JPH0854501A - Production of plastic lens - Google Patents

Abstract

PURPOSE:To improve appearance, adhesion property, wear resistance, scratching resistance and shock resistance by forming a specified primer layer on the surface of a plastic lens base body and further forming an antireflection film on a specified silicon hardened layer by vapor deposition of inorg. material. CONSTITUTION:A primer layer of 0.01 to 30mum thickness is formed on the surface of a plastic lens base body. This primer layer consists of a polyurethane resin produced from polyisocyanates and active hydrogen-contg. compds. selected from alkyleneglycols, polyalkyleneglycols and the like. Then a coating compsn. containing an org. silicon compd. expressed by formula and/or its hydrolyzed material is applied and hardened to form a silicon hardened layer. Further, a single-layer or multilayer antireflection film is formed on the surface of the silicon layer by vapor deposition of an inorg. material. In formula, R<1>, R<2> are alkyl groups, alkenyl groups, aryl groups or the like, R<3> is a C1- C8 alkyl group, phenyl group, or the like, and n and m are 0 or 1.

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 plastic lens, more specifically, excellent impact resistance, abrasion resistance, hot water resistance, chemical resistance, adhesion between a lens base material and a cured layer, and the like. And a method for manufacturing a plastic lens having the characteristics of US FDA standard.

[0002]

2. Description of the Related Art Plastic lenses are lightweight, shock resistant,
It has advantages such as easy workability and dyeability, and has been rapidly spreading in recent years in the field of optical materials, especially spectacle lenses. Furthermore, the surface for the purpose of imparting a high added value to the lens by improving the defect which is said to be easily scratched due to insufficient surface hardness or by suppressing the surface reflection that causes flickering of images and objects. Many modifications have already been proposed, and the market for plastic lenses is expanding more and more. For example, to improve the surface hardness of the former, a silicon-based cured film is provided, and to improve the surface reflection of the latter, an inorganic substance is vapor-deposited on the lens surface to provide an antireflection film, thereby improving high hardness or antireflection ability. A plastic lens having the same is also provided. However, when a silicon-based cured film or an inorganic antireflection film is provided, there is a problem that the impact resistance of the plastic lens is lowered, and above all,
In the plastic lens coated with these two films at the same time, the reduction in impact resistance becomes so remarkable that improvement is desired.

[0003] Further, when a silicone-based cured film is applied to a plastic lens substrate, improving the adhesion between the silicone-based cured film and the plastic lens substrate has hitherto been a major issue. The surface of the plastic lens substrate is modified by methods such as plasma etching or other etching treatment, or by providing a primer layer between the plastic lens substrate and the silicone-based cured film. As a conventional technique for surface modification by means of, for example, a method of using an epoxy compound as a primer composition (JP-A-60-
214301), and a method using a primer composition containing an acrylic and / or methacrylic compound and an aromatic vinyl compound as main components (JP-A-60-214302).
JP-A-61-114203) and a method using a primer composition comprising an acrylic polyol and a polyfunctional organic isocyanate compound.

[0004]

As described above, one of the problems associated with the improvement of the surface hardness by coating the silicon-based cured film and the improvement of the surface reflection by the coating of the inorganic antireflection film is the advantage of the plastic lens. There is a certain decrease in impact resistance, and this problem cannot be solved even in a plastic lens in which a silicone-based cured film is applied after the primer layer is provided as in the above-mentioned prior art, and further an inorganic antireflection film is applied. This point will be described in more detail.
In the method disclosed in Japanese Patent Publication No. 214302, which uses a primer composition containing an acrylic and / or methacrylic compound and an aromatic vinyl compound as main components, emulsion is used for forming a primer layer. Since water is used, there are problems such as residual water when drying the primer and a long drying time. Also, when a silicone-based cured film and an inorganic antireflection film are applied to a plastic lens substrate, the adhesion is good, but the center thickness of the lens is less than 2.0 mm and the impact resistance satisfies the US FDA standard. Is difficult

In the method disclosed in JP-A-60-214301, an epoxy compound is used as a material for forming a primer layer, and the epoxy compound is heated in the presence of an epoxy curing catalyst for the first time. Therefore, a long curing time is required. Further, a plastic lens provided with a silicone-based cured film after providing this primer layer and further provided with an inorganic antireflection film has excellent properties such as chemical resistance and improved adhesion between the silicone-based cured film and the lens substrate. However, impact resistance is not improved.

