JPH09329701A - Primer composition for plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a primer compsn. for a plastic lens capable of contributing to an improvement in the impact resistance of the plastic lens having a silicon cured layer and an antireflection layer and the adhesion property between a plastic lens base material and the cured layer by applying the compsn. to the surface of the plastic lens base material, then drying the coating prior to the formation of the cured layer and the inorg. antireflection layer at the time of the production. SOLUTION: This compsn. is used for forming a primer layer on the plastic lens base material prior to the formation of the cured layer consisting of a silicon resin and the inorg. antireflection layer on the surface of the cured layer. In such a case, the compsn. consists of a urethane soln. composed of an active hydrogen-contg. compd. selected from alkylene glycols, polyalkylene glycols, poly(alkylene adipates), poly-ε-caprolactone, polybutadiene glycols, poly(alkylene carbonates) or silicone polyol and polyisocyanate.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastic lens primer composition, and more particularly, to the impact resistance of a plastic lens and the curing of the plastic lens base material when producing a plastic lens having a cured layer and an antireflection film. The present invention relates to a primer composition suitable as a primer layer provided to improve the adhesion to the layer.

[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, surface modification for the purpose of adding high added value to the lens by improving the defect that it is easily scratched due to insufficient surface hardness or by suppressing the surface reflection that causes flickering of images and objects. 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 layer or an inorganic antireflection film is provided, there is a problem that the impact resistance of the plastic lens is lowered, and in particular,
In the plastic lens coated with these two films at the same time, the impact resistance becomes more remarkable, and improvement is desired.

Further, it has been a major problem in the past to improve the adhesion between the silicone-based cured layer and the plastic lens substrate when the silicone-based cured layer is applied to the plastic lens substrate. The surface of the plastic lens substrate has been 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 layer. 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 surface hardness by coating with a silicon-based hardened layer and the improvement of surface reflection by coating with an inorganic antireflection film is one of the advantages of plastic lenses. The impact resistance is deteriorated, 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 and an inorganic antireflection film is applied as in the above-mentioned conventional technique. This point will be described in more detail.
In the method disclosed in JP-A-214302, which uses a primer composition containing an acrylic and / or methacrylic compound and an aromatic vinyl compound as main components, an emulsion is used for forming a primer layer. Since water is used in the above method, there are problems such as residual water during the drying of the primer and a long drying time. Further, when a plastic lens base material is provided with a silicone-based cured layer and an inorganic antireflection film, the adhesion is good, but the center thickness of the lens is less than 2.0 mm and the impact resistance satisfies US FDA standards. 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 this epoxy compound becomes a primer layer only when heated in the presence of an epoxy curing catalyst. Therefore, a long curing time is required. Further, a plastic lens provided with a silicone-based cured layer 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 layer and the lens substrate. However, impact resistance is not improved.

Further, in the method disclosed in Japanese Patent Laid-Open No. 61-114203, a plastic lens having a primer layer, a silicon hardened layer, 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 order to pass the impact resistance test of eyeglass lenses according to the US FDA standard for plastic lenses having a hardened layer and an inorganic antireflection film even if a primer layer is provided, in the case of a minus lens, the center thickness of the lens is 2.0 mm or more. This increases the edge thickness of the lens and causes the lens to be heavy, which impairs the external appearance and is not preferable in practice.

Therefore, an object of the present invention is to apply and cure the surface of a plastic lens substrate before providing the hardened layer and the inorganic antireflection film in the production of the plastic lens having the hardened silicon layer and the antireflection film. Accordingly, it is an object of the present invention to provide a primer composition for a plastic lens, which can improve the impact resistance of the plastic lens and the adhesion between the plastic lens substrate and the cured layer.

[0008]

The inventors of the present invention have conducted extensive studies to achieve the above-mentioned object, and as a result, alkylene glycols, polyalkylene glycols, poly (alkylene adipates), poly-ε- A composition containing a urethane solution of an active hydrogen-containing compound selected from caprolactone, polybutadiene glycols, poly (alkylene carbonates) or silicone polyols and a polyisocyanate is applied to the surface of a plastic lens substrate and cured to form a primer layer. After that, it was found that the impact resistance of the plastic lens and the adhesion between the plastic lens base material and the cured layer can be improved by providing the silicone-based cured layer and the inorganic antireflection film.

