manner as in Example 2 except that the plasma treatment conditions and the type of coating composition were changed as shown in Table 1, and the same evaluation was performed. It was As shown in Table 1, the results were excellent in surface hardness, adhesion and appearance. In addition, these lenses with a cured film have photochromic properties and can be suitably used as spectacle lenses. The responsiveness of the change in the transmittance of this lens at 554 nm when irradiated with ultraviolet rays and when shielded from light was the same as in Example 1.

[0043]

[Table 1]

[Examples 11 to 18] Plastic lenses were 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 then plasma treated in the same manner as in Example 2. Then, coating treatment was performed to obtain a lens with a cured film. The obtained lens with a cured film was evaluated in the same manner. The results are as shown in Table 2, surface hardness, adhesion,
The appearance was excellent. In addition, these lenses with a cured film have photochromic properties and can be suitably used as spectacle lenses. The responsiveness of the change in the transmittance of this lens at 554 nm when irradiated with ultraviolet rays and when shielded from light was the same as in 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 component (c), which was a crosslinkable monomer, was not used. It did not have a proper lens shape.

[0046]

[Table 2]

Example 19 70 parts by weight of methyl methacrylate, 20 parts by weight of 2-hydroxypropyl methacrylate, 10 parts by weight of ethylene glycol dimethacrylate,
As a photochromic dye, 1.0 part by weight of 5-chloroindolinospironaphthoxazine, and as a radical polymerization initiator, an azobis-based chemical product V-7 manufactured by Wako Pure Chemical Industries, Ltd.
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 performed using this prepared solution in the same manner as in Example 1 to provide a surface-cured film to obtain a highly transparent lens. The lens thus obtained was excellent in surface hardness A and adhesion 100/100. Further, this lens has photochromic properties and can be suitably used as a lens for spectacles. FIG. 2 shows the responsiveness of the change in transmittance of this lens at 610 nm when the high pressure mercury lamp is irradiated with ultraviolet light and when it is shielded from ultraviolet light. At this time, the temperature was 21 ° C., and the ultraviolet intensity of the lens surface was measured by Ushio Electric Co., Ltd. UIT-102 (photoreceiver UVD3
It was 1.2 mW when measured with a 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, 40 parts by weight of Sunmax acrylic monomer containing a spirooxazine photochromic dye (Tsukuba Scientific Research Institute Co., Ltd.
Manufactured by 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 performed using this prepared solution in the same manner as in Example 1 to provide a surface-cured film to obtain a highly transparent lens. The lens thus obtained was excellent in surface hardness A and adhesion 100/100. Further, this lens has photochromic properties and can be suitably used as a lens for spectacles. FIG. 3 shows the responsiveness of the change in transmittance of this lens at 610 nm when the high pressure mercury lamp irradiates ultraviolet rays and when it is shielded from ultraviolet rays. The temperature at this time is 24 ° C., and the UV intensity of the lens surface is measured by the Ushio Electric Co., Ltd.
It was 1.2 mW when measured with -102 (light receiver UVD365PD).

[0049]

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

[Brief description of drawings]

FIG. 1 is a graph showing the responsivity of the change in transmittance at 554 nm when the plastic lens of Example 1 is irradiated with ultraviolet light and shielded from ultraviolet light;

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

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

Claims (3)

[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 type polymerization initiator. And a step of obtaining a plastic lens having photochromic properties according to the above. (A) at least one methacrylic monomer selected from monofunctional methacrylic acid ester and polyfunctional methacrylic acid ester, (b) at least one selected from (meth) acrylic acid and hydroxyl group-containing (meth) acrylic acid ester (C) at least one polyfunctional crosslinking monomer, and (d) an effective amount of a photochromic dye. 2. The method according to claim 1, further comprising a step of subjecting the plastic lens to a plasma treatment, and then applying and curing a coating composition containing the following components (e) and (f) as main components to form a cured film. The method described. (E) An organosilicon compound having a silanol group and an epoxy group, (f) colloidal silica. 3. The method according to claim 1, wherein the plastic lens is a spectacle lens.