Further, in the method disclosed in Japanese Patent Application Laid-Open No. 61-114203, a plastic lens having a primer layer, a silicon-based cured film, and an inorganic antireflection film is used for abrasion resistance and abrasion resistance. Chemical resistance, hot water resistance,
Although the scratch resistance and the like are improved, the impact resistance is not so improved.

As described in detail above, the conventional surface modification method by primer coating is effective in adhesion, chemical resistance, and abrasion resistance, but impact resistance is still unsolved. In the case of a minus lens, the plastic lens having a cured film or a silicone-based cured film and an inorganic antireflection film is required to pass the impact resistance test of eyeglass lenses according to the US FDA standard even when a primer layer is provided. Must be 2.0 mm or more, which increases the edge thickness of the lens and causes the lens to be heavy, which impairs the appearance and is not preferable in practice.

Therefore, the object of the present invention is to eliminate the drawbacks of the conventional plastic lens in which a primer layer is provided on a plastic lens substrate, and then a silicone-based cured layer and an inorganic antireflection film are provided, and abrasion resistance, It is an object of the present invention to provide a method for producing a plastic lens, which has properties such as hot water resistance, chemical resistance, and adhesion between a lens base material and a cured layer, while at the same time imparting excellent impact resistance.

[0009]

Means for Solving the Problems As a result of repeated studies to achieve the above-mentioned object, the present inventors have found that alkylene glycols, polyalkylene glycols, poly (alkylene adipates), poly-ε-caprolactone. On the surface of the plastic lens substrate, a 0.01 to 30 μm-thick primer layer made of a polyurethane resin obtained from an active hydrogen-containing compound selected from polybutadiene glycol, poly (alkylene carbonate) s or silicone polyol, and polyisocyanate. A plastic lens obtained by providing a hardened layer made of a specific silicone resin, and further forming a single-layer or multi-layered antireflection film on the surface thereof by vapor deposition of an inorganic substance, if necessary. Abrasion resistance, hot water resistance, chemical resistance, close contact between lens base material and cured layer Not only has excellent sex, it was found to have excellent impact resistance.

Therefore, the present invention contains active hydrogen selected from alkylene glycols, polyalkylene glycols, poly (alkylene adipates), poly-ε-caprolactone, polybutadiene glycols, poly (alkylene carbonates) or silicone polyols. A primer layer made of a polyurethane resin obtained from a compound and polyisocyanate and having a film thickness of 0.01 to 30 μm is provided on the surface of a plastic lens substrate, and then the general formula

[Chemical 3] (Here, R ¹ and R ² are each an alkyl group, an alkenyl group,
Allyl group, or halogen group, epoxy group, amino group,
R ³ is a hydrocarbon group having a mercapto group, a methacryloxy group or a cyano group; R ³ is an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group, an acyl group or a phenyl group; n and m are 0 or 1 A), a coating composition containing an organosilicon compound and / or a hydrolyzate thereof is coated and cured to form a silicon-based cured layer, and a single layer or multiple layers of antireflection is formed on the surface by vapor deposition of an inorganic substance. A plastic lens manufacturing method is characterized in that a film is formed.

The present invention will be described in more detail below.

In the present invention, as the plastic lens substrate, any known plastic lens substrate is used.

[Chemical 4] The one obtained by polymerizing the diethylene glycol bisallyl carbonate shown by is preferably used. When the monomer of the formula (I) is polymerized, known additives such as a light stabilizer and an antioxidant and other copolymerizable monomers may be added, if necessary. The method for polymerizing the monomer of formula (I) is disclosed in detail in JP-A-57-44686.

In the present invention, a polyurethane resin layer is provided as a primer layer on the surface of the plastic lens substrate.

