JPH06331803A - Plastic lens - Google Patents

Abstract

PURPOSE:To provide both characteristics of the scratching resistance sufficient for withstanding use and the impact resistance sufficient for meeting the requirements specified in FDA of the United States by forming a primer layer to be formed as an impact absorptive layer of an epoxy resin on one surface of a plastic lens base material. CONSTITUTION:The primer layer as the impact absorptive layer and a hard coating layer as a scratching resistant layer are formed successively from a base material side in this order on at least one surface of the plastic lens base material. The primer layer consists of the epoxy resin. The epoxy resin is an epoxy resin of bisphenol type A. The primer layer consisting of the epoxy resin forms a three-dimensional network structure which is insoluble in solvents and is nonmeltable by heat by the ring opening polymn. of the epoxy groups and, therefore, the elasticity is increased and the impact resistance is improved. The formation of single layer or many layers of antireflection films on the surface of the hard coating layer is possible as well.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastic lens having excellent adhesion, scratch resistance, impact resistance, chemical resistance, weather resistance and antireflection property of a coating film.

[0002]

2. Description of the Related Art In recent years, plastics, which are lighter and easier to dye than glass, have attracted attention as a material for spectacle lenses, and many plastic lenses having a high refractive index and low chromatic aberration have been provided in response to this. In general, plastic lenses have the drawback of being extremely vulnerable,
Normally, a silicon-based hard coat film is provided on the surface of the lens, and an inorganic substance is vapor-deposited on the hard coat film to suppress surface reflection that causes image flicker. It is provided with the membrane provided.

However, a plastic lens provided with both a hard coat film and an antireflection film has a drawback that its impact resistance is significantly inferior to a plastic lens provided with no film at all, and this problem is solved. It is being studied in various fields. For example, Japanese Patent Application Laid-Open No. 63-14001 discloses a method of providing a primer layer of polyurethane resin between a plastic lens and a hard coat film.

Although the impact resistance is improved by providing the primer layer, the scratch resistance is inferior to that of the plastic lens having no primer layer.

[0005]

SUMMARY OF THE INVENTION The present invention is a primer
In a layered plastic lens, the
Scratch resistance and U.S. FDA sufficient to withstand use even when a docor layer or an antireflection film is further provided thereon.
The aim is to obtain a plastic lens that has both properties of impact resistance sufficient to pass the standard.

[0006]

The present invention according to claim 1 provides a primer layer as a shock absorbing layer and a hard coat layer as a scratch resistant layer on at least one surface of a plastic lens substrate. In the plastic lens formed in this order from the base material side, the primer layer is made of an epoxy resin.

The present invention according to claim 2 is characterized in that, in claim 1, a single-layer or multilayer antireflection layer is formed on the surface of the hard coat layer.

According to a third aspect of the present invention, in the first aspect, the epoxy resin is a bisphenol A type epoxy resin.

The present invention according to claim 4 is characterized in that, in claim 1, the hard coat layer is an organosilicon compound represented by the following general formula (I) or a hydrolyzate thereof. is there. [General Formula] R ¹ _m R ² _n Si (OR ³ ) _4-mn (I) (In the formula, R ¹ and R ² are an alkyl group having 1 to 20 carbon atoms,
It represents an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 19 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and a halogen atom. R ³ represents an alkyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms. m and n are 0 or 1. )

[0010]

In the plastic lens of the present invention, since the primer layer formed as an impact absorbing layer on at least one surface of the plastic lens substrate is made of epoxy resin, the scratch-resistant layer is formed on the surface of the primer layer. When a hard coat layer as described above is laminated, a plastic lens having both scratch resistance sufficient to withstand use and impact resistance sufficient to pass the US FDA standard is obtained. Obtainable.

That is, a primer layer made of an epoxy resin forms a three-dimensional network structure insoluble in a solvent and infusible by heat by ring-opening polymerization of an epoxy group, so that elasticity is increased and impact resistance is improved. Is something that can be done. Generally, epoxy resins are rich in types of curing agents, and various characteristics can be obtained by combining them.