Therefore, the present invention is for a plastic lens used for forming a primer layer on the surface of a plastic lens substrate prior to providing a cured layer made of a silicone resin and an inorganic antireflection film on the surface of the cured layer. A primer composition comprising an active hydrogen-containing compound selected from alkylene glycols, polyalkylene glycols, poly (alkylene adipates), poly-ε-caprolactone, polybutadiene glycols, poly (alkylene carbonates) or silicone polyols. The subject matter is a primer composition for a plastic lens, which is composed of a urethane solution with polyisocyanate.

Hereinafter, the present invention will be described in more detail.

Any known plastic lens may be used as the plastic lens substrate to which the primer composition of the present invention is applied.

Embedded image Those obtained by polymerizing the diethylene glycol bisallyl carbonate represented by are 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.

The primer composition of the present invention comprises a urethane solution of an active hydrogen-containing compound and polyisothianate.
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; polybutadiene glycol such as poly (1,4-butanediene) glycol and poly (1,2-butanediene) glycol Le ethers, poly (alkylene carbonate) such as poly (hexamethylene carbonate) s;
Examples include silicone polyols, but it is also possible to use other known active hydrogen-containing compounds.

Examples of polyisocyanates include tolylene diisocyanate, xylylene diisocyanate,
4,4'-diphenylmethane diisocyanate, 1,5
-Naphthalene diisocyanate, 3,3'-dimethyl-
Aromatic diisocyanates such as 4,4'-diphenyl diisocyanate; 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 4,4'-
Aliphatic diisocyanates such as dicyclohexylmethane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane and trimethylhexamethylene diisocyanate can be mentioned. Further, as the polyisocyanate, hydrogenated xylylene diisocyanate described in JP-A-61-114203; biuret bond of hexamethylene diisocyanate or isocyanurate bond; reaction adduct of hexamethylene diisocyanate and trimethylolpropane 2-isocyanatoethyl-2,6-diisocyanate hexanoate; 1,6,11-undecane triisocyanate; reaction adduct of isophorone diisocyanate with trimethylolpropane; reaction adduct of xylylene diisocyanate with trimethylolpropane; It is also possible to use a so-called block-type polyisocyanate such as a reaction adduct of bis (isocyanatomethyl) cyclohexane and trimethylolpropane.

The primer composition of the present invention comprises a urethane solution of an active hydrogen-containing compound and polyisocyanate. Here, the urethane solution may be a mixture of an active hydrogen-containing compound and polyisocyanate, or may be a polymer. Here, the "mixture" means a mixture of the active hydrogen-containing compound and the polyisocyanate in a state before polymerization, and when a solution containing this mixture is applied to the surface of the plastic lens substrate and cured, polymerization occurs, and the polyurethane resin Is formed. on the other hand,
"Polymer" means a polyurethane resin obtained by polymerizing an active hydrogen-containing compound and polyisocyanate, and a primer comprising a polyurethane resin is obtained by applying a solution containing this polymer onto the surface of a plastic lens substrate and curing it. A layer is formed.

Whether to use a mixture of an active hydrogen-containing compound and a polyisocyanate or a polymer as an essential component in the primer composition is appropriately determined depending on the types of the active hydrogen-containing compound and the polyisocyanate. That is, if the active hydrogen-containing compound and polyisocyanate give a thermosetting polyurethane resin,
It is preferred to use the mixture and heat it on the plastic lens substrate to form the primer layer. If both monomers give a thermoplastic polyurethane resin, it is preferable to use a polymer and apply a solution containing the polymer onto the substrate to dry it to form the primer layer.

The film thickness of the primer layer obtained by applying the primer composition of the present invention on the surface of a plastic lens substrate is preferably 0.01 to 30 μm. 0.01
If it is less than μm, the effect of improving impact resistance is not so great,
If it exceeds 30 μm, the surface accuracy when applied to the lens is lowered. It is particularly preferably 1 to 20 μm.