The polyurethane resin used as the primer composition in the present invention is a resin formed by reacting a compound having active hydrogen at both ends with a polyisocyanate. Here, as the active hydrogen-containing compound, ethylene glycol, 1,2-propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, dipropylene glycol, diethylene glycol, etc. Polyalkylene glycols such as polypropylene glycol, polyethylene glycol, polytetramethylene glycol; poly (diethylene adipate), poly (tetramethylene adipate), poly (hexamethylene adipate), poly (neopentylene adipate), etc. Poly (alkylene adipate) s; Poly-
ε-caprolactone; poly (1,4-butanediene) glycol, poly (1,2-butanediene) glycol and other polybutadiene glycols; poly (hexamethylene carbonate) and other poly (alkylene carbonate) s; silicone polyol, and other two The above-mentioned polyol compounds having a hydroxyl group can be mentioned, but other known active hydrogen-containing compounds can also be used. Examples of polyisocyanates include aromatic compounds such as tolylene diisocyanate, xylylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, and 3,3'-dimethyl-4,4'-diphenyl diisocyanate. Family-based diisocyanates;
Aliphatic diisocyanates such as 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, and trimethylhexamethylene diisocyanate can be mentioned. Use of known polyisocyanates such as hydrogenated xylylene diisocyanate, biuret-bonded or isocyanurate-bonded polyisocyanate, and reaction adducts of polyisocyanate and trimethylolpropane described in JP-A-61-114203 Is also possible.

The polyurethane resin can be produced by a known method, and various amines and metal compounds such as dibutyltin dilaurate are used as catalysts.

The thickness of the primer layer is 0.01 to 30 μm
The impact resistance is remarkably improved, and particularly preferably 1 to 21 μm
If it is less than 0.01 μm, the effect of improving the impact resistance is not so great, and if it exceeds 30 μm, the surface accuracy when applied to the lens is deteriorated.

As the solvent used in the primer composition, hydrocarbons, halogenated hydrocarbons, alcohols,
Examples thereof include ketones, esters, and ethers, and other known solvents can be used. Particularly preferred are toluene, ethyl acetate, methyl ethyl ketone and tetrahydrofuran, but these may be used alone or as a mixed solvent of two or more kinds. In addition, various leveling agents for the purpose of improving coating properties or UV absorbers and antioxidants for the purpose of improving weather resistance, dyes and pigments, and other known additives that enhance the performance and function of the film should be used in combination. You can The method of applying the primer composition may be appropriately selected from a spinner method, a dipping method, and other known methods. To form a primer layer made of a polyurethane resin, a primer composition,
After applying to the surface of plastic lens substrate, 30 ℃ ~
It may be heated at any temperature of 200 ° C, preferably 60 ° C to 150 ° C. 1 depending on the solvent used
The desired primer layer is formed by heating for ~ 60 minutes.

In the present invention, on the above cured primer layer, the general formula

[Chemical 5] (Here, R ¹ and R ² are each an alkyl group, an alkenyl group,
Allyl group, or halogen group, epoxy group, amino group,
R ³ is a hydrocarbon group having a mercapto group, a methacryloxy group or a cyano group; R ³ is an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group, an acyl group or a phenyl group; n and m are 0 or 1 A coating composition comprising an organosilicon compound represented by the formula (1) and / or a hydrolyzate thereof and colloidal silica (particle size 1 to 100 mμ) is coated and cured to provide a cured layer made of a silicone resin.

Specific examples of these organosilicon compounds include methyltrimethoxysilane, ethyltriethoxysilane, methyltriethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane and phenylmethyldimethoxysilane. ,
Vinyltriethoxysilane, vinyltris (β-methoxyethoxy) silane, vinyltriacetoxysilane, γ
-Glycidoxypropylmethyldiethoxysilane, γ-
Glycidoxypropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, glycidoxymethyltripropoxysilane, glycidoxymethyltributoxysilane or its hydrolysis Although degradation products are mentioned, other known compounds can be used. These organosilicon compounds can be used alone or in combination of two or more.

Colloidal silica has a particle size of 1 to 100 mμ.
Silica fine particles, more preferably 5-40 mμ in particle size
The silica fine particles are dispersed in a solvent such as methanol, ethanol, an alcohol such as n-butanol, or water (see JP-A-60-214302). Curing of the silicon-based composition can be achieved by heating and / or drying only the composition, ultraviolet irradiation, electron beam irradiation, or the like, but various curing agents for the purpose of promoting curing, low temperature curing, etc. can be used. You may use together. Specific representative examples of the curing agent include various organic acids and their acid anhydrides, nitrogen-containing organic compounds, various metal complex compounds or various salts such as metal alkoxides and carbonates. Particularly preferred are metal complex salts, which may be used alone,
It is also possible to use two or more types in combination.

The method of coating this may be appropriately selected from known methods such as a spraying method, a dipping method, a spinner method and the like as in the coating method of the primer composition. This curing reaction proceeds by heating to form a cured film, but it is preferable to cure in hot air at 80 ° C to 150 ° C for 30 minutes to 240 minutes.