The epoxy resin of the present invention is not particularly limited, but it has been widely put into practical use in paints, castings, and the like. For example, bisphenol A, bisphenol F and catechol, Resorcinol or (poly) ethylene glycol, (poly) propylene glycol
, Neopentyl glycol, glycerin, trimethylolpropane, pentaerythritol, diglycerol
Polyglycidyl ether obtained from epichlorohydrin and polyhydric alcohol such as diol and sorbitol, cyclopentadiene oxide or cyclohexene oxide or hexahydrophthalic acid or hydrogenated bisphenol A and polyglycidyl ester obtained from epichlorohydrin or Aliphatic epoxy resin such as polyglycidyl ether, tetrafunctional epoxy resin obtained by addition of epichlorohydrin to metaxylene diamine or 1,3-bis (aminomethyl) cyclohexane and ring closure, epoxidized vegetable oil, novolac type Epoxy novolac obtained from phenol resin and epichlorohydrin, polyolefin-based epoxy resin synthesized by peroxide method, epoxy resin obtained from phenolphthalein and epichlorohydrin Doo and methyl methacrylate - - Acrylic monomers such bets - like or copolymers such as styrene-glycidyl methacrylate in. These may be used alone or in the form of two or more condensates.

Further, the thickness of the primer layer is from 0.05 to
The thickness is 5 μm, preferably 0.5 to 3 μm. When the film thickness is less than 0.05 μm, a sufficient function as impact resistance cannot be obtained, and when it exceeds 5 μm, the heat resistance of the primer layer is deteriorated and the surface accuracy is remarkably lowered.

In the present invention, the hard coat layer formed as a scratch resistant layer on the surface of the primer layer is preferably made of any of silicone, melamine and acrylic resins. It is preferably formed, and a silicone resin is particularly preferable. This is because the silicone-based resin can provide a hard coat layer that is harder than the melamine-based and acrylic-based resins.

Particularly preferably used silicone resin is an organic silicon compound represented by the following general formula (I) and / or a hydrolyzate thereof. [General Formula] R ¹ _m R ² _n Si (OR ³ ) _4-mn (I) (In the formula, R ¹ and R ² are an alkyl group having 1 to 20 carbon atoms,
It represents an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 19 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and a halogen atom. R ³ represents an alkyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms. m and n are 0 or 1. )

R ¹ and R ² may be substituted, and in such a case, specific examples of the substituent include a hydroxy group; an amino group, a dibenzylamino group, and (2-methacryloxyethyl) amino. Groups such as amino groups; methoxy groups, tert-butoxy groups, and other alkoxy groups; benzyloxy groups, phenethyloxy groups, and other aralkoxy groups; phenoxy groups, 2-naphthyloxy groups, and other aryloxy groups; acetoxy groups, benzoyloxy groups, methacryloxy groups Carbamoyloxy groups such as acyloxy group, N-phenylcarbamoyloxy group, N- (2-methacryloxyethyl) carbamoyloxy group; alkyl groups such as methyl group, trifluoromethyl group, glycidyl group;
Alkyl groups such as benzyl group; aralkyl groups such as benzyl group and phenethyl group; aryl groups such as phenyl group and 1-naphthel group; halogen groups such as chloro group and bromo group; cyano group; carboxylic acid group, carboxylic acid Carboxylic acid group such as soda group; Nitro group; Acyl group such as acetyl group and methacryl group; Carbamoyl group such as N-methylcarbamoyl group; Alkoxycarbonyl group such as ethoxycarbonyl group; Sodium sulfonate group, sulfone Sulfonic acid groups such as acid groups; sulfamoyl groups.

Specific examples of the acyl group of R ³ include an acetyl group and a benzoyl group, and an alkyl group and an aryl group.
Group, aralkyl group and the like, and preferable specific examples of the alkyl group, aryl group and aralkyl group include R
^{The same as 1} and R ² can be mentioned. R ³ may also be substituted, and as the substituent, the same substituents as the substituents for R ¹ and R ² can be mentioned as preferable examples.