The primer composition of the present invention is used by diluting a urethane solution of an active hydrogen-containing compound and polyisocyanate to a concentration suitable for coating. As a solvent used for dilution, hydrocarbons and halogenated carbon are used. Examples thereof include hydrogens, alcohols, ketones, esters, ethers, and the use of other known solvents is also possible. 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.
When a mixture of an active hydrogen-containing compound and polyisocyanate is used, it is preferable to use a solvent that does not react with them. 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 primer composition is applied by a spinner method, a dipping method,
It may be appropriately selected from other known methods. In order to form a primer layer, the primer composition of the present invention is applied to the surface of a plastic lens substrate and then 30
The heating may be performed at any temperature in the range of ℃ to 200 ℃, preferably 60 ℃ to 150 ℃. Depending on the solvent used, the desired primer layer is formed by heating for 1 to 60 minutes. When a composition containing a mixture of an active hydrogen-containing compound and a polyisocyanate is used as the primer composition, these monomers are polymerized on a plastic lens substrate by heating to form a polyurethane resin, and a solvent of the solvent by heating is formed. Along with volatilization, a primer layer made of polyurethane resin is formed.

On the other hand, when a composition containing a polymer of an active hydrogen-containing compound and a polyisocyanate (polyurethane resin) is used as the primer composition, the solvent is volatilized by heating to form a primer layer composed of the polyurethane resin. It is formed.

After forming a primer layer using the primer composition of the present invention, the primer layer may be formed on the primer layer, but is not limited thereto.

Embedded image (Here, R ¹ and R ² are each a hydrocarbon group having an alkyl group, an alkenyl group, an allyl group, a halogen group, an epoxy group, an amino group, a mercapto group, a methacryloxy group or a cyano group; and R ³ is a carbon atom. An alkyl group, an alkoxyalkyl group, an acyl group or a phenyl group having a number of 1 to 8; m and n are 0 or 1) and / or a hydrolyzate thereof, and colloidal silica (particles A coating composition having a diameter of 1 to 100 mμ) is coated and cured to provide a silicon-based cured layer.

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 spray method, a dipping method and a spinner method, 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.

A plastic lens obtained by applying a primer composition of the present invention on a plastic lens substrate and curing the same, and providing a cured layer on the primer layer has impact resistance and a plastic lens substrate and a cured layer. Has excellent adhesion with.

After coating and curing the organosilicon composition,
A single-layer or multi-layer antireflection film is 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 , metal oxides such as tantalum oxide,
Fluoride such as MgF ₂ is used.

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

The plastic lens with an antireflection film obtained above has a highly hard surface having durability in addition to 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.

[0027]

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 and coating curing of the primer composition of the present invention 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 dipped on the plastic lens substrate obtained in (1) by a dipping method (pulling speed: 10
cm / min). The applied base lens is 120
Heat cured at ℃ for 30 minutes and film thickness is 8.0μm on the substrate.
Was formed.

(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%) 350 parts by drops, while stirring,
After the completion of dropping, the mixture was further stirred at 10 ° C overnight. 52 parts of methyl cellosolve and 20 parts of isopropyl alcohol
8 parts, 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 composition was prepared.

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 as} an inorganic substance (optical film) is formed 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) and SiO ₂ (nd = λ / 4) were sequentially applied in a multilayer coating 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 The primer layer obtained in (3) and (4) above,
The performance of the plastic lens with a hardened layer, the primer layer, the hardened layer, and the plastic lens with an antireflection film was evaluated by the method described below.

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

(B) Steel Wool Hardness The coated surface was rubbed with steel wool having a hardness of # 0000 to evaluate the degree of scratches. The criteria are as follows: a: No scratches even when strongly rubbed.

B: Strong rubbing causes a slight scratch.

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 is measured according to JIS D-0202.
The crosscut tape test method was applied in accordance with the above. 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
From a height of 7 cm, it was allowed to fall naturally toward the center of the lens once, and those that did not crack were accepted. The center thickness of all lenses used in this test was 1.2 mm.