In the present invention, after the organic silicon composition is coated and cured, a single-layer or multi-layer antireflection film is further provided. The substance used for forming the antireflection film is an inorganic substance, and examples thereof include metal, metal or metalloid oxides, fluorides, silicides, borides, carbides, nitrides and sulfides. Specifically, SiO ₂ , SiO, ZrO
₂ , Al ₂ O ₃ , TiO ₂ , Sb ₂ O ₃ , Sb ₂ O ₅ ,
Examples thereof include metal oxides such as tantalum oxide and fluorides such as MgF ₂ .

Examples of the method for forming a single-layer or multi-layer antireflection film composed of the above-mentioned substances include a vacuum vapor deposition method, a sputtering method, an ion plating method and an ion beam assist method.

The antireflection film-coated plastic lens obtained above has a durable high hardness surface in addition to the antireflection property, and since the impact resistance is improved by the primer layer, the lens for spectacles and the like. It is preferably used as an optical article.

[0025]

EXAMPLES The following examples are given to clarify the present invention, but the present invention is not limited to these examples. The parts and percentages in the examples are by weight.

[Example 1] (1) Production of plastic lens substrate Diethylene glycol bisallyl carbonate 150
Parts and 5 parts of perloyl IPP (NIPPON YU CORPORATION's diisopropyl peroxydicarbonate) were mixed and stirred, and then the insoluble matter of this mixed solution was removed by a filter, and the filtrate was molded into an ethylene / ethyl acrylate copolymer resin. It was poured into a mold made of a gasket and two glass molds. Next, 40 ° C for 4 hours, 40 ° C to 65 ° C linearly for 10 hours, 65 ° C to 85 ° C linearly for 5 hours,
After heating at 85 ° C. for 2 hours, the gasket and the glass mold were separated. Further, the obtained lens is 2 at 130 ° C.
A time annealing process was performed to remove the distortion inside the lens. The lens thus obtained was a good plastic lens for optics without internal distortion. In the following, this was used as a plastic lens substrate.

(2) Preparation of composition for primer and coating curing Commercially available polyurethane LQ3510 [manufactured by Sanyo Kasei Co., Ltd.,
Solid content concentration 30% (using polyalkylene adipate)]
Is diluted with a mixed solvent of toluene / IPA (isopropyl alcohol) (mixing ratio 2/1) to a solid concentration of 10%. Next, 50 parts of this solution was slowly mixed with stirring, and a silicon-based surfactant (L-7002 manufactured by Nippon Unicar Co., Ltd.) 0.03 was added.
Parts were added to obtain a primer composition.

This primer composition was (1) dipped onto the obtained plastic lens substrate (withdrawing speed of 10 cm).
/ Min). The applied base lens is 120 ° C
And heat-cured for 30 minutes to form a primer layer having a thickness of 8.0 μm on the substrate.

(3) Preparation of Silicone Coating Composition and Coating Curing γ-Glycidoxypropylmethyldiethoxysilane 15
While cooling 0 part to 10 ° C. and stirring, 18 parts of 0.05N hydrochloric acid was added dropwise to this over 30 minutes. Subsequently, methanol-dispersed colloidal silica (average particle size 12 ± 1 m
μ, solid content 30%) was added dropwise to the liquid while stirring, and after completion of the dropping, the mixture was further stirred at 10 ° C. overnight. To this solution, 52 parts of methyl cellosolve, 208 parts of isopropyl alcohol, 104 parts of n-butanol, and 2 parts of a silicon-based surfactant (L-7002 manufactured by Nippon Unicar Co., Ltd.) were added and mixed, and after sufficiently stirring, a silicon-based coating. A composition for use.

The coating composition was applied onto the primer layer of the plastic lens substrate having the primer layer obtained in (2) in the same manner as in the case of the primer composition. After coating, the resin was heat-cured at 120 ° C. for 3 hours to form a cured layer made of a silicone resin, and a plastic lens having a primer layer and a cured layer was obtained.

(4) Formation of Antireflection Film A mixture of ZrO ₂ / SiO ₂ which is an inorganic substance (optical film) on the hardened layer of the plastic lens having the primer layer and the hardened layer obtained in the above (3). Thickness nd = λ / 2
), ZrO ₂ (nd = λ / 2), SiO ₂ (nd = λ /
4) was sequentially coated in multiple layers by a vacuum vapor deposition method to obtain a plastic lens having a primer layer, a cured layer and an antireflection film.