Specific examples of the organosilicon compound represented by the formula (I) include methyl silicate, ethyl silicate,
n-propyl silicate, i-propyl silicate, n
-Butyl silicate, sec-Butyl silicate, t-
Butyl silicate, tetraacetoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltrimethoxyethoxysilane, methyltriacetoxysilane, methyltributoxysilane, methyltripropoxysilane, methyltriamyloxysilane, methyltriphenoxysilane, Methyltribenzyloxysilane, methyltriphenethyloxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, α-glycidoxyethyltrimethoxysilane,
α-glycidoxyethyltriethoxysilane, β-glycidoxyethyltrimethoxysilane, β-glycidoxyethyltriethoxysilane, α-glycidoxypropyltrimethoxysilane, α-glycidoxypropyltriethoxysilane, β-glycidoxypropyltrimethoxysilane, β-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ
-Glycidoxypropyltriethoxysilane, γ-glycidoxypropyltripropoxysilane, γ-glycidoxypropyltributoxysilane, γ-glycidoxypropyltrimethoxyethoxysilane, γ-glycidoxypropyltriphenoxysilane, α-glycidoxybutyltrimethoxysilane, α-glycidoxybutyltriethoxysilane, β-glycidoxybutyltrimethoxysilane, β-glycidoxybutyltriethoxysilane, γ
-Glycidoxybutyltrimethoxysilane, γ-glycidoxybutyltriethoxysilane, δ-glycidoxybutyltrimethoxysilane, δ-glycidoxybutyltriethoxysilane, (3,4-epoxycyclohexyl)
Methyltrimethoxysilane, (3,4-epoxycyclohexyl) methyltriethoxysilane, β- (3,4-
Epoxycyclohexyl) ethyltrimethoxysilane,
β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) ethyltripropoxysilane, β- (3,4-epoxycyclohexyl) ethyltributoxysilane, β-
(3,4-epoxycyclohexyl) ethyltrimethoxyethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriphenoxysilane, γ- (3,4-epoxycyclohexyl) propyltrimethoxysilane,
γ- (3,4-epoxycyclohexyl) propyltriethoxysilane, δ- (3,4-epoxycyclohexyl) butyltrimethoxysilane, δ- (3,4-epoxycyclohexyl) butyltriethoxysilane, glycidoxymethylmethyl Dimethoxysilane, glycidoxymethylmethyldiethoxysilane, α-glycidoxyethylmethyldimethoxysilane, α-glycidoxyethylmethyldiethoxysilane, β-glycidoxyethylmethyldimethoxysilane, β-glycidoxyethylmethyl Diethoxysilane, α-glycidoxypropylmethyldimethoxysilane, α-glycidoxypropylmethyldiethoxysilane, β-glycidoxypropylmethyldiethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypro Rumethyldiethoxysilane, γ-glycidoxypropylmethyldipropoxysilane, γ-glycidoxypropylmethyldibutoxysilane, γ-glycidoxypropylmethylmethoxyethoxysilane, γ-glycidoxypropylmethyldiphenoxysilane, γ-glycidoxypropylethyldimethoxysilane, γ-glycidoxypropylethyldiethoxysilane, γ-glycidoxypropylvinyldimethoxysilane, γ-glycidoxypropylvinyldiethoxysilane, γ-glycidoxypropylphenyldimethoxysilane Silane, γ-glycidoxypropylphenyldiethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltrimethoxyethane Toxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltriacetoxysilane, γ-chloropropyltrimethoxysilane, γ-chloropropyltriethoxysilane, γ-chloropropyltriacetoxysilane, 3,3,3-trifluoropropyl Trimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, β-cyanoethyltriethoxysilane, chloromethyltrimethoxysilane, chloromethyltriethoxysilane, N- (Β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropylmethyi Dimethoxysilane,
γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltriethoxysilane, N-
(Β-aminoethyl) -γ-aminopropylmethyldiethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, γ-chloropropylmethyldimethoxysilane, γ-chloropropylmethyldi Ethoxysilane, dimethyldiacetoxysilane, γ-methacryloxypropylmethyldimethoxysilane, γ-methacryloxypropylmethyldiethoxysilane, γ-
Examples are mercaptopropylmethyldimethoxysilane, γ-mercaptopropylmethyldiethoxysilane, methylvinyldimethoxysilane, and methylvinyldiethoxysilane.

These organosilicon compounds can be used alone or in combination of two or more.

There is no problem even if finely divided inorganic substances, which are commonly used for the purpose of improving the surface hardness, are added to the cured film of the present invention. Here, the fine particle inorganic material preferably has an average particle diameter of about 1 to 300 μm, more preferably about 5 to 200 μm.