The primer layer, the plastic lens with a 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. The excellent results in impact resistance and adhesion were obtained because the primer composition of the present invention was used to form a primer layer made of a specific polyurethane resin on the surface of a plastic lens substrate in advance, and then a cured layer Is formed.

Example 2 A primer layer, a plastic lens with a cured film and a primer layer, a cured layer were prepared in the same manner as in Example 1 except that a polyurethane resin solution having a solid content of 5% was used as the primer composition. A plastic lens with an antireflection film was obtained and tested in the same manner as in Example 1. The test results are shown in Table-1.

[Embodiment 3] LQ351 used in Embodiment 1
Instead of 0, commercially available polyurethane LQ3505 [manufactured by Sanyo Kasei Co., Ltd., solid content concentration 30% (using polyalkylene adipate)] was used, and toluene / IPA (mixing ratio 2/1) was used.
A primer layer, a plastic lens with a cured film and a primer layer, and a cured layer were prepared in the same manner as in Example 1 except that a polyurethane resin solution obtained by diluting with a mixed solvent to a solid content of 5% was used as a primer composition. Then, a plastic lens with an antireflection film was obtained and tested in the same manner as in Example 1. The test results are shown in Table-1.

Example 4 Commercially available polyurethane E380
Example 1 except that the polyurethane resin solution obtained by adjusting the primer concentration to 3% by adding tetrahydrofuran using [manufactured by Nippon Elastollan Co., Ltd. (using poly (alkylene carbonate)]) was used as the primer composition. A primer layer, a hardened film-coated plastic lens and a primer layer, a hardened layer, and an antireflection film-coated plastic lens were obtained in the same manner as in 1. The test results are shown in Table-1.

Example 5 Commercially available polyurethane E580
Example 1 except that a polyurethane resin solution obtained by adjusting the primer concentration to 3% by adding tetrahydrofuran using [Japan Elastollan Co., Ltd. (using poly ε-caprolactone)] was used as the primer composition. Similarly, a primer layer, a hardened layer-equipped plastic lens and a primer layer, a hardened layer, an antireflection-coated plastic lens were obtained and tested in the same manner as in Example 1. The test results are shown in Table-1.

Example 6 Commercially available polyurethane SP-2
5 [manufactured by Sanyo Kasei Co., Ltd., solid content concentration 30% (poly-ε-
Caprolactone was used)] and methyl ethyl ketone was added to adjust the primer concentration to 5%, and a polyurethane resin solution obtained was used as a primer composition in the same manner as in Example 1 except for using a primer layer and a hardened layer plastic lens. And 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.

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 Instead of the commercially available polyurethane used in Example 1, the polyurethane obtained by the following production method was used, and this polyurethane was diluted with tetrahydrolane so that the solid content concentration was 10%. A primer layer, a plastic lens with a cured layer, and a primer layer, a cured layer, and a plastic lens with an antireflection film were obtained in the same manner as in Example 1 except that the polyurethane solution obtained in this way was used as the primer composition.