(5) Test and Evaluation Results Performance evaluation of the primer layer, the plastic lens with the cured layer and the primer layer, the cured layer, and the plastic lens with the antireflection film obtained in (3) and (4), respectively, is as follows.
The method described below was used.

(A) Appearance Those having good lens transparency and surface accuracy by visual observation and having no defects in the coating film were evaluated as pass (◯), and those not having such defects were evaluated as pass (x).

(B) Steel Wool Hardness A scratch was evaluated by rubbing the coated surface with a steel wheel having a hardness of # 0000. The criteria are as follows: a: No scratches even when strongly rubbed. b: Scratch a little when strongly rubbed. c: It is scratched even if it is weakly rubbed. d: The nail is easily scratched.

(C) Adhesion: The adhesion between the cured film and the lens substrate or the antireflection film and the cured film was measured by the cross cut tape test method according to JIS D-0202. That is, using a steel knife, make 1 mm squares on the coated surface of the substrate.
00 pieces are formed. Next, a cellophane adhesive tape (trade name: Cellotape, manufactured by Nichiban Co., Ltd.) was strongly adhered onto it, and then rapidly peeled in the direction of 90 ° to examine whether or not the coating film was peeled.

(D) Impact resistance: A steel ball drop test was conducted based on the FDA standard. That is, about 16.4 g of steel balls is 127
From the height of cm, let it fall to the center of the lens once,
Those that did not break were accepted. The center thickness of all lenses used in this test was 1.2 mm.

The primer layer, the plastic lens with the cured layer and the primer layer obtained in this example, the cured layer,
Table-1 shows the evaluation results of the plastic lens with antireflection film.
Shown in The two types of composite film-coated plastic lenses had the same evaluation results and were excellent in appearance, scratch resistance, impact resistance, and adhesion.

Example 2 In preparing a primer composition, the same procedure as in Example 1 was carried out except that the solid content concentration was 5% and a polyurethane resin solution having a solid content concentration of 5% was used as the primer composition. A primer layer, a hardened film-coated plastic lens and a primer layer, a hardened layer, an antireflection-coated plastic lens were obtained, and Example 1
The same test was performed. The test results are shown in Table-1.

[Example 3] In preparing a primer composition, LQ3505 [Sanyo Kasei Co., Ltd.] was used instead of LQ3510 used in Example 1 as a commercially available polyurethane.
Made with a solid content of 30% (using polyalkylene adipate)] and diluted with a toluene / IPA (mixing ratio 2/1) mixed solvent to a solid content of 5% to obtain a polyurethane resin solution as a primer composition. A primer layer, a hardened film-coated plastic lens and a primer layer, a hardened layer, an antireflection film-coated plastic lens were obtained in the same manner as in Example 1 except for using as above. The test results are shown in Table-1.

[Example 4] In preparing a primer composition, E380 [manufactured by Nippon Elastollan Co., Ltd. (using poly (alkylene carbonate)] was used as a commercially available polyurethane, and tetrahydrofuran was added to give a primer concentration of 3%. In the same manner as in Example 1 except that the polyurethane resin solution obtained by adjusting the above was used as a primer composition, a primer layer, a plastic lens with a cured film and a primer layer, a cured layer, a plastic lens with an antireflection film were obtained, The same test as in Example 1 was carried out. The test results are shown in Table-1.

[Example 5] In preparing a primer composition, E580 [manufactured by Nippon Elastollan Co., Ltd. (using poly ε-caprolactone)] was used as a commercially available polyurethane, and tetrahydrofuran was added to bring the primer concentration to 3%. A primer layer, a plastic lens with a cured layer and a primer layer, a cured layer, a plastic lens with an antireflection film were obtained in the same manner as in Example 1 except that the prepared polyurethane resin solution was used as the primer composition. Tested as in Example 1. The test results are shown in Table-1.

Example 6 In preparing a primer composition, SP-25 [manufactured by Sanyo Kasei Co., Ltd., solid content concentration 30% (using poly-ε-caprolactone)] was used as a commercially available polyurethane, and methyl ethyl ketone was used. Was added to adjust the primer concentration to 5% and the resulting polyurethane resin solution was used as the primer composition in the same manner as in Example 1 except that the primer layer, the plastic lens with the cured layer and the primer layer, the cured layer, and the reflection were prepared. A plastic lens with a protective film was obtained and tested as in Example 1.
The test results are shown in Table-1.