Specific examples of finely divided inorganic materials include silicon oxide compounds such as silicon dioxide, aluminum oxide compounds such as aluminum trioxide, titanium oxide compounds such as titanium dioxide, zirconium oxide compounds such as zirconium dioxide, and oxidations of tin dioxide. Tin compounds, antimony trioxide, antimony pentoxide and other antimony oxide compounds, titanium dioxide and antimony pentoxide composite sol, tungsten oxide sol, tin oxide and tungsten oxide composite sol, tin oxide and tungsten oxide and tin oxide composite sol Examples of the modified sol coated with

There is no problem in the present invention even if various kinds of curing agents are included in the cured coating film of the present invention for the purpose of accelerating curing, curing at low temperature and the like in forming the cured coating film. Various epoxy resin curing agents, various organic silicon resin curing agents, etc. are known as curing agents that are often used.

Specific examples of these curing agents include various organic acids and their acid anhydrides, nitrogen-containing organic compounds,
Examples thereof include various metal complex compounds or metal alkoxides, and various salts such as alkali metal organic carboxylates and carbonates.

In the present invention, a single-layer or multi-layer antireflection film may be formed on the surface of the hard coat layer. In this case, the antireflection film can be formed of a coating film of metal, metal or metalloid oxide or fluoride, such as S.
Examples thereof include metal oxides such as iO ₂ and ZrO ₂ , and films such as MgF ₂ .

In the primer layer, if necessary, a leveling agent for improving coatability, an ultraviolet absorber or an antioxidant for improving weather resistance, a pigment, a dye or a photochromic material for coloring. It is also possible to appropriately add a colorant such as a material and an additive such as a surfactant for obtaining a good coating film.

The resin material of the plastic lens substrate used in the present invention is not particularly limited, but the liquid hardening compound is a benzene ring in the main chain and / or side chain thereof,
A resin material having at least one of a naphthalene ring, a carbonate bond, a urethane bond, and a halogen element is particularly preferable.

The resin material of the plastic lens substrate which is particularly preferably used is polymethyl methacrylate and its polymer, polycarbonate, diethylene glycol bisallyl carbonate polymer (CR39), polyester, especially polyethylene terephthalate. Tartrate, unsaturated polyester, epoxy resin, polyether sulfone and the like.

Further, a component of the hexamethylene diisocyanate cyclic trimer represented by the chemical formula 1, a component of the diol compound represented by the chemical formula 2, and a compound represented by the chemical formula 3. A resin material having a component composed of a compound consisting of the above and a component composed of a radical polymerization-reactive compound having a divinylbenzene and an aromatic ring is more preferable, and the use of the constitution of the present invention for this resin material has a great effect.

[0029]

[Chemical 1]

[0030]

[Chemical 2]

[0031]

[Chemical 3]

The method of molding the plastic lens substrate used in the present invention can be carried out in almost the same manner as the usual method of polymerizing plastics. For example, a monomer mixture is mixed with glass mold and ethylene-vinyl acetate copolymer. Pour into the mold assembled by the gasket made, cured at a predetermined temperature for a predetermined time, after taking out from the mold,
A molded plastic lens substrate can be obtained by post-curing at a predetermined temperature if necessary. Of course, it goes without saying that the present invention can use a plastic lens substrate molded by another method.

In producing the plastic lens of the present invention, first, in order to form a primer layer as an impact absorbing layer on at least one surface of a plastic substrate, a primer coating comprising an epoxy resin and a curing agent. Is applied to a plastic lens substrate, and a curing treatment is performed.

Examples of the curing agent include primary, secondary, and tertiary amines, polyamides, polyesters, anhydrides such as oxalic acid, and boron trifluoride compounds. For example, when a polyamide or an anhydride is used as the curing agent, the pot life at room temperature can be made very long, and the curing agent is appropriately selected in order to obtain the desired characteristics.

Examples of the solvent used for diluting the epoxy resin include alcohols, ketones, esters, ethers and the like, and other known solvents can be used. Particularly preferable are methanol, ethyl acetate, methyl ethyl ketone and ethylene glycol monoethyl ether, but these may be used alone or as a mixed solvent of two or more kinds. A mixture of a thermosetting epoxy resin, a curing agent and a solvent serves as a primer paint.