Polyurethane production method : 108 parts of Terratan 3000 (polyether glycol manufactured by DuPont) and 38 parts of diethylene glycol as the polyol, and hexamethylene diisocyanate as the isocyanate were used. The mixture was mixed to have an NCO / OH ratio of 1.0, and then the mixture was diluted with a toluene solvent so that the solid content was 30%, and then 90 ° C.
The mixture was stirred overnight at 0 ° C. to complete the reaction, and post-treated by a conventional method to obtain the desired polyurethane. 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 thus obtained 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] Styrene / butyl acrylate / hydroxyethyl methacrylate / acrylic acid (10
(0/100/2/5 mixing ratio) of a quaternary copolymer (this quaternary copolymer is an acrylic polyol and is not included in the active hydrogen-containing compound used in the present invention) and hexamethylene diisocyanate. A solution having a solid content of 10% obtained by mixing with an NCO / OH ratio of 2/1 and diluting with methyl isobutyl ketone / ethyl acetate (50/50 mixing ratio) was used as a primer composition. A primer layer was formed in the same manner as in Example 1 except that a polyurethane cured film was formed by applying it on the above and heat treatment.
A plastic lens with a hardened layer and a primer layer, a hardened 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 with a hardened layer and a hardened layer and a plastic lens with an antireflection film were 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 as in Example 1 was performed. The test 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 same primer composition as in Example 7 was applied and cured on the obtained plastic lens substrate in the same manner as in Example 7 to form a primer layer. Then, the same procedure 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, and 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 11 150 parts of diethylene glycol bisallyl carbonate, 40 parts of methyl methacrylate, 6 parts of perloyl IPP (diisopropyl peroxycarbonate manufactured by NOF CORPORATION) were mixed and stirred, and then the mixture was insoluble. The substance was removed by a filter, and the filtrate was poured into a mold made of a molded gasket of ethylene / ethyl acrylate copolymer resin and two glass molds to obtain a plastic lens substrate. The same primer composition as in Example 10 was applied to the surface of the obtained plastic lens substrate and cured to form a primer layer. Then, the same procedure as in Example 10 is performed to obtain a primer layer, a plastic lens with a cured layer and a primer layer, a cured layer, and a plastic lens with an antireflection film.
The same test was performed. The results are shown in Table 1.

Example 12 150 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) were mixed and stirred, and then, Then, the insoluble matter of this mixed solution was removed with a filter, and the filtrate was poured into a mold formed of a gasket formed of ethylene / ethyl acrylate copolymer resin and two glass molds to obtain a plastic lens substrate. The same primer composition as in Example 10 was applied to the surface of the obtained plastic lens substrate and cured to form a primer layer. Then, it carried out like Example 10 and obtained a primer layer, a plastic lens with a hardening layer, a primer layer, a hardening layer, and a plastic lens with an antireflection film, and it tested like Example 1. The results are shown in Table 1.

Example 13 Terratan 3000 (polyether glycol manufactured by DuPont) as a polyol 10
Using 8 parts and 38 parts of diethylene glycol and hexamethylene diisocyanate as the isocyanate,
These were mixed so that the NCO / OH ratio was 1.0.
Furthermore, it was diluted with toluene so that the solid content was 20%. A primer layer, a plastic lens with a cured layer and a primer layer, a cured layer and a plastic lens with an antireflection film were obtained in the same manner as in Example 1 except that this was used as a primer composition, and the same test as in Example 1 was carried out. .

Example 14 Plassel L-220AL (poly-ε-caprolactone polyol manufactured by Daicel Co., Ltd.) as a polyol and hexamethylene diisocyanate as an isocyanate were used, and these were used as NCO / O.
They were mixed so that the H ratio was 1.0. Furthermore, solid content 20
It was diluted with toluene so that it became%. A primer layer, a plastic lens with a cured layer and a primer layer, a cured layer and a plastic lens with an antireflection film were obtained in the same manner as in Example 1 except that this was used as a primer composition, and the same test as in Example 1 was carried out. .

[0060]

[Table 1]

From Table 1, it can be seen that 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 Examples 1 to 14 are all in appearance, scratch resistance and impact resistance. It was excellent in adhesiveness and adhesion. In particular, excellent results in impact resistance and adhesion were obtained because the primer composition of the present invention was used to form a primer layer made of a specific polyurethane resin on the surface of a plastic lens substrate in advance and then cured. This is because the layers have been formed.

[0062]

Industrial Applicability The plastic lens primer composition of the present invention is used for producing a plastic lens having a cured layer made of a silicone resin and an inorganic antireflection film, prior to providing the cured layer and the antireflection film. The impact resistance of the plastic lens and the adhesion between the plastic lens base material and the cured layer can be improved by applying and curing it on the surface of the base material.

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Claims (1)

[Claims] 1. A primer composition for a plastic lens, which is used for providing a cured layer made of a silicone resin and a primer layer on the surface of a plastic lens substrate prior to providing an inorganic antireflection layer on the surface of the cured layer. And 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. A primer composition for a plastic lens, which comprises the urethane solution described above.