Example 7 The concentration of the primer composition was adjusted to 7
%, And when applying the primer composition,
The primer layer and the cured layer are not limited to one time, and are applied by the dipping method after drying, and this series of operations of drying is repeated, and the primer layer and the cured layer are exactly the same as in Example 4 except that the coating is repeated twice. To obtain a plastic lens with a primer layer, a cured layer, and a plastic lens with an antireflection film,
The test was performed in the same manner as in Example 1. The test results are shown in Table-1.

[Example 8] In preparing the primer composition, the polyurethane obtained by the following production method was used in place of the commercially available polyurethane used in Example 1, and this polyurethane was used in a solid content concentration of 10%. Example 1 except that a polyurethane solution obtained by diluting with tetrahydrolane was used as the primer composition.
In the same manner as described above, a primer layer, a cured lens and a plastic lens with a cured layer and an antireflection film were obtained.

Polyurethane production method : 108 parts of Terratan 3000 (polyether glycol manufactured by Dyupon Co., Ltd.) and 38 parts of diethylene glycol were used as the polyol, and hexamethylene diisocyanate was used as the isocyanate. These are NCO
The mixture was mixed so that the / OH ratio was 1.0. After that, the mixture was diluted with a toluene solvent to a solid content of 30%, stirred at 90 ° C. overnight to complete the reaction, and post-treated by a conventional method to obtain the desired polyurethane. The obtained primer layer, cured layer-containing plastic lens and primer layer, cured layer, antireflection film-coated plastic lens were tested in the same manner as in Example 1, and the results shown in Table 1 were obtained.

[Example 9] The solid content of the primer composition was set to 1%, and the spinner method was used instead of the dipping method for coating. First, 0.5 μl of the primer composition was dropped on the convex surface of the plastic lens and rotated at 3000 rpm for 30 seconds. The applied lens substrate was heat-treated at 50 ° C. for 5 minutes and dried. The primer composition was similarly applied to the dried primer layer, and a series of operations for drying was repeated to perform repeated overcoating 5 times, and the final drying was performed at 120 ° C. for 10 minutes. Otherwise in the same manner as in Example 1, a primer layer, a plastic lens with a hardened layer and a primer layer, a hardened layer, a plastic lens with an antireflection film were obtained and tested in the same manner as in Example 1. The test results are shown in Table-1.

COMPARATIVE EXAMPLE 1 Instead of the commercially available polyurethane solution used in Example 1, styrene / butyl acrylate / hydroxyethyl methacrylate / acrylic acid (100/100/2/5 mixing ratio) quaternary copolymer Combined (acrylic polyol) and hexamethylene diisocyanate with N
Solid content 1 obtained by mixing at a CO / OH ratio of 2/1 and diluting with methyl isobutyl ketone / ethyl acetate (50/50 mixing ratio)
A primer layer and a cured layer were prepared in the same manner as in Example 1 except that a 0% solution was used as a primer composition, which was applied onto the surface of a plastic lens substrate and heat-treated to form a polyurethane cured film. A plastic lens, a primer layer, a cured layer, and a plastic lens with an antireflection film were obtained and tested in the same manner as in Example 1. The test results are shown in Table-1.

[Comparative Example 2] A plastic lens having a cured layer and an antireflection film was obtained in the same manner as in Example 1 except that the primer layer described in (2) of Example 1 was not applied.
The same test was performed. The test results are shown in Table-1.

Comparative Example 3 In preparing the primer composition, the solid content concentration was adjusted to 0.1%, and in applying the primer composition, the spinner method was used instead of the dipping method. First, 0.5 μl of the primer composition was dropped on the lens surface and rotated at a rotation speed of 3000 rpm for 30 seconds. The base lens coated with the primer composition was heat-treated at 120 ° C. for 30 minutes to form a primer layer having a thickness of 0.004 μm. Otherwise in the same manner as in Example 3, a primer layer, a plastic lens with a hardened layer and a primer layer, a hardened layer, a plastic lens with an antireflection film were obtained, and tested in the same manner as in Example 1. The results are shown in Table-1.

[Comparative Example 4] In applying the primer composition in Example 1, not only once, but also after drying, the primer composition was similarly applied by the dipping method, and the drying was repeated. Overcoat 5 times, film thickness 4
Example 1 except that a 1.0 μm primer layer was formed
A primer layer, a hardened layer-equipped plastic lens and a primer layer, a hardened layer, and an antireflection-coated plastic lens were obtained in exactly the same manner as in (1) and tested in the same manner as in Example 1.
The results are shown in Table-1.