The primer coating method is not particularly limited as long as it is a known method such as a spin coating method or a dipping method for a liquid composition in the presence or absence of a solvent of a composition which is a precursor of a cured product. There is no. In order to improve the coating property of the plastic lens substrate, it is desirable to carry out a pretreatment such as an alkali treatment, a plasma treatment, or an ultraviolet treatment, if necessary.

The primer layer can be formed as a uniform film by applying the primer coating and then solidifying or curing the epoxy resin and the curing agent by a method suitable for the curing method. Although it is possible to cause the curing reaction at room temperature by using a special curing agent having a particularly high chemical reactivity, generally heating can shorten the time until the curing reaction is completed.

However, when it is cured under high temperature conditions, discoloration of the plastic and decoloration of the dyed product occur, and the strength also decreases, so it is not desirable to raise the curing temperature too much. The time required for curing varies depending on the heating temperature, but is 15 to 90 minutes.

Next, a hard coat layer as a scratch resistant layer is provided on the surface of the primer layer. As the hard coat agent, one selected from silicone-based, melamine-based, and acrylic-based resins diluted with a solvent is preferably used.

Like the primer layer, the hard coat layer is a dipping method, a spray method or a spin coat method for a liquid composition in the presence or absence of a solvent of a composition which is a precursor of a cured product. Any method such as a commonly used coating method may be used, but the dipping method is most suitable in consideration of workability. After applying the hard coat agent, the hardening treatment may be carried out by a method suitable for hardening the hard coat agent such as heat hardening, ultraviolet ray hardening, electron beam hardening and the like.

When a single-layer or multi-layer antireflection film is provided on the surface of the hard coat layer, an oxide or fluoride of a metal, metal or semimetal selected as a material for forming the antireflection film. For example, a metal oxide such as SiO ₂ or ZrO ₂ , MgF ₂ or the like may be deposited by a known method such as a vacuum deposition method, a sputtering method, an ion plating method, an ion beam assist method.

[0042]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited thereto.

Example 1 (1) Plastic lens base material A general plastic lens base material for eyeglasses of CR-39 was used.

(2) Preparation of primer composition and coating curing: 10.0 parts by weight of a commercially available bisphenol A type epoxy resin, 1.00 parts by weight of a commercially available ethylenediamine as a curing agent, and a commercially available fluorine-based leveling agent. Leveling agent "Florade FC-430" (Sumitomo 3M Limited)
A mixture of 0.01 parts by weight) and 50.0 parts by weight of methanol as a solvent was sufficiently stirred until a uniform state was obtained, and this was used as a primer composition.

A lens coated on the plastic lens substrate (1), which had been subjected to an alkali treatment with this primer composition as a pretreatment, by the dipping method (pulling speed: 180 cm / min) was heat treated at 80 ° C. for 30 minutes. Then, the primer composition was cured to form a 1.2 μm-thick primer layer on the lens.

(3) Preparation of Hard Coat Agent (A) Preparation of Preliminary Composition A In a reaction vessel equipped with a rotor, 248 parts by weight of γ-glycidoxypripyrmethyldiethoxysilane was charged, and the magnet was used. 0.05 with vigorous stirring using a tic stirrer
36 parts by weight of a normal hydrochloric acid aqueous solution was added at once and stirred for 1 hour to obtain a hydrolyzate.

The hydrolyzate obtained was treated with ethanol 56.
After adding 6 parts by weight and 53.4 parts by weight of ethylene glycol, 4.7 parts by weight of aluminum acetylacetate were added and sufficiently mixed and dissolved to prepare a preliminary composition A.

(B) Preparation of Preliminary Composition B A reaction vessel equipped with a rotor was charged with 212.4 parts by weight of γ-glycidoxypropyltrimethoxysilane, and the temperature inside the vessel was kept at 10 ° C. While stirring vigorously with a tic stirrer, 0.01N hydrochloric acid aqueous solution 48.
6 parts by weight was gradually added dropwise. Immediately after the completion of dropping, cooling was stopped to obtain a liquid hydrolyzate.