Example 10 (1) Production of plastic lens Diethylene glycol bisallyl carbonate 150
Part, methyl methacrylate 15 parts, perloyl IPP
5.5 parts of diisopropyl peroxycarbonate (Nippon Oil & Fats Co., Ltd.) were mixed and stirred, then the insoluble matter of this mixed solution was removed by a filter, and the filtrate was molded into a gasket of ethylene / ethyl acrylate copolymer resin. And poured into a mold made of two glass molds. Next, linearly from 30 ° C to 40 ° C for 6 hours, linearly from 40 ° C to 50 ° C for 4 hours, linearly from 50 ° C to 70 ° C for 5 hours,
After linearly heating from 70 ° C. to 85 ° C. for 2 hours and at 85 ° C. for 1 hour, the gasket and the glass mold were separated. Further, the obtained lens was annealed at 120 ° C. for 2 hours to remove the distortion inside the lens. The lens thus obtained was a good plastic lens for optics without internal distortion.

The obtained plastic lens substrate is
The same treatment as in Example 7 was performed to obtain a primer layer, a plastic lens with a cured layer and a primer layer, a cured layer, a plastic lens with an antireflection film, and the same test as in Example 1 was carried out. The test results are shown in Table-1.

[Example 11] In the production of a plastic lens, 150 parts of diethylene glycol bisallyl carbonate, 40 parts of methyl methacrylate and 6 parts of perloyl IPP (diisopropyl peroxycarbonate manufactured by NOF CORPORATION) were mixed and stirred, then Primers were prepared in the same manner as in Example 10 except that the insoluble matter of this mixed solution was removed by a filter, and the filtrate was poured into a mold formed of a molded gasket of ethylene / ethyl acrylate copolymer resin and two glass molds. Layers, a plastic lens with a hardened layer and a primer layer, a hardened layer, a plastic lens with an antireflection film were obtained and tested as in Example 1.
The results are shown in Table-1.

[Example 12] In producing a plastic lens, 150 parts of diethylene glycol bisallyl carbonate, 15 parts of methyl methacrylate, 3 parts of diethylene glycol diacrylate, and 6 parts of perloyl IPP (diisopropyl peroxycarbonate manufactured by NOF CORPORATION). Examples except mixing and stirring, then removing the insolubles of this mixture with a filter, and pouring the filtrate into a mold made of a molded gasket of ethylene / ethyl acrylate copolymer resin and two glass molds A primer layer, a hardened layer-equipped plastic lens and a primer layer, a hardened layer, and an antireflection film-equipped plastic lens were obtained in the same manner as in Example 10, and were tested in the same manner as in Example 1. The results are shown in Table-1.

[0055]

[Table 1]

As is apparent from the above table, according to the present invention,
A plastic lens having excellent impact resistance as well as appearance, abrasion resistance, scratch resistance, and adhesion is provided.

[0057]

According to the present invention, a plastic not only has excellent appearance, adhesion, abrasion resistance, and scratch resistance, but also has significantly improved impact resistance, which is a drawback of conventional plastic lenses of the same kind. You can get a lens.

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Claims (2)

[Claims] 1. An active hydrogen-containing compound and polyisocyanate selected from alkylene glycols, polyalkylene glycols, poly (alkylene adipates), poly-ε-caprolactone, polybutadiene glycols, poly (alkylene carbonates) or silicone polyols. On the surface of the plastic lens substrate, a primer layer having a film thickness of 0.01 to 30 μm and made of a polyurethane resin obtained from (Here, R ¹ and R ² are each an alkyl group, an alkenyl group,
Allyl group, or halogen group, epoxy group, amino group,
R ³ is a hydrocarbon group having a mercapto group, a methacryloxy group or a cyano group; R ³ is an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group, an acyl group or a phenyl group; n and m are 0 or 1 A), a coating composition containing an organosilicon compound and / or a hydrolyzate thereof is coated and cured to provide a silicon-based cured layer, and a single layer or multiple layers of antireflection is formed on the surface by vapor deposition of an inorganic substance. A method for producing a plastic lens, which comprises forming a film. 2. The plastic lens substrate has the formula: The method for producing a plastic lens according to claim 1, which is obtained by polymerizing a monomer containing diethylene glycol bisallyl carbonate as a main component.