Ethanol 77.1 was added to the resulting hydrolyzate.
After adding 1 part by weight and 37.7 parts by weight of ethylene glycol, 7.65 parts by weight of aluminum acetyl acetate was added and mixed sufficiently to prepare a preliminary composition B.

(C) Preparation of Hard Coating Agent In a glass container, 20 parts by weight of the preliminary composition A, 80 parts by weight of the preliminary composition B, and a commercially available methanol silica sol (average particle size: 10 to 20 nm; 200 parts by weight, manufactured by Chemical Industry,
0.45 part by weight of a silicone-based surfactant was sufficiently stirred and mixed to prepare a liquid coating composition.

(4) Coating and curing of hard coating agent The hard coating agent obtained in (3) was applied on the primer layer of the plastic lens substrate having the primer layer obtained in (2). Dipping method (pulling speed 100 cm / m
in). The coated lens is 60 at 110 ℃
The hard coat layer was cured by heat treatment for a minute. The film thickness of the obtained coating film was 2.3 μm.

(5) Formation of Antireflection Film A five-layer antireflection film of SiO ₂ / ZrO ₂ system was formed on the plastic lens substrate having the primer layer and the hard coat layer obtained in (4). It was formed by a vacuum evaporation method.

As is clear from the test results shown in Table 1, the plastic lens having the composite film thus obtained is excellent in film adhesion, scratch resistance, dyeability and impact resistance. there were.

Example 2 10.00 parts by weight of a commercially available bisphenol A type epoxy resin, 0.40 parts by weight of triethylamine as a curing catalyst,
A commercially available fluorine-based leveling agent "Florade FC-430" (manufactured by Sumitomo 3M Limited) as a leveling agent.
A mixture of 01 parts by weight and 50.0 parts by weight of ethyl acetate as a solvent was sufficiently stirred until a uniform state was obtained, and this was used as a primer composition.

A plastic lens having a composite film was prepared in the same manner as in Example 1 except that this primer composition was used, and a test was conducted in the same manner as in Example 1. The test results are shown in Table 1.

Example 3 20.00 parts by weight of a commercially available bisphenol A type epoxy resin, 0.5 parts by weight of boron trifluoride as a curing catalyst, and a commercially available fluorine-based leveling agent "Florade FC-430" as a leveling agent. (Sumitomo 3M Limited)
0.01 part by weight, methyl ethyl ketone 6 as a solvent
A mixture composed of 0.0 parts by weight was sufficiently stirred until a uniform state was obtained, and this was used as a primer composition.

A plastic lens having a composite film was prepared in the same manner as in Example 1 except that this primer composition was used, and the test was conducted in the same manner as in Example 1. The test results are shown in Table 1.

Example 4 In the first step, 9.71 parts by weight of 1-methacryloxy-3- (phenylphenoxy) -2-propanol (purity 99.2% by weight) and hexamethylene diisocyanate were cyclic. Trimer (content of isocyanate group: 23.1% by weight, effective molecular weight of 545 based on purity of isocyanate group: 545) 8.41 parts by weight and 2,2-bis [3,5-
Dibromo-4- (2-hydroxyethoxy) phenyl]
Mix with 4.88 parts by weight of propane.

Dibutyltin dilaurate as a urethane-forming reaction catalyst was added to this mixture at a ratio of 0.01% by weight to the mixture, and the urethane-forming reaction was carried out at 60 ° C. for 2 hours to obtain a product.

Then, in the second step, 1-methacryloxy-3- (2-phenylphenoxy) -2-propanol (purity 99.2% by weight) was added to the product obtained in the first step.
7.0 parts by weight were added and mixed.

Lauryl peroxide was added to the mixture as a radical polymerization catalyst in an amount of 1.0% by weight based on the mixture.
At a rate of 4, and poured into a glass mold,
0 ° C for 10 hours, 60 ° C for 4 hours, 80 ° C for 2 hours, 9
The radical copolymerization reaction was carried out by changing the reaction conditions stepwise at 0 ° C. for 1 hour. By this method, a colorless and transparent plastic lens substrate having a center thickness of 1.2 mm and a diameter of 72 mm was obtained.

A plastic lens having a composite film was prepared in the same manner as in Example 1 except that this plastic lens substrate was used, and a test was conducted in the same manner as in Example 1. The test results are shown in Table 1.

Comparative Example 1 All Example 1 except that no primer layer was provided.
A plastic lens having a composite film was prepared in the same manner as in (1) and tested in the same manner as in Example 1. The test results are shown in Table 1.

Comparative Example 2 Example 4 except that no primer layer was provided.
A plastic lens having a composite film was prepared in the same manner as in (1) and tested in the same manner as in Example 1. The test results are shown in Table 1.

The performance evaluation of the plastic lenses according to each example and comparative example was performed by the following test method.

1) Adhesion of Film Crosshatch tape test for evaluating the adhesion of the film was carried out as follows. That is, a 1 mm square grid (100 squares) is cut with a cutter on the surface of a lens having a film, an adhesive tape is pasted on the cut, and the tape is then cut.
Repeatedly peeling off the film 10 times repeatedly, and counted the number X of grids of the film remaining without being stripped from the lens. Then, the result is expressed as "X / 100".
"100/100" indicates that the film did not peel at all as a result of the cross-hatch tape test.

2) Scratch resistance A 5-layer antireflection film of SiO ₂ / ZrO ₂ system was formed on a plastic lens substrate having a primer layer and a hardcoat layer by a vacuum vapor deposition method, and then antireflection was performed. From above the membrane #
It was rubbed with 1000 steel rolls and examined for scratch resistance. The evaluation was performed according to the following criteria. A: Does not hurt even with strong rubbing B: Slightly hurt with strong rubbing C: Scratches with weak rubbing

3) Dyeing property A general disperse dye, 7 parts of Nikon Light Brown, was added to 1000 parts of water in a dyeing bath at 90 ° C. for 10 minutes for dyeing by dipping treatment, and a visual transmittance meter was used. When the value was 70% or less, the dyeability was determined to be good.

4) Impact resistance Evaluation was carried out by a steel ball falling ball test. Twelve 16.2g steel balls
The lens was freely dropped from a height of 7 cm toward the center of the lens, and the number of times before breaking was taken as the impact resistance of the lens, and the lens was dropped up to 5 times. The center thickness of all lenses used in this test was 1.0 mm.

The adhesion, scratch resistance and impact resistance of the film are tested with a primer layer, a hard coat layer and an antireflection layer, and the dyeability test is performed with an antireflection layer. It is a performance test before, that is, when only the primer layer and the hard coat layer are applied.

[0071]

[Table 1]

[0072]

According to the present invention, by using an epoxy resin as a primer layer formed as a shock absorbing layer on the surface of a plastic lens substrate, a hard coat layer as a scratch resistant layer or further If an anti-reflective coating is laminated on top of it, it has sufficient scratch resistance and US FDA resistance to withstand use.
It is possible to obtain a plastic lens that has both properties of impact resistance sufficient to pass the standard.

In addition to the above effects, the plastic lens of the present invention has the effect of improving the dyeability.
The effect is particularly remarkable when a plastic lens substrate having poor dyeability is used.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Zushio Konishi 3 2-3 Marunouchi, Chiyoda-ku, Tokyo Nikon Corporation (72) Inventor Tomoya Sanchome 3 2-3 Marunouchi, Chiyoda-ku, Tokyo Stock Company Nikon

Claims (4)

[Claims] 1. A plastic lens in which a primer layer as a shock absorbing layer and a hard coat layer as a scratch resistant layer are formed on at least one surface of a plastic lens substrate in this order from the substrate side. The plastic lens, wherein the primer layer is made of epoxy resin. 2. The plastic lens according to claim 1, wherein a single-layer or multi-layer antireflection layer is formed on the surface of the hard coat layer. 3. The plastic lens according to claim 1, wherein the epoxy resin is a bisphenol A type epoxy resin. 4. The hard coat layer has the following general formula (I):
The plastic lens according to claim 1, which is an organosilicon compound represented by or a hydrolyzate thereof. [General Formula] R ¹ _m R ² _n Si (OR ³ ) _4-mn (I) (In the formula, R ¹ and R ² are an alkyl group having 1 to 20 carbon atoms,
It represents an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 19 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and a halogen atom. R ³ represents an alkyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms. m and n are 0 or 1. )